Want your kids to grow into confident money decision-makers without turning every dinner conversation into a financial lecture? In this roundtable episode, Joe sits down with Livia (“Liv”) Roder, host of the Liv Lab Podcast, Karen Holland of GiftingSense.org, and John Lanza, host of the Art of Allowance Podcast to explore what actually helps kids understand money before the stakes get big. Instead of theory, this discussion focuses on real moments when money suddenly becomes real: college price tags, house-hunting sticker shock, allowances that run out too fast, and purchases that teach better lessons than any lecture ever could. The panel shares practical ways families can build financial confidence through everyday decisions, honest conversations, and a willingness to let kids learn by doing. What the Stacking Benjamins “Confident Explorer” will gain from this episode: How to talk about money naturally so kids see it as a life skill, not a stressful taboo topic Why modeling everyday behavior matters more than formal “money talks” A simple shift from “Can I have it?” to “Is it worth it?” that builds independent thinking How small spending mistakes become powerful teaching moments when handled without shame Ways to introduce big topics like college costs gradually so kids feel informed instead of overwhelmed Real-life money lessons that sparked the conversation: Livia’s moments when money suddenly felt real, from college forms to realizing savings aren’t just “bank numbers” Karen Holland’s memorable eighth-grade back-to-school budget experiment Early allowance experiences that helped connect choices with consequences Why kids absorb far more from overheard conversations and daily habits than parents expect Practical strategies parents can use right away: Starting with simple allowance systems or “jars” to visualize spending, saving, and giving Karen’s “Does It Make Sense?” pause to slow impulsive purchases Joe’s “circle back” technique, revisiting purchases later to reflect without criticism Letting kids fail safely so regret becomes learning instead of embarrassment Helping kids split costs or contribute toward purchases to create ownership Navigating tougher parenting questions: Should kids see financial stress, or should parents shield them? How to practice age-appropriate honesty without creating anxiety Why financial jargon like FAFSA or taxes can unintentionally intimidate teens Bringing kids into real financial conversations so they build confidence early Money challenges unique to today’s kids: Teaching spending awareness in a tap-to-pay, frictionless world Cash vs. cards vs. apps and how each changes behavior Building a “pause habit” before spending when transactions feel invisible If you could teach just one money skill… The panel compares their top priorities: Awareness of cash flow and where money actually goes Thinking before buying instead of reacting emotionally Paying yourself first and building saving habits early Plus, a little basement fun along the way: Favorite purchases that truly felt worth it (from snowboards to board games to a Kindle) Stories that prove money lessons stick best when tied to real experiences Resources and next steps from each guest, including tools, calculators, and upcoming episodes This episode reinforces a core Stacking Benjamins idea: kids don’t learn money through perfect decisions. They learn through guided experience, honest conversations, and the freedom to practice while the stakes are still small. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-teach-your-kids-about-money-1806 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Live from Joe's mom's basement (where receipts go to be judged and spreadsheets fear OG), this episode tackles two big questions Stackers are asking right now. What's the best tax software for filing your 2025 return? And what should normal, long term investors make of gold, silver, and crypto taking a wild ride? Joe Saul-Sehy and OG are joined by Robert Farrington from The College Investor to break down the tax software landscape without the marketing fluff. Because if you're our Stacker avatar, you don't want hype. You want something that works, doesn't overcharge you, and doesn't suddenly upsell you because you clicked the wrong box. Then in the headline segment, the crew digs into the sharp pullback in precious metals and crypto. Is this the beginning of something bigger? A buying opportunity? Or just another reminder that chasing shiny objects (literally shiny in gold's case) can make your portfolio feel like a roller coaster? As always, Doug brings trivia, there's some basement banter, and the team separates smart strategy from financial fashion trends. Choosing the Right Tax Software (Without Overpaying): • Why FreeTaxUSA might be the best overall value for most Stackers • When TurboTax or H&R Block make sense and when you're just paying for bells and whistles • The pros and limitations of truly free options like Cash App Taxes and Chime • Why TaxSlayer can be a solid choice for student loan borrowers, landlords, and side hustlers • What investors and crypto traders need to know about brokerage imports and the new 1099-DA form • Why filing taxes is mostly data entry and where real tax planning can make a difference • Simple tools to track mileage, expenses, and side hustle income without losing your mind Bottom line: the best software isn't universal. It's the one that fits your situation without surprise fees. Gold, Silver, and Crypto: What the Drop Means: • Why assets without earnings (like gold and many cryptocurrencies) can swing wildly • The danger of investing based on FOMO instead of a plan • How concentration risk increases the range of possible outcomes, both good and bad • Why short term volatility doesn't automatically change a long term strategy • The risks of misinformation, including AI generated financial advice that isn't real OG walks through how disciplined investors think during volatile moments: zoom out, revisit your allocation, and stick to your strategy instead of reacting emotionally. The Big Takeaway: Whether you're picking tax software or deciding what to do during a market drop, the lesson is the same. Choose tools that fit your life. Build a plan before the chaos hits. Don't let headlines or shiny objects hijack your strategy. This Episode Is For You If: • You're trying to pick tax software without getting ripped off • Markets are making you nervous and you're not sure if you should do something • You want to understand what's happening with gold and crypto without the hype • You're looking for calm, practical guidance during a chaotic time • You believe steady wealth beats chasing shiny things Let's Hear From You: What tax software are you using this year and why? When markets get volatile, what helps you stay disciplined? Share your thoughts in the Spotify comments or The Basement Facebook group. Your experience might help another Stacker avoid an expensive mistake. FULL SHOW NOTES: https://stackingbenjamins.com/the-best-tax-software-2026-robert-farrington-1805 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think building seven figure wealth requires exotic investments or perfect timing? This President's Day episode from Joe's mom's basement tells a very different story. Joe Saul-Sehy, OG, and Neighbor Doug dig into a Kiplinger My First Million case study featuring a Wisconsin couple who started saving at age 32 with exactly zero invested and quietly built $2 million over the next 22 years using mostly retirement accounts and steady habits. Their success sparks a bigger conversation about why simple strategies often outperform complicated ones, and how surviving the boring middle is where wealth is created. Along the way, the gang tackles advisor fees, the psychology of enough, long term care decisions, and the real value financial professionals can bring. Of course, it wouldn't be a basement episode without trivia, community wins, and a few unexpected detours (including a conversation about giant toilet paper rolls that somehow reinforces the episode's central theme). What You'll Take Away: • Why ordinary retirement accounts (401(k)s, SEP IRAs, and Roth IRAs) can be enough to build significant wealth without chasing complex investments • How starting with just enough to earn the employer match creates momentum without overwhelming new savers • A simple escalation strategy: increasing contributions by 1% each year to grow savings almost painlessly • The often missed detail of contributing through the final paycheck to capture the full employer match • A creative gamification approach to Roth contributions tied to the Social Security wage base • How reframing long goals into months instead of years helps investors stay motivated during the long, quiet middle stretch • Why imperfect plans with higher fees can still beat waiting for the perfect investing setup • The real concerns people have about trusting workplace retirement plans and how those plans actually function • Lessons the featured couple learned, including the value of post tax flexibility later in life • Long term care planning as risk management, including balancing insurance coverage with self funding strategies Big Behavioral Conversations: • A TikTok minute featuring Dr. John Delony sparks a discussion about defining enough and whether chasing more success is driven by purpose or ego • How redefining success can shift financial decisions more than any spreadsheet ever will • The danger of constantly moving financial goalposts once progress begins Listener Mailbag: When Is a 1% Advisor Fee Worth It? OG walks through how to evaluate an advisor relationship beyond performance numbers, including whether your advisor helps you make money or avoid costly mistakes, the value of saved time and reduced stress, planning continuity for spouses or heirs, typical fee structures, and how to have an honest fee conversation without damaging a long standing relationship. This Episode Is For You If: • You're behind on saving and worried you've missed your window • You feel like wealth building requires strategies you don't understand • You want proof that simple plans work if you stick with them • You're wondering if your advisor's fee is worth it or if you should manage it yourself • You need reassurance that boring and consistent beats exciting and complicated This episode is a reminder that wealth rarely comes from brilliance or shortcuts. More often, it comes from steady decisions repeated consistently while everyone else searches for something more exciting. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-make-a-million-after-starting-late-1804 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Nothing says romance like a heated debate about the 4% rule. Live from the basement (which suspiciously resembles YouTube headquarters), Joe Saul-Sehy, OG, Neighbor Doug, and the panel celebrate Valentine's Day weekend the only way Stackers know how: by putting their favorite financial ideas on the hot seat. This isn't a polite discussion. It's a rapid fire "love it or leave it" showdown where popular money strategies either get roses or get shown the door. On the chopping block: Paying off a low interest mortgage early: financial freedom or opportunity cost disaster? The FIRE movement: empowering clarity or accidental misery? Lifestyle inflation: natural evolution or silent wealth killer? Real estate as passive income: dream scenario or second job in disguise? The 4% rule: reliable rule of thumb or outdated security blanket? Budgeting apps: behavior changer or digital guilt machine? Expect strong opinions. Expect pushback. Expect OG to bring spreadsheets to a knife fight. Expect Doug to stir the pot. And expect at least one take that makes you argue out loud in your car. Along the way, the crew swaps Valentine's Day plans, reviews survey results from listeners, and throws down in a trivia challenge that could shake up the leaderboard. With margin call rules in play, nobody's position is safe. What You'll Discover: Which popular financial strategies hold up under scrutiny and which ones deserve a breakup Why smart people disagree about mortgage payoff strategies Whether the FIRE movement creates freedom or just different problems The truth about lifestyle inflation and when it's okay versus when it's dangerous Why real estate investing is rarely as passive as it sounds Whether the 4% rule still works or needs serious revision If budgeting apps actually help or just make you feel guilty How to question your own financial assumptions without second guessing everything This Episode Is For You If: You want to understand WHY you believe what you believe about money You're tired of one-size-fits-all financial advice You enjoy hearing smart people debate and disagree respectfully You've been following certain money rules without questioning if they fit YOUR life You believe the most loving thing you can do for your financial plan is challenge it This episode is for anyone who doesn't just want answers but wants to understand the thinking behind them. Because sometimes the most loving thing you can do for your financial plan is break up with strategies that aren't serving you anymore. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's more romantic than roses and chocolate? How about not fighting about money. Joe Saul-Sehy and OG welcome Douglas and Heather Boneparth, the financial planning power couple who literally wrote the book on navigating money in relationships. Broadcasting from the basement (where love is patient and spreadsheets are kind), the crew dives into how people can build financial trust, avoid money secrets, and actually enjoy talking about dollars without it turning into a heavyweight title fight. Whether you're navigating finances with a romantic partner, a roommate splitting rent, an accountability partner keeping you honest, or a family member you're in business with, these principles apply. Because let's face it: our Stacker avatar isn't trying to impress Wall Street. You're trying to build a great life with the people who matter, without money becoming the thing that creates tension. Douglas and Heather break down what healthy financial communication really looks like, how to spot and prevent financial secrecy, and why shared goals matter more than perfectly matched spending styles. They also tackle the tricky stuff: different money upbringings, emotional baggage around finances, and how to reset when conversations go sideways. And since this is the basement, you'll also get practical reminders about key financial deadlines (because nothing kills momentum like IRS penalties), smart ways to teach kids about money, and Doug's festive trivia to keep things light. What You'll Learn: How to talk about money without it escalating into a debate or argument The warning signs of financial secrecy and how to prevent it in any relationship Why shared goals matter more than identical personalities or spending styles Practical ways to align spending, saving, and investing with another person How your childhood money experiences shape your adult financial behavior Smart ways to teach kids patience, work reward connections, and intentional spending Important financial deadlines to keep on your radar Why communication, not math, is often the real key to financial success This Episode Is For You If: You avoid money conversations because they always seem to go badly You're navigating shared finances with a partner, roommate, or family member You want to align financial goals with someone without constant friction You're single but have accountability partners or friends you talk money with You believe better communication is the key to better financial outcomes Question for You: What's one money conversation that felt awkward at first but ultimately made a relationship (romantic, friendship, or otherwise) stronger? Drop your answer in the Spotify comments or the Stacking Benjamins Facebook group. You might just help another Stacker start a better conversation. Because in the end, mastering money isn't just about returns. It's about building a life and relationships that work. FULL SHOW NOTES: https://stackingbenjamins.com/relationships-and-money-with-doug-and-heather-boneparth-1802 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe Saul-Sehy, OG, and Neighbor Doug pull up a rickety basement chair and unpack a growing trend: people treating investing like a series of high stakes bets instead of a long term plan. Sparked by a recent Wall Street Journal piece on aggressive investing, the gang digs into where the line is between smart risk taking and straight up gambling with your future. Using plenty of real world examples and a few basement metaphors, the crew breaks down how stocks, businesses, options, and even so-called innovative products can fall into very different categories depending on why you're using them. The key theme? Good investing isn't about being bold. It's about understanding probabilities, controlling what you can, and stacking the odds in your favor over time. Along the way, the team also tackles listener questions, including some strong feelings about Costco (because of course), and shines a flashlight into the dark corners of complex products like Indexed Universal Life insurance, explaining why "sounds sophisticated" doesn't always mean "fits your plan." If markets feel noisy, confusing, or a little unhinged right now, this episode is your reminder that boring, disciplined strategies still win, and that you don't need to bet the farm to build one. What You'll Learn: • Why so many investors are confusing betting with investing right now • How to tell the difference between calculated risk and speculation • Why understanding probability matters more than chasing big wins • Where options, businesses, and alternative investments can fit and where they often don't • The hidden risks behind complex products like Indexed Universal Life (IUL) policies • Why compounding beats hype even when headlines say otherwise • How small, consistent decisions quietly outperform flashy moves • Yes, what Costco has to do with smart money choices This Episode Is For You If: • Markets feel confusing and you're not sure if you're investing or just guessing • You've been tempted by strategies that sound sophisticated but feel risky • You want to understand the line between smart risk and gambling • You're tired of flashy investment advice and want clarity on what actually works • You need reassurance that boring, disciplined strategies still win Question for You: What's the riskiest financial move you've ever considered, and what stopped you (or didn't)? Share your answer in the Spotify comments or the Stacking Benjamins Facebook group. Bonus points if hindsight made you laugh or wince. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Eighteen hundred episodes calls for something special, and what better way to celebrate than by dragging the absolute worst money advice into the light and laughing at it together? Special guest and CFP Sarah Catherine Guiterrez from Aptus Financial joins Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) for a rapid-fire, no mercy takedown of the most damaging financial clichés ever passed down at family dinners, car dealerships, and internet comment sections. This episode is equal parts group therapy, myth-busting, and friendly argument. Exactly the kind of chaos that's kept the Stacking Benjamins basement standing for 1,800 shows. What You'll Hear in This Milestone Episode: • The most cringeworthy financial advice the panel has ever heard and why it sticks around • Why phrases like "just let the bank take it" quietly wreck long-term wealth • How YOLO thinking sneaks into financial decisions disguised as confidence • The difference between common advice and useful advice • Sarah Catherine's planner level perspective on why bad advice feels comforting • Paula and Jesse sparring over long term thinking versus short term emotion • OG bringing strategy, clarity, and the occasional eye roll • Neighbor Doug doing what he does best: poking holes, cracking jokes, and keeping everyone honest • Why car buying advice is one of the most misunderstood areas in personal finance • How trivia, travel, and history collide in a surprisingly competitive game segment • What Singapore's founding teaches us about perspective, patience, and getting the facts right • Why smart money decisions usually sound boring but work anyway This Episode Is For You If: • You've ever heard money advice and thought, "Wait, people actually believe that?" • You're tired of conflicting financial wisdom and want validation that some of it IS terrible • You've been burned by advice that sounded good but cost you money • You want to hear smart people argue about what actually works versus what just sounds good • You've been with us since episode 1, or just wandered into the basement and want to celebrate This episode is a love letter to Stackers who question conventional wisdom and trust their gut when advice doesn't add up. It's loud, opinionated, funny, and packed with reminders that the best financial moves often start by ignoring the advice everyone else is shouting. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Whitney Elkins-Hutten's story isn't about overnight success or getting lucky. It's about building a wealth machine that keeps working even when life throws curveballs. Broadcast as always from Joe's mom's basement, this episode explores how Whitney went from a modest, very 1970s upbringing to creating systems that generate lasting wealth, and what everyday people can realistically take from her experience. Yes, she built an $800 million real estate portfolio, but this conversation is about something bigger: how to create income systems that compound, scale, and eventually run without you. Along the way, Joe Saul-Sehy, OG, and Doug connect the dots between mindset, cash flow strategies, and protecting what you've already built in a world full of digital landmines. What You'll Take Away: • Why Whitney's early mistakes became her biggest long term advantages • How to think about building cash flow engines, not just accumulating assets • The difference between owning things and building repeatable income systems • Why passive income still requires intentional structure and where people go wrong • How mentorship accelerates progress and what to look for in the right mentor • Practical ways to get started building wealth systems without massive capital • Why diversification across income streams matters more than most people realize • What unexpected businesses like car washes teach us about operational efficiency • How subscription models and recurring revenue quietly stabilize cash flow • The long game of turning short term decisions into generational wealth • Why protecting your personal data is now part of protecting your net worth • How small habits (financial and otherwise) compound into outsized results This Episode Is For You If: • You want to build wealth that lasts beyond your lifetime • You're curious about creating income systems that don't require your constant attention • You're tired of overnight success stories and want the real trajectory • You're looking for principles that work whether you invest in real estate, businesses, or other assets • You believe smart systems and consistent learning can change your family's financial future This episode is for Stackers who want proof that progress doesn't require perfection, and that building the right wealth machine can change the entire trajectory of your financial life and your family's future. FULL SHOW NOTES: https://stackingbenjamins.com/building-generational-wealth-with-whitney-elkins-hutten-1799 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Taxes don't have to feel like something that happens to you. Joe Saul-Sehy, OG, and Neighbor Doug break down the biggest recent tax changes and, more importantly, how to use them intentionally instead of accidentally leaving money on the table. This isn't about memorizing the tax code or becoming a DIY CPA. It's about understanding where the real opportunities are right now, which moves matter most at different life stages, and how smart planning today can quietly add up to thousands of dollars over time. From new deductions to retirement-focused strategies, this episode helps you move from reacting at tax time to planning all year long. What You'll Learn: • The most important recent tax changes and who actually benefits from them • How the expanded SALT deduction works and when it matters • What the new senior deduction could mean for retirees and near retirees • Why maximizing retirement accounts isn't just about saving for later but lowering taxes now • How Health Savings Accounts create one of the most powerful tax advantages available • When tax loss harvesting helps and when it's mostly noise • Why managing your tax bracket in retirement can be as important as investment returns • Smarter charitable giving strategies that align generosity with tax efficiency • How education savings tools fit into a broader tax plan for those who need them • Common tax season mistakes that quietly cost people money every year This Episode Is For You If: • You suspect you're paying more in taxes than you should • Tax planning feels overwhelming so you just deal with it in April • You want to understand which tax moves actually matter at your life stage • You're tired of hearing about strategies that don't apply to your situation • You're ready to stop reacting to taxes and start planning for them This episode is for anyone who wants their tax strategy to support their bigger financial goals, not work against them. If you're looking to keep more of what you earn and make fewer "wish I'd known that earlier" decisions, this is one to queue up. FULL SHOW NOTES: https://stackingbenjamins.com/tax_planning_moves_for_2026-1798 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if the path to better money decisions, more confidence, and a calmer life wasn't a massive overhaul but just getting a tiny bit better today than you were yesterday? Joe Saul-Sehy, Neighbor Doug, OG, and Paula Pant (Afford Anything) are joined by David Gillis, creator of the 1% Better Conference, for a roundtable exploring the surprisingly powerful idea of improving by just 1% at a time. No vision boards. No 5 a.m. ice baths. Just small, intentional choices that compound into real results, financially and otherwise. David brings practical insight and zero guru energy into what sustainable improvement looks like. Together the group talks about why most people burn out trying to change everything at once, and how Stackers can instead design days that make better decisions easier. You'll hear honest conversations about energy drainers (including the ones we pretend aren't draining), why saying "no" is often the most underrated financial skill, and how rest, relationships, and even boredom play a bigger role in success than grinding ever will. There's also a healthy reminder that progress doesn't always look productive, and that's okay. As always, Doug brings the trivia, the basement brings the banter, and the lesson sneaks up on you when you're not looking. If you've ever felt like you should be doing more but don't want to torch your sanity getting there, this episode is for you. If the 1% Better philosophy resonates with you, the 1% Better Conference is happening February 21-22 in Omaha, where Joe will be the keynote speaker. What You'll Learn: Why 1% better beats "start over Monday" every single time How to identify the biggest energy leaks hurting your money decisions Why learning to say "no" can improve your finances immediately How rest, nature, and relationships quietly boost long term success Why small habits matter more than motivation How to grow personally and financially without burning out A realistic framework for steady improvement that fits real life This Episode Is For You If: You're exhausted from trying to overhaul everything at once You feel like you should be doing more but you're already maxed out You want progress that doesn't require torching your current life You're tired of all or nothing approaches that leave you burnt out You're ready for sustainable improvement instead of another failed fresh start Question for You: What's one small change you could make this week that would make your life or money just a little easier? Drop it in the comments or share it with us in the Basement Facebook group. We promise not to turn it into a 30 day challenge with a workbook. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Where do great ideas come from, and why do they always show up in the shower, on a walk, or five minutes after you've stopped trying so hard? Joe Saul-Sehy, OG, and Neighbor Doug welcome this week's mentor, behavioral scientist George Newman, to unpack how creativity really works and how Stackers can use it to make better decisions with money, careers, and life. This isn't about becoming "more creative" in a woo-woo sense. It's about understanding the conditions that consistently produce better ideas. George explains why your best thinking doesn't come from grinding harder but from combining curiosity, expertise, and space to think. The crew digs into why incremental improvement (the famous "1% better" mindset) often beats chasing giant breakthroughs, and how that approach applies just as well to financial planning as it does to business, habits, or personal growth. You'll also hear why surveying the landscape before acting leads to smarter money moves, how relaxing your brain can unlock solutions you didn't know you had, and why most people already have access to better ideas but don't recognize them yet. Whether you're trying to improve your finances, rethink your career, or simply stop overthinking every decision, this episode gives you a practical framework for generating smarter ideas without burning yourself out. What You'll Learn: Where great ideas are most likely to come from (hint: not when you're stressed) Why expertise plus curiosity beats raw inspiration every time How the 1% better philosophy creates long term breakthroughs The role relaxation plays in clearer thinking and decision making Why surveying your options first leads to better financial outcomes How small experiments like paper trading improve confidence before real world action Why coaching, reflection, and time horizons matter more than quick wins This Episode Is For You If: You feel like you're working harder but not thinking better Your best ideas come when you're NOT trying to force them You're exhausted from grinding and want a smarter approach You want to improve your finances but feel stuck in the same patterns You're ready to stop chasing breakthroughs and start making steady progress Questions to Think About: When do your best ideas usually show up, and what are you doing when they arrive? What's one area of your finances that could improve with a "1% better" mindset? Drop your answers in the comments or the Basement Facebook group because George's framework for generating better ideas might shift how you approach everything. FULL SHOW NOTES: https://stackingbenjamins.com/where-do-your-best-ideas-come-from-1796 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever made a money move that felt right then immediately wondered if you just emotionally invested in a bad idea? We've all done it. Some of us have receipts. Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the trickiest parts of personal finance: knowing when to trust your gut and when your gut needs to sit down and let the math speak. Because here's the thing. Most Stackers aren't struggling because they don't know what a Roth IRA is. You're struggling because real life decisions don't happen in a spreadsheet. They happen in the middle of a busy Tuesday, with a dozen tabs open in your brain and a million little "what ifs" fighting for attention. So the guys dig into how intuition works (and when it betrays you), and why data is powerful until you start using it to talk yourself into doing something dumb with extra steps. You'll also hear how the best financial plans aren't built on perfect predictions but on repeatable decisions. Plus the episode veers into some surprisingly useful territory with Costco membership strategy, the hidden psychology of "good deals," and how advisors use tools to help optimize Social Security choices without making you feel like you need a PhD in government paperwork. What You'll Learn: How to tell the difference between good intuition and financial anxiety in a trench coat Why data can be a superpower or a weapon you use against yourself The role of AI and research in decision making and what it means for everyday people How OG thinks about sticking to a plan when emotions get loud Why "a deal" can be a budget win or a trap door What a Costco membership is really doing to your spending habits The Social Security optimization tools advisors use and why timing decisions matter This Episode Is For You If: You've made emotional money decisions you later regretted You either overthink every financial choice or jump too fast without enough info You're not sure when to trust your instincts versus when to run the numbers You want to make confident decisions without needing perfect information You're tired of second guessing yourself every time money is involved Questions to Think About: When was the last time your gut feeling saved you financially or cost you money? Are you more likely to overthink decisions with too much research or jump too fast without enough? Drop your answers in the comments or the Basement Facebook group because finding your balance between intuition and data might be the unlock you need. FULL SHOW NOTES: https://stackingbenjamins.com/should-you-trust-your-gut-or-data-1795 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Inflation may be doing its best to body slam your budget, but this episode is all about fighting back without turning your life into a sad spreadsheet. Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) are joined by special guest Justin Brown-Woods (Price of Avocado Toast) for a roundtable tackling the big question Stackers keep asking: Why does life feel so expensive even when I'm doing everything right? Instead of the usual "just cut lattes" advice, the crew digs into what's really happening. How to calm chaotic expenses. How to stop getting ambushed by "random" costs that aren't random. How to build a plan that makes your money feel predictable again. The conversation hits the real pressure points: food, housing, subscriptions, and the sneaky spending that doesn't look dangerous until it adds up. If you've ever looked at your bank account and thought "Wait, where did that go?" this episode will help you spot the leaks, tighten the system, and still enjoy your life while you do it. What You'll Learn: • How to stop chaotic expenses from wrecking your month • The difference between fixed and variable spending, and why it matters more than you think • Practical ways to lower food costs without eating sadness for dinner • Why housing is the heavyweight champion of your budget and what to do about it • How subscriptions quietly drain cash even when you barely use them • The best way to cut costs without feeling punished • Why mandatory expenses are often more negotiable than you've been told This Episode Is For You If: • You feel like you're doing everything right but still barely keeping up • Your bank account keeps surprising you with where the money goes • You're tired of frugality advice that makes life feel like punishment • You want to cut costs without giving up everything that makes life worth living • You're ready to calm the chaos and make your spending feel predictable again Questions to Think About: What's one expense that used to feel normal but now feels completely ridiculous? Which category gets you more: food spending, housing, or the sneaky monthly subscriptions? Drop your answers in the comments or the Basement Facebook group because this roundtable's framework for taming chaotic spending might be exactly what you need. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-afford-the-new-normal-1794 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if your money stopped dictating your schedule and started supporting the life you actually want to live? Joe Saul-Sehy welcomes CFP Dana Anspach of Sensible Money as special guest co-host for an episode featuring this week's mentor, Andy Hill. Andy shares how he stepped away from the corporate grind, redesigned his priorities, and built a life where family and flexibility came first. His story isn't about escaping work. It's about building a financial foundation that gives you options. Then the conversation shifts to a headline that caught everyone's attention: NASCAR driver Kyle Busch and his wife Samantha are suing their insurance company, calling the life insurance they purchased "a scam." Dana uses this case to break down one of the most misunderstood areas in personal finance: life insurance. From Indexed Universal Life (IUL) policies to knowing when insurance is a tool and when it's a distraction, she shows how clarity of goals should drive every decision and how to avoid the traps that caught even high earners like the Buschs. The episode also touches on estate planning, scams to watch out for, how young adults should think about budgeting and debt, and how to evaluate whether paying off loans or investing is the better move for your situation. It connects the dots between time freedom, smart planning, and protecting what you're building. What You'll Learn: • How to design your finances around the life you want, not just the paycheck you earn • What "owning your time" really means and how to start moving in that direction • Why your financial plan should begin with values and priorities, not products • How to think about entrepreneurship without blowing up your financial stability • What the Kyle Busch insurance lawsuit reveals about life insurance products and sales tactics • The truth about Indexed Universal Life insurance and when it may or may not make sense • How to evaluate life insurance based on goals instead of sales pitches • How estate planning protects your family and your legacy • The pros and cons of paying off loans versus investing • Budgeting principles that help young adults build strong money habits early • How to recognize and avoid financial scams (including insurance product traps) • Why celebrating progress matters just as much as setting the next goal This Episode Is For You If: • You feel like your money controls your life instead of supporting it • You want more flexibility and time freedom but don't know how to fund it • You're confused about whether life insurance products are helping or just costing you (especially after hearing about the Busch lawsuit) • You're trying to figure out the right order of financial moves (debt vs investing, insurance vs saving) • You want your financial plan to reflect your actual values, not just what you're "supposed" to do This episode is about aligning your money with your life. If you're ready to stop reacting to your finances and start using them to build more freedom, flexibility, and confidence, this one belongs at the top of your queue. FULL SHOW NOTES: https://stackingbenjamins.com/own-your-time-with-andy-hill-and-dana-anspach-1793 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like your money questions don't fit neatly into one category? One minute you're thinking about retirement, the next it's insurance, emergency funds, gifting money, or whether your workplace plan is helping or hurting you. This is one of those episodes where Stackers bring the real-life questions, and Joe Saul-Sehy, CFP Anna Allem, and Neighbor Doug help sort through the noise. It's a true Q&A show built from the issues you're wrestling with right now. No perfect spreadsheets. No one-size-fits-all answers. Just practical guidance for making smart decisions when your financial life has a lot of moving parts. You'll hear how to prioritize when everything feels important, how to adjust your strategy as rules change, and how to stay flexible without losing control of your long-term plan. College planning comes up, but it's part of a bigger conversation about balancing competing goals, not the center of the episode. What You'll Learn: • How to make better decisions when multiple financial priorities collide • Smarter ways to think about life insurance when cash flow feels tight • How to build or rebuild an emergency fund with inconsistent income • What changes to 401(k) rules could mean for your saving and investing strategy • When opting out of a workplace plan might make sense, and when it's a mistake • How automatic enrollment and contribution changes can impact your future wealth • The right way to gift money to kids or grandkids without creating tax or planning problems • How HSAs fit into your bigger financial picture • Why financial gridlock happens and how to break through it • How to balance short term flexibility with long term security • A clear explanation of FAFSA and financial aid, and how it fits into overall planning for families who need it This Episode Is For You If: • You're juggling multiple financial priorities and not sure which one to tackle first • You feel stuck because everything seems important and nothing feels urgent enough • You want guidance that fits your messy real life, not just textbook answers • You're tired of financial advice that assumes you only have one problem at a time • You need permission to prioritize imperfectly and still make progress If your finances feel like a maze, this is your map. FULL SHOW NOTES: https://stackingbenjamins.com/answering-stacker-questions-with-anna-allem-1792 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Some people kick off a new year with a vision board. We prefer a runway show in sweatpants from Joe's mom's basement. Joe Saul-Sehy, OG, and Neighbor Doug throw personal finance into the spotlight and ask the question every Stacker secretly loves: What's officially "so last year" in your money plan, and what's worth keeping for 2026? Because here's the truth. You don't need a total financial makeover. You need a few smart "wardrobe swaps" that fit your real life. The habits that quietly drain your progress (hello, lifestyle creep). The stuff people obsess over that doesn't matter as much as they think. And the overlooked moves that make everything else easier. The crew breaks down what's out (financial habits that looked good but never delivered), what's in (the practical moves that reduce stress and create actual progress), and why real financial planning isn't just about investments but about building a system that holds up when life gets messy. Also on the docket: a fresh start to the yearlong trivia competition with new rules, new twists, and the kind of competitive energy that makes you wonder if the trophy comes with a safety warning label. What You'll Learn: • What financial trends are out for 2026 and why they weren't helping anyway • The habits that are in if you want more freedom, less stress, and fewer "where did my money go" moments • Why real financial planning isn't just investments but a system that works in real life • How lifestyle creep sneaks in and a couple ways to stop it before it becomes your full-time hobby • What tax strategy means for normal people, not just spreadsheet enthusiasts • The money conversations you should have early in the year before life gets loud again • A realistic take on housing in 2026 and what to focus on when markets don't behave • New trivia rules including a twist that changes everything if you're not paying attention This Episode Is For You If: • You want to know what to stop doing so you can focus on what works • You're tired of financial advice that adds more tasks instead of clarity • You suspect some of your money habits aren't pulling their weight • You want permission to quit the financial trends that never fit your life • You're ready for a few strategic changes that make 2026 feel more manageable Questions to Think About: What's one money habit you're officially retiring in 2026? If you could upgrade one part of your financial plan this year, what would it be: spending, saving, investing, insurance, or taxes? Drop your answers in the comments or the Basement Facebook group because this episode is all about figuring out what stays and what goes. FULL SHOW NOTES: https://stackingbenjamins.com/finance-hot-or-not-2026-1791 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you're making decent money but still feel like you're one bad month away from stress, this episode is for you. Joe Saul-Sehy, OG, and Neighbor Doug sit down with Mel Abraham to talk about something most Stackers think about but don't know how to start: creating income that doesn't depend entirely on showing up to work every single day. Not side hustle mania or get-rich-quick schemes. Just practical ways to build what Mel calls a "money engine" that makes your financial life steadier and way less stressful. Mel breaks down the different types of income streams, how they fit into real life (not just theory), and where to start if you're tired of feeling like your paycheck is the only thing keeping everything afloat. The goal isn't to quit your job tomorrow. It's to create options and breathing room so one surprise expense or career hiccup doesn't derail everything you've built. Then Joe and OG tackle the January financial to-do lists that flood your inbox every year. You know the ones: "15 money moves to make before February!" They separate what's worth your time from what's just financial busywork designed to make you feel productive without moving the needle. Because here's the truth. You don't need more financial homework. You need a few strategic moves that make 2026 feel more manageable from the start. What You'll Walk Away With: • How to think about building income beyond your paycheck without burning out • The different types of income streams and which ones fit your actual life right now • Where to start creating assets that work even when you're not clocking in • Which January money tasks are worth doing and which ones waste your time • How to prioritize your financial checklist for maximum impact with minimum stress • Simple ways to organize your money for the year without it becoming a second job This Episode Is For You If: • You're making decent money but still feel financially stressed • You want options beyond your paycheck but don't know where to start • You're tired of feeling like everything depends on your next paycheck • January financial advice usually overwhelms you more than it helps • You want systems that reduce anxiety, not add more tasks to your list Before You Hit Play, Ask Yourself: What's one income stream you'd love to build if you knew it wouldn't be complicated? If you only had one hour this month to improve your finances, what would you spend it on? Drop your answers in the comments or the Basement Facebook group because Mel's framework plus Joe and OG's January reality check might be exactly what you need to start the year without the usual stress. FULL SHOW NOTES: https://stackingbenjamins.com/build-your-money-engine-mel-abraham-1790 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if some of the "rules" you've been told about money aren't rules at all, just assumptions that haven't been questioned lately? Joe Saul-Sehy, OG, and Neighbor Doug pull apart a handful of deeply held financial beliefs and see what holds up when real life enters the conversation. From Social Security timing to investment return expectations, the crew explores where common advice works, where it falls short, and why context matters more than catchy rules of thumb. Along the way, the discussion shifts from spreadsheets to behavior, because knowing what to do is one thing and doing it (especially in retirement) is another. The team talks through spending realities, inflation anxiety, and how small mindset shifts can make your plan feel less fragile and more livable. Then, just when things get serious, Doug introduces a challenge that's equal parts practical and revealing. The Survivor Pantry. It's a simple idea that uncovers how prepared (or not) we really are, and why preparedness isn't about fear but flexibility. In This Episode You'll Explore: • Why popular Social Security advice isn't one size fits all • What real world investment returns look like over time • How behavioral blind spots can derail otherwise solid plans • The difference between planning for retirement and living in it • Smarter ways to think about spending as prices change • Why some financial myths refuse to die (and how to spot them) • What the Survivor Pantry reveals about readiness and resilience • How questioning assumptions can lead to calmer, more confident decisions This episode is less about finding new answers and more about asking better questions, especially if you're tired of feeling like you're "behind" for not following every money rule to the letter. Conversation Starter for the Basement: What's one money belief you've always accepted but now you're not so sure about? Drop your thoughts in the Facebook group or comments and compare notes with other Stackers who are rethinking the playbook right alongside you. FULL SHOW NOTES: https://stackingbenjamins.com/challenging-money-assumptions-1789 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

It's that time of year when we look ahead, squint confidently into the future, and pretend we have any idea what's coming next. In this annual Stacking Benjamins tradition, Joe Saul-Sehy welcomes back Mindy Jensen from the BiggerPockets Money Podcast, Len Penzo of LenPenzo.com, and OG for the predictions episode that blends money talk, pop culture, and just enough nonsense to keep everyone honest. Instead of pretending anyone can forecast the markets, the crew leans into what really matters: how to think about uncertainty. With help from a Magic 8 Ball (clearly the most reliable forecasting tool available), the panel throws out bold guesses about stocks, crypto, AI, inflation, interest rates, and the kinds of headlines that will dominate conversations in 2026. Some predictions are financial. Some are cultural. Some are optimistic, let's say. But beneath the fun is a useful reminder for Stackers. Predictions don't build wealth, process does. This episode isn't about acting on guesses. It's about stress-testing assumptions, questioning narratives, and remembering that long-term success comes from good habits, not crystal balls. If you've ever wondered how much attention to pay to forecasts (and how much to ignore), this conversation delivers clarity wrapped in entertainment. And yes, there are sports predictions, celebrity guesses, and enough wild speculation to guarantee at least a few laughs when we look back a year from now. In This Episode You'll Hear: The crew's biggest financial and cultural predictions for 2026 What the Magic 8 Ball "thinks" about markets, rates, and inflation Why forecasts are fun but dangerous if taken too seriously Thoughts on AI, energy use, and how technology may affect daily life Predictions about crypto, gold, and the stories investors love to chase A reminder of what matters when markets surprise everyone Sports, pop culture, and wildly specific guesses that will age somehow Join the Conversation: Which prediction do you think has the best chance of being right, and which one will age the worst? Share your take in Spotify comments or the Basement Facebook group so we can revisit it next year and keep receipts. This episode is a reminder that while nobody knows what 2026 will bring, Stackers who stay curious, flexible, and grounded tend to do just fine. Magic 8 Ball or not. FULL SHOW NOTES: https://www.stackingbenjamins.com/magic-8-ball-and-2026-predictions-1788/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If 2026 already feels busy and it's barely started, you're not imagining it. Joe Saul-Sehy and OG sit down with renowned time management expert Laura Vanderkam to tackle one of the biggest stressors Stackers face. Feeling like there's never enough time to do the things that matter, including managing money well. Laura helps break the myth that better time management means squeezing more productivity into already packed days. Instead, the conversation centers on intentional time use: how to protect space for what matters most, reduce decision fatigue, and build simple systems that make life (and money) feel lighter. If you've ever said "I don't have time to deal with this right now" about your finances, this discussion will feel uncomfortably familiar in a good way. From there, the show zooms out just enough to connect time decisions to money decisions. Joe and OG explore why financial stress often comes from neglect rather than bad choices, and how a few well-timed actions (like organizing documents, planning ahead for aging parents, or setting aside focused "money time") can prevent massive headaches later. No doom and gloom economics here, just a reminder that uncertainty is always around and preparation beats prediction every time. The episode also takes a thoughtful turn toward caregiving and elder planning, a topic many Stackers are quietly juggling while managing careers, kids, and their own goals. Laura and the team talk about how planning before a crisis saves not just money but emotional energy, one of the most overlooked resources of all. This is a conversation about doing less reacting, more choosing, and building a 2026 where your calendar and your bank account work together. What You'll Hear: • Why "being busy" isn't the same as using time well • Laura Vanderkam's practical strategies for reclaiming focus and presence • How small pockets of time ("time confetti") quietly drain energy • Simple ways to create space for money decisions without overwhelm • Why procrastinating financial tasks often costs more than bad investing • How to think ahead about caregiving without panic or perfection • What documents and conversations make future decisions easier • How to prepare for uncertainty without obsessing over headlines If you want to start 2026 feeling more in control (not just of your money but of your life), this episode offers a grounded, encouraging roadmap. No hustle culture. No financial fear tactics. Just smart conversations about using your time wisely so your money decisions get easier, not harder. Listen for the moment when "I don't have time" turns into "I'm choosing what matters." FULL SHOW NOTES: https://stackingbenjamins.com/master-your-time-management-with-laura-vanderkam-1787 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

A new year has arrived, and with it comes a fresh wave of hot takes, bold predictions, and "can't miss" investing ideas. Joe Saul-Sehy and OG step back from the noise to discuss what clearly doesn't work and then to focus on what actually helps you build wealth in 2026 and beyond. Rather than chasing hot trends, they revisit the timeless rules that have quietly done the heavy lifting through every market cycle. Why diversification still matters even when it feels boring. Why IPO hype and speculative real estate deals often disappoint. How consistency beats cleverness far more often than most people expect. From there, the conversation shifts into a practical framework Stackers can use no matter what the market throws their way. Joe and OG walk through the proper order of investing decisions: start with clear goals, build the right asset allocation, choose appropriate asset selections, and then layer in tax strategy. By putting taxes in the right place (after the big structural decisions), they explain how to improve outcomes without letting tax avoidance distort the entire plan. The episode also digs into real-world traps that tend to surface when uncertainty rises. Real estate crowdfunding. Penny stock temptation. Misunderstood property tax increases. The guys break down where people get tripped up and how to protect yourself without becoming overly cautious or frozen by fear. Just as important, Joe and OG explore the difference between luck and skill in investing stories. If you've ever felt behind because someone else's risky move worked out, this discussion brings perspective and relief by reminding Stackers what sustainable progress actually looks like. What You'll Learn: • Why timeless investing principles matter more than 2026 predictions • How diversification truly reduces risk and where people misuse it • The dangers of IPOs, penny stocks, and "exclusive" real estate deals • The correct order of smart investing decisions: goals first, asset allocation next, asset selection after that, tax strategy layered on last • How to think about tax efficiency without letting taxes drive the plan • What new homeowners often misunderstand about property taxes • How to spot luck masquerading as skill in investing success stories • Ways to stay confident and consistent when markets feel uncertain If you're looking to start 2026 grounded, informed, and focused on the moves that actually matter, this episode delivers a steady, practical roadmap without hype, fear, or shortcuts. Listen for the principles that hold up when markets misbehave and the small mistakes that quietly derail otherwise solid plans. FULL SHOW NOTES: https://stackingbenjamins.com/real-estate-scam-companies-1786 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if earning more money in 2025 has less to do with working longer hours and more to do with becoming dangerously useful? In this conversation, Joe Saul-Sehy and OG sit down with entrepreneur Alex Hormozi to break down how skill stacking, leverage, and better decision-making can radically change your income trajectory, whether you run a business, lead a team, or clock in for a 9-to-5. Alex pulls back the curtain on what actually drives higher pay: choosing the right skills, focusing on work that compounds, and learning how to take smart risks without blowing up your life. Along the way, he tackles one of the hardest challenges Stackers face, how to pursue growth when well-meaning friends, family, or coworkers are urging you to play it safe. This isn't about hustle culture or quitting your job tomorrow. It's about building a skill set that makes you indispensable, learning how to negotiate from a position of strength, and thinking long-term while others stay stuck optimizing small things. WHAT YOU'LL TAKE AWAY: Why skill stacking beats talent when it comes to earning power How to identify high-leverage skills that pay off in any career Ways to invest in yourself that don't require an MBA or massive risk How to apply entrepreneurial thinking inside a traditional job Practical negotiation insights that actually work in the real world When giving away value helps you grow and when it backfires How to tune out discouraging advice without burning bridges Why systems and processes matter more than motivation If you're serious about earning more in 2025 but want to do it thoughtfully, sustainably, and on your own terms, this episode gives you a blueprint worth studying. Listen for the mindset shifts that compound quietly and the small changes that can unlock much bigger opportunities over time. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if the biggest driver of your financial future isn't the stock market but your skill set? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and the crew sit down with entrepreneur and business strategist Alex Hormozi to unpack one of the most overlooked wealth-building tools Stackers have access to: skill acquisition. Alex doesn't pitch get-rich-quick nonsense or risky moonshots. Instead, he walks through how ordinary people (employees, side hustlers, and business owners alike) can increase their income by focusing on high-leverage skills, smarter negotiations, and taking calculated risks that actually make sense. You'll hear how Alex went through early business struggles and hard-earned lessons before building real wealth. Not by chasing trends, but by deliberately stacking skills, learning faster than the competition, and betting on himself without blowing up his life. The lessons apply whether you're asking for a raise, switching careers, growing a side hustle, or simply trying to earn more without working yourself into the ground. This is an episode about earning more on purpose, not grinding harder. WHAT TO LISTEN FOR: Why skill-building often beats investing early in your career How to identify high-leverage skills that pay off repeatedly The difference between smart risk and reckless risk Why small optimizations won't change your life but big skills might How to design your own curriculum without going back to school When betting on yourself actually makes financial sense ALSO IN THIS EPISODE: Reflecting on standout episodes from 2025 and what's coming next, a quick check-in on managing your money with intention not noise, why confidence is built through reps not motivation, and how compensation and risk are more connected than you think. A QUESTION FOR THE BASEMENT: What's one skill you've learned that's paid off way more than you expected, or one you wish you'd started earlier? Share it in Spotify comments or bring it to the Basement Facebook group. Your answer might help another Stacker spot their next big opportunity. Because money grows in accounts, but wealth starts with what you can do. Learn more about your ad choices. Visit podcastchoices.com/adchoices

New year, clean slate, and maybe time for a closer look at the person managing your money. Joe Saul-Sehy and OG kick off 2026 by answering the question many Stackers quietly wonder about: Is my financial advisor actually good at their job? Rather than talking theory or credentials, they break down five real-world red flags that signal an advisor might be more focused on products, commissions, or their own ego than on your goals. These are the subtle warning signs you'll never see in a glossy brochure but you'll absolutely feel over time. The 5 red flags: • Poor communication that keeps you in the dark • Office culture that feels off • Confusing jargon (often a feature, not a bug) • Unclear or hidden fees • Products over process Plus: Doug's Italian food trivia, New Year's breakfast burrito chaos, and a reminder that you're allowed to expect clarity and respect. Question for you: What's the biggest green flag or red flag you've seen from a financial advisor? Share in the comments—your story might help another Stacker avoid a costly mistake. The Red Flags Your Financial Advisor Hopes You Miss New year, clean slate, and maybe a closer look at the person helping you manage your money. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG kick off the year by pulling back the curtain on a question many Stackers quietly wonder about: Is my financial advisor actually good at their job? Rather than talking theory or credentials, the guys break down five real-world red flags that signal an advisor might be more focused on products, commissions, or their own ego than on your goals. These are the subtle warning signs you'll never see in a glossy brochure but you'll absolutely feel them over time. From how an advisor communicates (or doesn't), to what their office culture tells you, to why confusing jargon is often a feature not a bug, this episode gives you practical ways to evaluate whether your advisor is truly on your team. And because this is Stacking Benjamins, the serious stuff is balanced with laughs, a little New Year's chaos, and Doug's trivia detour into Italian food. If you've ever wondered whether you should stay, ask better questions, or quietly run for the exit, this episode gives you the confidence to decide. WHAT YOU'LL LEARN: The top five red flags that signal a subpar financial advisor Why great advisors focus on process and goals, not hot products How poor communication quietly sabotages your financial progress What an advisor's office environment and staff behavior can reveal Why unclear fees and excessive jargon should make you nervous How to check public records without feeling overwhelmed ALSO IN THIS EPISODE: A fresh start to the year with breakfast burritos, Doug's trivia break on Italian food, a reminder that you are allowed to expect clarity and respect, plus community updates and what's coming next. HERE'S A QUESTION TO THINK ABOUT: What's the biggest green flag or red flag you've seen from a financial advisor? Share your experience in Spotify comments or bring it to the Basement Facebook group. Your story might help another Stacker avoid a costly mistake. Because the right advisor doesn't just manage money. They help you sleep better at night. Learn more about your ad choices. Visit podcastchoices.com/adchoices

As we close out the year, we're bringing back this powerful 2023 conversation with financial educator Tiffany Aliche (The Budgetnista) because it resonates even more today than when we first aired it. Joe Saul-Sehy and OG sit down with Tiffany for a conversation about financial wholeness. Not just having the right accounts, but building a money life that supports you when life doesn't go as planned. Tiffany shares what the past year taught her about preparedness, community, and resilience after the sudden loss of her husband, and why the systems she had in place mattered more than any single perfect financial move. This isn't a story about fear or worst-case scenarios. It's about confidence, clarity, and giving yourself grace while still doing the work that protects the people you love. Along the way, Joe and OG pull practical lessons every Stacker can use without overwhelm or guilt. The money basics that quietly make everything else easier: beneficiaries, insurance, wills, and the difference between having a plan and having peace of mind. If you've ever wondered whether you're focusing on the right financial priorities, or how prepared you really are, this episode offers reassurance, perspective, and a clear path forward. WHAT YOU'LL TAKE AWAY: What financial wholeness really means beyond budgets and spreadsheets Why having basic systems in place matters more than chasing optimization The quiet power of beneficiaries, insurance, and estate documents How preparation can reduce stress not just financially but emotionally Why community and education are essential parts of a strong money life How to enter a new year with confidence instead of pressure THIS EPISODE IS FOR YOU IF: You've ever wondered whether you're focusing on the right financial priorities, you want to make sure your essentials are covered without overwhelming yourself, you're thinking about what really matters as you head into a new year, or you believe the smartest financial move isn't always doing more but making sure the basics are handled. This is one of those episodes that makes you pause and ask: If something unexpected happened tomorrow, would my money make life easier or harder? You don't need to answer that perfectly today, but it's a great conversation to start. Sometimes the smartest financial move isn't doing more. It's making sure the essentials are handled so you can live fully the rest of the time. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if the biggest upgrade to your finances wasn't a new strategy but a new way of thinking? Joe Saul-Sehy and OG unpack the small but powerful money mindset shifts that separate people who know what to do from people who actually make progress. This isn't about motivation posters or vague positivity. It's about practical mental frameworks that lead to better decisions, fewer regrets, and more confidence with money. The team walks through their top five money mindset tweaks. How to focus on strengths instead of endlessly fixing shortcomings. Why taking action beats overthinking every time. How playing long-term games with the right people changes everything. Along the way, they connect mindset directly to real-world choices, like how thinking clearly about value, longevity, and opportunity cost affects something as everyday as buying a car. That's where Carl Brauer from iSeeCars joins the conversation with insight into which vehicles deliver the best long-term value. It's a perfect case study in mindset-driven money decisions. Not chasing shiny objects, but choosing options that quietly compound in your favor. If you've ever felt like you're doing most things right but not seeing the results you want, this episode helps you zoom out, recalibrate, and move forward with intention. WHAT YOU'LL LEARN: The five mindset shifts that consistently lead to better money outcomes Why progress comes from doing rather than perfecting your plan first How understanding compounding changes the way you view time, effort, and money Why focusing on your strengths beats trying to fix every weakness How to think about purchases like cars through a long-term value lens The power of playing long-term games with people who think the same way THIS EPISODE IS FOR YOU IF: You feel like you know what to do with money but struggle to actually do it, you're tired of motivational content that doesn't translate into real change, you want to understand why some people progress faster with less effort, you're making a big purchase soon and want to think about it more clearly, or you believe the way you think about money matters as much as what you do with it. Sometimes the most profitable move isn't changing your plan. It's changing how you think about the plan. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What separates people who build lasting wealth from people who just chase the next hot investment? David Greene from BiggerPockets has a clear answer, and it's not what most people want to hear. Joe Saul-Sehy and OG revisit a standout 2023 conversation with David that still resonates today. His story isn't about shortcuts, hacks, or getting lucky. It's about skill building, discipline, and learning to turn everyday work into long-term opportunity. From scooping ice cream at Baskin Robbins to building a successful real estate career, David breaks down what actually creates momentum over time and why "passive income" still requires serious intention. This episode showcases the kind of conversation that belongs in the vault. David explains what makes work feel worth it, how to develop skills that compound, and why the unsexy fundamentals matter more than the flashy strategies everyone's talking about. If you're tired of hype and ready for substance, this interview delivers. The show also tackles two critical protection topics. Adam Barowy from UL's Fire Safety Research Institute joins to explain the real (and often overlooked) risks of lithium-ion batteries in e-bikes, scooters, and everyday devices. He shares practical steps every family can take to reduce fire risk without panic or overreaction. Then Joe and OG field a listener question about keeping family property in the family. The discussion explores estate planning tradeoffs, communication challenges, and how to think through shared ownership without creating future conflict. Every segment connects to the same core idea. Building a life that's not only financially strong but resilient, safe, and meaningful. What You'll Walk Away With: • David Greene's framework for building wealth through skill mastery, not investment shortcuts • Why "passive income" is never truly passive and what actually makes work sustainable long term • Practical fire safety guidance for lithium-ion batteries you probably already own in your home • Simple steps to reduce household fire risk based on real research, not fearmongering • Thoughtful estate planning insights for preserving family property across generations • How to think about money not just as growth but as protection and stewardship This Episode Is For You If: • You're tired of wealth-building advice that sounds too good to be true • You want to hear how someone actually built success through discipline and skill development • You've got lithium-ion batteries around the house and never thought twice about fire safety • You're thinking about how to pass property or wealth to the next generation without creating conflict • You believe the smartest money moves involve both growing and protecting what you have Before You Hit Play, Think About This: What's one area of your financial life where you're focused on growth but might need more protection or structure? Share your thoughts in the Spotify comments or bring the discussion into the Basement Facebook group because this episode tends to spark great follow-up conversations. Sometimes the smartest money move isn't about earning more. It's about keeping what you've built safe and aligned with what matters most. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is the constant push to be great quietly making life (and money) harder than it needs to be? This vault-worthy episode from 2023 hits differently, especially during a season when expectations run high and energy can run low. Joe Saul-Sehy is joined by Len Penzo, Paulette Perhach, Diania Merriam, and special guest Stephanie O'Connell Rodriguez for a candid roundtable about ambition, procrastination, perfectionism, and the surprising freedom that comes from choosing good over exhausting. Instead of chasing flawless systems or ideal outcomes, the conversation explores what actually moves the needle in real life. Building momentum. Removing friction. Letting go of the idea that every decision has to be optimized. Whether it's money habits, career goals, or simply getting unstuck, this episode offers a calmer, more sustainable way forward without lowering your standards or your future. Along the way, the group shares personal stories, practical strategies, and a few moments that only happen when smart people stop pretending they've got it all figured out. It's thoughtful, honest, and exactly the kind of perspective many Stackers didn't know they needed. What You'll Take Away from This Episode: • Why perfection often slows progress more than fear or lack of knowledge • How "good enough" can be a powerful financial strategy, not a compromise • Practical ways to break through procrastination without burning out • When delegation and automation actually help and when they just add complexity • How to balance ambition with contentment without feeling like you're settling • Why consistency beats intensity in both money and life Questions Worth Sitting With: Where are you chasing "perfect" when "done" would be better? What would improve immediately if you lowered the bar just a little? Which money habit could become easier if you stopped optimizing it? We'd love to hear your take. Share your thoughts in the Spotify comments or bring the conversation into the Basement Facebook group, especially if this episode gave you permission to ease up without giving up. Sometimes the best financial move isn't pushing harder. It's choosing progress that actually fits your life. This one's a quiet classic, and those tend to age the best. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

One snowy Christmas Eve in Texarkana, Neighbor Doug settled into bed in his snazzy Superman Footie PJs (Amazon affiliate link), still buzzing on Joe’s Mom’s eggnog… Today’s special holiday episode recounts a completely original tale of Doug and the money lessons learned when he’s visited by three ghosts—past, present, and future. Especially when it comes to past credit mistakes, what’s done is done. Whatever method works best for you (debt snowball or debt avalanche), do that one. Come to terms with your bad money habits and realize that you can’t outearn them. It’s on you to fix the bad money habits of your past. Focus on what’s current and fix what needs fixing today. Don’t get caught in the trap of lamenting your past nor only planning for the future. Our only truly limited resource is time. Balance living for today with planning for the future. Remain in the present – especially when spending time with your loved ones – while keeping a vision in mind for your longer-term future plans. Be intentional about your plans and actions today and timeline what you want to achieve in what time you have remaining. Communicate on a regular basis with your “team” (loved ones) about your financial goals, progress, and situation. We recommend scheduling a weekly Family Budget Meeting. Automate as many of your financial decisions as possible today so you never have to think about them again in the future. Commit to paying off that mortgage early, ramp up those retirement savings contributions, stack those Benjamins for your kids’ college savings. Decide where you want to be financially in the future; face reality of where you are currently (we like our sponsor, Monarch Money, to track where you are); and take the necessary step to make that future a near certainty. Remember that time is the one commodity that’s finite for all of us. Value your time and experiences while staying responsible to your present and future self. Remember and learn from the sins of your past to build on your strengths; focus on living in the present and building your financial foundation; and head into the future with more confidence than Joe’s Mom’s Neighbor Doug during the annual Sun’s Out, Guns Out El Camino Competition at the Sizzler. FULL SHOW NOTES: https://stackingbenjamins.com/doug-and-the-three-ghosts-2025-holiday-special-1778 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

