Sophia Amoruso is the Founder of Nasty Gal and Trust Fund, an early stage venture capital firm.We talk through her journey of starting Nasty Gal as an Ebay store in 2006 to sell vintage clothing, bootstrapping it to $28 million in revenue, raising $50 million, scaling it to $120 million and a massive team, turning down a $400 million acquisition offer, and ultimately declaring bankruptcy.She takes us inside what it was like to fail so publicly, what she’d do differently next time around, lessons from building the brand, and why she started her VC firm Trust Fund to back the next generation of founders building consequential companies.Thank you to Numeral, Flex, Amplitude, and Merge for supporting this episodeNumeral: The end-to-end platform for sales tax and compliance https://www.numeral.comFlex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFzAmplitude: AI analytics, all you have to do is ask https://www.amplitude.comMerge: Every modal. One API. Total control. Check out Merge Gateway https://www.merge.dev/gatewayTimestamps:(0:59) Selling vintage on Ebay while working at an art school(04:31) Lessons in marketing and perceived value(12:38) Knowing when to make your first hire(18:31) Borrowing from others to build a unique brand(25:17) Growing to $120m revenue in seven years(27:24) Sharing the pitch deck that raised $50m(30:17) Mistakes scaling to 100’s of employees too fast(34:48) Downsides of raising at too high of a valuation(39:56) Why being a CEO is fun(42:57) Declaring bankruptcy(50:38) How it feels to fail publicly(54:41) Writing a book, Netflix series, starting the Girlboss movement(59:13) How to create a new brand in 2026(1:05:34) Starting Trust Fund to invest and help founders(1:13:45) Raising $5m from a poker game(1:18:47) Sophia asks for Turner’s LP pitch(1:26:53) Traits of the best foundersTrust Fund: https://www.trustfund.vc/Pitch Trust Fund: https://www.trustfund.vc/pitchesNasty Gal: https://www.nastygal.com/Follow SophiaInstagram: https://www.instagram.com/sophiaamorusoTwitter: https://x.com/sophiaamorusoLinkedIn: https://www.linkedin.com/in/sophiaamorusoWebsite: https://www.sophiaamoruso.com/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Nikhil Basu Trivedi and Mike Smith are the Co-founders of Footwork where they invest up to $15 million in Seed and Series A rounds. This is the first time they've ever sat down to record a conversation together on video.We talk about starting the firm in 2020, their secret sauce for working with founders, lessons investing in Canva’s Seed round, scaling Stitch Fix from $0 to $1B revenue in five years with $17m in capital, why AI will enable a new wave of entrepreneurship, and how public company boards are discussing AI today.Thank you to Tony Staehelin, Andrew Riesen, and Hunter Walk for helping brainstorming topics for the conversation.Thank you to Flex for supporting this episode.Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:24) Starting Footwork from a tweet in 2021(3:11) Difference between startup and public company boards(4:52) 20-40% of board meetings are now about AI(7:48) How Footwork’s investing in AI today(10:37) AI will enable millions of new entrepreneurs(15:04) 37 questions to ask when starting a VC firm(17:40) Importance of differences(23:08) The pace of VC is faster than operating(26:26) Footwork’s secret sauce (2x board seats, 1-pager)(31:59) Investors should talk to and help employees(37:05) Building an equal-carry partnership(39:33) How Footwork makes decisions(43:21) Navigating short-termism and politics in VC firms(51:18) “You’re only as good as your next investment”(53:30) Characteristics of great founders(58:13) Canva’s Seed pitch in 2014(1:02:54) Joining Stitch Fix as 4th employee(1:06:40) Scaling Stitch Fix $0 to $1B revenue in five years with $17m in capital(1:16:48) Raising from Bill Gurley after a failed Series A(1:19:40) Footwork’s office near YC(1:22:10) Opportunities in consumer health(1:25:20) Using flash mobs to win deals(1:26:15) Dad lifeReferencedFootwork: https://www.footwork.vc/Anything: https://www.anything.com/Table22: https://www.table22.com/Canva: https://www.canva.com/Stitch Fix: https://www.stitchfix.com/Honeydew: https://www.honeydew.com/Follow MikeTwitter: https://x.com/msmith492LinkedIn: https://www.linkedin.com/in/michaelcsmith1Follow NikhilTwitter: https://x.com/nbtLinkedIn: https://www.linkedin.com/in/nikhilbtSubstack: https://nbt.substack.com/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Chris Hladczuk is the Co-founder and CEO of Hanover Park, the AI-native fund administrator, vertically integrating fund administration, portfolio management, and LP experience for finance and investment teams.Chris is the 2nd ever returning guest of the show, and is fresh off announcing Hanover’s $27m Series A. We go inside the round, their explosive growth, why they built their own general ledger from scratch, and how that enabled them to build incredible AI products for investment firms that touch over $100 trillion in assets.Thanks to Sahil Bloom, and Chad + Pratyush at Susa for help brainstorming topics for this conversation.Thank you to Numeral and Flex for supporting this episode.Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.comSign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:37) Financial infrastructure for investment firms(1:35) Hanover Park’s $27m Series A(5:30) AI-enabled services businesses(9:07) Productizing the service layer(11:30) Helping CFO’s and investors use AI(13:46) Building a general ledger from scratch(18:03) Compete against companies with IT departments(19:55) Hiring in an unsexy industry(21:30) Live in constant paranoia of your customers(25:19) Gongs, music in the office, blizzard commutes(28:54) Friday night hackathons(30:54) Automating onboarding and manual admin work(35:05) Real-time visibility on all data(38:07) Always get on the plane(40:36) Turning customers into raving fans(43:45) Using polite persistence in sales(47:36) How to master founder-led content(51:29) 99% of advice is wrong in AI era(54:21) Importance of one-way vs two-way doors(56:11) Growing from VC into PE and Private Credit(1:00:36) When to turn down new customers(1:02:22) Becoming a customers most important vendor(1:04:00) Chris’ personal AI stack(1:07:41) Hanover Park’s MCPReferencedTry Hanover Park: https://www.hanoverpark.com/Careers at Hanover Park: https://jobs.ashbyhq.com/hanover-parkFirst episode with Chris: https://www.youtube.com/watch?v=7lomqcrFNv8Artie: https://www.artie.com/Episode with Jacqueline @ Artie: https://www.youtube.com/watch?v=6fd1YKsBaq0Granola: https://www.granola.ai/Claude Cowork: https://claude.com/product/coworkHubSpot: https://www.hubspot.com/Attio: https://attio.com/Monaco: https://www.monaco.com/Follow ChrisTwitter: https://x.com/chrishladLinkedIn: https://www.linkedin.com/in/chris-hladczuk-b09204153Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Scott Stevenson is the Co-founder and CEO of Spellbook.Spellbook is an AI copilot for contract review and drafting, essentially “Cursor for lawyers.” They have 4,000 customers in 80 countries, and to my knowledge is the fastest growing AI company in Canada, and the largest company in the world built on a Microsoft Word plugin.Scott has been building in legal AI longer than almost anyone. We talk about why legal software was essentially untouched before LLM’s, why the market is so hot right now, if it’s sustainable, and how Spellbook navigates product differentiation compared to horizontal AI products like ChatGPT.We talk about why fine-tuning your own models was one of the biggest mistakes early AI companies made, how to build a network effect as a vertical AI product, and Spellbook’s philosophy of “Don’t sharpen your axe when the chainsaw is coming out tomorrow”.Spellbook spent a few years finding PMF before really taking off in 2022, and Scott shares their playbook for launching over 100 product experiments in three years, how to know when to lean in, and what it’s been like scaling Spellbook post-PMF.Thank you to Numeral and Flex for supporting this episode.Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.comSign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:30) Spellbook: “Cursor for Contracts”(3:08) Building the world’s largest Microsoft Word plugin(14:06) Why legal software was untouched before LLMs(18:32) $30 trillion moves through contracts annually(20:51) Why ChatGPT won’t replace vertical tools(25:15) Fine-tuning was the biggest mistake in AI(30:00) Differences between pro and amateur gamers(37:38) Top-down vs. bottoms-up in legal AI(42:27) The long-tail of legal AI software(47:24) Building for models that don’t exist yet(51:20) Skating where the puck is going(1:01:35) The legal bill that cost 50% of his bank account(1:09:33) Testing 100 landing pages in 3 years(1:14:06) The moment Spellbook hit PMF(1:19:17) Building new brands for each product experiment(1:23:10) Raising a Series B with a tweet(1:27:41) What Scott learned from Keith Rabois(1:31:16) Scott's favorite new AI toolReferencedSpellbook: https://www.spellbook.legal/Careers at Spellbook: https://www.spellbook.legal/careersPlaying to Win by David Sirlin: https://www.amazon.com/Playing-Win-becoming-David-Sirlin/dp/1413498817Find the Fast Moving Water by NFX: https://www.nfx.com/post/find-the-fast-moving-waterSpellbook’s case study with Replit: https://replit.com/customers/spellbookTwin: https://twin.so/Follow ScottTwitter: https://x.com/scottastevensonLinkedIn: https://www.linkedin.com/in/scottasBlog: https://blog.scottstevenson.net/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Chetan Puttagunta is a General Partner at Benchmark.We talk about investing in Manus, the AI company that went from zero to $100M ARR in eight months and was recently acquired by Meta.We also talk through the full history of application software, from mainframes to client-server, to the internet to cloud, why each wave reduced the barrier to entry and created an explosion in the number of new software, why legacy SaaS companies are making the same mistake on-prem vendors made at the dawn of the cloud, why software companies should be making big AI acquisitions, and how public market investors are begging private AI companies to go public.We also talk about what Benchmark actually looks for in founders, how they make decisions, and why his last two investments were consumer AI and crypto.Thanks to Sam Ross and Everett Randle for helping brainstorm topics for this conversation.Thanks you to Numeral and Flex for supporting this episode.Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.comSign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:08) Inside the $2.5B Manus acquisition(6:24) Manus' three main use cases(11:08) Taking heat on Twitter(15:10) Starting to tweet about software in 2018(22:50) The history of application software(29:15) Benchmark’s 25x Fund 7(31:33) SaaS incumbents got too dominant by 2020(31:48) Going all-in on AI software in 2022(39:31) Benchmark didn’t invest in the big AI labs(40:48) How cloud companies beat on-prem competitors(44:33) Why AI companies will beat legacy cloud competitors(50:04) Software incumbents should make big AI acquisitions(57:35) Why incumbents have not bought more AI companies(1:04:43) Public markets are starving for AI companies(1:10:14) Inside Benchmark’s fund strategy(1:14:14) Benchmark’s history of non-traditional VC rounds(1:17:56) Is the 20% ownership model outdated?(1:19:20) Chetan’s rebirth as a consumer investor(1:22:39) What Benchmark looks for in founders(1:25:01) AI coding and gross marginsReferencedBenchmark: https://benchmark.com/Eric Vishria’s podcast episode: https://www.youtube.com/watch?v=I-5IsqFgrZMWorkday S-1: https://www.sec.gov/Archives/edgar/data/1327811/000119312512375787/d385110ds1.htmInnovator's Dilemma: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Business-Essentials/dp/0060521996Try FOMO: https://apps.apple.com/us/app/fomo-never-miss-out/id6741115427Follow ChetanTwitter: https://x.com/chetanpLinkedIn: https://www.linkedin.com/in/chetanputtaguntaFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Jake Stauch is the Co-founder and CEO of Serval. Serval automates IT with AI.We talk taking on incumbents with an AI-native product, why IT departments haven’t had much automation historically, the 12+ month journey of landing their first customer, and how teams can increase talent density as they scale.Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com⁠](https://www.numeral.xn--com-xw0a/)Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:14) AI-native employee support(5:15) How an early work trial almost ended the entire company(9:05) Why IT hasn’t had much automation(13:09) Vibe coding for IT professionals(15:31) Competing against publicly traded incumbents(23:32) Having less than three months of runway for seven years building his first hardware consumer health startup(33:15) Lessons from five years at Verkada(39:11) The single question that led birthed the idea for Serval(44:19) Navigating 12+ months of zero revenue(52:05) Knowing when not to pivot(55:15) Finally landing the first three customers(58:07) Getting pre-empted for a Series A(1:01:04) Getting a Series B term sheet the next day(1:05:54) How to structure design partnerships that convert(1:08:48) Building a mirror instead of system of record(1:13:49) Make the implementation part of the product(1:15:24) How to increase talent density as you scale(1:21:32) Why every new hire should help you recruitReferencedTry Serval: https://www.serval.com/Careers at Serval: https://www.serval.com/careersEpisode with Filip @ Verkada: https://www.youtube.com/watch?v=fXI3GdicIHwFollow JakeTwitter: https://x.com/jakeservalLinkedIn: https://www.linkedin.com/in/jakestauchFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Gary Tan is the President and CEO of Y Combinator.YC is the startup accelerator behind companies like Airbnb, Stripe, Coinbase, Reddit, Twitch, and thousands more. According to Garry, they’ve invested in 20% of all startups worth $5B or more started since 2012.Gary has lived every side of the YC ecosystem. He went through YC as a founder, later became a partner, started Initialized Capital where he backed companies like Coinbase and Instacart, and then returned to lead YC.We walk through the different “eras” of YC, from the early Paul Graham and Jessica Livingston days in Cambridge, to scaling in San Francisco, to today’s push back toward in person community and what Gary calls “founder mode” for the organization itself.We also talk about why the Bay Area still matters so much for startups, what’s happening with California taxes and policy, and why Gary has gotten more involved in local politics to keep it the best place for founders to build companies.Then we go deep on the parts of startups people don’t talk about enough. Co-founder conflict, rage quitting, therapy and coaching, and why companies inevitably take on the personality and emotional patterns of their founders.We also cover what YC looks for in applications, how the 13 week batch is structured, how Demo Day really works, how to choose the right investors, and what Gary thinks the next phase of YC looks like, including helping founders even after Series A.At the end, Gary shares his personal AI workflow, including meta prompting, comparing outputs across models, and the tools he uses every day to think and build faster.Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:05) Moving from Winnipeg to California as a kid(1:35) How YC interviews work(2:55) The first batch in 2005(6:46) Why YC moved from Boston to SF(8:17) California’s Billionaire Tax(11:00) Tech should care about public policies(17:01) Going direct to your audience(20:28) The 2nd Era of YC(24:01) Rage quitting Palantir, learning to understand himself(32:41) Co-founder conflict kills most startups(35:15) Joining YC as a group partner(37:22) Initialized Fund 1 (55x DPI)(39:44) Why Garry went back to lead YC(42:44) YC funds 20% of all $5B+ companies(44:30) Lessons from Brian Chesky(48:01) Garry’s thoughts on YC rejection(51:41) How to get into YC(58:03) What it’s like inside a 13-week YC batch(1:02:23) 20% of YC is hard tech(1:05:55) YC's 3rd era: founder mode, re-batching(1:07:56) Escaping the matrix(1:11:26) Garry's personal AI stack(1:20:25) Tech optimismReferencedY Combinator: https://www.ycombinator.com/Initialized Capital: https://initialized.com/Torch: https://torch.io/Perplexity: https://www.perplexity.ai/Anthropic: https://www.anthropic.com/OpenAI: https://openai.com/Airbnb: https://www.airbnb.com/Kyle Vogt on his new startup: https://www.youtube.com/watch?v=XQoFbvyWEy8Follow Aaron Levie on X: https://x.com/levieFollow GaryTwitter: https://x.com/garytanLinkedIn: https://www.linkedin.com/in/garytan/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Miranda Nover is the Co-founder and CEO of Fort Health. Fort builds wearables that automatically track strength training for people who care about longevity.This is a new format I’m experimenting with. It’s the first time I’ve had a Banana portfolio company founder on the show while they’re still at the pre-seed stage. When I surveyed my subscribers a few weeks ago, you were most interested in more early stage VC-backed founders, and I’d love your feedback on what you think of this.Miranda is still very much working through the idea maze and iterating on the Fort product. We talk about the megatrends driving consumer health, why she’s building a company that helps people get stronger, and everything she’s learned getting a hardware company off the ground.She’s also in the middle of the current YC batch, and gives an inside look at what it’s been like and if she’d recommend it to other founders.Thank you to Numeral and Flex for supporting this episode.Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.comSign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(3:37) Importance of strength training(6:34) Benefits of being strong(10:37) Evolution of Fort’s hardware(15:58) Automating workout tracking(19:29) Two types of strength trainers(25:30) Building the strength company(27:26) How healthcare is consumerizing(40:43) Lessons building batteries at Tesla(44:56) Hardest parts about building a hardware startup(51:01) Adventures in vibe coding(57:54) How to use Twitter as a founder(1:02:09) The launch video industrial complex(1:08:03) What it’s like doing YC(1:10:19) Selling crayons in 3rd grade, Lemonade stands(1:14:41) Miranda’s best vintage finds(1:16:44) How Turner evolved as a VC(1:22:22) Turner’s early social media PMF(1:28:53) Inventing shitpostingReferencedTry Fort: https://www.fort.cx/Follow MirandaTwitter: https://x.com/mirandanoverLinkedIn: https://www.linkedin.com/in/mirandanoverFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Dug Song and Jon Oberheide are the co-founders of Duo Security.If you’ve never heard of Duo, it might be one of the most underrated software stories of all-time.Starting in 2010, they burned only $14 million to hit $100m in ARR, were acquired by Cisco for $2.35 billion in 2018, and now rumored to be doing over $1 billion in ARR inside Cisco 16 years later.We talk about how they built one of the most capital efficient SaaS companies ever from Ann Arbor, Michigan, and how their focus on the customer and company culture helped them win in a crowded cybersecurity market.We talk growing up in the early hacking culture of the 90s, why most security tools are painful to use, sizing their market, solving for non-consumption of a product, and how Duo flipped the model by designing for end users instead of security teams.We talk about staying in Michigan instead of moving to Silicon Valley, and why staying out of the tech bubble helped them execute.We break down the mechanics of scaling from zero to $100 million in ARR, everything they learned integrating with Cisco, and why more founders should build outside of San Francisco. A quick thank you ex-Duo employees Zack Urlocker, Ash Devata, and Katie Kilroy for their help brainstorming topics for the conversation.Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com](https://www.numeral.com/)Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(4:49) Meeting from Dug’s Wi-Fi honeypot(7:33) 90’s hacking culture and cybersecurity’s wild west(14:49) How the internet was born in Ann Arbor(18:58) Staying in Michigan instead of moving to Silicon Valley(31:20) Philosophy on leadership and team building(39:48) What makes a good engineering leader(44:01) Starting Duo to make security easier(45:22) Why most security products suck(48:36) How fixing account takeover became a $1B ARR company(59:10) TAM, competition, fixing the non-consumption of security(1:04:04) Being a radical advocate for the customer(1:08:35) Duo’s pizza sales play(1:12:45) Branding lessons from Anthropic, Tesla, Cliff Bar(1:17:47) When to say no to customers(1:21:27) Importance of culture when scaling(1:27:56) Duo’s role in uncovering the SolarWinds breach(1:31:29) Scaling to $100M ARR on $14M burned(1:39:30) Inside the $2.35B Cisco acquisition(1:44:02) What big companies get wrong about customers(1:51:53) Building Michigan’s startup ecosystemReferencedDuo Security: [https://duo.com](https://duo.com/)Cisco: [https://www.cisco.com](https://www.cisco.com/)University of Michigan: [https://umich.edu](https://umich.edu/)Follow DugTwitter: https://x.com/dugsongLinkedIn: https://www.linkedin.com/in/dugsongFollow JonTwitter: https://x.com/jonoberheideLinkedIn: https://www.linkedin.com/in/jonoFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Jacqueline Cheong is the Co-founder and CEO of Artie.Artie moves data across your systems in real-time, and we talk about why that’s so important in the age of AI.It’s a lot harder than you’d think, as less than 5% of real-time data streaming projects are successful.I talked to a dozen people to prepare for this conversation, including Jared Friedman who worked with Jacqueline during YC, her sales coach Ras, and numerous Artie employees like A-nee-rud, Ryan, Sarah, Shangbing and Jacqueline’s co-founder Robin.We talk through how Robin built real-time data streaming at OpenDoor and Zendesk before they started Artie, and Jacqueline shares the sales playbook she learned going from hedge fund analyst to software CEO, including asking customers for their hardest problem and then solving it with the product.Artie just announced a $12 million Series A a few weeks before we published this episode. We talk about how they landed all of their early enterprise customers through cold outbound, how they structure and automate their prospecting with AI so they have no BDRs, and why they’re seeing customers switch to Artie even after building their own multi-million dollar real-time streaming projects in-house.I also asked Jacqueline what it’s like working with Standard Capital. They’re a new fund started by a group of YC partners, and it was fascinating to hear about the things they’ve borrowed from YC when investing at the Series A stage.Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(4:08) Artie: Real-time data streaming(5:13) Why moving data is so hard(9:14) Evolution of data warehouses(12:47) AI needs real-time data(18:44) Build vs buy in data streaming(22:51) How to build in a crowded market(26:26) Early focus on a specific hard problem(30:33) Acquiring enterprise customers from cold emails(32:51) Onboarding their first customer with no UI(35:46) Solving compliance and implementation(38:50) How to automate internal engineering, marketing, and ops(44:01) Building an AI-powered GTM pipeline and motion(46:52) Add your customers on iMessage, Slack, Teams(53:00) Starting Artie to solve their own problem(59:25) Discovering YC through a friend(1:02:20) Everything Jacqueline learned about sales(1:06:29) How to improve your sales discovery calls(1:10:08) Inside Artie’s $12m Series A(1:16:44) What its like working with Standard Capital(1:22:59) Jacqueline’s favorite bookReferencedTry Artie: https://artie.comCareers at Artie: https://www.artie.com/careersClay: https://www.clay.comPodcast with Tommy @ Alloy: https://www.youtube.com/watch?v=e7i8Wxklu-YYCombinator: https://www.ycombinator.comStandard Capital: https://www.standardcap.comFounding Sales: https://www.foundingsales.comThe Score Takes Care of Itself: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472Follow JacquelineTwitter: https://x.com/JacquelineSYC19LinkedIn: https://www.linkedin.com/in/jacqueline-cheongFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Nathan Benaich is the founder of Air Street Capital and author of the State of AI report. On its eighth year, the report is a year-long effort on the biggest things happening in AI, across research, industry, politics, and safety.This episode covers the biggest takeaways from the latest report, like the rise in reasoning, the surge in China’s open source models, where AI is working in practice, the rise of sovereign AI, where he thinks value will actually accrue over the long-term, if we’re in an AI bubble, and how he’s investing in AI today at Air Street.Thanks to Nico at Adjacent and Dan at Michigan for helping brainstorm topics for Nathan.Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(3:39) State of AI 2025(6:22) Takeaway #1: Reasoning & tool calling(13:01) Takeaway #2: Rise of Chinese open source(15:25) Open vs closed source models(26:46) Takeaway #3: AI revenue is real(27:51) Takeaway #4: Sovereign AI(36:44) Are we in an AI bubble?(59:23) Starting Air Street Capital(1:05:18) Raising Fund 1(1:16:20) Air Street portfolio strategy(1:25:15) When and who Nathan decides to invest(1:35:04) How important are AI benchmarks?(1:39:31) When to train your own models(1:45:56) Rise of European defense tech(2:01:43) Nathan’s personal AI stack(2:07:32) Is niching down too risky?(2:16:12) Nadal vs FedererReferencedState of AI Report: https://www.stateof.aiThe Thinking Game Documentary: https://www.youtube.com/watch?v=d95J8yzvjbQV7: https://www.v7labs.comFollow NathanTwitter: https://x.com/nathanbenaichLinkedIn: https://www.linkedin.com/in/nathanbenaichFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Marcelo Lebre is the Co-founder and President of Remote, the payroll and international employment company.Remote is one of today's most underrated software companies. We get into why payroll is such a hard problem, why most of the industry still runs on spreadsheets, the edge cases of software meeting government, and a diagnosis of Europe’s regulation problem.We also talk through the journey trying 8 different startup ideas before Remote, how COVID changed the business overnight, and what he’s learned about building culture and running remote teams.Thanks to Gillian O’Brien, Villi Iltchev, Andreas Klinger, Masha Bucher, and Marcelo’s co-founder Job for helping brainstorm topics for this.Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(3:22) Gaming with kids(6:05) Hundreds of millions in revenue in the most boring market(8:22) Payroll corporate spies(14:54) Why payroll tax is such a hard problem(19:46) Why tax is even more complicated outside the US(23:08) Legacy payroll still runs on manual spreadsheets(29:14) Remote’s unfair advantage in AI(31:40) Building the global payroll API that didn’t exist(38:06) Meeting his co-founder on a double date(42:04) Seven years of failed products before Remote(49:25) Launching Remote in 2019(52:39) Each year felt like a new apocalypse(59:25) Distributed teams must master async, document everything(1:02:42) Culture is what you tolerate(1:13:05) Europe's regulation problem and why it can't innovate(1:21:18) Why fundraising is so hard in Europe(1:28:23) Deleting spreadsheets to force automation(1:40:25) Burnout, health, fixing the system instead of grinding harder(1:47:57) Writing honestly about the hard parts of building companiesReferencedTry Remote: https://remote.com/Careers at Remote: https://remote.com/careersRemote Handbook: https://remotecom.notion.site/a3439c6ccaac4d5f8c7515c357345c11?v=8bb7f9be662f45da87ef4ab14a42be37The Toyota Way: https://www.amazon.com/Toyota-Way-Management-Principles-Manufacturer/dp/0071392319The Book of Five Rings: https://www.amazon.com/Book-Five-Rings-Miyamoto-Musashi/dp/1590309847Follow MarceloTwitter: https://x.com/marcelolebreLinkedIn: https://www.linkedin.com/in/marcelolebreFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron.Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re still early, and lessons today’s breakout AI companies can learn from those that survived the Dot Com Crash.Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at A* is invested in teenagers, and he shares how he identifies outlier talent so early, from Seed investments in Airbnb, PayPal, and Pinterest, to many of today’s hottest AI companies.He also shares the insane story of investing 100% of the proceeds from his first startup into PayPal’s Seed round, how PayPal’s early fraud systems inspired Palantir, what he learned from the PayPal Mafia, from Peter Thiel, and what makes Founders Fund special.We also talk about how he and his wife recently had two babies, five months apart, using genome screening and surrogates.Thanks to Ramtin Naimi, Navya Gudimetla, and Bennett Siegel for helping brainstorm topics for the conversation.Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(4:25) Power shift from VC’s to founders since the 90’s(9:08) AI is the mother of all bubbles(12:40) Why AI is still underhyped(14:10) What Kevin and A* are investing in today(16:02) Investing 100% of his first startups proceeds in PayPal’s Seed round(21:21) What made the PayPal Mafia special(23:37) Parallels between the 90’s and today(26:40) What makes Founders Fund special(35:07) How Palantir evolved from PayPal’s fraud models(39:06) Building Xoom on the PayPal API(43:38) Lessons between Kevin’s 1st and 2nd startups(46:52) Starting Eventbrite off early PayPal API app(51:51) Eventbrite’s hidden TAM challenge(53:49) Selling Eventbrite to Bending Spoons(54:59) Investing 20% of A* in teenage founders(1:02:33) Incubating Sauron, the home security company(1:08:44) Making breakfast for our kids(1:13:33) Having kids with genome screening and surrogates(1:20:31) Collecting art, how to get startedReferencedhttps://www.a-star.co/https://www.eventbrite.com/https://www.xoom.com/https://www.sauron.systems/https://www.orchidhealth.com/Setting the Table by Danny Meyer: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/006074276320% of fund in teenage founders: https://techcrunch.com/2025/10/18/this-top-vc-bet-close-to-20-of-his-fund-on-teenagers-heres-why/https://nypost.com/2025/12/14/us-news/xu-bo-chinese-billionaire-reportedly-sires-more-than-100-kids/Follow KevinTwitter: https://x.com/kevinhartzLinkedIn: https://www.linkedin.com/in/hartzFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Jason Calacanis is the host of the All-In Podcast, This Week in Startups, co-founder of the Launch Accelerator, and the “3rd or 4th investor in uber”.We go inside the origins of All-In, how they decide what to talk about each week, and if Jason thinks it helped swing the election.We also talk lesson from starting 7 media companies over the past three decades, what he's learned from studying the world's best interviewers, joining Sequoia’s first scout program, his investing strategy at Launch, the story of being the “3rd or 4th investor in Uber", what people underestimate about Elon, and what it was like inside the Twitter buyout in 2022.Thank you to Austin Petersmith for helping brainstorming topics for the conversation.Thanks to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠Timestamps:(3:34) Interviewing lessons from Oprah, Charlie Rose(6:48) How to ask good questions(12:20) Jason’s favorite upcoming podcasters(17:57) Starting 7 media companies(22:50) How he'd start a new media company today(27:56) In-person experiences, “Bang Bang” in Japan(32:44) Vinyl bars, smartphones, mental health(38:41) Origin of the All-In Podcast(42:58) All-In’s influence on the 2024 Election(46:58) Why All-In got so political(52:35) Media lessons from Trump(55:01) Joining Sequoia’s very first scout program(57:55) Jason’s VC investing strategy(1:03:55) How Launch competes with other accelerators(1:08:46) Fundraising is a numbers game(1:13:06) Investing in Uber and Robinhood Seed rounds(1:18:31) Origin of “3rd or 4th investor in Uber” meme(1:20:57) How Jason got the first Model S(1:26:19) What people underestimate about Elon(1:27:37) Inside the Twitter takeover(1:31:44) Career advice for young people(1:35:22) Jason’s experience taking GLP-1’s(1:40:05) How All-in picks topics each weekReferencedHowie: ⁠https://howie.com/⁠All-In Podcast: ⁠https://allin.com/⁠Bret Easton Ellis (Podcast): ⁠https://www.breteastonellis.com/podcast⁠Red Scare (Podcast): ⁠https://en.wikipedia.org/wiki/Red_Scare_(podcast)⁠Preet Berrara (Podcast): ⁠https://cafe.com/stay-tuned-podcast/⁠Adam Friedland Show: ⁠https://www.youtube.com/c/TheAdamFriedlandShow⁠The Insider (Movie): ⁠https://www.imdb.com/title/tt0140352/⁠Launch: ⁠https://www.launch.co/⁠Ro: ⁠https://ro.co/⁠Follow JasonTwitter: ⁠https://twitter.com/Jason⁠LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis/⁠Follow TurnerTwitter: ⁠https://twitter.com/TurnerNovak⁠LinkedIn: ⁠https://www.linkedin.com/in/turnernovak⁠Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it