It's the most wonderful time of the year in the basement, and we're kicking off the holiday season with our biggest, most packed episode yet. Joe Saul-Sehy, OG, and Neighbor Doug welcome Joel Larsgaard and Matt Altmix from the How to Money podcast for a year-end celebration of everything that mattered in money during 2025. Think of this as the holiday parade of personal finance episodes. There's a lot happening, it's all connected, and you'll want to stick around for the whole thing. First up, Joel and Matt join the crew for their Top 5 Lessons from the Events of 2025. From AI's real impact on everyday work to market surprises nobody saw coming, this segment unpacks the money moments that actually changed how we think about our finances. These aren't just headlines rehashed. They're the insights that'll help you make smarter moves in 2026. Then the show shifts to a fascinating trend everyone's noticing but nobody's quite figured out yet. Why is everyone suddenly betting on everything? Prediction markets are exploding, retail investors are taking bigger risks, and the line between investing and gambling feels blurrier than ever. Joe, OG, Joel, and Matt dig into what's driving this shift, whether it's brilliant or reckless, and how to think about risk when it seems like the whole world just discovered the casino. But wait, there's more. Nick from Alaska calls in with a real-world budgeting challenge that proves even the most prepared Stackers face seasonal money surprises. His situation sparks the kind of practical, helpful conversation this show does best. And because this is a holiday kickoff episode, we're wrapping with big news about the Stacking Benjamins Vault, the new tool designed to help you organize and protect your most important financial documents without the headache. This episode has everything. Big ideas, real questions, legendary guests, surprise calls, and the energy of a show that knows the best episodes are the ones where there's almost too much good stuff to fit in. Welcome to the holiday season, Stacker style. What You'll Walk Away With: • Joel and Matt's Top 5 Money Lessons from 2025 that actually matter going forward • How AI really affected work and income this year in practical, not theoretical, ways • Why prediction markets and betting culture are suddenly everywhere and what it means for investors • Whether the shift toward riskier investments is smart adaptation or dangerous groupthink • Nick from Alaska's budgeting challenge and the solutions the crew offers in real time • An inside look at the Stacking Benjamins Vault and how it helps you organize what matters most • The perfect energy boost heading into holiday episodes and a new year of smarter money moves This Episode Is For You If: • You want the year-end money recap that feels like a celebration, not a lecture • You've noticed everyone's suddenly betting on elections, sports, and markets and wonder what's going on • You love episodes with special guests, surprise calls, and enough happening to keep you engaged the whole way • You want to head into the holidays feeling smarter about money, not more anxious • You're ready to kick off the season with the Stacking Benjamins crew at their absolute best After You Listen, Share This: What was your biggest money lesson from 2025? And have you noticed yourself (or people you know) getting more comfortable with risky bets lately? Drop your thoughts in the Spotify comments or the Basement Facebook group because this episode kicks off our holiday run, and we want to hear what's on your mind heading into 2026. FULL SHOW NOTES: https://stackingbenjamins.com/year-end-lessons-with-the-runners-up-of-the-charity-challenge-1777 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Before you charge into a new year with fresh goals, shiny spreadsheets, and unrealistic optimism, it's worth doing the one thing most people skip. Looking back honestly at what just happened. Joe Saul-Sehy, OG, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) gather for an end-of-year roundtable to unpack the financial, personal, and behavioral lessons that 2025 handed us. Sometimes those lessons arrived gently. Sometimes they shoved us face-first into reality. Either way, this episode isn't about predictions for what's coming. It's about understanding the patterns from what already happened. The team digs into what diversification actually meant this year when some of the old rules stopped working the way they used to. They explore why emotional reactions to headlines still cost investors real money, even when everyone knows better. And they examine how policy noise (tariffs, political drama, market freakouts) reminded us once again that short-term chaos rarely deserves long-term decisions. Along the way, the conversation touches on housing lessons learned, family priorities that got re-examined, and AI's quiet but growing influence on work, productivity, and opportunity. The thread running through it all? Financial planning only works when it serves the life you're trying to build, not the other way around. This episode balances big-picture thinking with real-life reflection. It's the kind of honest look back that actually helps you move forward smarter instead of just louder. What You'll Walk Away With: • The most important financial lessons 2025 taught investors, whether they actually listened or not • How AI quietly changed work, productivity, and opportunity in ways that matter for your money decisions • Why diversification looked different this year and what investment principles still held up under pressure • How market volatility exposed emotional blind spots you might not have known you had (and how to fix them) • What the housing market taught us about patience, expectations, and timing • Why year-end reflection beats year-end predictions every single time • How family dynamics, personal values, and money planning intersect more than anyone likes to admit This Episode Is For You If: • You want to learn from 2025 before setting goals you'll abandon by February • You made some money decisions you're proud of and some you'd rather forget • Market headlines changed your behavior this year and you're wondering if that was smart • You're tired of prediction content and want actual reflection on what already happened • You believe getting smarter about money means being honest about what you got wrong Before You Hit Play, Think About This: What money decision in 2025 are you most proud of, and which one taught you the biggest lesson? Going into 2026, what one financial habit would make the biggest difference if you actually stuck with it? Bring those thoughts into the Facebook group or drop a comment because your reflections might help another Stacker avoid learning the same lesson the hard way. FULL SHOW NOTES: https://stackingbenjamins.com/top-money-lessons-of-2025-1776 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if "giving back" isn't about writing bigger checks but about using what you're already great at? Most people think philanthropy is reserved for people with their names on buildings. That assumption keeps them from realizing they already have something valuable to give. Joe Saul-Sehy, OG, and Neighbor Doug welcome John Studzinski, managing director at PIMCO and founder of the Genesis Foundation, for a conversation about generosity, purpose, and impact that actually applies to everyday Stackers. John challenges the whole concept of "philanthropy" as something for the ultra-wealthy and reframes giving as a muscle anyone can build using time, talent, and intention instead of just cash. The conversation reveals how you can create meaningful impact right now, regardless of your bank balance. Whether you're great at organizing, teaching, listening, or solving problems, those skills matter more than you think. John breaks down how to identify your personal talent for impact and why intentional giving beats reactive charity every single time. Then the show shifts to retirement planning, specifically how to design a glide path that works with your behavior instead of fighting it. Joe and OG break down how to manage risk as you age, why annuities keep showing up in retirement conversations, and why smart planning focuses less on chasing perfect returns and more on creating stability you can actually live with. Because the math might say one thing, but your ability to sleep at night matters just as much. Along the way, the crew takes a detour into ChatGPT's potential future, explores a few behavioral finance truths that hit uncomfortably close to home, and wraps with a pop culture review reminding us that money decisions never happen in a vacuum. This episode is about aligning your resources (financial and otherwise) with the life you actually want to live. What You'll Walk Away With: • Why "giving" is a better word than "philanthropy" and why that shift in language actually matters • How to identify your personal talent for impact even without significant wealth • Why generosity works best when it's intentional and strategic rather than reactive • How retirement glide paths actually work and why your behavior matters more than the math • The role annuities can play in reducing retirement anxiety without sacrificing everything • Why percentages can be misleading, real dollars tell better stories, and context is everything • How fear, FOMO, and age quietly shape your investment decisions in ways you might not notice • Permission to build a retirement plan around stability instead of maximum growth This Episode Is For You If: • You want to give back but think you need more money before you can make a real difference • You're approaching retirement and tired of advice that ignores how you actually feel about risk • You've wondered if annuities deserve their bad reputation or if there's something there • You want your money decisions to reflect your values, not just optimize for returns • You believe purpose and planning should work together, not compete Before You Hit Play, Think About This: What's a talent you already have that could create more impact than money alone? And when it comes to retirement investing, what decision do you know is emotional but still struggle with? Drop your answers in the comments because John's perspective on giving and the crew's take on retirement planning might shift how you think about both. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Some episodes help you protect your money. Some help you protect everything your money makes possible. This episode does both. Joe Saul-Sehy and OG welcome fire safety expert Steve Kerber from UL's Fire Safety Research Institutes, who delivers simple, practical, "do this today" steps that dramatically increase your home's safety. From upgrading outdated smoke alarms to understanding lithium-ion battery risks to spotting hidden hazards most people walk past every single day, Steve gives everyday Stackers the tools to keep their homes and families safer. This isn't scare tactics. It's straightforward guidance from someone who's spent his career studying what actually prevents fires and saves lives. Then the show shifts gears for the headline segment. Joe and OG unpack T. Rowe Price's latest Global Retirement Survey to explore what savers around the world are most anxious about right now. How are people adapting to inflation? Are retirement expectations shifting across different countries? What can you learn from how others are handling the same fears you probably have? The data reveals patterns that might surprise you and insights you can actually use to build more confidence in your own retirement planning. Between these two segments, you'll get Doug's trivia throwdown, a TikTok detour through airport lounge mythology, and a few classic basement moments that remind you why this show mixes serious topics with serious fun. It's a wide-ranging episode packed with actionable takeaways and a good reminder that your financial plan works best when your home, your health, and your long-term outlook are all protected. What You'll Walk Away With: • The small home safety upgrades that make the biggest difference in fire prevention • Why smoke alarms fail more often than you think and how to pick the right replacement • Lithium-ion battery safety covering where to store them, what to avoid, and which myths to ignore • How real-world fire prevention thinking overlaps with smart financial planning habits • What savers around the world worry about most when it comes to retirement • How inflation, longevity concerns, and economic uncertainty are reshaping retirement expectations globally • Practical steps to feel more confident about your long-term retirement plan based on what the data reveals • Permission to take simple safety steps today that your future self will thank you for This Episode Is For You If: • You can't remember the last time you checked your smoke alarms (or know they're overdue for replacement) • You've got lithium-ion batteries around the house but aren't sure if you're storing them safely • You're curious what retirement worries look like around the world and how yours compare • You want retirement insights based on actual data instead of just one expert's opinion • You believe protecting what you have is just as important as growing what you're building Before You Hit Play, Ask Yourself: When's the last time you actually tested your smoke alarms or checked their expiration dates? And what's your biggest retirement worry right now? Drop both answers in the comments because Steve's fire safety tips and the global retirement data might address fears you didn't even realize were universal. FULL SHOW NOTES: https://stackingbenjamins.com/holiday-fire-safety-tips-steve-kerber-1774 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Does more money make life easier, or does it just give you more expensive problems to solve? Most people assume that once they start earning more, their financial life will finally calm down and organize itself. Then they get the raise or the promotion or the business success, and somehow things feel just as chaotic as before, just with bigger numbers involved. Joe Saul-Sehy is joined by Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and OG to explore why "more" isn't always "simpler." The crew digs into early money mistakes they'd all like to forget, the weird psychological traps that show up as income grows, and why your brain doesn't automatically upgrade its money management skills just because your paycheck did. The conversation gets real about the hidden mental challenges that come with wealth growth. Decision fatigue gets worse, not better. Lifestyle creep sneaks in wearing a very convincing disguise. And suddenly you're agonizing over choices that used to be simple, because now you can afford multiple options and none of them feel obviously right. If you've ever wondered why your financial life didn't magically self-organize the moment you started earning more, this roundtable has your answers. The crew also tackles listener questions about building budgeting habits that actually stick, finding genuine financial confidence, and creating systems that scale with your life instead of working against it. Because the goal isn't just to make more money. It's to build a life that feels manageable and intentional at whatever income level you're at. Plus, Doug delivers a trivia showdown featuring fierce competition, questionable strategy, and what might be the most overthought trophy dilemma in basement history. What You'll Walk Away With: • Why more income doesn't automatically reduce financial stress and often creates new complications • The hidden mental traps people fall into as their wealth grows and how to spot them early • How Paula, Jesse, OG, and Joe think about building lasting financial confidence at any income level • Practical budgeting strategies that work whether you're making $50K or $500K • Why simple pleasures matter more (not less) as your money grows • The surprising ways earning more actually complicates everyday decisions • Listener Q&A on habits, organization, and creating systems that smooth out financial chaos • Permission to admit that making more money didn't solve everything like you thought it would This Episode Is For You If: • You're earning more than you used to but somehow don't feel more in control • You assumed financial stress would decrease with income but it just shifted to different problems • You're stuck between multiple good options and can't figure out why that's so paralyzing • You want to hear successful people admit that more money created complications they didn't expect • You're building wealth but want to make sure you're also building a life that feels good Before You Hit Play, Think About This: What's one financial decision that got harder (not easier) as you started earning more money? Drop your answer in the comments because this roundtable proves you're definitely not the only one experiencing this paradox. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Walking away from a secure city government job to eventually run one of the world's most recognizable handbag brands sounds like fiction. For Lew Frankfort, it became his career story, and the path between those two points is exactly what makes this conversation so valuable. Lew joins Joe Saul-Sehy and OG in the basement to break down how a combination of discipline, curiosity, and what he calls "magic and logic" shaped his journey from city hall to the corner office at Coach. This isn't just inspiration for aspiring executives. Lew's insights about making better decisions, taking calculated risks, and building a meaningful life apply whether you're 25 or 55, whether you're climbing the ladder or considering jumping to a different one entirely. Lew shares how preparation became his secret advantage, why curiosity beats confidence during major transitions, and what he learned about leadership while helping transform Coach into a global powerhouse. His framework for balancing intuition with analysis gives the Confident Explorer a practical lens for evaluating their own big moves, career pivots, or midlife reinventions. Then Joe and OG shift gears to tackle a different kind of transition. The first year of retirement. When excitement runs high and "go-go" energy meets newfound freedom, spending can spiral in ways that derail decades of careful planning. They break down the crucial financial decisions retirees face right out of the gate, why that first year can be surprisingly dangerous, and how to set yourself up for long-term stability without killing the joy of finally having time to live. Plus, Doug delivers trivia involving time travel and underwear, because even episodes about CEO wisdom and retirement planning need a reality check from the basement. What You'll Walk Away With: • How Lew Frankfort pivoted from city government work to leading Coach and what that path teaches about career reinvention • The "magic and logic" framework anyone can apply to big decisions and career moves • Why curiosity and thorough preparation matter more than confidence when making your next leap • Leadership lessons from someone who helped build a global brand from the inside • What retirees absolutely must understand about spending during that crucial first year • Why the "go-go years" of early retirement can wreck your finances if you're not careful • Strategies for aligning your early retirement excitement with long-term financial stability • Permission to reinvent yourself at any age, armed with both inspiration and practical wisdom This Episode Is For You If: • You're considering a career change but worried you're too far along to pivot • You want to understand how successful people actually made their big moves • You're approaching retirement and want to avoid the spending traps that catch most people • You're curious how to balance intuition with analysis when making major life decisions • You believe it's never too late to build something meaningful or try something new Before You Hit Play, Think About This: What's one career move or life transition you've been thinking about but haven't pulled the trigger on yet? What's actually holding you back? Drop your answer in the comments because Lew's story might be exactly the perspective shift you need to take that next step. FULL SHOW NOTES: https://www.stackingbenjamins.com/https-stackingbenjamins-com-lou-frankfort-bagman-1772/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 (https://www.stackingbenjamins.com/201) Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Holiday parties make you want to hide behind the cheese tray. Gift-giving season makes your budget cry. This episode is your survival guide for both. Joe Saul-Sehy, OG, and Neighbor Doug welcome Pulitzer Prize-winning author Charles Duhigg to turn holiday small talk from awkward endurance test into something you might actually enjoy. Whether you're facing the office party, a family gathering with that cousin who won't shut up about crypto, or the neighborhood potluck where you know exactly three people, Charles reveals how to walk into any room with confidence, even if you're an introvert who'd rather be home watching movies. The secret? Super communicators aren't the loudest people in the room. They're the ones asking better questions, reading the conversation correctly, and making others feel heard. Charles breaks down the skills that turn painful small talk into genuine connection, and why introverts actually have hidden advantages at holiday gatherings (yes, really). Then the crew tackles the other holiday stressor of gift-giving that doesn't demolish your December budget. Joe, OG, and Doug explore the rising trend of secondhand gifting. It's not just about saving money (though your wallet will thank you). It can be more meaningful, more creative, and kinder to both your finances and the planet. From thrifted treasures to thoughtful "found" gems, they share how to give smarter instead of just spending more. Plus, Doug's toilet paper trivia arrives right on schedule (because what's a holiday episode without something unexpected?), along with stories about neighbors behaving badly and a brief tour through apps you forgot you're still paying for. What You'll Walk Away With: • Charles Duhigg's framework for turning small talk into actual connection without feeling fake • Why introverts have secret advantages at holiday parties and how to use them • Smart, budget-friendly gifting strategies that feel thoughtful rather than last-minute or cheap • The case for secondhand gifts and how to do it in a way that feels special • How to avoid blowing your holiday budget without looking (or feeling) stingy • Creative ways to personalize gifts without overspending or resorting to gift cards • Why communication skills affect both your happiness and your financial decisions This Episode Is For You If: • Holiday small talk feels like torture and you'd rather shovel snow • You want to give meaningful gifts but refuse to wreck your January budget doing it • You're an introvert dreading the season of forced social interaction • You're tired of generic gift guides telling you to "just spend less" without actual ideas • You believe better conversations and smarter spending are both learnable skills Before You Hit Play, Ask Yourself: What's the most meaningful non-new gift you've ever given or received? Think about why it mattered. That's the kind of gifting Charles and the crew are talking about. Drop your story in the comments because we're building the anti-Amazon holiday gift playbook together. FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-actually-enjoy-holiday-small-talk-1771/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's the problem with most frugality advice: it makes you feel like a monk who's taken a vow of joylessness. Joe Saul-Sehy and Neighbor Doug gather the roundtable crew—Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Andy Hill (Marriage, Kids, and Money)—to prove that frugality isn't about deprivation. It's about designing a life that feels good and costs less. The conversation gets real fast: what's the difference between thoughtful frugality and soul-crushing penny-pinching? How do you cut spending without cutting joy? And why do some people thrive on frugal challenges while others just end up resentful and burnt out? The crew shares their own tactics, from "shopping your fridge" (a shockingly high-ROI habit most people ignore) to the power of frugal sprints instead of permanent deprivation mode. They break down how to align your spending with your actual values instead of society's expectations, why raising income often beats shaving another $3 off your grocery bill, and how to turn frugality into something your kids actually want to participate in (no guilt trips required). You'll also hear about the expenses each of them refuses to cut no matter how frugal they get, because smart money management isn't about eliminating everything; it's about keeping what matters and ditching what doesn't. Plus: stories about mystery freezer leftovers, subscription fees that sneak in like cat burglars, and Doug's perspective on... well, whatever Doug decides matters that day. What You'll Walk Away With: • The difference between frugality that improves your life and penny-pinching that just makes you miserable • Why "shopping your fridge" might be the highest-return grocery habit you'll ever adopt • How to design spending around your actual values instead of just cutting blindly • The power of "frugal sprints"—short-term challenges that work without long-term burnout • How to involve your kids in frugal habits without making them feel deprived • Why focusing on raising income often matters more than obsessing over tiny budget cuts • Which expenses the pros refuse to cut—and why knowing your "worth it" list matters This Episode Is For You If: • You want to save money but refuse to live like you're broke when you're not • Traditional frugality advice makes you feel guilty about things that actually bring you joy • You're trying to cut spending but can't figure out where to start without feeling deprived • You want to model smart money habits for your kids without making them fear spending • You're tired of finance advice that assumes everyone should want the same lifestyle Before You Hit Play, Think About This: What's the one expense you refuse to cut, no matter how frugal you get? And what does that tell you about what actually matters to you? Drop your answer in the comments—we want to know what's on everyone's "worth it" list. FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-save-money-without-making-your-life-miserable-sb1770/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's something nobody tells you: knowing how to make money is easy compared to knowing how to spend it well. Morgan Housel, bestselling author and one of the sharpest minds in personal finance, is back in the basement with Joe Saul-Sehy, OG, and Neighbor Doug to tackle the question most financial advice completely ignores: why do we spend the way we do, and how can we get better at it? This isn't about budgeting apps or cutting lattes. It's about understanding the psychology underneath every swipe of your card. Morgan shares stories from his early days working valet for the ultra-wealthy—the spending patterns he observed, the misery he witnessed, and the lessons that changed how he thinks about money forever. Turns out, having more money doesn't automatically make you better at spending it. In fact, it often makes you worse. The conversation digs into what actually creates happiness (spoiler: it's not more stuff), why contentment matters more than your net worth, and how true financial independence isn't about the size of your portfolio—it's about the freedom to make choices that align with your actual values. Morgan also breaks down what Warren Buffett's retirement announcement reveals about staying grounded while building wealth, and why comedians might understand money better than most economists. Plus: Doug takes a trivia detour to a surprisingly risqué national park (because of course), and the crew wraps with binge-worthy recommendations for your next couch night. If you're tired of chasing more and ready to figure out what enough actually looks like, this episode is required listening. What You'll Walk Away With: • Why spending money well is a psychological skill, not a math problem—and how to develop it • What Morgan learned about wealth and misery from parking cars for millionaires in their driveways • The hidden drivers behind your financial decisions (and how to spot them before they derail you) • Why contentment—not consumption—is the real key to long-term happiness • What true financial independence actually means (hint: it's not a number in your bank account) • How Warren Buffett's approach to retirement reveals timeless principles about money and legacy • Simple guiding principles to help you spend smarter and live calmer This Episode Is For You If: • You've hit financial goals but still don't feel satisfied • You're tired of spending money on things that don't actually make you happier • You want to understand why you make the money decisions you do (even the questionable ones) • You're curious what actually separates people who enjoy their money from people who just have it • You believe there's more to financial success than just accumulating more Before You Hit Play, Think About This: What's one purchase you made that brought way more joy than its price tag would suggest—and can you figure out why? That's the kind of spending Morgan's talking about. Drop your answer in the comments—the basement wants to hear what actually brought you happiness. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-art-of-spending-money-with-morgan-housel-1769/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Let's be honest: taxes feel like that thing you're supposed to understand but somehow never learned, and now you're too embarrassed to ask. Joe Saul-Sehy, OG, and Neighbor Doug welcome Hannah Cole—artist-turned-tax-pro and author of the brand-new book Taxes for Humans—to finally explain taxes in language that doesn't require a CPA license to understand. Hannah's built her career translating tax code for freelancers, side hustlers, and small business owners who just want to know what they can deduct, what'll get them audited, and how to stop drowning in shoebox receipts. She breaks down the real difference between a legitimate business expense and wishful thinking, how to track startup costs without losing your mind, and why the bookkeeping system that works is the one you'll actually use (spoiler: it doesn't have to be fancy). Whether you're launching a side gig, running a creative business, or just trying to keep the IRS from ruining your holiday season, Hannah's got the roadmap. Then Joe and OG shift gears to tackle the "AI bubble" conversation everyone's having—is this tech hype justified, or are we watching 1999 all over again? They break down how to think about market froth without panicking, why smart investors don't build their strategy around TikTok prophets predicting doom, and how to prepare your portfolio for volatility without making fear-based moves. Plus: Doug delivers trivia about Richard Pryor's Blazing Saddles days, because even tax talk deserves a palate cleanser. What You'll Walk Away With: • Tax basics explained in actual human language (finally)—what counts as a deduction and what's just wishful thinking • How to set up simple, sustainable bookkeeping systems for side gigs or small businesses that you'll actually maintain • The smartest way to track startup expenses without drowning in receipts or spreadsheets • Why the IRS isn't as scary as you think when you've got your basics covered • How to think about AI market hype without getting swept up in either the euphoria or the panic • Smart strategies for preparing your portfolio for volatility without making emotion-driven decisions • Why the right tax and investing systems buy you back time, creativity, and peace of mind This Episode Is For You If: • You've been winging it on taxes and know you're probably missing deductions (or making mistakes) • You run a side hustle but have no idea what you can actually write off • Tax season makes you anxious because you're never sure if you're doing it right • You're hearing AI bubble talk everywhere and wondering if you should be worried about your investments • You want systems that are simple enough to actually follow, not perfect enough to abandon by February Before You Hit Play, Think About This: What's the tax mistake you wish you could warn your younger self about? Drop it in the comments—we're all learning here, and sometimes the best lessons come from what we got wrong the first time. FULL SHOW NOTES: https://www.stackingbenjamins.com/tax-basics-for-side-hustlers-ai-market-tips/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's a secret: some of the best financial education doesn't come from books or podcasts. It comes from a board game box. Joe Saul-Sehy welcomes Kylie Prymus, board game expert and owner of Pittsburgh's award-winning store Games Unlimited, for a conversation about the games that sneak money lessons into brilliant gameplay. These aren't boring "educational games" that make kids groan—they're genuinely fun strategy games that happen to teach supply and demand, resource management, risk assessment, and long-term planning better than most finance courses. Kylie walks through his top picks for economic games that'll make you (and your kids, and yes, your brother-in-law) think differently about money. From deck-builders like Dominion that teach portfolio diversification to Food Chain Magnate (basically an MBA in a box, but way more entertaining), these games turn financial concepts into actual decisions with consequences you can see play out in real time. But this isn't just about learning—it's about leveling up your holiday gatherings. Kylie shares his favorite cozy games for the season, from the absurdly cute cat-themed strategy game Boop to party games like Monikers that even Uncle Larry can't ruin. Whether you need something cooperative to bring the family together or competitive enough to settle old scores, this episode has you covered. Plus: you'll hear why game stores like Games Unlimited curate experiences (not just inventory), and how the right game can turn a tense holiday gathering into something people actually want to repeat. What You'll Walk Away With: • The board games that teach money concepts like budgeting, income streams, and resource management without feeling like homework • Why Dominion, Food Chain Magnate, and other economic games are secretly brilliant financial teachers • Kylie's top holiday game picks—from cozy strategy games to party games that work for any crowd • How game mechanics like deck-building and resource trading translate directly to real-world money decisions • What to look for when choosing games that work for both newbies and strategy enthusiasts • Why games teach financial lessons better than lectures—and how to use that with kids (or adults who need a refresh) • The surprising ways marketing, scarcity, and community building show up in tabletop games This Episode Is For You If: • You want to teach your kids about money in a way that doesn't feel like a lecture • You're looking for games that are actually fun but happen to build financial thinking • Your family game nights need an upgrade beyond Monopoly arguments • You're curious about board games but don't know where to start • You believe the best learning happens when you're having too much fun to notice you're learning What's Your Money Game? Drop your answer in the comments: What board game taught you a real money lesson, even if it wasn't trying to? Or if your financial personality were a board game, which one would it be? The basement wants to know—and we're always looking for new game recommendations. FULL SHOW NOTES: https://www.stackingbenjamins.com/kylie-prymus-board-games/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Black Friday's coming, your inbox is screaming deals at you, and you're trying to figure out: is this tech actually worth it, or will it be collecting dust by Valentine's Day? Joe Saul-Sehy, guest co-host CFP Anna Allem, and Neighbor Doug bring in Bridget Carey from CNET to cut through the holiday tech chaos. Bridget's spent her career testing gadgets, and she's here to tell you what's actually worth your money this season—from Nintendo's surprisingly strong lineup to handheld gaming devices like Steam Deck and Xbox Cloud that might replace your console. She also warns you away from AI-powered appliances that still feel like they're arguing with you instead of helping. Bridget breaks down the smart way to approach Black Friday and Cyber Monday without wrecking your December budget, which deals are real and which are manufactured hype, and why some tech gifts send a very specific message to your in-laws (and maybe not the one you want). Then the conversation shifts from tech temptations to investing platforms—specifically Robinhood. The confetti animations are fun, the interface is slick, but is it actually built for serious long-term investing? Joe and Anna dig into where Robinhood works, where it distracts, and why your retirement plan might need something more substantial than gamified stock trading and crypto side quests. Plus: Doug delivers Thanksgiving-adjacent trivia, and the crew takes a nostalgic detour through Skip-Its and Long Furbys that'll fuel your next holiday gathering conversation. What You'll Walk Away With: • Bridget Carey's insider guide to which holiday tech deals are legit and which are overhyped garbage • The best gaming and gadget gifts this season (from someone who actually tests this stuff for a living) • Why some AI appliances still feel like expensive beta tests you're paying to debug • Smart strategies for Black Friday and Cyber Monday that don't demolish your December budget • The honest truth about Robinhood: where it shines and where serious investors should look elsewhere • How investing platforms subtly influence your behavior—and whether that's helping or hurting you • How to stay grounded when shiny objects (tech or financial) start calling your name This Episode Is For You If: • You're staring at Black Friday ads wondering which deals are actually worth it • You want tech gift advice from someone who isn't trying to sell you something • You've been using Robinhood and wonder if it's actually helping your long-term investing goals • You're curious whether the flashy features on investing apps are making you a better or worse investor • You need a reality check before holiday spending turns into January regret Before You Hit Play, Ask Yourself: What's the worst tech purchase you've ever made? Bonus points if it broke before New Year's. Drop it in the comments—misery loves company, and we're building the ultimate "do not buy" list together. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Black Friday is coming, and you've got two choices: get trampled at 3 a.m. for a discount air fryer, or learn how the pros actually save hundreds without the drama. Joe Saul-Sehy and Neighbor Doug kick off Black Friday week with the perfect blend of strategy and sanity. First up: Australian comedian Josh Liston tries to make sense of American Thanksgiving traditions and why we consider waking up before dawn to fight strangers over discounted electronics "normal holiday fun." Spoiler: he's not buying it. Then Regina Conway from Slick Deals drops in with the actual playbook. Regina breaks down when to shop during Black Friday week (different categories peak on different days), how to stack coupons with cashback and gift card deals for maximum savings, and why subscriptions and memberships might be the smartest budget-friendly gifts you're not considering. She also reveals how the Slick Deals community spots hidden bargains before they disappear—and how you can do the same. But here's where it gets real: Joe, Doug, and Josh tackle Buy Now Pay Later schemes like Affirm and Klarna. They're everywhere this season, and they're tempting. They're also the financial equivalent of eating Halloween candy for breakfast—feels great in the moment, regrettable by lunch. You'll learn exactly when these services make sense (rare) and when they're just a trap disguised as convenience. Whether you're hunting deals or trying to avoid holiday debt, this episode is your survival guide for coming out ahead. What You'll Walk Away With: • Regina Conway's insider strategy for when to shop during Black Friday week (hint: timing matters more than you think) • How to stack coupons, cashback offers, and gift card deals to maximize every purchase • Why subscriptions and memberships make surprisingly smart (and budget-friendly) holiday gifts • Grocery hacks that actually save money during the most expensive shopping weeks of the year • The truth about Buy Now Pay Later—when it's useful and when it's just expensive debt with good marketing • How community-powered deal sites like Slick Deals help you find and vet bargains before they vanish • Smart strategies to enjoy the holidays without the January credit card hangover This Episode Is For You If: • You want Black Friday deals without the 3 a.m. wake-up call or the crowds • You're trying to save money this season but feel overwhelmed by all the "deals" • You've been tempted by Buy Now Pay Later but aren't sure if it's smart or stupid • You want to give great gifts without blowing your budget (or your sanity) • You believe there's a smarter way to shop than fighting strangers for discounted TVs What's Your Black Friday Strategy? Are you a doorbuster warrior, an online deal hunter, or someone who avoids the whole thing? Drop your approach in the comments—and if you've got a Black Friday horror story (or victory), the basement wants to hear it. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-save-big-this-black-friday-regina-conway-1765 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if you could sit down with the people actually building the future of personal finance and just... ask them everything? That's exactly what happens in this episode. Joe Saul-Sehy gathers three FinTech insiders around the basement table—Peter Polson (founder, Tiller), Aaron Froug (founder, Grifin), and Ryan Ruff (longtime FinTech pro, Array)—for a rare look inside the industry that's reshaping how we handle money. This isn't about pitching their products. It's about understanding how FinTech actually works, where it's headed, and how everyday people can use these tools more effectively. Peter and Aaron share what they've learned building companies from the ground up, while Ryan pulls back the curtain on the infrastructure most people never see but rely on every single day. The conversation goes deep: What are most people getting wrong about money apps? How can you get more value from the tools you're already using? Where is AI actually making finance easier (versus just adding complexity)? And as creators, how can they design tools that genuinely help people instead of just creating more digital clutter? You'll also hear their take on what's coming next—the innovations that'll matter in five years, the trends that are overhyped, and the blind spots the industry still needs to address. Whether you're a FinTech skeptic or an early adopter, this conversation will change how you think about the apps sitting on your phone right now. What You'll Walk Away With: • The insider perspective on how FinTech tools are actually designed—and what builders wish users understood • How to get more value from the financial apps you're already using (most people only scratch the surface) • Where the industry is headed: what innovations are real and what's just hype • Why some tools work for some people but fail for others—and how to find your fit • The infrastructure that makes your financial apps work (and what breaks when it doesn't) • How AI is changing personal finance in practical ways, not just buzzword ways • What FinTech creators are trying to solve—and where they admit the industry still falls short This Episode Is For You If: • You're curious about what's actually happening inside the FinTech world • You want to use your money apps smarter, not just download more of them • You're wondering what's coming next in personal finance tech and whether it'll actually help • You've felt like financial tools are being built for someone else, not for you • You want the insider perspective without the sales pitch—just honest conversation from people who live this every day Before You Hit Play, Think About This: What's one thing you wish your money apps could do better? Drop it in the comments—these are exactly the kinds of insights that help creators build tools that actually work for real people. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-current-state-and-future-of-fintech-1764 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Be honest: When someone's talking to you, are you actually listening—or just waiting for your turn to speak? Joe Saul-Sehy and OG welcome executive coach Katie O'Malley, who's here to expose how terrible most of us are at paying attention—and more importantly, how to fix it. Whether you're trying to connect with your spouse, navigate a tough conversation with your kid, or just survive Thanksgiving dinner without the crypto uncle derailing everything, Katie's got the framework that makes you a better listener (and weirdly, a better decision-maker too). Here's the thing: better listening doesn't just improve your relationships. It improves your money decisions. When you're actually present instead of distracted, you catch the details that matter. You ask better questions. You make choices that align with your values instead of reacting on autopilot. Katie breaks down the reflective listening technique that changes every conversation—at work, at home, and yes, even about money. Joe and OG also dig into financial literacy for younger Stackers (because the skills you wish you'd learned earlier are the ones you should be teaching now), plus new research on all-stock portfolios and whether they're brilliant or just reckless depending on your risk tolerance. And Doug? Doug's got Halloween-adjacent music trivia and commentary that reminds you not everything needs to be taken seriously. What You'll Walk Away With: • The reflective listening framework that immediately improves how you communicate (with everyone) • Why "listening to respond" instead of "listening to understand" sabotages your conversations • Simple techniques to break free from distraction loops—especially the ones involving your phone • How better communication leads to better financial decisions (they're more connected than you think) • What the research actually says about all-stock portfolios and whether they fit your risk tolerance • Ways to teach young people the financial skills they need—even if nobody taught you • Strategies for staying present during stressful family moments (holiday season, we see you) Before You Hit Play, Ask Yourself: • When was the last time you listened to understand instead of just waiting for your turn to talk? • What relationships in your life would improve if you were actually present instead of mentally writing your grocery list? • Are you teaching the young people in your life the money skills you wish someone had taught you? • Does your investment strategy match your actual risk tolerance—or just what sounded good on TikTok? • What uncomfortable conversations are you avoiding because you don't know how to navigate them? Got a communication breakdown you're trying to fix—financial or otherwise? Drop it in the comments. The basement's got your back. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Pop quiz: If your health insurance premiums keep climbing, should you just go catastrophic and pocket the savings? Joe Saul-Sehy, OG, and CFP Anna Allem tackle that exact question, along with a handful of other money decisions that keep Stackers up at night. From navigating healthcare coverage gaps to figuring out when (and how) to withdraw from a 529, this Monday mailbag episode is packed with the practical advice you need, served with the basement humor you've come to expect. The health insurance conversation gets real: what catastrophic plans actually cover (spoiler: less than you think), how to plan for the gaps, and whether gambling on your health is ever a smart financial move. Then Anna breaks down the 529 withdrawal strategy that saves you headaches at tax time, and the crew tackles a listener who's spooked by market volatility and wondering if it's time to bail. But it wouldn't be Monday without some chaos—Joe's cat decided to add drama to the morning, Doug brings trivia about counterfeit currency (because of course), and the gang updates you on the charity challenge where Stackers can support financial literacy and maybe win some prizes in the process. Plus: OG delivers movie reviews to help you figure out what's actually worth your streaming time this week. What You'll Walk Away With: • The truth about catastrophic health plans—when they make sense and when they'll leave you exposed • How to handle healthcare coverage gaps without gambling your financial future • The smart way to withdraw from a 529 so you don't accidentally trigger taxes or penalties • Why market volatility isn't a reason to panic—and what to do instead of bailing on your portfolio • How diversification and rebalancing keep you sane when the headlines get scary • A reminder that financial planning (like cat wrangling) rarely goes exactly as planned This Episode Is For You If: • You're staring at rising health insurance premiums and wondering if there's a better way • You've got a 529 but aren't sure how to actually use it without screwing up • Market dips make you nervous and you want to know if you should be doing something • You're tired of generic financial advice and want real answers to your specific questions • You believe learning about money should involve at least a few laughs (and maybe some cat stories) Got a Question for the Basement? Drop it in the comments or send it our way—you might just hear Joe Saul-Sehy, OG, and Anna tackle it in an upcoming mailbag episode. And if you want to support financial literacy while competing for prizes, check out the charity challenge details in the show. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like you're doing everything "right" with money—but still barely getting ahead? You're budgeting. You're saving what you can. You cut the subscriptions, meal prep on Sundays, and skip the daily latte. So why does it still feel like you're spinning your wheels? In this Greatest Hits episode, Joe Saul-Sehy welcomes Erin Lowry (Broke Millennial), Paula Pant (Afford Anything), and Greg McFarlane (Control Your Cash) to tackle the question nobody wants to ask: What if the problem isn't your spending—it's your income? Erin shares her journey from broke and stressed to financially stable and empowered, and the crew digs into why so many families struggle even when they're following all the "rules." Sometimes extreme budgeting isn't the answer. Sometimes you need to earn more. And yes, that's easier said than done—but this episode gives you the roadmap. From practical strategies for saving for retirement when cash is tight, to negotiation tricks that lower your monthly bills, to the hilariously strange side hustles people actually do for extra money (you'll never look at classified ads the same way), this conversation is packed with ideas you can use today. Plus: Classic basement banter, a "Spider Pig" serenade, Tony Romo's birthday, and all the tangents that make Stacking Benjamins feel like hanging out with friends who happen to know a lot about money. What You'll Walk Away With: • Why you might feel behind even when you're doing everything the experts tell you to do • Erin Lowry's framework for moving from "broke" to financially confident (and why it's not just about willpower) • When to focus on cutting costs vs. when to focus on earning more—and how to know the difference • Practical retirement savings strategies that work even when your cash flow is tight • Negotiation scripts for lowering your internet, phone, and other monthly bills (yes, they actually work) • Creative (and sometimes bizarre) ways people make extra money that you've probably never considered This Episode Is For You If: • You're exhausted from budgeting and feel like you're sacrificing everything but still not getting ahead • You wonder if you're just bad with money—or if something else is going on • You've cut expenses as far as they'll go and need new strategies • You're curious about side hustles but don't know where to start (or what's actually worth your time) • You need a reminder that struggling financially doesn't mean you're doing it wrong—sometimes the system is just rigged FULL SHOW NOTES: https://stackingbenjamins.com/stop-worrying-start-saving-greatest-hits-week-1761 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's what nobody tells you about building wealth: it's not about finding the perfect investment or timing the market. It's about doing boring things consistently until they're not boring anymore—they're just your life. In this Greatest Hits episode, Joe Saul-Sehy and OG revisit a 2023 conversation with Jonathan Clements, the beloved former Wall Street Journal personal finance columnist and founder of Humble Dollar who passed away recently. We're resharing this episode to honor Jonathan's legacy, his gift for making complex ideas simple, and the joy he brought to every conversation about money. Jonathan's book, My Money Journey, features 30 real stories from real people who built financial freedom—and the lessons are surprisingly simple (which doesn't mean easy). In this conversation, Jonathan breaks down what separated the people who made it from the people who kept spinning their wheels: steady habits, ruthless simplicity, and the kind of resilience that lets you keep going when life throws curveballs. From emergency funds that actually saved people to the rent vs. buy debate that reveals more about your priorities than your budget, this conversation cuts through the complexity to show you what actually matters. Jonathan's wisdom feels even more valuable now—a reminder that the best financial advice isn't about chasing trends, it's about building a life that works for you. Joe and OG also tackle listener questions, including whether to relocate for a better job and how to balance saving for tomorrow without sacrificing today. Plus: Doug's trivia, a Key & Peele-inspired TikTok minute, and proof that the best financial teachers leave lessons that last long after they're gone. What You'll Walk Away With: • The money habits that showed up in almost every success story from Jonathan's book (spoiler: none of them are sexy) • Why simplicity beats complexity in investing—and how to stop overcomplicating your portfolio • The rent vs. buy question reframed: it's not just about math, it's about what kind of life you want • How to balance aggressive investing with the safety net you actually need (not the one Instagram tells you to have) • Why emergency funds and health insurance are the unsexy heroes of every financial success story • What "margin for error" really means—and why it's the difference between surviving setbacks and being destroyed by them This Episode Is For You If: • You're tired of chasing the next "hot" investment strategy and want to know what actually works • You feel like everyone else has figured out money except you (spoiler: they haven't) • You want to hear real stories from real people, not just theory from talking heads • You're trying to balance living well now with saving for later—and feeling stuck in the middle • You believe the best teachers are the ones whose lessons outlive them Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's a wild idea: What if the thing holding you back isn't your bank account, your age, or your circumstances—it's just the story you've been telling yourself? Joe Saul-Sehy and OG sit down with Colin O'Brady, four-time world record holder and endurance athlete who's done things most people would call impossible: solo trek across Antarctica, row across the Drake Passage, and yes, take a 12-hour walk that changed his entire perspective on what humans are capable of. Colin's not just here to tell adventure stories (though those are incredible). He's here to talk about the mental game—the part where you convince yourself to take the first step even when the finish line seems impossibly far away. Sound familiar? Whether you're staring down a cross-country expedition or trying to figure out if you'll have enough saved for retirement, the challenge is the same: push past the voice that says "I can't" and prove to yourself that you can. Then Joe and OG bring it back to the basement with a listener question about Roth vs. Traditional 401(k) contributions—because financial endurance is just as important as physical stamina. They break down how to think long-term about taxes, flexibility, and building a retirement plan that actually fits your life. Plus: Neighbor Doug delivers trivia that proves even world record holders have to earn their laughs in the basement. What You'll Walk Away With: • What Colin O'Brady's 12-Hour Walk reveals about breaking through your mental limits (and how it applies to money decisions too) • The mindset shift that separates people who attempt big goals from people who actually achieve them • Smart strategies for balancing Roth and Traditional 401(k) contributions based on your timeline and tax situation • Why flexibility matters as much as discipline—whether you're planning an expedition or planning retirement • Permission to set goals that scare you a little (because that's usually where the good stuff happens) This Episode Is For You If: • You've been telling yourself you "can't" do something but wonder if that's actually true • You want inspiration that comes with actual tactics (not just motivational fluff) • You're trying to figure out the Roth vs. Traditional 401(k) question and want a clear answer • You believe your best life is out there, but you're not sure how to build toward it • You need a reminder that big transformations start with small, intentional steps FULL SHOW NOTES: https://stackingbenjamins.com/conquer-your-mount-everest-greatest-hits-week-1759 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Want to know what keeps retirees up at night? It's not what they did—it's what they wish they'd done ten years earlier. Joe Saul-Sehy is joined by Jill Siriani (Frugal Friends), Jesse Cramer (The Best Interest), and Doc G (Earn & Invest), who all pull up chairs in the basement for a powerhouse roundtable on the five regrets that show up again and again when people hit retirement. These aren't hypothetical "what-ifs"—they're real stories from a real CFP, sharing tales about people who wished someone had told them sooner. From botched investment allocations that left people either too risky or too conservative, to tax mistakes that cost tens of thousands, to the heartbreaking pattern of people who saved everything but never actually enjoyed their money—this conversation gets real about what actually matters when you're trying to retire with confidence (and joy). The good news? Every single one of these regrets is avoidable. The panelists share what to do now so you don't become one of these stories later, including the estate planning moves that take ten minutes but save your family years of headaches, and why the biggest retirement regret isn't financial at all—it's emotional. Plus: Doug's trivia challenge pits the panel against each other for bragging rights, because even serious money talk deserves a little competition. What You'll Walk Away With: • The five regrets that show up over and over in retirement—and the specific moves that prevent each one • Why your investment allocation in your 40s and 50s might be setting you up for regret in your 60s • Tax strategies that keep more money in your pocket (because giving Uncle Sam extra is nobody's retirement dream) • The simple estate planning steps most people skip—and why your family will thank you for not skipping them • How to give yourself permission to actually enjoy your money instead of hoarding it out of fear This Episode Is For You If: • You're decades from retirement but want to avoid the "I wish I'd known" moments • You're closer to retirement and worried you've missed something important • You want to hear top financial minds debate what actually matters (spoiler: they don't always agree) • You're tired of generic retirement advice and want to hear what real retirees actually regret • You believe retirement should be about living well, not just having enough FULL SHOW NOTES: https://stackingbenjamins.com/top-5-retirement-plan-regrets-1758 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's a question: If everyone's buying annuities right now, does that mean you should too? Joe Saul-Sehy, OG, and Neighbor Doug tackle that exact question in this week's episode—but first, they're starting with the basics. Because before you can figure out complex financial products, you need to nail the fundamentals. And who better to teach them than Karen Holland, founder of Gifting Sense, who's made it her mission to help kids (and their parents) understand money in ways that actually stick. Karen breaks down how to teach the next generation about "need vs. want," why middle schoolers need to understand the real cost of "cool," and how financial literacy can be empowering instead of intimidating. Whether you've got kids or just want a refresher on the money basics you wish someone had taught you, this conversation is the reset button you didn't know you needed. Then things get timely: annuity sales are booming, and everyone's suddenly got an opinion. But are annuities the safe harbor they're marketed as, or just another way to lock up your money with fees you don't understand? Joe and OG cut through the sales pitch to help you figure out when annuities make sense—and when you're better off walking away. Plus: Doug delivers "life-changing" trivia (his words), there's an iHeart Music Festival giveaway tied to financial literacy, and you'll get your weekly dose of basement wisdom served with laughs. What You'll Walk Away With: • Karen Holland's framework for teaching kids financial literacy that actually changes behavior (not just lectures that go in one ear and out the other) • Why annuity sales are exploding right now—and the questions you MUST ask before signing anything • The difference between annuities that solve real problems and annuities that just create expensive ones • Financial habits that work at any age—whether you're teaching a 12-year-old or retraining yourself • How supporting financial education can score you iHeart Music Festival tickets (because doing good shouldn't be boring) This Episode Is For You If: • You want to teach kids about money but don't know where to start (or worry you'll mess it up) • Someone's pitched you an annuity and you're not sure if it's brilliant or a trap • You've heard annuities are "safe" but want to understand what you're actually giving up • You believe financial literacy is a gift worth giving—to your kids, your community, or yourself • You want money advice that doesn't talk down to you or assume you already know everything FULL SHOW NOTES: https://stackingbenjamins.com/raising-money-for-financial-literacy-1757 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Nobody plans for their finances to get tight. But here you are, staring at your bank account, wondering if you should panic now or wait until next Tuesday. Joe Saul-Sehy, OG, and Neighbor Doug are here to talk you off the ledge—and give you an actual plan for when money gets squeezed. Whether you're facing a layoff, dealing with reduced hours, bracing through a government shutdown, or just trying to make your paycheck last until payday, this episode is your financial storm shelter. The good news? You don't need to have everything figured out perfectly to make it through. You just need to know what to do first, what can wait, and how to keep your head (and your budget) together when everything feels uncertain. From building an emergency fund that actually works for your life to eating well on a ramen budget (spoiler: it's possible), this crew breaks down the practical moves that keep you afloat. Plus: Doug delivers trivia, the gang tackles the Voices for Good Charity Challenge (because even in tough times, small acts of giving matter), and they dissect a TikTok money tip that's... well, let's just say not all financial advice should be followed. What You'll Walk Away With: • The first three moves to make when money gets tight—before the panic spiral starts • How much emergency fund you actually need (hint: it's probably less than you think to get started) • Budget-friendly tactics for groceries, utilities, and keeping yourself fed without living on instant noodles • What to do about insurance and loans when cash flow slows down (and which mistakes cost you later) • Why small acts of generosity matter even when you're struggling—and how they help you too • A reminder that financial storms are temporary, but the skills you build weathering them last forever This Episode Is For You If: • Money feels tighter than it used to and you're not sure what to do about it • You want to build a safety net but don't know where to start (or how much is "enough") • The economy feels shaky and you want to feel prepared instead of panicked • You're tired of generic advice like "just save more" and want actual tactics • You need a pep talk wrapped in practical wisdom—because optimism without a plan isn't helpful FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-emergency-funds-1756 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Pop quiz: What's scarier than a haunted house? Opening your credit card statement after a "just this once" shopping spree turned into a six-month spiral. Joe Saul-Sehy and Neighbor Doug gather 'round the basement campfire with Doc G (Jordan Grumet from Earn and Invest), Jesse Cramer (Personal Finance for Long Term Investors), and special guest Emily Egashira—AKA Your Friend Em from TikTok and Instagram fame—to share the financial horror stories that still wake them up at night. We're talking ghostly car-leasing nightmares, investment decisions that refuse to stay buried, and the kind of money mistakes that haunt you long after Halloween is over. But here's the thing about financial horror stories: they're only scary if you don't learn from them. Every tale in this episode comes with the lesson that could've prevented it—the red flag that got ignored, the advice that should've been followed, the moment when "this seems like a bad idea" got drowned out by "but everyone else is doing it." From impulse purchases that turned into long-term regrets to the financial advice that sounded great... until it didn't, this crew proves that the scariest monsters aren't in the movies. They're in our bank accounts, our retirement plans, and that subscription we forgot to cancel three years ago. Plus: Doug delivers Halloween trivia with a full-moon twist, because even financial terror deserves a side of fun. What You'll Walk Away With: • Real financial horror stories from people who lived to tell the tale (and learn from it) • The common thread in most money disasters—and how to spot it in your own life • Why car leases, "great investment opportunities," and "everyone's doing it" should always make you pause • How to turn your own financial frights into lessons instead of letting them haunt you forever • The confidence to say "no" when something feels off, even if you can't explain why This Episode Is For You If: • You've ever made a money decision you immediately regretted (welcome to the club) • You want to learn from other people's expensive mistakes instead of repeating them • You've got a financial skeleton in your closet and need to know you're not the only one • You appreciate brutal honesty wrapped in humor—because laughing at financial pain is cheaper than therapy • You're ready to face your money fears instead of hiding from them until tax season FULL SHOW NOTES: https://stackingbenjamins.com/money-nightmares-wallet-portfolio-credit-1755 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You know what's truly terrifying? Realizing you and someone you share money decisions with have completely different ideas about finances—and you're both convinced you're right. Joe Saul-Sehy and OG welcome Doug and Heather Bonaparte, a CFP and business partner duo who've mastered the art of not killing each other over finances. And when you work together AND live together? Let's just say they've had plenty of practice navigating the financial frights that haunt any relationship where money's involved. Whether you're married, dating, splitting rent with a roommate, or partnering on a business venture, the same money monsters show up: the "fair split" debates, the family expectation zombies that won't stay dead, and those vampiric spending habits that drain shared accounts when you're not looking. Doug and Heather share what actually works—the timing tricks, the tone shifts, and the teamwork strategies that keep financial conversations from turning into horror shows, no matter who you're talking to. This isn't about becoming perfect financial partners overnight. It's about exorcising the money demons before they possess your most important relationships—romantic, professional, or otherwise. Plus: Joe and OG stir the cauldron with Halloween movie talk and trivia, because even the scariest conversations are better with a little basement humor. What You'll Walk Away With: How to start money conversations without summoning the spirits of past arguments (works for spouses, roommates, business partners, you name it) Doug and Heather's hard-won strategies for navigating disagreements when money and relationships overlap Why "financial transparency" isn't about policing every purchase—it's about understanding each other's money ghosts The three things any financial partnership needs to align on before the little stuff stops haunting you Permission to be messy while you figure this out (even CFPs have money fights) This Episode Is For You If: You share financial decisions with ANYONE—a partner, roommate, business associate, or family member Money conversations feel like walking through a haunted house blindfolded Someone else's financial habits make you want to scream louder than a horror movie victim You're tired of being cast as the villain every time you want to discuss shared expenses You need proof that even professionals who literally do this for a living still have to work at it FULL SHOW NOTES: https://stackingbenjamins.com/money-communication-horror-stories-1754 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's scarier than a haunted house? Looking at your retirement account after ignoring it for five years. Joe Saul-Sehy, OG, and Doug welcome back Chuck Jaffe (Money Life with Chuck Jaffe) for his legendary annual Halloween visit—and this year, he's bringing two treats to the basement. First up: Chuck's Halloween Money Game for kids. Picture this: trick-or-treaters can take one piece of candy and walk away... or they can play a game where they might win more candy, actual money, or lose it all. It's economics wrapped in a Snickers bar. Chuck breaks down how each choice teaches kids (and parents) about risk, reward, delayed gratification, and why sometimes the safe bet is actually the smart bet. If you've got kids—or just want a genius way to gamify money lessons—you'll want to steal this. Then things get spooky. Real Stackers share their most bone-chilling financial horror stories: the credit union error that nearly cost someone their house, the coworker's "advice" that turned into a disaster, and the procrastination that haunted someone for years. These aren't fictional frights—they're real mistakes that real people are still recovering from. And every story comes with the lesson that could've prevented it. Plus: Doug's trivia takes a Halloween turn (naturally), and Joe and OG debate whether government incentives are more trick or treat. What You'll Walk Away With: Chuck Jaffe's brilliant Halloween Money Game—how to teach kids about risk, reward, and smart decisions using candy The economic principles hiding in every trick-or-treat choice (and how to explain them without killing the fun) Real Stacker horror stories: the financial mistakes that haunt people for years The red flags that could save you from starring in your own money nightmare Why the scariest financial advice often comes from people who mean well This Episode Is For You If: You want a creative way to teach kids about money that doesn't involve a boring lecture You've ever made a financial decision you wish you could take back You want to learn from other people's mistakes instead of making them all yourself You've got a money skeleton in your closet and want to know you're not the only one FULL SHOW NOTES: https://stackingbenjamins.com/frightening-halloween-stories-with-chuck-jaffe-1753 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's a question nobody in the FIRE movement talks about: What if you reach financial independence... and don't want to quit? Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Doc G (Earn & Invest) tackle the idea of Reverse FIRE—people who've hit their number but choose to keep working anyway. And before you roll your eyes, hear them out. Because it turns out that having enough money doesn't automatically make you happy. And for a lot of people, walking away from work means walking away from purpose, identity, and the structure that kept them sane. The question isn't just "can I afford to retire?"—it's "what am I retiring to?" This conversation gets real about the hidden costs of quitting too soon, why some financially independent people feel guilty for wanting to work, and how to think about retirement not as a finish line but as a design problem. Whether you're sprinting toward early retirement or secretly wondering if you'd be bored out of your mind, this episode will make you rethink what freedom actually looks like. Plus: Doug's T-shirt trivia takes a weird turn (as always), and the crew proves that the best financial conversations happen when nobody's trying to sell you a course. What You'll Walk Away With: • Why "enough money" doesn't equal "enough purpose"—and what to do about it • How to think about work after financial independence (hint: it's not all or nothing) • The identity crisis nobody warns you about when you stop working—and how to avoid it • What financially independent people actually do with their time (spoiler: many keep earning) • Permission to want both: financial security and meaningful work Before You Hit Play, Think About This: If money wasn't an issue tomorrow, would you keep doing what you're doing? If the answer is "no"—why are you still doing it? And if the answer is "yes"—what does that tell you about retirement? Drop your take in the comments. The basement wants to know: Are you racing toward FIRE, or are you building something you never want to leave? Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's the secret nobody tells you: your money problems probably aren't math problems. Joe Saul-Sehy and OG sit down with Carl Richards—financial planner, New York Times columnist, and the guy behind those brilliant "Sketch Guy" drawings that make money actually make sense. Carl's spent his career helping people untangle their relationship with money, and his big insight? Most of us are overthinking it. Your financial plan shouldn't feel like a calculus final. It should feel like a map you can actually follow. Carl breaks down why emotions (not spreadsheets) drive most money mistakes, how to cut through the noise that keeps you paralyzed, and why the simplest plan is usually the one you'll actually stick to. If you've ever felt like you're "doing it wrong" because your strategy doesn't involve leveraged ETFs or cryptocurrency mining, this conversation will be a relief. Then Joe and OG dive into the options trading debate. Is it a legitimate tool for managing concentrated stock risk, or just financial cosplay for people who watch too much CNBC? They break down when options might make sense, when they're just expensive complexity, and how everyday investors should think about them (if at all). Plus: travel stories, Neighbor Doug's trivia (where he definitely brags about something), and proof that you can get smarter about money without wanting to take a nap. What You'll Walk Away With: Carl Richards' framework for simplifying your financial life—and why "The Behavior Gap" matters more than your rate of return Why the emotions behind your money decisions matter more than the math (and how to work with them, not against them) How to filter out financial noise and focus on the handful of things that actually move the needle The truth about options trading: when it's a smart risk management tool and when it's just expensive gambling Permission to keep your plan simple—even if it feels like everyone else is doing something fancier This Episode Is For You If: You feel like everyone else has figured out money except you Financial jargon makes you want to hide under a blanket You've got a solid income but still feel anxious about your money decisions You'd rather learn through real stories than get lectured by a guy in a suit You want to finally understand why you make the money choices you do (good and bad) FULL SHOW NOTES: https://stackingbenjamins.com/how-to-manage-your-money-goals-and-life-with-carl-richards-1751 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You've got questions. We've got two CFPs and a former planner ready to hash it out. Joe Saul-Sehy, OG, Doug, and CFP Anna Allem tackle the money decisions you're actually losing sleep over—and here's the thing: they don't always agree on the answer. That's the point. Should you drain your emergency fund to pay off debt? Is whole life insurance for your kids a smart move or an expensive mistake? How much life insurance do you actually need (not what some calculator tells you)? And when life throws you a curveball—layoff, surprise expense, major purchase—what's the move? With Joe Saul-Sehy's 16 years in financial planning, OG's CFP perspective, and Anna's insights, you'll hear how experienced voices think through these decisions differently—and why your answer might be different than all of theirs. Because the real skill isn't finding THE right answer; it's learning how to make YOUR right call. This episode is for anyone who's ever stared at their bank account thinking, "I know I should do something... but what?" Plus: Doug delivers trivia about the first auto insurance policy (because of course), the gang weighs in on athlete endorsements and reverse mortgages, and there's a TikTok money tip that sparks some debate. What You'll Walk Away With: • How experienced financial minds approach the emergency fund dilemma differently—and what that means for your situation • The whole life insurance debate: when it makes sense for kids and when you're better off elsewhere • A framework for figuring out how much life insurance you actually need—and why the "rules of thumb" don't always work • What to do when your financial plan meets real life (layoffs, surprise bills, major purchases) • The confidence to make a decision even when experts would handle it differently Before You Hit Play, Ask Yourself: What's the one money question you keep Googling but still don't feel confident about? If you're second-guessing your emergency fund, your insurance, or a big financial move, this episode is your permission to stop spinning and start deciding. Got a question we didn't cover? Call in to the show! StackingBenjamins.com/Voicemail FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-burning-financial-questions-1750 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think some people just have all the luck? Think again. Joe, OG, Paula Pant (Afford Anything), and Chris Luger (Heavy Metal Money) break down what separates people who catch breaks from those who don't...and spoiler alert: it's not about being in the right place at the right time. It's about what you DO when opportunity shows up. And before that: how you create the conditions for opportunity to find you in the first place. This episode digs into three moves that make luck happen: staying curious (even when you think you know the answer), being generous (yes, it pays off financially), and staying flexible when life throws you a curveball. Whether you're stuck on a money decision, feel like you're missing opportunities, or just want to stop watching other people win, this conversation will shift how you see "luck." Plus: Doug's trivia gets weird (what even IS a buttload?), the gang debates pumpkin spice season, and you'll hear stories that prove the best financial wins rarely go according to plan. What You'll Walk Away With: The one thing "lucky" people do that creates more opportunities—and how to start doing it today Why helping others might be your best financial strategy (and the science behind it) How to spot opportunities you're currently walking past What to do when your financial plan falls apart (hint: the flexible win) Permission to try something new, even if you're not sure it'll work Before You Hit Play, Think About This: What's one time something good happened to you? ...not because of random chance, but because you were curious, helped someone, or said yes to something outside your comfort zone? That's the kind of "luck" we're talking about. Got a story? We want to hear it. Drop it in the comments or share it in your podcast app. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-find-more-luck-with-your-money-1749 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You don’t have to command a cruise ship (or a boardroom) to lead with purpose. On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Richard Fain, longtime chairman and former CEO of Royal Caribbean Group, for a conversation that’s not about corporate leadership… but about life leadership. Richard shares timeless lessons he learned from decades steering one of the world’s most innovative companies—lessons that apply just as powerfully to parenting, coaching your kid’s soccer team, running a PTA fundraiser, or simply trying to create more joy at home. You’ll hear how to dream bigger about your own life, build a culture of kindness and excellence in small groups, and turn the ordinary moments around you into opportunities to “deliver the WOW.” Of course, this wouldn’t be the basement without a few money detours. The crew also breaks down new 401(k) rules and annuity updates, debates whether tax flexibility beats fancy planning, and celebrates Doug’s birthday with trivia, laughter, and a few movie reviews along the way. By the end, you’ll walk away inspired to bring a little more vision, creativity, and generosity into every corner of your world. No cruise ship required. What You’ll Learn How to lead from wherever you are: Richard’s lessons on building strong teams, communities, and families. No corner office needed. Turning the ordinary into extraordinary: Simple ways to “deliver the WOW” at home, work, or anywhere people count on you. Dreaming bigger about your life: Why bold vision isn’t just for CEOs; it’s for anyone looking to create meaning and momentum. Financial updates you can use: New 401(k) rules, annuity insights, and practical tips to strengthen your plan. The lighter side of leadership: Trivia, birthday celebrations, and a few fun detours (because we can’t resist). Questions for the Basement What’s one way you could “deliver the WOW” in your own life this week? Who’s a leader in your everyday world (at home, work, or your community) who’s made an impact on you? How can dreaming a little bigger change the way you approach your next financial or personal goal? FULL SHOW NOTES: https://stackingbenjamins.com/better-money-habits-with-richard-fain-1748 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

When gold shines, so do the hot takes, and today, the Stacking Benjamins crew dives into what this record-breaking surge really means for your money. Joe Saul-Sehy, OG, and Neighbor Doug kick off the week with their signature Monday salute to our troops before digging into the glittering headlines: gold prices are hitting new highs… but does that make it a smart investment or just financial fool’s gold? From breaking down why gold spikes when markets wobble to questioning whether it’s truly the “safe haven” it’s cracked up to be, the guys unpack the myths, mindset, and math behind precious metals. You’ll also hear fresh strategies for weathering volatile markets, balancing your asset allocation, and staying cool when everyone else is panicking. And of course, Doug drops in with a TikTok Minute, a trivia challenge, and one listener’s wild math-powered success story that somehow involves an Olive Garden. (Breadsticks optional.) So grab your coffee, your calculator, and maybe your lucky coin—because this episode proves that in the unpredictable world of investing, sometimes the smartest move is knowing why you’re holding what you’re holding. What You'll Learn Why gold prices are climbing and what that might signal about the global economy. The myth of “safe haven” assets: When gold works, when it doesn’t, and why diversification still wins. Smart portfolio moves for volatile times—without letting emotions tank your returns. Real-life stories and lessons from Stackers proving that good math (and a little luck) can go a long way. The lighter side of finance: Breadsticks, TikTok, and trivia—because learning about money doesn’t have to feel like homework. Questions You'll Want to Answer: Do you view gold as an investment, insurance policy, or just a shiny distraction? What’s your go-to strategy when markets start getting rocky? Have you ever made a “safe” financial move that didn’t turn out as safe as you thought? FULL SHOW NOTES: https://stackingbenjamins.com/gold-and-other-investments-for-bear-markets-1747 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Who says you have to wait until 65 to clock out and start living your best life? On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, Paula Pant (Afford Anything), OG, and special guest Sean Mullaney—author, CPA, and early retirement strategist—explore how to design a life that lets you walk away from the office sooner and happier. From tax-smart withdrawal strategies to dialing in your lifestyle design, this conversation pulls back the curtain on what it really takes to achieve early financial independence. You’ll hear practical steps for aligning your money with your values, structuring your investments for flexibility, and ensuring your plan can survive market dips and surprise expenses. Along the way, the team debates Roth vs. Traditional retirement accounts, shares personal insights from FinCon, and delivers a few laughs (and groans) in Doug’s trivia corner. Whether you’re in your 30s planning a slow exit or in your 50s wondering if it’s too late to pivot, this episode is your guide to crafting a retirement plan that works as hard as you do—without losing sight of the joy along the way. What You'll Learn How to design your early retirement plan: The building blocks of lifestyle design and financial freedom. Tax-efficient investing: When to prioritize Roth vs. Traditional accounts—and why both can play a role. Withdrawal strategies that work: How to avoid tax traps and keep your plan sustainable. The mindset shift: Why retiring early isn’t about leaving work—it’s about moving toward purpose. How to “future-proof” your finances: Guarding against inflation, longevity risk, and unexpected curveballs. Questions to Ponder During Today's Show: What would your perfect day look like if you didn’t have to work tomorrow? Would you be willing to earn less now if it meant retiring five years earlier? What does “enough” look like for you—and how do you know when you’ve reached it? FULL SHOW NOTES: https://stackingbenjamins.com/building-your-early-retirement-plan-1746 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if building wealth wasn’t just about stacking dollars — but also stacking good deeds? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG sit down with Mel Dorman, a powerhouse real estate investor who turned humble beginnings (yes, dumpster diving beginnings) into a thriving portfolio of 34 rental units in just five years. And she didn’t just build wealth — she built community along the way. From negotiating creative seller-financed deals to forging partnerships that benefit both investors and neighborhoods, Mel shares how real estate can be a tool for connection as much as for cash flow. You’ll learn how she leverages relationships, uses alternative financing to scale quickly, and even flips properties without traditional bank loans — all while staying grounded in her mission to help others. But that’s not all: Joe and OG also break down the latest Federal Reserve moves and what they mean for your wallet. And of course, Neighbor Doug drops by with his signature trivia to remind us that building wealth is serious business… but it’s okay to have some fun while you’re at it. What You'll Learn Creative ways to build wealth: How seller financing can unlock deals you never thought possible. The power of purpose: Why combining community impact with real estate investing is a winning formula. Real-world strategies: Mel’s journey from zero to 34 units — and the lessons she learned along the way. How Fed rate changes affect you: What rising (or falling) rates mean for investors and homeowners. Financing myths busted: Why traditional bank loans aren’t the only way to grow a portfolio. Points to Ponder: Could creative financing open doors for your investing goals? How might building stronger community ties improve your financial outcomes? Are you prepared for how interest rate changes could impact your next big money move? This episode isn’t just a guide to real estate success — it’s a reminder that money works best when it works for everyone. Grab a notebook, pour yourself something caffeinated, and join us for a conversation that just might change how you think about wealth building. FULL SHOW NOTES: https://stackingbenjamins.com/real-estate-investing-in-your-community-1745 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if the key to a richer life isn’t about chasing the next hot stock or grinding harder — but learning to master the timeless truths of money? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug pay tribute to legendary financial writer Jonathan Clements by revisiting five of his most impactful lessons. These aren’t complicated formulas or secret hacks — they’re the kind of deceptively simple ideas that change the way you think about money, work, and what truly matters. We’ll explore why prioritizing financial stability before passion can actually lead you to a more fulfilling career, how “winning by not losing” may be the most underrated investing strategy of all time, and why patience isn’t just a virtue — it’s a tax strategy. Along the way, we’ll talk about how to strike the right balance between frugality and joy and why living your life may be the best investment you ever make. Plus, we help Stacker Kat tackle a tricky severance situation and share tips on how to put that cash to work without capsizing your financial plan. If you’ve ever wondered how to align your money with a life you actually love, this conversation is the perfect mix of inspiration and actionable wisdom. Grab your coffee mug and settle into Mom’s basement — this is an episode you’ll come back to whenever you need a financial reset. What You'll Learn The real reason you shouldn’t chase passion too soon — and what to do instead How to avoid the most common (and costly) financial mistakes Why patience pays: how time turns taxes into opportunity How to balance frugality with actually living a fulfilling life Smart ways to use severance, high-yield savings, and investing strategies together Points To Ponder: Which of Jonathan Clements’ five money lessons hits closest to home for you? Have you ever faced a tough severance decision like Stacker Kat’s? What did you do? Do you believe financial stability should always come before passion — or is there a time to flip that script? FULL SHOW NOTES: https://stackingbenjamins.com/five-pearls-of-wisdom-from-jonathan-clements-1744 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If your financial plan feels more like a vague wishlist than a real roadmap, this episode is about to change that. Live from the basement of YouTube HQ, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long-Term Investors) roll up their sleeves and dig into the three most common — and costly — mistakes people make with their money plans. Whether you’re just starting out or you’ve been stacking for years, this conversation will help you turn “someday” into a solid plan you can actually follow. The gang isn’t just talking theory — they’re breaking down the real reasons plans fail and how to fix them. From adding actionable next steps (instead of endless spreadsheets and good intentions) to weaving in crucial tax and estate planning moves, you’ll discover how to transform your financial plan into a tool that works for you. And because this is Stacking Benjamins, you can expect plenty of banter, relatable stories, and a trivia detour or two along the way. By the time we wrap, you’ll know how to evaluate whether your plan is truly moving you toward your goals, how to communicate more effectively with your financial pros, and how to stop second-guessing every decision. It’s financial planning with fewer headaches, more confidence, and maybe even a little fun. What You’ll Learn Why most financial plans fail — and how to make yours bulletproof The three crucial elements every solid plan needs (and most are missing) How to incorporate tax strategies, estate planning, and real action steps Smart ways to communicate with your advisor or team about what matters most Questions to Consider How to course-correct if your plan’s gone off the rails Does your financial plan include clear, actionable steps — or just big goals? Have you factored in tax and estate planning, or are you leaving those to chance? Are you confident your plan will work in real life, not just on paper? FULL SHOW NOTES: https://stackingbenjamins.com/three-things-missing-from-most-financial-plans-1743 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think your retirement plan is bulletproof? Think again. In this eye-opening episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by certified financial planner Jeremy Keil, CFP® to walk you through the steps to building a retirement plan that won’t crack under pressure. From mapping out your spending before you ever leave the workforce to crafting a tax strategy that keeps more money in your pocket, this conversation is your blueprint for making your golden years actually golden. But just when you think you’ve got retirement handled, we throw a curveball: private equity. With giants like Goldman Sachs and T. Rowe Price trying to slip these complex investments into your 401(k), it’s time to ask whether “more opportunity” is really a good thing — or a trap for the unprepared. Joe and OG break down the risks, the realities, and what you need to know before you sign on the dotted line. As always, we serve it all with a side of basement banter — from Doug’s trivia about the first issue of Playboy to a TikTok football moment you didn’t know you needed — plus real-life stories that prove retirement planning is as much about mindset as it is about math. What You'll Learn In Today's Show: The five key steps to building a retirement plan that works for you, not just a generic spreadsheet. Why starting with your spending habits (not investments) can make or break your retirement success. How to prepare for the emotional side of retirement — including those pesky “what now?” questions. The surprising risks of private equity creeping into your 401(k) — and how to decide if it’s worth it. Smart tax strategies to make your retirement money last longer. How long-term care, market volatility, and unexpected expenses should factor into your plan. Questions to Ponder During the Episode (and discuss with other Stackers!) What’s one spending habit you need to understand now to avoid retirement surprises later? How would you react if your employer added private equity options to your 401(k)? Are you planning your retirement based on your lifestyle — or someone else’s idea of “enough”? FULL SHOW NOTES: https://stackingbenjamins.com/five-steps-to-a-better-retirement-plan-with-jeremy-keil-1743 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think the American Dream is slipping out of reach? Think again. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the biggest financial questions of our time: how much does it really cost to live the life you want — and is it still possible? Spoiler alert: it is, but it takes more than a paycheck and a Pinterest board. We break down fresh research from Investopedia, the rising price tag of everything from healthcare to college, and how smart planning (and a little basement wisdom) can keep your dreams from turning into financial nightmares. But this isn’t just another numbers game. Along the way, the gang shares stories from the road — including Joe’s brush with baseball’s most entertaining team — and digs into the strategies that can help you fight inflation, outsmart rising costs, and make compounding interest your best friend. Plus, we tackle big listener questions, from how to choose the right financial advisor to the best ways to set young adults up for success in a tougher economic landscape. And because life isn’t all spreadsheets and savings goals, we round things out with some binge-worthy TV and movie picks for when you’re off the clock. It’s part money masterclass, part basement hangout — and all about helping you take real steps toward your version of the American Dream. What You’ll Learn in This Episode Why the “American Dream” isn’t dead — but why it may look different today. The real costs behind homeownership, healthcare, education, and retirement (and how to plan for them). Strategies for budgeting, saving early, and building systems that make your money work harder. How to vet a financial advisor and what red flags to watch out for. Smart ways to guide young adults toward financial independence. The power of compounding interest and how to use it to your advantage. Questions to Consider (and Discuss with Fellow Stackers) What does the “American Dream” mean to you — and has that definition changed over time? Which costs (housing, healthcare, college, etc.) feel most overwhelming right now, and how are you tackling them? What’s one piece of financial advice you’d give to someone just starting their journey? FULL SHOW NOTES: https://stackingbenjamins.com/the-rising-cost-of-the-american-dream-1741 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if tweaking just a few “knobs” in your 401(k) could mean the difference between retiring with confidence or wondering if you’ll ever stop working? In this spirited episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by three of our favorite money minds — Paula Pant from AffordAnything, Jesse Cramer from Personal Finance For Long Term Investors, and Lacey Langford from The MILMO Show — to break down everything you thought you knew (and a few things you probably didn’t) about retirement planning. From the basics of employer matches and contribution strategies to the great Roth vs. Traditional debate, we’re exploring the smart moves that can supercharge your 401(k) — and the missteps that can quietly drain your future nest egg. Along the way, you’ll pick up clever tips, a few head-scratching stories, and some beer-fueled trivia that will leave you laughing harder than your HR rep when you ask if “401(k)” is the Wi-Fi password. And because this is Stacking Benjamins, the conversation goes far beyond just investment allocations and tax advantages. We dig into why behavioral traps can derail your savings plan, how military families can maximize their benefits, and why understanding fees is one of the most underrated wealth-building moves you can make. So grab a pretzel, pull up a chair, and let’s talk about how to make your money work harder — so future you can kick back with a stein and say, “I nailed this retirement thing.” How to “tune” your 401(k) like a pro — from employer matches to smart contribution strategies. The real differences between Roth and Traditional accounts (and how to decide which is right for you). Why understanding your 401(k) fees could add thousands to your future balance. How military families can make the most of unique retirement benefits. The biggest mistakes people make with their 401(k)s — and how to avoid them. Plus: A special Oktoberfest-themed trivia showdown and plenty of basement banter. FULL SHOW NOTES: https://stackingbenjamins.com/tweaking-your-retirement-account-1740 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if the secret to enjoying your job isn’t grinding harder but stepping back and rethinking how work fits into life? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome special guest Shemin Nurmohamed to unpack the Paris Paradox: balancing work and leisure without sacrificing ambition. From cultural perspectives on downtime to the productivity perks of unplugging, Shemin shows why working less might just help you accomplish more. But that’s not all. What happens when your financial advisor suddenly jumps ship to another firm? The team digs into what it means for your money, your relationship with your advisor, and how to evaluate whether it’s time to follow—or finally shop around. Add in Doug’s trivia, a few stumbles down random rabbit holes, and our community’s contributions, and you’ve got a lively mix of practical advice and classic basement energy. Whether you’re plotting your next vacation or just trying to figure out how to stop your inbox from running your life, this episode offers real-world strategies (and plenty of chuckles) to help you reset, recharge, and refocus. Why time off is not laziness but fuel for better work and sharper decision-making. How cultural differences around leisure can reshape your own approach. What to do when your advisor changes firms (and how to spot a keeper). Practical ways to build stronger connections and communities. The “Two Beers and a Puppy” test: a surprisingly effective tool for evaluating relationships. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-work-less-live-more-and-love-your-job-1739 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever make a money move in the heat of the moment and wish you could take it back? That’s exactly why a rock-solid Investment Policy Statement (IPS) might be your most underrated financial tool. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug peel back the layers on IPSs—why they matter, how they save you from your own impulses, and the role they play in making sure your investment strategy actually sticks. Think of it as your financial GPS, keeping you on course when market turbulence makes you want to grab the wheel. But it’s not just about avoiding panic-selling. The basement crew digs into the nuts and bolts of what a good IPS should include, from setting specific goals to handling liquidity needs and keeping your risk tolerance aligned with your lifestyle. You’ll also hear how rebalancing, governance, and regular reviews can transform your investments from “hope and pray” into a system you can rely on. Along the way, expect the usual SB tangents: a Joan Jett–themed trivia challenge, a TikTok tale about Apple Pay gone wrong, and more than a few moments where Doug forgets he’s not supposed to run the show. By the end, you’ll not only understand how to create (or update) your IPS, but you’ll also see how it connects directly to building confidence in your financial plan. Whether you’re brand new to investing or a seasoned hand looking to sharpen your strategy, this episode delivers the blueprint. Why an Investment Policy Statement is your best defense against emotional investing How to set clear goals, liquidity rules, and risk guidelines for your portfolio The pitfalls most people overlook when drafting an IPS (and how to avoid them) Smart strategies for rebalancing and reviewing your plan without overcomplicating things A cautionary tale from TikTok that reminds us all to keep our guard up with payment apps Listener Q&A on stock sales and the quirks that come with them Questions You'll Begin to Answer During the Episode: Do you have a written IPS, and if so, does it reflect your actual goals—or just what you thought they were five years ago? What emotional triggers most often tempt you to stray from your financial plan? How often do you review your investments, and is it based on strategy—or headlines? FULL SHOW NOTES: https://stackingbenjamins.com/simple-steps-for-better-money-management-1738 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What happens when you throw a bunch of money nerds into one room, add microphones, and sprinkle in a little economic chaos? You get this live recording from FinCon in Portland, where Joe Saul-Sehy, Paula Pant, Jesse Cramer, and Matthew Tarr tackle today’s most pressing financial questions head-on—with plenty of laughs along the way. From housing headaches to healthcare hurdles, nothing is off the table as the crew breaks down the issues shaping your money right now. Housing prices got you wondering if you should rent, buy, or just live in your car with an Amazon Prime subscription? We dig into the real trade-offs in today’s market. Worried about a looming recession or high-interest rates eating away at your financial confidence? You’ll walk away with strategies that keep you focused and resilient when headlines try to spook you. And for those plotting an early retirement, the group pulls apart the rising cost of healthcare and why conservative investment strategies may be your best friend. At its core, this episode is about tuning out the noise and zeroing in on what matters: a solid plan, smart decisions, and a community of people who know that money is just the tool—not the destination. Whether you’re trying to hit FI, weather market storms, or simply avoid panic-selling your investments, this conversation from the heart of FinCon will leave you with perspective, strategy, and maybe even a grin. Why renting vs. buying isn’t a one-size-fits-all answer (and what today’s market means for you) How to prepare for recession chatter without losing sleep The ripple effect of high-interest rates on your wallet and investments Smart approaches to healthcare planning in early retirement Practical strategies for building a strong investment plan that outlasts market swings Reflections on community, optimism, and financial resilience from the FinCon floor Points to Chew On: Would you rather own a house in this market—or rent and keep flexibility? How do you personally prepare for recession fears without derailing your long-term plan? If healthcare costs keep climbing, how will that affect your retirement timing or strategy? FULL SHOW NOTES: https://stackingbenjamins.com/live-from-fincon-2025-173 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What happens when you stop playing it safe and start playing it smart? In this episode, Joe Saul-Sehy, OG, and Neighbor Doug sit down with David Gardner, co-founder of The Motley Fool, to explore how breaking traditional investing “rules” can sometimes lead to the biggest wins. From his early career to building a community of investors who think differently, David shares the lessons that shaped his approach and why focusing on long-term investing (with a dash of joy) is the key to building wealth. This isn’t just theory—David opens up about the real-world evolution of financial advice, the importance of conscious capitalism, and why advisors need to shift from just picking stocks to becoming true guides in an era where investment products are commodities. Along the way, the basement crew mixes in a few unexpected detours (yes, including some movie talk), reminding us that money doesn’t have to be boring to be meaningful. If you’ve ever felt like the “safe” path with your money was leading you in circles, this episode offers a fresh perspective from one of the most influential voices in modern investing. Get ready to rethink the rules, laugh along the way, and come away with strategies to make your portfolio—and your life—more rewarding. Why breaking conventional investing “rules” can sometimes be your best move The evolution of The Motley Fool and its impact on everyday investors How long-term thinking beats short-term noise in building wealth The role of conscious capitalism and why businesses matter beyond profits Why financial advisors need to pivot their focus to guidance, not just products How criticism shaped David Gardner’s career and what he learned from it Points to Ponder During the Episode When’s the last time you broke a “money rule,” and did it pay off—or backfire? Do you believe financial advisors should focus more on guidance than investment selection? What’s one company or stock you’ve stuck with long-term—and why? Learn more about your ad choices. Visit podcastchoices.com/adchoices