Steven Fabre is the Co-founder and CEO of Liveblocks.Liveblocks builds ready-made AI copilots and collaboration for your product, and Steven is one of my smartest friends on how people are actually using AI on a day-to-day basis.We talk about what most people get wrong when trying to build AI-native software, how to treat it as more than just a copilot that sits on top of your product, and what he’s learned about how large enterprises are actually buying and using AI right now.We also talk through Liveblocks journey of evolving from real-time human collaboration components into one that also incorporates AI, what he’s learned going from a designer to a CEO, and how he rebuilt the company after his co-founder stepped away.Thank you to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠Timestamps:(2:17) Liveblocks: Infrastructure for people + AI(6:08) Wrong ways to add AI to software(8:05) Why humans and AI must collaborate(12:35) How AI will change software UI(18:58) AI search optimization(26:20) How to get #1 on Product Hunt(32:33) Liveblocks 1.0 to 3.0 evolution(36:40) Why collaboration software is so hard(38:38) How customers use Liveblocks(42:36) Hiring a coach to get better at sales(47:07) Steven’s biggest enterprise sales mistakes(50:28) How AI changes GTM and funding milestones(57:57) Going from a designer to a CEO(1:01:06) How Liveblocks first started(1:04:56) Importance of design in company building(1:06:51) Learning to become a CEO(1:12:29) When his co-founder left 5 years in(1:15:49) Becoming stronger hiring a new Head of Engineering(1:22:10) Remote culture: what doesn’t work(1:24:08) Remote culture: what does work(1:26:47) Importance of autonomy on remote teams(1:28:05) Most underrated basketball players(1:33:38) ACL injury that kickstarted his first businessReferencedLiveblocks: https://liveblocks.io/Careers at Liveblocks: https://join.team/liveblocksFollow StevenTwitter: https://x.com/stevenfabreLinkedIn: https://www.linkedin.com/in/steven-fabre-5510bb38Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Zaid Rahman is the Co-founder and CEO of Flex.Flex is the AI native private bank for high net worth middle market business owners, headlined by it’s 60-day interest free credit card for businesses.Flex just announced their $60 million Series B, as well as their new consumer product, Flex Elite, which pits it head-to-head against Amex for the consumer spending of some of the wealthiest people in America. It's products now spans from when a business owner first generates revenue, all the way to when they spend that cash personally.This conversation goes inside how the company scaled from zero to a $70 million revenue run rate in two years, and everything Zaid learned along the way.Thank you to Eric Bahn at Hustle Fund, Jeff Morris Jr. at Chapter One, Andrew Ziperski at General Catalyst, and Jared Thomas and Ewan Steel at Flex for helping brainstorming topics for the conversation.Timestamps:(1:44) Raising $60m to fix business finance(3:23) Flex Elite: Personal + Business banking(4:48) Jumbo shrimps: powering 40% of US payroll(9:16) The forgotten mid market business(14:01) “Flex fuels ambition”(16:08) How to serve entrepreneurs in middle America(22:58) Flex’s 5-pillar product suite(27:12) Starting Flex to help construction companies(31:51) Using AI to lend to mid-market customers(40:22) Power of multi-product in fintech(43:53) Zero to $3B in volume in 18 months(44:43) Raising a bear market Series A in 2023(51:00) How referrals landed their first big customers(55:07) Flex’s playbook for 85% organic growth(1:01:15) Dissecting various accents(1:04:22) Building a quiet luxury brand(1:09:33) Importance of customer happiness(1:12:43) Why CEO’s should be the top sales person(1:13:58) Building lots of in-house software(1:24:33) PMF is like operating a popular restaurant(1:30:49) How to raise a debt facility(1:34:48) Recruiting is so crucial for startups(1:39:00) Why VC’s hate lending businesses(1:45:14) Underserved vs Underbanked in fintech(1:48:02) Why business owners want personal + business banking(1:54:49) Acquiring Maza, leaning in to M&A(2:02:53) Most fintech companies look the same(2:08:35) Founder group therapy with Eric at Hustle Fund(2:11:50) The Thiel Fellowship’s 10% unicorn hit rate(2:15:52) Lesson from the ruler of Dubai(2:19:24) Building Flex’s risk underwriting engine(2:26:58) Flex’s AI opportunityReferencedTry Flex: https://www.flex.oneCareers at Flex: https://jobs.lever.co/Flex/Basel III https://en.wikipedia.org/wiki/Basel_IIILinguistic TikTok account: https://www.tiktok.com/@zaydupreeLazy luxury: most worn shoes on private jets: https://www.wsj.com/style/fashion/lazy-luxury-sneakers-are-these-the-most-worn-shoes-on-private-jets-7801be30Follow ZaidTwitter: https://x.com/zaidrmnLinkedIn: https://www.linkedin.com/in/zaidrahmanFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Matteo Franceschetti is the Co-founder and CEO of Eight Sleep.Eight Sleep created one of the original breakout consumer health products in 2014, quietly building a business that’s raised over $300 million dollars and was reportedly free cash flow positive in the first half of 2025.But things weren’t always easy, and Matteo shares the challenges of starting a hardware company, why hardware has stronger moats, and the fundraising mindset he adopted that eventually got Khosla Ventures and Founders Fund to invest.We also get into the importance of sleep, how the company’s Sleep Butler uses AI to help you sleep better, and the big opportunity building more consumer health products.Thanks to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠Timestamps:(2:18) Three pillars of health: sleep, nutrition, fitness(4:02) Creating a sleep routine(6:59) Importance of body temperature in sleep(8:43) How Eight Sleep works(12:14) Using AI to help you sleep(18:35) The AWS outage(24:12) It’s too hard to build in Europe(28:09) Why hardware has stronger moats(32:23) How to fundraise for a hardware company(35:30) The opportunity in Sleep tech(38:43) Hiring is easy when you have a mission(40:37) How to fight jet lag(43:03) Opportunities in women’s health(45:54) Evolving from single purchase to subscription model(47:12) Matteo’s personal health stack(49:41) Racing sports carsReferencedEight Sleep: https://www.eightsleep.com/Compliant VC Meme Account: https://x.com/compliantvcFollow MatteoTwitter: https://x.com/m_franceschettiLinkedIn: https://www.linkedin.com/in/matteofranceschetti/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Rahul Vohra is the Founder and CEO of Superhuman Mail.Rahul sold his company to Grammarly in July of 2025, which had just acquired Coda in 2024. Following the acquisitions, the combined companies rebranded to Superhuman in October of 2025.And it’s quietly one of the most underrated businesses that no one is talking about, with over $700 million ARR and 40 million Daily Active Users. Grammarly spent 15+ years building integrations with over a million other products, that they’re now layering more AI products on top of.We talk about Rahul’s journey building Superhuman, go inside the acquisition, all the lessons he’s learned from selling two companies, why you should design your product like a video game, and we also re-visit his famous quantitative guide to finding PMF.Thanks to Todd Goldberg, Ed Sim, Shomik Ghosh, Ryan Hoover, and Rahul’s brother Gaurav Vohra for helping brainstorm topics for this conversation.Thank you to Hanover Park for supporting this episode! Upgrade your fund admin to the 21st century https://www.hanoverpark.com/TurnerTimestamps:(2:42) Inside the Superhuman acquisition(11:09) Grammarly: $700M ARR, 40M DAUs(18:53) How to sequence your product roadmap(24:43) Vision for the new Superhuman(32:43) Build your product like a video game(38:24) Designing Karamja island in Runescape(41:10) Build products like toys and games(44:53) Starting a Machine Learning PhD in 2006(48:49) Dropping out to start his first company(50:47) Rapportive’s crazy accidental launch(57:56) Meeting Superhuman co-founders(1:02:17) Being 1 of 20 to access LinkedIn’s API(1:06:38) Almost getting acquired by LinkedIn(1:10:32) Nearly dieing, getting acquired with 2 weeks of runway(1:20:08) Diligence from VCs vs Acquirers(1:26:37) Rahul’s quantitative framework for PMF(1:30:45) How to build an enduring brand(1:31:51) Rahul’s AI-powered productivity stack(1:35:01) Todd and Rahul’s angel fund(1:36:45) We need more solo foundersReferencedSuperhuman: https://www.superhuman.comGrammarly: https://www.grammarly.comHigh Resolution Fundraising: https://paulgraham.com/hiresfund.htmlHigh Resolution Fundraising: https://paulgraham.com/hiresfund.htmlSuperhuman Quantitative Framework for Finding PMF: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/Whisper Flow: https://wisprflow.aiFollow RahulTwitter: https://x.com/rahulvohraLinkedIn: https://www.linkedin.com/in/rahulvohra/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Will Gaybrick is the President of Technology and Business at Stripe.Stripe builds financial infrastructure for the internet, and if you’ve ever purchased a product online, you’ve probably used Stripe.We talk about what Stripe’s doing in crypto and stablecoins, how AI is changing commerce and payments, how they’re thinking about going public, how they build products internally, and interesting data they’re seeing around AI-native companies, like how they’re growing 3.5x faster than SaaS companies.Thank you to Claire Hughes Johnson, Josh Kushner, and Cosmin Nicolaescu for help brainstorming topics for the conversation.Thank you to Numeral and Amplitude for sponsoring this episode.Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://www.numeral.comAmplitude: Listen to users at scale with AI https://www.amplitude.com/AI-FeedbackTimestamps:2:42 Will’s promotion5:29 Build vs Buy in AI6:39 Inside the Bridge acquisition8:54 Stripe’s stablecoin strategy11:20 Why building Stripe is so complicated13:22 How Stripe builds new products18:29 AI companies growing 3.5x faster than SaaS22:58 New fraud vectors in AI businesses25:19 Agentic commerce in ChatGPT29:34 Building modular products34:05 How Stripe uses AI internally42:12 Building the first payments foundation model48:23 Link, Stripe’s 200M user consumer product56:52 Will Stripe ever IPO?59:14 Blurring of private and public companies1:03:39 Starting Hack Yale1:08:23 Joining Thrive’s $5 million Fund 11:12:30 Low margin businesses are underrated1:16:30 Joining Stripe as CFO1:21:59 How Stripe’s go-to-market has evolved1:25:56 Stripe’s margins1:29:52 Why financial services are so hard to use1:33:04 Lessons from Alan MulallyReferencedStripe: https://stripe.com/Careers at Stripe: https://stripe.com/jobs/searchFollow WillTwitter: https://x.com/gaybrickLinkedIn: https://www.linkedin.com/in/william-gaybrick-5730347Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Roger Ehrenberg is the Co-founder of Game Changers Ventures and IA Ventures.We talk about the current Seed stage venture environment, what he learned investing in sports teams, how COVID changed sports, what he’s investing in today, characteristics of the top founders, advice for emerging managers, and his real estate and consumer brand projects in Detroit.Thank you to Michael Kim, Jon Oberheide, Jesse Beyroutey, James Fitzgerald, Dan Feder, Sarah Smith, Marc Weisser, and Charles Hudson for help brainstorming topics for the conversation.Thank you to Hanover Park for supporting this episode. Upgrade to an AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:3:45 Current Seed stage market7:17 Starting Game Changers to invest in sports 12:25 Investing in the Miami Marlins16:45 Investment opportunities in sports18:21 Tomorrow Golf League23:54 Investing in sports teams25:50 Business models in sports27:12 Importance of real estate development, gambling32:53 How COVID changed sports38:41 Clippers experimenting with cheap tickets & concessions41:51 Opportunities monetizing super fans46:51 Sports as an investable venture asset53:24 Great founders find big TAMs56:31 The desire to win58:09 Sending letters to break into Wall Street from Michigan1:02:38 Raising IA Ventures Fund 1 in 20091:07:58 Advice for emerging managers1:13:18 The Trade Desk’s three bridge rounds1:18:03 Lessons on recycling capital1:20:16 What it’s like working with your kids1:24:53 Brand Detroit1:29:14 Being world class at multiple disciplinesReferencedGame Changers Ventures: https://gamechangers.vcIA Ventures: https://www.iaventures.comEberg Capital: https://www.ebergcapital.comTGL Golf: https://tglgolf.comBrand Detroit: https://www.branddetroit.comFollow RogerTwitter: https://x.com/infoarbitrageLinkedIn: https://www.linkedin.com/in/rehrenbergFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Daksh Gupta is the Co-founder and CEO of Greptile, the AI code reviewer that understands your entire code base.Greptile just closed a $25M Series A led by Eric Vishria at Benchmark, and we get into their long and winding journey to build one of the fastest growing AI companies.Thanks to Suds at SF1 for helping brainstorm topics for the conversation.Thank you to Numeral and Hanover Park for sponsoring this episode.Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelHanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:(3:15) Evolution of AI coding + code review(11:23) Coding will never be fully automated(18:07) Why you need a separate code reviewer(24:34) How eng teams adopting AI is changing(27:37) Why LLM costs will come down(31:54) Pricing AI products(35:27) Getting your team to adopt AI(38:17) How Daksh started the 996 discourse(42:10) Recruiting is a funnel, open roles are a product(49:19) Making an energy drink for programmers(51:19) Brainstorming marketing stunts(57:22) Don’t do hype marketing too early(59:41) Starting a band, hitting #14 on Spotify(1:06:35) Evolution of the startup meta(1:12:39) Starting Greptile in class at Georgia Tech(1:19:18) Moving to SF, getting into YC(1:23:44) Pivoting from codebase chat to code review(1:27:09) Crazy growth and mimetic desire(1:29:47) Pricing AI software(1:34:44) How to market developer tools(1:39:46) Greptile's fundraising journey(1:42:57) Why YC is worth the 7% dilution(1:46:39) Treat fundraising like datingReferencedGreptile: https://www.greptile.com/Careers at Greptile: https://www.greptile.com/careersMonetizing Innovation: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867Greptile Work Culture: https://www.greptile.com/blog/work-cultureEpisode with Adit @ Reducto: https://youtu.be/h98dLRJFHMMFollow DakshTwitter: https://x.com/dakshgupLinkedIn: https://www.linkedin.com/in/dakshg/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Sign-up here to get weekly episodes + transcripts in your inbox: https://www.thespl.it/Adit Abraham is the Co-founder and CEO of Reducto. Reducto’s product takes PDFs and physical documents, and extracts all the data, just like a human would if they were reading it.At the time of recording, they’ve processed over 1 billion pages, grew 6x over the past five months, and are fresh off a $75 million Series B led by a16z. And Adit told me they’ve only burned $1 million of capital so far to get here.And the craziest part, Adit told me they’ve only burned $1 million of capital so far to get here.Anyone building an AI product probably sees Reducto as essential infrastructure. Our conversation gets into how they built the best product in the space, landing a Fortune 10 customer as a two-person startup, getting to $1 million in ARR within a few months, lessons doing founder led sales to over $5 million in ARR, and what the future of PDF’s, and human / computer data looks like.Thank you to Liz Wessel at First Round, Chetan Puttagunta at Benchmark, and Adel Wu at Reducto for helping brainstorm topics for Adit.Thank you to Numeral and Hanover Park for sponsoring this episode.Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelHanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:(3:35) Reading unstructured human data(10:44) Growing 5x in four moths(12:38) Insurance, healthcare, legal, logistics(19:13) Where LLM’s still struggle(28:23) Starting Reducto from a blog post during YC(32:01) Landing a Fortune 10 customer with two people(35:48) Limiting the product and growth early on(40:57) Getting an MIT professor fired(43:50) How to avoid pivot hell(49:00) $108M from First Round, Benchmark, a16z(51:48) Chetan convincing them to raise a Series A(55:50) Raising a Series B in 48 hours(59:36) Redeye flight to hire the 1st AI researcher(1:05:42) Lessons hitting $5m ARR with founder-led sales(1:13:09) Staying on top of changes in AI modelsReferenced:https://reducto.aihttps://reducto.ai/careersFollow AditTwitter: https://x.com/aditabrmLinkedIn: https://www.linkedin.com/in/aditabrahamFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSign-up here to get weekly episodes + transcripts in your inbox: https://www.thespl.it/

Erik Bernhardsson is the Co-founder and CEO of Modal, building high-performance AI infrastructure.We talk about building what is essentially a new cloud provider, created from the ground up, optimized for AI. We also talk about what actually happened with the great GPU shortage, how Modal fixes the inference problem in AI, and why he thinks AI will lead to 10x more developers.He also shares lessons on culture from joining Spotify as the 40th employee, treating hiring like a prediction problem, what most people get wrong working with early customers, why more people should start companies in their 30’s and 40’s, and reflections on fundraising in a hot market.Thank you to Tim Chen at Essence Venture Capital and Erik’s Co-founder Akshat for their help brainstorming topics for this conversation.Thank you to Meow and Hanover Park for supporting this episode.Meow: Get free bookkeeping for your startup at https://www.meow.comHanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:(4:26) Modal: AI-native infrastructure(9:02) Why its so hard to get GPU’s(15:00) Hitting PMF with AI generated media(20:37) Competing in IOI competitions(23:09) 40th employee at Spotify(27:17) Lessons from Spotify(31:17) Starting Better[dot]com(34:05) Treating hiring like a prediction problem(36:12) Erik’s favorite interview question(39:07) Sales + common design partner mistakes(42:02) Startups should solve hard problems(44:05) Evolution of Modal’s product over time(50:15) Rise in importance of inference in AI(52:07) AI development post-GPU scarcity(58:51) Building a brand in dev tools(1:04:31) Fundraising from Seed to Series B(1:07:42) More 30+ year old’s should start companies(1:10:00) Reducing developer tax, increasing productivity(1:20:37) Why Erik’s bullish and bearish on AI(1:26:17) Bubbles, downsides to inappropriate valuations(1:34:58) High CO2 levels make you dumb(1:37:38) Difference between US and European startupsReferencedModal: https://modal.comCareers at Modal: https://jobs.ashbyhq.com/modalSuno: https://suno.comPlanet Scale: https://planetscale.comHow to hire smarter than the market: https://erikbern.com/2020/01/13/how-to-hire-smarter-than-the-market-a-toy-modelInterviewing is a noisy prediction problem: https://erikbern.com/2018/05/02/interviewing-is-a-noisy-prediction-problemCloud in 2030: https://erikbern.com/2021/11/30/storm-in-the-stratosphere-how-the-cloud-will-be-reshuffledFollow ErikTwitter: https://x.com/bernhardssonLinkedIn: https://www.linkedin.com/in/erikbernFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Austin Petersmith is the Co-founder and CEO of Howie, the AI secretary.We talk about why AI assistants are so hard to build, why they decided to build Howie super narrow, and everything that went into their brand, name, and viral launch.Thank you to Adam D’Augelli, Sophia Amoruso and Alex Cohen for help brainstorming topics for the conversation.Thank you to Hanover Park for supporting this episode. Try the modern, AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:(3:35) Howie: The AI Secretary(6:08) Why AI assistants are so hard to build(16:19) Why Howie started in email(20:49) Adding a human in the loop(30:48) AI software vs AI-powered humans(36:21) How a meme inspired Howie(39:29) Inside the making of Howie’s launch video(44:15) Howie’s viral launch video + Discussion(53:47) Designing the brand(1:01:37) Long-term opportunity and roadmap(1:07:53) Working for Jason Calacanis(1:12:00) Jason's media lessons(1:16:51) Getting Howie's first users(1:19:35) Pitch deck strategy that raised $6m(1:24:09) The mistake of optimizing for growth too soon(1:29:48) Building an AI company outside of SF(1:33:13) Being Superhuman’s 1st customer, Mercury’s 3rdReferencedTry Howie: https://howie.com/Jobs at Howie: https://app.dover.com/jobs/howieHowie Dewitt Meme: https://knowyourmeme.com/memes/howie-dewittNewKid: https://newkid.services/Follow AustinTwitter: https://x.com/awwstnLinkedIn: https://www.linkedin.com/in/awwstnFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Chris Frantz is the Co-founder and CEO of Loops, the email platform for software companies.We get into why sending emails is still a big problem, his hilariously simple framework for building products, getting in to YC with a last minute application, and why they skipped raising a Series A.We also talk through Chris decade of working in marketing, like when to lean into PLG vs Sales vs hype led growth, early stunts they did to get their first users, why they do no marketing now, and why Loops’ customer support team is all engineers.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/TurnerTimestamps:(4:37) Email for software companies(8:28) Why email is a big deal(14:05) The future of email(17:00) Product vs Sales vs Hype led growth(24:33) Coming up with the idea for Loops(29:36) Building one of the first GPT wrappers in 2020(34:34) Lessons selling his first company(37:13) Doing their YC app in 10 minutes(40:53) Avoiding VC’s who add value(46:58) Skipping a Series A(51:37) Building in stealth for 18 months(53:21) Marketing stunts to get the first waitlist sign-ups(58:44) Four step cadence of building Loops(1:01:58) Personally onboarding every new customer(1:04:03) Balancing 996 with family(1:11:11) Cleaning wasp nests with a shop vacReferencedLoops: https://loops.soCareers at Loops: https://loops.so/careersCuriosity: https://curiositystream.comSnazzy AI / Unbounce: https://unbounce.com/product/smart-copyAtlas customer support: https://atlas.soFollow ChrisTwitter: https://x.com/frantzfriesLinkedIn: https://www.linkedin.com/in/ctfrantzFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Dan Gray is the Head of Insights at Equidam.If you’re a tech and investing nerd like us, you’ll love this conversation. We cover everything Dan’s learned reading dozens of academic research papers on startups and venture capital, debunking many popular narratives of the industry.We talk about the dangers of pre-mature startup scaling, the importance of origination stage investing, the concept of startup catering and why so many startups look the same, and the role of mega funds play in the ecosystem.We also discuss what the data says about concentration vs diversification, what VC’s get wrong about pattern matching, and why pivoting is more valuable than you thinkThanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Harmonic - The startup discovery engine https://harmonic.ai/turnerTimestamps:(6:43) What’s the required rate of return in VC?(9:29) Venture capital needs new definitions(16:10) QSBS(18:23) Are we in an AI bubble?(24:07) Re-branding early and late stage venture(28:25) We need more origination stage capital(40:05) Survivorship bias in emerging manager outperformance(42:57) Incentives driving larger fund sizes(48:10) Raising overvalued rounds re-risks a startup(52:08) Startup catering: why all startups look alike(58:42) Are VC mega funds still an experiment?(1:08:06) Late stage VC is competing with PE(1:13:42) a16z’s Fund 1 strategy(1:18:18) How diversified should VC funds be?(1:25:06) Performance of Generalist vs Specialist firms(1:30:35) How to value a startup(1:40:58) Why VC firm location correlates to returns, but startup location does not(1:44:05) Founder background doesn’t predict success(1:48:27) Startups with one pivot are most successful(1:50:24) Premature scaling kills 70% of startups(1:54:47) Does mega fund model work for origination investing?