What really derails retirement dreams? Spoiler alert: it’s not always the stock market or your 401(k). Sometimes it’s sneaky habits—like leaning too hard on your house as a retirement plan or ignoring how long you might actually live—that quietly gnaw away at your financial future. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug dig into the most common middle-class retirement killers and how you can sidestep them. But this isn’t your average checklist of “don’t do that.” The team dissects questionable advice floating around internet forums, debates stock splits and diversification, and even finds time to unravel why owning a cat might make you a magnet for gangster-level problems. Add in Doug’s trivia about a famous singer’s real name, and you’ve got an episode that’s equal parts practical and delightfully unpredictable. Whether you’re worried about stretching your retirement savings or just looking for sharper ways to think about financial advice, this episode offers both reassurance and reality checks. So grab your favorite mug (or maybe your cat), settle into your seat, and get ready to learn how to protect your retirement from the biggest threats—while laughing at the absurdity along the way. What You’ll Learn in This Episode: The habits that quietly sabotage retirement plans (and what to do instead) Why your house may not be the slam-dunk retirement strategy you think it is The risks of living longer than you expect—and how to plan for it How to sniff out sketchy financial “tips” before they lead you astray The surprising traps behind stock splits, diversification myths, and overconfidence Why even well-meaning advice can backfire if you don’t look at the big picture Questions to Ponder (or Debate in the Basement Facebook Group): Which retirement habit do you think trips people up the most—and why? If you had to choose, would you rather rely on your house equity or a diversified portfolio to fund retirement? What’s the worst financial “tip” you’ve ever heard online (or maybe even followed)? FULL SHOW NOTES: https://stackingbenjamins.com/habits-that-destroy-middle-class-retirement-dreams-1736 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If having more money guaranteed happiness, we’d all just set our financial targets, cash the checks, and live joyfully ever after. But as Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Joel Larsgaard (How to Money) unpack in this lively roundtable, life’s richest rewards often have little to do with your net worth. They explore why some wealthy people still feel miserable, how Benjamin Franklin’s approach to living can still teach us a thing or two, and why optimism may be your secret investing edge. From the science that says peak life satisfaction might just happen around age 70, to the underrated role of good friends in a rich life (financially and emotionally), this episode blends timeless wisdom with modern money smarts. Whether you’re chasing financial independence, already there, or just trying to make sure your journey is as fulfilling as your destination, you’ll find ideas you can put into practice right now. And because this is the basement, expect the conversation to meander into relatable stories, some eyebrow-raising trivia, and a few debates on what balance really looks like when you factor in both spreadsheets and smiles. What You’ll Learn in This Episode: Why money alone won’t guarantee happiness (and what really does) How Benjamin Franklin’s life principles still apply in today’s financial world The connection between optimism and long-term investing success The surprising age when happiness may peak (and what to do before you get there) How to balance financial independence with enjoying the present Why strong social circles are a must-have part of your wealth plan Questions to Ponder (and maybe share your answers with the Basement Facebook Group!): Do you think your happiness will peak at a certain age—or is it more about circumstances? How do you balance saving for the future with enjoying your money today? What’s one small, intentional change you’ve made that had a big impact on your happiness? Learn more about your ad choices. Visit podcastchoices.com/adchoices

What can you learn about leadership from someone who’s served four U.S. Presidents, navigated some of the most intense moments in American politics, and still believes the future depends on building more leaders, not fewer? In this Greatest Hits Week replay, Joe Saul-Sehy, OG, and Neighbor Doug welcome David Gergen—former White House advisor, Harvard professor, and author—to the basement for a masterclass on leadership that applies as much to your career and investments as it does to running a country. Gergen pulls back the curtain on life inside the White House, from the early lessons he learned in the Navy to the behind-the-scenes moments that revealed the human side of Presidents. Along the way, he shares what separates great leaders from the rest, how to evaluate leadership in others (and yourself), and why service and responsibility are the cornerstones of lasting influence. Whether you’re leading a team at work, managing your family’s financial future, or just trying to be the kind of person others trust, you’ll find plenty here to sharpen your approach. And because no visit to the basement is complete without some SB-style surprises, you’ll also hear stories of presidential humor gone sideways, a White House prank or two, and reflections on how good leadership isn’t about perfection—it’s about purpose. Plus, the guys tackle a listener question on investing without specific goals, and Doug tests the panel’s trivia chops with a leadership twist. What You’ll Learn in This Episode: How David Gergen defines real leadership (and how it’s changed over time) The telltale signs you’re working with—or for—a great leader Lessons from the Navy, the West Wing, and history’s most memorable leaders Why building leaders is just as important as being one Practical ways to evaluate leadership in politics, business, and investing How a clear sense of service can make you a better investor and decision-maker Questions for you while you listen (share with our Facebook group!): Who’s the best leader you’ve ever worked for, and what made them stand out? How do you evaluate whether someone is worth following—whether in politics, business, or life? What’s one leadership skill you wish more people would develop? Learn more about your ad choices. Visit podcastchoices.com/adchoices

Not all financial advisors are created equal—and some will steer you straight into the rocks while smiling the whole way. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug share the top five warning signs your advisor may not have your best interests at heart. From shady investment recommendations to fee structures that deserve a magnifying glass, we unpack the behaviors and practices that can quietly drain your portfolio. This isn’t just about avoiding bad actors—it’s about knowing what great advice looks like so you can spot the difference. You’ll hear why “fun money” accounts can be a trap, how to sniff out overly speculative pitches, and why transparency isn’t optional when it comes to your financial future. Along the way, we sprinkle in a few stories, historical nuggets, and plenty of those classic “Doug moments” that make a trip to the basement worth your time. If you’ve ever wondered whether your financial guide is truly on your side—or if you just want to sharpen your radar—this episode will give you the practical tools to tell the difference between a trusted partner and a wolf in a well-tailored suit. What You’ll Learn in This Episode The five biggest advisor red flags that should send you running How to evaluate an advisor’s investment recommendations for risk and suitability Why fee transparency can make or break a relationship The subtle clues in an advisor’s office environment and interactions The difference between fun money accounts and dangerous speculation How to ensure your advisor’s plan matches your long-term goals Questions to Think About: When’s the last time you reviewed exactly how your advisor gets paid? Are you clear on the why behind each investment they’ve recommended? Would you feel confident explaining your advisor’s strategy to a friend—or does it sound like a foreign language? This episode originally aired on August 2, 2023. Please disregard any mention of current events. You can find the original show notes here. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-spot-a-subpar-advisor-greatest-hits-week-1732 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever celebrate paying off a credit card…only to watch your credit score drop? Or ditch your budget for “simplicity” and find yourself ordering takeout three nights in a row? On this week’s episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant (Afford Anything) and Jesse Cramer (Personal Finance for Long-Term Investors) to explore why even the “right” financial moves can sometimes lead you straight into a banana peel. From the hidden traps of credit scores and debt freedom to the way a shiny new credit card reward program can cost you more than you bargained for, this roundtable digs into the ripple effects that don’t make the brochure. We’ll tackle when “optimizing” your plan goes too far, how well-meaning programs can backfire, and why the metric you’re tracking might not be the one that actually matters. Expect sharp insights, lively debate, and tips you can put into action—without getting tangled in the very strategies meant to help you. Because money confidence isn’t just about making the right moves…it’s about knowing what those moves might do next. We'll Cover: Why your credit score might drop after paying off debt—and why that’s not always bad news How “budget hacks” can turn into budget headaches The sneaky ways credit card rewards and government programs can backfire Why tracking the wrong measure can lead to the wrong results Practical steps to sidestep the unintended fallout from good decisions Questions to Ponder During the Episode What’s the most surprising “side effect” you’ve experienced after making a smart money move? Have you ever optimized your budget or investment plan…only to regret it? Which metric do you track most closely in your financial life—and is it actually the right one? FULL SHOW NOTES: https://stackingbenjamins.com/unintended-credit-score-consequences-1732 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What happens when you hand the mic to Stackers? You get a mailbag episode loaded with real-life money challenges, surprising lessons, and a few “wait, what?” moments. Joe Saul-Sehy, OG, special guest Anna Allem (a CFP® with her own winding journey into the profession), and Neighbor Doug dig into your most pressing financial questions—no fluff, no jargon, and definitely no shortage of basement-style tangents. This week’s listener lineup serves up a buffet of topics: how to turn an HSA into a stealth retirement account, whether a Roth conversion is the right move (and when), the tricky little details that make or break a trust, and what’s happening in the ever-shifting world of auto insurance. Along the way, we get into the mental game of money—why positive thinking might be more than motivational fluff—and how planning isn’t just about the plan on paper. From Anna’s seasoned perspective to OG’s no-nonsense approach and Joe’s knack for cutting through the noise, you’ll walk away with strategies you can actually use. Plus, we can’t resist a detour into AI at the Wendy’s drive-thru (yes, it’s a thing), proving once again that money talk is always better when you leave room for curiosity. What You'll Learn This Episode: How to decide if a Roth conversion makes sense for your tax picture Ways to supercharge an HSA for long-term wealth (and not just medical expenses) Trust basics you might be overlooking—and why that could cost you. The latest trends in auto insurance and how they might affect your rates Why mindset matters just as much as math in building financial confidence Questions to Ponder (or Argue Over in the Basement) If you were starting an HSA today, how would you use it—medical safety net or stealth retirement account? Have you considered a Roth conversion? What’s the one factor holding you back? When it comes to trusts, do you prefer to keep heirs in the loop or keep plans private until needed? How do you decide when to update your insurance coverage versus just shopping for a better rate? FULL SHOW NOTES: https://stackingbenjamins.com/questions-from-the-stacker-community-1730 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Labor Day might be about rest, but in the basement, we’re getting to work on busting some of the most persistent myths in personal finance. Joe Saul-Sehy and OG welcome insurance pro Tony Steuer to unpack the shiny marketing around infinite banking and velocity banking. Spoiler: sometimes “be your own bank” really means “make your insurer rich.” From permanent life insurance pitfalls to the real math behind these strategies, Tony helps separate clever sales pitches from solid financial planning. Then we shift gears to a conversation every parent, grandparent, and future gift-giver will love. Renowned financial journalist Chuck Jaffe joins the crew, fresh from becoming a grandfather, to share how he’s setting his new grandchild up for a strong financial future. Think stock portfolios for toddlers, early Roth IRA strategies, and simple systems that keep family generosity from getting lost in the shuffle. His practical, battle-tested tips will have you thinking differently about the best ways to give kids a head start. Whether you’re looking to avoid costly detours or create generational wealth, this episode is equal parts cautionary tale and inspiration. You’ll walk away ready to dodge financial traps, build smarter for the next generation, and maybe even rethink your own long-term giving plans. Why infinite and velocity banking aren’t the slam-dunk solutions they’re often sold as How to spot the red flags in permanent life insurance pitches Smart, tax-efficient ways to save for children and grandchildren Creative strategies for gifting assets that grow with the child The importance of balancing generosity with your own long-term goals Ideas to Ponder During Today's Episode Have you ever been pitched an “innovative” financial strategy that didn’t feel quite right? What tipped you off? What’s the most meaningful financial gift you’ve ever given—or received—as a child? If you could give one piece of financial wisdom to the next generation, what would it be? FULL SHOW NOTES: https://stackingbenjamins.com/permament-life-insurance-and-growing-your-money-1729 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why wait until your knees creak louder than your rocking chair to start enjoying life? In this episode, Joe Saul-Sehy, OG, Paula Pant (AffordAnything) and Neighbor Doug welcome Jillian Johnsrud—author of Retire Often—to share why sprinkling your life with mini-retirements might be the smartest, healthiest, and most joyful move you make before your “official” retirement date. Think of it as giving your future self a head start… without the Medicare paperwork. From negotiating time off without burning bridges, to building a financial plan that lets you step away without panic, Jillian offers a roadmap to hit pause on your career without pressing stop. We explore the balance between health, capability, and the freedom to explore, and how to sell the idea of a mini-retirement to your boss so they don’t see it as a resignation letter in disguise. And because it’s the basement, we also mix in some Labor Day trivia, a few personal experiments with unconventional choices, and just enough playful banter to keep you leaning in. If you’ve ever felt the grind wearing you down but can’t picture walking away forever, this episode will help you reimagine your work-life timeline. Mini-retirements aren’t just for the wealthy or the whimsical—they’re for anyone ready to start living a retirement-worthy life now. How to pitch a mini-retirement to your boss without triggering an awkward HR meeting The financial prep work that makes time off less stressful and more satisfying Ways to test-drive retirement before the “official” date How to handle the skeptics (at work and at home) who think you’re making a mistake Why health and capability should be part of your retirement timing equation Questions to Ponder While You Listen If you could take 3–6 months off tomorrow, how would you spend it? Would a series of shorter retirements feel more fulfilling than one long one at the end? What’s the biggest barrier—financial or otherwise—keeping you from taking a break? Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you’ve been running on fumes, juggling work deadlines, family obligations, and maybe even a neglected 401(k) or two, this episode is your permission slip to stop, breathe, and recalibrate. Joe Saul-Sehy, OG, and Neighbor Doug welcome Dr. Danielle McGeough—professor, transformational strategist, and champion of intentional living—into the basement for a conversation that’s part burnout intervention, part life strategy workshop. Dr. McGeough shares how to spot the early signs of burnout before you hit the wall, and how to rebuild your days with personal rituals, playfulness, and values-driven planning. You’ll hear real-world strategies for setting boundaries, aligning work with what truly matters to you, and bringing joy back into your calendar. And because we’re in the basement, we also manage to sneak in some Labor Day trivia, a Broadway tangent, and a solid helping of SB-style banter. And for the Stackers worried about the financial side of burnout, we pivot in the second half to a practical discussion on managing multiple 401(k) plans—because a cluttered retirement portfolio can be just as stressful as a cluttered schedule. From account consolidation tips to understanding your investment options, this is a one-two punch of mental clarity and financial order. How to recognize the red flags of burnout (and stop it in its tracks) Why personal rituals and play can fuel productivity and joy How to align your schedule with your core values Strategies for balancing ambition with sustainability Practical steps for managing multiple 401(k) plans without losing track Why decluttering your finances can boost your mental clarity Thoughts to Ponder During the Episode What’s one personal ritual you could add to your day that would give you energy instead of draining it? Have you ever consolidated old retirement accounts? What made you decide to do it (or not)? How do you know when you’ve hit your “enough” point with work and need to reset? What’s one value you’d like to see reflected more clearly in your daily life? FULL SHOW NOTES: https://stackingbenjamins.com/how-to-reset-with-clarity-and-purpose-1727 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever think, “If I just followed the playbook of the ultra-wealthy, I’d be set for life”? Turns out, that’s exactly the kind of thinking that can lead you straight into the arms of a scammer. In this episode, Joe Saul-Sehy and OG break down the traps hidden inside the “invest like the 1%” mantra (and other similar phrases), complete with real-life cautionary tales, including a small-town Ponzi scheme that could’ve been ripped from a Netflix docuseries, and the spectacular belly flop of some YieldStreet real estate bets. But it’s not all doom and gloom in the basement. You’ll also get the scoop on a controversial proposal to let private equity sneak into your 401(k), practical tips for spotting shady pitches before they drain your wallet, and the reminder that a boring-but-solid financial plan beats a flashy scam every time. Plus, the guys field a listener question on long-term care insurance and unpack the often-overlooked basics of HSAs. Between headlines, trivia detours, and a dash of movie talk, this episode arms you with the street smarts to dodge the next “too good to be true” investment opportunity. It’s a masterclass in protecting your money—without having to hide it under your mattress. The psychological tricks scammers use to lure in even savvy investors Why “invest like the 1%” can backfire for everyday Stackers How to evaluate alternative investments (and when to walk away) The risks and realities of adding private equity to retirement accounts Key questions to ask before buying long-term care insurance Why a strong, clear financial plan is your best defense against cons Questions to Ponder During Today's Show: Have you ever been tempted by an investment pitch that felt “exclusive”? Would you want private equity options inside your 401(k)? Why or why not? How do you decide whether an alternative investment is worth the risk? What’s your personal “red flag” that makes you walk away from a deal? FULL SHOW NOTES: https://stackingbenjamins.com/how-to-avoid-common-rip-offs-1726 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you’ve ever wondered whether you should pass on your money now or make your heirs wait for the “big reveal” (cue the dramatic reading of your will), this is your episode. Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant from Afford Anything and Jesse Cramer from Personal Finance for Long-Term Investors to play a high-stakes round of “In or Out” with estate planning and charitable giving. Is anonymous giving a waste of good publicity? Should you set up a donor-advised fund or keep it simple? Is sharing your estate plan with your heirs wise—or an invitation to awkward holiday dinners? This isn’t your average dry legal seminar. Between football analogies, dinosaur jokes, and the occasional jab at Ford’s electric truck sales, our crew digs into the real-life choices Stackers face when deciding how—and when—to pass along their wealth. You’ll hear hot takes, smart strategies, and maybe even a nudge to start that conversation you’ve been putting off. From the practical (avoiding probate, maximizing giving impact) to the philosophical (why give at all, and how much?), this episode blends useful tactics with the irreverent basement energy you know and love. It’s part money talk, part game show, and 100% designed to get you thinking about your financial legacy. The pros and cons of giving now versus after you’re gone How donor-advised funds work and whether they’re worth your time Why anonymous giving might be overrated—or a hidden superpower Ways to avoid family drama by (maybe) sharing your estate plan early How to think about charitable giving as part of your overall financial plan Questions to ponder during the show: Would you rather give now and see the impact, or give later and leave a surprise? How much transparency do you think heirs deserve about your estate plans? If you give anonymously, are you missing an opportunity—or dodging a headache? What would you want your charitable legacy to look like? FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-giving-week-in-or-out-1725 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if there were a way to make charitable giving easier, more strategic, and—dare we say—more satisfying? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Len Penzo welcome Adam Nash, founder and CEO of Daffy, to demystify donor-advised funds. Whether you’ve never heard of them or you’ve been meaning to set one up, Adam walks us through how they work, why they might be a perfect fit for your giving goals, and how they can help you be more intentional with your generosity year-round. But that’s not all—we also turn the spotlight on an often-overlooked money moment: handling a car insurance claim. From gathering evidence at the scene to negotiating with your insurance company, the team shares smart, practical steps to make sure you don’t leave money (or protection) on the table. And, of course, Len dishes up his trademark personal finance storytelling straight from his new book, mixing in lessons you’ll actually remember with tales you didn’t see coming. If you’ve been thinking about giving more, protecting yourself better, or just want to walk away with some clever, real-world money moves, this episode’s got you covered. Plus, you’ll leave with an extra nudge to make your charitable giving—and your financial safety net—as strong as possible. What You’ll Learn in This Episode: The basics of donor-advised funds and how they can supercharge your charitable giving Key differences between donor-advised funds and traditional giving methods How to prepare for and navigate a car insurance claim from start to finish Smart moves for documenting accidents and protecting yourself against disputes Why diversification in your giving can be as valuable as diversification in your investing How Len Penzo turns everyday money lessons into stories you’ll want to retell Questions to Discuss with Your Fellow Stackers: Have you ever used a donor-advised fund—or would you consider one after hearing this episode? What’s one lesson you’ve learned (the hard way or otherwise) from filing an insurance claim? Do you think giving should be a scheduled part of your financial plan, or something you do more spontaneously? FULL SHOW NOTES: https://stackingbenjamins.com/donor-advised-fund-deep-dive-1724 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Estate planning might not sound like the most thrilling topic—but skipping it can create a real mess for the people you care about most. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug sit down with attorney Tim Semro to cut through the noise on wills, trusts, and life insurance. Whether you’ve been putting off writing a will or you’re wondering if a trust is worth it, this conversation will give you a clearer path forward. Tim walks us through the essentials, from the differences between wills and trusts to the sneaky pitfalls that can trip up your beneficiary designations. We also tackle tricky scenarios—like probate headaches, planning across state (or even international) lines, and how to think about life insurance with living benefits. Plus, we swap stories about scams that hit a little too close to home and the simple moves you can take to protect your finances and family. This episode isn’t about scaring you into action; it’s about showing how estate planning and the right insurance can actually bring peace of mind. By the time you’re done listening, you’ll have a roadmap for protecting your family, making smarter decisions with your money, and avoiding the landmines that could derail your plan. And yes, there’s still a trivia break and plenty of the usual basement flavor to keep things moving. What You’ll Learn in This Episode: The key differences between wills and trusts—and when you might need each Why beneficiary designations matter more than you think How estate taxes and probate rules can complicate things (and how to prepare) What life insurance with living benefits is—and when it could make sense Red flags for spotting scams and fraud before they hit your wallet How to align your estate plan with your financial and family goals Questions to Ponder While You Listen (and maybe discuss with us in the Basement Facebook Group): Do you already have a will or trust in place? If not, what’s been holding you back? Have you ever discovered an outdated beneficiary designation (or seen the chaos it caused)? What role do you think life insurance should play in your estate planning? FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-charitable-giving-week-1723 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Some people chase “work-life balance” like it’s the Holy Grail—spending time, money, and mental energy trying to keep work and personal life perfectly split down the middle. But what if that balance doesn’t actually exist? Live from Joe’s mom’s basement (and not nearly as glamorous as it sounds), Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer pull back the curtain on whether we should be aiming for balance… or something else entirely. In this roundtable, the crew wrestles with the difference between work-life balance, alignment, and integration—and why chasing balance might actually keep you from a truly fulfilling life. You’ll hear personal stories, some hard-won lessons about productivity, and a few well-placed digs at Nautica (including the questionable financial moves Joe made in his youth). And because no basement chat is complete without it, we bring you a trivia challenge you didn’t know you needed. From managing notifications so they stop managing you, to building a life where work and personal priorities don’t compete, this episode digs into the practical steps that help you get more out of both your career and your free time. Whether you’re climbing the corporate ladder, running your own show, or plotting an early retirement, you’ll walk away with tools to rethink how you spend your hours—and why. What You’ll Learn in This Episode: Why “work-life balance” might be the wrong target—and what to aim for instead The difference between balance, alignment, and integration (and why it matters) Practical ways to keep work from swallowing your personal life whole How to reclaim your attention from constant notifications and distractions Mindset shifts that boost productivity and satisfaction in everyday life Lessons from real-life wins and missteps (including Joe’s Nautica saga) FULL SHOW NOTES: https://stackingbenjamins.com/all-about-work-life-balance-1722 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder how to build a career, business, or financial plan that actually lasts — no matter what life throws at you? This week, we’re bringing you lessons from someone who’s done it for more than five generations. Cheryl McKissick Daniel, president and CEO of McKissick & McKissick, joins Joe and OG to share the strategies her family has used to overcome obstacles, land major deals (like the arena in Brooklyn and countless buildings on the historic register of places), and turn connections into opportunities. Whether you’re growing a business, climbing the career ladder, or managing your money, you’ll walk away with practical ideas to strengthen your network, protect your reputation, and keep moving forward. From the art of negotiation to turning big challenges into bigger wins, Cheryl offers insights you can use right now to build momentum. We’ll explore how revisiting your financial plan regularly can help you avoid surprises, why reputation is an asset you can’t afford to neglect, and how a strong team can take you further, faster. Plus, we’ll take a break for our TikTok Minute to look at what happens when your vacation budget disappears in the name of “fun” spending. And in our headline segment, we’ll cover important Medicare and insurance updates that could save you money and headaches later. Here’s what you’ll learn in this episode: How to use your reputation as a currency that opens doors and attracts opportunities Strategies for building a network that works for you (even when you’re not in the room) Lessons from landing multi-million-dollar deals — and how to apply them to your own negotiations Why regularly reviewing your financial plan can save you from costly surprises Smart adjustments to Medicare and insurance that protect your money and peace of mind How to turn adversity into momentum, whether in your career or personal finances A lighthearted look at how “just a little fun” can destroy your budget faster than you think FULL SHOW NOTES: https://stackingbenjamins.com/story-about-building-america-1721 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is your 401(k) quietly working for you… or quietly working against you? In the first half of this episode, Joe Saul-Sehy, OG, and Neighbor Doug tackle the most common 401(k) slip-ups that even seasoned savers make—and how to turn yours into a retirement-building machine. Then, in the second half, we turn to a problem many Stackers don’t see coming: going from saving to spending in retirement. Stacker Joel in Cleveland asks how to make the leap without feeling like you’re sabotaging your future. Drawing on OG’s real-world experience guiding clients through this tricky transition and Joe’s research into the psychology of money, we share practical steps to help you spend without guilt, align your withdrawals with your values, and actually enjoy the freedom you’ve worked so hard for. Here’s what you’ll learn in this episode: The most expensive 401(k) mistakes—and how to fix them today Why employer matches are truly “free money” (and how to grab them) Smart moves for rolling over old 401(k)s and navigating vesting schedules The pros and cons of holding company stock in your retirement account Why the saving-to-spending switch can feel so uncomfortable—and how to get past it A simple mindset shift that helps retirees live more fully without blowing their plan How to turn your nest egg into a joy-producing income stream Whether you’re in the middle of your career or staring down your first year of retirement, this episode will help you protect what you’ve built, optimize your plan, and make the most of your money—without second-guessing yourself. FULL SHOW NOTES: https://stackingbenjamins.com/common-401-k-mistakes-1720 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Get ready for a rapid-fire roundtable packed with personal finance opinions that might challenge your own money playbook. In this episode, Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Don McDonald (Talking Real Money) join Joe and OG to declare whether they're in or out on some of the most polarizing financial strategies. Whether you're just getting started or leveling up your financial life, this episode is full of practical wisdom, contrarian views, and a few laughs along the way. Oh—and somewhere in there, we may or may not sneak in a birthday surprise for one of our favorite Stackers. 🎂😉 Why some pros still say "cash only" is best for beginners—and why others strongly disagree The real trade-offs of delaying homeownership in today’s market What types of insurance you actually need (and which may just be money drains) When hiring a CPA is a gamechanger vs. when it's overkill How to evaluate target date funds: genius or lazy? Whether it’s finally time to drop collision insurance on that 15-year-old car How to choose between Roth and Traditional 401(k) strategies The one estate planning move nearly everyone overlooks FULL SHOW NOTES: https://stackingbenjamins.com/jeff-lund-birthday-special-1719 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think negotiation is just for boardrooms and car dealerships? Think again. In this episode, we bring in Paula Pant from Afford Anything to show how negotiating—done well—can level up your finances, your relationships, and yes, even who does the dishes. Paula breaks down why many of us fear negotiation, how to overcome those internal roadblocks, and how setting clear “aspiration” and “reservation” points can lead to more confident conversations (and better outcomes). Whether you’re asking for a raise or trying to avoid unloading the dishwasher for the fifth night in a row, her tactics are practical and empowering. Also in this episode: What most people miss about their workplace retirement plans, and whether adding a managed account is the edge you’ve been missing A viral TikTok proposal on setting your kids up for millions—can it really work, or is it just social media smoke? Doug delivers trivia and 1970s television references like only he can And we remember a cherished interview, David Gergen This episode is packed with useful strategies, real talk, and a few basement detours—including mafia negotiations, Lucille Ball’s business savvy, and a heated debate over nostalgic TV shows. Whether you’re trying to grow your wealth, negotiate more confidently, or just dodge financial TikTok traps, we’ve got something in here for you. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-improve-your-negotiating-skills-with-paula-pant-1718 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is your grocery bill beefier than your sandwich? This week, Joe Saul-Sehy, OG, and Neighbor Doug unpack inflation in a way that only we can—by biting into Len Penzo’s Annual Sandwich Survey. Yes, prices are up, and yes, you can still eat well without triggering a credit card crisis. But it’s not just meat and mustard on today’s menu. We’re also serving a fresh look at 401(k) “leakage”—that drip-drip-drip of hardship withdrawals that's turning your retirement plan into a leaky faucet. You’ll get pro-level insight on how to patch those holes before your future income soaks the floor. And if you’re paying for (or dreading paying for) college, Christine from the Stacker community, who works in higher ed, joins to offer sharp and timely advice on keeping costs in check—from completing the FAFSA to finding overlooked aid. Len Penzo’s Sandwich Index Which sandwiches give you the most delicious bang for your inflation-adjusted buck? (Spoiler: bologna stages a quiet comeback.) 401(k) Trouble Brewing Hardship withdrawals are on the rise. Why it matters, how to avoid them, and what better options exist when life throws you a cash crisis. Tracking Expenses Like a Pro Joe, OG, and Doug explore the subtle ways inflation seeps into your budget—and how paying attention to where your money leaks gives you power back. Higher Ed, Lower Bills Stacker Christine breaks down must-know tips on navigating skyrocketing tuition, including a FAFSA pep talk that could save you thousands. Tuna vs. Roast Beef: The Sandwich Showdown Plus: Is the BLT still king? Can the humble tuna salad hold its ground against the mighty Big Mac? And where does salami fit into the sandwich power rankings? Trivia, Movie Talk, and Park City Tales No Stacking Benjamins episode is complete without a detour or three—from Doug’s trivia trap to stories from the road and screen. Takeaway for Stackers: In high-cost times, it’s the small wins—like swapping in store brands, packing a lunch, or tracking that budget leak—that give you the edge. And while it’s tempting to ignore those tiny cracks in your retirement plan or daily spending, you’re much better off fixing them before the flood. Want to brag about your favorite money-saving sandwich? Drop into the Basement Facebook group and share it—bonus points if it doesn’t involve bologna. FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-2025-annual-sandwich-survey-1717 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You just came into $50,000—no strings attached. Do you crush your debt? Supercharge your retirement? Blow it all on a podcasting-themed backyard grotto? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (The Best Interest) gather around the card table in Mom’s basement to tackle one of the most common “someday” questions in personal finance: What do you do when a windfall lands in your lap? Whether it's an inheritance, work bonus, or prize money (maybe you finally won that game show you keep applying to), the panel explores what smart, emotionally grounded, and goal-aligned decisions look like in the face of sudden cash. Start With the Why Before you touch a dime, the crew walks through the importance of mindset, goals, and not falling into the “I deserve it” trap that has sunk many a lucky winner. Debt vs. Invest vs. Enjoy High-interest debt? Retirement accounts? Travel dreams? The panel weighs each strategy—and surprises us with their personal priorities. Behavioral Finance & Windfall Psychology Why do people tend to mismanage unexpected money? From mental accounting to lifestyle creep, learn the hidden traps and how to sidestep them. The 401(k) Match Dilemma Is it better to max out tax-advantaged accounts or build an emergency fund? The team hashes out smart order-of-operations for stacking your windfall right. Trivia Break: St. Paddy’s Parade Edition Neighbor Doug makes sure you don’t learn too much without a little distraction. Can you guess when the first St. Patrick’s Day parade was held? How They’d Spend It Ever wonder what Joe, OG, Paula, or Jesse would do with an extra 50 grand? From practical moves to guilty pleasures, we get a peek into each of their financial brains. Don’t let windfalls drift into “found money” syndrome—align with your long-term goals first. Paying off high-interest debt = guaranteed return. But balance it with your future-focused investments. Emotional awareness is just as crucial as spreadsheets when a windfall hits. Take a beat before making decisions. Give yourself permission to enjoy some of the money—just make sure it’s intentional, not impulsive. Got a windfall story or dream scenario? Tell us how you’d handle an extra $50K in our Basement Facebook group. Let’s see who would invest it, who would renovate the kitchen, and who would finally launch that mobile alpaca petting zoo. FULL SHOW NOTES: https://stackikngbenjamins.com/how-to-treat-a-financial-inheritance-1716 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

High school math left most of us staring blankly at the board, convinced compound interest was just a fancy way to say "confusing." But what if math could be fun, relevant, and—dare we say—life-changing? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome economist, education reformer, and documentary filmmaker Ted Dintersmith to the basement for a conversation that makes math feel less like a chore and more like a cheat code for life. Dintersmith, best known for his education advocacy and the acclaimed documentary Most Likely to Succeed, joins us fresh off the release of his latest book, Aftermath—a compelling look at how we rethink learning in a world that’s evolving faster than ever. With over a decade visiting 500+ schools and a deep passion for practical math, Ted shares how skills like estimation, probability, and prediction can help you make smarter decisions—especially when it comes to your money. Why Prediction Beats Perfection Ted explains why being roughly right about your spending, investing, and life planning is more powerful than being precisely wrong. Consumer Math is the Real MVP From family budgets to grocery store run-throughs, Dintersmith makes a case for math that actually applies to your everyday decisions—and shows how parents and educators can teach it at home. A Fourth-Grade Science Test Gone Wrong An unforgettable story about how one exam nearly crushed a curious kid’s confidence… and what it says about how we measure learning. The Financial Advisor Dilemma Solved Joe Saul-Sehy and OG unpack the key differences between bank advisors and independents, including fee structures, fiduciary responsibilities, and what really matters when choosing your financial guide. Lights, Camera, Reform Dintersmith shares the powerful stories behind his documentaries—including Most Likely to Succeed and the upcoming Multiple Choice—and why his new book Aftermath is a must-read for anyone who believes education should prepare us for real life. The Psychology of Math Anxiety and Money Mistakes We explore how bad math experiences lead to financial decision paralysis, and how to rebuild confidence one calculation at a time. Neighbor Doug’s Trivia Takes the Stage Whether it connects to math or not, Neighbor Doug delivers his signature trivia moment with flair—and possibly a tangent or two. Math shouldn’t be a barrier to better money decisions. This episode arms you with a fresh mindset for yourself, your kids, and maybe even your school board. If you’re a math teacher, financial coach, or just someone who once cried over fractions, we want to hear from you. Join the conversation in our Facebook group, The Basement, and tell us: How are you making math practical—or how do you wish you’d learned it? FULL SHOW NOTES: https://stackingbenjamins.com/math-that-you-need-in-your-life-1715 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Big changes are coming to the tax code—and that could mean big savings if you know where to look. On today’s episode, Joe, OG, and Doug break down the most important updates in the 2025 tax laws and share smart, simple ways to keep more of your hard-earned cash. Whether you're a spreadsheet-loving tax nerd or someone who still asks, “Wait, do I have to file?”—this episode will help you navigate the new rules like a pro. Here’s what we unpack: The 2025 Tax Overhaul: What changed, what stayed the same, and how it affects your bottom line Credits vs. Deductions: Why that $1 credit might be worth more than a $5 deduction (math, but fun) Above-the-Line Moves: Claim valuable deductions without itemizing New Wins for Givers and Drivers: Above-the-line charitable contributions AND (drumroll…) personal auto loan interest is back! Family Tax Breaks: Expanded dependent care accounts and beefed-up child credits 50 and Thriving: New 401(k) catch-up rules that can help you max out your retirement Listener Mailbag: JJ asks how to contribute more to his 401(k) after age 50—and we bring the strategies The TikTok Minute: Because money wisdom can live on the internet too Doug’s Trivia & Financial Shenanigans™: Of course You’ll walk away with clear, practical takeaways that could add thousands to your bottom line—without needing to read the tax code (you're welcome). FULL SHOW NOTES: https://stackingbenjamins.com/upcoming-tax-changes-1714 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if the scariest part of retirement isn’t running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show, we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement. Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers: Mark Trautman (Mark’s Money Mind) Paula Pant (Afford Anything) Jesse Cramer (Personal Finance for Long-Term Investors) Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you're closing in on retirement or still working toward it. The biggest fears about retirement: from running out of money to running out of meaning. The “one more year” syndrome: why it's so tempting to delay and how to break through. Time freedom vs. financial freedom: how to align your life goals with your money strategy. Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental properties. Psychology matters: why no spreadsheet ever solved a midlife identity crisis. Real stories from the panel: wins, struggles, and lessons from guiding others through retirement transitions. Planning for healthcare and long-term care: because your body didn’t get the early retirement memo. Plus, the usual basement mayhem: trivia, playful host banter, and a few unexpected laughs (we won’t call them “funny”—you know the rule). Mark’s Money Mind podcast Afford Anything podcast Personal Finance for Long-Term Investors AARP: Retirement Readiness & Addressing Fear Blog post: “Fear Will Hold You Prisoner. A Diversified Portfolio Will Set You Free.” Retire to something, not just from something. Purpose beats spreadsheets. Understand your income plan. Know where the money will come from, rain or shine. Plan for healthcare now, not later. Medicare, long-term care, and medical surprises deserve your attention. Don’t go it alone. The best plans are ones you understand, but it helps to get advice from trusted sources. Whether you’re on the cusp of calling it quits or still deep in the grind, this episode will help you prepare—not just financially, but mentally and emotionally—for a retirement you’ll love. FULL SHOW NOTES: https://stackingbenjamins.com/what-is-holding-you-back-from-reaching-your-goals-1713 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 🎧 Dive deeper, grab resources, and check out past episodes at StackingBenjamins.com Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do your financial priorities look like when you're just getting started... or when you're sitting on $100 million? If you’re still stuck trying to figure out how to max out your Roth IRA and also afford dinner, this episode’s going to walk you through what might be coming next—without promising you a yacht by Tuesday. This week on The Stacking Benjamins Show, Joe Saul-Sehy, O.G., and Doc G (Jordan Grumet) are joined by Nick Maggiulli, Chief Operating Officer at Ritholtz Wealth Management and author of Of Dollars and Data, to talk about lessons from his new book: The Wealth Ladder. Nick breaks down the six wealth levels, from scraping together your first emergency fund to navigating the complexities of generational wealth. They explore: Why increasing your income early on trumps frugality (sorry, coupon clippers). What “wealth plateaus” really look like, and how to recognize when your strategy needs to evolve. The hidden trap of goal obsession, featuring a cameo from world #1 golfer Scottie Scheffler. The true cost of career choices, and why opportunity cost might be the silent killer of long-term growth. Why content and code are two of the most powerful wealth-building levers available (especially when they scale without needing a lunch break). Whether you're stuck in Level 1 or fantasizing about Level 6, this episode has practical, perspective-shifting advice on building wealth—and more importantly, how to enjoy the process without losing your sense of purpose along the way. Stackers don’t just want to make money—they want to master it without letting it become their master. This conversation bridges income, investing, identity, and intention in a way that gives you both clarity and confidence. You might even stop worrying about skipping that $5 latte… or realize it’s time to start coding that app you keep talking about at parties. FULL SHOW NOTES: https://stackingbenjamins.com/invest-differently-and-move-faster-1712 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What’s the right financial move for you… right now? If you've ever found yourself reading advice meant for a millionaire when you're still trying to crack five figures—or following budgeting tips when your net worth is seven digits—this episode is your custom-tailored financial GPS. In this installment of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug take you rung-by-rung through the wealth ladder—from humble beginnings at $10K all the way to $10 million—and explain how your financial priorities, risks, and strategies evolve as your net worth grows. How to avoid mismatched advice: Why taking financial tips meant for someone in a different stage can set you back instead of move you forward. Net worth brackets and behavior shifts: What you should be thinking about at $10K, $100K, $1 million, and beyond—and what not to worry about yet. When Roth IRA conversions make sense—and when they really don’t: With new legislation impacting retirement tax planning, Joe and OG break down the implications with help from Robert Powell of The Street. Diversification, risk, and behavioral pitfalls: What the pros get wrong and how to stay grounded no matter how big your stack grows. Community-driven insights: From listener milestones to new Stacking Benjamins swag sightings, you’ll hear how Stackers are winning in their own lives. As always, the team weaves in laughter, sarcasm, and that unmistakable basement charm—complete with Doug’s new mug, a calendar confusion history lesson, and a household disaster caused by what can only be described as “revenge rain.” A Robin Williams–themed trivia segment to warm your heart (and test your memory) Batty Betty’s wild TikTok take on relationship finance Practical investing and estate planning ideas that don’t make your eyes glaze over Why You’ll Love This Episode:If you’re trying to level up without falling prey to the one-size-fits-all advice machine, this episode delivers a realistic blueprint. It’s equal parts roadmap and reminder: where you are right now matters more than where someone else thinks you should be. Stacker takeaway? Clarity beats comparison. Especially when it comes to money. FULL SHOW NOTES: https://stackingbenjamins.com/build-your-wealth-ladder-1711 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like you're working hard but getting nowhere? You're not alone—and you might be stuck in a productivity trap, not a purpose-driven plan. In this episode of The Stacking Benjamins Show, we tackle the big one: how to avoid wasting your life. (No pressure.) Joe Saul-Sehy kicks things off with a tongue-in-cheek nod to all the ways we fritter away time—before pivoting into a power-packed conversation on building meaningful goals and avoiding common life derailers. He’s joined by two all-star minds in money and behavior: Paula Pant from Afford Anything, who reminds us that "you can afford anything—but not everything," and Jordan Grumet from Earn & Invest, who offers the life-and-death perspective (literally—he’s a hospice doctor) on why we need to act now, not later. Together with OG and Doug, the roundtable unpacks six common ways people unknowingly waste their lives, including: Being "busy" instead of effective Letting fear of failure hijack your plans Overthinking every move Paralysis from too many choices Constant hustle with no progress Indecision dressed up as careful planning You’ll hear hard-earned lessons, subtle mindset shifts, and tips for creating financial and personal momentum. Plus: The surprising link between indecision and regret, backed by Dr. Ellen Langer’s research Smart strategies for eliminating distractions and taking better action The difference between motion and movement—especially when it comes to your goals and your money And, of course, we sprinkle in some classic basement banter, a rowdy trivia throwdown, and Joe’s favorite kind of weekend preview (the kind where no one actually follows their own advice). Why this episode is worth your time: Whether you’re staring down your 2025 goals or still recovering from a rough Q1, this is your shot of clarity. No judgment—just real talk from people who’ve been there, made the spreadsheet, and occasionally lit it on fire. 🎯 You’ll walk away with: A clearer idea of what’s holding you back Practical ways to structure smarter financial goals Permission to stop doing all the things and start doing the right things FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-waste-your-time-on-stupid-stuff-1710/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Want to crush your goals and avoid getting crushed by long-term care costs? In today’s episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Retired Lieutenant Commander Gary McDermott, a former U.S. Navy officer turned business coach, who brings military-grade discipline to the world of goal-setting and financial success. Whether you’re working toward a promotion, launching a side hustle, or just trying to stay on track past February, Gary shares a field-tested, civilian-approved approach to achieving your biggest financial and personal milestones. From defining SMART goals to building sustainable habits and multiple income streams, this conversation is all about real results—no fluff, no buzzwords. But that’s just the first mission. In the second half, Joe and OG dive into one of retirement’s trickiest topics: long-term care insurance. Is it worth it? When should you buy it? How do you know if it’s right for your situation? Consider this your tactical briefing before walking into a battle you didn’t know you were fighting. You’ll also hear: Why borrowing someone else’s goals is a recipe for burnout. The power of structure and accountability (no drill sergeant required). What “Trump Accounts” are and why you might want to know about them. How to evaluate long-term care coverage before it sneaks up on your plan. Joe’s high-speed review of the new Formula One movie (spoiler: he’s not drafting behind the popcorn). Packed with tactical advice, unexpected laughs, and practical strategies, this episode delivers a full-stack toolkit for Adventurers looking to thrive—financially and personally—in the second half of 2025 and beyond. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-set-and-achieve-your-goals-gary-macdermid-1709 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Still on track to crush your 2025 goals? Or has the year felt more like a Super Mario Kart banana peel moment? In this special mid-year review episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG take a pause from the summer sprint to look back at the most impactful lessons, conversations, and themes from the first half of 2025. Whether you’re rethinking your budget, fine-tuning your risk tolerance, or just trying to remember where you wrote down your resolutions, this is your nudge to hit the financial reset button—with style. From Alex Hormozi’s take on embracing risk and skill-building to JL Collins' wisdom on why buying happiness with money is a flawed formula, this episode pulls powerful insights from our brightest guests so far. We revisit career advice from media powerhouse Bonnie Hammer, dig into intentional spending habits, and reflect on the subtle connection between mindset and long-term success. Oh—and don’t miss a moment of Joe and OG’s always-wise, occasionally-weird banter as they break down topics like: Why goal setting isn’t just for January—and how to mid-course correct before December sneaks up on you. Risk management in real life (not the textbook version). Why mindful consumption isn’t about cutting back, but tuning in. What makes retirement joyful beyond the spreadsheets. How your community can be the most underrated part of your portfolio. If you’ve felt a little off-course—or just want a chance to recalibrate without the guilt trip—this episode delivers practical steps and encouraging reminders to help you make the second half of 2025 your strongest yet. Got goals? Let’s reset ‘em. And if not, we’ve got a few ideas for those, too. FULL SHOW NOTES: https://stackingbenjamins.com/our-review-of-first-half-2025-1708 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is your house full of stuff you thought you needed… but haven’t touched since the Obama administration? In this game show-style episode, we're helping you clean house and bulk up your bank account at the same time. Joining Joe in the basement are Paula Pant from Afford Anything, OG, and the man, the myth, the TikTok-famous legend’s grandpa’s best friend: Len Penzo (or as Doug calls him, “America’s Most Unexpected Influencer”). Together, they go head-to-head in a raucous showdown, each offering hot takes on everyday items you should stop buying if you want to save money and ditch the clutter. We dig into: Why some exercise equipment becomes expensive coat racks The hidden costs of seasonal decorations Periodicals, subscriptions, and other budget vampires And a few “who knew?” items that quietly drain your cash You'll also get a dose of trivia, debates about Google's "search decay," and a few personal stories that might sound a little too familiar. Whether you’re decluttering your budget or just here for the basement chaos, this episode is full of laughs, lightbulb moments, and ideas to help streamline your spending. FULL SHOW NOTES: https://stackingbenjamins.com/decluttering-your-financial-life-greatest-hits-1707 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if your money could bring you more joy—and less stress? Today, we welcome Ken Honda, Japan’s bestselling personal development guru, to the basement. He introduces us to his concept of “Happy Money,” where gratitude replaces fear, and your relationship with money becomes… well, happier. From early lessons in emotional finance to wisdom from his own mentors, Ken shares how small mindset shifts can lead to big life changes. But before we get zen with our Benjamins, Joe and OG shine a light on the latest investigation into real estate commissions. Are hidden fees quietly draining your wallet when you buy or sell a home? The Justice Department seems to think so. We dive into what’s happening—and what you can do about it. Also in the episode: HSA contribution limits are rising—are you using your health savings account the smart way? A listener wonders if hiring their kids can unlock Roth IRA opportunities (spoiler: it’s not as simple as “just write them a check”). Doug moonshines a trivia question that may or may not involve death (but definitely involves Doug). Whether you’re looking for practical strategies or a new perspective on money itself, this episode brings both insight and inspiration. FULL SHOW NOTES: https://stackingbenjamins.com/happiness-with-ken-honda-greatest-hits-1706 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is your home packed with emotional baggage... and maybe a few fondue sets you haven’t touched since 2003? Organizational expert Tracy McCubbin joins us to talk about the emotional side of clutter—why it builds up, how it weighs us down, and what to do when your sentimental stuff is quietly running the show. Meanwhile, Joe and OG dig into another kind of mess: the billions retirees lose by claiming Social Security too early. Timing isn’t just everything—it’s the difference between thriving in retirement and wondering where all the money went. In this episode, we cover: Why sentimental clutter is more than just "stuff"—and how to finally let it go. How donating intentionally can breathe new life into your old things (and clear some mental space). The tough conversations adult kids need to have with parents about downsizing and letting go. Strategies to help you avoid making costly Social Security decisions. A surprisingly thoughtful take on the Taco Bell Hotel (yes, it’s real... and yes, it sold out in minutes). Plus: a listener question, some truly questionable fashion choices, and one more reason not to hoard your retirement benefits—or your holiday dishes. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Happy Independence Day, Stackers! While fireworks boom and flags wave, we're lighting a spark under your financial life. This episode isn’t about tea in harbors—it’s about burning down debt, revolting against lifestyle creep, and rallying your family for a better money future. Joining Joe and Doug in the basement for this full-on financial insurrection: Dorethia Kelly, TikTok titan and money coach, shares how she raised her financial flag as a single mom and became a force for smart money choices. Jesse Cramer of the Personal Finance for Long-Term Investors podcast ditches tired spending habits and charts a course for independence through intentional investing and budgeting. Steve Stewart, longtime SB editor and podcasting Yoda, reveals the pivotal Jeep moment that changed his financial course—and why he's racing OG to mortgage freedom. 🎙️ In this basement-based revolution, you'll hear: The financial “tea party” moments that woke our guests up to their money mess How to declare independence from credit cards, lifestyle creep, and sneaky “Buy Now, Pay Later” traps Tools, mindsets, and support systems that help you keep your financial revolution alive Why tax planning is the financial Boston Tea Party nobody's talking about The trivia showdown no revolutionary should miss: How many grains of silver made a dollar in 1792? (Spoiler: Jesse knows his colonial coinage.) And in the aftershow? We ask the deep questions our Founding Fathers never saw coming, like: why is gambling debt dischargeable in bankruptcy, but student loans aren't? FULL SHOW NOTES: https://stackingbenjamins.com/financial-independence-day-2025-1704 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What does it take to turn a bold idea into a billion-dollar brand? Julie Wainwright, founder of The RealReal, joins us to share how she did just that—after enduring some pretty public failures (hello, Pets.com). She talks about navigating the startup world, tackling ageism head-on, and why your past doesn’t define your future. Julie’s story is packed with wisdom on risk-taking, confidence, and what it really means to build something new when everyone else is telling you no. From the boardroom to the resale boutique, she takes us through the emotional rollercoaster of entrepreneurship—plus a few secrets on why luxury goods are more than just a pretty label. Also in the basement: We unpack Jason Zweig’s latest Wall Street Journal column on diversification and why it still matters (yes, even in this market). OG learns a Father’s Day lesson on the golf course (spoiler: not all swings are created equal). Doug manages to work in Margot Robbie. Again. Whether you’re plotting your own business empire or just wondering how someone not only recovers from flaming sock puppet-level failure, but who THRIVES afterward, this episode delivers honest insight with a side of style. FULL SHOW NOTES: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much can you really spend in retirement without running out of money—or worse, running out of fun? In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it’s time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might be possible—if you’ve got the right mix of investments, a solid plan, and a bit of courage. But we don’t stop there. Because with greater freedom comes greater risk (especially if you're leading with vibes instead of strategy). The guys tackle the sequence of returns risk that can derail early retirement years, and how to build a portfolio that helps you sleep at night—even during a market storm. Meanwhile, Doug drops in with an unexpected (and very British) culinary experience, Joe fields a listener question comparing financial plans to workout routines (is your Roth IRA doing enough reps?), and yes... we revisit our fan-favorite segment on how food waste is wrecking your budget. Why the 4% rule might be too conservative (or maybe just outdated). What diversified portfolios and asset class strategy have to do with a longer-lasting nest egg. How to prepare for market downturns before they happen—and what to do if you're already in one. Why retirement joy isn’t just about spreadsheets—it’s about the psychology of spending with confidence. Which type of green tea is the superior kind (depending on which side of the TikTok aisle you're on). How to reduce food waste and put that extra savings toward your bigger financial goals. If you’re approaching retirement—or even just dreaming about it—understanding how much you can safely spend without sabotaging your future is the question. This episode combines historical insight with today’s market realities to give you the real math and mindset you need to retire well…and maybe even with a smile. FULL SHOW NOTES: https://stackingbenjamins.com/problems-with-the-4-percent-rule-1702 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Can you really build wealth with a simple formula? Do you need a budget to succeed financially? Should you cut up all your credit cards, or is that just a dramatic TikTok trend? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy is joined by Paula Pant, Doc G (Jordan Grumet), and Jesse Cramer for a roundtable discussion that peels back the truth behind popular advice from so-called financial “gurus.” The conversation is rooted in a provocative blog post by Christine Luken that calls out four common money mantras—and the team dives into each one with classic basement wit, spirited debate, and hard-earned wisdom. Topics on the table: Do you really need a budget, or can you thrive without one? Are rigid financial formulas helpful or harmful? Is willpower the key to financial success—or just a scapegoat? Does cutting up credit cards actually solve your spending problems? Along the way, you'll hear banana jokes (yes, multiple), a heated trivia contest about obsolete technology (looking at you, LaserDisc), and some good-natured trash talk that might just surprise you with how insightful it gets. This episode is packed with nuance, laughs, and practical takeaways for Stackers who are tired of the one-size-fits-all guru approach. Whether you’re team budget or team spreadsheet freestyle, there’s something here for you—plus a solid reminder that when it comes to personal finance, the best advice is the advice that fits your life. FULL SHOW NOTES: https://stackingbenjamins.com/lies-damn-lies-and-statistics-1701 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What’s the best way to save for a house without wrecking your retirement plan? That’s just one of the big questions Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle in this packed episode (number 1700!) of Stacking Benjamins. Whether you're trying to figure out where to park your emergency fund, how to handle inherited IRAs, or how to financially plan as a single adult with big responsibilities (hello, aging parents!), this episode is full of relatable scenarios and actionable strategies. Stackers Torin, VJ, Lori, and Michelle ask everything from: How much is too much in your emergency fund? What happens to inherited IRAs when you're already juggling financial priorities? What should single people be doing right now to prepare for the future? How do you juggle helping aging parents while keeping your own goals on track? Plus, we mix in commentary from Kevin at Edward Jones and longtime listener Ron—offering insights from inside the financial services world and the Stacker community. The guys debate personal finance media narratives, give practical advice for budgeting large windfalls, and reflect on why saving feels easier in theory than in practice. Also covered in this episode: Why financial advice often skips over single individuals—and what to do about it Emergency fund strategies: where to park the money, how much to keep, and how to make peace with the fact it isn’t earning sky-high returns How to prioritize debt, student loans, savings, and investing without setting off a financial anxiety spiral The value of short-term tradeoffs when you’ve got long-term goals All delivered with the basement’s signature charm—where the coffee is lukewarm, the guidance is practical, and the jokes… well, let’s just say they’re dividend-eligible. This episode is a perfect listen for: New Stackers building their financial foundation DIYers trying to juggle competing money goals Anyone who’s inherited assets and doesn’t want to mess it up People who’ve realized adulting is basically managing 14 financial priorities at once and still remembering to bring snacks. FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-questions-mailbag-1700 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

The robots aren’t just coming—they’re already here. And if you’re not paying attention, they might not just take your job… they could take your personal data too. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug dive into the rise of artificial intelligence, exploring whether it’s a threat, a tool, or something in between. If you’ve been wondering how AI will impact your work, your privacy, and your future, this episode is a must-listen. They kick off with a surprising headline: Gen Z workers are sidestepping AI entirely—not by resisting it, but by choosing careers where machines can’t compete (like landscaping and trades), and using AI tools to grow their businesses faster. This sparks a full-on basement debate about how technology has historically impacted jobs, what the next evolution might look like, and whether AI will make our lives easier… or just busier. In today’s show: Why some jobs may disappear—but others are about to explode with opportunity The surprising role AI is playing in blue-collar and skilled trade growth Why being AI-curious (not AI-phobic) is your best financial move New tech tools that supercharge productivity—from transcription wallets to note-taking bots How AI is already transforming education and career paths What to do right now to stay ahead of the AI curve Then the guys shift gears to a more sinister topic: data privacy. CNET recently reported which free AI chatbots are scooping up the most of your personal info—and which are surprisingly respectful. The gang reveals which apps are best to trust, and which are like letting Zuck crash on your couch (bad idea). We’ll also hear from listener John, who wants to hire a financial advisor but isn’t sure where to start. Joe and OG break down how to find the right fit, why fees aren’t the most important factor, and the one question that tells you if someone’s worth hiring. Plus: Doug’s trivia on egomaniacal coin designers A TikTok minute about U2, dating apps, and dad jokes Back porch chatter about Pontiac Azteks, water treatment careers, and IMAX concert pilgrimages Takeaway: AI isn’t just a tech trend—it’s reshaping our economy, our careers, and even how we learn. Whether you’re a Gen Z worker, mid-career professional, or planning your retirement, now’s the time to lean in, explore what AI can (and can’t) do, and secure your future before the bots beat you to it. FULL SHOW NOTES: https://stackingbenjamins.com/ais-coming-for-your-job-how-to-outwit-the-robots-1699 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