(1:56:15) Value of Twitter and writing onlineReferenced Research PapersVenture Predation: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4437360Process Alpha: https://angelspan.com/process-alpha-how-to-construct-and-manage-optimized-venture-portfolios-joe-milam-journal-of-portfolio-management-august-2022/The Sunk Cost Fallacy in VC: https://www.sciencedirect.com/science/article/pii/S0929119924000518Predictably Bad Investments in VC: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4135861Startup Catering to Venture Capitalists: https://afajof.org/management/viewp.php?n=58968Premature Scaling: https://innovationfootprints.com/wp-content/uploads/2015/07/startup-genome-report-extra-on-premature-scaling.pdfReferenced BooksThe Otherland Tetrology: https://www.goodreads.com/series/43762-otherlandPermutation City: https://www.goodreads.com/book/show/156784.Permutation_City?from_search=true&from_srp=true&qid=lf7FuUR9se&rank=1Necromancer: https://www.goodreads.com/book/show/6088007-neuromancer?ref=nav_sb_ss_1_29Other Referenced ItemsQSBS changes: https://www.dwt.com/blogs/startup-law-blog/2025/07/qsbs-big-beautiful-bill-tax-code-upgradesMega funds and the great re-risking: https://nextview.vc/blog/megafunds-and-the-great-re-risking/Rex Woodbury’s post on hot companies: https://www.digitalnative.tech/p/the-taxi-cab-theory-of-venture-capitalThe VC Performance Paradox: https://www.linkedin.com/pulse/performance-paradox-venture-capital-dan-gray-2fqrePrior episodes mentionedDan Feder: https://youtu.be/_Ou6D9PLSBIMichael Dempsey: https://youtu.be/UzSbG6DL8CMSolugen: https://youtu.be/ofkNiB2nI3QFollow DanTwitter: https://x.com/credistickBlog: https://credistick.comFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Dan Feder is a Senior Managing Director of Investments at the University of Michigan’s $18 billion endowment.Our two hour conversation talks through the past, present, and future of all things venture capital, and investing more broadly.Dan lays out the case for why most institutional investors should change how they approach asset allocation, why risk and uncertainty are not the same, the importance of relevance and independent thinking, advice for fund managers raising from institutional LP’s, the trend of VC’s rolling up services businesses, and what he learned from beating Lance Armstrong in a race.Thanks to Chris Douvos @ Ahoy Capital and Adam Kurkiewicz at WashU for their brainstorming topics for Dan!Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/TurnerTimestamps:(5:50) Beating Lance Armstrong in a race(8:05) “The will to win is nothing without the will to prepare”(10:39) Why investors need to re-think asset allocation(22:31) Difference between risk and uncertainty(29:26) How endowments work(33:12) Endowment portfolio construction(40:47) From law, to industrial buyouts, to venture(49:13) Narrowing scope to increase returns(54:54) Why career planning as an LP is hard(58:24) VC in the 00’s(1:08:18) Venture vs Adventure Capital(1:15:16) VC’s rolling up legacy industries(1:20:17) Importance of relevance(1:26:25) Traits of the top investors(1:28:25) Importance of trust in institutional LP fundraising(1:32:54) Venture is the most competitive ass class(1:35:37) Why venture firms do not persist over time(1:38:27) How venture will change going forward(1:43:37) The Newman CycleReferencedA Sense of Where You Are by John McPhee: https://www.amazon.com/Sense-Where-You-Are-Princeton/dp/0374526893Risk Uncertainty and Profit by Frank Knight: https://www.amazon.com/Risk-Uncertainty-Profit-Frank-Knight/dp/1614276390Follow DanTwitter: https://x.com/federdanLinkedIn: https://www.linkedin.com/in/danfederFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Eoghan McCabe is the Co-founder and CEO of Intercom, building Fin.ai, the AI customer service company.This was an extremely candid, two hour conversation going inside every detail of how Intercom was the first late stage software company to successfully re-architect itself to be AI-native.Intercom just announced they’ve built their own customer service-focused AI models, and Eoghan explains why most software companies will have to do the same.We also talk through the lessons he learned coming back to run Intercom in 2022 after stepping back in 2020, why many AI companies have strong negative gross margins despite the narrative, how Intercom designed AI’s first outcome-based pricing model, the challenges of buying AI software today, the importance of brand when building new products, and we get in the wayback machine, talking through the pain raising Intercom’s initial million dollar Seed round, and how venture capital has changed since then.Thank you to Eoghan’s Co-founder Des Traynor for helping me brainstorm topics for the conversation.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTimestamps:(4:18) We’re at peak SaaS(9:11) Inside early days of Intercom’s turnaround(16:43) AI will beat humans at everything(21:17) Making trade-offs building AI products(24:25) Why Intercom trained their own AI models(28:33) Lessons from returning as CEO(34:19) Overcoming initial AI skepticism in 2022(40:02) Creating AI’s first outcome-based pricing(45:15) Intercom’s best-in-class gross margins(49:25) Why its so hard to buy AI software today(51:28) Unpacking AI’s negative gross margins(58:12) Being perfectly positioned for AI(1:09:47) Why AI products need their own brand(1:16:13) Founder CEOs vs Manager CEOs in AI(1:21:29) AI startup opportunities(1:24:57) Lessons running a team in Dublin and SF(1:28:25) How media has changed over time(1:37:32) Raising Intercom’s first $1 million Seed round(1:43:53) Why there are so many VC’s(1:47:38) Advice for investorsReferencedIntercom: https://www.intercom.com/Fin: https://fin.ai/Intercom Careers: https://www.intercom.com/careersEoghan’s website: https://eoghanmccabe.comIntercom’s first pitch deck: https://www.slideshare.net/slideshow/intercompitchdeckpdf/253317574Follow EoghanTwitter: https://x.com/eoghanLinkedIn: https://www.linkedin.com/in/eoghanmccabeFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Albert Azout is the Co-founder and Managing Partner of Level Ventures, combining first-principles thinking with state-of-the-art data science to back and build top seed-stage firms and their breakout companies.Venture investing is hard, and this conversation covers all their research unpacking exactly how to generate alpha.We also talk about how Level picks and backs emerging venture managers to invest in, and Albert gives a demo of the custom internal software they’ve built.Thank you to Jake Kupperman, Sasha Kaletsky, Nathan Benaich, Amanda Robson, and Dave Fontenot for helping brainstorm topics for the conversation. Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/TurnerTimestamps:(5:01) Top 3 forms of alpha in VC(10:11) Other ways to generate alpha(12:47) Avoiding false positives(17:11) Optimal fund size and portfolio construction(22:25) The role of Luck(23:55) Spin-out vs outsider funds(25:43) Level’s backchannel reference process(29:29) Finding alpha in Criticality Investing(34:45) Why capital flows drive all returns(43:53) Early, consensus investing has the most alpha(48:46) Networks are more persistent than performance(52:03) The strongest and weakest networks(58:41) Demo of Level’s internal software(1:04:48) Building a Fund of Funds around their data(1:10:01) Ideal LP GP relationship(1:12:39) Benchmarks are relative(1:15:39) VC funds using AI(1:17:43) How venture will change in the next 10 yearsReferencedLevel Ventures: https://levelvc.com/Level’s Research Papers: https://levelvc.com/research/Follow AlbertLinkedIn: https://www.linkedin.com/in/albertazout/Newsletter: https://albertazout.substack.com/ Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Will O’Brien is the Co-founder of Ulysses, building autonomous, low cost robots for the ocean.Will considers the ocean humanity’s next great frontier. It makes up over $2.5 trillion of economic activity, considering things like fishing, aquaculture, shipping, mining, communications infrastructure, and defense. Yet we know more about the surface of the moon’s of Saturn than we do the bottom of our own ocean.We talk about Ulysses first product, restoring plant life in the ocean, their modular autonomous underwater robotics platform, advice for anyone selling to governments, crazy businesses that could eventually evolve in the ocean, and why the way we finance startups needs to change.Will also loves conspiracy theories, and we talk about some of our favorites, and why he thinks people who believe them could make good startup founders.Thank you to Will’s brother’s Harry and Jacob O’Brien, and to upcoming guest of the show Eoghan McCabe for helping brainstorm topics for Will.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTimestamps:(4:03) Peace offering of Dubai Chocolate(5:30) Modern internet theory(7:40) The ocean is the last frontier(11:53) Ulysses: read/write layer of the ocean(13:35) The $2.5 trillion ocean economy(15:14) Current ocean unit economics(18:50) Starting with seagrass ecosystem restoration(24:13) Modular, underwater autonomous robots(27:31) Starting Ulysses with a group chat(29:51) Raising a Seed from Lowercarbon with no network off a cold calendar invite(32:24) Economic use cases for ocean robotics(36:07) Spiritual energy from the ocean(42:36) First Ramp podcast ad in Irish(43:21) Floating cities, sub tours, deep sea mining, iron fertilization(51:47) $10+ billion in shipwrecked treasure(53:18 Atlantis is real(59:46) Craziest alien conspiracy theories(1:01:28) Sinking the titanic to create the Fed(1:04:19) Conspiracy theory believers are good founders(1:07:55) How to sell to the government(1:13:28) Writing a letter to an Irish billionaire(1:16:00) Finding meaning after living with Monks in Nepal(1:27:10) Why financial innovation precludes economic dominance(1:44:01) The SPV peddler business model(1:46:35) Should we bring back SPAC’s?ReferencedUlysses: https://www.ulysses.eco/Careers at Ulysses: https://www.ulysses.eco/jobsThe Richat Structure: https://en.wikipedia.org/wiki/Richat_StructureJesse Michael’s YouTube: https://www.youtube.com/@JesseMichelsBrad Jacobs: https://en.wikipedia.org/wiki/Brad_Jacobs_(businessman)Follow WillTwitter: https://x.com/willobriLinkedIn: https://www.linkedin.com/in/will0brienFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Isaac Medeiros is the Founder of Mini Katana and Kanpai Foods.Isaac’s content gets over 1 billion views per month. Our conversation gets into content strategy from a high level down to tactical decisions, differences between the TikTok and YouTube algorithms, and how AI will impact content creation.We also get into Isaac’s origin story building consumer brands, why TikTok made food an interesting category for new products, how to get a product into retail stores, and why you shouldn’t sell into retail.Isaac also shares how tariff’s impacted his company. They became unprofitable overnight, and he had to move his entire supply chain from the US to Mexico in 60 days.Thank you to Sean Frank @ Ridge and Kevin Espiritu @ Epic Gardening for their help brainstorming topics for Isaac.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here.Timestamps:(3:46) 165 million views in two days(5:15) Followers don’t matter, build a binge bank(11:21) How to monetize an audience(14:36) Identify outliers for content ideas(17:13) Should founders make their own content?(19:34) Starting Mini Katana(23:39) $10m revenue in two years w/ $0 CAC(25:56) Difference between TikTok and YouTube algorithms(29:38) When to experiment with a second platform(32:20) Starting Kanpai, a freeze-dried candy company(36:54) Why freeze-dried candy wasn’t popular(38:22) Why you shouldn’t sell in retail(41:12) Why you should sell in retail(47:05) Downsides of selling to large retailers(49:52) Should CPG brands raise money?(57:59) Moving manufacturing from US to Mexico in 60 days due to tariffs(1:04:20) Why you don’t want to be first in a category(1:08:06) Other CPG creators Isaac follows(1:09:15) Elon Musk, Charlie Munger, Mark Cuban(1:11:55) Labubu’sReferencedMini KatanaKanpai FoodsPrevious episode with Kevin EspirituPrevious episode with Sean FrankPeachy BabiesThe Marshmellow CoFollow IsaacTwitterLinkedInFollow TurnerTwitter: LinkedIn: Subscribe to my newsletter to get every episode + the transcript in your inbox every week.