So you’ve scaled the mountain, built the nest egg, and maybe even shouted “I’m done!” across a pristine beach... now what? In today’s Stacking Benjamins episode, Joe Saul-Sehy convenes a roundtable of heavy-hitters to tackle the most misunderstood phase of money management: decumulation—a.k.a. the art of spending what you’ve worked so hard to save. Whether you're staring down retirement or already deep into your golden years, you'll hear candid, practical insights from three financial thought leaders who specialize in making your money last. Joining Joe are Dana Anspach, retirement planning expert and founder of Sensible Money, Karsten Jeske (aka “Big ERN” from Early Retirement Now), and Frank Vasquez, aka Uncle Frank, host of Risk Parity Radio. Together, they bring decades of academic research, professional experience, and plain old common sense to questions like: What’s the real safe withdrawal rate—and why does it depend on more than just spreadsheets? Should you chase simplicity or embrace complexity in managing retirement funds? What role do annuities and guaranteed income play in reducing late-life anxiety? How do you plan for cognitive decline without spiraling into existential dread? What’s the difference between spending confidently... and spending carelessly? You’ll also hear why lumpy expenses, long-term care surprises, and behavioral quirks can trip up even the best-laid plans—and how to bulletproof your strategy now. And yes, we get nerdy. Risk parity, sequence of return risk, and portfolio glidepaths all make guest appearances—but always with your favorite Stacking Benjamins charm and plain-English style. Because retirement doesn’t need to be scary... but it does need to be intentional. Why your investment approach needs to evolve once paychecks stop The strengths and blind spots of the “4% rule” How emotions (not just inflation) affect safe withdrawal strategies When it makes sense to annuitize, and when it absolutely doesn’t How to adjust for cognitive decline in your financial plan (and still maintain autonomy) The “spend conservatively early” myth—debunked Tips for managing healthcare and other unpredictable late-life costs Whether you’re a retiree, a pre-retiree, or a spreadsheet-loving financial independence buff, this deep-dive episode will give you the confidence to manage the second half of your financial life like a pro. This isn't just about stretching your dollars—it's about building a life worth spending them on. So grab your planner, pour a cup of whatever says “retirement-ready” to you, and let’s get smarter (and maybe just a bit weirder) about your golden years. FULL SHOW NOTES: https://stackingbenjamins.com/create-your-retirement-spending-plan-1698 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if the most important part of your retirement plan had nothing to do with your 401(k), IRA, or stock portfolio? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by filmmakers Pete Davis and Rebecca Davis, creators of the thought-provoking documentary Join or Die. They explore how community connection, not cash, may be the ultimate retirement strategy. Drawing inspiration from the late political scientist Robert Putnam (Bowling Alone), the Davises reveal why joining groups—book clubs, church choirs, rec leagues, neighborhood associations—might be more essential to your long-term well-being than your asset allocation. Together with Joe and OG, they unpack the data behind social decline, the healing power of showing up, and what the film Join or Die teaches us about leading a richer life beyond the numbers. Of course, Mom’s Neighbor Doug pops in with trivia that proves he belongs (at least to this show). Whether you’re on the path to retirement or simply looking for deeper purpose, this episode will make you think differently about how you stack your most valuable resource: time. Why joining a club may be just as critical to retirement as saving for it What Join or Die reveals about America’s shrinking social networks How loneliness affects physical and financial health—and how to fight it Why your “portfolio of community” might be the highest-yield investment you ever make Ways to build meaningful connections now—even if you don’t feel like a “joiner” Pete and Rebecca Davis share behind-the-scenes stories from making Join or Die Joe and OG reflect on what gives life meaning after the 9-to-5 ends Surprising data on the link between social capital and financial confidence Doug delivers a trivia challenge about famous clubs (and less-famous neighbors) 📚 Resources & Mentions: 🎥 Join or Die documentary by Pete and Rebecca Davis 📘 Bowling Alone by Robert Putnam 🎙️ Pete Davis’s book: Dedicated: The Case for Commitment in an Age of Infinite Browsing 👟 Your Challenge This Week: Sign up. Show up. Speak up. Whether it's your local book club, PTA, pickleball team, or town council meeting—belonging starts with one yes. 💬 “Retirement planning isn’t just about money—it’s about meaning.” Tune in and learn how to build a life you won’t want to retire from. FULL SHOW NOTES: https:;//stackingbenjamins.com/join-or-die-documentary-pete-rebecca-davis-1697 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You can’t plan a great retirement if you haven’t first planned what you’re retiring to. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug open up Retirement Week in the basement with a Monday that’s equal parts insight, weekend recap, and questionable vehicle decisions. 🚪 Start with the most overlooked part of retirement: your lifestyle vision. What are you actually going to do all day—and will it make you happy? 📊 Then they dive into financial strategy, from coordinating pre-tax, Roth, and taxable funds to dodging sneaky IRMAA fees that show up like glitter—impossible to get rid of and oddly expensive. 🏎️ Thinking about a new car? Joe and Doug wrestle with the age-old question: maintain or upgrade, and how your answer could affect your wallet (and maybe your driveway credibility). 💼 Curious about investment leverage? Meet Basic Capital—a platform that might sound like a good idea… until it doesn’t. Joe and OG explain when leverage can help—and when it’s just risk in a tuxedo. 🎧 Plus: Saluting the troops What not to do when your retirement plan involves TikTok A sneak peek at the Nerdy Round Table And entertainment recs to round out your week like a pro Start your week smarter and get a little closer to a retirement you actually want. FULL SHOW NOTES: https://stackingbenjamins.com/creating-a-better-retirement-1696 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Markets crashing? Interest rates spiking? Inflation roaring? Welcome to history. This week, we dig into 130 years of stock market meltdowns—from the panic of World War I to the Great Depression, 1970s stagflation, the dot-com collapse, and the 2008 financial crisis—to uncover timeless lessons that can fortify your financial future. Joe Saul-Sehy is joined by Miranda Marquit, Jesse Cramer, and OG to examine how investors have historically responded to chaos... and how you should, too. You'll learn why diversification matters, why panic rarely pays, and why staying the course (even when it’s scary) can be the smartest move of all. Of course, this wouldn't be the Stacking Benjamins Show without a trivia detour that involves mailing children through the U.S. Postal Service (yes, that happened). Buckle up for laughter, insight, and financial takeaways that are as practical as they are entertaining. What WWI, the Great Depression, and 1970s inflation can teach us about investing Why “The Lost Decade” wasn’t a loss for long-term thinkers How to build a resilient portfolio that weathers the storm Our infamous trivia game: How much could a kid weigh and still be legally mailed in the 1920s? A few money-saving hacks, podcast updates, and your weekend preview from the basement Whether you’re a seasoned investor or just building your financial foundation, this episode will leave you smarter, more confident, and—let’s be honest—way more amused than the average market history lecture. FULL SHOW NOTES: https://stackingbenjamins.com/lessons-from-stock-market-history-1695 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What happens when you mix financial strategy with a healthy dose of cultural commentary? You get Rich Girl Nation. This week on The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Katie Gatti Tassin, the powerhouse behind Money with Katie and author of the new book Rich Girl Nation. Together, they unravel the sneaky ways consumerism shows up in our lives—from pricey trends to status-signaling spending—and how it messes with our wallets. Katie dives into the “hot girl hamster wheel” of overspending, the wage gap, and why negotiating your salary (without flinching) is one of the best financial moves you can make. She also offers sharp, tactical advice on job-hopping for higher pay and automating your money to avoid lifestyle creep. Meanwhile, the crew throws in real-life stories, from Cybertruck depreciation to celebrating financial independence in more ways than one. And of course, Doug drops in with a trivia twist that keeps things weird—because it wouldn’t be the basement without a little curveball. 🧠 What You’ll Learn: How to identify and eliminate unnecessary spending that doesn’t align with your values Strategies for negotiating salary like a pro (and when silence says more than words) How to avoid the early adopter tax on flashy new products The role of automation in building sustainable wealth Why understanding depreciation is a game-changer for big purchases Whether you're climbing the corporate ladder or just trying to spend smarter, this episode offers a refreshing mix of real talk and practical advice—served up with classic basement wit and a side of financial independence. Let’s make money moves that actually feel good. FULL SHOW NOTES: https://stackingbenjamins.com/rethinking-earning-and-spending-with-kate-gatti-tassin-1694 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is your wallet feeling lighter... but your closet’s full of regret? Joe, OG, and Mom’s neighbor Doug are throwing open the basement door to tackle one of the trickiest parts of personal finance: consumerism. Whether you're a recovering impulse buyer or knee-deep in buy-now-pay-later regrets, this episode’s got your back—and maybe your budget. 💸 Hear real stories about overspending and why value-based spending beats chasing trends. 🛍️ Unpack the rise of Klarna and other buy-now-pay-later services—and the hidden costs that come with them. 🌍 Explore how global economic shifts (yep, we’re going there) could impact your investments. 🎤 And just when things get too real, the team lightens it up with a no-holds-barred burger chain draft. In-N-Out? Five Guys? Wendy’s? Who makes the Stacker cut? Plus: a shoutout to the troops, a TikTok Minute that involves Doug and a questionable egg sandwich, and trivia that’ll make you rethink your next holiday shopping spree. You don’t need to live like a monk—just stop buying stuff you don’t even like. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-break-free-from-consumerism-1693 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Can building wealth be as entertaining as a round of trivia in the basement? We think so—and today’s episode proves it. Joe Saul-Sehy is joined by Doc G, Paula Pant, and Jesse Cramer to play a fast-paced financial game show based on 11 expert-approved ways to grow your wealth. From boosting your income and dialing in your budget to the eternal tug-of-war between paying down debt and investing more, this episode delivers wisdom with a side of basement-brand chaos. But we don’t stop at just the basics. Our roundtable dives into: How homeownership plays into your wealth picture (even if it’s not as sexy as index funds), Why insurance coverage might be your best wealth-preserving move, The truth about improving your credit score without obsessing over every point. Plus, a trivia celebration of 50 Cent’s Vitamin Water payday turns into a lesson in surprise wins—and surprise losses. Whether you're just beginning your wealth-building journey or refining your strategy, this episode brings practical insights, hearty laughs, and a gentle nudge to rethink what really grows your net worth. How to increase your income (without selling essential organs) Budgeting strategies that actually stick Why investing early matters—and when paying off debt takes priority The real ROI of proper insurance coverage A homebuying debate that might ruffle some financial feathers Birthday trivia for 50 Cent and the Vitamin Water deal that made him a legend End-of-episode takeaways you’ll want to write down (or tattoo, if that’s your thing) Stackers, whether you're navigating rainy days or planning for a brighter financial future, today’s conversation will help you stack smarter, live better, and maybe even walk away with a new strategy—or at least a smile. FULL SHOW NOTES: https://stackingbenjamins.com/our-favorite-ways-to-grow-wealth-1692 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

After Monday’s primer on why your portfolio needs some international flavor, we’re following up with a deeper dive—this time with someone who lives and breathes global markets. Joe Saul-Sehy and OG welcome Joy Yang, Head of Index Product Management at MarketVector Indexes, to talk through how to actually invest beyond U.S. borders. Joy explains how ETFs can help investors capture international growth while minimizing risk—and why country-specific and sector-specific ETFs might just be your new best friend. You'll also hear insights on investing in private markets, the rise of digital assets, and whether private equity in your 401k is a brilliant idea… or a cautionary tale. But don’t worry, the basement stays weird. Doug brings the trivia heat with a Martha Stewart–Eliot Spitzer stumper, and the episode wraps with some creative audience feedback (including one Stackers’ AI-powered school project that caught our attention). Topics Covered: How to diversify globally without overcomplicating your portfolio The power of ETFs for targeting specific markets and sectors What you really need to know before considering private equity in retirement accounts Balancing simplicity with opportunity in a world of shiny investment options The limits of “going big or going home” when it comes to risk and return Stackers, if you’re looking for smart ways to expand your portfolio’s reach—or just curious what index creators think about Bitcoin—this episode delivers insights, laughs, and a grounded reminder: simple can still be smart. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-invest-globally-with-joy-yang-1691 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How global is your portfolio, really? This week in the basement, Joe Saul-Sehy, OG, and the gang zoom out from the U.S. markets and take us on a whirlwind trip around the investing world. Spoiler alert: the case for international investing is stronger than you think—and it’s not just about chasing higher returns. It’s about risk reduction, smart diversification, and maybe even admitting that the U.S. isn’t always the world’s MVP. You'll hear how developed and emerging markets fit into a well-balanced portfolio, how correlation works in your favor (yes, this time that’s a good thing), and what history tells us about going global. Joe and OG share practical advice for how to get started, when to rebalance, and how much international exposure might make sense for the average Stacker. Then in the second half, we pivot from markets to money buffers: listener Jeff from Cleveland wonders how to set insurance deductibles based on the state of his emergency fund. We break down how to think about the real return on your rainy-day stash—because spoiler: it’s not about the interest rate, it's about your resilience. To wrap things up, we share timeless wisdom from Stackers across the country on what they’d tell new graduates about money, life, and how not to blow that first paycheck on a jet ski. Why international investing may improve both your returns and your risk profile How much of your portfolio to allocate internationally—and what history suggests What "correlation" really means and why it’s your friend (at least in investing) Risks and common misconceptions of investing overseas How to choose between developed vs. emerging markets Portfolio tools to visualize your asset mix and expected outcomes Why your emergency fund’s best ROI might be peace of mind How to align insurance deductibles with your liquidity cushion What our community of Stackers wishes they had known after graduation FULL SHOW NOTES: https://stackingbenjamins.com/making-the-case-for-international-investing-1690 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, we’re getting deep (like, basement-deep) into what it means to flourish. Join Joe, OG, Paula Pant, and special guest Ryan Doolittle as they unpack a brand-new study on happiness. Spoiler: it’s not just about stacking cash. From the influence of childhood experiences to the surprising power of community, autonomy, and faith, this episode asks whether true wealth is more emotional than numerical. Plus, Ryan shares his adventures from his new series Try and Ryan—where he road-tests hobbies that might just add meaning to your retirement (and your Tuesdays). What we’re exploring in the basement: 🌱 What the latest research says about flourishing—and why it’s not just for the rich 👶 How childhood trauma or support plays into long-term happiness ⛪ Religious attendance: a surprising common thread in many “happy” lives 🎯 Autonomy, mastery, and purpose at work—and why they might matter more than promotions 🌍 Why Finland keeps winning the “World’s Happiest Country” race (and what Americans might learn from it) 💰 How financial flexibility might be more valuable than financial freedom 🧓 Gender and retirement happiness: why the experience might not be equal across the board 🛠️ Ryan’s “Try and Ryan” series and how picking up hobbies can boost life satisfaction 🏎️ Also: Trivia mayhem involving the Indy 500, Paula’s cat gets a shoutout, and OG still won’t drive stick 🎙️ Want to be wealthy and well? Tune in for a conversation that’s as heartfelt as it is hilarious—because in the basement, we believe money’s just the fuel. Flourishing is the journey. Show notes: https://www.stackingbenjamins.com/money-happiness-and-flourishing-1689/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Turns out, saving $3,000 a year might be easier (and tastier) than you think. This week, we’re dishing up big savings with Bryan Suddith, who turned his family’s runaway grocery bill into a budget-friendly game—complete with freezer hacks, local meat tips, and food waste strategies that actually work. He joins Joe, OG, and guest co-host Len Penzo (yes, that Len Penzo of LenPenzo.com fame) to share how mindful meal planning can make your wallet and your taste buds happy. We’re also talking about a Wall Street Journal piece that reveals why high schoolers are ditching traditional degrees for skilled trades... and landing $70K jobs right out of the gate. Plus, Doug helps us navigate one of life’s most awkward questions: What do you call your friend’s mom? (Hint: it’s not “Linda.”) What’s stacked inside this episode: 🧾 How Bryan gamified his grocery budget and saved thousands—with zero meal-prep burnout 🥩 Freezer hacks, locally sourced meats, and the joys of slow-thawed financial wins 🥦 Food mindfulness: the surprising connection between awareness and grocery savings 🎯 Why budgeting doesn't have to feel like punishment (especially when TikTok is involved) 🎙️ Bryan’s bonus storytelling and public speaking tips for anyone who has to talk to humans 🔧 Trade school is trending: why $70K jobs are showing up before diplomas 🧰 Should your teen consider HVAC over Harvard? We unpack the growing case for skilled trades 🤷‍♂️ Conan O'Brien, Doug, and the Great Parental Naming Debate of 2025 💡 If you’ve ever overpaid at the grocery store or underestimated a plumber’s paycheck... this one’s for you. Bring your shopping list and your sense of humor—we’ll meet you in the basement. Full Show Notes: https://www.stackingbenjamins.com/avoid-food-waste-and-save-benjamins-bryan-suddith-1688/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think you're being lied to at work? You probably are. From boardrooms to bank accounts, this episode pulls no punches. We’re stacking double the wisdom on this special Memorial Day episode, as Joe Saul-Sehy interviews two powerhouse guests: Bonnie Hammer, former vice chair of NBCUniversal and bestselling author, and Dr. Erika Rasure from Beyond Finance. Whether it’s breaking glass ceilings or breaking out of debt, this episode is your roadmap to reclaiming control. Inside the episode: 💼 Bonnie Hammer calls B.S. on the “15 lies women are told at work” — and explains how to rewrite the rules 🎬 Behind-the-scenes of Suits and why even hit shows face wild career landmines 🧠 How your attitude and teamwork can make or break your climb to the top 💬 Dr. Erika Rasure on why 50% of Americans don’t trust themselves with money — and how to start 💸 The real emotional blockers behind budgeting, saving, and staying out of the online cart trap 🧍‍♀️ Gender and generational gaps: why confidence with money isn’t equally distributed (but should be) 🛠️ Financial “practice weeks” and mindset shifts to get unstuck from shame and paralysis ✅ A simple path to get control over your debt without feeling like you’ve failed Also: Doug delivers his own Memorial Day tribute and trivia, because of course he does. 🎙️ Ready to outsmart bad advice and start building on your own terms? This one’s for you — whether you’re climbing the corporate ladder or clawing your way out of credit card debt (or both). FULL SHOW NOTES: https://stackingbenjamins.com/lies-work-and-money-with-bonnie-hammer-and-dr-erika-rasure-1687 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Memorial Day weekend is here, which means it’s officially time to break out the grill, the beach bag… and maybe that travel budget spreadsheet. But don’t worry—this isn’t a guide from travel influencers who hike barefoot with artisanal backpacks. Nope. This episode is brought to you by your favorite money geeks in Joe’s mom’s basement. Joe Saul-Sehy, OG, Jesse Cramer, Crystal Hammond, and Doug gather 'round the card table to share their best budget-friendly travel strategies, hilarious vacation stories, and maybe one or two travel fails. From choosing the right travel companion to navigating airports like a boss, this crew drops loads of practical wisdom for making your summer adventures awesome and affordable. You’ll learn why credit card points can be your best friend, how to pick lodging that won’t make you cry (or bankrupt you), and why packing a toothbrush is a good idea… even if Doug’s trivia makes you question the timing. This isn’t expert advice. These are the musings of people who spend more time optimizing their wallets than their luggage. And that’s exactly why you’ll leave feeling better prepared to tackle your own summer travel—without the jet-setter guilt trip. Kicking off summer with a Stacking Benjamins travel roundtable Real-life travel hacks from people who care more about budgeting than boarding groups Credit card point strategies that actually work Hot takes on hotels, Airbnbs, and airport snacks Why picking the right travel buddy can make or break your trip The one item Doug thinks was more important than nylon (it’s… something) Whether you’re headed to the lake, the mountains, or just your backyard with a cold drink, join the crew for a hilarious and practical celebration of summer travel. Full Show Notes: https://www.stackingbenjamins.com/our-favorite-summer-travel-tips-1686/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do cupcakes, frosting, and financial independence have in common? This week in the basement, Stacking Benjamins welcomes legendary personal finance thinker JL Collins, author of The Simple Path to Wealth, to connect the dots between simple investing and sweet, stress-free success. In a lively conversation with Joe Saul-Sehy, OG, and Mom’s neighbor Doug (who may or may not be launching a frosting-themed protest movement), JL shares timeless wisdom on avoiding complexity, embracing low-cost index investing, and why FU money is more than just a clever phrase—it’s freedom in a bank account. You’ll hear JL’s take on portfolio allocation, debt’s sneaky impact on your future, and how to survive volatile markets without sacrificing your peace of mind. If you’ve ever felt stuck in a soul-crushing job? JL’s got some perspective you’ll love. Then, in the second half of the episode, Joe and OG shift gears to answer a listener question from Mike. He’s wondering about the efficient frontier—yes, we’re getting fancy now—and wants to know how to move beyond the Simple Path. Joe walks through the different asset classes he thinks about when crafting a diversified portfolio, while OG shares how to think through asset allocation as your wealth and confidence grow. Whether you’re curious about real estate, international investing, or just how much to hold in bonds, you’ll walk away with a clearer picture of what your portfolio could look like after “graduating” from JL’s foundational advice. Why keeping it simple beats chasing trends What “FU money” really means—and how to get it The truth about withdrawal rates and why they matter When debt becomes a dream killer Tips for navigating market downturns without panic How to find freedom without spending a fortune JL’s surprisingly profound parable about a monk, a minister, and money Doug’s hot take on the great frosting vs. cake debate A deep dive into the efficient frontier and how to set up your asset allocation beyond VTSAX Joe Saul-Sehy and OG’s thoughts on portfolio construction for seasoned investors JL’s insights have inspired millions on the path to financial independence—and now it’s your turn. Tune in, take notes (or don’t, we’ll recap it in the 201), and remember: sometimes the sweetest success starts with doing less. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-simple-path-to-contentment-with-jl-collins-1685/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is it summer already, or is that just our theme park budget melting in the sun? Either way, we’re kicking off the season with our annual guide to roller coasters, churros, and how not to hurl after one too many loops. Theme Park Insider’s Robert Niles returns to share the biggest news in amusement park land—from a new Disney park in Abu Dhabi (what?!) to Universal Orlando’s game-changing Epic Universe. But what’s a summer kickoff without a good ol’ whiplash reminder that your brain can’t be trusted when it comes to investing? Joe Saul-Sehy and OG dive into Jason Zweig’s latest insights about how our market “memory banks” mess with decision-making, and why 2008 probably wasn’t as scarring as your gut tells you. And yes, Doug's trivia ties it all together—with corn dogs, naturally. How to actually save money at theme parks without having to sleep in a costume closet. The surprising reason a $1,400 day at Disney might be your own fault. Which new coasters (and old favorites) are worth the detour this year. Why your gut—and your "market memory"—could be sabotaging your investments. The last time the stock market went down multiple years in a row (hint: not 2008). What Robert’s favorite underrated U.S. parks are (spoiler: Dollywood shows up, again). How to strategically splurge or save at the parks—merch fans, avert your eyes. 🎢 This one has thrills, chills, and the occasional spreadsheet. Just how we like it. FULL SHOW NOTES: https://www.stackingbenjamins.com/welcome-summmer-2025-with-robert-niles-1684/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What really moves the needle on your happiness—making more money or saving more of what you’ve got? This week, Joe Saul-Sehy and OG are joined by Paula Pant, Jesse Cramer, and the guy who still owes money on his Beanie Baby collection—Doug—for a roundtable filled with bold financial takes and even bolder choices. It’s a rapid-fire round of “either-or” dilemmas, and while nobody gets voted off the island, a few sacred cows are gently tipped over. Should you max out your retirement account or finally slay your student loans? Ditch credit cards for cash? Bet your future on crypto or keep it stuffed in a fireproof mattress? Our panel debates these decisions and shares real-life stories of what’s worked—and what’s blown up like a microwaved burrito. Of course, it wouldn’t be The Stacking Benjamins Show without a detour or two: we dig into financial hoarding (how many dusty envelopes is too many?), reveal why your credit score might be your best frenemy, and serve up some vintage airplane trivia, just to keep things classy. So whether you're team "Earn More" or team "Cut Back," this episode delivers the kind of guidance that helps you feel a little more confident making your next money move—even if it’s just saying no to another financial “shortcut.” Topics covered include: Why more income might not be the golden ticket The case for ditching your credit card (and why that makes Doug twitchy) Saving vs. investing vs. spending like you’re already retired What financial hoarding reveals about your mindset Index funds vs. individual stocks: which one should get your long-term commitment? The never-ending crypto debate (now with 12% more existential dread!) How obsessing over your credit score may or may not ruin your weekend If you’re figuring out how to balance today’s latte with tomorrow’s freedom—or you just want to feel smarter about money than your cousin Gary who “invests in vibes”—this one’s for you. And remember, no matter how much you earn or save, the real ROI is tuning in with the Stackers each week. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-happiness-debate-1683/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like money is a never-ending game of not enough? Today, we're rewiring that thinking. Our special guest, Leisa Peterson—author of The Mindful Millionaire and now The Money Catalyst—joins us to talk about abundance, scarcity, and how to stop living life like you're budgeting for armageddon. (Hint: It's okay to order the nice wine now.) Joe Saul-Sehy and OG also shine a light on the resurgence of alternative investments. Is it innovation... or just Wall Street’s way of sneaking in high fees through the back door? Plus, we roll into Doug’s trivia, a TikTok Minute that flips the script on a certain “draft pick,” and, of course, a few stories that prove—yet again—that golf is no game for the frugal. “Am I YOLO-ing or just broke?” Why framing matters more than frugality From scarcity to satisfaction: How one moment in Paris changed Leisa’s relationship with money You call that a tip? The surprisingly deep conversation behind street musicians, champagne, and generosity Alternative investments are back (again?) Why your advisor might pitch you on ditching the market... and why you should think twice Personal growth through fiction: Leisa's surprising journey from nonfiction burnout to a book that might just fix your wallet and your heart When the camel arrives with a skeleton on its back: Doug’s trivia gets weird (and somehow financial) TikTok Minute: What happens when a 50-year-old thinks he just got drafted into the NFL OG’s rule of thumb: Volatility isn’t the villain—it’s the entrance fee 🪄 PS: Boston-area Stackers! Joe’s coming your way May 20th. Get all the meetup deets at stackingbenjamins.com/meetup 🎧 Listen now and start living (and spending) like abundance is already yours. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do most millionaires have in common? No, it’s not a yacht named “Compound Interest.” It’s mindset. In this episode, Joe Saul-Sehy and OG kick off Mindset Week by welcoming Sam Dogen, the Financial Samurai himself, to help you start your journey toward a million-dollar net worth—one intentional step at a time. Sam shares why building wealth is less about luck and more about grit, clear goals, and a killer savings rate. He explains why $250,000 is the magic milestone where compounding takes over, why your “why” is more important than your budget, and how a simple house-to-car ratio can reveal whether you’re cruising toward financial freedom or stuck in the valet lane. You'll learn: Why your first $250,000 is the hardest (and most critical) How to find your “why” and let it drive your money decisions Why some people crush millionaire goals while others stall out The pros and cons of prioritizing student loan payoff How real estate, entrepreneurship, and mindset play a role in long-term success Plus, Doug delivers trivia about the world’s most millionaire-dense country (hint: it’s not the U.S.), and Joe announces a live event with Boldin’s Steve Chen to help you master retirement planning tools. All that and a wink toward OG’s dream car obsession (which definitely didn’t come from the after-show... wink wink). 💥 Want to level up your financial thinking? This episode is your launching pad. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-start-on-your-financial-journey-with-financial-samauri-sam-dogen-1681 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If your grocery bill has you doing double-takes at the checkout line, you’re not alone—and this episode of The Stacking Benjamins Show is packed with practical ways to take control of your food spending. Joe Saul-Sehy is joined by Janice Torres of the Yo Quiero Dinero podcast, regular contributor OG, and the always-frugal Len Penzo to serve up real-world grocery hacks that help you stretch your dollars without skimping on flavor or quality. You’ll learn: How meal planning can shrink your bill (and your food waste) When buying in bulk pays off—and when it’s just a trap Why pre-packaged foods might be eating up your budget Which apps help you unlock store discounts and cash back And whether starting a garden is actually worth it for your bottom line We also dig into freezer strategies, the art of cutting back on meat without feeling deprived, and a few guilty pleasure restaurants that somehow always find their way back into our budgets. It’s a money-saving roundtable that’s equal parts helpful and hilarious. Come for the grocery hacks, stay for the side dishes of personality. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Your burning questions fuel this episode! Joe Saul-Sehy, OG, and special guest Christine Benz of Morningstar unpack some of the biggest questions facing investors today—especially those just starting out. We kick things off by diving deep into target date funds. They promise simplicity—but do they deliver long-term results? We explore when they work, when they don’t, and what you should consider if they’re part of your portfolio. Then Christine shares a graduation-season masterclass in financial advice: How to begin investing, even when you feel behind Why lifestyle creep is the silent killer of wealth The importance of building habits now that will serve you for decades Resources and reading recs that can actually move the needle for new grads (and not-so-new grads) We also answer listener questions on: Whether refinancing your mortgage is still a smart move How global shifts in labor and supply chains may impact your finances And why it’s time to give your favorite retirement calculator a second look And somewhere in all this… someone may or may not reveal a dream dinner scenario that involves a pair of country music legends. But, you know, that part probably didn’t happen. Probably. Whether you're just graduating, recalibrating, or rethinking your strategy entirely, this episode is your invitation to stack smarter—and have a little fun while you do it. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe Saul-Sehy sits down with bestselling author Jen Sincero, the powerhouse behind You Are a Badass and You Are a Badass at Making Money. If you've ever felt stuck in financial quicksand or caught in a loop of scarcity thinking, Jen brings the fire (and the funny) to help shift your mindset and start building wealth from the inside out. You’ll hear: How Jen went from living in a garage to becoming a seven-figure entrepreneur The mindset shifts that changed her relationship with money—and could change yours Why self-talk and affirmations aren't fluff—they're your financial launchpad Simple ways to start reprogramming how you think, spend, and save The importance of consistent investing—even when you’re not feeling confident We also touch on: Why your HSA might be a secret investing weapon What to know as tax deadlines approach (and how not to panic) A listener’s creative approach to investing—and how OG and Joe weigh in Plus: marathon filming, TV mishaps, and trivia surprises from Mom’s neighbor Doug If you're ready to stop playing small with your money and start stacking like a badass, this episode will give you the mindset—and motivation—to get going. FULL SHOW NOTES: https://stackingbenjamins.com/you-are-a-badass-at-making-money-greatest-hits-week-1678 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Buying vs. renting: it’s one of the most emotionally charged—and financially misunderstood—topics in personal finance. This week on The Stacking Benjamins Show, Joe Saul-Sehy, OG, and guests Jesse Cramer and Chris Luger enter the ring to challenge the conventional wisdom behind homeownership. It’s not just a polite chat. It’s a full-on basement debate where no side goes unchallenged. You’ll hear: The surprising math behind renting—and why it’s not “throwing money away” What most homeowners don’t budget for (and pay dearly for later) Why buying a house might be one of the best—or worst—decisions you ever make How lifestyle, mobility, and flexibility factor into long-term wealth The emotional traps, practical benefits, and tough tradeoffs on both sides Plus, Mom’s neighbor Doug gets into full trivia-host mode with a Star Wars challenge, and we sprinkle in some good-natured jabs, marketing wisdom, and a reminder that there’s no one-size-fits-all answer. If you’ve ever bought a home, sold one, rented, or even thought about doing any of the above—this episode will make you think twice. FULL SHOW NOTES: https://stackingbenjamins.com/renting-vs-buying-forever-1677 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Retirement might be the goal, but the journey? Full of curveballs. On today’s episode, Joe Saul-Sehy is joined by special guest co-host Len Penzo of LenPenzo.com, along with OG and Neighbor Doug, for a no-holds-barred look at what really derails retirement plans—and how to build a strategy that can handle the chaos. From unexpected job loss to rising long-term care costs, adult kids moving back home, and even changing relationship dynamics, this episode dives into the often-overlooked risks that can chip away at your retirement dreams. Inside the episode: What to consider when evaluating long-term care insurance How job instability late in your career can throw off your timeline The growing trend of adult children impacting their parents’ retirement Grandparents becoming full-time caregivers—and the financial toll that brings Relationship shifts and widowhood in retirement Downsizing, austerity planning, and staying financially flexible Plus, our TikTok Minute features Gary V on why taking a step backward might be the smartest move forward. And as always, Doug brings the trivia heat—this time, with a nostalgic nod to a certain potato-headed toy. With Len Penzo in the basement, the insights (and squirrel references) are extra sharp. Prepare to laugh, learn, and rethink what “retirement ready” really means. FULL SHOW NOTES: https://stackingbenjamins.com/four-things-that-can-derail-your-retirement-plan-1676 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

When it comes to living your best financial life, good health isn't a nice-to-have—it’s a must-have. In today’s episode, we welcome Angelo Poli from MetPro, who shows us why smart fitness and nutrition choices are just as important as smart money moves. Drawing on insightful listener questions, Angelo shares: How consistent habits—not extreme diets—build the foundation for long-term health The real scoop on intermittent fasting, the carnivore diet, and other trending fads Practical ways to lower blood pressure, boost energy, and keep momentum even when life gets busy Why managing your wellness is one of the most powerful ways to protect your future earning potential and enhance your quality of life Because stacking Benjamins isn't just about saving—it's about having the health and energy to enjoy them. Later in the show, Joe and OG tackle smart financial strategies for uncertain markets: How to choose the right financial advisor when fear is everywhere What really matters in your long-term financial plan Why stability and experience will always outperform hype And finally, we dig into Home Equity Lines of Credit (HELOCs)—what they are, when to use one wisely, and how to avoid the common traps. This episode is all about stacking smarter—your wealth, your health, and your life. FULL SHOW NOTES: https://stackingbenjamins.com/improve-your-health-and-your-finances-in-2025 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do zipper injuries, holiday party mishaps, and servant leadership have in common? They’re all part of today’s wide-ranging look at careers—what to do, what not to do, and how to make your next move smarter (and safer). Joe Saul-Sehy, OG, and Neighbor Doug are joined by contributors Sandy Smith, Jesse Cramer, and a few classic career stories from the SB vault. Together, they explore: The surprising power of likability in the workplace How consistency and personal branding can open big doors Why some leadership styles flop and others inspire The real-life career missteps that made us all a little wiser A closer look at the Elevate Conference, which champions financial literacy for Black women And of course, it wouldn’t be a basement episode without a trivia challenge. This time, Doug delivers a stat that’ll make every listener squirm—let’s just say it involves zippers and emergency rooms. Whether you're climbing the corporate ladder, considering a leap, or just trying to avoid HR’s bad side, this episode packs in real advice and memorable stories from people who’ve been there, done that, and got the awkward email to prove it. Smart moves, cautionary tales, and Doug’s very specific warning about pants—this one's got it all. FULL SHOW NOTES: https://www.stackingbenjamins.com/improve-your-career-trajectory-1674/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you stand out in a competitive workplace—without shouting or burning out? In this episode, Joe and OG sit down with Lorraine K. Lee, a sought-after keynote speaker and former LinkedIn and Prezi leader, to dig into the real strategies behind building a career brand that lasts. Lorraine shares what she’s learned from coaching thousands of professionals, plus her own journey from behind-the-scenes to center stage. She introduces her EPIC framework—a smart approach that helps you craft a standout career identity built on: Experiences Personality Identity Community You’ll also learn: How to advocate for yourself without being “that person” The power of thoughtful feedback (and how to actually get it) Tactical tips to master Zoom meetings, digital presence, and virtual impressions Why embracing your differences can give you a serious edge in your career And after the career conversation? We shift into Stacker-style financial clarity—covering key money decisions people face during uncertain times: Should you wait to buy a home, or pull the trigger now? What do tariffs mean for your next car purchase? How should you approach investing when the market’s wobbling? From personal branding to practical budgeting, this episode gives you the tools to think clearly, act strategically, and build a future you’re proud of—no matter the economy. This one’s packed with high-leverage insights. Bring a notepad. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today’s episode blends career strategy with financial know-how, because who says you can’t build your personal brand and your balance sheet at the same time? Joe Saul-Sehy and OG explore what it really means to shape your professional reputation—from the way you show up in meetings to how you set (and measure) your career goals. Whether you're climbing the ladder, shifting industries, or mentoring others, this episode delivers practical ways to take control of how you're seen and what you stand for at work. Inside this conversation: The “RAVE” model for boosting your brand Why being a cheerleader for your colleagues makes you a standout How appearances and visibility (yes, even your Zoom background) impact your path Real-world tips for growing your influence without bragging—or burning out We also get into the intersection of tech and money: Is AI ready to replace financial advisors? (Short answer: not quite.) What metrics every financially literate person should understand And why your credit card points strategy might need a second look Plus, Doug breaks out a trivia challenge involving coin collecting, and we unravel the very weird truth behind the 1 cent piece. Whether you’re building a career, managing your money, or trying to do both with a little more polish—this episode’s packed with insights that stick. FULL SHOW NOTES: https://www.stackingbenjamins.com/your-career-brand-sb1672 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Some people master reinvention. They move from one stage of life to the next with confidence, purpose, and an eye on long-term success. What if your financial plan could do the same? In today’s roundtable, Joe is joined by Alyssa Maes, Roger Whitney (The Retirement Answer Man), and OG to talk about what it takes to build wealth that lasts—not just through one season of life, but through all of them. 🎯 Inside the episode: What starting strong in your 20s and 30s really looks like How to fight lifestyle creep and sharpen your personal brand mid-career Why simplifying cash flow in retirement can be a game-changer The power of habits, automation, and adaptability across all stages And what consistent, thoughtful choices can do for your long-term success The thread running through it all? Knowing who you are, where you're going—and letting your financial decisions reflect that. We also sneak in a bit of trivia involving the most expensive comic book ever sold and a certain pop icon with a track record of breaking records (you can probably guess who). This episode is about more than music or money—it’s about making every era of your life count. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What Taylor Swift teaches us about strategy, long-term thinking, and building an empire. Taylor Swift isn’t just a pop icon—she’s a master strategist. And in this episode, we unpack exactly how she built a cultural and financial empire with smart moves that offer powerful lessons for any Stacker. Joe Saul-Sehy sits down with Kevin Evers of Harvard Business Review Press to explore: How Taylor’s early partnerships set her on a path most artists never get to walk Why a clear vision—and the discipline to stick to it—can be a superpower How she turned frustration into creative fuel and conflict into leverage The surprising role MySpace and radio tours played in her initial success And what her story teaches us about marketing, risk-taking, and ownership But the show doesn’t stop there. Joe and OG also dive into: Grant Cardone’s 401(k) comments and whether his hot takes hold up The risks and rewards of real estate What crypto storage, insurance, and documentation mean for your financial safety net Plus, Mom’s neighbor Doug jumps in with a tax-themed trivia challenge—and a few surprising family stories to bring it all back home. Whether you’re a Swiftie, a strategist, or someone just trying to make smarter money moves, this episode delivers sharp takeaways and fresh perspectives. FULL SHOW NOTES: https://stackingbenjamins.com/all-about-taylor-swift-business-genius-1671 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

It’s Taylor Swift week in the basement, and we’re kicking things off by looking at the business behind the beats. Joe, OG, and the gang pull back the curtain on the intentional, savvy moves that took Taylor from breakout teen artist to industry powerhouse—and why her playbook might just work for your financial life, too. We’re talking about more than album drops. This episode covers: The power of controlling your own creative output Why strategic collaborations and timing matter How to avoid your own “sophomore slump”—in music or investing The underrated value of clarity, consistency, and small-but-steady improvements Then, we take a sharp turn toward the world of Roth IRAs, answering a listener question about the five-year rule and clearing up common misconceptions. If you’ve ever been confused by tax rules or unsure when you can touch your money, this one’s for you. Plus, there’s plenty more along the way: A local company stops making yardsticks (and we may be way too interested in that) Salutes to the troops, and a shoutout to basement podcasters A colonoscopy story you didn’t ask for, but will absolutely remember Whether you’re a Swiftie, an investor, or just here for the financial clarity, this episode brings strategy, insight, and unexpected takeaways you can actually use. FULL SHOW NOTES: https://stackingbenjamins.com/the-strategic-genius-of-taylor-swift-1669 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling anxious about where your money’s going? You’re not alone—and you’re not without a plan. In today’s episode, Joe is joined by OG, Mom’s neighbor Doug, and two sharp minds from the personal finance world: Paula Pant from Afford Anything and Dr. Jordan Grumet from Earn and Invest. Together, they take a deep dive into the many faces of investment risk, from the obvious to the overlooked. Because when it comes to your financial future, the real danger isn’t just volatility—it’s misunderstanding the terrain. Whether you're dipping a toe into international markets, piling into real estate, or wondering if your long-term plan can survive a little inflation, this episode will help you better understand the risks that matter—and avoid the ones that don’t. 💡 What’s inside: Why market risk feels scary—but often isn’t the real danger How liquidity and time horizon risks can quietly erode your strategy The danger of overconcentration (ahem, putting all your eggs in one ETF) What inflation, reinvestment, and credit risk mean for your future How to navigate longevity and foreign investment risks without flinching And of course, the basement wouldn’t be the basement without a few detours—including a surprise milkshake debate and Doug’s trivia segment that takes a sharp left into apple peels, Johnny Appleseed, and questionable coalition logic. If you’re ready to face the real dangers of investing—and stop fearing the ones that don’t deserve your attention—this episode’s got you covered. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Market volatility, overthinking portfolios, and why simple might be smarter. Trade wars. Tariffs. Tumbling markets. When headlines scream and your portfolio wobbles, what’s a Stacker to do? Today, we tackle how to invest confidently during uncertain times—without overcomplicating your strategy or losing sleep. We start by breaking down smart ways to manage volatility, whether you’re just getting started or already a seasoned investor. Then we dig into a great question from Stacker Ryan: should you stick with a diversified portfolio or choose a one-stop fund solution like those from Dimensional or Avantis? 🧠 In this episode: How to hedge against market swings without panicking Why keeping it simple could beat fancy fund strategies What most investors get wrong about stock market “danger” The power of a long-term mindset and how it pays off Tips for building confidence in your own investment decisions We also take a break for the TikTok Minute (yes, we found another gem), and Doug brings a trivia challenge that'll take you back to the dawn of the space race. And later, we open the mailbag: A listener asks how to plan solo for retirement ...and also wonders how much is too much for an emergency fund It’s a full basement session—investing insights, listener Q&A, and a few unexpected left turns. FULL SHOW NOTES: https://stackingbenjamins.com/talking-about-taxes-and-tariffs-in-your-investment-plan-1667 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Tariffs got you sweating? We’ve got the strategy (and the LaCroix) to help you chill. Markets are wobbling, headlines are screaming, and you’re wondering if your portfolio is about to implode. Take a deep breath—and head down to the basement. In this episode, Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle the turbulence triggered by recent tariff changes. While others panic, we’re pouring the coffee and walking you through how to think smarter (and sleep better) during uncertain times. 🔍 Inside the episode: What recent tariff changes actually mean for your money How to protect your investments when markets get shaky Why doing nothing might be the smartest move The behavioral traps investors fall into—and how to avoid them Reassurance, real talk, and your weekly dose of Doug Whether you’re tempted to sell it all or just want a little peace of mind, this episode gives you tools to stay cool, stay invested, and stay the course. Because in the basement, we don’t panic—we plan. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Entrepreneurship, financial anxiety, and a guinea pig (yes, really). When you’ve got a stuffed guinea pig on your desk and a mic in front of you, it’s only a matter of time before you talk about that one time you ate guinea pig in Peru. (Spoiler: It was pretty good.) That’s how we open today’s show—but from there, things get real. Today’s main event features Rudy Mawer, founder of 60 Day Hustle, who joins Joe Saul-Sehy to share his incredible story. Rudy grew up in a modest home in England, raised by two world-class triathletes who pushed him to pursue excellence. He didn’t come from wealth—but he did build it, and fast. Rudy opens up about: His path from sports scientist to serial entrepreneur The role mentorship and strategic networking played in his success Why legacy matters just as much as hustle His latest documentary project and what drives him today Then, we turn to a conversation sparked by actor Seth Rogen’s recent interview with Dax Shepard. Rogen confessed he’s spent years saving out of fear—and maybe missed out on life in the process. So we ask: Are you hoarding cash out of anxiety? What happens when your savings plan becomes a cage? And how can Stackers find balance between security and spontaneity? Finally, we wrap up with one heck of a weather report. Mom’s neighbor Doug recounts the epic ice storm that left him snowed in, powered down, and questioning all his life choices. (Okay, maybe not all of them—but definitely his chainsaw strategy.) As always, Doug brings the trivia heat (and a little airline history), and we share some listener reflections that tie it all together. It’s a jam-packed episode—from financial fear to frozen driveways—with a little Peruvian culinary adventure tossed in. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-get-moving-on-your-money-goals-rudy-mawer-1666 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is good debt a myth? Should we all chase FIRE? The basement panel weighs in. In today’s Financial Concepts Friday roundtable, Joe brings the basement crew together for a lively “In or Out” debate on some of the most polarizing personal finance topics out there. Are we in or out on the idea of “good debt”? Do budgets really matter when you’re just starting out? Should you talk about money with your friends and family… or is that still taboo? Joining Joe are three financial thinkers who aren’t afraid to stir the pot: Paula Pant from Afford Anything Jesse Cramer from The Personal Finance for Long Term Investors Show OG from our own basement think tank (and planning headquarters) Together, they dig into: Whether any debt can actually be considered good If living without a budget is a fast track to financial regret—or freedom The upside (and awkwardness) of open money conversations How FIRE goals like retiring by 35 sound… and feel, once you really unpack them Plus, Mom’s neighbor Doug drops by with a trivia challenge that’ll have you laughing (and maybe yelling at your speaker). And of course, we wrap up with reflections that’ll leave you both entertained and a little bit wiser. So grab a LaCroix from the mini fridge and join us in the basement—this one’s packed with laughs, insights, and hot takes on cold, hard cash. FULL SHOW NOTES: https://stackingbenjamins.com/personal-finance-most-controversial-questions-1665 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever been told to buy the biggest house you can afford... to “motivate yourself”? Or to skip insurance because “nothing bad will happen”? Yeah—us too. And we’ve got some thoughts. In this episode, Joe, OG, and Doug break down the Top 5 Worst Financial Tips they’ve ever heard—and more importantly, why taking them seriously could leave your finances in a flaming dumpster behind your dreams. From personal debt confessions to debates about extreme couponing, bad budgeting ideas, and the wild world of TikTok money myths, this episode is your roadmap to not falling for advice that sounds smart but… absolutely isn’t. In this episode: Why “buying big” won’t necessarily inspire you—it might just bankrupt you Skipping insurance to save money? We’ll show you how that plan ends Should couples really share just one checkbook? We investigate The great emergency fund vs. credit card debate When DIY everything turns into Why Did I Try? How the satire in The Joneses movie is secretly more real than you think Listener Q&A: Impact investing, private debt financing, and what it means to be an accredited investor Plus, a surprise TikTok moment, OG's thoughts on calendars, Doug’s history of April Fools’ disasters, and much more You’ll laugh, you’ll learn, and by the end, you’ll be a whole lot more confident dodging bad advice in the wild. 🎧 Tune in and stack smarter by skipping the “advice” that could sink your stack. FULL SHOW NOTES: https://stackingbenjamins.com/our-top-five-money-saving-solutions-1664 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy!  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is financial literacy missing from your life like that sock you swear went in the dryer? Tiffany Aliche, AKA The Budgetnista, is here to help you find it—minus the lint. She shares her journey to financial wholeness and takes us behind the scenes of her brand-new PBS special. Meanwhile, Joe and OG break down why financial education starts with community (not overpriced guru courses), why ‘Buy Now, Pay Later’ is the financial equivalent of eating fast food in your car—feels great now, but you’ll regret it later—and how even a trip to Texarkana can teach you a thing or two about money. Plus, a story involving World War II espionage that somehow made its way into the mix. Here’s what’s on tap this week: Kicking off Monday with a solid dose of grumpiness (and a passionate store-brand rant). Hanging with The Budgetnista—Tiffany Aliche takes us behind the scenes. Why financial literacy isn’t just about numbers—it’s about community. The sneaky financial traps that might be eating your wallet alive. Tiffany’s PBS special—how she tackled stage fright and delivered a knockout show. Headlines that made us go “Wait, WHAT?!”—including Klarna and DoorDash teaming up. ‘Buy Now, Pay Later’—why it’s like borrowing money from Future You (and Future You is not happy about it). Mortgage strategies, financial independence, and the art of dodging debt. Could you survive a week on cash only? One of us is trying (and maybe crying). Food waste: it’s not just bad for the planet—it’s silently draining your bank account. Upcoming meetups, tax tips, and basement-style money wisdom you can actually use. And if you stick around long enough, well… who knows what else might show up? FULL SHOW NOTES: https://stackingbenjamins.com/budgetnista-financial-literacy-1663 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever fallen for an investment that seemed like a sure thing... until it wasn’t? You’re not alone. Today, we shine a light on some of the worst investment advice out there—and help you steer clear of it. Joining Joe at the roundtable are: Paula Pant from Afford Anything Jesse Cramer from Personal Finance for Long-Term Investors And Don McDonald, financial pro and former astronaut (not really, but just go with it) from Talking Real Money. Infinite banking and other shiny traps – What sounds like genius often comes with fine print you’ll wish you’d read. Penny stocks and the illusion of easy money – Spoiler: if it feels like a shortcut, it's probably a detour. Equity-indexed annuities and their slick sales tactics – When someone tells you there’s “no downside,” maybe run. Gut feelings vs. data – The panel weighs in on trusting instincts vs. trusting actual math. Teachers and 403(b) plans – A quick peek behind the curtain at one of the most overlooked problem areas in personal finance. How not to invest – A rundown of red flags and hard-won wisdom from people who’ve seen the worst up close. Meanwhile, Doug brings the trivia thunder with a question about sitcom salaries—and things quickly go from Big Bang to big bucks. Whether you’ve made a misstep or are just trying to avoid one, this episode will help you tune out the noise, spot the nonsense, and build a smarter, more resilient investment plan. FULL SHOW NOTES: https://stackingbenjamins.com/our-least-favorite-investments-1662 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wondered how the top financial minds avoid disaster while the rest of us are busy panic-Googling “best investments 2024”? Today, Joe welcomes Barry Ritholtz of Ritholtz Wealth Management down to Mom’s basement for a conversation that flips typical investment advice on its head. It’s not about what to do—it’s about what not to do if you want to grow your money without losing your sanity. Barry shares battle-tested insights from his years in the trenches, covering everything from behavioral finance to market psychology and how to avoid falling for trends that make great headlines but terrible portfolios. Also in this episode: Subscription hacks you didn’t know you needed (and yes, even that one you've been ignoring since 2021). How market history can be your secret weapon—if you actually pay attention to it. Tech innovations in finance and why Barry says they're both exciting and a little terrifying. Productivity gains, AI, and whether the future is a robot that trades ETFs for you while you nap. A peek into Barry’s latest book and the big idea that might shift how you think about investing. Doug creates yet another national holiday—because what the world needs now is Bow Chicka Wow Wow Day. Stacker mailbag time! We’re diving into job loss strategies, building bulletproof emergency funds, and yes, getting into the weeds with buffer ETFs. The never-ending showdown: remote work vs. office life—where do Stackers land? And of course, Doug’s trivia will challenge your financial knowledge and possibly your respect for faux holidays. Whether you’re a seasoned investor or just now figuring out what a 401(k) actually does, this episode brings the insight, laughs, and community you’ve come to expect from the basement. 🎧 Tune in and stack smarter—with fewer missteps and a whole lot more fun. FULL SHOW NOTES: https://stackingbenjamins.com/getting-your-investments-right-with-barry-ritholtz-1661 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do weddings, wineries, and Whoppers have to do with smart investing? This week, Joe, OG, and Doug kick off the episode with stories from the road—including a surprise credit card confession that somehow involves a Burger King (because of course it does). But then the gang shifts gears and dives into real money talk, breaking down investing wisdom from the legendary Barry Ritholtz. From navigating market cycles to keeping your emotions in check, Barry’s top 10 tips serve up the kind of grounded, no-BS advice your portfolio will thank you for—especially the next time the market gets jumpy or the headlines go haywire. They also tackle what politics really mean for your investments (spoiler: maybe less than you think) and why getting your expectations right could be the most important investment decision you make. Stick around to hear a listener question that hits close to home: How should you invest for an 84-year-old mom? It’s a multigenerational money moment that brings the discussion full circle. Here’s what you’ll learn: Why market cycles matter (and how to avoid getting whiplash) The hidden dangers of investing with your heart instead of your head What Barry Ritholtz says about predicting political impacts on your portfolio How to set realistic return expectations (and why that’s surprisingly freeing) A practical investing strategy for elderly parents—without the jargon Plus: Doug’s trivia takes a nostalgic turn into the wild world of Beanie Babies FULL SHOW NOTES: https://stackingbenjamins.com/how-not-to-invest-1660 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder why some people crush their financial goals while others keep hitting snooze? Today, we’re talking about the secret sauce behind sticking to a financial plan—and no, it’s not just “wanting it more” (though that helps). Joining Joe in the basement is OG, alongside personal finance expert Jesse Kramer from The Best Interest and CFP Dana Anspach from Sensible Money. Together, they’ll break down why staying financially motivated is harder than it looks—and how to actually keep yourself on track, even when life (or a killer sale on Amazon) tries to derail you. We’ll explore why people resist financial planning (hint: it’s not always laziness), how goal-setting psychology plays into money habits, and why tracking your finances can be as powerful as tracking your fitness. Dana shares the surprising link between logging your retirement balance and saving more, while OG and Jesse tackle the age-old debate: should financial advisors be more like sports agents—pushing, coaching, and sometimes delivering the tough love? Plus, we dig into why writing things down actually works (seriously, it’s science) and how a simple mindset shift can help you finally take action. And of course, what’s a Friday without Doug’s trivia? This week, Doug takes us back to the boxing ring with a question about the legendary Joe Louis—and the sucker punch that is junk fees. ? Our roundtable throws their best guesses into the ring, but who will come out on top? Play along and see if you can take home the trivia belt! This was a great finish to a week of talking motivation and drive! From the seven steps to dynamic drive to sports agent Molly Fletcher on Wednesday and this discussion, it's a well-rounded week that should help you get up and go...even if you think YOUR get up and go got up and went. FULL SHOW NOTES: https://stackingbenjamins.com/motivation-habits-and-planning-1659 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like you're stuck in a rut, spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher, who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire. She breaks down the fine line between contentment and coasting, plus shares keys to staying at the top of your game—from managing energy to embracing adversity like a pro. But wait, there’s more! Len Penzo (yes, of LenPenzo dot com fame!) joins us as guest co-host, bringing his usual mix of wisdom, dry wit, and probably a few thoughts on sandwich prices. And if you think motivation is tough, try navigating the world of credit—because while ambition is great, bad credit can still trip you up. From student loan pitfalls to practical credit repair tips, we cover what younger folks (and honestly, all of us) need to know about keeping those numbers in check. In this episode: Molly Fletcher on Peak Performance – Lessons from a top sports agent on how to stay motivated without burning out. Complacency vs. Contentment – Are you stuck or simply satisfied? Molly breaks it down. Managing Energy Like a Pro – Tom Izzo swears by it, and so should you. Credit Crash Course – What happens when student loans go delinquent, and how to fix the damage. The Living Without Credit Debate – Is a debt-free life possible, or just a financial myth? Doug & OG’s Ski Slope Disaster – A story of poor decisions, gravity, and bruised egos (hilarious in retrospect). Len Penzo's Tips for Improving Credit Scores – Because nobody budgets quite like Len. Whether you need a motivation boost, a credit check-up, or just a good laugh at Doug’s expense, this episode has you covered. 🎧 Tune in for wisdom, financial hacks, and some après-ski storytelling you won’t want to miss! FULL SHOW NOTES: https://www.stackingbenjamins.com/find-your-dynamic-drive-molly-fletcher-1658/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter. Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday. 💰 In this episode: Why motivation fizzles out—and how to make it last The seven keys to Dynamic Drive (and how to apply them to your finances) How milestones and energy management keep you on track Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins? What cowboy fencing teaches us about peak performance (yes, that’s a thing) Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun? 👉 Listen in now and get fired up—without burning out! FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel guilty about that $7 airport coffee or the mystery fees that somehow turn your $15 DoorDash order into a $40 financial regret? You’re not alone. This episode, Joe Saul-Sehy is joined by Paula Pant (Afford Anything) and Justin Peters (The Struggle Is Real) to unravel the sneaky ways convenience drains our wallets. In this episode: Airport Food: The Ultimate Financial Heist – Why does a sad turkey sandwich cost more than a steak dinner? We investigate. Concert Tickets & Junk Fees – You found $50 tickets… but somehow the total is now $127? Yep, we’ve been there. The True Cost of Convenience – From Uber Eats to express shipping, when is paying extra worth it—and when are we just being lazy? Trivia Time: Pie Day Special! – Who knew McDonald's pie sales could spark heated debate? Well, now we all do. Wedding Costs Gone Wild – Creative ways to cut costs without making your guests eat ramen. The Ben Franklin Effect & Social Hacks – Want better connections without breaking the bank? Turns out, old Ben had some wisdom on that, too. All this, plus some hilarious personal finance confessions that will make you feel better about your last impulse buy. 🎧 Tune in, laugh, and learn how to keep more of your Benjamins! FULL SHOW NOTES: https://stackingbenjamins.com/places-we-know-were-overpaying-1656 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Choosing the Best Tax Software for Your Needs Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution. Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year. H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to. Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions. Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table. Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix. Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations. If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wondered if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he’s diving into the realities of entrepreneurship—from smart strategies to potential pitfalls. Where to start if you’re considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you? The power of systems and constraints – Why guardrails and structure matter more than unlimited freedom. Pricing strategies and finding customers – Because even the best ideas need paying customers. Entrepreneurial misconceptions – Spoiler: It’s not all Ferraris and private jets. Can your wedding be a tax deduction? – We explore the entertaining but highly questionable ways some people try to make this work. Meanwhile, Doug serves up trivia on the highest-grossing console game ever (bet you won’t guess it). And if you stick around long enough, let’s just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you know… no promises. If you’ve been toying with the idea of starting your own thing, this episode is packed with insights, real talk, and a few surprises along the way. FULL SHOW NOTES: https://stackingbenjamins.com/unlock-your-inner-entrepreneur-with-grant-sabatier-1654 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach, Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move. Why lazy portfolio management might be the smartest strategy you’ll ever adopt (spoiler: it involves less work). The power of downtime—turns out, stepping away from your money might actually make you richer. Why your future self will thank you for setting up auto-pay (hint: fewer late fees, more naps). The sneaky ways peer pressure messes with your finances—and how to keep the Joneses from running your budget. When rebalancing your portfolio is necessary…and when it’s just a fancy way to micromanage yourself. A wildly unexpected insurance claim (because finances are never boring in the basement). Oh, and Doug’s got a trivia question about a particularly controversial activity that was banned—because, apparently, not everything fun is legal. Stick around for weekend plans, final thoughts, and maybe even a surprise or two (because we like to keep you on your toes). This episode originally aired on June 10, 2022. Please disregard any mention of current events. The original show notes can be found here. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

A great financial plan isn’t just about numbers—it’s about creating a roadmap that turns dreams into reality. Today, Joe and OG take a trip down memory lane, reflecting on their favorite parts of building a great financial plan. Whether you're tackling long-term goals, fine-tuning your tax strategy, or simplifying complex decisions, they’ll walk you through the key elements that turn financial chaos into a well-oiled machine. Breaking down big goals into bite-sized wins – Because climbing a financial mountain is easier when you focus on one step at a time. The magic of tax strategies – Why a little planning now can keep more Benjamins in your pocket later. Risk management done right – Avoiding financial pitfalls so your plan stays strong, no matter what life throws your way. The power of simple solutions – Complexity doesn’t always mean better. Sometimes, the best financial strategies are the easiest to execute. The role of a financial guide – Whether you DIY your plan or bring in an expert, knowing when to get guidance is a game-changer. Meanwhile, Doug tackles a ‘Winnie the Pooh’-inspired predicament (honey jars may or may not be involved) and drops some surprising trivia on the massive market value of antidepressant drugs. If you’re ready to streamline your financial life and celebrate your progress along the way, this episode is packed with insights, strategy, and a few unexpected twists. This episode originally aired on January 18, 2023. Please disregard any mention of current events. The original show notes can be found here. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever felt overwhelmed by buying a car or managing your time? You’re not alone. Today, we tackle both topics with expert insights and a few unexpected surprises along the way. Car buying decoded – Joe sits down with Phil Reed, Senior Consumer Editor at Edmunds, to break down the best strategies for buying new or used cars, leasing vs. buying, and negotiating with dealers like a pro. The ultimate time management playbook – Paula Pant, Dominique Brown, and returning guest Carrie Smith share real-world productivity hacks—whether you're self-employed, working 9-to-5, or just trying to make better use of your day. Avoiding social media missteps at work – The team dives into the do’s and don’ts of posting while employed. Email overload? Phone calls running your life? – Smart strategies to take control of your inbox and stop wasting time on endless calls. Celebrity wealth secrets and entertainment picks – Because financial wisdom can come from surprising places. A roadside hawk encounter?! – An unexpected story that proves you never know what’s coming next. With practical advice, engaging discussions, and a few twists you won’t see coming, this episode packs in everything you need to take control of your finances and your time—without taking life too seriously. Learn more about your ad choices. Visit podcastchoices.com/adchoices

If disaster struck tomorrow, would your financial essentials be ready to grab and go? Today, Joe—along with contributors Paula Pant from Afford Anything, Jesse Cramer from Personal Finance for Long-Term Investors, and our resident expert OG—assemble the ultimate financial go bag. Meanwhile, Doug handles his usual duties as announcer, trivia master, and general chaos instigator. The must-have documents – Passports, Social Security cards, insurance policies... what belongs in your bag, and what can stay in the filing cabinet? Cash vs. digital access – How much should you keep in physical cash? And is gold really a smart emergency asset, or just a really heavy way to slow yourself down? Estate planning and emergency preparedness – The financial moves today that can make a crisis less stressful later. Password managers: genius or a liability? – We debate whether your digital keys should be stored in the cloud, on paper, or tattooed in invisible ink. Trivia showdown: Doug tests the team’s knowledge with a question that (probably) has nothing to do with financial preparedness. Campus co-op stores and Harvard history—why are we talking about this? You’ll find out. If you’ve been meaning to get your financial house in order for emergencies, this episode has everything you need to build your own financial go bag—without overpacking. FULL SHOW NOTES: https://stackingbenjamins.com/your-financial-go-bag-1650 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is your insurance setup rock-solid, or are you unknowingly leaving gaps that could cost you big time? Today, we break down the essentials of managing risk in our no-nonsense (but totally entertaining) insurance guide. How much coverage do you really need? We tackle the must-haves and the unnecessary add-ons that might just be draining your wallet. Auto, home, life, and disability insurance—what’s essential and what’s overkill? We walk through the key policies that keep you protected without breaking the bank. Oddball insurance policies—are they worth it? From pet insurance to that ‘just in case’ coverage you saw on late-night TV, we separate the smart buys from the money traps. A TikTok minute that perfectly sums up the difference between dogs and cats. Trust us, you’ll relate. Listener questions: Breaking up with a financial advisor—when it’s time to walk away and how to do it right. Insurance company showdown: Who’s the biggest player in the game, and does size really matter? DIY money moves: How to take over your own investment accounts without making costly mistakes. Stackers, this episode is packed with tips, laughs, and real-world insights to help you protect what matters—without wasting a dime. Don't miss it! Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like your budget is running you instead of the other way around? Today, we’re bringing in Shaun Morgan from The Teacher Money Show and Kristin Wade, budgeting coach at My Budget Coach, to help you flip the script. They’ll share how tracking your expenses is the first (and easiest) step toward financial freedom, why budgeting shouldn’t feel like punishment, and how to make your money work without the guilt. But wait—there’s more! We’re diving into creative ways to gamify saving, some unexpected solutions for real estate dilemmas (hint: selling isn’t your only option), and why sometimes renting out your home might be the smarter move. And of course, we sprinkle in some personal stories, real-life lessons, and a few side tangents that may or may not include baseball, beer trends, and an ode to Steve Jobs. What’s Inside Today’s Episode: Budgeting Basics: How to make your spending work for you. Tracking Expenses 101: The first step toward a stress-free financial plan. Finding the Right Budgeting Tools: What actually works? Gamifying Your Finances: How to make saving and budgeting fun (yes, fun!). Accountability & Motivation: Why most people quit budgeting—and how to stick with it. Turning Real Estate Woes Into Wins: If your house won’t sell, here’s what to do next. Renting vs. Selling: When keeping your home might be the smarter play. Running a Business on a Budget: The hidden costs and how to stay profitable. Community Shoutouts & Listener Feedback: Your wins, your questions, and more. Random Topic: Cancun adventures and off-the-cuff fun. Key Takeaways from the Episode: ✔️ Budgeting doesn’t mean restriction—it means intentional spending. ✔️ Tracking your money is like using a GPS—it keeps you from getting lost. ✔️ Real estate has more options than just “sell or stay put.” Renting could be a game-changer. ✔️ You don’t have to budget alone. The right tools and accountability partners make all the difference. ✔️ Even Cancun has budgeting lessons. (Or at least a few good stories.) Tune in now and take the first step toward mastering your budget—without making it feel like a chore. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-take-control-of-your-budget-1648 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is it time to break up with international stocks? They’ve been underperforming U.S. markets for years, so should we finally call it quits, or is there still hope for a global comeback? On today’s episode, Joe, OG, Paula Pant, and Jesse Cramer dig into the great international investing debate. Are international funds a lost cause? The panel unpacks why they’ve lagged U.S. stocks and whether diversification still makes sense. Beyond stocks: Exploring other asset classes—private equity, real estate, commodities, and collectibles (because who doesn’t want to invest in Beanie Babies and vintage lunchboxes?). The $3 coin mystery: Yep, that was a thing. And yes, it’s as weird as it sounds. Election results and wooden nickels: The intersection of money, history, and questionable currency choices. Weekend plans and podcast highlights: Because investing is important, but so is having fun. Of course, it wouldn’t be a Stacking Benjamins episode without some friendly debate, expert insights, and the occasional off-the-wall tangent. Tune in for a laid-back but insightful conversation on making smart investment decisions! FULL SHOW NOTES: https://stackingbenjamins.com/is-international-investing-dead-1647 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever experienced the gut-wrenching moment of losing a job—or worried about what you’d do if it happened? Today, we tackle how to prepare, what to do immediately, and the smartest moves to protect your finances if your job ever disappears. From building an emergency fund to making the most of employer benefits, we’ll walk you through the steps to keep your financial house in order when life throws a curveball. But that’s not all. Estate planning gets a shake-up thanks to the new Secure Act 2.0, and we’re diving into what it means for inherited Roth IRAs (hint: the government has new rules, and you’ll want to know them). And because we can’t resist a good detour, we also explore the real cost of horse ownership (spoiler: it’s more than just hay money) and why tide pooling is more financially educational than you’d think. All that, plus trivia, TikTok wisdom (or nonsense), and plenty of lively discussion from the basement crew. What’s Inside Today’s Episode: Job Loss Survival Guide: How to prepare before, during, and after a layoff. Emergency Fund Essentials: Why you need one (and how much is enough). Navigating Employer Benefits: Making the most of what’s available before you leave. Secure Act 2.0 & Estate Planning: The new rules around inherited Roth IRAs. Trivia & The TikTok Minute: Because questionable financial advice is always worth dissecting. Horse Stackers & Expensive Hobbies: Ever wonder what it really costs to own a horse? We break it down. Tide Pooling Adventures: A financial lesson wrapped in sea creatures and crashing waves. Key Takeaways from the Episode: ✔️ Job security is a myth—be ready. Build that emergency fund, update your resume, and keep networking. ✔️ Your employer’s benefits might be your hidden lifeline. Know what’s available before you walk out the door. ✔️ Secure Act 2.0 changes estate planning. If you’re inheriting a Roth IRA, don’t assume the old rules apply. ✔️ Horses aren’t just expensive—they’re financial black holes. But that won’t stop people from trying. ✔️ Tide pooling might be the best investment lesson in disguise. Patience, observation, and avoiding getting pinched—it’s practically a stock market metaphor. Tune in now to make sure you’re financially prepared—whether it’s for job loss, estate planning changes, or just the unexpected expenses of a very expensive hobby. FULL SHOW NOTES: https://stackingbenjamins.com/spring-cleaning-your-estate-plan-1646 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling stuck in your financial plan—or maybe just in life in general? Whether it’s your money, career, or day-to-day habits, a little innovation can go a long way. Today, we’re breaking down how to rethink and restructure your approach to financial planning and work-life balance using lessons from Microsoft (yes, the Xbox folks). Dean Carignan and JoAnn Garbin insights on how to build a system for innovation—because the best financial plans (and lives) aren’t built by accident. Meanwhile, a woman was scammed out of her savings, and a major financial company had to pay a fine—even though they didn’t actually rip her off. What happened? And what does it mean for how we protect our own money? We’ll break it all down. Elsewhere in the episode, we discuss why trusted contact forms are crucial for safeguarding elderly relatives’ finances, how OG wants you to rethink your daily money habits, and why the Xbox case study holds lessons for designing a better financial plan. Plus, Doug has thoughts on podcast innovation, trivia, and—because it wouldn’t be a proper basement gathering without it—a hot take or two. What’s Inside Today’s Episode: A Woman Gets Scammed, But Who Pays the Price? A big financial firm faces a fine—without actually doing anything wrong. The Xbox Case Study: What Microsoft’s innovation strategy can teach you about structuring your financial future. Financial Planning Innovations: Why thinking like an engineer (or a game developer) might help you build a better plan. Rethinking Your Everyday Financial Habits: OG’s take on how small changes lead to big results. Trusted Contact Forms & Safeguarding Elderly Relatives: A simple but powerful tool to prevent financial disasters. Charitable Giving Strategies: How to give smarter, not just more. Doug’s Trivia Time: A deep dive into financial (and podcast) innovation—because why not? Building a Network in Retirement: Why relationships matter just as much as money when designing your post-work life. Key Takeaways from the Episode: You can’t just wing it with your finances. Microsoft doesn’t build Xbox consoles on a whim—your financial future needs the same level of structured innovation. Don’t assume big financial firms will protect you. A major company had to pay up even though they weren’t the scammers—learn how to protect yourself before something happens. Small financial tweaks can make a massive difference. Just like product innovations, incremental changes in your money habits can lead to big wins over time. Retirement isn’t just about the money. You need a network, a purpose, and a strategy—or you’ll find yourself wealthier but bored out of your mind. Tune in now to learn how to bring structured innovation into your finances, career, and life! FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-innovation-1645 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Love is in the air—and so are overpriced flowers, extravagant dinners, and some serious credit card regrets. In today’s episode, we tackle the financial pressure of Valentine’s Day and show you how to keep the romance alive without setting your wallet on fire. Joining us are financial pros Jesse Cramer, Sarah Catherine Gutierrez, and Len Penzo, who help us break down: The shocking reality of Valentine's Day spending – Who’s dropping the most cash, and is it really worth it? Avoiding post-holiday financial heartbreak – Strategies to celebrate without swiping yourself into debt. Creative alternatives to overpriced traditions – Ditch the $200 steak dinner and try these fun, budget-friendly ideas instead. The cost of love – From babysitting fees to restaurant markups, where is your money really going? Romantic gestures that don’t break the bank – Because a handwritten note might just score you more points than a last-minute gas station bouquet. The key to financial harmony in relationships – Talking money before someone drops a fortune on a gift they think you’ll love (but don’t). Listener tips and budget-friendly adventures – Stackers share their best ideas for a Valentine’s Day that’s memorable and affordable. Plus, we’ve got trivia, technical mishaps (because what’s love without a little chaos?), and some surprise financial wisdom that might just save your next date night. Stack your love life and your Benjamins—tune in now! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Just when you thought Wall Street had run out of ways to package up risky investments and slap a shiny label on them—here we go again. Today, Joe and OG break down yet another overcomplicated, high-fee, and completely unnecessary financial product. Whether it’s preying on investor fears, promising market-proof returns, or just outright nonsense, we’ll help you spot the warning signs before you end up with a portfolio full of regret. But that’s not all. A viral TikTok tip about hiring your family members for tax benefits has been making the rounds, so we’ll dive into whether this is actually a genius tax strategy or just another case of the internet handing out half-baked financial advice. Plus, a listener asks about breaking into financial planning, and we lay out what it really takes—beyond the certifications and credentials (spoiler: sales skills matter). And Doug brings us a trivia question about one of the greatest art heists in history, proving that sometimes the best investment is knowing how to disappear with the Mona Lisa. Also: Joe saw ‘Wicked’ and has thoughts—mostly about how much better Wonka was. What’s Inside Today’s Episode: The Latest Wall Street Gimmick: A financial product you definitely don’t need. Understanding Risky Investments: How to tell if an ETF, structured note, or annuity is actually worth your time. Hiring Family for Tax Benefits: A TikTok tax hack that might actually work—if you follow the rules. Trivia Time with Doug: One of the most famous art heists in history. Breaking Into Financial Planning: What it takes to switch careers and make it in the industry. Community Feedback & Upcoming Episodes: A sneak peek at what’s coming next (including our Valentine’s Day special). Episode Highlights: What’s in a Name? The ridiculous branding that makes bad investment products sound good. Bitcoin Meets Structured Protection: The ETF that no one asked for but someone, somewhere, will buy. Hiring Your Kids for Tax Savings: A loophole with some very real fine print. How to Become a Financial Planner: Beyond certifications—why understanding people (and sales) matters. Doug’s Trivia: If you could steal any piece of art, what would it be? Asking for a friend. Joe’s ‘Wicked’ Review: Spoiler: Wonka was better. Huge Resource Mentioned in This Episode: Want to learn more about structured investments? (Just kidding, you really don’t.) Tune in now and learn how to dodge the latest Wall Street nonsense while making smarter money moves. FULL SHOW NOTES: https://stackingbenjamins.com/new-crypto-etfs-1643 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Swipe right on financial stability or get ghosted by your savings? While Joe's mom yells upstairs about who left the empty milk carton in the fridge (seriously, who does that?), we’re diving into the messy, complicated, and sometimes hilarious world of your relationship with money. Are you in a stable, long-term commitment with your finances, or are you stuck in a toxic on-again, off-again affair with impulse spending? Special guest Shannah Game, certified financial planner and author of Unraveling Your Relationship with Money, joins us to decode the emotional baggage we bring to our bank accounts. Meanwhile, Doug swears he’s figured out how to “game” the stock market using AI—spoiler alert: it involves a Magic 8-Ball. We also tackle some questionable dating preferences (because who doesn’t want to know if their financial habits make them swipeable?) and unpack the latest market shake-ups. In this episode: 🏈 Super Bowl takeaways and why Doug insists commercials count as “investing research” 💰 Your financial habits might just be the biggest red flag in your dating life 🎙️ Shannah Game on money, mindset, and making smarter choices 💔 Rollercoaster relationships—with your wallet and beyond 🧐 Money manifestos: How to rewrite your financial story (without Mom intervening) 🤖 AI's impact on investing, and why OG isn't buying it (literally) 📈 How to keep your portfolio from ghosting you 🤯 Hidden track: Doug’s latest deep dive into bizarre facts—this time, dinosaur vomit Will your money habits lead to a lifetime of wealth—or will your wallet break up with you via text? Tune in and find out! FULL SHOW NOTES: https://www.stackingbenjamins.com/relationship-with-money-financial-habits-sb1642 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is automating your finances the key to effortless money management, or a one-way ticket to financial autopilot disaster? Paula Pant, Jesse Cramer, and Doc G join us to navigate the fine line between automation genius and accidental money mayhem. Done right, automation saves you time and stress. Done wrong? You might be funding a forgotten gym membership for the next five years. 😬 What’s Inside This Episode? 💰 The Power of Automation – How strategic automation can make your financial life simpler, more efficient, and stress-free. 🤖 What to Automate & What to Keep Manual – Should you set bills to auto-pay, or will that lead to mysterious charges on your credit card? 📊 High-Tech Money Tools: Are They Worth It? – Todoist, Notion, and other techy automation tricks—are they game-changers or just digital clutter? 💡 Personal Automation Hacks – How the panel automates their finances like pros (without losing control of their money). 🎭 The Dark Side of Automation – Horror stories of overdraft surprises, vanishing paychecks, and auto-pay regret. 📢 Stacker Debate: Should You Automate Everything? – The great automation showdown—when automation helps and when it hurts. ✨ Special Bonus: The Worst Things to Automate – Some things should NEVER be on autopilot. Find out what financial automation fails made our list. Takeaways for Smart Stackers: ✅ Automation = Freedom (When Used Wisely). The right balance saves you time while keeping you in control. ✅ Auto-pay is great—until it isn’t. Track subscriptions and bills so you don’t end up paying for things you don’t use. ✅ Manual check-ins keep you financially sharp. Even with automation, you need to review your money regularly. ✅ Tech tools can help—but they’re not magic. The best system is the one you actually use. 🎧 Hit play now and rethink your approach to automation before it outsmarts you! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do scammers, fancy doors, and Twinkies have in common? Turns out, more than you think! Today, Joe, OG, and Doug take you on a wild ride through financial scams, fraud prevention, tax implications of dual residency, and... the surprising link between door quality and financial stability. (Yeah, we didn’t see that one coming either.) What’s Inside This Episode? 🕵️‍♂️ Scams, Scams Everywhere! – From identity fraud to the trendy new "deed theft" scam, learn how to protect yourself before a scammer claims your house faster than you can say "that wasn't in the budget." 💳 Fraud-Proofing Your Finances – Why setting up credit monitoring, checking your bills, and paying attention to sketchy emails can save you thousands in headaches. 🚪 The TikTok Minute: What Do Soft Close Doors Say About Your Wealth? – Is your financial future written in the way your doors shut? Find out why door noises might reveal more about your bank balance than your credit score. 🧾 State Taxes & Dual Residency: The Sneaky Costs of Living in Two Places – Thinking about snowbirding to Florida or keeping a backup home in another state? We break down what you NEED to know before state tax authorities come knocking. 🤖 Password Security & The Quantum Computing Takeover – Is the future of passwords doomed? What you should be doing now to keep your Twinkies—and your bank accounts—safe. 🍕 Pizza Cutting Controversy & Nostalgic Minivan Stories – Because what’s a Stacking Adventures episode without a little debate, a little reminiscing, and a whole lot of questionable opinions on pizza slicing? 🍰 Twinkies Trivia: A Deep-Dive into the Snack That Never Dies – Have scientists unlocked the secret of Twinkie immortality? More importantly, should Twinkies be considered part of a solid financial plan? (Spoiler: probably not, but let’s discuss.) 📢 Stacker Questions & Community Fun – Helping a listener navigate dual residency tax headaches + a special meetup announcement! Takeaways for Smart Stackers: ✅ If it sounds too good to be true, it’s a scam. Seriously. Trust your gut, not the email from "Prince Jeff of Nigeria." ✅ Your finances need monitoring, just like your snack stash. Set up credit alerts and check your accounts weekly to avoid surprises. ✅ Moving states for tax savings? Do the math first. Dual residency isn’t always the loophole people think it is. ✅ Twinkies may last forever, but financial security requires maintenance. A solid money plan beats a stockpile of snacks (but only slightly). 🎧 Hit play now for a mix of financial wisdom, scam-prevention tips, and just the right amount of Twinkie-fueled fun! Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Retirement planning isn’t about waiting until 65—it’s about setting yourself up for a life you love starting right now! Today, Certified Financial Planner Benjamin Brant joins us to challenge traditional retirement thinking. What We Cover: ✅ Retirement planning starts now, not later – Why waiting to plan is the biggest mistake you can make. ✅ Dream big, but expect some ‘bad data’ – How testing financial plans (and life plans!) helps you refine your future. ✅ Why trust beats performance in financial planning – A new study shows that your advisor’s returns matter less than their integrity. ✅ The Monte Carlo simulation debate – What this financial tool actually tells you (and what it doesn’t). ✅ Childhood dreams, stand-up comedy, and time travel? – How revisiting past joys can shape a meaningful retirement. ✅ Choosing the right financial advisor – The #1 factor to look for before handing over your portfolio. Key Takeaways: 💡 Retirement isn’t a number—it’s a mindset. The earlier you start thinking about what brings you joy, the better. 💡 Financial planning isn’t perfect science. Bad data, trial-and-error, and adjusting your plan over time? Totally normal. 💡 Trust is your biggest investment. A good financial advisor isn’t just about returns—they’re about guidance you can rely on. Grab your favorite drink (coffee, bourbon—you choose!) and let’s stack some wisdom for your future self. 🎧 Hit play now and start building your best retirement today! FULL SHOW NOTES: https://stackingbenjamins.com/find-your-fulfillment-in-retirement-Benjamin-Brandt-1639 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever dreamt of quitting your job early and sipping piña coladas on a beach? Before you tell your boss what to do with that job and start booking your one-way ticket to paradise, today’s roundtable might make you think twice. Join Jesse Cramer from The Best Interest, Paula Pant from Afford Anything, and our own OG as they break down the case against early retirement. The gang’s here to challenge the “quit work, retire early” dream and explore whether it’s really as awesome as it sounds—or if there are a few catches you haven’t considered. The conversation gets into the nitty-gritty of why early retirement might not be the smooth ride some people think it is. From the psychological toll of too much free time to the unexpected financial hurdles, our panelists share the real stories behind the headlines. What’s the balance between financial freedom and a fulfilling life? Can you really retire early without regret, or does the cost of quitting work too soon outweigh the benefits? And don’t forget about Doug’s wicked trivia challenge! FULL SHOW NOTES: https://stackingbenjamins.com/the-case-against-early-retirement-1638 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wondered if you’re better off building your own target date fund instead of relying on a one-size-fits-all option? We’re diving into whether crafting your own investment mix is worth the effort, potentially saving you fees and giving you more control over your portfolio. But even the pros get it wrong sometimes—just ask Vanguard. We’re covering the major settlement they’re facing over misleading statements about taxes and target date funds, proving that even the big guys make costly mistakes. Meanwhile, a listener asks a great question about balancing tax optimization with financial flexibility—because what good is a perfectly tax-efficient plan if it ties your hands when you need cash? Plus, Doug takes us back to the origins of the gasoline-driven automobile, and there’s even an unexpected run-in with a Supreme Court justice (because why not?). And of course, we’ve got a TikTok moment that’ll have you questioning life choices and a few financial misconceptions that might just make you rethink your approach to money. What’s Inside Today’s Episode: Vanguard’s Costly Mistake: The settlement every investor should know about. Understanding Mutual Fund Taxes: How taxes sneak up on your investments. DIY Target Date Funds: Pros, cons, and when to consider building your own. Trivia Time with Doug: The surprising story behind the gasoline-driven car. The TikTok Minute: Financial advice that may (or may not) be worth your time. Financial Flexibility vs. Tax Optimization: Finding the balance in your strategy. Community Announcements & Meetups: Where to find us next. Episode Highlights: Vanguard’s Legal Trouble: What happened, and what it means for investors. Mutual Fund Taxation: Avoiding unexpected tax bills. Should You Build Your Own Target Date Fund? We break down the numbers. Listener Q&A: How to stay tax-efficient while keeping access to your cash. Doug’s Trivia: Who REALLY built the first gasoline-powered car? An Unexpected Supreme Court Encounter: Because that’s just how things go around here. Resources Mentioned in This Episode: Learn more about Vanguard’s target date fund settlement in our show notes: https://www.stackingbenjamins.com/vanguard-target-retirement-trouble-1637 Read up on mutual fund tax strategies and more by signing up for our 201 newsletter! https://stackingbenjamins.com/201 Tune in now and get the insights you need to build a smarter investment strategy—without falling into costly traps. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What’s really standing between you and your financial goals? In today’s mentor, Jessica Moorhouse—financial counselor, podcast host, and author of Everything But Money—joins Joe to dive into the mental and emotional side of managing money. Jessica shares her journey with therapy, how relationships shape our financial habits, and the role of self-talk in creating a healthier money mindset. Whether you’re feeling stuck or just want a fresh perspective, this interview offers practical tools to help you take control of your financial future. In our headline segment, we explore the concept of a “no-buy” list—a clever strategy one woman used to pay off $34,000 in debt. Learn how gamifying financial goals can make saving more manageable—and even fun! Whether it’s cutting back on unnecessary spending or finding creative ways to save, this segment will inspire you to rethink how you approach your financial challenges. Here’s what we cover today: Saluting our troops—and wondering why Doug still doesn’t have a Navy Federal mug Meet Jessica Moorhouse: Financial counselor, podcast host, and author of Everything But Money Unlocking the connection between your money mindset and financial success with Jessica How Jessica’s personal journey and therapy shaped her healthier money mindset Unpacking how emotions and relationships impact financial habits Understanding rational vs. irrational guilt—and how it affects your money decisions Recognizing irrational guilt and why it’s critical to tackle it Celebrating financial wins and overcoming the fear that holds you back Jessica’s book Everything But Money—and why it’s a must-read for anyone improving their financial mindset Sneak peek: What’s next on the More Money Podcast with Jessica Moorhouse Doug’s historical trivia: Financial lessons from the past Gamifying financial goals: Make saving and investing fun and rewarding Real-life success stories: The No Buy Challenge and how it helped pay off $34,000 in debt Join our community: Upcoming meetups and ways to get involved Final thoughts and takeaways: Simple actions you can start today to improve your financial mindset FULL SHOW NOTES: https://stackingbenjamins.com/changing-your-money-self-talk-jessica-moorhouse-1636 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Do financial boogeymen haunt your dreams? You’re not alone. Today, we’re diving into the worries that keep even the most seasoned finance nerds up at night. From concerns about index fund concentration to the fear of market manipulation and obsession with asset allocation, this episode tackles it all with insight and a healthy dose of perspective. Joining Joe and OG in the basement is an all-star panel: Paula Pant from Afford Anything, Jesse Cramer from Best Interest, and Dr. Jordan Grumet from Earn and Invest. Together, they’ll share strategies to conquer financial fears by staying calm, focusing on the big picture, and sticking to sound investment principles. And don’t miss the kickoff of the year-long Stacking Benjamins Trivia Challenge! It’s packed with brain-busting questions, lively debates, and, yes, the occasional cat butt reference (because it’s still the basement, after all). What’s Inside Today’s Episode: Meet the Contributors: Paula, Jesse, and Dr. Grumet join the crew. Index Fund Concentration: Are index funds too risky? The panel weighs in. Addressing Financial Fears: From market scams to fraud and manipulation, here’s how to keep your cool. Trivia Challenge Kickoff: A brand-new Stacking Benjamins tradition begins. Market Efficiency and Insider Trading: Can you really beat the market? Asset Allocation Obsession: Why overthinking your portfolio can be your worst enemy. Upcoming Episodes: What’s next on the Stacking Benjamins calendar? Highlights from the Episode: Index Fund Concentration: The crew discusses whether having too much of the market in a few big players is a recipe for disaster. Financial Fears: Practical advice for keeping anxiety at bay when market volatility hits. Market Scams and Frauds: How to spot them and protect yourself. Trivia Time: A heated debate over billionaire counts, complete with unforgettable banter. Asset Allocation: Tips for avoiding paralysis by analysis and focusing on long-term strategies. Resources Mentioned in the Episode: Learn more from Paula Pant at Afford Anything. Explore Jesse Cramer’s insights at Best Interest. Dive into Dr. Jordan Grumet’s conversations at Earn and Invest. FULL SHOW NOTES: https://stackingbenjamins.com/financial-worries-and-what-to-do-about-it-1635 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Tune in now and learn how to leave your financial fears in the dust while keeping your money goals on track. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling like the stock market is a high-stakes game of pinball lately? Not sure how to steady your hand when it comes to retirement accounts? In this episode, we tackle the rollercoaster of market volatility with actionable strategies to keep your retirement plans on track. Learn how to create an Investment Policy Statement, whether a Roth IRA still deserves a spot in your portfolio, and smart ways to withdraw from retirement funds without triggering costly mistakes. Plus, discover why trying to time the market is like predicting the weather with a Magic 8-Ball. Doug shares a tale involving a Chinese couple and some financial advice that’s worth sticking around for. Whether you’re building financial independence or refining your retirement strategy, this episode has you covered. What We Cover Today: Market Rollercoaster Madness: Stock, Bitcoin, and why patience pays off. Creating an Investment Policy Statement: Stay calm and strategy on. Listener Q&A: Chris from Georgia asks about retirement withdrawals. Roth IRA Reboot: Is it still a go-to for your portfolio? Financial Headlines: Why tuning out the noise can save your sanity. Trivia Time with Doug: A historical nugget tied to financial wisdom. Highlights from the Episode: Market Volatility Analysis: Stocks and Bitcoin – what’s up, what’s down, and what you should do about it. Listener Question: Tapping retirement accounts – the dos, don’ts, and what-ifs. Investment Philosophy: Why having a policy statement is the ultimate stress reliever. TikTok Minute: A social media take that’ll have you rethinking the advice you see online. New Year’s Resolutions: Money nicknames, quirky goals, and strategies for staying on track. Closing Remarks: Key takeaways to help guide your financial decisions. Resources Mentioned in This Episode: Sign up for our Free Weekly Newsletter for insights, tips, and resources: https://stackingbenjamins.com/201 Join us at our Upcoming Meetups to connect and learn more: https://stackingbenjamins.com/meetup. FULL SHOW NOTES: https://stackingbenjamins.com/stock-market-volatility-beginning-of-2025-1634 Tune in now and take the first step toward turning market madness into financial confidence. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling overwhelmed by debt or unsure how to navigate the fast-paced world of financial advice online? We’ve got you covered! This episode features Debt Relief Advocate Natalia Brown from National Debt Relief, who shares practical tips to climb out of financial trouble and steer clear of predatory practices. But that’s not all—we dive into the Wild West of TikTok crypto advice, where nearly 70% of content is misleading enough to derail your financial plans. Joe and OG break it all down with their trademark insight, helping you sort fact from fiction in the world of digital finance. Here’s what you’ll learn: Tackling Debt: Natalia Brown’s strategies for overcoming financial stress and avoiding common traps. Crypto Caution: Why TikTok might not be the best place for your financial advice (and what to watch out for). Credit vs. Stability: The difference between obsessing over credit scores and focusing on long-term financial health. Digital Disclaimers: How transparency (or lack thereof) online can impact your wallet. And of course, no episode is complete without Doug’s trivia to keep things lively and unpredictable. Whether you’re tackling debt, dabbling in crypto, or just trying to stay informed, this episode will leave you with actionable advice and a fresh perspective on navigating today’s financial challenges. Tune in and take the first step toward a more confident financial future! FULL SHOW NOTES: https://stackingbenjamins.com/how-to-eliminate-debt-once-and-for-all-natalia-brown-1633 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ready to ring in the new year with a twist? On this episode of Stacking Benjamins, we consult the one and only Magic 8-Ball to make our bold predictions for 2025. Will the stock market be riding high, or is it headed for a tumble? What’s next for Bitcoin, and can Taylor Swift’s love life predict the future? Join Joe, OG, Len Penzo, and Mindy Jensen as they tap into the 8-Ball’s mystical power (or maybe just have a laugh trying) to forecast the year ahead. But before we get too caught up in the crystal ball, we take a look back at last year’s predictions. The 8-Ball hit some big marks, like predicting Nvidia’s rise, but it also missed a few. Along the way, Mindy shares her early (and hilarious) experience with Berkshire Hathaway, sparking a fun conversation about investing wisdom. And of course, Len brings his signature humor, diving into everything from crypto to drones to the wild world of Taylor Swift fandom. If you’re in the mood for financial insights, pop culture predictions, and a whole lot of fun, this episode is for you. Whether the Magic 8-Ball is on the money or way off the mark, you won’t want to miss our 2025 forecast. Grab your popcorn, sit back, and join us for an episode packed with surprises! FULL SHOW NOTES: https://stackingbenjamins.com/magic-8-ball-2024-recap-2025-predictions-1632 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Can you save too much? Spoiler alert: absolutely. On today’s episode, Joe, OG, and Neighbor Doug tackle a financial pitfall many Stackers don’t think about—oversaving. Yes, socking away cash for the future is important, but at what cost? People often work extra hours, miss family dinners, skip vacations, and end up with regret instead of memories. The real tragedy? You can’t deposit lost time back into your bank account. We’ll share stories of people who saved so much they missed out on the life they were saving for, and we’ll dive into strategies to strike a better balance. From stress-testing your financial plan to understanding your personal inflation rate, we’ve got the tools to help you live for today and plan for tomorrow. And of course, we’ve got Doug’s trivia, a TikTok minute that might make you laugh out loud, and plenty of basement banter to keep things light. What’s Inside This Episode Opening: Joe, OG, and Doug kick things off with a mix of jokes, announcements, and OG’s latest attempt to seem cooler than he is. The Real Cost of Oversaving: Stories of people who worked too hard, saved too much, and missed the moments that really mattered. How to Avoid Regret: Strategies to prioritize both your financial goals and your quality of life. Taking Breaks to Save Your Sanity: Burnout isn’t just bad for your mental health—it’s bad for your wallet too. The TikTok Minute: Doug’s take on energy conservation (or as he calls it, “saving money with style”). Trivia Time: Doug’s question of the day—proof that you never stop learning in the basement. Listener Question: How do you plan for retirement when inflation keeps messing with the math? Joe and OG break it down. Stress-Testing Your Financial Plan: Find the cracks now, so your future self doesn’t have to. Amazon Purchases vs. Amazon Stock: A fun exercise that might make you rethink those impulse buys—or laugh at them, at least. Wrapping Up: Final thoughts, laughs, and a classic basement sendoff. Don’t Miss Why the “save everything” mentality can lead to serious regret—and how to avoid it. A hilarious dinner story involving Joe’s nephews and a lesson in why you never leave Doug in charge of the menu. A nod to Hell or High Water—because what’s a day in the basement without a classic callback? Join the Fun Ever feel like you’re missing out because you’re too focused on saving? Share your story with us, and let’s talk about finding that perfect balance. And don’t forget to tune in on Friday for more laughs, lessons, and, of course, Doug’s dubious wisdom. FULL SHOW NOTES: https://stackingbenjamins.com/are-you-saving-too-much-for-retirement-1631 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling like life’s demands have you tied up in knots while your financial future seems like a moving target? Time to take charge! Today in the basement, Anthony O'Neill pulls up a chair and shows you how to claim the head seat at your own table. He breaks down the power of having a personal vision, making intentional decisions that align with your goals, and being a stellar steward of your time and opportunities. But that’s not all—we’re looking ahead with some of the biggest names in tech. What do Bill Gates, Sam Altman, and other visionaries think 2025 will bring? (Spoiler alert: AI isn’t just for sci-fi anymore.) We’ll chat about how these changes will impact your work life and share some practical steps to stay ahead. And because life isn’t just about finances, the crew wraps things up with their latest binge-worthy TV and movie picks. It’s time to stack your entertainment queue as high as your Benjamins. What’s Inside This Episode 🎙️ Texarkana Vibes: A chilly morning, winter woes, and Doug’s favorite Mickey Mouse mug. 🌟 Anthony O’Neill’s Vision: Practical tips to align your financial and personal goals. 🛠️ Stewardship 101: Why managing your opportunities well is a game-changer. 🤖 2025 Tech Predictions: How AI might reshape your work life and what to do now to stay ahead. 🎥 Entertainment Corner: The gang’s TV and movie picks to keep you entertained. Episode Highlights Winter kicks off with Texarkana shivers, travel plans, and Doug waxing poetic about his mug collection. Anthony O’Neill’s advice: Learn how to take control of your life by building a clear personal vision and aligning your goals with your actions. The importance of stewardship: Make the most of your opportunities and turn them into stepping stones for success. A tech-driven future: Bill Gates, Sam Altman, and other leaders weigh in on AI’s role in shaping the workplace of 2025. Fear and finances: How fear might be holding you back and ways to overcome it. Basement banter: A round-up of the crew’s current TV and movie obsessions. Want More? Anthony O'Neal shares details about his exciting new project, Take Your Seat at the Table, plus some special offers just for you. And of course, Doug treats us to one of his legendary historical anecdotes (did he mention he’s a trivia champ?). Stack Your Listening Queue This episode is packed tighter than Mom’s basement freezer. Whether you're looking for financial wisdom, tech trends, or just some good laughs with the crew, we’ve got you covered. Pull up a chair—there’s always room at the table in the basement. The link to Anthony's book: https://stackingbenjamins.com/takecontrol FULL SHOW NOTES: https://stackingbenjamins.com/define-your-purpose-in-life-anthony-oneal-1630 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling a little queasy about your financial plans for 2025? Fear not! Today, Joe steps out of the cozy basement and straight into the bustling chaos of Manhattan to bring you top-tier advice from some of the brightest financial minds. Joined by Paula Pant from Afford Anything, Nick Magiulli, author of the Of Dollars and Data blog, and Doc G from the Earn & Invest Podcast, this powerhouse panel digs into the money missteps you’ll want to dodge in the year ahead. From tackling FOMO in investments to learning why small, consistent changes are your financial BFFs, this episode is packed with practical tips to help you make 2025 a year of smart money moves (and fewer facepalms). What’s Inside: Meet our stellar guests and hear how New York City inspired their financial insights. Discover why chasing the next big investment trend could leave you behind. Learn how an investment policy statement can keep your goals on track. Avoid analysis paralysis when market uncertainty strikes. Uncover strategies to navigate political uncertainty without losing sleep (or cash). Dive into real estate trends, historical data, and staying focused on what you can control. Understand the power of spending on what truly matters to you. Find out why gradual changes beat impulsive overhauls every time. Learn how doubling down on bad decisions is like hitting a pothole and accelerating instead of swerving. Episode Highlights: Meet the Guests: Get to know Paula Pant, Nick Magiulli, and Doc G as they join Joe in the Big Apple for some big-time financial lessons. NYC Moments: Joe shares a peek into his adventures in Manhattan—yes, it’s a jungle out there. Investment FOMO: Why chasing trends could cost you (and how to avoid it). Building an Investment Policy Statement: Your GPS for financial decision-making. Analysis Paralysis: How to keep market fears from freezing your progress. Navigating Political Uncertainty: Keep your portfolio calm, even when headlines aren’t. Spending Smarter: Align your money with what you value most. Gradual Wins: Why slow and steady wins the financial race every time. Bad Decisions: How to recognize when you’re doubling down and when to hit the brakes. 🎧 Ready to make 2025 your best financial year yet? Tune in now to stack smarter, avoid the pitfalls, and get inspired to crush your goals! FULL SHOW NOTES: https://stackingbenjamins.com/stacker-money-mistakes-nyc-1629 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Does finding purpose in life feel overwhelming? What if you didn’t need a “grand” purpose to find meaning? Today, Dr. Jordan Grumet (AKA Doc G) joins us to explore the concept of “little P” purpose—those smaller, everyday moments that bring joy and fulfillment. From Julia Child’s journey to surprising stories of purpose in unexpected places, this episode will inspire you to find meaning right where you are. Here’s what we cover: Little P Purpose: How focusing on smaller, intentional acts can enrich your life. Purpose vs. Meaning: The difference, why it matters, and how it impacts your happiness. Doc G’s Journey: His personal insights on combating purpose anxiety and finding fulfillment. Julia Child and Beyond: Inspiring stories of people who embraced purpose at any stage of life. In headlines, we dive into 2025’s new tax brackets and savings limits—because a purposeful life is even better with a solid financial foundation. And don’t miss Doug’s trivia and some hilarious (and heartwarming) gift stories to round out the episode. Tune in for an uplifting mix of inspiration, financial insights, and a few surprises along the way! FULL SHOW NOTES: https://stackingbenjamins.com Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What if you could spend guilt-free on what you love and keep your finances on track? In this episode, we’re joined by Jen and Jill from the Frugal Friends podcast to break down how to live frugally without crossing the line into being cheap. Frugal living isn’t about deprivation—it’s about prioritizing your spending on what truly lights you up while cutting back on the things that don’t. Jen and Jill share practical strategies to help you: Identify the difference between frugal and cheap decisions. Build a spending plan that aligns with your values and goals. Use budgeting as a tool for joy, not restriction. But that’s not all. We also explore: The hidden dangers of compulsive trading and its growing impact on investors. Doug’s deep dive into his Amazon spending history—prepare for a laugh and a wake-up call. Whether you’re looking to reframe your relationship with money or simply want to enjoy what you love without breaking the bank, this episode is packed with actionable tips to help you crush your financial goals in 2025. Tune in and learn how to master the art of intentional spending! FULL SHOW NOTES: https://stackingbenjamins.com/how-to-shun-consumerism-1627 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What’s the secret to growing your income? In part two of our conversation with business dynamo Alex Hormozi, we explore the mindset shifts, skill-building tactics, and high-impact strategies that can take your earning potential to the next level. Whether you’re an entrepreneur or climbing the corporate ladder, this episode is packed with actionable insights to help you crush your 2025 financial goals. Here’s what we cover: Focusing on what matters: How core activities with high ROI can eliminate unnecessary tasks. Stacking skills strategically: Love what you do? Build on it to stand out and earn more. Taking advice wisely: Only listen to people who actually have what you want. Risk and failure: Why calculated risks and learning from mistakes are non-negotiable for success. Value exchange: The underrated power of bartering, mentorship, and creating systems. Alex also shares how entrepreneurial lessons apply to 9-to-5 jobs, why becoming the go-to person makes you indispensable, and the value of long-term thinking when building teams. Ready to transform your approach to income growth? Tune in and start stacking those Benjamins with bold moves and proven tactics! FULL SHOW NOTES: https://www.stackingbenjamins.com/alex-hormozi-part-2-1626/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What would you do with $100 million a year? Today, we unpack Joe’s insightful conversation with business mogul Alex Hormozi, who breaks down the steps to massively increasing your income. Spoiler alert: It’s not about clipping coupons—it’s about thinking bigger, stacking the right skills, and taking strategic risks. Whether you’re an entrepreneur or rocking it in a 9-to-5, Alex shares: How to identify high-leverage opportunities to grow your income. The art of negotiating for more value, no matter your role. Why maximizing your life is more impactful than endlessly optimizing it. The importance of “10x thinking” and making transformative decisions. How stacking skills can set you apart and skyrocket your earning potential. Get ready to shake up your 2025 game plan and rethink how you approach earning, saving, and living larger. Don’t just settle for incremental improvements—this episode is your guide to big moves. It's time to unlock your potential and build a bigger stack! FULL SHOW NOTES: https://stackingbedndjamins.com/alex-hormozi-part-1-1625 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you go from a struggling actor to the top of the real estate world? Rounding out our greatest hits week of epic shows, we time travel back to when Ryan Serhant, star of Million Dollar Listing New York and the new Netflix series Owning Manhattan, shared his journey from rock bottom to building a billion-dollar real estate empire. In this episode, Ryan reveals how juggling multiple priorities, embracing initiative, and even practicing improv can transform your sales game and your life. But that’s not all! We also dive into using reward points for 529 plans, the risks of banking perks, and how to balance saving for college with planning for retirement. Along the way, we sprinkle in stories, insights, and a little basement-style charm to keep you engaged. Here’s what we cover: Ryan Serhant's pivot from struggling actor to real estate mogul Sales tips, including the art of listening and making friends quickly Why improv can make you a better salesperson Insights from Ryan's new Netflix series, Owning Manhattan Lessons from Tiger Woods and other high performers Reward points and their role in funding 529 plans The potential pitfalls of banking perks Balancing college savings with retirement goals Emergency funds and FAFSA tips Whether you’re looking for career inspiration, financial insights, or a reason to laugh, this episode has you covered. Tune in and stack your knowledge with us! FULL SHOW NOTES: https://www.stackingbenjamins.com/zero-to-million-dollar-listings-ryan-serhant-greatest-hits-week-1624/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What’s the secret to turning small, consistent actions into million-dollar results? Legendary financial educator Paul Merriman joins the basement crew to share his powerful principles for building wealth, including the critical role of diversification and the magic of target date funds. Whether you’re just starting or refining your portfolio, Paul’s advice is packed with actionable strategies to help you reach your financial goals. This episode doesn’t stop there. We tackle the pros and cons of non-traded REITs, decode the SEC’s new push for investor transparency, and dive into an intriguing audience question: is rebalancing your portfolio really necessary? Of course, we sprinkle in some trademark basement banter to keep things lively. Here’s what we cover: Paul Merriman's top wealth-building principles The pros and cons of non-traded REITs How the SEC's new initiative aims to help investors Why diversification is the only free lunch in investing The power of target date funds for long-term success Stocks vs. bonds: finding the right mix for your portfolio Is rebalancing your portfolio necessary? The importance of starting early and staying consistent Whether you’re here for the financial wisdom or the banter from Mom’s basement, this episode will leave you better equipped to make smarter money moves. Let’s get stacking! FULL SHOW NOTES: https://www.stackingbenjamins.com/5-million-dollar-ideas-paul-merriman-greatest-hits-1623/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

For this next installment to this edition of our Greatest Hits Week, we throw it back to a conversation Joe had with Zoe Chance about how to make influence your superpower. Do you ever feel like you just don’t have much influence over others? Not in a negative way, but in a way where you wish people would truly hear you. Sometimes we just need to take a step back and re-evaluate what we are trying to accomplish. Zoe Chance is an expert in influence and is an Assistant Professor at Yale. She joins us today to share her secrets to positive influence and happiness. She talks about the power of ‘no’, charisma, and my favorite, the Kindly Brontosaurus technique. During our headline segment, we dive into longevity in financial planning. As people start living longer, what adjustments need to be made to financial plans? We talk about retirement planning and allocations as it relates to living longer lives. We also help answer Jenna’s question about saving or spending HSA dollars and Doug shares his influential trivia. This episode originally aired on February 23, 2022. Please disregard any mention of current events. FULL SHOW NOTES: https://www.stackingbenjamins.com/make-influence-your-superpower-greatest-hits-week-1622/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How can kindness and a little math transform not just a company but an entire outlook on life? In this episode, we’re joined by James Rhee, who shares his remarkable journey from venture capitalist to CEO of a company dedicated to inclusivity and empowerment for plus-size Black women. James opens up about the values instilled by his Korean immigrant parents, the challenges of reviving a struggling business, and how empathy and cultural understanding can create impactful, lasting change. James also shares his leadership philosophy, emphasizing the power of kindness in decision-making and the surprising role of math in driving meaningful progress. From the red helicopter story to his thoughts on the importance of liberal arts education, James’ perspective is a refreshing reminder that true success starts with leading from the heart. On the financial side, Joe and OG tackle a listener’s question about mortgage recasting, explaining the differences between lowering monthly payments and paying down principal, and why understanding your financial goals is crucial. They also dive into wedding spending trends, including tips for managing costs without sacrificing the celebration. And because it’s the holiday season, the episode wouldn’t be complete without warm, festive stories. Joe and OG reminisce about early Christmas mornings, favorite holiday traditions, and the unexpected joys of giving (and receiving). What You’ll Learn Today: Leadership lessons from James Rhee, including the role of kindness and cultural understanding in personal and professional success. How recasting a mortgage works, when it makes sense, and how to align it with your goals. Practical strategies for managing wedding budgets and navigating the financial burden of attending events. Why intentionality is the key to handling major financial milestones. Episode Highlights: James Rhee’s journey from venture capitalist to CEO and his focus on empowering plus-size Black women. The power of kindness and math in leadership, with personal stories from James’ upbringing and career. Wedding spending trends, budgeting tips, and financial advice for planning big events. Joe and OG’s take on mortgage recasting and how to approach it strategically. Festive Christmas morning memories and holiday traditions. Why You Should Listen: Whether you’re looking for leadership inspiration, practical financial advice, or just a little holiday cheer, this episode has something for everyone. James Rhee’s story will leave you inspired to lead with kindness, while Joe and OG’s financial insights will help you tackle your goals with confidence—and maybe a few laughs along the way. Kindness and intentionality can change your finances—and your life. Tune in to this inspiring episode and make it a holiday season to remember. FULL SHOW NOTES: https://www.stackingbenjamins.com/beyond-the-numbers-james-rhee-success-through-kindness-greatest-hits-1621/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What happens when Doug gets visited by three ghosts in the basement? A classic holiday story gets a Stacking Benjamins twist in this special episode. Inspired by A Christmas Carol, we explore lessons from the past, present, and future to help you make smarter money moves. From learning to avoid past financial missteps to balancing life’s experiences with your financial goals, this episode blends memorable storytelling with practical advice. Along the way, Joe, OG, and Doug serve up clever banter, unexpected insights, and strategies you can put into action to ensure your finances stay merry and bright. What You’ll Learn Today: How reflecting on financial mistakes can help shape smarter decisions. The importance of balancing money with life experiences in the present. Why intentionality and automation are the secret weapons for future financial success. Practical strategies to avoid the consequences of inaction. Episode Highlights: The team kicks off by debating the best versions of A Christmas Carol. Doug’s journey begins with a visit from the Ghost of Christmas Past, offering lessons on overcoming financial missteps. The Ghost of Christmas Present emphasizes being mindful of your current financial habits and enjoying life without overindulgence. The Ghost of Christmas Future shows why planning and automating your finances now can save you from future regret. Practical advice on setting short- and long-term goals, creating financial intentionality, and balancing fun with financial responsibility. Why You Should Listen: If you’ve ever felt haunted by past money decisions, unsure about how to balance saving with spending, or overwhelmed by future financial planning, this episode is for you. It’s a thoughtful, engaging, and surprisingly relatable take on holiday classics—with plenty of tips to ensure your financial wellness story has a happy ending. Gather around, grab some eggnog, and join us for a holiday tale that’ll leave you inspired to tackle your finances with clarity and purpose. FULL SHOW NOTES: https://www.stackingbenjamins.com/doug-and-the-three-ghosts-1620 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

The holiday season is here, and while it’s a time for celebration, it can also throw a curveball at your health and financial goals. In this episode, we’re joined by Angelo Poli from MetPro, who shares his no-nonsense approach to managing holiday indulgences without sacrificing all the progress you’ve made. Think of it as building a resilient portfolio—you can enjoy the party but still limit the downside. From understanding your metabolism to navigating holiday feasts and weight loss medications like Ozempic, Angelo offers practical strategies to keep your health on track while enjoying the season. But we’re not stopping there. We also dive into estate planning essentials, including a cautionary tale about a video will gone wrong (yes, even your estate plan needs a solid foundation). And what’s a holiday episode without some laughs and trivia? We round out the show with listener questions, Nick from the North’s budget dilemma, and a fun discussion about flying around the world. What You’ll Learn Today: Smart strategies for balancing holiday cheer with health goals, including tips for managing alcohol and indulgent foods. How to leverage your metabolism for better weight management. The truth about weight loss medications and their real-life impact. Why estate planning matters more than ever in the digital age—and how to avoid common pitfalls. Practical advice for navigating holiday spending without blowing your budget. Episode Highlights: Reflecting on how fast time flies and gearing up for the holidays. Angelo Poli’s top tips for keeping holiday indulgences in check. Breaking down myths about weight loss medications and the importance of behavior over quick fixes. Estate planning essentials, including lessons from a case where a video will was invalidated. Fun banter, trivia, and Nick from the North’s relatable holiday budget dilemma. Why You Should Listen: This episode is a must for anyone juggling holiday festivities with long-term goals. Whether you’re strategizing for your health, wealth, or estate plan, you’ll find actionable advice wrapped in a festive package. Plus, it’s always good to know how to enjoy the season without feeling like you’ve set yourself back. Take control of your holiday season and start stacking those Benjamins—without sacrificing the things you enjoy most. FULL SHOW NOTES: https://stackingbenjamins.com/balancing-holiday-cheer-with-your-long-term-goals-1619 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

As 2024 winds down, we’re taking a look back at the year that was—its challenges, its surprises, and the financial lessons we’ve all had to learn (sometimes the hard way). Whether you’re strategizing for big goals in 2025, making sense of unpredictable markets, or just trying to stay one step ahead of inflation, this episode has you covered. We’ve assembled a powerhouse panel of financial thinkers—OG, Paula Pant, and Jesse Cramer—to break it all down. Together, they tackle everything from the unpredictable influence of AI on markets and investing to the surprising resilience of real estate in the face of rising interest rates. Plus, they explore the year’s most intriguing (and occasionally jaw-dropping) headlines, like the impact of significant economic shifts and even the infamous United Healthcare CEO murder. Why You’ll Want to Tune In: Discover how 2024’s biggest events, including the AI revolution and shifting inflation trends, impact your wallet. Learn why patience and adaptability are critical tools for navigating market volatility. Get actionable strategies for tackling real-life financial challenges, like managing interest rates and planning for 2025. Episode Highlights: Reflecting on the big financial lessons of 2024: From AI in market behavior to Bitcoin’s latest chapter. How the crypto craze evolved this year—and what it means for the future. The ongoing unpredictability of investing and how to stay grounded. Surprising lessons from corporate America’s headlines, including shocking events like the United Healthcare CEO murder. Inflation, real estate, and housing market realities: What it all means for your plans in 2025. How AI is reshaping everyday life, job markets, and even podcasting. Our Panel’s Key Takeaways: OG shares portfolio management strategies to help you ride out market uncertainty. Paula Pant unpacks real estate trends and the importance of designing a life you love. Jesse Cramer dives into how behavioral finance plays into today’s fast-changing landscape. Looking Ahead: As we close out another exciting year of The Stacking Benjamins Show, we want to thank you, our loyal Stackers, for joining us on this journey. In 2025, we’re bringing even more fresh takes, insightful interviews, and, of course, the best money advice disguised as good conversation. What’s Coming in 2025: We’ll dive into the latest financial trends, explore groundbreaking stories, and keep helping you make smarter money moves while keeping it entertaining. Stick with us as we continue stacking those Benjamins—and maybe even have a little fun along the way. Thank you for being part of the Stacking Benjamins community. Here’s to another year of learning, laughing, and leveling up your financial life! FULL SHOW NOTES: https://stackingbenjamins.com/2024-year-end-review-1618 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Feeling like your wallet’s taking a holiday beating? Don’t sweat it. We’ve got eight clever strategies to keep your spending in check and set yourself up for a financially stronger new year. But wait—there’s more! We uncover the mind-blowing story of a 29-year-old living large in a mansion filled with luxury cars and Elton John's piano. What's his secret? (Hint: It’s not what you’d expect.) And because we love answering Stackers' burning questions, we tackle a double feature: Pensions: Are they still worth the hype? Should you pay off your mortgage before retirement? Sprinkle in some holiday stress hacks, thoughts on budget-friendly gift-giving, and why Tony the Tiger has something to do with the Grinch, and you've got a show packed with financial wisdom you can actually use. Episode Highlights How the Grinch Really Stole Christmas Welcome to the Stacking Benjamins Show Is Your Holiday Budget Already on Thin Ice? 8 Strategies to Tame Holiday Expenses A Mansion, Luxury Cars, and Elton John’s Piano? Handling Holiday Stress Without Losing It Travel Plans & Navigating Holiday Spending How to Leverage Debt (the Smart Way) Get Kids Involved in the Budget—Yes, It’s Possible Starting a 529 Plan? Why Family Might Help Gift Strategies That Won’t Break the Bank Today’s Date in History: Because Why Not? TikTok Minute: The Mansion Story That Broke the Internet Listener Questions: Pensions vs. Mortgages Corrections Dept: Football Teams Need a Map Final Thoughts and Big Takeaways Whether you're taming holiday expenses, dreaming of mansion living, or just trying to get through December with your finances intact, this episode's got something for you. Tune in, take notes, and finish the year strong. FULL SHOW NOTES: https://www.stackingbenjamins.com/sticking-to-your-financial-goals-during-holidays-1617/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like you’re your own worst enemy when it comes to reaching a goal? Today, we sit down with Thais Gibson from the Personal Development School to explore how self-sabotage sneaks into our lives and—more importantly—how to kick it out for good. While you've maybe heard Thais on Mel Robbins or other shows, what you haven't heard is what we talk about today - how specifically she walks Joe through limiting beliefs and then outlines how it's done. Whether you've followed Thais' huge social media presence consistently or it's your first time with her, we know this will help you kick self-sabotage to the curb and get to work. From aligning your conscious and subconscious goals to overcoming limiting beliefs, this conversation is packed with actionable insights to help you get out of your own way. But that’s not all. We also dive into a financial hot topic: influencer-backed crypto scams. Learn how a viral coin duped investors last week and why speculation isn’t the same as smart investing. Of course, it wouldn’t be a Stacking Benjamins episode without some holiday flair. Joe, OG, and Doug share festive mall memories, debate the best holiday tunes, and throw in some trivia to keep things lively. Why You’ll Love This Episode: Practical tips to recognize and overcome self-sabotage. Eye-opening lessons on speculative investments and influencer-driven hype. A nostalgic take on holiday mall culture. Remember that? Episode Highlights: Kicking off with holiday concerns and a satirical take on seasonal trends. Festive mall memories: shopping chaos, holiday tunes, and the art of people-watching. Thais Gibson’s insights on aligning conscious and subconscious goals to beat self-sabotage. Turning resistance into opportunities and tackling the emotional costs of inaction. Practical steps to rewire limiting beliefs and visualize success. Lessons from a viral influencer’s crypto scam and the dangers of speculative investing. Speculation vs. investing: Why it matters and how to avoid costly mistakes. Holiday trivia fun and laughs with the Basement crew. What You’ll Take Away: Whether you’re looking to improve your mindset, steer clear of financial pitfalls, or just enjoy some holiday tunes, this episode offers a little something for everyone. Walk away with tools to set yourself up for success—mentally, financially, and maybe even musically (if Doug’s favorite holiday tune is your jam). Keep the Conversation Going: Have a story of self-sabotage you’ve overcome or a holiday memory to share? Join us in the Basement Facebook group to swap tips, laughs, and maybe a little holiday cheer. FULL SHOW NOTES: https://www.stackingbenjamins.com/stop-self-sabotaging-thais-gibson-1616 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If your bank account is thriving, but your soul feels bankrupt, are you really living your best life? Today we dive into the deep end of personal finance, tackling life's biggest questions. The discussion starts with festive neighborly rivalries (think over-the-top decorations and holiday antics) but transitions pretty quickly into an emotional exploration inspired by a powerful piece written by Jonathan Clements for his Humble Dollar blog. Reflecting on his cancer diagnosis and thoughts on mortality, Clements’ writing serves as a springboard for a candid roundtable chat about regrets, risk, and how to make the most of our limited time. With additional insights from Paula Pant and Doc G, this episode is all about helping you live purposefully while keeping your financial house in order. Why You’ll Love This Episode: Explore how to balance financial strategies with meaningful life choices. Gain perspective on managing regrets and making peace with life’s uncertainties. Discover why generosity and appreciating the little things are the ultimate forms of wealth. Episode Highlights: Holiday hilarity: Over-the-top decorations, fish sticks, and birthday antics. Jonathan Clements’ reflections on mortality and embracing the present moment. Paula Pant and Doc G’s insights on purposeful living and financial balance. Strategies for managing risk, reward, and estate planning challenges. The transformative power of generosity and savoring simple joys. Trivia Fun: It’s the final trivia showdown of the year! Can OG claim victory, or will this be another epic trivia blunder? Tune in for the the guesses, and a few surprising facts. Takeaways to Ponder: Jonathan Clements’ reflections remind us that while building wealth is essential, so is living a life filled with purpose, generosity, and connection. Resources Mentioned: Jonathan Clements’ Humble Dollar Blog Post: The C Word Stacking Benjamins Book Club is Open! Join the Basement Facebook Group Let’s Keep the Conversation Going: What’s your secret to balancing finances with a life well-lived? Share your thoughts with us in the Basement Facebook group, or tag us on social media. Learn more about your ad choices. Visit podcastchoices.com/adchoices

It’s a Festivus for the rest of us! This week, we’re mixing holiday cheer with must-know insights to keep your season merry, bright, and worry-free. Steve Kerber joins us from the Fire Safety Research Institute, who shares life-saving fire safety tips just in time for all those twinkling lights and candles. Because the best insurance is prevention, right? This year we're chatting about lithium-ion batteries and how explosive (literally) these can be for your holiday season if you aren't careful. We'll also chat about smoke alarms, closing your doors, and having an emergency exit plan in place! But that’s not all—we’re also diving into why big Wall Street players are taking out loans they don’t need and how you can apply creative financing strategies to your own life. Plus, we answer a listener’s estate planning question that came up during their bedtime reading (we love multitasking). Sprinkle in some holiday trivia, debates over the best Christmas movies, and discussions on revocable trusts, and you’ve got a variety-packed episode that’s as fun as it is informative. Episode Highlights: Holiday fire safety tips from Steve Kerber, including new standards for smoke alarms and tips for handling lithium battery hazards. Why having a solid fire escape plan is the ultimate prevention strategy. How Wall Street’s creative financing trends can inspire you to rethink debt and financial flexibility. Strategies for analyzing and managing debt like a CFO, just in time for the New Year. Listener Q&A on estate planning, with practical advice on revocable trusts and holistic financial planning. Holiday trivia, featuring quirky debates about the best Christmas movies—spoiler alert: “Die Hard” might come up. Why You’ll Love This Episode: It’s not every day you get a mix of life-saving fire tips, actionable financial strategies, and festive fun in one show. Whether you’re looking to keep your home safe, optimize your finances, or just get a good laugh, this episode has something for everyone. Resource Mentioned: BatteryFireSafety.org FULL SHOW NOTES: https://stackingbenjamins.com/fire-safety-tips-2024-steve-kerber-1614 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Don’t Forget: Tell us your favorite holiday movie! Share your pick in the Basement Facebook group or tag us on social media. Who knows—you might just settle the debate once and for all. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Do you dream of conquering your financial goals and achieving true financial independence? In this episode, we’re diving into five BIG mistakes people make along the way to financial glory with money coach Bernadette Joy, who paid off a staggering $300,000 in debt and locked in a work-optional life by age 40. Along the way, we’ll explore the importance of managing your budget during the notoriously tricky holiday season, share actionable strategies to curate your accounts, and highlight the common mistakes that can derail even the best-laid financial plans. You’ll also hear the wild story of Richard Whitaker, whose pursuit of a too-good-to-be-true 15.25% return serves as a cautionary tale for us all. Whether you’re looking to tackle debt, sharpen your budget, or avoid financial scams, this episode is packed with insights to help you stack smarter. Episode Highlights Kicking off with weekend escapes, Monday blues, and a salute to the armed forces Nostalgic nods to Chitty Chitty Bang Bang Welcoming Bernadette Joy and diving into her inspiring journey to financial freedom Sharing personal stories and struggles that resonate with every money nerd Breaking through financial barriers on the path to independence Setting financial goals with inspiration from meeting Simone Biles Why comparing success stories can derail your progress The delicate dance between frugality and societal expectations Staying grounded amidst the curated realities of social media Avoiding the common mistake of giving unasked discounts Why accepting debt as a long-term lifestyle is a trap Choosing financial freedom over fear and hesitation The importance of diverse perspectives in your financial advisory team Preparing for the unexpected: Life events that test your financial foundation Exploring and questioning investment opportunities like Yield Wealth Understanding the gambler’s mentality and how it can lead to downfall Practicing due diligence to avoid falling for scams Lessons learned from the downfall of Yield Wealth and how to protect yourself Announcements about upcoming events and opportunities to connect This episode is a mix of relatable stories, practical advice, and lessons learned the hard way. Tune in to start crushing your money goals and avoiding financial pitfalls—one smart decision at a time. FULL SHOW NOTES: https://www.stackingbenjamins.com/crush-your-2025-money-goals-bernadette-joy-1613 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you still haunted by that Cleveland Browns jersey you never asked for? Or maybe you're on the hunt for the perfect gift for the money nerd in your life? Fear not! Joe, OG, Doug, Mindy Jensen (from BiggerPockets Money), and Jesse Cramer (from Best Interest) are here to save the day with a sleigh-full of gift ideas that won’t end up in next year’s white elephant exchange. This episode is stuffed with creative ideas, from meaningful experiences and insightful book recommendations to practical subscriptions and quirky mugs that’ll light up the eyes of any financially savvy friend. As the holiday banter flows, OG takes the trivia crown, and Mindy and Jesse share stories, laughs, and plenty of cheerful banter. Whether you're buying for your favorite money nerd—or looking for ideas to add to your own wishlist—this episode is your guide to holiday shopping success. Episode Highlights Festive introductions and holiday banter Special broadcast from YouTube HQ: The Stacking Benjamins Show goes live! Exploring financial independence and how it shapes gift-giving Meet the guests: Mindy Jensen and Jesse Kramer join the basement party Gifts for money nerds: From the practical to the quirky The great debate: Experiences vs. material gifts Financial board games that teach (and entertain!) Trivia time: Holiday and Rudolph the Red-Nosed Reindeer fun Uncovering the story behind Rudolph’s red nose Gift ideas galore: Books, subscriptions, and unique finds for the finance-minded Farewells and podcast highlights to brighten your season From laughs to lightbulb moments, this episode is packed with inspiration to make your holiday gift-giving easier—and way more fun. Tune in and start stacking those holiday wins!🎁🎄 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you ready for a shake-up in the world of financial planning? This week, we’re diving into Robinhood’s bold leap into financial advising and what it could mean for the industry—and for you. We’ll cover navigating market volatility, how AI is reshaping personal finance, and why index funds remain a top choice for long-term goals. Plus, Doug’s latest escapade leads us to some unexpected places, including a yacht adventure and the art world’s million-dollar banana. Episode Highlights Introduction and Doug’s latest antics Robinhood’s big move into financial planning Practical tips for navigating today’s volatile market Why index funds might still reign supreme for long-term investors The pros and cons of RIAs (Registered Investment Advisors) and custodial platforms Financial planning strategies for young investors starting out Emerging trends shaping the financial planning landscape Smart debt management strategies to keep you ahead Highlights from past episodes that you’ll want to revisit Doug’s TikTok Minute: Yacht adventures and high-seas drama Trivia Time: The Great Smog of London and what it teaches us about resilience Listener Q&A: How to project portfolio growth without losing your cool The wildest story of the week: The art world’s million-dollar banana From the latest in financial trends to practical strategies, this episode is packed with insights to help you take your financial planning to the next level. Tune in and start stacking smarter! Links to Check Out Show Notes & Resources: Get the full scoop at StackingBenjamins.com Retiremeet 2025: Joe is taking the stage on February 8, 2025! Grab your ticket at Retiremeet.com and use code STACKING for a discount! New York City Meetup: Join us for a fun-filled evening on December 12! Details at StackingBenjamins.com/NYC Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you ready to take control of your finances and make this holiday season the year you avoid debt traps? Today, we're diving into the inspiring story of Jackie Cummings Koski, co-host of the Catching Up to FI podcast. Jackie’s journey—from a divorce that sparked her financial awakening to achieving FIRE (Financial Independence, Retire Early)—is packed with lessons you can use to stack your Benjamins and live life on your terms. What You’ll Learn Today: How to develop a saving habit that lasts. The key steps Jackie took to overcome financial fears and invest wisely. Tips for navigating holiday spending without breaking the bank. Jackie also shares actionable strategies for building a financial dashboard, exploring side hustles, and embracing flexibility in your work and life. Whether you're just starting or looking to fine-tune your financial game, this episode is packed with advice to help you move forward with confidence. Episode Highlights: Struggling to get back to work after a holiday weekend? We’ve all been there! Jackie’s journey: From financial wake-up call to achieving FIRE success. Overcoming fears, gaining confidence, and investing smarter. Building a financial dashboard to track your progress. Smart holiday spending tips to keep your budget intact. Trivia Fun: How much do people typically overspend during the holidays? Join Joe, OG, and Doug as they tackle this question in our trivia segment, with plenty of laughs and surprises along the way. Don’t Miss This Episode If: You’re looking for inspiration, actionable advice, and practical tips to master your money, avoid holiday debt, and build the financial independence you’ve always dreamed of. Resources from This Episode: Jackie Cummings Koski’s Catching Up to FI Podcast Stacking Benjamins Workplace Benefits Guide Join the Basement Facebook Group for Tips and Community Fun Love What You Hear? Share the Wealth! If today’s episode inspired you, help us spread the word by leaving a review or sharing it with a friend. Every share helps keep the basement buzz going! FULL SHOW NOTES: https://stackingbenjamins.com/FIRE-basics-with-jackie-cummings-koski-1610 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

In our most EPIC board game episode EVER, Joe is joined by board game aficionados Katie, Sean, and Daniel. The four of them dive into the world of board games—just in time for holiday gatherings! Whether you're hosting family, looking for a budget-friendly gift idea, or just want to create memorable moments, this panel has you covered. The create two lists on today's show. The first includes their top 5 games with a money or economic component. From games about running economies, to running businesses, to buying real estate and more, the team comes through with some great recommendations, just in time for the holidays (check out our show notes for links to purchase any of the listed games!). The second list helps ensure you don't waste money this holiday season on games that stink! If you're playing games this holiday season with friends and family, our panel lists off their top 5 games that you can find reliably in the Target or Walmart game aisle, your friendly local game store, or online. You're sure to find something you love on these lists. (Again, you can help the show AND enjoy your holiday season by purchasing from our show notes page!). Overall, they share their top picks, including timeless classics and modern favorites, guaranteed to spark fun and foster connections. Along the way, the crew chats about the lessons these games can teach—strategy, teamwork, and maybe even a little patience when Uncle Doug gets competitive. Speaking of Doug, he’s back with a trivia segment on the popular game Carcassonne and its iconic wooden game pieces, the 'Meeples.' If you’re looking to level up your family game nights or find the perfect holiday game, this episode is a jackpot! Episode Highlights Introduction and Black Friday Buzz – How board games fit into your budget-friendly shopping plans. Meet the Panel – Katie, Sean, and Daniel share their board game obsessions and how they got started. Top Picks from the Experts – From Katie’s family-friendly favorites to Sean’s fast-paced picks and Daniel’s strategic challenges. Spotlight on Unique Games – Explore gems like The Zen of Takeo, Mr. President, and Juicy Fruits. Holiday Recommendations – Perfect games for all ages, from casual party players to strategy enthusiasts. Deep Dive on Popular Games – Learn about strategies for Catan, the charm of Ticket to Ride, and the quick thrills of Five Minute Marvel. Trivia Fun with Doug – A game within the episode! Can you guess the answer to Doug’s Carcassonne trivia? A Few of Our Panelists' Top Picks Katie’s Favorites: Phase 10, Ticket to Ride, and more. Sean’s Must-Haves: Azul and Five Minute Marvel. Daniel’s Top Choices: Fishbowl, The Crew, and Cinco Lingo. Whether you’re a seasoned gamer or a newbie looking to try something fun, this episode is packed with tips, laughs, and plenty of game ideas to keep your holidays entertaining and affordable. Got a favorite board game? Share it with us on social or call in—we’d love to hear your recommendations! FULL SHOW NOTES: https://stackingbenjamins.com/board-game-extravaganza-2024-1609 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ready to brave the Black Friday madness? Don’t hit “add to cart” just yet! In this episode, tech guru Bridget Carey from CNET joins us to share her insider tips on navigating the sea of deals and avoiding those flashy-but-fishy doorbusters. Whether you’re hunting for the latest gadgets or trying to resist that smart fridge you probably don’t need, Bridget’s advice will save your wallet (and maybe your sanity). But that’s not all! We’re diving into why mortgage rates are still climbing even as the Fed cuts interest rates, what it means for your financial plans, and whether paying off your mortgage early is worth the hype. Along the way, we sprinkle in personalized money moves, tech nostalgia, and even some surprising theme park innovations (hint: the future is now, and it’s a little quirky). It’s an episode jam-packed with expert advice, a few detours into saxophone mysteries, and practical tips to keep your finances (and holiday shopping) in check. Run of Show Black Friday Tech Talk: Introduction and Welcome Thanksgiving Prep and Family Traditions (a.k.a. Stuffing Debate #4,567) Tech Gadgets You Want vs. Gadgets You Actually Need Bridget Carey’s Tech Wishlist and Recommendations AI in Everyday Tech: The Good, the Bad, and the Overhyped Apple Products and Innovations: Must-Have or Meh? Fun and Quirky Tech Toys to Impress Your Inner Child Theme Park Tech Updates: The Future of Fun Star-Studded Party Details: Who Brought the Mystery Saxophone Player? Mortgage Rates and Why the Math Isn’t Mathing Homeowner Strategies: To Pay Off or Not to Pay Off? TikTok Tips for Saving More This Holiday Season Upcoming NYC Meetup and Thanksgiving Wishes from the Basement Crew Movie Review: Conclave – Worth Your Time or Skip It? FULL SHOW NOTES: https://stackingbenjamins.com/best-tech-deals-2024-1608 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ah, the holidays—a time for twinkling lights, warm cocoa, and the yearly hunt for the perfect Black Friday deal. Feeling the mix of cheer and budget-related stress? Don’t worry, we’ve got you covered! Today, Regina Conway from SlickDeals joins us to share insider tips on scoring the best bargains. From stacking deals for maximum savings to finding hidden gems (like book bargains that’ll thrill even non-readers), Regina has the scoop to help you stretch every dollar this season. But we’re not stopping at shopping—oh no. We’re tackling the lesser-known world of using your IRA to invest in real estate. Spoiler alert: it’s not as simple as it sounds. We’ll break down the rules, avoidable mistakes, and real estate horror stories that’ll make you think twice before jumping in. And because it’s the holidays, we’re sprinkling in a little fun. Think debates over Mariah Carey’s playlist dominance, nostalgic Christmas traditions, and some lighthearted banter that’s as comforting as Grandma’s stuffing (though maybe less calorie-dense). Cheers to smarter shopping and investing that doesn’t leave you out in the cold! Run of Show Thanksgiving Banter and Warm Holiday Wishes Saluting the Troops and Sharing Gratitude Black Friday Buzz: Meet Regina Conway from Slick Deals Spotlight on Real Estate Investor Horror Stories Holiday Traditions: From Playlists to Tech Talk Slick Deals’ Top Black Friday Shopping Tips Book Deals and the Unexpected Rise of Reading Travel Deals and Gift Cards That Pack a Punch Memberships, Subscriptions, and Tickets: Hidden Savings Utility Items and Home Improvement Must-Haves The Slick Deals Community: Smart Shoppers Unite How Slick Deals Makes Money (and Keeps the Lights On) Celebrating 25 Years of Slick Deals Historical Trivia: The Origin of Coupons Essential Holiday Shopping Tips for the Savvy Stacker Using Your IRA for Real Estate: The Dos and Don’ts Monthly Update on the Benefits Guide Holiday Season Reflections and Final Thoughts FULL SHOW NOTES: https://stackingbenjamins.com/black-friday-deals-2024-1607 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like life is one long, chaotic to-do list? Maybe it’s time to grab the reins and start living with intention. In today’s episode, Joe Saul-Sehy, Paula Pant, and Doc G team up with special guest Candy Valentino to help you cut through the noise, focus on what matters, and make purposeful choices that align with your goals. We’ll explore the power of saying “no” (because sometimes your calendar deserves a break), the magic of setting three non-negotiables, and how small, thoughtful shifts can lead to massive wins. Whether you’re a business owner plotting your empire or a 9-to-5er trying to reclaim your time, this episode offers practical tips to help you design the life you want. And just when you thought it was all deep thoughts and purpose, we take a detour to discuss Blackbeard’s treasure (yes, that Blackbeard) and debate its true value. Spoiler alert: The answer might surprise you—or at least make you re-evaluate your treasure-hunting strategy. Grab a seat, Stackers—it’s time to get intentional. Run of Show Opening Scene: Can You Fly This Plane? Welcome to the Stacking Benjamins Show Getting Intentional About Your Life Meet the Guests: Candy Valentino Joins the Crew Candy on The 9% Edge Why Intentional Living is Your Secret Weapon Trivia Time: Digging Into Blackbeard’s Treasure Debating the Value of Pirate Booty The Final Answer Revealed: Was It Worth It? Deep Dive: Intentionality and Finding Purpose Setting Intentions and Dodging Distractions How Small Shifts Can Spark Big Changes Learning to Say No Without Guilt Podcast Highlights and Wrap-Up FULL SHOW NOTES: https://stackingbenjamins.com/all-about-intentional-living-1606 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wondered how to steer clear of trouble with your investments? Today, we’re diving into an SEC investigation that’s rattling one fund and discussing what you need to know to protect yourself. We’re also unpacking the benefits of passive investing and index funds—because simplifying your approach to the stock market might just be the smartest move you make. In our TikTok Minute, we’ll take a look at a quick clip that highlights a common financial misunderstanding, and along the way, we’ll sprinkle in a bit of British charm (no spoilers, but it’s classic). Finally, we’re tackling a listener question from a soon-to-be parent who’s wondering how to plan for their child’s financial future. From custodial accounts to financial aid strategies, we’ll walk through the best options to ensure your kids have a strong start. Add in Doug’s trivia, some thought-provoking discussions, and a peek at upcoming events, and you’ve got a packed episode full of actionable insights. Run of Show Introduction and Opening Remarks Kickoff and Today’s Topics Overview Discussion on the SEC Investigation and What You Need to Know Monitoring Your Money Effectively Sponsor Messages and Lighthearted Banter Headline: Western Assets Bond Fund in Trouble Debating Active vs. Passive Management TikTok Minute: A Quick Look at Financial Missteps Listener Call and Doug’s Trivia Break Listener Question: Financial Planning for a Newborn Custodial Accounts vs. Other Savings Options Tax Implications and Financial Aid Considerations Upcoming Events and Community Meetups Doug’s TV Show Reviews  FULL SHOW NOTES: https://stackingbenjamins.com/when-good-funds-go-bad-1605 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like life keeps throwing curveballs your way? The truth is, it doesn’t actually get easier—you just get better at hitting those pitches. This week, we’re tackling financial challenges head-on with financial behavior psychologist Dr. Brad Klontz and TikTok star Adrian Brambila. Together, they deliver some much-needed “virtual slaps” to help shift your financial mindset from poor to rich. We’re diving into practical tips like automating your finances, avoiding debt traps, and embracing tough love to overcome obstacles. In our headline segment, we’re revealing the U.S. cities with the highest and lowest non-mortgage debt. More importantly, we’ll discuss how to manage your financial health no matter where you live. It’s all about learning to play the game the right way. And, of course, stick around for Doug’s trivia, humor, and possibly a questionable bread recommendation. Run of Show Monday Morning Toast Ritual Debate Over the Best Bread Choices Salute to the Troops Introduction to the Stacking Benjamins Show Meet the Monday Mentors: Brad Klontz and Adrian Brambila Brad and Adrian Share Harsh Truths About Wealth Building The Psychology of Wealth and Financial Mindset Shifts Automation: The Secret Hack to Building Wealth The Poor vs. Rich Mindset: How to Change the Way You Think Investing Wisely: The 4% Rule Book Promotions and Special Offers from the Guests Doug’s Trivia and Humor Break Coaching and Motivational Strategies to Stay on Track Headline Segment: Debt in American Cities (Highest and Lowest) Conclusion and Final Thoughts on Getting Better, Not Easier FULL SHOW NOTES: https://stackingbenjamins.com/tough-love-money-lessons-brad-klontz-1604 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How many personal finance rules does it actually take to keep your financial house in order? Book after book, podcast after podcast—everyone seems to have "the" set of rules you need. But one intrepid blogger asked himself, "How much do I really need to know to keep my financial health on track?" Today, we dive into his answer: the four laws of financial health, as explored by our lively roundtable crew. Joining Joe and OG are Paula Pant, who's made it her mission to Afford Anything, and Jesse Cramer from The Best Interest podcast. OG’s here with a sports injury story (with a twist!), Paula’s got thoughts on ramping up savings, and Jesse dives deep into the need for a solid safety net. Get ready for laughs, valuable insights, and practical tips to help you set, track, and knock out your financial goals with confidence. Plus, we’re treating you to some of Doug’s legendary trivia, and revisiting Oprah’s unforgettable weight loss reveal moment. Buckle up for a mix of fun and insight straight from Mom's basement! Run of Show Introduction and Opening Remarks Meet the Hosts and Guests OG's Sports Injury Story (with a twist) Paula’s Early Voting Adventure Diving into the Four Laws of Financial Health Trivia Time with Doug Oprah’s Weight Loss Reveal: Guessing Game Different Theories on Oprah’s Weight Loss Answer Reveal and Lessons Learned Importance of Cash Reserves Building and Maintaining an Emergency Fund Systematic Saving and Investing Strategies Weekend Plans and Podcast Updates Closing Remarks and Takeaways  FULL SHOW NOTES: https://stackingbenjamins.com/the-four-laws-of-financial-health-1603 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Curious about how AI might sneak its way into your financial plan? Today, we bring you the latest scoop on this hot topic with our guest, Robert Farrington from The College Investor. Together, we’ll break down the research on AI’s potential impact on your financial life (spoiler: it’s not here to pay your credit card bills). Plus, we tackle a listener question from someone who might've spent a bit too much time binging Better Call Saul. Get ready to have your assumptions challenged as we throw in a TikTok Minute that’ll shake up everything you thought you knew abouthuge companies and their projections of the future. It isn't that we don't believe Goldman Sachs...it's just that the cost of being wrong may outweigh the gains of ignoring the strategy altogether. And, of course, stick around for trivia that’ll make you the star of your next gathering—Mom says you should be prepared to impress! Join hosts Joe Saul-Sehy, OG, and the always-insightful Robert Farrington for an episode packed with practical financial wisdom, a few chuckles, and as always, a lot of basement charm. You know...because we're charming. We're coming to NYC on December 12th! Join Joe, OG, Paula Pant AND Doc G for an amazing gathering of personal finance fans. Head to https://stackingbenjamins.com/nyc to sign up before spots are gone. Run of Show Introduction and Opening Remarks Welcoming Robert Farrington Casual Banter and Health Tips Deep Dive into AI and Finance AI in Everyday Life and Financial Planning Challenges and Limitations of AI Using AI for Specific Financial Tasks The Future of AI in Financial Planning Personalized Advice and Experience Asking the Right Questions (to AI and yourself!) Where to Find More Information AI in Personal Finance Trivia Time with Doug Investment Strategies and Market Predictions Upcoming Events and Announcements - We're coming to NYC! Halloween Fun and Candy Tax Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever thought about the intersection of health and wealth? Today we start by sharing personal anecdotes about an unexpectedly painful break, leading into a robust chat with mentor Alua Arthur, a death doula who helps people find purpose through preparing for the end of life. The conversation dives deep into practical tips about setting financial goals while staying grounded, and the importance of balancing spending with saving, all while holding onto life’s deeper purposes. Al Pacino's financial mishaps also serve as a cautionary tale about the importance of being an active CEO of your personal finances. The episode wraps up with advice on navigating the future as veterans from OG, insights into helping children understand finances, and more. You may go look for community, but there is only one that leaves you feeling satisfied: Stacking Benjamins.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today, we'll dive into navigating life's awkward money moments with a fantastic round table discussion. We'll cover topics like how to handle unexpected spills at a friend's house, splitting the bill during social outings, contributing to group expenses, and even first-date etiquette. Plus, we discuss how to wisely use a financial windfall, the benefits of maximizing your retirement contributions, and the potential pitfalls of paying off your mortgage early. Get ready for practical advice, insightful stories, and plenty of laughs as we tackle these everyday financial dilemmas. Introduction and Joe's Favorite Things Upcoming Episodes and Special Guests Guide to Workplace Benefits Sponsors and Show Kickoff Round Table Discussion: Awkward Money Situations Handling the Check: Etiquette and Stories Birthday Dinners and Social Norms First Dates and Financial Expectations Road Trips and Gas Money Guessing the 1933 Minimum Wage Trivia Results and Reactions Listener Question: What to Do with Extra Money? Panel's Personal Updates and Announcements Post-Show Banter and Fun Learn more about your ad choices. Visit podcastchoices.com/adchoices