Michael Dempsey is the Managing Partner at Compound, a thesis-driven, research-centric investment firm.We spent two hours talking through the past, present, and future of a bunch of topics in technology and investing.Michael started investing in AI in 2016. He was the first investor in now-unicorns Runway and Wayve. But he hasn’t done much AI investing over the past few years. We talk about why, how AI will intersect with robotics, the future of things like crypto and synthetic biology, and why so many deep tech companies mess up economic value capture.We also talk about what it means to be a thesis-driven venture firm, Compound’s research process and how to replicate it, what private and public market investors can learn from each other, advice for anyone starting in venture today, how to build a brand in VC, and why venture firms don’t compound and actually decay over time.Thank you to Kevin Kwok, Andy Weissman, Cristóbal Valenzuela, Blake Robbins, and Smac at Compound for their help brainstorming topics for this.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here.Timestamps:(4:09) Leading Runway’s Seed in 2018(10:15) Short-term ARR vs long-term sustainability(16:20) Compound, a research-centric investment firm(18:41) Investing in bio, crypto, real-world AI, and healthcare(23:58) VC firms do not compound, they decay over time(29:27) How to build a research-focused investment firm(41:30) Current state of venture slop(45:43) Building a brand as a VC firm(52:31) Investing in Wayve in 2016(58:53) Why deep tech companies screw up economic value capture(1:04:57) How to approach massive funding rounds(1:08:36) Should VCs “play the game on the field”?(1:15:33) Compound is a forecasting firm(1:21:37) Advice for young people getting into VC(1:26:48) Public market investors underappreciate narratives(1:31:20) Michael’s crypto thesis + real use cases(1:40:07) Why crypto hasn’t seen mass adoption yet(1:49:00) Humanoid robots won’t work(1:54:42) Should you make a hyped launch video?ReferencedCompound RunwayWayveMichael’s BlogFollow MicahelTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Subscribe to my newsletter to get every episode + the transcript in your inbox every week.Ryan Hoover is the Founder of Product Hunt and Weekend Fund.Ryan’s probably helped more founders launch their products than anyone else on Earth. We talk about starting Product Hunt as an email list, and he open sources the growth flywheel that propelled it to one of the most important places in technology.Ryan unpacks how he built and scaled a community around the product, how online communities have changed over time, how we’re thinking about software in the age of AI (tech will change, human behavior won’t), and how status has changed in Silicon Valley.We also talk about starting Weekend Fund to invest in other founders, his first 400x investment, investing in consumer health, and why he started investing in other funds.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 signing-up here. Timestamps:(5:52) Helping founders with software(15:36) Early ideas for Product Hunt in 2013(19:14) Starting as a social email list(26:26) Product Hunt’s growth flywheel(31:15) AI won’t change human behavior(34:12) An audience is not a community(36:42) Why every community needs utility(38:52) Communities have shifted towards group chats(40:10) How AI changes building products(49:35) Importance of craft(52:30) Starting Weekend Fund, Ryan’s 400x investment(56:57) Weekend Fund’s software experiments(59:26) What makes Ryan’s investing unique(1:02:16) Why Ryan has a small fund(1:07:41) Peptides, GLP-1’s, Ketamine(1:18:57) Investing in funds(1:20:53) Ways LPs can add value for GPs(1:23:05) How status has changed in Silicon Valley(1:31:37) Backing founders with secrets, why failing is hardReferencedWeekend FundProduct HuntWayve self-driving carsThe community trapHooked: How to Build Habit Forming ProductsGet Your Wish - Porter RobinsonSocial UtilitiesSilicon Valley’s new status symbolsSelfish InvestingFollow RyanTwitterLinkedInPersonal WebsiteSignature BlockFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Sahill Poddar is the Co-founder and CEO of Parafin, helping marketplaces, vertical SaaS, and point of sale providers offer financial services their merchants.Sahill and his team have quietly built Parafin to nearly a $100m GAAP revenue run rate in only four years, and they've done it in an industry that's become a Silicon Valley graveyard: SMB lending.Sahill talks about how they partnered with other marketplaces, vertical SaaS, and point of sale providers to offer financial services to SMBs at scale, landing DoorDash as their first customer before building the product, and advice for technical teams learning enterprise sales.Sahill's a fascinating founder, as he started his career getting a PhD discovering the Higgs boson particle at CERN’s Large Hadron Collider. We talk about physics, he explains how the Large Hadron Collider works, why physics is just real world machine learning, and all the lessons he learned on the growth teams at Facebook and Robinhood (including the way Robinhood acquired most of its userbase!)A thank you to Hans Tung at Notable Capital, Nick Shalek at Ribbit, and Mahdi Raza at Pathlight for their help brainstorming topics for the conversation.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.Timestamps:(4:06) Lending to SMBs inside marketplaces and platforms(9:39) Why SMB lending is so hard(12:50) Three ways AI is changing Fintech(16:47) Silicon Valley’s graveyard of SMB lenders(22:44) Getting a PhD in Particle Physics(26:15) How CERN's Large Hadron Collider works(31:49) Discovering new dimensions(34:10) Building billion user data sets at Facebook(39:53) Working with other physicists at Robinhood(50:29) Growth lessons from FB + Robinhood(1:00:57) Starting Parafin, embedded, horizontal SMB lending(1:06:09) Why credit is the biggest problem for SMBs(1:10:53) Raising a Seed from Ribbit pre-product(1:13:25) Landing DoorDash as the first customer(1:16:51) Mastering B2B sales as a technical founder(1:22:58) Lessons from Vlad at RobinhoodReferencedParafin:Careers at ParafinEpisode with Charley & MahdiJuliusCERNLarge Hadron ColliderFollow SahillTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Garrett Lord is the Co-founder and CEO of Handshake, the career and social network for Gen Z, connecting a million employers, 1,600 universities, and 18 million students and alumni.We talk through the explosive growth in Handshake’s human AI data labeling business, how AI is changing the job market and careers, advice for scaling a three-sided marketplace, and Garrett’s approach to hiring executive-level talent.We also get into the early days of Handshake, tapping out his dad’s retirement account to fund the first years, driving across the US landing the first customers, sleeping in McDonald’s parking lots, sneaking into careers fairs, and inside Handshake’s first fundraise that took over seven months.Shoutout to Jeff Richards, James Alcorn, Ilir Sela, and Ben Christensen for helping brainstorm topics for Garrett.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.Timestamps:(3:44) More Gen Z than LinkedIn(7:11) Helping frontier labs label AI data(14:43) Masters and PhD students flock to Handshake(16:52) Why Handshake will win in AI data labeling(19:24) Growing to $250m+ Revenue(21:56) KPIs in recruiting marketplace(24:45) How AI will change careers(33:57) How to build a Seal Team Six AI team(37:06) Interning at Los Alamos(40:00) Breaking into Silicon Valley from Michigan(44:19) Helping friends get jobs at Palantir(48:13) Driving across the US sleeping in McDonald’s parking lots(54:52) Funding early days with his dad’s retirement account(57:37) Handwriting letters to get the first six customers(1:03:06) Early product failures and iterations(1:11:01) Fundraising, crashing on couches for seven months(1:17:07) Finally closing a Seed round(1:20:05) Moving from Michigan to SF with no money(1:23:38) Importance of sequencing new features(1:29:10) Handshake’s exec recruiting process(1:32:01) Building a company with your best friendsReferencedTry HandshakeCareers at HandshakeGumloopPeter Thiel Startup SchoolPaul Graham’s blogFollow GarrettTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Jake Cooper is the Founder of Railway.This conversation explores how AI accelerates the need for strong backend infrastructure, when to build vs buy in AI software, and why there are only two moats: solving hard problems and doing hard things.We also unpack Railway’s bold product bets, like enabling creators to earn revenue with backend templates, building their own data centers, and not building their own AI models.Jake also talks about their four week new hire onboarding, how they build a problem roadmap, why operators should be managers, and why you should almost never work weekends.Thank you to Angelo Saraceno @ Railway and Erica Brescia Bacon @ Redpoint for help brainstorming topics for the conversation.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.Timestamps:(3:33) Solving the hardest problems in dev tools(8:16) Starting with the hardest thing(11:18) How AI accelerated the need for Railway(12:50) Importance of backend in AI-native software(16:52) Jake’s angel fundraise strategy(20:51) Resisting AI for so long(25:32) Using AI to get leverage(29:57) Build vs buy in AI software(33:22) When Jake knew Railway was working(34:27) Creating infrastructure templates(38:04) Building data centers and a cloud service(40:27) Two moats: Hard problems and hard things(46:25) Hitting 8-figures in revenue(48:47) Railway’s four week onboarding(54:25) Building a problem roadmap(56:16) You can’t set your own culture(1:01:58) Railway’s viral “How We Work” post(1:08:39) Using Discord instead of Slack(1:11:25) How hypergrowth companies mess up org design(1:14:03) Why you shouldn’t work weekends(1:19:45) Not betting big on AI models(1:21:53) Lessons from Zuck, Martin ScorseseReferencedRailwayCareers at RailwayThe Inward Draw of CapitalismHow We Work Volume 1Volume 2Volume 3Volume 4Follow JakeTwitterLinkedInSubstackFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Today’s guest is Matt Mullenweg, Co-founder of WordPress, which powers over 43% of all websites on the internet, and founder of Automattic.Our conversation explores the 2000’s internet, the early days of Automattic, and the decisions and philosophies that set them up for success 20 years later.We talk open source software, why Matt’s such a big proponent of it, how Automattic built its business model as one of the first SaaS companies (that now owns companies like Tumblr and WooCommerce), and how AI is changing engineering.Matt also shares how to build a community around your product, “Conscious Capitalism”, what he learned running one of the first distributed teams, and lessons on optimism from Walt Disney.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp.Sign-up for Ramp and get $250 here.Timestamps:(3:48) WordPress: Powering 43% of the internet(8:30) Outcompeting Reid Hoffman’s startup in the early days(14:03) Why open source wins over the long-term(16:21) Business models in open source(21:12) Starting Automattic in 2005, one of the first SaaS companies(28:45) Spending most of Automattic’s Seed round on servers(33:36) How to use Community + Word of Mouth for early growth(38:38) Matt’s current situation with WP Engine(43:30) How to give back in open source(53:55) Best practices from 20 years of running a remote company(59:59) Lessons on optimism from Walt Disney(1:12:33) How AI is changing coding(1:16:09) Automattic's internal employee secondary market(1:23:51) How open source increases longevity (1:26:08) Matt’s favorite classical thinkersReferenced:AutomatticWordpressMatt’s BlogBay Lights in SFInnocence ProjectVesuvius ChallengePlastic ListThe Giving PledgeDAFFYPessimist ArchiveMatt's favorite quote from Rudy FranciscoMaintenance by Stuart BrandWe are as Gods by Stuart BrandMarginal Revolution by Tyler CohenFollow MattTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Grant Lee is the Co-founder & CEO of Gamma, building instant PowerPoints, presentations, and websites with AI.As someone who’s made a lot of decks, its refreshing how Gamma thinks about slides starting with the words and narrative, using AI to build the design around the story.Gamma has put up impressive metrics, growing from zero to $50 million in ARR and 50 million users with only 30 employees. They’ve also had zero employee attrition, and a negative lifetime burn rate, with more cash in the bank than they’ve raised.We talk about building a horizontal product instead of for a specific vertical, why Grant likes hiring generalist’s, how a quarter of the team is designers, why they’ve never raised large funding rounds, and how they run the company with an efficient team while not subscribing to 996 working hours.Grant also shares how Gamma rebuilt their entire product to be AI-native in the months after ChatGPT launched, and how every department at Gamma uses AI internally.Thanks to Anamitra and Gaurav at Afore, Shiyan @ Hustle Fund, Evan @ South Park Commons, and Vas @ Accel for helping brainstorm topics for Grant.Special thanks to presenting sponsor of The Peel, Ramp.Ramp: Time is money. Save both with Ramp. Join 40,000+ companies, go to https://ramp.com/ThePeelNumeral: The end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(3:46) Gamma: The anti-Powerpoint(5:56) How to be efficient with a small team(7:58) Importance of full-stack generalists(12:15) How to hire problem solvers(15:57) Changing slides from designs to narratives(20:13) Gamma’s freemium AI business model(22:36) Ignoring conventional wisdom with a horizontal product(28:47) Why Gamma started with Slides(32:21) Raising a Pre-Seed for a horizontal product(38:25) Why Gamma avoided hyped funding rounds(40:57) How fundraising impacts recruiting(43:40) Liquidation preferences and employee equity(47:08) Gamma’s zero employee attrition(49:54) Working in-person during COVID(52:15) Using waitlists to batch new user cohorts(56:08) Re-building the product to be AI-native(58:17) How to improve your onboarding(1:00:46) Benefitting from AI models getting better(1:05:10) Growing from 60k to 50 million users(1:07:30) How to stand out as an AI company(1:09:23) Creating a Gamma API(1:11:37) How Gamma uses AI internally(1:15:06) Why Gamma doesn’t do 996 working hours(1:19:54) 4-month product sprints(1:22:16) Parenting hacks: sleep, exercise, nutrition(1:24:26) Brand and community lessons from Nike and AppleReferencedGammaCareers at GammaOptimizelyNotebookLMFin / Intercom: Afore CapitalFollow GrantTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter here to get every episode + the transcript in your inbox every week.

Ryan Sachtjen is the Co-founder and CEO of Threeflow, building software for employee benefits brokers and insurance carriers.We start with a deep dive into the nearly $2 trillion dollar employee benefits market, including the structural issues that actually give the smallest companies the most leverage.We also talk about insurance more broadly, AI opportunities in insurance, lessons from kickstarting a marketplace doing nearly $3B in volume, when his wife got cancer two months after closing Threeflow's seed round, and how his co-founders adjusted to support him.Special thanks to Bolt for supporting this episode! Join the world’s largest hackathon - up to $1m in prizes. Sign-up here.Timestamps:(3:57) Threeflow: B2B benefits marketplace(5:50) How the benefits industry works(9:20) The importance of brokers in insurance(12:32) Benefits broker software stack(15:36) How to make money in employee benefits(21:11) Ways to compete in insurance(26:34) How AI is changing insurance(31:01) What its like to be an insurance broker(35:37) Starting ThreeFlow in 2016 pre-LLMs(40:13) The 128 day walk through Europe before Threeflow(44:47) When his wife was diagnosed with breast cancer(50:23) Advice for founders on surviving large personal events(52:46) Threeflow’s unorthodox Seed round(59:46) How to vet your investors(1:04:14) Why insurance brokers exist(1:05:08) How to build a marketplace on top of Vertical SaaS(1:10:53) Choosing a marketplace entry point(1:15:05) $2.5B in premium volume on Threeflow workflows(1:26:39) Importance of supply side volume in a marketplace(1:31:21) Fundraising without a formal process(1:33:03) Hiring for “just get stuff done”(1:36:22) AI opportunities in insurance(1:41:05) Building software in insurance(1:44:56) Tactics for running a distributed team(1:49:04) Creating your own playbooksReferencedTry ThreeflowCareers at ThreeflowFollow RyanLinkedIn: https://www.linkedin.com/in/ryansachtjen/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Samir Kaji is the Co-founder and CEO of Allocate.This conversation is a deep dive into the private markets, the evolution of venture capital as an asset class, and how there are now 10x more private investment firms than public companies.We also unpack why 90% of venture funds simply can’t raise capital right now, advice for anyone raising a fund today, how to stand out as an emerging manager, why secondaries have become a primary driver of liquidity in venture, and how to navigate SPVs as a GP and LP.We also talk through the AI products they built to evaluate fund managers at Allocate, and how AI is changing venture and company building.A special thanks to Bolt and Warp for supporting this episode.Bolt: Join the world’s largest hackathon - up to $1m in prizes. Sign-up here.Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here.Timestamps:(5:31) Evolution of the private markets(17:55) VC markets post-2020(21:09) Risk / return profiles of various fund sizes(24:04) Secondaries will drive future venture returns(33:17) Creative ways to return capital(36:27) “Curiosity Revenue” in AI(41:52) Allocate’s Beyond Summit(43:42) Samir's AI fund analyzer(46:15) Fintech only 1% of financial services revenue(50:13) Triple-layered SPVs(54:50) Breaking down returns in venture(58:27) How to gauge a fund manager’s access(1:00:14) Determining appropriate fund size(1:05:02) 90% of venture funds cannot raise right now(1:09:50) How to raise a fund today(1:15:37) ChatGPT roasts Banana Capital(1:19:56) Traits of the best VCs(1:22:41) Vetting grit, hustle, and obsession(1:31:12) Why using AI is table stakes(1:36:49) Value of podcastsCheck out AllocateThe Peel episode with Eric Vishria Samir’s Venture Unlocked PodcastFollow SamirTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Anamitra Banerji is the Co-founder of Afore Capital, an SF-based VC firm that specializes in investing in pre-seed stage companies.Our conversation gets into the evolution of Pre-Seed as a category, why Pre-Seed is more than option checks, what Afore looks for when backing founders before they even have a product, how to skip your Seed and go straight to a Series A, and how to run a fundraise process.We also get into Afore’s Founder in Residence program, why every VC started an accelerator, how AI is changing venture, joining Twitter as the first PM, and how Oprah helped create the legendary verified checkmark.Thanks to Gaurav Jain and Derrick Li at Afore for their help brainstorming topics for Anamitra.And special thanks to Bolt and Warp for supporting this episode.Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up.Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here.Timestamps:(4:00) Afore: Starting in 2016 to build the pre-seed category(8:11) The unstructured data Afore underwrites at pre-seed(11:21) Pre-seed is determining bronze from gold(16:03) Why pre-seed is more than option checks(20:33) The secret to raising a Series A(23:20) Running a tight fundraise process(32:05) Skipping your Seed round(34:01) How to measure obsession in a founder(39:20) Knowing when to follow-on(40:54) Figuring out what really matters in a business(42:36) Afore’s Founder in Residence program(49:44) Pros / Cons of more access to capital for founders(52:27) Two reasons YC made every VC launch an accelerator(1:01:05) Why AI is forcing VCs to invest earlier(1:06:55) Will AI commoditize software?(1:08:29) Growing up in India, starting his first company(1:10:39) Coming to the US for school, joining Overture + Yahoo(1:14:05) Joining Twitter as first PM, creating the Verified check for Oprah(1:18:55) Building Twitter’s first ad product(1:20:28) Why non-founders can’t take foundational risks(1:23:02) Starting Afore for the Pre-Seed opportunity(1:27:47) Raising Afore Fund 1(1:31:14) How to raise your first fund(1:33:33) Was Turner the best Afore intern ever?ReferencedAfore CapitalK9 CapitalAfore’s Founder in Residence Program: SpeedrunPearXNeo AcceleratorGammaDevelop HealthFollow AnamitraTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Eric Vishria is a General Partner at Benchmark Capital.Our conversation goes inside the new class of startups going zero to $100 million ARR in 12 months, the ways AI is changing company building, and how Eric and Benchmark make new investments.We get into the risk rewards of Series As today, how Benchmark competes to work with founders, and and why the best storytellers win.We also talk about parallels between the 90’s, 2000’s, and today, and how the archetype of successful founders has changed in the age of AI.Thanks to Spenser Skates, Sajith Wickramasekara, Bobby DeSimone, and Semil Shah for help brainstorming topics for Eric!Special thanks to this episode’s sponsors:Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up here. Numeral: The end-to-end platform for sales tax and compliance. Try it here.Timestamps:(5:17) What gets Eric excited about a new investment(7:48) Backing learning machines(12:34) Backing Cerebras at inception(16:20) Why the best storytellers win(21:17) How Eric works with founders(26:38) Companies going zero to $100m in 12 months(31:09) Revenue quality of AI products(32:41) Moats and business models in AI(38:41) AI margins and runway(41:14) Parallels between winners of the 90’s and today(44:54) Archetypes of the best AI founders(50:43) SaaS companies successfully pivoting to AI(53:43) LLMs are most comparable to transistors in the 1950s(56:19) Ways Eric uses AI personally(58:05) How VC has changed over the past decade(1:01:40) VC is a hustler’s business(1:03:20) Backing extraordinary companies is all that matters(1:09:36) What makes Benchmark unique(1:17:03) How Benchmark makes investment decisions(1:18:38) Skipping senior year of high school(1:20:21) Working with Ben Horowitz and Marc Andreessen ‘00-’08(1:24:42) Starting RockMelt, selling to Yahoo(1:26:28) Joining Benchmark in 2014(1:28:08) Investing in Confluent one month later(1:28:50) Lessons from Spenser at Amplitude(1:29:36) Fireworks AI’s hyper growth(1:30:49) Pricing in AI changing from tokens to outcomes(1:32:23) Ways Eric’s perception of VCs changed after becoming one(1:34:07) How to build a management team(1:38:21 )The best CEOs make new mistakes(1:39:50) Why there should be more public companies(1:44:03) “Even great companies can be overvalued”ReferencedBenchmarkCerebrasBenchlingBen Thompson + Mark Zuckerberg InterviewConfluentAmplitudeFireworks AIAndy Price at Artisinal TalentFollow EricX / TwitterLinkedInFollow TurnerX/ TwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week

Sanjit Biswas is the Co-founder and CEO of Samsara, the fleet management and safety platform.At the time of publication, Samsara is a public company worth over $26 billion, and we unpack how exactly they went from zero to run rating at over $1.5 billion in revenue in ten years.We get into using AI to impact the physical world, how Samsara uses AI internally, and how their products prevent over 200,000 deaths per year.Sanjit has built two unicorns, and he shares everything he’s learned along the way, including what most founders and investors get wrong about hardware, thinking customer-first instead of product-first, how to know when you have product market fit, mastering sales as a technical founder, and how to spend more time with your customers.We also talk about getting his high school online in the 90’s, and the research project that turned into Sanjit’s first company, Meraki, and its $1.2 billion dollar sale to Cisco in 2012.Thanks to Bolt for supporting this episode. Help them break a world record for the largest hackathon (up to $1m in prizes): https://bit.ly/ThePeelBoltHackathonTimestamps:(4:26) Samsara: Helping the world of physical operations(8:44) Preventing 200,000 deaths per year(11:19) AI opportunities in transportation(14:43) Samsara’s internal AI tools(16:58) What people get wrong when building hardware(19:04) Starting Samsara customer-first instead of product-first(22:23) Find adjacent products for your customers(26:28) How to know you have product market fit(34:52) How to spend more time with customers and build feedback loops(43:00) 70-20-10 framework for allocating capital(45:07) Importance of selling new products to existing customers(49:15) Revisiting the product roadmap based on new technology(50:38) Why Sanjit credits focus to hitting $1B revenue in nine years(53:41) Learning to love sales as a technical founder(57:06) Getting his high school online in the 90’s(1:01:46) The research project that turned into Sanjit’s first company, Meraki(1:04:01) Importance of asymmetric risk when starting a company(1:05:41) Early days of Meraki taking off(1:09:19) Surviving and doubling during the financial crisis(1:16:00) Cisco acquiring Meraki for $1.2B(1:18:15) Meraki’s post-acquisition integration(1:20:48) Differences between 1st and 2nd company(1:24:19) Almost starting an renewable energy company(1:25:52) The power of small teams(1:28:49) One-shotting Bill Gates’ biography at 10-years oldReferencedSamsara: https://samsara.com/Meraki: https://meraki.cisco.com/Arduino: https://www.arduino.cc/Raspberry Pi: https://www.raspberrypi.com/Hard Drive: Bill Gates and the Making of the Microsoft Empire: https://www.amazon.com/Hard-Drive-Making-Microsoft-Empire/dp/0887306292No Priors Podcast: https://www.youtube.com/@NoPriorsPodcastFollow SanjitLinkedIn: https://www.linkedin.com/in/sanjitbiswas/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Michael Kim is the Founder of Cendana Capital, a fund of funds that makes anchor investments in very early stage VC funds.We talk characteristics of the best investors, how Cendana does diligence on fund managers, portfolio construction best practices, Michael’s “60x rule”, and why high ownership to fund size is the main driver of returns.We also get in to how VCs are using AI, the competition between Seed and multi-stage investors, why US endowments are under siege, and how secondaries are driving most early stage venture returns today.Michael also opens up about the early days of starting Cendana, the 18 month grind raising Cendana Fund 1, the day he almost died, and ranking in the top 2% globally in Call of Duty.Special thanks to Roger Ehrenberg, Kevin Hartz, Semil Shah, Jeff Claviar, Beezer Clarkson, Jack Altman, Jeff Morris Jr, Sheel Mohnot, Nichole Wischoff, Ted Alling, and Rick Zullo for their help putting this episode together.Thanks to Bolt for supporting this episode. Help them break a world record for the largest hackathon (up to $1m in prizes): https://bit.ly/ThePeelBoltHackathonTimestamps:(4:24) The day Michael almost died(5:10) Call of Duty & video games(9:34) Hiring @ Cendana(10:31) How Cendana uses structured and unstructured data(16:51) How VCs are using AI(19:55) Why secondaries are driving most early stage venture returns(22:