You asked for details on Joe's son's real estate adventure, and today you get it! This episode takes you to CampFI Midwest, where Joe's 29-year-old son, Nick, shares his journey toward financial independence through real estate investment. Starting in 2020, Nick began buying and renovating properties, primarily in Detroit, while living in Seattle and working at Microsoft. Learn about his strategies, the challenges he faces, and the importance of diversification in building a solid financial plan. The episode includes insights on finding deals, managing properties remotely, and the significance of making and learning from mistakes in the path to financial independence. Introduction to Greatest Hits Week Introducing Camp FI and Nick's Journey Nick's Real Estate Empire The Stacking Benjamins Podcast Vibe Nick's Detroit Real Estate Adventures Nick's Real Estate Strategy and Challenges The Importance of Diversification Concluding Thoughts and Advice Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today, we look at the other side of financial independence: being able to travel the world! Our new Stacking Adventures show is off the ground, and we're giving you a peek at the latest episode. This show highlights YOUR experiences traveling, and when it comes to Japan, you share the best, worst, and in-between. From puking in your bosses' wife's shoes to riding the bullet train, we hear stories from Adventurers and share our own comments. You'll hear tips on packing, organizing luggage storage, theme parks to attend, places to find good food, navigating transportation, and more. You'll find more episodes wherever you're listening to Stacking Benjamins, OR you'll find blog posts, trip reports, packing lists, and more at StackingAdventures.com. Do you have travel stories about Peru, Chile, ghost tours, or New Orleans? Share those stories at StackingAdventures.com/MyStory Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today, we'll discuss the pitfalls of overly conservative retirement planning and how it could delay your financial independence and retirement dreams. In this show which was originally aired on our "brother" show Earn & Invest, Doc G, and guest Jesse Cramer from the Best Interest podcast delve into the importance of finding a balance, exploring the impacts of stacking conservative assumptions related to social security, investment returns, and inflation. Jesse shares practical tips on re-evaluating your retirement assumptions, emphasizing the significance of flexibility and ongoing adjustments to avoid unnecessarily prolonging your work life. RUN OF SHOW Introduction and Topic Overview The Cost of Being Too Conservative Interview with Jordan Grumet and Jesse Kramer Workplace Benefits Guide Announcement Earn and Invest Podcast Begins Jesse Kramer's Background and Career Shift Conservative Assumptions in Retirement Planning Introduction to Conservative Retirement Assumptions Guest Introduction: Jesse Cramer The Impact of Conservative Assumptions on Retirement Strategies to Avoid Overly Conservative Assumptions Revisiting and Adjusting Retirement Plans The 4% Rule and Its Implications Balancing Conservatism and Aggressiveness in Retirement Planning The Consequences of Overly Conservative Planning Practical Tips for Retirement Planning Exploring the 'Die With Zero' Philosophy Dealing with Loss Aversion Anxiety Conclusion and Final Thoughts Post-Interview Discussion Learn more about your ad choices. Visit podcastchoices.com/adchoices

To kick off a contentious week for the USA, we share one of our FAVORITE stories about the thread that binds us, our goals, our dreams, and yes, even our money. Laura Schroff was a high-powered executive in Manhattan when her life was changed forever by an 11-year old boy. It's a story you won't soon forget. Plus, we're thrilled that Scott Trench, BiggerPockets CEO joins us as guest co-host. We talk about crypto, athletes, and their money. It's our favorite way to discuss how your own money decisions could be better made. We also dive into non-compete contracts. That world has been changing quickly, and we've got you covered. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever felt overwhelmed by your finances? Do you find yourself either making purchases as "retail therapy" or avoiding looking at your statements and online accounts? Or maybe, on the other end of the spectrum, you find yourself hoarding cash because you don't know when the next "rainy day" is going to arrive? In all of these cases and more, you might be experiencing financial trauma, a topic that is the focus of today's Stacking Benjamins live round table at FinCon 2024 in Atlanta, Georgia. Hosted by Joe Saul-Sehy and featuring licensed family and marriage therapist Wendy Wright, certified financial planner Lawrence Sprung, and Afford Anything's Paula Pant, the discussion dives into the deep-seated emotional aspects of money. You'll learn about the signs of financial trauma, such as neglecting finances, overspending, and hoarding, and how these behaviors can impact your life. The panel offers insights into addressing and overcoming these issues, emphasizing the importance of compassionate curiosity and seeking professional help when needed. Whether you're living paycheck to paycheck or have a significant net worth, this episode will guide you on the path to better financial health and well-being. RUN OF SHOW Opening Banter and Introduction Live from FinCon 2024 Meet the Panelists Diving into Financial Trauma Signs of Financial Trauma Scarcity Mindset and Personal Stories Cultural and Individual Financial Trauma Judgment and Financial Secrecy Inherited Wealth and Emotional Struggles Behavioral Finance in Financial Planning Building Compassionate Financial Relationships Recognizing Financial Trauma: Hoarding Societal Views on Hoarding vs. Saving Personal Stories of Financial Extremes Balancing Financial Planning and Living in the Present Diagnosing Money Hoarding and Anxiety Steps to Address Financial Anxiety Exploring False Connections with Money The Importance of Financial Planning and Adjustments Tracking Spending and Financial Awareness Principles of Financial Therapy When to Seek Financial Therapy Conclusion and Resources FULL SHOW NOTES: https://stackingbenjamins.com/overcoming-financial-trauma-1595 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today, we're joined by funeral director Scott Mueller, who shares invaluable advice on pre-planning your final expenses. Scott elucidates on the importance of making arrangements ahead of time and the benefits it brings to both you and your loved ones during emotionally charged times. Avoid common pitfalls and choose wisely to avoid turning your financial planning into a horror show. Trick or treat? More like protect your assets or weep! In our headline segment, we delve into optimizing your homeowner's insurance with critical features like replacement cost coverage, special personal property endorsements, and umbrella policies. Discover how these essential elements can guard your castle and your treasures from life's unexpected frights. Finally, we lighten the mood with Doug's hilarious trivia and some fun Halloween anecdotes, ensuring you end this episode both smarter and happily haunted. RUN OF SHOW Introduction to the Witching Hour Halloween Special: Stacking Benjamin Show Meet the Funeral Director: Scott Mueller The Importance of Pre-Planning Funeral Expenses Personal Stories and the Emotional Impact Trust Issues with Funeral Directors Avoiding Funeral Scams and Making Informed Decisions Pre-Planning: Burial, Cremation, and Other Options Final Thoughts and Resources Iconic Horror Movie Lines Halloween Trivia and Chat GPT Funeral Planning Stories Umbrella Liability Insurance Halloween's BEST Jokes and Wrap-Up FULL SHOW NOTES: https://stackingbenjamins.com/final-expenses-planning-with-scott-mueller-1594 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today, we'll dive into an exciting financial education idea brought to us by award-winning columnist and host of The Money Life Show, Chuck Jaffe. Do you think Halloween's kinda boring for kids and just a sugar rush? Not at Chuck's house! Discover Chuck's innovative 'cash or candy' concept, transforming Halloween into a fun and educational game that teaches kids about probability, risk management, and decision-making. This unique approach blends Halloween fun with critical financial lessons, making it a memorable learning experience for children and parents. In our headline segment, we explore some chilling retirement regrets shared in a compelling Business Insider article, highlighting common pitfalls and how to avoid them. We also discuss key strategies for better retirement planning, such as potentially delaying social security and being prepared for unforeseen emergencies. If you're worried about not having enough for financial independence, this may be the segment for you. Lastly, we wrap up the episode with Doug's intriguing Halloween-themed trivia and a lively discussion about the NFL's global expansion efforts, including a look at watching football games in Germany. Join us for a fun and educational journey into the world of Halloween-fueled financial literacy! RUN OF SHOW Halloween Costumes and Banter Salute to the Troops and Halloween Plans Halloween Week Episode Introduction Halloween and Money Lessons with Chuck Jaffe Halloween Games and Economic Lessons Chuck Jaffe's Halloween Tradition Money Life Show and Financial Insights Disturbing Ways to Make Money Trivia Question: a Murderer's Profession Pineapple Drinks Headline: Retirement Regrets Discussion on Retirement Savings Client's Early Retirement Story Janice's Regrets and Future Plans Automating Savings and Easy Listening Community Engagement and Reviews NFL's International Games Fun with German NFL Commentary Christmas Movie Horror Parody FULL SHOW NOTES: https://stackingbenjamins.com/halloween-money-lessons-with-chuck-jaffe-1593 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you on the same page with your significant other? Financially speaking, of course! Given that money is the leading cause of divorce in the US, it's a topic worth working on together. And money talks in relationships don't just apply to romantic relationships - it can extend to include parent/child, etc. relationships. We're talking money and relationships on today's roundtable. Pull up a chair with Paula Pant from Afford Anything, OG, and special guest Doug Cunnington from the Mile High FI Podcast. This is an episode you don't want to miss! In the second half of the show, we dive into the sensitive topic of what to do when you and your spouse can't agree. You won't want to miss this! Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we share a fresh perspective on personal and financial risk, featuring the always insightful Len Penzo (LenPenzo.com). Joe, OG and Len will dive into the complexities of managing your 401k and understanding the risk tolerance required to meet your goals. We'll share pivotal strategies for effective retirement planning and hopefully help you grasp why taking enough risk is crucial, especially for younger investors who have time to recover from potential losses. Listen in as we explore investment behaviors versus portfolio performance and how emotional decisions during market fluctuations can impact your financial journey. We don’t just tackle numbers here. We'll also examine whether widening your approach to include career risks and the often-overlooked social risks that can open doors to new opportunities is a good strategy. We'll talk about on growing your employment opportunities, ensuring long-term wealth, and balancing financial and emotional satisfaction. Plus, there just may be a slight amount of banter about Halloween treats, the joys of IRS conundrums, and the misconceptions of viral TikTok financial advice. To top it all off, we may or may not share stories about Joe’s adventures learning craps in Las Vegas, revealing the thrills and lessons of gambling. If you're searching for lessons, it may include the importance of knowing when to walk away, and the camaraderie forged at the casino tables. Whether you’re tuning in for practical financial strategies or just to enjoy some relatable stories and laughs, this episode is packed with takeaways on looking at risk differently in every facet of your life. Introduction to Debt Management Welcome to the Stacking Benjamin Show Discussing Risk with Len Penzo The Fortune Cookie Incident Understanding Risk Tolerance Career and Social Risks Halloween Treats and Risks Stocking Up for Halloween Diving into Risk Management TikTok Minute: Career Success Doug's Trivia: Understanding 1031 Exchange Listener Question: Employer-Sponsored IRA Plans Vegas Stories and Gambling Tips FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-halloween-1591 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Grab your coffee mug and join us for a journey full of strategic insights and valuable life lessons. Business legend Seth Godin joins us to share his wisdom on financial strategy and personal success. From college applications to wedding planning, Seth's advice on using a strategic compass over an outdated map will help you navigate big decisions and avoid wasting time and potential. Plus, we explore the balance between effortless yet intricate service and strategic pricing, advocating for value over cutting costs like Walmart because, sometimes, the tension in the experience is what makes it memorable and rewarding. There are plenty more actionable takeaways in our discussion with one of the most prominent gurus in marketing. Mainly, we delve into why having a well-thought-out strategy for life and personal finance can make all the difference. Learn from Seth's rich experience—from guiding startups to success to creating impactful strategies. We also explore the historical strategies that have shaped businesses like Yahoo and Google. Seth emphasizes the importance of vocalizing strategies, balancing personal agency with systemic constraints, and the essential threads of strategy: time, empathy, games, and systems. Using personal finance as a lens, Seth helps you understand complex concepts in a relatable way, underscoring how strategic thinking can transform everything from wedding expenses to retirement planning. Of course, that's not all. In our headline segment, we share the results of a recent study by Harvard, Vanguard, and others on 401k plan "leakage." New rules allow people to take annual withdrawals from their retirement plans. Will people abuse this new rule? The results of this study are surprising, to say the least. We discuss how to use 401k loans, why we don't favor them, and strategies to plug leaks so that your financial boat doesn't sink. On top of that, we also share trivia from Doug and much, much more! This may be your favorite Monday on Stacking Benjamins! Run of Show Morning Optimism and Weekend Plans Saluting Our Troops Special Guest: Seth Godin on Strategy The Importance of Strategy in Personal Finance College Applications and Life Strategies Seth Godin's Background and Achievements Understanding Strategy: Time, Empathy, Games, and Systems Walmart's Competitive Edge Freelancing on Upwork: A Race to the Bottom Justifying Higher Prices The Power of Peer Groups Mentorship vs. Peer Groups Personal Experiences with Peer Groups Trivia Time with Doug 401k Loans and Retirement Plan Leakage The Importance of Cash Reserves Upcoming Events and Meetups Consulting Firm Anecdote FULL SHOW NOTES: https://stackingbenjamins.com/create-you-life-strategy-with-seth-godin-1590 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever met someone whose retirement was wrecked by poor tax planning? While tax planning is essential, one big-named figure in the financial community who's a tax expert says that tax planning may be over-emphasized. But is it? Today, we're joined by experts Deb Meyer (Beyond Budgets podcast), Sean Mullaney (FI Tax Guy YouTube Channel), and the guy behind the Earn & Invest podcast, Doc G. Our financial experts will debunk common tax myths and provide actionable insights for a secure financial future. They'll explore the essential differences between marginal and effective tax rates, and you'll learn how effective tax planning can positively impact your retirement. Discover how to leverage tax calculators to avoid dreaded tax surprises and understand the nuances between Roth and traditional retirement accounts. Our enthusiastic experts bring humor and real-life examples into the mix, making complex tax strategies accessible to everyone, whether you're an entrepreneur or planning for retirement. In the second half of our discussion, we shift focus to practical financial advice. Discussions revolve around the temptation to overly optimize tax shelters and the importance of balancing tax efficiency and accessible funds. We cover concerns about the 'tax torpedo' affecting Social Security taxes and highlight the nuanced approaches required for better tax planning in an investor's journey. The insights shared aim to demystify tax planning for listeners, helping them shape sound financial strategies tailored to their personal circumstances. At the midway point, we'll pause for Doug's trivia question, today focused on a BIG tax case: Al Capone's run-in with the IRS. We'll share stories about his untaxed empire and discuss Walt Disney's clever tax maneuvers. We think you'll laugh through valuable tips on diversifying tax statuses and recovering tax bases. Hopefully, you'll leave with a better grasp of maximizing your tax efficiency and preparing for a financially stable future. Ignition Sequence and Lift-Off Introduction to the Stacking Benjamin Show Meet the Hosts and Guests Tax Talk and Trivia Teasers Welcoming the Financial Experts Diving into Tax Planning Effective vs Marginal Tax Rates Tax Planning for Entrepreneurs The Importance of Tax Diversification Trivia Challenge Begins Al Capone's 1931 Income Mystery Guessing Al Capone's Untaxed Income Revealing the Real Answer Financial Nerds and Tax Concerns The HSA Debate Annuities and Tax Gotchas Cash Value Life Insurance Podcast Highlights and Farewells S-Corp vs Sole Proprietor Learn more about your ad choices. Visit podcastchoices.com/adchoices

Explore how to score big with creative income strategies with us! Today, we'll dive into an in-depth case study on private equity in professional sports teams and discover how to use similar strategies to increase your wealth growth. You'll learn actionable advice on maximizing revenue sources, including tactics like Roth IRA conversions, covered calls, and creative investments like drop shipping during retirement and car rentals. We'll share a host of diversified financial insights that can help optimize your assets...all while having a bit of fun along the way. Later, catch our hilarious TikTok minute where we highlight a woman's misguided attempt to buy quarters on Amazon. In the 'Better Call Saul' segment, we tackle a listener’s question about retirement planning, providing practical tips that can be applied to everyday life. Of course, you don't want to miss Doug's trivia segment, where you’ll gain intriguing knowledge, like the anniversary of Marie Antoinette's last day and the history of Cutco knives. Hopefully you'll walk away with both valuable takeaways and a smile. Run of Show: Unexpected Shopping Spree Welcome to the Stacking Benjamin Show Money Urologists and Case Analysis The Value of Cash Payments Inflation and Economic Insights Private Equity in Professional Sports Leveraging Personal Finances Creative Income Streams Maximizing Investment Returns Flexibility in Financial Planning Mark Cuban's Business Insights Real Estate Ventures and Lessons The TikTok Minute: Math Mishap Trivia Time with Doug Roth Conversion Strategies Show Wrap-Up and Listener Review FULL SHOW NOTES: https://stackingbenjamins.com/big-money-in-sports-1588 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Do you think you're bad at math? Who doesn't! Whether you're an algebra whiz or struggle with subtraction, today's episode is for you. Join us as we dive into the exciting intersection of math and finance with Ben Orlin, author of 'Math with Bad Drawings.' We'll uncover the unexpected fun in mathematics and learn how understanding concepts like statistics and standard deviation can reveal the hidden stories within numbers. Ben's perspectives on embracing mistakes and the intrinsic link between math and finance offer a fresh look at these often daunting subjects. In our headline segment, discover the top strategy for achieving millionaire status through consistent investment in--believe it or not--nothing fancy! Danny Noonan shares the results of Fidelity insights into the lives of '401k millionaires,' spotlighting the power of patience and discipline over high-risk opportunities, underscoring sustainable financial growth. Finally, Doug enlivens the discussion with intriguing trivia on the differences between mean and median averages. Doesn't that sound hilarious? Of course, there's much more, so join us as we weave together actionable financial advice with engaging stories, making complex concepts like math and finance accessible and relatable for everyone. RUN OF SHOW Monday Morning Vibes Financial Wisdom with a Twist Introducing Today's Mentor: Ben Orlin Math and Bad Drawings The Beauty of Mathematics Breaking the Economy with Dice Statistics: Lies, Damn Lies, and More Tweaking the Guinea Pig Bed Embracing Mistakes in Learning The Power of Walking Away Unexpected Solutions in Math Good vs. Great Mathematicians Math and Mentorship The Collaborative Nature of Math Understanding Averages The Storytelling Power of Math The Importance of Consistent Investing Wrapping Up and Final Thoughts FULL SHOW NOTES: https://www.stackingbenjamins.com/ben-orlin-sb1587/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today's show tackles the age-old dilemma: is it better to have good health or more money during your retirement years? Join our lively roundtable as we discuss balancing financial planning with health priorities, featuring insights from Jesse Cramer of 'The Best Interest Podcast', Paula Pant from 'Afford Anything', and OG. Learn how different retirement stages can affect your spending habits, and explore creative ways to integrate health expenses into your financial plan. Plus, discover actionable tips on motivating yourself to stick to a healthy lifestyle and whether to invest in gym memberships or home equipment. Don't miss our contributors' take on the potential misuse of Health Savings Accounts (HSA) and their hilarious anecdotes about life and fitness. Run of Show: Introduction and Show Opening Panel Introduction and Health vs. Wealth Debate Segway and Scooter Anecdotes State Farm Advertisement and Personal Stories Health and Retirement Planning Trivia Question and SNL Discussion Comedian Salaries Revealed SNL Cast Member Earnings HSA: The Health Savings Account Debate Navigating Healthcare Plans Choosing the Right Workout Routine Podcast Highlights and Upcoming Guests Final Takeaways and Closing Remarks FULL SHOW NOTES: https://www.stackingbenjamins.com/good-health-vs-more-money-retirement Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

A recent Investment News piece shines a light on investment advisors (in this case we think that should read "investment salespeople") are recommending some truly ugly investments to investors. We'll dive into how the work, so hopefully you'll discover why certain alternate investments might send alarming signals for your portfolio. We go back in history to share hints at market risks that often go unnoticed until it's too late. We'll talk about the dangers of illiquidity, high fees, and obscure ways of measuring returns. You'll come away learning some shocking truths about leveraged investments and alternative products that make you question their place in any strategy. In our TikTok Minute, we'll share which bank one comedian calls the perfect partner for your needs. Is he right? Plus, later we'll help a listener who thought he'd Better Call Saul...Sehy and OG. Maybe OG needs to re-velvet his hammer on this one, and he manages to go into a diatribe that you shouldn't miss. We'll talk about career decisions, having more money than "Coast FI," and more on today's episode. Rounding out the episode, Doug shares his amazing trivia question, including YouTube's billion-dollar origins AND a ton of other events that happened on today's date in history. RUN OF SHOW: Countdown to Live Show Introduction and Show Overview Investment Warning: Be Cautious Investment Strategies and Mistakes Alternative Investments: Risks and Rewards Understanding Business Development Companies The Reality of Non-Traded REITs Final Thoughts on Liquid Investments Interval Funds Doug's Trivia Question The TikTok Minute Better Call Saul: Career Advice for Michael Conclusion and Listener Reviews FULL SHOW NOTES: https://www.stackingbenjamins.com/beware-investments-navigate-investing-waters Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Josh Brown joins us on today's episode for a thoughtful investment discussion in Mom's basement. Discover why "buying the robots" is a must, why everyone having money is a big fat negative for the economy and more. It's a wide-ranging conversation with one of the top advisors in the USA, and we're excited about all that Josh will share with our Stacker audience. In our headline segment, we'll discuss the importance of understanding insurance, especially in light of Hurricane Helene. Learn how to make your donations count and why revisiting your financial plan is essential for future confidence. Later, we'll shift gears to Hollywood, where aging protagonists are thrown back into action. Jeff Bridges reunites with his past in a gripping FX series, while Gary Oldman’s stellar performance in Apple TV's 'Slow Horses' takes the spotlight, though its pace might test your patience. Don't miss the brief nods to John Lithgow and Stanley Tucci and a fleeting mention of Mel Gibson, rounding out an episode rich in actionable insights and entertainment industry intrigue. Introduction and Apple Music Dilemma Apple Maps and Pretzel Problems Saluting the Troops and Show Introduction Robots and Automation Discussion Hurricane Helene and Financial Lessons Retirement Planning Insights Nvidia and Technology Takeover Pandemic's Impact on Inflation Media's Role in Financial Information Hollywood vs. Reality: The Truth About Wall Street The Wolf of Wall Street's Influence on Modern Traders Josh Brown's Perspective on Market Culture The Importance of Financial Designations Hurricane Helene: Impact and Relief Efforts The Real Cost of Insurance and Rebuilding Charitable Giving: Time, Expertise, and Goods Upcoming Events and Meetups Final Thoughts and Takeaways FULL SHOW NOTES: https://www.stackingbenjamins.com/josh-brown Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's a shock: our least favorite brokerage company is in the news again with some monster hidden fees. Robinhood is accused of charging customers a huge "spread" between the amount option buyers pay and the amount sellers receive. While this isn't a charge on the statement, it's a lot of money (nearly double) that other companies charge. This topic got us thinking: what hidden charges, expenses, and costs exist in our life that we overlook or choose to ignore? How much are all of THESE costs adding up? We have the perfect triumvirate for this discussion. Jen Smith, one half of the Frugal Friends duo joins us (they talk consumption non-stop on their podcast). Roger Whitney chimes in (his Retirement Answer Man helps people control excess costs in retirement or when prepping). OG also joins in, with all of his experience helping clients reach their goals. It's a wide ranging, fun discussion, from the cost of pollution to hidden Doordash costs we didn't know about! Of course, halfway through this episode, we take a break to challenge these contributors to a round of Doug's epic trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/hidden-fees-and-costs Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Learn the secrets behind never worrying about saving money again! We share the story of an individual who invested early and effectively, reaching financial security by 25, and how YOU can apply these principles regardless of age. Our main discussion highlights how to achieve financial freedom and the importance of staying disciplined with your savings over time, offering valuable insights into the pitfalls and opportunities of early investing and the flexibility it can bring to your lifestyle choices later on. Plus, we explore the balance between traditional investments and investing in personal growth opportunities for a brighter financial future. In our TikTok minute, comedian Greg Warren addresses compounding interest and how the accumulative consequences of poor decisions can pile up in life. This sets the stage for our Better Call Saul...Sehy and OG segment, where we tackle a listener's question about disability insurance, offering practical advice for securing comprehensive coverage and understanding the importance of one's own occupation policies. We provide actionable tips and clear explanations to help anyone navigate the often confusing insurance world. Doug's trivia this episode revolves around the band Oasis and the quirky history of Ticketmaster fees, providing a nostalgic trip down memory lane for music fans. We wrap up with listener feedback, upcoming event announcements, and highlights like Joe's adventurous dining experiences in Peru (including some surprising menu items!). Tune in for a packed episode filled with financial wisdom, humor, and a dash of Doug's signature fun facts. Show Rundown Introduction and Setting the Stage Welcome to the Stacking Benjamin Show Today's Topic: Never Worry About Saving Money Again Headline: What If You Never Had to Think About Saving Money? The Power of Compounding and Investing Early Challenges and Pitfalls of Early Investing Flexibility and Lifestyle Changes Starting Late: It's Never Too Late to Begin Trivia Time with Doug Money and Reconciliation College Sales Experience TikTok Minute: Comedian Greg Warren Disability Insurance Dilemma Listener Feedback and Reviews Upcoming Events and Final Thoughts Joe's Peru Adventure FULL SHOW NOTES: https://www.stackingbenjamins.com/never-worry-about-saving-money Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jump into Monday with a whirlwind of money topics! We start by celebrating the arrival of fall and the excitement around baseball playoffs (especially for Detroit Tigers fans). But the real fun begins after we salute the troops and dive into the main event: a riveting conversation with Erin Wade, a former lawyer turned chef and entrepreneur. Have you ever thought you wanted to do more with your life than you currently do? Erin shares her tumultuous journey from corporate law to opening one of America's top restaurants, Homeroom, and drops valuable lessons on following your passions and creating a rewarding work environment. During our headline segment, we discuss the recent Federal Reserve rate cuts and what it means for your finances. How can you benefit from lower interest rates? We'll dive into how interest rate cuts work and help the economy. We discuss what this means for your savings, debt strategy, and more. Plus, macaroni and cheese-related trivia AND—how to take your mac and cheese recipe to the next level! Monday Morning Musings Baseball Playoffs Excitement Saluting Our Troops Introducing Today's Guest: Erin Wade Mac and Cheese and the Holiday Season The Journey to Entrepreneurship The Importance of Passion and Play Challenges and Triumphs in the Restaurant Industry Empowering Teams and Open Book Management Mac and Cheese Tips from the Expert Mac and Cheese Tips and Tricks Doug's Mac and Cheese Trivia Powdered Cheese and Nostalgia Federal Reserve and Interest Rates Explained Impact of Interest Rates on Loans and Economy Credit Scores and Mortgage Tips Car Market and Financing Insights Upcoming Events and Closing Remarks Post-Game Press Conference FULL SHOW NOTES: https://www.stackingbenjamins.com/erin-wade-from-attorney-to-mac-and-cheese-millionaire-1581/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we focus on accountability, diving into what it means to be responsible for your financial decisions. One recent blog post states that it's easier than ever to get yourself into massive trouble with your money. To what extent is this your fault? How can you protect yourself better from making a mistake that leaves you in financial ruin? We discuss the rapid pace at which bad decisions can be made due to modern conveniences like apps and online services. Jesse Cramer (Best Interest Podcast) emphasizes the importance of finding a 'bigger Yes' to avoid impulsive spending, while Paula Pant (Afford Anything) speaks on the broad accessibility of money-making opportunities in the digital age. OG suggests taking actionable steps towards financial goals to keep the momentum going. Today's trivia quiz is all about the history of 'The Tonight Show,' and maybe features a tangent or two about toga parties. For a bit of drama, there's a video clip debunking myths about cash value life insurance. Overall, as always, today we bring you an engaging mix of humor and practical financial advice. Introduction and Opening Remarks Show Introduction and Guest Lineup Welcoming the Hosts and Guests Discussion on Accountability and Financial Responsibility Main Topic: The Degenerate Economy Debate on Government Intervention and Free Market The Role of SEC and Financial Disclosures Gambling, Lotteries, and Financial Ethics Trivia Contest Nostalgia and TV Memories The Tonight Show Timeline Guessing the Debut Year Revealing the Correct Answer Financial Advice and Scams Creating a Financial Plan Weekend Plans and Wrap-Up FULL SHOW NOTES: https://stackingbenjamins.com/taking-personal-responsibility-for-your-finances-1580 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What does retirement mean in today’s world? For some, it's no longer about quitting work for good but about transitioning to something more purposeful and fulfilling. Today, Joe, Doc G, and our guests explore the many facets of retirement, purpose, and the balance between work and personal passion. Join us as we take you to CampFI Midwest 2025, where we'll share stories from amazing Stackers on their journey to financial independence. Discover how Kristen finds community and purpose, Donna navigates significant life transitions, and Tom redefines retirement with passion and flexibility. You'll also hear Joe Saul-Sehy discuss misguided stock purchases, Chris's investment in outdated tech, Kristen's high-fee investments, Jordan's tech stock downturn, and a humorous tale of timeshare regret. Tune in for actionable insights, personal experiences, and valuable lessons that highlight both the triumphs and challenges faced by even the most intelligent investors. Topics: Introduction and Setting the Scene Campfire Guests and Trivia Contest Doug's Hilarious Commentary Journey to Campfire and Minnesota Vibes Inspiring Stories and Personal Growth Kristin's Journey to Financial Independence Trivia Challenge Begins Chelsea Brennan's Bold Move Guessing Game Tension Doug's Hitchcock Trivia Answer Donna's FIRE Journey Financial Empowerment and Mindset Tom's Story and Retirement Insights Lessons from CampFI Dumb Money Mistakes That Smart People Made Whether you're planning for retirement or just looking for inspiration to find more meaning in your second half, this episode is packed with insights, laughs, and the wisdom of experience. What You’ll Learn: How retirement has evolved from leaving the workforce to finding purpose. Why it's important to fill your time with meaningful activities, paid or unpaid. The concept of "strength to strength" and how it shapes a fulfilling second half of life. Financial lessons and humorous stories from our hosts and guests. How to avoid common money mistakes, and what to do if you've already made them! FULL SHOW NOTES: https://stackingbenjamins.com/live-from-camp-fi-1579 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Wealth historian Megan Gorman stops by the basement and drops intriguing nuggets on how U.S. presidents like FDR and Ulysses S. Grant navigated their finances. There are many lessons you can learn from these iconic figures. Later, our headline conversation meanders through ERISA's 50-year legacy and political party impacts on investments, preparations unfold for an RV trip to Oregon. The adventure continues with exotic travel stories, packing tips, and reflections on Dave Barry's life lessons. Listener engagement and very-important debates, including daylight savings time, ensure there's never a dull moment! Join the lively trio of Joe, OG, and Doug as they blend retirement strategies with a dash of humor, exploring everything from coffee mugs to memes. 00:00 Coffee Mug Conundrum 01:43 Welcome to the Stacking Benjamin Show 04:53 Presidential Finances with Megan Gorman 06:57 FDR's Lobster Investment 13:12 Biden and Trump's Real Estate Ventures 20:22 Calvin Coolidge's Financial Anxiety 25:38 Ulysses Grant's Financial Struggles 32:56 Lessons from Presidential Finances 37:22 Shawshank Redemption Anniversary 38:12 The Shawshank Redemption's Box Office Struggles 38:57 Trivia Time: John Travolta's Box Office Hit 39:31 Ohio's Role in The Shawshank Redemption 40:24 Ulysses S. Grant and Investment Strategies 41:46 College Application Essays: Writing vs. Storytelling 45:20 The Impact of ERISA on Retirement Planning 49:19 Maximizing Your 401(k) Benefits 56:20 Investing Through Political Cycles 01:03:48 Stacking Adventures: New Podcast Announcement 01:08:40 Dave Barry's Life Lessons 01:16:52 Final Thoughts and Farewell FULL SHOW NOTES: htttps://stackingbenjamins.com/presidents-and-their-money-1578 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Game Show Fun and Financial Missteps with the Stacking Benjamin Show On today's popular game show segment we present: '15 Ways to Lose Money in the Financial Markets,' where contributors Jesse Cramer, Paula Pant, and OG explore investment pitfalls. The show presents financial advice in a light-hearted, engaging format, complete with a trivia question celebrating author George RR Martin’s birthday. Contributors discuss speculative trading, panic selling, margin investing, and more, ending with practical takeaways on avoiding investment mistakes. The episode is rounded off by discussions on meme stocks, game shows, pop culture, and practical financial planning tips, all with the usual fun and wit of the Stacking Benjamin team. Introduction and Opening Remarks Meet the Contributors Game Show Begins: 15 Ways to Lose Money in the Markets Round One: Poor Investment Decisions Round Two: Strategies to Avoid Trivia Break: Game of Thrones Special Guessing the Number of Deaths in Game of Thrones Counting On-Screen Deaths: The Research Wildfire Explosion and Mass Casualties Final Guesses and Results Discussing Game of Thrones Infographics Meme Stocks and Financial Decisions Ways to Lose Money in the Market Podcast Updates and Weekend Plans Closing Remarks and Lessons Learned FULL SHOW NOTES: https://stackingbenjamins.com/how-to-lose-money-in-financial-markets-1577 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe and OG create a case study focusing on the Dallas Police and Fire Pension System's struggles, diving into poor investment choices and their impact on employees. Joe relays the perils of complicated investments, advocating for more straightforward and more manageable strategies. The team also shares a TikTok moment about evaluating wealth through trash cans, discusses an unusual employer's 401k vs. Roth IRA match proposal, and debates their most disappointing concert experiences. Introduction and Doug's Antics Today's Show Overview Pension Fund Struggles Dallas Police and Fire Pension System Pension System Mismanagement Lessons for Average Investors Private Equity Pitfalls The Importance of Professional Management Trivia and TikTok Minute Buffet or Buffett? The Trash Can Wealth Indicator Listener Question: Employer Matching Roth IRA Contributions Concert Disappointments and Highlights Wrapping Up: Key Takeaways FULL SHOW NOTES: stackingbenjamins.com/all-about-pension-funds-1576 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe and OG dive into retirement planning with Christine Benz, Morningstar's Director of Personal Finance and Retirement Planning. Christine shares her insights on pivotal retirement lessons and the importance of purpose, relationships, and health in retirement. In our headline segment, the team also explores the recent changes in real estate commission structures, emphasizing the need for negotiation skills and knowledgeable agents. Lively banter and tips for financial well-being abound in this packed episode. The Weekend Football Struggle Salute to the Troops and Podcasting Life Introducing the Stacking Benjamin Show Hair Loss and Financial Planning Christine Benz on Retirement Planning The Importance of Purpose in Retirement Social Interactions and Technology in Retirement Fritz Gilbert's Retirement Journey The Right Retirement Date and Financial Considerations Ramit Sethi on Retirement Spending Morningstar Trivia and Walden Thoreau's Influence and Real Estate in the News New Etiquette in Real Estate Negotiations Changes in Realtor Compensation Impact on Buyers and Sellers Navigating the New Real Estate Landscape Balancing Commission and Sales Strategy Real Estate Fees and Market Dynamics Rules of Thumb for Home Buying The Future of Real Estate and Consumer Choices Conclusion and Final Thoughts FULL SHOW NOTES: https://stackingbenjamins.com/master-your-retirement-plan-christine-benz-1575 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode of The Stacking Benjamin Show, host Joe (alongside guests Jesse Cramer from the Best Interest Podcast, Paula Pant from Afford Anything, and our own OG) delves into transforming financial goals into ongoing quests. They discuss the importance of falling in love with the process and how systematic approaches and habits can aid in personal growth and goal achievement. The episode wraps up with a trivia challenge, financial wisdom, and maybe some slightly humorous banter, emphasizing the importance of seeking real financial advisors. Links to the guest podcasts and additional resources are available at StackingBenjamins.com. Spider Pig Introduction Welcome to the Stacking Benjamin Show Meet the Hosts and Guests Creepy Old Guy Stuff Podcast Goal Setting Discussion Begins Financial Metaphors and Humor Introducing Jesse Kramer The Best Interest Podcast State Farm Sponsorship Mid-Year Goal Setting Do Quests, Not Goals Health and Fitness Goals Procrastination and Goal Setting Wayne Dyer and Goal Setting The Importance of Starting Now Trivia Time with Doug Thanksgiving Pecan Pie Debate Guessing Game: Percentage Debate Trivia Question: Jim Cramer's Hedge Fund Goal Setting: Systematic Approaches Quest vs. Goal: A Transformative Journey Fighting the Inner Dragon Podcast Highlights and Wrap-Up FULL SHOW NOTES: https://stackingbenjamins.com/turning-goals-into-adventures-1574 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome to a very special episode! Three experienced dads (teens and above) chat about teaching teenagers or people new to money management, good lessons to take with them for the future. They discuss their fears, their challenges, and the ways they've been able to help their kids succeed with money. Jon Acuff wrote a book on this topic with his daughters, and he shares a wealth of information from them. John Lanza (Art of Allowance podcast) just became an "empty nester" and shares how his kids successfully launched as well. Joe Saul-Sehy is the father of nearly 30 year old twins, who are also doing well with their money. They share do's, don'ts, and much much more. Introduction to the Episode Meet the Hosts and Their Parenting Fears Introducing the Celebrity Guest: John Acuff Discussing Parenting and Money with John Acuff John Lanza on Parenting and Empty Nesting The Challenges and Realities of Parenting Teens Repetition and Real-Life Lessons Finding Opportunities in Everyday Tasks The Value of Hard Work and Money Parenting and Teaching Financial Wisdom Kids' Perception of Parental Advice Encouraging Self-Awareness in Teens The Importance of Role Models Navigating Teen Challenges with Support The Fast Gauntlet: Quickfire Questions Final Thoughts and Takeaways FULL SHOW NOTES: https://www.stackingbenjamins.com/teaching-good-money-habits-to-kids-1573/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we focus on resilience in both personal finance and investments, as we celebrate the kickoff of a new professional football season! We're featuring an engaging discussion with Wharton professor and former NFL player Brandon Copeland. Highlights from this episode include Copeland's mission to teach financial literacy, strategies for managing cash reserves for retirees, and handling fraud cases with banks like USAA. The team emphasizes the importance of giving investments time to recover, as shown by the S&P 500 rebound post-COVID. They warn against keeping retirement accounts in cash and offer practical tips such as monitoring bank transactions, freezing credit, and aligning your portfolio with your goals. A contest on historical investment returns based on political parties is extended, and as you'd expect from a financial podcast, there's a recap of dramatic events from 'Below Deck Mediterranean' Season 5.  FULL SHOW NOTES: https://stackingbenjamins.com/kick-off-your-money-plan-brandon-copeland-1570 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we speak with some great coaches about the difference a great coach can make, and how hiring the wrong one can give you a horrible taste in your mouth (and lead you down paths that aren't helpful to your long-term growth). Coach Sharita Humphrey joins us, along with CFP Roger Whitney and Len Penzo to a great chat. Plus, we celebrate International Travel Day by diving into the best places to live or "slow travel" overseas. That AND much, much more! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Kyle Collins joins Joe and host Doc G for an episode of the Earn & Invest podcast to discuss a recent piece featuring Mark Cuban, a billionaire, talking about frugality. Do we really care what billionaires think about being frugal? Download/follow/subscribe to our "brother" show Earn & Invest wherever you're listening to Stacking Benjamins! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we ask David Bach the question: what does a latte truly have to do with your retirement plan...or your financial well-being in general? Plus, we chat with Sallie Mae about some trends in student loans. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Bola Sokunbi (Clever Girl Finance) has an amazing story of resilience, growing up in Europe, moving to Africa, and having to learn a BUNCH of financial knowledge from her mother, who made the mistake of trusting someone else with her financial knowledge. Today she tells her incredible story. Plus, Detroit Free Press reporter Susan Tompor joins us to share some scary stories about scammers. That and much, much more as we go WAY back in the vault of SB shows for this greatest hits episode. Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's show, what should YOU track for a better financial plan? We go WAY back in the archives to one of our early episodes. You'll hear us back when the podcast was young. :-) Enjoy the theme music, the Evil HR Lady, and more! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Sure, you've rented a car. Maybe your home. But what about renting your clothing, your tools, or even your Christmas tree (if you celebrate the holiday)? Today we talk about an emerging group of people who have taken renting to the extreme. They rent nearly everything. If you decide to rent are you asking to spend more money or is the concept of "ownership" outdated? Today we dissect renting and what it truly means AND how it affects your financial picture. We're excited that CFP Benjamins Brandt (Retirement Begins Today podcast) and Paula Pant (Afford Anything) join OG, Joe and Doug to help you make better rent/own decisions. Plus, of course, at the halfway point of our discussion, we make time for our epic trivia challenge! FULL SHOW NOTES: Add show notes URL here. Please include https://www at the beginning of the URL, that makes it clickable on YouTube Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We collectively lose MILLIONS because we skim our company benefit package and quickly pick options, or we simply take what we've always had and ignore the rest. Today we'll dive into the changing world of benefits. From tele-health to mental health and gym memberships, perks are looking different at companies than they did ten years ago. We'll share what's new in the world of benefits, what's out, how to pick smarter, and shine a flashlight on some hidden gold in that gigantic pdf most of us receive to make our choices. In our TikTok minute, we share the story of a hated football player and also a valuable money lesson. Do you have haters? Of course you do! Maybe you can learn something about cha-chinging the cash register in a quirky way on today's show! Of course, Doug shares his trivia, but we also open up a fun election-jitters contest. OG will explain, and we hope you participate. Joe will also unveil a new guide from Stacking Benjamins that could help you save thousands. He'll walk you through the details. FULL SHOW NOTES: https://stackingbenjamins.com/raising-money-smart-kids-1565 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

It's easy to feel cynical. The news blares bad news about "them" (defined squarely as whatever group you happen to disagree with). Social media shows you the most awful people, events, and situations. Everything that happens seems to reflect that the world is becoming more distrustful, and it's eating away at many of us. Stanford professor Dr. Jamil Zaki joins us today to give hope to cynics everywhere, by sharing data showing that we're actually far more trustworthy as a group than you may think. He also shares the cost of cynicism, and what to do if you're feeling particularly down about your fellow human beings. Especially with all of the negativity around the election, you'll find today's show is a bright spot to kick off your week! In our headline segment, we set out to share tips on buying used cars, but instead end up in a MONSTER discussion about the efficacy of buying used at all. We talk leasing, buying new, and the many ways you can buy used cars. We review the positives and drawbacks of each approach so that you can make a more informed car-buying decision. Of course, we also leave time for Doug's trivia, and much more! Are you near Minneapolis this weekend? Join Joe and a bunch of other Stackers in Stillwater, MN. on Thursday night at 6:30 (River Siren Brewing) for a pre-Camp FI party! We hope to see many of you there! Head to http://stackingbenjamins.com/meetup for details and to snag a free ticket. FULL SHOW NOTES: https://stackingbenjamins.com/the-power-of-optimism-jamil-zaki-1564 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What advice would you give your younger self just starting in the workforce? With many recent graduates securing their first "real" job, that's the question on our minds. Joining us to dish out sage advice, we welcome Paul Lambert ("Lambo") from the FILighter podcast, Paula Pant from Afford Anything, and our resident financial planner OG. In the second half of the show, sponsored by DepositAccounts.com, we dive deeper into less-common advice for new career entrants. Be sure to stick around for Doug's Bonnie-and-Clyde-related trivia question. FULL SHOW NOTES: https://stackingbenjamins.com/advice-for-recent-graduates-1563 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Remember the line in Lord of the Rings, "One ring to rule them all?" How about, "One tax shelter, available to all of us, to be the best of all?" Today we'll identify THAT investment shelter, tell you how to use it (and tips to avoid using it incorrectly). Here's a hint: it's NOT the health savings account (which may be better), because that account is not available to everyone. This type is truly a tool that everyone can use in the USA. Of course, that's not all. We'll talk MORE about this special tax shelter by sharing a TikTok minute that focuses on just how many people TALK about this shelter. It's truly amazing. We'll also answer a call from a stacker who's wondering if she should pay her house off or invest the money she has to finalize her mortgage. Which would you do? We'll share our advice with you AND her today! Of course, we'll also feature Doug's rhyming trivia, and much, much more. FULL SHOW NOTES: https://stackingbenjamins.com/what-is-the-greatest-savings-vehicle-1562 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

John Hope Bryant says that even if you're a money geek, soaking up as much knowledge as possible, financial literacy for all (not just you) is YOUR problem. Today the financial activist takes aim at everyone to pitch in and help bring up our entire world by empowering people to become more financially literate. If you've never heard John speak, you may not know that he grew up in Compton (Los Angeles) in a very poor home, and struggled to find financial security. Now, as a frequent media contributor and one of the biggest suppliers of economic and entrepreneurial training in the USA, John spreads the word that even people who "didn't get the memo" about being money savvy can help all of us grow our wealth. He makes that case today on the show (and we don't think you'll want to miss it!). You never leave a John Hope Bryant talk feeling uninspired and ready to perform better with your finances. In our headline, we dive into the significant stock market tremor a couple of weeks ago. What's happened since? What lessons should we have learned? Should you take your money out of the market? Invest more? How should you handle it? We've spoken a lot lately about how to invest wisely, but with this case study right in front of us, you'll see precisely why we've been driving home the point of economic security so much lately. Of course, we also leave time for Doug's trivia and much more! FULL SHOW NOTES: https://stackingbenjamins.com/financial-literacy-for-all-john-hope-bryant-1561 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Should you aim to die with zero, or is there a better way? What role does money play in our lives, and what can it do after we're no longer here? Diving into this deep topic on today's roundtable discussion, we welcome back Lacey Langford from the Military Money Show, Doc G from the Eatn & Invest podcast, and OG. In the second half of today's show, brought to you by DepositAccounts.com, we dive deeper into giving money to others while you are alive and how that can add happiness to your life. Be sure to stick around for Doug's Elvis-inspired trivia question. FULL SHOW NOTES: https://stackingbenjamins.com/die-with-zero-question-mark-1560 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You have all had so many estate planning questions and today we delivered answers, with certified estate planning attorney Tim Semro. It's an "estate planning all the time" episode, as we cover everything from estate planning headlines to our estate-filled TikTok minute. You also asked tons of questions about when to leave people money, what traits make a good executor, how do you help loved ones with disabilities, what if you don't want a relatives money, and how to minimize probate costs...plus much, much more. In our headline segment we focus on celebrity cases that have ended ugly. From Tony Bennett to Aretha Franklin and Chadwick Boseman, estate issues are seemingly always in the news. In our TikTok minute we shine a light on a top television show (Curb Your Enthusiasm) that brings up some awkward estate situations. On the back porch we show another family (It's Always Sunny in Philadelphia) that also may not end up happy with a recent estate settlement. All of that plus Doug's trivia on today's podcast. FULL SHOW NOTES: https://stackingbenjamins.com/all-about-estate-planning-tim-simro-1559 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever thought about quitting your job, getting out of the rat race, and instead working on your passion? Maya Chupkov is a force of nature, and did just that. After scoring what was the "job of a lifetime," she realized that the actual work didn't meet what she wanted in life. So instead, she quit that job to focus on her lifestyle and needs. Her new boss at a smaller paycheck firm wanted to promote her into more responsibility (and more money) and Maya again said "no." Instead, she spends her time shining a light on the plight of stutterers, something that has not only been a part of Maya's life since she's been born, but also has been a part of the life of one of our SB podcast hosts (Joe). Maya is not only now the host of the acclaimed Proud Stutterer podcast, but also is working a documentary about a man whose life changed because of his stutter, and not for the better. It's called Rock of Hope, and Maya today details not only what it took to quit a high paying job, but also how she's gained skills, connections, and funding for this new project. It's a fascinating walk through the life of a woman who's pursuing her dream: to help stutterers everywhere come out of hiding and focus on their strengths with the help of the community around them. In our headline segment, trouble on the "making more money" front. The Wall Street Journal reports that pay raises are shrinking. What do you do if you aren't going to be scoring as big a raise in the future as you have in the past? We share tips and ponder different avenues you should explore to try to not only tighten the belt, but make more money when others are not. We also spend some time on the back porch talking about Stackers who are Olympians, and feedback about our recent sandwich survey episode. Of course, we sandwich that all around Doug's amazing trivia question. FULL SHOW NOTES: https://www.stackingbenjamins.com/maya-chupkov-1547/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

The piggy bank is clearly outdated. What kid needs to learn about cash now? It's far more important to know what those plastic things in mom or dad's wallet really are and how to use them responsibly. While contemplating the piggy bank we asked ourselves, "What are some other outdated ideas about money that we're holding?" That topic created this wild ride of a podcast episode where OG, Doc G (Earn & Invest podcast), and Paula Pant (Afford Anything) share and critique each other's ideas of outdated money concepts. You'll hear everything from big ideas to tactical solutions that no longer work on today's show. From the concept of "retirement age" to "don't refinance until you can beat your interest rate by 2%," you'll hear it all. Of course, as we do every Friday, we'll feature our year-long contest between our contributors for the big Dollar Store trophy prize. Paula actually won trivia last week...can she make it two in a row? FULL SHOW NOTES: https://stackingbenjamins.com/outdated-financial-concepts-1557 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's the most fun way to look at inflation? Well, even though it might not be fun to watch your wallet disappear at the grocery store, it is VERY fun to watch trends in food costs over time. Len Penzo began his annual sandwich study to just prove that packing your lunch is cheaper than buying food at a restaurant. He also wanted to show just how much money you could save to either pay down debt or invest. Instead, many years later, Len's sandwich study is always compared to the classic "Big Mac" study, where they track the price of a Big Mac. We prefer Len's study because making a sandwich is healthier, cheaper, and also maybe a little more fun. So today we'll compare the cost of ten sandwiches and see which one is this year's champion...but more importantly, we'll see if your grocery bill has gone up or down from a year ago. In our headline segment, your home is your castle so it probably holds LOTS of cash value that you may want to tap into during your retirement years. How do financial planners look at home prices that might not rise as quickly in the future as they have in the past? We'll chat about housing, selling your house for retirement, how people navigate selling and "downsizing" in real life, and much more. Of course, we still take a call from a Stacker on our Better Call Saul....Sehy and OG segment. Plus, we always leave room for a helping of Doug's trivia. FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-2024-sandwich-survey-1556 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You've played the game by the rules...moving your money from a 401k to an IRA when you change jobs (which happens in the USA far more often than you'd think). But are you forgetting a "step two" that could cost you over a million dollars? A recent Wall Street Journal piece says that you may be making a HUGE mistake. Today we'll break down where people are getting it wrong so that YOU aren't stuck with a much smaller retirement nest egg than you'd hoped or expected. We also take a question from a Stacker who's accepted a "job" that pays her as a 1099 "employee." How does she make sure she doesn't owe too much in taxes at the end of the year? In general, how should she set up her money now that she's going to be responsible not just for taxes, but for her own benefits and more? We'll help her (and maybe you, if you ever decide to start your own business or side hustle) take control of her money so that she's in great shape come tax time and beyond. Of course, we also share Doug's amazing trivia question AND a TikTok minute that might mess with Doug's brain.... (not too difficult, really). FULL SHOW NOTES: https://stackingbenjamins.com/401k-rollover-mistakes-to-avoid-1555 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are we overusing popular "helper" apps like DoorDash, Instacart, and Uber? One popular blogger thinks so, which made us ask some of the top podcasters in the money space: do you agree? This simple question helped create a fantastic discussion about the importance of community, real-life neighborhoods, avoiding "using" people while still appreciating them, and so much more. Dr. Bill Yount joins us from the Catching Up To FI podcast. Bill's a natural community builder, so we were thrilled that he agreed to join Paula Pant (Afford Anything) and Doc G (Earn & Invest) in this wide-ranging discussion. As always, we'll also include another EPIC edition of Doug's trivia in the middle of today's chat! FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-save-big-money-on-doordash-instacart-and-uber-sb1554 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

One of the world's largest money management companies is raising fees AND has a new CEO from a competing firm. Are times a-changin' at Vanguard? We'll dive into all of the behind-the-scenes action, and discuss how this just might affect your wallet. Of course, we'll widen the argument for those of you NOT at Vanguard. If your money is with another firm, what happens when there's a change at the top? What should you look out for when it comes to prudently deciding whether it's time to move your nest egg? Plus, in our TikTok minute, one crypto is paying a walloping 19.55 percent! Cowabunga! Should you back the truck up and shovel money in? We'll share our thoughts. And we take a call from a Stacker wondering what "Velocity Banking" is all about? How does it work, and if you can use this method to pay off your loans faster, should you jump in? All of that AND Doug's trivia on today's show! FULL SHOW NOTES: https://stackingbenjamins.com/vanguard-changing-course-1553 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Want to know how to make your money perform better? Begin controlling that stuff between your ears. Between negative self-talk and obviously-bad money moves, we find plenty of ways to sabotage our long term goals. Today we're joined by behavioral economist Dr. Daniel Crosby, who dives into what he calls "the soul of money." We'll discuss wisdom from some of the world's greatest legendary figures, like Alexander the Great, and dive into stories like The Kite Runner and what we can learn about money, happiness, "more," and being truly wealthy. Plus, in our headline segment, one type of worker is loading up on cash inside of their retirement fund at work. Who? It turns out, that it's workers at companies that have decided to default retirement contribution plan percentages at a higher rate. Huh? It's not only fascinating, but probably the reason why you might be able to save more...but never have been able to pick the lock. If you're a great saver, you'll also know this is the key--so send this headline to your friends! Joe and OG tackle this topic from beginning to end, and hopefully, you'll be richer as a result (or on your way to riches). We also take a call from Stacker Blake, who asks about his Acorns account. Now that he's been using it for awhile, should he move it to a different home so that he doesn't have several different accounts? Of course, we'll also save time for Doug's trivia question, groan about the state of Ohio, and more! FULL SHOW NOTES: https://stackingbenjamins.com/psychology-and-money-1552 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you could win medals for your financial performance, what would you need to accomplish? Today, four-time Olympian and the first American woman to medal in both the winter AND summer games, CFP Lauryn Williams, joins us to both share the inside look at tonight's opening ceremonies and help our roundtable team outline the moves YOU need to make to score gold with your money. We'll talk about the foundation it takes to begin the journey and then the moves beyond to be a true champ. Of course, our gold-medal team of Paula Pant (Afford Anything) and CFP OG from our podcast join in the fun. On top of some great advice, you'll also hear our weekly trivia challenge between our participants as THEY try to score gold for correct answers. It's a great episode marking a fun date in history. Let the games begin! Learn more about your ad choices. Visit podcastchoices.com/adchoices

A new study shows that baby boomers are tapped out. On today's show we dive into the reasons why this is the case and explore a TON of ways that you can ensure that you aren't running out of money before you run out of life. We'll explore lots of areas, like: Health care costs Automatic savings plans Better investing to increase returns Avoiding common pitfalls ...and lots more. In our TikTok minute we explore estate planning. What happens when dad is about to die and he tells his son, "Just put me in my boat and let the sea take care of me." The reply from the son may not be what you'd expect. We also take a call from Stacker Eric, who's wondering if he should keep pumping money into his HSA even though he has a significant amount saved already. What if he doesn't need that money? Of course, we also save time for Doug's trivia AND we avoid celebrating "old joke day." FULL SHOW NOTES: https://stackingbenjamins.com/running-out-of-money-in-retirement-1550 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Tessa West has seen lots of people in the wrong careers. Either the job has drifted from what they'd initially thought, or maybe they're a leader at work, but they're passed over for promotions or raises. There are many reasons why people feel the malaise of a job that doesn't work anymore, but the effect is nearly always the same. Either you stagger through the work, wasting your life, or you dream about early retirement. What if there was another answer? What if the job that lights you up is actually out there? You need to know the tools to go find it. That's what Tessa Woods gifts us on today's show. You'll learn how to throw off the ennui and find meaning at work by either rebooting your current career or finding a new job elsewhere. We'll talk about how to engage in effective networking, how to assert yourself as a leader in your field, and why changing fields isn't a bad idea--even if you're an older worker. While many of us think that we wouldn't qualify for jobs against seasoned pros who've already had experience in the given area, Tessa shares how and why employers often want someone with a fresh perspective. You have to know how to sell your strengths, and we'll share some keys today. In our headline segment, we'll review how Mark Cuban saved his fortune from disaster when everyone else lost money in the 2000-2002 tech wreck. We'll share the tools he used and how it all went down. Plus we'll answer the question: should YOU also use this strategy to avoid losses? It's a great question, and we tackle it head-on! We'll cover options, market declines, and the financial planning reasons Cuban executed this strategy. FULL SHOW NOTES: https://stackingbenjamins.com/find-a-job-you-love-1549 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How wealthy are you? Today we talk about different currencies than cash. While you may be monetarily rich, if you're truly stacking a better life, there are other priorities. Today we dive into a piece from the Retirement Manifesto blog (and from past guest James Clear) on building OTHER types of wealth. What are they? We ask contributors David Stein (Money for the Rest of Us podcast), Allysa Maizes (Amplify Your Wealth online), and Doc G (Earn & Invest podcast). This all-star cast has spent lots of time and energy maximizing not just their financial readiness for independence, but also their overall wealth in many of the areas we discuss today. Of course, we'll pause halfway to battle out Doug's trivia. Mom's been making a surge in our year-long competition. Can David Stein (playing for mom) keep the run going? Will Allysa (playing for Paula Pant) start reeling in mom and OG? You'll find out today! FULL SHOW NOTES: https://stackingbenjamins.com/5-types-of-wealth-1548 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's show we dive headfirst into the mailbag, and answer your excellent questions on every facet of investing, saving, and protecting your money: Do I need a trust? What should I do with these savings bonds? Should I take my money out of a 529 college savings plan? Can I stop saving money well before I retire? ...and LOTS more. We're excited to not only bring you those questions, plus our TikTok minute (wait until you hear THIS bride...), AND Doug's incredible trivia question. Plus, we may rail on too long about fake IDs (just to help parents know how to spot them, of course). FULL SHOW NOTES: https://www.stackingbenjamins.com/investing-saving-and-protecting-your-money/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Does winning at investing mean that you need more information, a better rule set to follow, or better connections? Our guest today says that while those can be advantages, it's hard to "win" those games. However, there is one method which can help us easily increase our odds of becoming a better saver and investor. More good news? This method is available to us all. Our guest today says learning from the Stoics, philosophers from ancient times, we can easily beat the average investor and we can set ourselves up for life. If you're listening to SB for that reason, you're in a for a treat. Darius Foroux is not only one of our favorite bloggers (we've used his work several times as the centerpiece for our Friday roundtable chats between personal finance luminaries), he actually joins us today in the basement to help you become a wiser, stronger, and hopefully wealthier Stacker. In our headline segment, one saver says that he saved too much money into his 401k retirement plan. Huh? How does that even make sense? We'll chat about how to best save for retirement and also challenge you to think about how you save...and not just about the amount you're saving. We'll hear from a Stacker in need as well AND of course, save time for Doug's trivia question that you'll be talking about all day long. FULL SHOW NOTES: https://stackingbenjamins.com/money-and-philosophy-1546 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Insurance is a topic we all often avoid, with HUGE consequences. When disaster strikes we have either the wrong coverage or none at all. That's why we decided today to have some fun talking about how making better insurance decisions can truly improve your life. You may find yourself skipping down your street because you've either 1) saved money or 2) found better coverages for your situation. We'll chat about: Big picture about using the stuff you buy (ensuring that the purchase is actually "worth it"). How much insurance is "enough" When you can skip the insurance altogether Working with insurance brokers Adding riders to your policies Long term care...the mother of all insurance problems Pet insurance ...and LOTS more. FULL SHOW NOTES: https://stackingbenjamins.com/finding-better-insurance-1545 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's special episode, Joe and Paula Pant (AffordAnything) dive behind the scenes to share key learnings from the Craft & Commerce conference in Boise, Idaho. Recording live from the Kit studios in downtown Boise, they share lessons learned about serving audiences, fighting fear, breaking through business insecurity, and much, much more. It's a wide-ranging discussion where you'll see behind-the-scenes of both brands, and hear about how two creators learn, build, and grow. You'll learn lots of takeaways about your own career, life, and (if you're an entrepreneur) brand that you can apply. FULL SHOW NOTES: https://stackingbenjamins.com/live-craft-and-commerce-conference-1544 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do you do to diffuse the retirement time bomb? The government has a plan, and you won't like it. Joe was the emcee recently for maybe the biggest name in tax planning -- Ed Slott -- and his book launch event. We're replaying as our mentor segment today Joe's interview with Ed from that event because there are so many "a-ha" moments and good direction toward ensuring that your tax time bomb doesn't go off all over your retirement. In our headline, we talk about interest rates and the financial markets. How do you avoid chasing interest rates and instead focus on the big picture? Doug and OG dive into this topic. Plus, we take a call from Nicole, who wonders about her husband's stock options. We talk options, restricted shares, and planning. How do you ensure that you don't overpay taxes on these incentives but at the same time don't end up holding on to worthless options or with an underdiversified portfolio. This type of planning can be messy, so today we help you unwind it all. Of course, Doug shares his trivia and much, much more! FULL SHOW NOTES: Add show notes url here. Be sure to please include https://www at the beginning of the show notes url that makes it clickable on YouTube Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is there anything worse than someone who brags about how much money they make? Many of us would say, "No." On the other hand how many people wish someone would be more transparent about how much they make so that we can emulate them better and maybe earn more ourselves? Today we cover that in the final installment of our greatest hits episode series. We're back next week with new shows! Here are the original show notes from December 10th, 2021: https://www.stackingbenjamins.com/roundtable-1127/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's show...what skill do you need to lead a group of people toward real estate success? Leadership! And man, do we have a leader here to teach you that skill...REMAX Co-founder, Dave Liniger. In our headlines, we chat about the state of airbnbs and if guests get the warm and fuzzies when they walk in. Plus, we’ll answer a call to Ruth's Rotary phone from Aimsley who wants to avoid being over-leveraged, under-leveraged or inter-leveraged-we've got answers. And of course, Neighbor Doug will pop in later with the property pop quiz. Have a question for the show? Head to StackingDeeds.net/voicemail Subscribe to the new show wherever you're listening to today's episode! Just type "Stacking Deeds" into your search function so you catch all of the latest shows the day they arrive (every Tuesday). Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Whether you're a current leader or aspiring to become one, today's leader, Rachael Robertson, has a story you'll need to hear. Tasked with leading an Australian team in Antarctica, Robertson had to make quick, decisive decisions in an environment where nobody was allowed to find refuge. Everyone had to find a way to work together immediately and without fail. How did she do it? You'll hear today how the employment of one simple (but not easy) technique helped her not only maintain control but help her group thrive in the harshest of environments. Of course, as always, this greatest hits episode also includes a headline, Doug's trivia question, and more. For details on those, here are the original show notes: Being Liked Is Overrated (with Rachael Robertson). Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you listen to the news (or see the carnage around you), you know that recessions are a time of hurt. Companies downsize or go bankrupt. People lose their jobs, their homes, and in a stock market decline, their ability to meet goals. But are recessions actually good for us? One recent financial piece says that they are, and our collaborator and friend Doc G at our award-winning sister show, Earn & Invest, dives into it today. He's asked two people from his community plus Joe Saul-Sehy to a panel discussing the possibility that just maybe...behind all of the tears and horror, a recession might be healthy. Find the original show notes here: https://www.earnandinvest.com/episodes-8/are-recessions-good-for-you Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever look at yourself in the mirror? Of course, you have! How often have you had to tell that person looking back at you to get out of the way? If you’re like us, A TON. Mel Robbins discovered that one simple gesture in the morning can make all the difference in our decisions. She’ll share details of her own journey to success after financial hardship and how five seconds and high-fives changed her outlook. High fives aren’t just for big accomplishments or a way to communicate with friends. You can (and should) give yourself a high five every day for all the successes in your life, no matter how insignificant they may seem. Mel dives into the science behind how these small habits changed her life and how they can change yours, too. We are back teaching you about annuities during our headline, and one annuity company is pleading to independent financial advisors to give their products another shot. Annuities aren’t always painted in the best light, and we’ll hear what this company is doing to change that. During our Magnify Money voicemail, Roy wants to pick Joe and OG’s brains about their asset allocation. And, of course, we’ll include some of Doug’s trivia. This show originally aired in September of 2021, so please ignore any mention of current events. You can find the original show notes here: How To Get Out Of Your Own Way With One Simple Tool (with Mel Robbins). Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is the secret to investment success all about making your decisions as if you were a 50-year-old woman? We tackle that take on today's roundtable discussion. We're joined by one of the best voices who gives investing advice online, Brian Feroldi. He's joined by the lady who knows all about making wise investing decisions, no matter your age, Paula Pant. And finally, we also feature the advice of our in-house financial planner (who happens to have the temperament of a 50-year-old woman), OG. In the second half, brought to you by DepositAccounts.com, we continue down the list of how to win by investing like a 50-year-old woman. And, finally, be sure to stick around for Doug's sky-high stock-institution trivia. It will surprise you! FULL SHOW NOTES: https://stackingbenjamins.com/invest-smarter-think-like-a-50-year-old-woman-1537 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 During our conversation, you'll hear us mention: Sticking to your investment plan, even in times of market correction. Why "this time is different" is a dangerous mindset. Weighing the long-term risk-reward relationship. The benefit of indexing. Investing according to your time horizon and risk tolerance. The fallacy of trying to time the market. Dollar-cost averaging. How to resist the temptation to tinker with your investments. How to trick yourself from reacting to every piece of news. How to avoid FOMO. Why you shouldn't care about what others think. Stop comparing yourself to others. Allowing yourself to allocate a small amount of your portfolio to taking outsized risks. Investing in individual stocks if it works for you. Allocating a limited amount of time to making investment decisions. How to distinguish between sound advice and not-so-reputable salespeople. Use good judgment when deciding whose advice to follow. Finding the investing style that works for you. Learning from failure. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Time to revolt! Tired of thinking everyone else is in control when it comes to your money? The grocery store, utilities, retirement plans and their fee structures...everyone wants a piece of you, don't they? Well, today, that all changes. We're burning down ideas like high-interest debt (or debt at all), kids eating your entire budget, needing a million dollars to retire, and other tired ideas. We'll swap these and other ideas out for useable tips and ideas to help you revolt and build your own financial freedom. Our headline today features a top economist who says the idea of retiring with a million is too much. You can retire on much, much less. We'll share why we agree today, but do you really want less? Our TikTok minute is about budgets. Who can afford the fresh produce area of a grocery store? The Better Call Saul... Sehy and OG segment features Dave, who wonders about credit card reward points. Should he begin taking advantage of them? FULL SHOW NOTES: https://stackingbenjamins.com/how-much-do-you-need-to-retire-1536 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Do you think, "I've made it once I reach financial independence?" Douglas Tsoi has been "retired" for over ten years and will tell you, "Not even close." For all of us, a new journey begins once we reach financial independence. What does this look like? How can we prepare? Today, Douglas sits down with Joe Saul-Sehy to dive into the five stages we all experience after reaching what many think of as the finish line. In short, we'll discuss: The fallacy of "I'm done" The reason why people are afraid to retire, even though they may say otherwise The darkness phase of "is this all there is?" and how to fight it The joy of finally realizing that, after the emotional journey, you can flip into a new, gratifying state. In our headline, we'll share a story about two executives in court because their investment scheme was "built on lies." This company promised eight percent returns without volatility. What's wrong with that? We'll walk through: How companies make money and why volatility is always EXPECTED with an eight percent return. Historical returns for asset classes, including the much-maligned international and emerging markets asset classes. Will they ever outperform again? We'll share several ways people try to even out returns to ATTEMPT, including what these alleged scammers said they could do (and couldn't). But that's not all. Of course, we'll also share Doug's amazing Formula One trivia question and much, much more. FULL SHOWNOTES: https://www.stackingbenjamins.com/emotional-stages-after-financial-independence-douglas-tsoi Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What are the biggest fifteen items on most budgets that can derail your spending plan? One blogger, our friend Allison Baggerly at InspiredBudgets.com, made a list. Today we use that list as the basis of a game show episode! Paula Pant (AffordAnything), Doc G. (Earn & Invest) and our own OG go head-to-head in a match to figure out which items made Allison's list. The best part? Even when their guesses are wrong, they bring up MANY budget busters that can help all of us do a better job fixing the holes in our spending plan. Topics we cover: Gifts Taxes Auto maintenance Pet care Holiday spending Medical deductibles/costs ...and much more. We also share MANY solutions to plug the holes in your budget. AND if that weren't enough, we pause at the halfway point of our conversation for our normal trivia competition (a competition inside of a competition? Meta!) FULL SHOW NOTES: https://stackingbenjamins.com/budget-gotchas-1534 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Even if you only have $500 in your emergency fund, today we reveal why having this money in the right place can yield BIG dividends. If you have your $500 in an account paying the average rate, you'll make around $2.50 in interest per year. Yet, by moving these Benjamins to a well-structured emergency fund, you could earn around $22.50. Doesn't sound like much? Assuming this takes 30 minutes, we're talking about earning $40 an hour! That's a GREAT rate of return on your time invested. Episode Overview Why Your Emergency Fund Matters More Than Ever: Ever wondered where to stash your emergency fund for the greatest benefit? With rising interest rates, it’s a discussion worth your time. We’ll cover: How much should you keep in your emergency fund? Avoiding common pitfalls. Understanding the differences between money market accounts, high-yield savings accounts, and other options. And yes, we clarify all this mumbo-jumbo so you can actually understand it! (What are YOUR thoughts on emergency funds? Share with us on Instagram or on Facebook!) Segment Highlights: TikTok Minute: What’s “guy math”? We’ll dive into this fun trend and how it compares to “girl math.” This guy applies girl math to his tool collection. What could go wrong? New Segment Debut: Sometimes, online advice needs a second opinion. Hear OG’s take on some questionable financial tips. Today, we open with Sammie, who is asking for help with her 401k. As you can imagine, any time you ask for advice on the internet, it goes downhill quickly from there. If you see horrible advice in a financial forum, send it to us! (joe at stacking benjamins dot com) Doug’s Trivia: Test your knowledge with Doug’s latest trivia question and much more! Today, he dives into Federal holiday trivia to celebrate Juneteenth. Join the Community: For deeper dives, curated links, and exclusive discussions, subscribe to our newsletter, The 201. Join the Stacking Benjamins community and let’s achieve financial success together! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Tax planning in June? Of course! Why would you wait until next year, when you can't make ANY financial moves that save you money, to start figuring out how to cut your tax bill? Right now, at nearly the halfway point of the year, we'll dive into how to understand your taxes and make cuts with our tax planning mentor, Hannah Cole. Hannah will walk us through tax savings ideas for everyone, and then we'll focus on those people who have either started a side hustle or who are entrepreneurs and share some great tips for business owners. Even if you're just dreaming about having a business or "working for the man," we've got you covered. Plus, in our headline segment, two brothers woke up one day this spring and found themselves disinherited, losing out on approximately one million dollars! How did that happen? It could have all been avoided, and YOU can avoid this problem too. We'll walk you through HOW to make sure your beneficiaries receive the funds you've decided should go to them. We'll also explain how wills and trusts work, and get you started toward building a better "estate plan." Of course, Doug brings his awesome trivia challenge AND we answer a question from a Stacker in need. FULL SHOW NOTES: https://stackingbenjamins.com/tax-planning-year-round-1532 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How are you preparing for retirement? Have you looked at all of the dimensions to ensure you have a successful, long runway of money always available? On today's special roundtable episode, we dive into a piece that claims there are seven things you need to do in order to be prepared for retirement. Joining us are: Don McDonald from the Talking Real Money podcast, Paula Pant from Afford Anything, and OG. In the second half of the show, sponsored by DepositAccounts.com, we dive into risk mitigation, the importance of maintaining adequate cash reserves while in retirement, and keeping a historical context of current events. Be sure to stick around for the yearlong trivia competition with Doug's baseball-themed trivia. FULL SHOW NOTES: https://stackingbenjamins.com/moves-to-make-before-retirement-1531 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

There’s another lawsuit brewing in the world of retirement planning. This time, participants in a 401(k) plan in California are raising concerns about how Qualcomm is handling the money forfeited when employees don’t complete their vesting schedules. Vesting schedule? What’s that all about? Today, we'll break down everything you need to know about vesting schedules, so you can navigate your job benefits with confidence. Whether you’re dealing with a vesting cliff or a staggered vesting schedule, we’ve got you covered. We’ll explain how they work, the taxes involved, how to plan around them, and how to think about any money that isn’t fully yours yet. Plus, for business owners, we'll discuss how to balance keeping talent with implementing vesting schedules. Get ready for a fun and informative session on one of the trickier aspects of financial planning! In our TikTok minute, we’re sharing a clip from Fox News where a contributor predicts what will happen to the stock market if Trump is convicted after his recent trial. Spoiler: He was convicted. Let’s see if his prediction came true and how it might impact your money. We also have a note from a fellow Stacker who thought, "I better call Saul...Sehy & OG." He’s worried about contributing to a Roth IRA because his income is too high. We’ll discuss strategies like backdoor Roth contributions, Roth 401(k) plans, and some of the tricky rules around Roth IRA conversions that can trip people up. And of course, we’ll share a fun trivia question from Doug, sit on the back porch, and so much more! FULL SHOW NOTES: https://stackingbenjamins.com/all-about-vesting-1530 For deeper dives with curated links, topics, and discussions, check out our newsletter, The 201, at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Unlocking the FinTech Disaster: What You Need to Know You might not know it, but a huge number of people have their money trapped in a recent FinTech crisis. When the middleman company Synapse went bankrupt, it froze funds in many popular FinTech apps, including Yotta, a sweepstakes app that makes saving money fun. Will Yotta and other affected FinTech companies be able to return their users' money? What does this mean for the future of FinTech? Is more legislation on the way to prevent this from happening again? While new updates are rolling in daily, we’ll break down what we know and how it impacts your finances. The Fascinating History of Banking Later in the show, we'll dive into the history of banking with our mentor for the day, Paolo Zannoni. Paolo is the deputy chairman of Prada, a historian, and the former head of operations for Goldman Sachs in Russia. He'll reveal that while today's FinTech issues might seem new, they’re part of a repeating historical pattern. Learn how modern banking originated in Pisa, the relationship between banks and credit, how minting money sped up the creation of banks, and how banks and governments have collaborated for centuries. Better Call Saul... Sehy and OG: Setting Savings Goals In our Better Call Saul... Sehy and OG segment, a Stacker mom seeks advice on helping her twenty-year-old daughter set savings goals. The young woman is great at saving but isn’t sure what to save for. We always say, "Begin with the end in mind," but what if you don't know what "the end" looks like? We’ll discuss practical steps to find and set meaningful savings goals. Plus... Don't miss our memorable back porch discussions, Doug's always-entertaining trivia, and much more! Join the Conversation For deeper dives with curated links, topics, and discussions, subscribe to our newsletter, The 201, at stackingbenjamins.com. Enjoy the Show! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why aren't all big-money ballers able to pile up massive stacks of Benjamins? How come some average Joe earners can build significant wealth? On today's special roundtable episode, we dive into a blog post listing the top six reasons people who make big money can't save. One of the Top 100-rated financial planners by Investopedia in 2023, Elaine King, joined us. She's not alone, though. We also feature the creator of the award-winning blog Afford Anything, Paula Pant, and our own resident CFP, OG. In the second half of the conversation, sponsored by DepositAccounts.com, we'll explore the actual benefits of relocating to save money. Stick around for our year-long trivia competition inspired by our special guest, Elaine King's, home country of Peru. FULL SHOW NOTES: https://stackingbenjamins.com/top-six-reasons-youre-not-rich-1528 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Open AI recently survived a brutal firing/rehiring of their CEO and a complete board resignation. In the past, we've heard extensively from Sam Altman, the CEO of Open AI, but we haven't heard from the board. Today we use the words of a board member who's speaking openly for the first time to ponder the question, "Should YOU have a board of directors for your personal financial life?" We parse the words "board of directors" to determine what that really means, and we dive into how these relationships truly work. Should we except "hostile" advice from strangers? Should we consider our friends to be on our board casually? We explore all of these options and more on today's extended Wednesday headline discussion! Of course, we feature a TikTok minute that you won't want to miss as one young woman discovers the true trap that taxes are on your ability to build wealth. Doug also supplies his amazing trivia, and of course, we also answer a call for help from a Stacker who thought, "I'd better call Saul...Sehy and OG." FULL SHOW NOTES: https://stackingbenjamins.com/create-your-board-of-directors-1527 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much of your life is controlled by programming? If you're looking to make more money you have to look at what's blocking you today and transform yourself into an earning machine. It turns out that the key to earning more is right between your ears. Brandon Epstein works with top professionals (athletes, CEOs, entrepreneurs, and high-level executives) to help them achieve even more. You've heard us say many times that great people surround themselves with amazing individuals. Brandon IS that maker of amazing talent. He doesn't create talent. He teaches you how to tap the talent you know is waiting to be deployed. We'll talk about mental blocks, societal programming, identifying those blocks, and how to break free of them on today's podcast. But before that we ask the question, can you trust online reviews? We not only walk through how many of your favorite sites are manipulating their review systems, but we also give you a better method to find and keep talented people around you (or amazing companies that you should work with). We also take a call from a Stacker who wonders how to invest money she's rolled over into her IRA, AND we dive deep on Doug's incredible trivia question. FULL SHOW NOTES: https://stackingbenjamins.com/break-through-mental-blocks-achieve-success-1526 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Maybe the key to achieving happiness doesn't lie in being perfect (financially-speaking). Today we dive deep into striking the balance between channeling your inner Warren Buffett/Jack Bogle/Scrooge McDuck hybrid and channeling your inner Neighbor Doug at the special Summer Slam-Bingo-Ladies Night down at the Sizzler. Joining us on today's special roundtable discussion are: the woman who’ll help you get out of being miserably in debt, award-winning author, Erin Skye Kelly; the guy who helps people be responsible with their future money, the host of the Inspired Money podcast, Andy Wang; and the Scrooge McDuck of this here podcast, OG. In the second half of the show, sponsored by DepositAccounts.com, we dig into how to make money a fun topic. Does being a mega tracker bring you anxiety? If so, maybe you should focus on putting savings first and then spending what's left over. Finally, be sure to stick around for Doug's Benjamin stack-related trivia. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-maintain-happiness-and-be-good-with-money-1524 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today high yield bonds are in the spotlight. A recent Wall Street Journal piece details how you can get eight percent currently in the bond market (which is a rate most stock investors would be happy to lock in). Why may this NOT be a good deal? Well, first you have to understand how bonds work. So, we'll explain that. Second, you'll have to understand the difference between buying a bond fund and a single bond. So, we'll also explain that. Third, we'll have to explain how many investors lose money because they don't understand concepts such as "risk premium." So, happy, we'll show you what that means. It's all things bonds on today's show! But that's not all. Stacker Tom asked a GREAT question in the Stacking Benjamins basement the other day, because it's SUPER complicated. He asks about IRMMA, RMDs, and Medicare. Huh? We LOVE this question because it shows the depth of knowledge you'll need to have to get everything right...but also shows you how you do NOT need to know everything today/right now/immediately. We'll explain all of these terms on today's show (and also illuminate how frustrating the world of financial terms can be during our TikTok minute). FULL SHOW NOTES: https://stackingbenjamins.com/bonds-hidden-risks-1524 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Learning a new language is difficult, and the language of money is no exception. Brian Preston from The Money Guys has created shortcut words and phrases like "financial mutant" to help you focus on what's important and ignore the rest. We'll discuss how to get started, the key moves to reach long-term goals, how to avoid making costly mistakes, and more. Whether you're someone just beginning your journey or a seasoned investor, there's a little something for everyone every time we speak with Brian. In our headline segment, a publication decided to ask AI (Chat GPT) how to beat the stock market. The AI responded with advice, which we'll dive into thoroughly to see if this is the wave of the future. Even better news: beginning this week, we'll track this AI driven portfolio to see if it truly is a better way to invest than a collection of index funds (or just one index). But that's not all. We also answer a question from a Stacker AND Doug shares his amazing trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/become-a-financial-mutant-1523/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome to a very special roundtable edition of the show! On today's show, we're talking about debt, and how to use it (or avoid it) as part of your financial plan. We're joined by Afford Anything's Paula Pant; the host of The Personal Finance Podcast, Andrew Giancola; and the host of the Earn & Invest podcast Doc G! In the second half of the show, sponsored by DepositAccounts.com, we dive into the possible positive effects that having a large amount of debt can have - in terms of constant motivation to make progress. Be sure to stick around for Doug's mind-blowing trivia question about debt. FULL SHOW NOTES: https://stackingbenjamins.com/the-role-of-debt-in-your-financial-plan-1522 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

A recent major media outlet reports that people earning less than $50,000 per year aren't eating at restaurants as often as they did a year ago, and that eating away from home is becoming a trait increasingly more for the wealthy. Today we talk about not only this trend but others as we help you grab a firm hold on your wallet. One of the "big three" expense categories is food cost, and cutting your restaurant tab can be an effective way to sock more money toward financial independence. We'll share tools, strategies, and anecdotes from people who've successfully navigated the restaurant game on today's show. Plus, we share a TikTok minute from one creator who's more than a little worried about homeowners and renters insurance. You'll hear why and how to make better decisions around these policies. Then we look at other communities online and answer random questions we've seen on the web that we think haven't been answered very well. We talk CD rates, driving for DoorDash, and more. FULL SHOW NOTES: https://stackingbenjamins.com/state-of-restaurants-2024-1521 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Nothing says summer more than a trip to your favorite regional theme park. Whether with friends, family, or alone, a trip to a theme park can be either super expensive and tiring or a blast. So that's why our friend from Theme Park Insider, Robert Niles, is BACK to help us all kick off summer on the right foot, spending money wisely on experiences that will be memorable and fun. Not only will he help you save some money, but he'll also share tips on the hottest parks and attractions around the country. We'll talk about food (best food AND deals), thrill rides, family attractions, and more. In our headline, OG and Joe dive into the exchange-traded fund (ETF) craze. People are pouring money into ETFs, but are they doing it wisely? In many cases, no. We'll share how exchange-traded funds work, which types are the best to choose from, and how to avoid getting caught investing in something that sounds great...but truly is not. Of course, we'll also share Doug's trivia question about the biggest stock market drop of all time and FINALLY wrap up our 2024 "Joke Off." It's another day of fun on the Stacking Benjamins show. As always, thanks to our sponsors, and enjoy another show where we're ad-free the ENTIRE second half of the show (as always!). FULL SHOW NOTES: https://stackingbenjamins.com/theme-parks-summer-2024-1520 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

At the end of the day, stacking Benjamins is all about living a better, happier life. But how can you achieve greater happiness while still on your stacking journey? That's what we're all about on today's special, all-about-happiness episode. We're joined by our special guest, host of the Best Interest Podcast, Jesse Cramer; a lady who knows plenty about the intersection of money and happiness, Paula Pant; and our own rainbow and unicorn ray of sunshine, OG! In the second half of our discussion, sponsored by DepositAccounts.com, we dive into more of our favorite ways to improve your happiness. Be sure to stick around for the ongoing year-long trivia competition as Doug brings a rainbow/magical wizard-related trivia question. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-achieve-happiness-1519 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Robinhood seams to always be in the news, and usually not for a good reason. Today Joe and OG discuss Robinhood crypto potentially being sued be the SEC. Crypto still seems to be the wild wild west. Is the SEC trying to put some regulations around crypto but then again isn't that the whole purpose of crypto? Our TikTok is all about following the prospectus and whether Doug starts his fire with those? We answer a question from Stacker, Damon, about whether or not he can help out his kids fund their Roth IRAs? FULL SHOW NOTES: https://www.stackingbenjamins.com/choose-the-right-broker-1518 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Matt Schulz is the PERFECT mentor to teach us how to negotiate because, in his own words, he's not a natural negotiator. Today he proves that you don't have to be a natural to find better deals on your credit card interest rates, prescription, rental cars, hotel rooms, and more. He'll walk us through the common misconceptions around negotiating and help us learn to ask politely for more for ourselves. In our headline segment, small company stocks are struggling to keep up with the S&P 500. Why would someone stay diversified when large companies are doing so well and other stocks are not? We'll walk through the science of diversification and why it's a mistake to bail on underperforming asset classes during down periods. Of course, that's not all. We'll share some of Doug's trivia, answer a question from a Stacker about emergency fund interest rates, and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/negotiate-everything-with-matt-schultz-1517 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Personal finance education in schools is finally getting some attention, but the best financial education starts at home. On today's special prelude-to-summer-vacation roundtable discussion, we're joined by three experts in the field of kids and money. Joining us today are John Lanza from The Art of Allowance podcast, the founder of the Wealthy Kids Investment Club Maya Cobic, and money educator Rob Phelan. In the second half of the show, sponsored by DepositAccounts.com, we talk about how to teach kids about money in the digital world. And you won't want to miss Doug's toothy finance-related trivia question! FULL SHOW NOTES: https://www.stackingbenjamins.com/your-kids-and-money-1516 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

A new CBS report shows that the average person's perception of how much they'll need for retirement has changed dramatically versus four short years ago. Do you think the number is higher or lower? We'll not only share that, but we'll also dive into this idea of calculating the correct amount to save. When is it truly important to begin working on your retirement vision? When should you be more scientific about your overall asset allocation toward your goals, and when does it make sense to just save money? Today we'll share all of those milestones and more as we help you calculate a retirement number that's better geared toward your personal goals AND that's only created when it actually makes sense to have a goal. In our TikTok minute, there are property owners all over the world testing their insurance premiums. We'll share how. We also take a call from Stacker Collin, who wonders which option to take for health insurance (pronounced IN-surance), since it's likely he and his spouse will be working for the same company. Of course, we have some fun out on the back porch talking all things television, and more. FULL SHOW NOTES: https://www.stackingbenjamins.com/calculate-your-retirement-number-1515/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Janesse Torres is a force of nature. She purposefully quit her high-paying job as an engineer because it didn't fit her personality AFTER posting about it on social media. Today she joins us to talk about living your life intentionally, building financial reserves, demanding more from your boss, and if you get "no" as your answer, moving on. As the host of Yo Quiero Dinero and a woman who's a social media/blogging powerhouse, she's used to talking about life as it is, without mincing words. Today you get the full Janesse as she shares how to negotiate, build savings, and more. Plus, in our headline, new legislation should help you find advisors who are trustworthy when it comes to working with your retirement plan money. Will the reality equal the promise? We weigh in on how the legislation works, what we think will happen, and how to plan whether it finally becomes law in September or not. You'll be ready to find better help for your retirement after today's show. Plus we answer a call from Jen, who wonders about HSA plans. Can she move money from her IRA to an HSA? And that's not all....of course, Doug shares some trivia you'll be sharing later with friends and family. On the back porch, we talk about what we've decided for our Friday roundtable shows. Who's going to be the new frequent contributor? Of course, that's just the FIRST episode of our new eight weeks! We've got action packed mentorship from Brian Preston, Robert Niles, humor from Lisa Curry, great feedback from a panel of kids-and-money experts, and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/get-financially-lit-1514 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Join us as we wrap up Greatest Hits Week with a favorite roundtable discussion: What lessons would you share with your younger self? This episode originally aired on November 5, 2021, so please disregard any mention of current events. If you could go back and give your younger self one piece of advice, what would it be? Maybe it’s to take more chances or say adios to the boss that treats you horrible or maybe it’s just to live life to the fullest and not worry about what others think. Today our roundtable discusses a blog piece from Ryan Holiday about mistakes he’s made and advice he would give himself. Caleb Gulliams (Better Wealth), Paula Pant (Afford Anything) and Doc G (Earn & Invest) join our roundtable and talk about advice they’d give their younger self and the mistakes they’ve made. FULL SHOW NOTES: https://www.stackingbenjamins.com/life-lessons-to-younger-self-greatest-hits-1513 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Let's keep Greatest Hits Week rolling with a must-hear episode from our sister show, Stacking Deeds. This show originally aired on November 21, 2023, so please disregard and mention of current events. Do you struggle to ask for more from your contractors, your real estate professional, your stagers, or other help? Do you think you stink at negotiation? Before learning to negotiate, it’s a great idea to get comfortable with asking for more. You can view the original show notes here: Confidence in Negotiation: Asking for More in Real Estate Deals with Dia Bondi (stackingdeeds.net). FULL SHOW NOTES: https://www.stackingbenjamins.com/confidence-in-negotiation-stacking-deeds-greatest-hits-1512 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

t's Hump Day on Greatest Hits Week! Today we're throwing it back to a fan favorite: Joe's 2018 interview with the one-and-only Suze Orman! Please disregard any mention of current events. We’re pulling out all the stops today because we’re talking to a special guest that you may (or may not) have heard of… Suze Orman. We’ll talk all things women and money, mentorship, understanding your investments and financial tools, and more. Plus, during our headlines segment we’re extra packed because we’re delivering three awesome headlines. First: is Robinhood really making MILLIONS by selling out millennials’ user data? One group thinks so. And if that wasn’t enough, in a retirement plan court fight, one retirement fund is fighting back against participants that sued the employer by asking for monetary sanctions against the six employee-plaintiffs and the law firm that represented them. But that’s not all….because we’re also dissecting one piece about Barry White and the estate he left behind. How much of your estate does your girlfriend receive when you’ve been separated from your wife for two decades (but never actually divorced her?)…do we have some news for you… The original show notes are available here: Suze Orman » The Stacking Benjamins Show. FULL SHOW NOTES: https://www.stackingbenjamins.com/suze-orman-greatest-hits-1511 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this current events/community we invite Earn & Invest community member John Neidecker to discuss how to hack retirement by skipping 3 of the 5 stages. We review Richard Himmer's article from Kiplinger. Joe Saul-Sehy joins us as our expert for the episode. This show originally aired February 29, 2024. Please disregard any mention of current events. For the original show notes, visit How to Hack Retirement — Earn & Invest (earnandinvest.com). FULL SHOW NOTES: https://www.stackingbenjamins.com/hack-retirement-greatest-hits-1510 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome, Stacker, to a very special week! We start off our special Greatest Hits Week with a bang! Know those horrible situations where everyone’s fighting at work — or worse, at home? Talk about a horrible investment: being invested in a rotten environment can overshadow even the best portfolio returns. Good news, though. It turns out, there are two types of conflict: the kind that allows us to grow and produces a positive outcome and the kind that’s downright toxic. To help us find a way toward healthy conflict, Gabe Karp joins us. He talks about why it can be hard to see the other side of an argument, how to turn bad conflict into good, and how to move toward a healthier working environment by even maybe fighting more (but in a healthy way). But before that, we speak to Lamine Zarrad from Stellar about credit and the current economy. What happens when interest rates continue to rise and you need a new loan that you can’t afford? Lamine created a company called StellarFI, which was built to help people build their credit through paying bills on time. We’ll talk about credit issues, the economic slowdown, and how you can protect yourself. This show originally aired in June of 2022, so please ignore any mention of current events. The original show notes are located here. Are Workplace Clashes Ever Worth It? (with Gabe Karp) » The Stacking Benjamins Show FULL SHOW NOTES: https://www.stackingbenjamins.com/gabe-karp-greatest-hits-1509 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How can you take control of your life instead of life taking control of you? On today's special roundtable episode, we're talking about making the most of your productivity habits. How has your phone robbed you of your productivity? We're joined by Rob Berger of The Dough Roller Money Podcast, founder and CEO of the financial services firm Sensible Money Dana Anspach, and founder of Afford Anything Paula Pant. They'll dive into their top productivity tips. On the second half of the show, we're joined by MetPro's Angelo Poli. He and Joe dive into health and fitness. He breaks down top techniques to improve your wellness. Be sure to stick around for Doug's baseball-themed trivia! FULL SHOW NOTES: https://www.stackingbenjamins.com/better-systems-to-improve-productivity-1508 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Join us today as we dive into the core principles of building a sustainable financial future with marketing professor, author and investor, Scott Galloway. We explore the essential formulas behind his book Algebra of Wealth, discussing purposeful living, effective retirement planning, and the emotional aspects of investing. Our headline today is all about AllianceBernstein 401k lawsuit that was dropped by New York US District Court. During our Better Call Saul-Sehy and OG, we unravel the complexities of early retirement, delving into specific IRS rules for accessing retirement funds. Plus, Doug wraps it all up with some modern history trivia! FULL SHOW NOTES: https://www.stackingbenjamins.com/investing-with-a-life-mission-1507 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today we're all about the factors to help you build a better investment portfolio. Joe and OG break down their thoughts as they dole out their top five building blocks to constructing a better portfolio. Be sure to bookmark this evergreen episode, as it contains universal truths that will help you in the years to come! In our headlines, we talk about what's the best way to prepare for unexpected financial shocks, and when to get started (spoiler alert: how about now?). We dive deeper into how to protect your downside in the event of black swan events. Our TikTok Minute is all about how to get 90% of the way to your health goals by using one simple trick. Stick around for Doug's US currency history-related trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/top-five-investment-building-blocks-1506 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Let's talk about what it takes to become a millionaire in today's day and age. We are thrilled to bring you a special roundtable episode with three outstanding contributors: we welcome CEO of BFG Financial Advisors, CFP® Eric Brotman; the force behind the website Yes, I am Cheap, Sandy Smith, and our resident doctor and host of the Earn & Invest podcast, Doc G. In the first half of the discussion, we cover two of the primary ways to reach millionaire status: saver/investor, and passion-based activities (starting a business, reaching celebrity status, etc.) In the second half of our discussion, brought to you by DepositAccounts.com, our roundtable dives into 2 more ways that people achieve millionaire status: the company-climber path and the virtuoso path. Plus, our year-long trivia game continues, with none of our roundtable regulars. Which sit-in will bring home the W for Paula, Len, or OG? Tune in to find out! FULL SHOW NOTES: https://www.stackingbenjamins.com/4-paths-to-become-a-millionaire-1505 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today's episode is all about a very important, topic that's sure to arouse interest at personal finance get togethers: risk management. Specifically, Joe and OG jump into their Top 5 risks that people don't think about enough - and what you should do ahead of time. In our headline segment, we dive into a popular personal finance website's piece about what to keep in mind when aging. Our TikTok Minute features unfathomable consequences that one might experience if living near a certain sporting location. And finally, Doug brings it all home with his trivia that's loosely related to insurance (but not really). Classic Doug! FULL SHOW NOTES: https://www.stackingbenjamins.com/all-about-better-insurance-choices-1504 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you've ever wondered if there's more in life and your career waiting for you than your current job, then today's mentor is someone you want to listen to! On today's show, we welcome Michael Balter to the basement to discuss his career path and how he pivoted in a big way! In our headline segment, we see some shocking (eye-roll) news about one store's credit card and how they are going to make up the lost revenue that they can charge in late fees. OG is not surprised. And, finally, stick around for Doug's trivia loosely tied to April 15th. It's a stretch, but he's going with it. FULL SHOW NOTES: https://www.stackingbenjamins.com/career-pivots-for-the-win-1503 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you know when the time is right to walk away from a career? Do you even want to? Can you afford to? Our roundtable discussion centers around thinking about retirement and how to prepare yourself financially so you can stay retired. We welcome Founder/President of Capital City Wealth Management, CFP® Benjamin Brandt, to join Paula Pant and Len Penzo. How do you factor paying for health insurance into your early retirement planning? What about debt payments? When you retire, there will be greater spending in some areas that you may not think about while still working. FULL SHOW NOTES: https://www.stackingbenjamins.com/why-you-should-retire-by-62-1502 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Did you recently come into some money? Are you expecting to in the near future? How have you treated "found money" in the past? With millions of Americans receiving their income tax refund, today we discuss what smart Stackers do with "found" money. Not only that, but we also dive deeper into tips for how to decide ahead of time what you will do with any windfalls that come your way throughout the year, so you don't have to worry about blowing investing the entire amount on a brand new El Camino. Be sure to stick around for Doug's this-day-in-baseball-history-themed trivia question! FULL SHOW NOTES: https://www.stackingbenjamins.com/what-to-do-with-your-tax-refund-1501 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How can simply being kind (and using math) bring more Benjamins into your life? Today we explore the topic of how changing your outlook towards others can attract more abundance and wealth in life when Joe sits down with our mentor, the brilliant James Rhee, MIT professor and author of the hit book red helicopter: a parable for our times: lead change with kindness (plus a little math). In our headline, we talk about the recent cutback in spending on lavish weddings, and how much is too much to expect to spend on your nuptials? Plus, how do you get out of budget for attending a wedding you've been invited to? Stick around for Doug's wandering trivia! You're sure to not feel any older after his knowledge! FULL SHOW NOTES: https://www.stackingbenjamins.com/kindness-math-and-benjamins-1500 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Today's episode is our 1499th episode! On today's celebratory show, we dive into some of your success stories! Plus, ever wonder how you achieve anything big in life? Just get started! On today's episode you'll get a behind the scenes look at the evolution of Stacking Benjamins. We go into what lessons we've learned along the way and how we strive to keep improving. Stacker Christine from Seattle calls in to share her story, and how listening to the show inspired her to change her social circles and the conversations she was having with others. We dive into best practices for building your business as an entrepreneur and how to build your network and reputation. Stacker Derek calls in to express his gratitude for the show and all of the regular contributors. Lambo calls in to share how listening to and learning from the show has helped him improve his financial life. Stacker Billy from San Francisco called in to give a shoutout to us and express gratitude for the help in making positive changes in his financial life. FULL SHOW NOTES: https://www.stackingbenjamins.com/past-present-future-of-sb-episode-1499-celebration Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

The word is out on using low-cost investments over complex Wall Street strategies (and if you don't believe us, we'll quote SIGNIFICANT studies on today's show). Yet, new expensive products are built every day promising better/faster/more wealth. What do you need to know to simplify your strategy and stay the course? In today's headline segment we'll dive into diversification and keeping your portfolio simple. We'll share why it's important to question more complex strategies, and discuss solutions that wealthy investors truly are using to increase future income streams while keeping things low cost. We'll also shine a light on a popular investment manager who's working directly opposite the trend that we're suggesting, Cathie Wood of ARK Investments. We'll share the wild ride up and our thoughts on her recent issues and disastrous returns. We'll also take a call from James, wondering about ABLE accounts. These are wonderful tools for people with special needs who are diagnosed early in life, and can help individuals avoid significant taxes. How do they work? What do you need to know? We'll share. Of course, we'll also dive into Doug's amazing trivia question of the day, which shines a light on a high cost investment option: hedge funds...while saving time for a TikTok minute you won't want to miss. FULL SHOW NOTES: https://www.stackingbenjamins.com/all-about-fees-and-you-1498 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Busy does not equal productive. In fact, how often have you watched as someone who was too busy to reach the important items on their mile-long list? Sadly, we're addicted to the to-do list but not addicted enough to processes that actually increase our happiness, creativity, or effectiveness. True productivity begins with CALM, according to today's mentor, Laura Martin. She created the productivity expert role at Google, and joins us today to share hints and tips to make you not only more relaxed, but also a fountain of productivity, no matter what you want to do. Beyond that, we have an amazing headline, Joe & OG share the biggest laughs of their lives, and Doug FINALLY gives maybe his best advice ever. Oh, and former President Barack Obama stops by. FULL SHOW NOTES: https://www.stackingbenjamins.com/more-productivity-less-guilt-1497 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

One of the most frustrating moments in any investor or saver's life is when you figure out that you fell prey to a "gotcha" you didn't expect and either lose money, opportunity, or both. Even if your favorite financial tool, strategy or advisor doesn't mean to inflict a "gotcha" on you, because we often don't know what we don't know, we use tools or people inefficiently, causing damage to ourselves we didn't expect. Today we talk about intended and unintended "gotchas" in financial products with three people who know and who've seen many problems firsthand. All of them are Certified Financial Planners, and all three are hosts of great podcasts. Shannah Game (Everyone's Talkin' Money), Roger Whitney (Retirement Answer Man), and our very own OG debate and discuss many of the nuanced (and sometimes not-so-nuanced) "gotchas" in investments, insurances, financial planning, and more. That's not all though. Of course we take a break halfway through for our weekly trivia contest between our contributors. Today? Doug's building bridges! You'll have to hear it yourself and maybe guess your answer. Can you beat our contestants? FULL SHOW NOTES: https://www.stackingbenjamins.com/person-finance-gotchas-1496 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

If you plan on living a long life (and who doesn't want that?), you'll need to create over thirty years' worth of cash flow. Studies show that the average person wants to retire at the "normal" age of mid-60s but also plans to live to reach the century mark. If that's you, you're in luck because today we're joined by the CFO of one of the country's greatest comedy clubs and a guy who's a professional comedian himself, Bob Wheeler. Bob joins the guys for the entire show to talk about longevity and planning and maybe share a few laughs. We also spend some time talking about two controversial approaches to paying down debt and banking: Velocity banking and Infinite banking. We describe both concepts and share the good, bad, and unfortunately, the ugly. That's not all. Doug is partying hard because it's the anniversary of the date the shoelace was patented! There's nothing like a basement-based party with a top comedian, your money jokes, and discussions of annuities, longevity, and getting started. FULL SHOW NOTES: https://www.stackingbenjamins.com/make-your-money-last-30-years-bob-wheeler-1495 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Our mentor today is one of the foremost thinkers and practitioners in the financial planning space. Peter Mallouk joins us to dispel the myth that the stock market is like the stock market, that the bond market is still dangerous (a year later), that AI is coming for our jobs, that you'll find safety in a savings account, and that gold is a great investment. It's a dynamic discussion with the man who wrote a financial book with Tony Robbins a few years ago, who owns the Kansas City Royals baseball team, and who is one of the top financial planners in the country. In our headline segment, we do something we often don't engage in: philosophy. But today, philosophical discussion meets behavioral finance (much more our strong suit), in a Wall Street Journal piece about passive investing and capitalism. Is passive investing killing the stock market, and then by extension, capitalism? While we probably won't solve the world's problems or "fix" the stock market, we will discuss the basics of passive investing (positives and negatives), the problem of (and also the advantages in) not knowing what's going on with the companies in which you've invested, and the importance of diversification, balanced portfolios, and avoiding recency bias. Of course, Doug shares a trivia question fresh out of Scotland. He'll use an important marker of today's date in history (Robert the Bruce's birthday) to shine the light on one of the most iconic pieces of real estate in the world, Robert's castle. We also help a Stacker who said, "I'd better call Saul...Sehy and OG!" He wonders about becoming a financial planner when you don't have a college degree. Is it more difficult to gain experience? FULL SHOW NOTES: https://www.stackingbenjamins.com/getting-your-financial-plan-right-1494 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is the battle between index funds and actively managed funds finally over? Total assets invested in index funds and ETFs recently passed assets invested in active funds for the first time ever. But is going all index funds the right move for you? Joining us is CFP and President of Bona Fide Wealth, Douglas Boneparthe. Also joining us is Crystal Hammond, host of our sister show, Stacking Deeds. And finally joining us from his bunker deep under Los Angeles is the creator of the award-winning blog lenpenzo.com, Len Penzo. We dive into the difference between active and passive funds, break down the history of each, and pontificate on where we think the investment world is heading. Plus, what are the risks of cap-weighted index funds? In the second half of the show, sponsored by DepositAccounts.com, we dive into the industry secrets and their smoke-and-mirrors tricks. Be sure to stick around for our ongoing year-long trivia competition. Doug brings us some diminutive French leader-themed trivia. You won't want to miss it! FULL SHOW NOTES: https://www.stackingbenjamins.com/active-vs-passive-fund-debate-1493 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Grace Puma and Christiana Smith Shi have been where you're trying to go. Puma was the COO of Pepsico, one of the largest brands on earth, and Smith Shi was the President of Nike Consumer Direct after over twenty years at a little consulting firm called McKinsey. Today they join us in the basement to help you reimagine your career and focus on the big picture while still doing a great job at the position you're holding now. How can you be both strategic AND focused? They'll share. Plus, they'll talk about the value of changing jobs (or employers), how to polish your resume, and how to lead yourself through organizations to find the top. In our headline segment we're visited by another star....this one in the tax planning world. Ed Slott is back, and he's fired up about your retirement accounts. His take: stop saving into pre-tax 401k plans and IRAs! Why? Here during tax season Ed joins us to dive into what we SHOULD be focusing on this tax season....and reminding us what we should ignore. But that's not all. We also answer a call for help from a Stacker who's wondering about the latest Robinhood promotion. Even though we're not fans of the company, should he take the free money? Of course, we also save time for Doug's trivia question, and much, much more. FULL SHOW NOTES: https://www.stackingbenjamins.com/career-forward-grace-puma-christiana-smith-shi-1492 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Anne Lester knows money. She helped develop target date mutual funds at JP Morgan, headed retirement programs, and knew her stuff. But Anne, like many of us, is a spender at heart and has had to trick herself into great saving habits. How? We talk about the basics, which do NOT include skipping lattes or shaming yourself into saving more money. In fact, the truth about saving more money is hiding in plain site, and we dive in so you can finally begin or accelerate your journey TODAY. Before that, though, in our headline segment, the United State government is cracking down on credit card late fees. The Biden administration has passed a cap on fees at eight dollars, and has also foreshadowed that overdraft and other bank fees may not be far behind. Is this legislation going to help you save more money? We'll dive into what we love, don't love, and what we're cautiously optimistic about, assuming that YOU take action on your plan and tighten up your banking practices. That's not all. We also answer a question from a Stacker who said, "We'd better call Saul...Sehy and OG for help!" Of course, there's Doug's trivia segment as well, and much, much more. FULL SHOW NOTES: https://www.stackingbenjamins.com/mastering-financial-basics-anne-lester-1491 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Admittedly, we finance nerds tend to obsess a lot over topics that may or may not be super relevant to the general public. But what are some things that are overrated in personal finance? That's what our panel dives into in this special roundtable discussion. Joining us we welcome back financial educator and author, Brian Feroldi. He joins Paula Pant, creator of Afford Anything, and our resident CFP®, OG. On the second half of our discussion, sponsored by DepositAccounts.com, we debate more of what the most overrated concepts in personal finance are. And finally, our year-long trivia contest continues as Neighbor Doug whips out some charity-related trivia.  FULL SHOW NOTES: https://www.stackingbenjamins.com/the-most-overrated-ideas-concepts-and-beliefs-about-money Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Stackers in the wild are amazing creatures. We're quitting the job we don't care about and spend more time in our community because we've built emergency funds (Mike and Melissa share this story). We're becoming enrolled agents, a job that many can use as a side hustle to pay down debt, retire early, or build a better life (Jordan shares his tale passing these three tests). We're retiring early because we did the work and created surround sound to bounce ideas off of other people (Chris shares how he left his job at age 50). There are so many cool people all around you doing awesome things and today we share just THREE stories from YOU. But first we have a pair of disturbing headlines. One says the market is poised to continue upward, while the other cautions that we're nearly 100% certainly headed for a downturn. The problem? These two pieces were both found on the SAME reputable website, one right under the other! Huh?!? So, which is correct? We talk about both predictions and what we think YOU should do when you read either of these prognostications. FULL SHOW NOTES: https://www.stackingbenjamins.com/stacker-community-episode-taxes-fire-flexibility-1489 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Kurt Long used to launch rockets for NASA, but lately, he's been worried about your money (and your health). Kurt is the co-founder and CEO of security and privacy firm BUNKR, and has worked with some of the largest financial and healthcare institutions to keep your data private. We discuss where the biggest threats are coming from, what to ask advisors, what you should do to protect your health care records, and more. By the end of today's episode, you should have a clear idea of when your financial information is at risk and when you're safe. But before that we dive into a headline about timeshare exit fraud. If you've ever heard the commercials offering to help you get rid of your timeshare, you may have some idea what a huge industry it's become, and also now full of scammers trying to "help" you...or maybe just help themselves to your money. We talk timeshares, scams to get you IN and unfortunately, now also scams to get you out. How do you steer clear of all of this? We'll share ideas Of course, we'll also take a question from a Stacker who said, "I'd better call Saul....Sehy and OG!" and we leave time for Doug's trivia question, that we're sure you'll be sharing around the virtual watercooler later today. Our 1500th episode is coming! If you've changed your financial life at all because of the show or the SB community, call in and celebrate with us. Tell us how you've made some positive changes and we'll help motivate other Stackers to get rolling on their financial plans! Go to http://stackingbenjamins.com/voicemail and leave us a message sharing something you've done as a result of the show. Thanks for helping us build this coming episode! FULL SHOW NOTES: https://www.stackingbenjamins.com/secure-your-life-kurt-long-1488 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What role does spending money play in your life: as a tool to live a better life or a yardstick of status to measure yourself against others? Our roundtable discussion centers around this, as we're lucky to be joined by the dynamic duo Kitty and Piggy from the award-winning Bitches Get Riches podcast and blog. They join up with OG and Len Penzo to form the roundtable for this epic episode. Joe's mom's cousin Diania Merriam, founder of the EconoMe Conference, takes over MC duties for Neighbor Doug. In the second half of the roundtable discussion, sponsored by DepositAccounts.com, we dig into each of our contributors' favorite entry on Morgan Housel's list. Stick around for the next installment of our year-long trivia contest. Diania brings a Gillian's Island-themed trivia to our panel. Will the Bitches use their advantage in numbers to take home the W for Paula? Will Len's first-hand knowledge of Gillian's Island, having actually been around for the pilot episode, give him the upper hand, or will OG use his superior financial planning skills to bring home the W? FULL SHOW NOTES: https://www.stackingbenjamins.com/kitty-piggy-roundtable-1487 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Were so worried about the Benjamins, the job, the success ladder, and getting "the things" that sometimes we forget to live. Guy Kawasaki was in the room when the iconic Apple "Think Different" campaign was created. He believes that "Think Different" isn't enough today. In his words, "You can be different and still suck." It's time for a higher target, and that target is "remarkable." But how do you get there? We'll detail everyting from the findings of Carol Dweck to the work of Jane Goodall to parse what "remarkable" truly means. In Guy Kawasaki's world, it means surfing. It means questioning your beliefs. It means learning how to ask better questions. Before that we cover a disturbing headline: FinTech company Chime and company-with-a-reputation-of-dishonesty Robinhood are better regarded than products which compete against them offered by big names like Vanguard and Fidelity. Why are younger investors and savers trusting these names over the heavyweights? That's good news, right? Maybe. We'll share what we think this means and also what you should do about it when thinking about where to park your hard-won dollars. Of course, we'll also take a question from a Stacker in need AND share Doug's trivia question! On the back porch, we also announce some new meetup dates. Come out and join us! FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-live-your-best-life-best-self-guy-kawasaki-1486 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

So many new businesses start every year, only to fail weeks or months later. Sadly, many of the missteps these would-be business owners made could have been presented if they'd followed some fairly simple steps. CPA Michele Cagan not only owns her own small business, she counsels many business owners with their taxes and their business plans. She joins us today to share some of the most essential nuggets new business owners and side hustlers need to know, from her new book, Starting a Business 101. In our headline segment, Capital One has acquired Discover. What does this mean for Discover and Capital One cardholders and clients? We'll dive into all of the details and what experts are predicting will happen to the benefits cardholders of each company can expect. Good news no matter whether you're a Discover or Capital One customer...experts seem to believe things are looking up across the board. Of course, we'll also share a TikTok minute AND discuss backdoor Roth IRAs, mega-backdoor Roth IRAs (aka - "Doug's Mom IRAs"), and much, much more. Of course, we save time to wander out to the back porch and share our favorite films and television shows...and others we don't care for so much. FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-start-a-business-101-michele-cagan-1485 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We round out Rewind Week with an episode from The Earn & Invest Podcast. This is a current events/community Thursday episode featuring an Earn & Invest community member Ian Kist. We are also joined by Joe Saul-Sehy from The Stacking Benjamins Podcast. Today we discuss current articles about Crypto and Indexing that seem to be diametrically opposed. Who is right? This show originally aired on January 25, 2024, so ignore any mention of current events. To see the original show notes, visit Community Episode: Crypto vs S&P 500 Index Smackdown — Earn & Invest (earnandinvest.com). Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We continue Rewind Week with an episode where interviews Jason Tartick. How happy are you, truly, with your job and life? Many people go through the motions in a career they don’t like, never taking the leap to find something they actually enjoy. The average life expectancy is 79 years, so here’s a question: how many of those years are you willing to waste doing something you don’t love? Jason Tartick is well known for being on The Bachelorette but his story is much deeper than what we saw on TV. He was secretly having panic attacks at work as a banker and was stressed beyond belief. Instead of digging deep to find the reason why, he initially tried to mask and ignore the emotions. He’s here today to share his story and how he ultimately restarted his life and career to do what he loves. During our headline segment, Rita Assaf from Fidelity Investments joins the fun to share the results of Fidelity’s State of Retirement Planning survey. She shares the biggest concerns on investors’ minds and the impacts the pandemic has had on our financial confidence. Later, we’ll also answer Kevin’s question about an excess Roth IRA contribution. And, of course, Doug will share his amazing trivia. This show originally aired on April 6, 2022, so ignore any mention of current events. To see the original show notes, visit When Do You Reboot Everything? (with Jason Tartick) » The Stacking Benjamins Show. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We kick off our Rewind Week with an episode from our sister show, Stacking Deeds. Asking questions is the key to making connections, and today we connect with top Manhattan real estate broker Vickey Barron! She'll teach YOU how to ask the right questions to buy the right properties and build the right team. In our headlines, scams are on the rise....so what are some of the biggest real estate scams? We'll share. And speaking of share...I'll share some trivia that travels coast to coast. This show originally aired on August 15, 2023, so ignore any mention of current events. To see the original show notes, visit The Inquisitive Investor: Vicki Barron on How Asking Questions Elevates Your Real Estate Game (stackingdeeds.net). FULL SHOW NOTES: http://stackingbenjamins.com/sb-rewind-stacking-deeds-vickey-barron-1482 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Over the course of your life, would you prefer to feel special or happy? If you can only choose one in your life, which one would you choose and feel like you made the most of it? That's the topic for our roundtable discussion today. We're joined by our very special guest Dana Anspach, CFP®, RMA®, Kolbe Certified™ Consultant, and Founder & CEO of Sensible Money, LLC. She's joined by our in-house sourpuss OG and Len Penzo, creator of the award-winning blog lenpenzo.com. Our panel discusses whether achieving "happy" or "special" is necessarily an either/or decision, or if there's some middle ground between the two. Joe goes on to clarify that the author's definition of "special" centers around addiction to professional success: addicted to being hardworking, successful, and wealthy. We tackle why many success-focused people are actually "miserably rich." Do you have to sacrifice your happiness in order to achieve professional success, or is there a way to have the best of both worlds? In the second half of the discussion, sponsored by DepositAccounts.com, we dive into how to overcome workaholism, so you avoid being miserable and wealthy. Is shedding materialism in favor of simplicity the secret to maintaining a healthy balance between success and happiness? Stay tuned for Doug's amazing big-money question. Will Dana propel Paula into a 3-way tie for first place or will OG or Len take sole possession of the lead? FULL SHOW NOTES: https://www.stackingbenjamins.com/balancing-success-and-happiness-1481 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What are the most difficult skills you can master to create more Benjamins? Among the top must be "communicating effectively." The term "rainmaker" exists because people who can bring in more connections, networks, and also business into an organization are generally among the highest paid employees. The most valuable people in any organization are those who can simply and effectively share thoughts that move the needle. But that's only at work. Communication is also a huge part of making and keeping friends, building a family, or negotiating with neighbors, contractors, or community members. In short, being a supercommunicator pays in every possible way. That's why Charles Duhigg (bestselling author of The Power of Habit) joins us again to discuss how YOU can communicate more effectively. He'll talk about the different types of conversations people have, techniques to improve your skill when talking with others, and how to find common ground more often so that you can all handle the tasks of the day. But before that, we share a headline about the insurance industry. Things are a-changin', as they say, and it turns out...insurance is pretty boring. But will it always be boring? And what does that have to do with your money anyway? We'll share details on what's happening in the insurance industry and why you might want to evaluate your coverages to decide if it's time to move to better risk management techniques. Of course, we answer a question from a Stacker who thought, "I'd better call Saul....Sehy and OG!" He wonders about dividend paying stocks, taxes, and more. Plus, we'll also crown this podcast with Doug's amazing trivia question, the next round of our 2024 Math Joke Off, and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/charles-duhigg-1480 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Today's takeaways: 1) Check with your insurer to see that you're getting all the discounts possible AND check with other insurers to see if they're more competitive than your current offering. Talk to agents to ensure you have the right amount of coverage as well. 2) Ask, "What type of conversation are we having" before engaging too much in any discussion. Taking just a moment to do so can yield great opportunities. Learn to overshare so that others feel comfortable, and meet the person where THEY are, versus where you want them to be. 3) While dividends are great, a high dividend also means the chances for appreciation lower. If you're in a low tax bracket you may pay little (or no) tax on dividends...but a high dividend paying stock still may not be your friend. Also, if the dividend is really high, check to see if the company is organized as a partnership. If so, that may mean you'll have tax complications, including possible tax on dividends (even inside of an IRA), and additional reporting through a K-1 document...which often arrives very late in the tax season. Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why aren't you making those big strides you're hoping for in your career, personal life, or with your money? Today we talk about the building blocks of success, which contrary to popular belief, isn't being "special" or taking a "big leap." It's getting the little things correct. Dr.'s Resa Lewiss and Adaira Landry join us to dive into tweaking some of the skills they've found can give you the largest boost with the least amount of effort, to increase your income, experience life more, and ultimately not just stack more Benjamins, but stack more worthwhile moments. Before that we share a headline that could save you thousands of dollars in taxes. One popular tax expert looks at the thousands of layoffs recently and finds some lemonade in the job-loss lemons of life. We explore one tax strategy we haven't discussed in a long, long time...and it could be your biggest tax break ever. Of course, we also share a great idea in the TikTok minute, Doug's amazing trivia, and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/micro-changes-for-big-results-1479 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you heard about the new Apple Vision Pro that was recently launched? Are you an early adopter, or are you waiting for the price to be cut and the kinks to be worked out? Here to discuss the new world reality of augmented reality and virtual reality, we're joined by Certified Financial Coach and co-host of the hit couples' finance podcast For Better & Worth, Ericka Young. She is joined by Doc G of the Earn & Invest podcast and our very own OG. Is this amazing new technology worth its $3,500 price tag? Is there room in your budget for it? Or is it a justifiable "I'll figure it out later" type of expense? We discuss the pros and cons of being on the cutting edge, when it's acceptable (or not) to pull the trigger on a big, not-totally-necessary expense. Plus, stick around for our latest installment of Doug's year-long trivia game. Will Doc G make Len proud, will Ericka put Paula Pant on the board, or will OG take this week's prize? In the second half of the show, sponsored by DepositAccounts.com, we dive into why the fact that the Apple headset is so good it is actually a problem. FULL SHOW NOTES: https://www.stackingbenjamins.com/spend-or-save-priorities-ericka-young-1478 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Love is in the air! Today we're talking about relationships with two fantastic people - our guest of honor today is the host of the Optimal Finance Daily podcast and also the woman behind the EconoMe Conference, Diania Merriam. Diania and Joe talk about relationships, money, and that the whole idea of "relationship" doesn't start where many people think it does. We especially focus on money's role in a relationship and how focusing on the wrong aspects of "love" can end up helping out OUT of a relationship instead of getting closer with your "soulmate." Before that we have some fun talking about investing strategies with guest co-host, comedian Paul Ollinger. Paul rides along with Joe, OG, and Doug through a fun discussion on the fact that advisors are getting away from "boring" allocations of exchange traded funds and instead moving to separately managed accounts. What IS a separately managed account and why would an advisor do that? We get NERDY on today's show and shine a light in an area that advisors may not want you to look. Of course, we take a call for help from a Stacker AND Doug regales us with his amazing trivia, which we're sure you'll LOVE. FULL SHOW NOTES: https://www.stackingbenjamins.com/2024-econome-conference-diania-merriam-1477 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Grab some candles and cuddle up with a loved one for this one! It's an epic episode! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Breaking up is hard to do...but what if your money is at stake? You don't want to be in a horrible relationship with a financial advisor that you can't trust, don't like, and who doesn't make your wallet go all a-flutter. That's why we called in Chris Mamula to kick off "relationship week" on the podcast. He's a guy who was anti-advisor for a long time and now IS an advisor. How would HE tell you to break up when you're in a bad relationship? He'll share great tips AND his personal experience from behind the advisory veil on today's show. Plus, in our headline segment, millennials are struggling with credit card debt. How do they begin to dig out? We'll share both strategies and motivators for you, whether you're a millennial or not. Of course, we have a brilliant TikTok minute from a Stacker who's making the most of a Hallmark holiday by making money instead of spending it. If you're spending Valentine's Day working, you'll LOVE this edition... Of course, we'll also share Doug's fantastic trivia question AND Joe's review of Poor Things on the back porch. FULL SHOW NOTES: https://www.stackingbenjamins.com/find-a-financial-advisor-you-love-1476 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you looking for a way to get and keep an edge over your competition? Want to dramatically improve your results and are willing to think big? We're joined by our friend Lacey Langford from the MILMO Show to tackle that subject. She's joined by Len Penzo of the award-winning LenPenzo.com and our very own Drill Sargent, OG. If you're looking to set yourself apart in your field, be sure to tune in as we discuss ways you can achieve an edge. Be bold and take risks, as these are ways to truly learn and put yourself out there. On the second half of our show, sponsored by DepositAccounts.com, we dive deeper into how you can find your edge. Should you cast a wide net when searching for people who will help you achieve your edge, or should you limit your search to just those who have already traveled the same path that you're on? Finally, be sure to stick around for Doug's inheritance-related trivia question! FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-get-ahead-financially-1475 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ah, the distinct smell of tax time. All that sweating...sweating out deductions, college expenses, rental income, and maybe even side-hustle write-offs (what exactly is a write-off again?). There are so many options for software to help you, where do you turn? Today we're diving into the College Investor's annual list of best in class software with Mr. College Investor himself, Robert Farrington. We won't share just ONE choice, but will walk through all of the different areas of your life where you might need one particular program over another. Before that, though, we share a headline about one popular columnist who disappeared last year to write a book, and missed out on all of the ups and downs of the stock market. What did he learn? We'll share. Plus, we're finishing up round one of our Stacker Joke-Off...and we'll share four new math jokes AND unveil the winners of last week's matchup. All of that, Doug's trivia AND more on today's episode! FULL SHOW NOTES: https://www.stackingbenjamins.com/best-tax-software-2024-robert-farrington-1474 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever dreamed about beating the stock market? Money in your pocket and a lifestyle beyond compare? Sure you have! Here's a surprise...there are people out there who HAVE beaten the stock market, and the man who's written a series of books detailing HOW they did it joins us today! Jack Schwager is the mind behind the Stock Market Wizards series, and today he joins us again to detail a couple more wizards. We walk through lessons we can glean from them about how to invest our own portfolios, using case studies from the best and the brightest traders as a guide. Jack's last appearance was a huge it for us, so if you missed that one, you definitely do NOT want to miss today's show. In our headline segment, we dive into the new "hot" budgeting trend: LOUD budgeting. Surprisingly, loud budgeting has nothing to do with screaming while using your budget app...it's a trend around financial wellness. We talk about loud budgeting, how to join the trend, and maybe help you feel less alone if you're actually hoping to be more responsible with your cash. Of course, we also have a TikTok minute that's inspirational (you're closer to Elon Musk's net worth than you may think!). Doug also shares his wizardly trivia, and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/lessons-from-stock-market-wizards-jack-schwager-1473 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do the happiest retirees share in common? What are some of the steps you can take to get ready for retirement before you actually reach your number? On today's special roundtable discussion, we welcome Wes Moss from the Retire Sooner podcast. He joins Crystal Hammond from our sister real estate investing show, Stacking Deeds, and Len Penzo from the award-winning blog LenPenzo.com. Stick around for Doug's DIY-themed trivia! Don't worry, no effort is required on your part. FULL SHOW NOTES: https://www.stackingbenjamins.com/friday-roundtable-countdown-to-retirement-1472 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder HOW to afford a house? Already own a home but hoping to save money through better financial habits and hacks? Today we delve into the intricacies of buying a house while maintaining financial stability and building wealth. Joining us is Kimberly Hamilton, a financial educator and FinTech pro, who not only bought one house, but who also now has turned that house into a rental home and is buying a second home now for her family to enjoy. She'll not only help you develop better money skills, but also share tips on what NOT to do. ON today's Better Call Saul....Sehy & OG, we take a question from Stacker Chris who wants to continue making contributions to a Roth Individual Retirement Account (IRA) but is uncertain if he can. How does he make a Roth IRA work? OG answers Chris' question in what we all admit is the worst way possible, while still accurately helping Chris and our Stacker community know how to use a Roth IRA better. But before all of that we cover a headline from the Wall Street Journal about the state of the economy. It seems that defaults on loans are going up, yet Wall Street believes there's more room for Americans to borrow cash. But does this mean we should worry about the market? Worry about our own financial stability? Or should we worry at all? FULL SHOW NOTES: https://www.stackingbenjamins.com/stack-benjamins-on-a-dime-1471 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Shannon McLay is on a mission to clean up the dirty end of the financial planning pool. The Financial Gym founder has seen it all - advisors offering whole life policies to young savers with no children, and people just beginning saving thrown into annuities over a 401k at work. Today we talk about what to look out for in the financial world, how some of the popular buzzwords like "fiduciary" won't help you much anymore, and what to ask a potential advisor so that you know you're headed in the right direction. Before that we share a big headline about the Chinese stock market. Things haven't been going well in China, while the US market is roaring. Is it time to maybe look overseas with some of your money? How do you think holistically about buying low? We also share a TikTok minute sharing a new way to look at student loans. But of course, that's not all. Doug throws out a great trivia question and we take an interesting call from a Stacker in need. FIVE great topics on today's episode! FULL SHOW NOTES: https://www.stackingbenjamins.com/financial-fitness-with-shannon-mclay-1470 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We've all heard that you have to take on risk in order to reap the rewards of investing. Are there any ways you can achieve the rewards without taking on additional risk (in life as well as investing)? We tackle this conundrum on today's roundtable episode with Paula Pant of the Afford Anything podcast, Doc G of the Earn & Invest podcast, and our very own OG. In the second half of the show, sponsored by DepositAccounts.com, we talk to Angelo Poli, founder and CEO of MetPro, who comes back to talk about health and wellness as we enter 2024. How do you stick to your New Year's resolution throughout the year and stick to your health and wellness goals year-round? From exercise and strength training to caloric intake and protein needs to the efficiency of vitamin supplements to the effectiveness of HIIT workouts to extreme dieting and fasting, Angelo answers our Stackers questions. FULL SHOW NOTES: https://www.stackingbenjamins.com/finding-your-optimal-risk-reward-in-life-1469 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Brian Klaas has an interesting backstory...to say the least. He owes his existence to a woman who murdered her family. Because she did it--and took her own life, he was born. This complete fluke is the catalyst behind Brian asserting that your decisions matter more than you could possibly think. While planning is important, Brian emphasizes that it's even more important how you respond to all of the flukes in your life. We'll talk about the weird falling of dominos and how we're all more interconnected than we'd like to believe (and more) with Brian. Before that we take on a difficult headline; a HUGE number of advisors say they're going to retire in the next ten years. What do you do if your advisor says they're going to retire before you do? How do you change advisors...and how do you even broach the topic of retirement with your advisor? We talk all things retirement and THEIR retirement on today's show. Plus, we're continuing the first round of our Great Math Joke Off. Four more Stackers see their jokes go head-to-head for a chance to win a couple of books AND possibly more if they continue winning. We also share trivia from Doug and take a call from a Stacker who'd Better Call Saul....Sehy and OG. FULL SHOW NOTES: https://www.stackingbenjamins.com/everything-you-do-matters-brian-klaas-1468 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What’s important to you? Owning a car? Family time? Retirement? No matter what your goals are, they’re always intertwined more with the goals of those around us than we may think. For Gigi Gonzalez, culture was everything when it came to working toward her goals. When she began shoveling money toward her own non-family goals, it created rifts in her family. Did she think she was too good for them? Was she losing her cultural identity? While that’s not at all true, what is true is that balancing reaching her goals and working with her family was an important middle ground that Gigi needed to find as a first generation American AND that she passes on to others. She also helps us with our budget, car buying strategy, and more. In our headline segment, check writing is in the crosshairs of one popular New York Times columnist. We’ll talk about why YOU probably want to eliminate checks once-and-for-all from your financial life. In our TikTok minute, we talk about maybe the BEST diet AND wallet saving food on the market. We also help a Stacker who had to Better Call Saul (Sehy & OG). Of course, you can wash it all down with some awesome trivia from Doug. FULL SHOW NOTES: https://www.stackingbenjamins.com/cultura-and-cash-gigi-gonzalez-1467 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder how where you live and work could affect your ability to reach your financial goals? More specifically, is living in a big city making you poor? Here to discuss this topic on today's special roundtable episode, we're happy to welcome Maggie Tucker from the Inside Out Money podcast. She joins Len Penzo and OG to tackle this important topic and extract key lessons that Stackers can apply to their own lives. In our second half of the show, sponsored by DepositAccounts.com, we dive into what are ways that Stackers can save money despite living in a big city? Be sure to listen to the show, as you won't want to miss these tips! Be sure to stick around for the continuation of our year-long trivia game. Doug has a doozy of a question with a literacy charity-related theme. FULL SHOW NOTES: https://www.stackingbenjamins.com/is-city-living-making-you-poor-maggie-tucker-1466/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Amy Minkley is a woman on a mission. Sometimes, she admits, the mission is WAY over her head. She's an overachiever by nature, coming by her work ethic out of a need for independence when her dad left the family when she was young. From that beginning (which she says she's grateful for), Amy has gone on to big things, including creating the FI Freedom Retreat in Bali. Amy joins us for a wide-ranging episode on being okay with imperfection, finding like-minded people, and on intentional living and more. If you're feeling stuck, this is the perfect episode for you. If you're an overachiever and perfectionist, this is also the episode for you. Amy isn't the only awesome guest on today's show, though! Comedian and show writer Lisa Curry joins Joe, OG and Doug to dive into the rest of the show. In our headline segment we tackle long term care (and again the need for community when it comes to caring for our elders). Lisa offers a solution we may or may not dismiss while also being slightly fearful about it. In our new Better Call Saul (Sehy) segment, we take a question from a Stacker wondering about the Coverdell ESA. We dive into how to best plan for education, which usually doesn't include using a Coverdell. In this episode we discuss: Camp FI FI Freedom Retreat Long Term Care insurance Inflation Elder care in general Coverdell ESA accounts 529 plans ...and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/building-your-fi-community-in-bali-amy-minkley-1465 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

The founder of one of the nation's most loved budgeting tools says he dislikes the term "budget." Why? Because most of us see a budget as restrictive and limiting. The good news? Jesse Mecham from budgeting program YNAB to dive into how to make your money go further and align with your goals. We'll share thoughts about giving every dollar a job before you earn it, "aging" your money like a fine wine, the struggle every app builder has with interfacing with banks, and much more. If you either have a budget, a "kinda" budget, or are looking for a budget that works, this show is for you! But before that, in our headline, long time bond manager Bill Gross says that bonds may be overheated in this current market. What does that mean? What does it mean for your long term money? We take some time to talk through the not-so-simple idea of tying your funds to the timeline you've built to spend that dollar. If you need a long term investment strategy, you'll especially want to listen in to our headline. In today's TikTok minute, consumer finance guru Clark Howard discusses pricing schemes at both Costco and Sam's Club. Is that deal your scoring really a deal? Is it as budget friendly as they make it seem? Some deals are great and others aren't, and both of these retailers hide their strategy in plain site. Think that's all? Oh, of course we have more! This week we debut a NEW call in segment for the show. No more life line...today we'll share how we are going to handle YOUR call when you need some help with your money? Have a question? Head to stackingbenjamins.com/voicemail and you may hear yourself on the show! FULL SHOW NOTES: https://www.stackingbenjamins.com/master-your-2024-budget-jesse-mecham-1464 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What are some rules to live by to make your 2024 the best year ever? Our very own OG, Paula Pant from Afford Anything, Len Penzo from LenPenzo.com, and Jonathan Clements' article served as the inspiration for today's topic. New year, new you, amirite? We dive into mantras whose adoption could benefit you for the long term, not just until you lose your New Year's resolution motivation. We touch on our top three best pieces of advice. During the second half of the show, sponsored by DepositAccounts.com, our panel runs down their next favorite picks from the list. Be sure to stick around as our year-long trivia contest kicks off! Doug has a racy trivia question that will leave your head spinning. Which one of our three regular contributors will pull out in the lead with a W? FULL SHOW NOTES: https://www.stackingbenjamins.com/24-life-tips-for-2024-1463 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Maybe the holiday season got away from you. Maybe it's been a bigger, longer issue that you've been trying to solve. Maybe you have manageable debt, but you'd love to see it gone. Even less likely, maybe you have no debt, but wonder how to counsel those around you to help them pay off their loans. No matter, today we go to the overlords--AKA the computer--to ask AI how to solve debt issues. Chat GPT sprang on the scene just over a year ago and already has a checkered relationship with the truth. Can Chat GPT answer our debt questions? We ask it LOTS of different questions and receive some great answers and others that are...suboptimal. No matter, we spend this issue diving into how WE think you should look at your debt and solve your own debt issues. In our headline segment, one popular money management firm is in the news because rumors are swirling they're for sale! What happens if YOUR money is at a firm that is sold? We ask OG for the insider look into money management and what happens if your advisor or the place your money is parked changes, even though you didn't make a move. Is your money still safe? Is there something you can do to protect it? We dive in. And of course, we also feature some empire building trivia from Doug and much, much more. FULL SHOW NOTES: https://www.stackingbenjamins.com/chatgpt-and-your-finances-1462 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Last week we were all about focus and goal setting. Today? We'll teach you how to tenaciously grip those goals when times get tough. Jenn Drummond knows what it takes to work through adversity. She was the first woman to scale each of the Seven Second Summits, the second tallest mountain on each of the seven continents. These mountains are considered more technical as a group than the Seven Summits (tallest on each continent), and also are harder because there are far fewer resources to help you scale them. We'll walk through Jenn's adventures in Antarctica, Asia, North America, and more, as she negotiates adversity around every corner. From dreaming to planning, climbing and celebrating, we cover it all. If you want big goals in 2024, Jenn will speak directly to you. In our headline segment, some disturbing news on employment: it was harder to find a job in 2023 and 2024 doesn't look like it's going to be easier. We'll help you build a to-do list of tasks to make sure aren't on the outside looking in when it comes to your next job opportunity. Our TikTok minute features MORE 2024 predictions...this time from Professor Scott Galloway and another from Dan Yang. Both are great predictions (Galloways is slightly better), and we'll talk about home ownership extensively today. Of course, Doug will still help you become king of the virtual watercooler with today's trivia challenge AND we'll answer an interesting question from Christian who calls all the way from Germany! FULL SHOW NOTES: https://www.stackingbenjamins.com/climbing-your-next-mountain-jenn-drummond-1461 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wish a cheap plastic toy from Walmart could tell you the future? We sure do! And we try every year. It’s our annual Magic 8 Ball episode today with Paula Pant, Len Penzo and OG. Each year, we ask the Magic 8 Ball (yes, really, the one you can buy at Walmart) riveting questions for the upcoming year then reflect back on those questions at the end of the year. Today, we run through the answers to our questions from last year and ask new questions for 2024. How will the Magic 8 Ball perform this year? We’ll find out! FULL SHOW NOTES: https://www.stackingbenjamins.com/yearly-8-ball-predictions-1460 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Many of us struggle with goals. Maybe it's the words we use around them, like "legacy" and "purpose" that freak us out. For whatever reason we look into the future... ...and we freeze. Jon Acuff was one of those people. After struggling through college with "purpose" and spending lots of time wondering "what am I supposed to do next?" he found a solution. The solution worked. Today he dives into how to create goals in a manner that's not only easier, but also more fun and rewarding. Yes, you read that correctly - the process itself is rewarding and fun. We'll share exactly how it works on today's episode as he mentors us toward successful Stacking. Before that we share a headline that's also instructive. A popular money manager (Jeffrey Gundlach) took out his crystal ball and look at 2024. We'll share his predictions (our own will come on Friday's episode) and then we'll of course offer you our guidance about whether you should follow them. But that's not all. Doug shares some incredible trivia AND we answer a benefits-related question from a Stacker. ...all that and more! FULL SHOW NOTES: https://www.stackingbenjamins.com/start-2024-right-with-goals-jon-acuff-1459 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

So many distractions. You can't even read this title without thinking about your social media accounts, can you? That's okay. Neither can we. So, to help ourselves AND our Stacker community, we invited Eric Qualman to join us. He embarked on the Focus Project where he just tried focusing on ONE THING for two hours a day. How'd it work out? We'll share all, including his tips on New Year resolutions and how to block time for the important things on today's show. Plus (and before we discuss focus), we'll dive even more into the topic as we talk about Klarna and Affirm, plus companies who've done the same thing over the last thirty years. Should our Stacker not go with the BNPL company? We'll discuss winning strategies. FULL SHOW NOTES: https://www.stackingbenjamins.com/increase-your-focus-in-2024-erik-qualman-1458 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We wrap up our Best of 2023 week-long extravaganza by revisiting our first roundtable episode of the year, where Len Penzo's Magic 8-ball made some bold predictions...take a listen for yourself. Every year we ask a magic 8 ball that Len Penzo purchased at Walmart to predict the future. In the early years the ball was spot-on. Lately…not so much. But we do learn a lot about not falling into “current thinking” traps and about not worrying so much about what’s top-of-mind in the moment. The truth tends to have a longer shelf life. Please disregard any mentions of current events. This episode originally aired on January 6, 2023. You can see the original show notes here. FULL SHOW NOTES: https://www.stackingbenjamins.com/best-of-2023-magic-8-ball-1457 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Join us today for a very special installment of our Best of 2023 Week!!! Crypto? Huge profits? Taking advantage of people? Has that ever happened before? It turns out that it has, in the wild, wild west, which roped in celebrities like Wild Bill Hickok and many others. Today, we’ll tell their stories and rope the lessons around to today with master storyteller and host of the Legends of the Wild West podcast, Chris Wimmer. Please disregard any mention of current events, as this episode was originally broadcast on June 12, 2023. See the original show notes here. FULL SHOW NOTES: https://www.stackingbenjamins.com/best-of-2023-chris-wimmer-1456 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's special "Best of 2023" episode, we revisit a conversation Joe had with Dr. Julia DiGangi. How much of your own emotions and energy go into your financial decisions? Dr. Julia DiGangi joins Joe to chat about how to master your emotions and maximize your energy. She teaches us how to recognize stress triggers so you can control your emotions and energy before they get out of hand. What proactive steps can we take to master our emotions? This episode was originally released on September 27, 2023, so please disregard any mention of current events. You can see the original show notes here. FULL SHOW NOTES: https://www.stackingbenjamins.com/best-of-2023-dr-julia-digangi-1455 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's best of 2023 episode, we revisit an exclusive interview that Joe had with superstar runner Kara Goucher who shared her experience of abuse while on the elite Nike running team. This episode originally aired on March 15, 2023, so please ignore any mention of current events. For the original show notes, visit Kara Goucher on Abuse, Money, and the Elite Nike Running Team FULL SHOW NOTES: https://stackingbenjamins.com/best-of-2023-kara-goucher-1454 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

In our inaugural Best of 2023 episode, we revisit a Top 5 episode all about moves to make to win at the money game. Joe and OG dive into their top five moves to become a champion at all things money. We’ll talk about everything from motivation to tactics during our feature segment. This episode originally aired on February 8, 2023. Disregard any mention of current events. The original show notes can be found at Top 5 Plays To Win The Money Championship Game FULL SHOW NOTES: https://stackingbenjamins.com/best-of-2023-top-5-1453 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's special roundtable episode, our panel members share what money lessons we should have learned in 2023. Joining us on the year-ending roundtable are Paula Pant from Afford Anything, OG, and .....NEIGHBOR DOUG. What are some of the most important things that happened in 2023? From Taylor Swift to Charlie Munger to inflation and rising interest rates, we cover the year's hottest topics in today's episode and dissect them into lessons you can apply to your life in the coming year(s). We'll touch on lessons in appreciation and gratitude, lessons in building systems, lessons in the importance of team building, lessons about the convergence of career and financial success, the life and lessons of Charlie Munger, the concept of "enough," how retirement (or FIRE) isn't just about accumulating a huge stack of Benjamins and then stopping work altogether, how recent inflation has impacted how we handle our money and where we go from here, the wisdom of waiting to buy a new home, AI, the fallacy of short-term thinking, and more. Since our year-long trivia competition's winner was locked in by Len Penzo last week, Joe unveils a new twist on the trivia game: deciding who goes last in our first trivia episode next year by playing a little game called "Benjamin in Your Box" (insert 12-year-old snicker here). Will Paula or OG win the advantage of going last? FULL SHOW NOTES: https://www.stackingbenjamins.com/year-end-recap-roundtable-1452 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

LOTS of incredible events happened this year. What should we have learned from a big bank collapse? From Bitcoin resurging? From the stock market moving up (along with interest rates)? We asked about all of these and more to Today Show Money Editor and host of the Her Money podcast, Jean Chatzky. Jean shares great tips on your budget, investments, money in bank accounts, and more. But that's not all. In our headline segment we share some of the recent moves in interest rates. Now with rates beginning to fall again, are there moves we should have made? We also throw out the lifeline to a Stacker who needs help AND Doug shares his best trivia ever. FULL SHOW NOTES: https://www.stackingbenjamins.com/year-end-recap-with-jean-chatzky-1451 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

One snowy Christmas Eve in Texarkana, Neighbor Doug settled into bed in his snazzy Superman Footie PJs (Amazon affiliate link), still buzzing on Joe's Mom's eggnog... Today's special holiday episode recounts a completely original tale of Doug and the money lessons learned when he's visited by three ghosts—past, present, and future. Make peace with your past, clean up your past mistakes, and learn from them Especially when it comes to past credit mistakes, what's done is done. Whatever method works best for you (debt snowball or debt avalanche), do that one. Come to terms with your bad money habits and realize that you can't outearn them. It's on you to fix the bad money habits of your past. Focus on what's current and fix what needs fixing today. Live in the present Don't get caught in the trap of lamenting your past nor only planning for the future. Our only truly limited resource is time. Balance living for today with planning for the future. Remain in the present - especially when spending time with your loved ones - while keeping a vision in mind for your longer-term future plans. Be intentional about your plans and actions today and timeline what you want to achieve in what time you have remaining. Plan for the future Communicate on a regular basis with your "team" (loved ones) about your financial goals, progress, and situation. We recommend scheduling a weekly Family Budget Meeting. Automate as many of your financial decisions as possible today so you never have to think about them again in the future. Commit to paying off that mortgage early, ramp up those retirement savings contributions, stack those Benjamins for your kids' college savings. Decide where you want to be financially in the future; face reality of where you are currently (we like our sponsor, Monarch Money, to track where you are); and take the necessary step to make that future a near certainty. Takeaways Remember that time is the one commodity that's finite for all of us. Value your time and experiences while staying responsible to your present and future self. Remember and learn from the sins of your past to build on your strengths; focus on living in the present and building your financial foundation; and head into the future with more confidence that Joe's Mom's Neighbor Doug during the annual Sun's Out; Guns Out El Camino Competition at the Sizzler. FULL SHOW NOTES: https://www.stackingbenjamins.com/doug-and-the-three-ghosts-1450 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is retirement, as we know it, dead? Should the idea of retirement itself be retired, and should we all aspire to be like Betty White? Will all those decades of toiling away for The Man (and dutifully contributing to your personal retirement savings accounts, as well as you and your employer throwing in 6.2% each of your salary to the payroll tax, a.k.a. Social Security) pay off in the end when you reach the end of your working career? Is it worth postponing "happiness" during your working years in the hopes of living a life of leisure when you're older? Joining us for this special conversation, from The Personal Finance Podcast, we welcome Andrew Giancarlo; Betty White wannabe, Afford Anything's Paula Pant; and our resident Betty White fanboy, OG. The concept of reaching an arbitrary age and stopping work cold turkey may be an illusion for many aspiring retirees, as many recent retirees find their lives lacking purpose, meaning, and (in some cases) sufficient Benjamins. The FIRE movement isn't necessarily about ceasing all productive activities, but rather achieving financial independence so that you are in control of how, where, and with whom you spend your time. We also dive deeper into how you can make up for any potential retirement savings shortfall and examine the pros and cons of Barista FIRE that can be used to supplement income needs after retiring. We'll also discuss how altering your lifestyle can affect the amount you'll need to save for retirement. In the second half of our discussion, sponsored by DepositAccounts.com, we jump into the solutions to solve the big retirement savings gap problem. What actions can you take to improve your retirement savings and quality of life, even if you're approaching retirement age? What actions can you take today that your future retired self will thank you? Finally, be sure to stick around for the next thrilling installment of our year-long trivia competition. Will Andrew help Len seal the deal for this year's W, will OG stay alive, or will Paula throw a monkey wrench in the plans? FULL SHOW NOTES: https://www.stackingbenjamins.com/retirement-planning-mistakes-and-solutions-andrew-giancola-1449 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Do you want to be a great investor? We're going to dive into a few ways...including how rich people view investing and money in a much different light than non-wealthy people. To kick things off, during today's headline we'll share a list of mistakes that new investors make all of the time. We've made these mistakes ourselves and lived to tell about them. Now we're going to help YOU avoid those mistakes as well, so you can build wealth more quickly. We'll discuss overtrading your positions, gambling like the stock market is a casino and more. That's all a big lead-in to a woman who's helped MILLIONS of people on TikTok become better investors and think much more like a wealthy person. Your Rich BFF Vivian Tu joins us for a great discussion on the importance of mentors, focusing on the fundamentals, and more, if you're hoping to join the wealthy class. Vivian has been both poor and wealthy and is going to help us mentor you to invest better as well. More than anything, she's going to help you focus on your mindset to not just invest better but to make better money decisions across the board. Of course, we'll also take a call from a Stacker who wants to be a better investor, AND we'll even help you hone your trivia-solving skills with Doug's trivia question. ...and to top it all off, we JUST might share a holiday special TikTok minute. FULL SHOW NOTES: https://www.stackingbenjamins.com/rich-af-bff-vivian-tu-1448 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How many times have you seen someone try to make their big money move and it fizzles out? Often it's because they started at the wrong place or didn't pay attention to the fundamentals. We're going to help you build your BEST launching pad today with financial whiz and host of the Journey to Launch podcast, Jamila Souffrant. Before Jamila though, our headline from CBS News warns about new and even more intricate scams this holiday season. We chat with AARP's Kathy Stokes about the warning signs something might be a scam AND the fact that LOTS of these con artists aren't targeting our older generation...but instead going after young people online. We'll share details on today's show. Of course, we'll throw out the life line to a lucky caller AND we'll shine a light on the most adorable TikTok minute we've ever had on this podcast. Of course, you can't say "adorable" without thinking of Doug's trivia, which we'll also have on today's show. FULL SHOW NOTES: https://www.stackingbenjamins.com/your-journey-to-financial-freedom-jamila-souffrant-1447 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's the best safe withdrawal rate for your retirement plan? What the heck is a safe withdrawal rate? On today's special roundtable discussion, we dive into the deep end of this important topic: understanding what you're investing in, what different financial terms mean, and if they're important for you. We're thrilled to welcome our special guest, Bernadette Joy, to our roundtable panel. She's the force behind Crush Your Money Goals, a money media company to serve up fun and practical educational content. Our own OG joins her at the card table, along with Len Penzo, creator of the award-winning blog LenPenzo.com. In our second part of our discussion, sponsored by DepositAccounts.com, we dive into each of our roundtable contributor's favorite pieces of basic and advanced get-out-of-debt advice. Stay tuned for the next chapter in our year-long trivia contest. Doug brings the trivia suspense with an 'Ol Blue Eyes-infused trivia question. Will Bernadette keep Paula in the running for the year-end trophy, or will OG or Len put it out of reach? Listen and find out! FULL SHOW NOTES: https://www.stackingbenjamins.com/fri-roundtable-basic-vs-advanced-advice-1446 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What is the best "next move" for your career or your passion? Keep moving. Dr. Mike Massimino knows how to achieve unlikely goals. He not only applied to be an astronaut three times before being accepted as a candidate, the third time he applied he was medically disqualified. Yet, he still found a way to work about two different space missions, was the first person to tweet from space, and act on several episodes of the Big Bang Theory. We ask him about all of this and more, and he drops some terrific leadership advice. No matter who you are, this interview can help you achieve more. Before that, in our headline segment, a player has been dismissed from a professional sports team. What does that have to do with you? We dive into the actions of the Chicago Blackhawks against player Corey Perry, and how that just might change your outlook as you make your way through December. Of course, we still share Doug's trivia and OG answers a question about employee stock ownership plans. All that and more on today's show! FULL SHOW NOTES: https://www.stackingbenjamins.com/valuing-fresh-perspectives-mike-massimino-1445 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Whether you're leading your family, a department or work, or heck, "managing from the middle," every one of us has leadership potential inside of us that's untapped. And it's this time of year, when we're thinking so much about what we value and need in our lives that the topic of leadership is so important. That's why we asked Chuck Wachendorfer to be our Stacker mentor today. He met Joe and OG while leading a team at American Express and now helps major organizations, small business owners, and government entities develop better leaders. We talk to him today about the biggest issue in leadership: what do you do first when trying to lead? You may be surprised by his answer. In our headline segment we mark the passing of one of the greatest investors of our time. Charlie Munger passed away last week and we pause for a moment to talk about many of the common sense ideas Munger advocated and share some of his (maybe surprisingly) very funny takes on things like crypto currency. Of course, we'll delight you with the TikTok minute, shining a light on a creator who may or may not be sharing some brilliant insight about money management. We'll also throw out the lifeline to a lucky Stacker who needs our help. This time we help Allie determine annuity options for her work. When you retire, how should you think about your income stream? You'll want to listen to OG's answer. Of course we also feature Doug's trivia, the back porch, and more! Enjoy! FULL SHOW NOTES: https://www.stackingbenjamins.com/leadership-masterclass-chuck-wachendorfer-1444 Learn more about your ad choices. Visit podcastchoices.com/adchoices

What are the most common ways people shoot themselves in the foot (financially-speaking)? Here to tackle that very question is our expert panel of contributors: from Afford Anything, we're joined by Paula Pant; from the aptly named award-winning blog LenPenzo.com, Len Penzo joins us; and from across Joe's card table, the man, the myth, the legend OG makes an appearance. Will Len lock secure victory for the year-long trivia game, or will Paula or OG stay in the game? In the second part of the show, sponsored by DepositAccounts.com, our panel rounds out their top 10 financial mistakes. As we enter the last month of the year, Doug brings some Christmas tree-themed trivia. Can Len score an extra point, bringing him one step closer to victory? Will OG defend his title and take the W? Will Paula continue her unlikely come-back rally? Tune in to find out! FULL SHOW NOTES: https://www.stackingbenjamins.com/top-10-financial-mistakes-1443 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How many times have you found yourself headed into the company holiday party thinking, "I hope I don't end up stuck in a conversation in the corner with someone"? Then, five minutes later, you're stuck in a boring conversation in the corner with someone? Or, you're trying to make a statement around the boss during a group conversation and you just can't figure out what to say? Or (and maybe worst of all), you're in a meeting and in front of all of the influential people someone asks, "So what do you think?" Impromptu speaking isn't just important around the holidays, but this time of year we're all more likely to be in a conversation with people who challenge our ability to communicate effectively. Today we bring you a great mentor on the topic, Matt Abrahams, who's not only an expert communicator, but he's so good that he teaches the topic at Stanford University and hosts a podcast on the topic. That's not all the communicating we'll do, though. We'll also discuss a recent Wall Street Journal piece which shares how much money people think they need to make before they'll finally be happy. That will lead us into a deeper conversation about what it really takes to be happy...and it turns out the answer might not be what you expect. That's not all! Of course, we'll also have some trivia from Doug, share the life line question, and more. FULL SHOW NOTES: https://www.stackingbenjamins.com/think-and-talk-fast-with-matt-abrahams-1442 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Everyone says they know a great "money hack" but Tiffany Aliche (The Budgetnista, Brown Ambition podcast), knows LOTS of them and shares one that Joe calls "his favorite" core idea. While we aren't really fans of the term "money hack," in this case it most certainly applies. She also talks about accountability (probably also a money hack), her favorite insurance strategy, and then we take a LONG walk down a tangent that begins with estate planning. You'll hear about love, pain, the true role of money, what to do when you lose a loved one, and more. Before that, OG and Joe share a TikTok minute featuring a guy who's implemented his share of money hacks: Gordon Ramsay. We also throw out the Life Line to a lucky listener, and much, much more. FULL SHOW NOTES: https://www.stackingbenjamins.com/get-your-budget-right-tiffany-aliche-1441 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome to Joe's favorite episode of the year—our annual Black Friday board game episode! Joining us on this Black Friday, we are thrilled to welcome the BoardGameGeek herself, Candace Harris! She'll give us the lowdown on what's hot when it comes to finance and business-related board games! Plus, Neighbor Doug has a classic board game trivia question that's sure to Boggle your mind! FULL SHOW NOTES: https://www.stackingbenjamins.com/black-friday-board-games-candace-harris-1440 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Some of the most expensive items in your life after your home and transportation are technology related. That's why each year, before Black Friday, we dive into our favorite technology items with CNET's expert Bridget Carey. This year Bridget shares what to watch out for in tech (there's always some sneaky "gotcha" waiting around many "great deals." We talk about household items, security, dive DEEP this year into the world of televisions, dip into the toy department, and more. But that's not all. Before that we get you up to speed on headlines about Dave Ramsey's eight percent solution to taking money from your retirement portfolio AND a headline about obscure investments. What could happen if you find a quirky but great-sounding investment opportunity? While we share a horror story, we also offer solutions and strategies to help you not get burned if you do decide to take the plunge. Of course, we'll also answer a question from a lucky Stacker AND we'll share Doug's incredible trivia question. FULL SHOW NOTES: https://www.stackingbenjamins.com/black-friday-tech-report-bridget-carey/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

With prices up (inflation) and wages stagnant, this is a GREAT year to look to save big on holiday gifts (and also to save big on those things you needed to buy anyway for around the house!). Regina Conway from Slickdeals makes her annual stop in Joe's mom's basement to dive into ALL of the top deals the fans at Slickdeals have found. We cover clothing, toys, kitchen gadgets, housewares, garage items, personal care, and more! With tons of great deals (and some quirky ones, too), you're sure to save big on your holiday season with Regina's help. And that's not all. In our headline segment we share the recent news that Mint, the popular money tracking app is shutting down. If you're trying to save big money into savings AND want to find the best app to track your cash, which way should you turn for support? We share MANY of our favorite solutions and why we like them so you can focus on the options that fit you best. Of course, that's not all. We share a TikTok minute, throw out the lifeline to a lucky Stacker, and of course share some of Doug's amazing trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/black-friday-save-big-with-regina-conway-1438 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you looking to become rich? How do you define rich? What are your preconceived ideas about how to best get there? On today's special roundtable discussion, we're tackling that question and debating what the "best" ways are to hit that rich goal. On today's show, we're thrilled to have Crystal Hammond from our sister show that's all about real estate investing, Stacking Deeds. Crystal joins Len Penzo from Len Penzo dot Com and OG, CFP and co-host extraordinaire of this here Stacking Benjamins podcast. In the second half of our show, sponsored by DepositsAccounts.com, we round out the remainder of the top five ways to get rich. Stay tuned for Doug's Benjamin-laden trivia question. Will Crystal keep Paula in the game as we head down the stretch into the end of the year? Can OG orchestrate a comeback? Will Len extend his lead? Stay tuned to find out! FULL SHOW NOTES: https://www.stackingbenjamins.com/fri-roundtable-top-5-ways-to-get-rich-1437 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Everyone wants something for nothing. Today's guest says the term "passive income" is a lie, and he's the guy hosting the biggest podcast in the "passive" income space...BiggerPockets! David Greene joins us again, this time to share his journey from being a guy with ZERO contacts and ZERO money to a guy wealthy beyond belief, with a giant team, and a career that most would love to have. We share his incredible journey that began working part time at a (of all places) Baskin Robbins ice cream shop. You'll learn what to focus on if you want wealth, how to build skills, and what NOT to do if you hope to advance up the career ladder. Plus, it's fire safety month! We're joined by Adam Barowy from UL's Fire Safety Research Institute. This year we're highlighting the dangers of lithium batteries, especially some of the big ones found in e-bikes and large powered toys. He'll dive into how to tell when there's the potential for a fire, how to identify potentially unsafe batteries, and how to practice good fire safety. Of course, we still leave time to throw out the life line to a lucky Stacker (even one from Ohio!), and dive into some of Doug's incredible trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/the-truth-about-passive-income-david-greene-1436/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

It seems like an uncertain time, doesn't it? High inflation, high interest rates, job uncertainty for some...and just under one year from now, a huge presidential election. These are the types of years when people sit out of the financial markets. They wait for "calmer waters" and "better times" to invest, moving their money to cash. But is that the right move? What should you do with your money as we ramp up toward another presidential election cycle? Today we've assembled an All-Star panel to address that very question. From T. Rowe Price, CFA and Capital Markets Strategist in the Multi-Asset Division, Tim Murray joins us. And from Fidelity Investments, Certified Financial Planner and Vice President, Financial Consultant Ryan Viktorin also chimes in, as does our behavioral expert, Certified Financial Planner and Co-Founder of the Financial Psychology Institute, as well as Associate Professor of Practice at Creighton University, Dr. Brad Klontz. We're excited they're all here and ready to help you guide your financial boat into safe waters. Do you know someone who's really worried about this election? This is definitely the episode for them! Share this with them so that you can help them stay calm and avoid potentially horrible moves with their money. FULL SHOW NOTES are at StackingBenjamins.com/investing-in-an-election-year-special-1435. Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here's a question: who walked into work recently and said, "I hope I suck at my job today?" I'm hoping the answer is NONE of our Stacker community. And yet, many of us underperform every day. Why? There are so many ways that we can make ourselves smarter, faster, better at our jobs. We shouldn't leave whether we're excellent at our jobs to our boss, and yet, there ARE some things that we and our boss can both do to transform our workplace and make our company better. Today we're joined by the guy who the world's wisest bosses turn to when they're wondering how to get their workforce to work better -- Andrew McAfee. Andrew has picked the lock on why some companies stink when it comes to empowering their team to rock at their goals and others wallow in mediocrity. He tells us the meaningful stories of how some leaders have transformed their workplace on today's show. But of course, that's not all. In our headline segment, there's good news for people saving for college. The rules have gotten easier? Unfortunately, we don't mean "easier to understand," but just "you can now save more money that helps you also not screw yourself over for financial aid." We'll discuss the secrets you need to know on today's show. You think transforming the workplace is all you need? Now you can also save money on your college costs? Double-whammy! And yet, we still bring you more. We also throw out the Haven Life Line to a guy wanting to "learn something" from the show (he must not know that Andrew McAfee is bringing it this episode!)...and asks us about putting money into a "donor advised fund." What is that exactly, how does it work, and will it transform your workplace? The answers are: "It's complicated, so you should listen," "It helps you avoid LOTS of taxes," and "No." There's still SO MUCH MORE! Come join the fun. FULL SHOW NOTES: https://www.stackingbenjamins.com/find-bigger-opportunities-andrew-mcafee-1431 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Our top article today discusses the current financial markets. If you thought stocks were going to move south, why wouldn’t you do anything about it? We ask our panel today that question and two more. Today’s show features an all-star guest roundtable line up. PT from the new Masters of Money podcast, Len Penzo from LenPenzo.com, and Paula Pant from the Afford Anything podcast debate and discuss our three topics ripped from the popular press on today’s show! This show originally aired in 2016, so please ignore any mention of current events. FULL SHOW NOTES: https://www.stackingbenjamins.com/timing-the-market-rewind-1433 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's special Stacking Benjamins Rewind episode, we jump into the way back machine to listen to an episode from our friend Doc G's Earn & Invest Podcast. If you think personal finance is personal, you're mistaken! We hear it all the time: "personal finance is personal". In today's episode, JL Collins and Scott Trench join Doc G and they question this popular saying. While tactics and personal needs may vary, there are better and worse ways to invest and build wealth. Join us as we dive into the weeds. This episode of Earn & Invest Podcast originally aired on June 19, 2023, so please ignore any mention of current events. For the original episode's show notes, you can see them at If You Think Personal Finance is Personal-You're Mistaken! — Earn & Invest (earnandinvest.com). FULL SHOW NOTES: https://www.stackingbenjamins.com/is-personal-finance-personal-earn-invest-rewind-1432 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

In today's special rewind episode, we feature an episode from our sister show, The Stacking Deeds Show. Are you a novice investor interested in real estate? Do you want to learn how to navigate the world of real estate investing and make a positive impact in your neighborhood? In this episode of The Stacking Deeds Show, we dive into the importance of neighborhoods and how investing in real estate can help improve and strengthen communities. Join us as we discuss the challenges and opportunities of investing in fragile states, the power of building relationships in neighborhoods, and the importance of taking a horizontal approach to real estate investing. Whether you're a seasoned investor or just starting out, this episode will provide valuable insights and strategies for making a difference in your community through real estate. This show originally aired on October 17, 2023, so ignore any mention of current events. To see the original show notes, visit Saving Distressed Neighborhoods Through Responsible Real Estate Investing: with Dr. Seth Kaplan (stackingdeeds.net). FULL SHOW NOTES: https://www.stackingbenjamins.com/rewind-stacking-deeds-distressed-neighborhoods-1431 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

At what age do you think will be the best days of your life? How do changing priorities impact how you view happiness? What role does stress play in detracting from the best days? What role do finances and financial independence play in happiness? Today's special roundtable discussion is all about the evolution of life satisfaction and the best days of your life — and how your happiness changes as your age progresses. What about the impact that having children has on your happiness? Joining us for this important roundtable discussion, we're proud to welcome the co-host of the How to Money podcast, Joel Larsgaard. He joins Afford Anything's Paula Pant and our very own OG as they offer their opinions and experiences on how the best days of our life and satisfaction change as we age. In the second half of the discussion, sponsored by DepositAccounts.com, our panelists share their thoughts on whether we should focus on achieving financial independence faster in order to the best days of our life quicker? We also discuss how taking an optimistic outlook may benefit you in the long run. Be sure to stay for this week's edition of our year-long trivia contest. Doug breaks out the way back machine and has some 90s pop music-themed trivia. Does that spell certain doom for Paula? Will she or OG break their current tie and join Len in first place? Or will Joel make Len proud and increase his lead? FULL SHOW NOTES: https://www.stackingbenjamins.com/friday-roundtable-best-days-of-your-life-1430 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

What keeps YOU up at night? We asked an All-Star panel that you can only put together at a big conference like FinCon...and today we do just that. We're recording LIVE from the moomoo podcast booth at FinCon 2023 with Rob Berger (Rob Berger YouTube channel), Nick Loper (Side Hustle Nation), and Paula Pant (Afford Anything), to ask them what THEIR audiences are worried about right now. Man, did we get an earful. From rising interest rates to uncertain retirement conditions, to the world of work changing around us because of AI and more, we work through MANY of the big issues people are facing in 2023 and often come up with solutions to help relieve those fears. It's a special episode of Stacking Benjamins, without our usual segments (only the trivia remains...and Doug brings us a GREAT one today). Enjoy! FULL SHOW NOTES: https://www.stackingbenjamins.com/live-from-fincon-new-orleans-1429 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Financial independence. It's often presented by writers as the place dreams are made of. You've reached this magical place called "enough" and now life is all unicorns and rainbows. But what happens when you realize that the march toward shoveling everything toward an uncertain future is creating a horrible existence TODAY? That's what happened to Jess, one half of the Plutus Award winning coaching team The FIoneers. Jess and Corey came by Joe's mom's basement to tell the tale of their "a-ha" moment that led them to reject shoveling tons of cash from a hated job toward an early retirement...and maybe an early grave. Before that we celebrate our Halloween-kickoff episode with a visit from financial columnist and the host of the Money Life podcast, Chuck Jaffe. Chuck orchestrates an awesome, interesting, and always-changing economics game every Halloween with the trick-or-treat'ers who come by his home. What's the game this year? He'll share what he's planning, and hopefully inspire you to find clever ways to teach kids some money or economic lessons. Of course we also throw out the Haven Life line (this time all the way to India!), and Doug regales us with his mind-bending trivia. It's a Halloween party in the basement! Hope you can join us. FULL SHOW NOTES: https://www.stackingbenjamins.com/FIRE-horror-story-1428 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Les Brown, no stranger to hard work and the resulting success it brings, famously said, “Do what is easy, and your life will be hard. Do what is hard, and your life will become easy.” Does the secret to creating an easy life lie in doing hard work first? How much of what seems easy from the outside looking in is actually the result of hours of hard work that was put in beforehand? Joining Joe for a special roundtable discussion that centers around how to do the hard things in order to create an easier life going forward are three people who are no strangers to doing the hard work: Roger Whitney, the Retirement Answer Man; Carl Jensen, creator of the 1500 Days to Freedom blog; and Paula Pant, host and creator of the award-winning Afford Anything podcast and blog. They dive into the complex relationship between hard work and an easy life and offer some gems for Stackers to take away. In the second half of our show, sponsored by DepositAccounts.com, we discuss some hard work life skills and money skills that you can tackle today that will help you out financially in the future. Be sure to stick around for our resident hard work expert Doug's astrological-themed trivia! Will either of our two guest contributors pull out the W and Len or OG benefit from their hard work, or will our regular contributor Paula continue her late season charge for our spectacular dollar store trophy? FULL SHOW NOTES: https://www.stackingbenjamins.com/friday-roundtable-hard-work-easy-life-1427 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Want to know how to stack AND enjoy more Benjamins? Us too! That's why we like taking life advice from the right people. In our minds, Ron Shaich, founder and former CEO of Panera Bread joins us to talk about living a life of service. Ron's had a full life, making money quickly but still working. How come? It turns out, Ron's best life advice revolves around how to live with meaning, rather than chasing money. We talk about his early days with the company, reinventing Panera before it was broken, and coming back out of "retirement" four times to pursue the next phase of running the business he loves. Speaking of life advice...one crypto trader could use some. Mom always said "measure twice and cut once" when doing anything. This trader lost OVER one hundred thousand dollars on a trade recently. We'll share how and what life advice this may mean for you! (There's plenty). Of course, we still throw out the Haven Life Line to a lucky listener and also dive into some of Doug's juicy trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/know-what-matters-with-ron-shaich-1426 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Has the cost of...everything...got you down? Us, too. That's why today we bring you our Top 5 Ways to Cut Expenses Fast! If you're looking for some easy wins, we're bringin' them, along with a couple ways that may not be the fastest ways to cut expenses, but are completely worth the time and effort it'll take. Has the return to the office had a bigger impact on your Benjamins stack than you remember? In our headlines segment, we see how many American workers are coping with the surprising cost of returning to the office. Check out our TikTok Minute that may have you questioning the wisdom of having kids. And stick around for Doug's crime boss-related trivia that will have you double-checking your tax returns to make sure the IRS stays off your back. FULL SHOW NOTES: https://www.stackingbenjamins.com/top-5-expense-cuts-1425 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you letting your dreams of financial freedom slip through your fingers, always putting them off until tomorrow? Join us for today's special roundtable discussion, where we explore the art of not postponing gratification while still pursuing your financial freedom. Our featured guest is none other than the "Ordinary Sherpa" herself, Heidi Dusek, who joins Doc G and Len Penzo in this insightful conversation. Discover the delicate balance between securing your future financial freedom and living in the present. Learn how to achieve financial independence without sacrificing the joys of today. Plus we delve into the potential impact of achieving financial freedom at a young age, including the challenges of leaving your old community and forming a new financial freedom community. In the second half of our episode, DepositAccounts.com, we examine the unforeseen changes that early retirement can bring into your life. And last but not least, our year-long trivia competition is reaching its climax! Who will come closer to being crowned the ultimate champion? Stay tuned for Doug's opera-themed trivia challenge! For comprehensive show notes, including additional resources and references, please visit: https://www.stackingbenjamins.com/accelerate-financial-freedom-roundtable-heidi-dusek-1424. For even deeper insights, curated links, and in-depth discussions on the topics covered, be sure to explore our newsletter, "The 201," available at StackingBenjamins.com/201. Sit back, relax, and enjoy the episode! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Where have you seen inflation the most? Maybe in travel. Between flights, the rental car, lodging, and admission fees, it feels like it takes FIVE bags of Benjamins to leave your back door for a long weekend! On today's show, we're thrilled to welcome travel savings expert Lee Huffman. He shares tips, tricks, and best practices to get the most out of your travel savings, wherever you may go. Be sure to tune in and get the most travel savings on any upcoming travel plans you have. In today's conversation, Joe and Lee dive into travel savings when traveling domestically vs. travel savings for international travel. They chat about the travel savings to be had through rewards programs, how to accumulate the most points for your travel savings, and which programs offer the best value. They also touch on how Airbnb and VRBO stack up against the big hotel chains. They also dig into the best flight rewards programs for your travel savings. And they discuss the value of TSA Precheck and Global Entry. In today's headline, we see how the recent Social Security cost of living adjustment (COLA) may fall short of its stated intention—to keep up with rising inflation. We throw out the Haven Lifeline to Patrick who has a question about 529 plans for his future children. Plus, Doug dazzles us with his 90s fashionista awareness trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/travel-savings-and-tips-with-lee-huffman-1423 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever think that you aren't sure where you're headed with your money? Today we talk to TWO guests who began experimenting and found themselves much more prepared for the future than they'd thought. First, Annie decided it was time to experiment with "van life" during the pandemic. Her goal? To see if living and working from anywhere was actually viable. She'll share her stories, including what worked, what didn't and what she thinks about trying again long term. Plus, Tonia shares her story of how she realized she could actually quit her job! That was a welcome shock and now she shares what it's going to take for her to jump off the employment treadmill and into a new life. Think that's awesome? We're also joined by special guest co-host Becky Heptig, who along with her husband Stephen retired at 60 after only beginning the journey toward financial independence ten years earlier! She's the co-host of the hot new podcast "Catching Up To Fi," and she helps steer this ship today! Welcome to a very special edition of Stacking Benjamins! On today's show, LIVE from Bali, Indonesia, Joe shares interviews and stories with a live audience at Amy Minkley's FI Freedom Retreat, where he was a keynote speaker. Not only does Becky Heptig from the Catching up to FI Podcast co-host, but she also shares her and her husband's success story about how they achieved financial independence in a relatively short time, starting from zero at the age of 50. Joe's interview with attendee Annie is an eye-opening look at just how different financial independence can look for different people, with Annie's path fully embracing the location independence through #VanLife. Could camping, vagabonding, and generally roughing it be right for your financial independence? Annie shares the pros and cons of adopting this lifestyle. Joe also sat down to talk with Tonia, who's story about how she unknowingly stumbled her way to financial independence hopefully will help you realize that maybe you're closer than you think to success! Learn from Tonia how to make the right moves to secure your financial independence by starting early. Stick around when Doug calls in some Bali-related trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/live-from-bali-financial-independence-retreat-1422 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Tune in on Wednesday when we're going to help you see the world for less money (and to better splurge so that you create awesome memories) with the man behind the We Travel There podcast, Lee Huffman. Written by: Kevin Bailey Miss our last show? Listen here: The Money Tipping Point: When Do Saving, Spending and Earning Habits Go Too Far? (SB 1421). Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much is too much of a good thing? How do we achieve the optimal balance between the two extremes of cheapskate and YOLO? Joining us for this extreme discussion we welcome the founder of the EconoME Conference and Doug's ex-girlfriend, Diania Merriman; Doc G from our sister show, the Earn & Invest Podcast, and writer extraordinaire, Paulette Perhach. They'll discuss what makes for extreme saving and extreme spending. In the second half of this extreme roundtable discussion, we talk about how to find the right balance between the two extremes, based on your priorities and goals in life. Finally, stick around for Doug's extreme sports-themed trivia! With all three of our regular contributors MIA, who will walk away with the W as we enter the second week of the fourth quarter? FULL SHOW NOTES: https://www.stackingbenjamins.com/friday-roundtable-extremes-diania-merriam-1421/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

With so much emphasis placed on saving and investing throughout your working career to insure a secure and wealthy retirement, sometimes enjoying your life today can take a backseat. On today's show, we're joined by author Frank Legan to talk about adding humanity and the need to live your life in the moment into your financial planning. It's all about reaching a balance between planning/saving/investing for the future with treasuring and living your life today. In short, we're talking about choosing your investment choices - not necessarily which ETFs or funds, but the investment choices of what are your priorities in life. We all know that we're responsible for our financial future, but at what point do we stop viewing "investment choices" as simply picking the right stock/ETF/fund/saving account and start placing a greater focus on choosing how much time we truly spend with those we care about and not always in the pursuit if more Benjamins? Make the right investment choices that align with your values, goals, and priorities! In our headlines segment, we look into a all-too-common recurring theme: Americans and their penchant for spending. Talk about making investment choices in the wrong way! We throw out the Haven LifeLine to Jodi in Michigan who wants our take on annuities and how they can complement Social Security later in your retirement years. Could a deferred annuity be among the right investment choices for your finances? And Doug brings it home by throwing out some investment returns-related trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/financial-planning-for-your-life-frank-legan-1420 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you ever felt overwhelmed by the sheer quantity of stuff you have accumulated? Ever looked at the mountains of stuff and wondered how many Benjamins you could flip that into? Joining us today are a husband-and-wife team, professional flippers Melissa and Rob Stephenson. We'll learn about how they started flipping, how to actually make money flipping, and how you could make flipping your side hustle. If you have ever wanted to learn how to make money on eBay, Amazon, or Facebook Marketplace, you don't want to miss today's interview all about flipping! In our headline, we see how CDs have become a respectable option for parking some of your cash for safety. Stacker Jeff calls into the Haven Lifeline with a question about how to make up for lost time investing. Plus, Doug brings some flipping-themed trivia in honor of Melissa and Rob coming on the show. FULL SHOW NOTES: https://www.stackingbenjamins.com/flea-market-flippers-melissa-and-rob-1420 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you define a wealthy life, and what how do you identify "wealthy?" On today's special roundtable, our panelists share their reactions to a piece that tackles how we define wealth—and not all wealth is tied to how many Benjamins you make. We're joined by our friends Miranda Marquit, Paula Pant, and Len Penzo. Is wealth to you taking a fancy, luxurious vacation every year? Or do you define wealth as having the freedom to step into your own backyard sanctuary and fire up the grill? Is wealth to you the peace of mind to walk away from your 9-to-5? In the second half of the show, we'll dive into the importance of having a good work-life balance. Finally, our year-long trivia competition is entering the home stretch. Stay tuned for Doug's fancy transportation-themed question and find out who pulls out the W. FULL SHOW NOTES: https://www.stackingbenjamins.com/friday-roundtable-wealthy-traits-1419 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Fear is such an innate and naturally occurring emotion that we may write off irrational fear, or even living in a constant state of fear as normal. What impact do your acquired or ingrained fears have on your life, success, and finances? How do we acknowledge, come to terms with, and ultimately overcome our fears to reach our full human potential? Joining us to tackle this important topic is our friend and host of the So Money podcast, Farnoosh Torabi. In our headline, we explore a study that shows the impact of spending "spikes" and the resulting loans/debts incurred on retirement readiness. And in honor of October's arrival, Doug brings some fear-related trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/overcoming-fears-with-farnoosh-torabi-1417 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much should personal passion factor into our choice of job/career/professional pursuit? Is it acceptable to be content with going after a sweet stack of Benjamins, even if the way you earn them doesn't align with your passion? Why do we have to choose between success and passion? Joining us today to tackle the money or passion debate is thought leader, Fortune 500 member, entrepreneur, and passion advocate Liz Elting. She'll help us learn how we can influence our career paths so that it aligns more with our passions. In our headline, we see evidence of a cooling off rental market (finally). We dive into the repercussions for renters, landlords, and the economy as a whole. In our Haven Lifeline segment, we take a call from Christine in Seattle about opening investment accounts for minors - and what special considerations, if any, there are if a non-parental, non-guardian relative wants to help the minor open it. Finally, Doug chips in with some space-related trivia. It's guaranteed to be out of this world! FULL SHOW NOTES: https://www.stackingbenjamins.com/passion-business-liz-elting-1417 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How is your thinking plan looking? Is it all clear skies and amber waves of grain? Or is it a pollution-riddled smog alert experienced during rush hour in LA - if it were next to an erupting Mt. Saint Helens? Joining our roundtable is Elaine King, a Peruvian-born CFP® who practices financial planning in Miami. She joins our regular contributors - Paula Pant who is currently located in Manhattan, New York, and Len Penzo who is still somewhere in a bunker below the Los Angeles pollution. They'll debate what ways we can use to combat the pollution that obstructs the view of our financial future. We'll talk about how we have to be aware of both internal and external sources of financial pollution and how we can combat all pollutant threats - how our mindset impacts our view of finances as well as how external factors do. In addition to cutting/controlling expenses, we dive into how earning more money - and the mindset shift that needs to happen within you - is an important factor in cleaning up what pollution is mucking up your financial outlook. What time pollution sources are impacting your life that, if better handled, could clear up a lot of the smog that blocks your financial future? In the second half of our discussion, we'll talk about how integrating the right risk-management strategy is one big, often undervalued, way to clean up the pollution that obscures your financial view. We'll talk about what insurances are essential, and what probably aren't worth it. Also, what investments and investment strategies could be adding to the pollution that contaminates your financial view? What about our tax planning strategies? What screams pollution louder than taxes? Stick around for Doug's trivia relationship-based trivia when we discuss one big way to pollute the air in your happy union. Will Elaine do OG solid and pull out the W? Will Paula continue her miracle run? Will Len bore us amaze us put his happy marriage with the honeybee in danger with his dominance of dating app knowledge? Be sure to tune in to find out! FULL SHOW NOTES: https://www.stackingbenjamins.com/friday-roundtable-financial-pollution-with-elaine-king-1415 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much of your own emotions and energy go into your financial decisions? Dr. Julia DiGangi joins Joe to chat about how to master your emotions and maximize your energy. She teaches us how to recognize stress triggers so you can control your emotions and energy before they get out of hand. What proactive steps can we take to master our emotions? She will help each of us self-analyze our relationship with money - the emotional energy and emotional relationship. What would our money say about you and how you treat it? What kind of energy and emotions are you treating it with? In our headline, we look at an encouraging trend in minority populations in the US with regard to how many people are working with financial professionals. We'll throw out the Haven Lifeline to Mark who has a question about target-date funds. Plus, Doug may or may not try to pull a fast one on us with his American history-themed trivia. FULL SHOW NOTES: https://www.stackingbenjamins.com/Emotions-and-energy-investing-dr-julia-digangi-1414 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you ready to maximize your confidence and unleash your inner bad bitch (even if you're a guy)? Today's interview with certified and self-proclaimed bad bitch Lisa Carmen Wang, and it's one you do not want to miss if you're looking to achieve more self-confidence to accomplish your dreams in relationships, career, and life. She dives into her story of self-discovery and how she built unbreakable habits that allowed her to tune out her critics and focus on being her best self. Lisa's book, The Bad Bitch Business Bible: 10 Commandments to Break Free of Good Girl Brainwashing and Take Charge of Your Body, Boundaries, and Bank Account, is the guide you need to become the unbreakable bad bitch in your life, career, and finances. You'll learn some of Lisa's invaluable life lessons that you can directly apply to your own life today to attain more confidence in yourself. From how you invest in yourself, your skills, your business, and your self-growth to how you exude your own confidence in all your interactions with others, Lisa's book will help you take stock of your daily mental routines and help you make improvements to your thoughts - which will result in improvements in your life. In our headline, we talk about a piece from the Wall Street Journal about how to maintain harmony with your significant other by planning the perfect money date. Plus you won't want to miss out on Doug's Olympic-themed trivia! FULL SHOW NOTES: https://www.stackingbenjamins.com/bad-money-b-with-lisa-carmen-wang-1413 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Taylor Swift made even more headlines when she decided to sidestep traditional Hollywood studios and distribute her new movie, filmed as part of her Eras Tour, directly to movie theaters and millions of her adoring fans. What does Taylor know that the rest of us should about the value added by so-called middlemen? Joining us for this special roundtable discussion, we welcome back author and advisor Eric Brotman who joins Paula Pant and Len Penzo. In the second half of show, sponsored by DepositAccounts.com, we dive into in what cases hiring an advisor makes sense and what traits to look for when searching for an advisor. Be sure to stick around for the thrilling continuation of our year-long trivia competition. Doug has some 90s-sitcom-themed trivia on deck. Does this spell disaster for Paula? Or will she shock us all and extend her lead as we head into the final week of September? FULL SHOW NOTES: https://www.stackingbenjamins.com/friday-roundtable-taylor-swift-1412 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You have one money-making engine that's greater than all of the rest: you. Many of us duct tape our health, popping pills for symptoms and covering up the root causes of our energy depletion. Burnout shows itself in a myriad of ways, and today Dr. Neha Sangwan dives into the clues that you just might be burning the candle at both ends. We talk about stages of burnout, identifying how we got to burnout, and what we can do to quell the problem once and for all. We talk about the stages of burnout, the horrible ways we neglect ourselves, and how to write a prescription for a better bill of health that will help us not only avoid future burnout, but thrive. In our headline segment, a recent Wall Street Journal piece purports to list where you should put your money now that interest rates are higher. Does it matter that rates are higher? Have your goals changed? We just might have an issue with this premise today...something that you rarely hear from us, I know. Plus, we throw out the Haven Life line to a lucky Stacker in need of help AND Doug provides another dose of his incredible trivia. You can never get burnout from that! Enjoy! You'll find show notes at https://www.stackingbenjamins.com Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Imagine that you JUST figured out what the financial independence movement is all about. You've been saving, but doing nothing exotic. You earlier had thought that putting money in the stock market was "gambling," like many people do. Today, though, you figure out that you've not only done a great job of making your dreams come true, but you've achieved financial independence, and you're still in your 40's. How happy would you be? Today we're live from Camp FI (camp financial independence), where a group of like-minded people are hanging out for a weekend talking about values, money, and pushing themselves to live a congruent lifestyle. Not only will we tell Jaylyn's story of surprisingly reaching his next phase of life, but so much more. Past guest Dan Sheeks joins Joe and special guest host Roger Whitney (Retirement Answer Man podcast), to share details of his group dedicated to helping young entrepreneurs and savers find each other. Not only does Dan explain what's special about these young achievers (usually between ages 18 and 25), but we get to meet two of them! Mia and Adrian both share their stories of struggle and success, with lessons that apply to all of us, whether you're working for "the man" or trying to reach financial independence by starting a business of your own. We'll also throw things back to Doug at the halfway mark for our trivia segment. While THAT segment isn't about financial independence per se, it IS a look into an area of finance you may not have thought about previously. Financial independence, entrepreneurship, live radio, and trivia? I know! Pinch us! Enjoy! FULL SHOW NOTES: https://www.stackingbenjamins.com/stories-from-camp-fi-1411 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

What could be better than clearing clutter and saving money at the same time? And just in time for the upcoming holiday season! Maybe you'll end up with more cash in your pocket to get through the traditionally rough holiday season with more money in your pocket. On today's special roundtable discussion, we dive into an article about what you can avoid buying and reduce clutter. We're joined by Columbia Magazine recipient and Afford Anything's creator, Paula Pant; Bunker Quarterly recipient and creator of the award-winning blog lenpenzo.com, Len Penzo; and Mr. "I only read the articles" and co-host of this here podcast, OG. Of course, to clear clutter, they each recycle copies of their favorite papers! In the second half of the show, you'll hear the dramatic finale of our clutter-clearing debate. Tempers are guaranteed to flare, feelings will be disregarded, and a certain podcast host's decency will be brought into question. It's just another game show episode of the Stacking Benjamins show! Finally, stick around for our intense year-long financial nerd trivia! No clutter clearing is required here. With Paula and Len tied for first place for the past few weeks, will one of them finally break the tie and claim sole possession of first place? Will O "Do you believe in miracles?" G continue his improbable comeback and force the field into a 3-way tie? Tune in and find out! Join us for fun to clear the clutter in your brain! Before you know it, you'll be selling that old NordicTrack and jumping on the "let's save money" train! FULL SHOW NOTES: https://www.stackingbenjamins.com/save-money-and-declutter-roundtable-1408 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Trading time for money. Most of us do it. In fact, before financial revolutionary Vicki Robbin (find her on past episodes), the practice was even more prevalent. Chad Carson is a real estate investor who believes that if you're building a pile of assets, often less can be more (especially if it's slightly hands-on like real estate). Using his own journey and real-life examples of other people, Chad talks us through the "trading time for money" connundrum, and hopefully helps us that Go Big or Go Home may not be the only approach to living your life. We even talk trading time for money in our headline today. Amazon and other companies are calling people back to the office. Many are fighting this, wishing to spend their career at home. If that's you, what do you do? Do we work better in the workplace or from home? We debate this (heatedly) on today's episode. How about someone who wasn't trading time for money? We'll cover that in Doug's trivia segment. Before players were paid, they had to find their own way...and we bring you a question about the Heisman Trophy in honor of football season kicking off. And, to keep the "trading time for money" trend going...today's anonymous caller traded time for money which included a pension! She wonders if she should take a lump sum or the money monthly...and of course, we have thoughts to help her. I think we have a theme! Trading time for money may not be the best path toward your goals, and today we hope you begin thinking how to exit that approach to life. Thanks for hanging out with us! FULL SHOW NOTES: https://www.stackingbenjamins.com/coach-carson-1408 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are you ready to get intimate? Really intimate? Bare it all and totally expose yourself with your partner? We're jumping into financial bed with Erin Skye Kelly to learn about the relationship-saving power of scheduling regular "naked money meetings." Rather than sliding the uncomfortable conversations under the rug, Erin shows us how to confront the topic and overcome you and your partner's money blocks and win together. Take Erin's Naked Money Quiz for free to get real with yourself and face your money blocks. In our headlines segment, we hear about the next best thing since sliced bread...or not...in the form of a spot Bitcoin ETF, possibly coming soon to a broker near you. Bitcoin is an incredible world-changing technology, but does a Bitcoin-based ETF deserve a place in your financial portfolio? We dig in. Doug brings the heat with his old-school gaming-themed trivia question. And Stacker Zachary ("Stackery"?) has a question for us about the worst advertisements ever. FULL SHOW NOTES: https://www.stackingbenjamins.com/getting-financially-intimate-with-erin-skye-kelly-1407 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

On today's evergreen Friday roundtable rewind episode from August 21, 2020, we dive into doing financial fitness exercises to build better money habits with the Financially Savvy Latina herself, Natalie Torres-Haddad. Also joining us is Richard Simmons, showing us all the Financial Fitness exercises, opps no it is the creator of the award-winning blog lenpenzo.com, Len Penzo; and our co-host-with-the-most and CFP, OG. You'll want to tune in to reinforce the importance of integrating good money habits (aka the financial fitness exercises) in your life. Plus, our friend, the Evil HR Lady Suzanne Lucas joins us to talk about how to use your vacation days guilt-free. The show originally aired in 2020 so ignore any mention of current events. Check out the original show notes here. FULL SHOW NOTES: https://www.stackingbenjamins/friday-roundtable-financial-fitness-rewind Deeper dives with curated links, topics, and discussions about all things financial fitness are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder how real estate investors reach the summit of success? Our friend and regular Friday roundtable contributor, Paula Pant, joined Joe and Crystal Hammond on the most recent episode of our sister show, Stacking Deeds, Building a Strong Real Estate Foundation: Tips for Novice Investors with Paula Pant. Paula opens up to Joe to share her journey from the early days of starting in real estate investing to where she is today. All Stackers can learn valuable lessons about smart real estate investing by tuning into this special rewind episode. Paula's real estate investing course for beginners, Your First Rental Property, is now open for enrollment for a limited time! Take the first step in your real estate investing journey by signing up for Paula's course through our exclusive link, stackingbenjamins.com/paula to get access to Joe's special "Sherlock Holmes sheet," which can help you find extra money in your budget. FULL SHOW NOTES: https://www.stackingbenjamins.com/rewind-paula-pant-real-estate-journey-1405 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Join us for a special Rewind Week edition as we check in with Crystal Hammond and our sister show geared toward real estate investing, Stacking Deeds! She sits down with the best carpenter in the remodeling business, Mark Ellison, to dive into not just real estate topics, but key takeaways about the importance of relationship-building that you, our Stackers, can apply to your own lives. FULL SHOW NOTES: https://www.stackingbenjamins.com/stacking-deeds-020-rewind-1404 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Are your household finances running like a well-oiled machine? Does each member of the household know his or her role(s) in reaching your own financial planning strategies? Who's your family's CFO? Who's got the COO role? Joining our roundtable to discuss financial planning strategies, we welcome Lacey Langford from the Military Money Show, PLUTUS award-winner Len Penzo from lenpenzo.com, and our own guy who knows how to run efficient systems, OG. In the second half of the show, our panelists share some of their favorite tools and strategies for maintaining harmony with their partners. What financial planning strategies do they talk about during their family meetings? I mean... they're experts, aren't they? What do THEY do that we can emulate? And finally, you won't want to miss the latest addition to our ongoing year-long quest for trivia supremacy. Sure it may not be financial planning strategies that you'll hear, but WILL be a race to the golden end-of-year trophy. Will Lacey's return be history in the making by helping Team Paula take sole ownership of first place? Will seniority reign supreme in the form of Len reclaiming the lead? Will OG continue his improbable ascension from the depths of the cellar? Three will enter; only one will emerge victorious! FULL SHOW NOTES: https://www.stackingbenjamins.com/family-money-roles-1403 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever wonder what personal finance topics worry everyone else? You're not alone. We all wonder if our view of the world (and personal finance, by extension), are the same that other people hold. That's why today we're live from the floor of the 2023 Podcast Movement Conference with two other great podcasters: Shannah Game from Everyone's Talkin' Money and Paula Pant from Afford Anything. Both Shannah and Paula, along with our own OG share their take on how our audience worries have changed this year. We tackle every personal finance topic from inflation to employment to interest rates...and more. But that's not all of the personal finance fun. We kick it back to Doug, who's holding down the fort in mom's basement for us, with a trivia question that you just might get right... Truly the takeaway from this year's version of what's become an annual episode for us? It's that while personal finance is truly personal, it turns out that the one constant is that the world always is changing, and if something seems like a "sure thing," it's sure to become unsure at some point. In one discussion, the conversation moves to inflation, which three years ago wasn't even on the radar as a hot topic. Today, inflation is driving many of the worries that we have, from interest rates to real estate prices. It's true that the world of personal finance only has a few topics to master, and yet, staying on top of them so that you make better decisions is always more challenging (and yes, sometimes even fun!) than you may think. FULL SHOW NOTES: Add show notes url here. Be sure to please include https://www at the beginning of the show notes url that makes it clickable on YouTube Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices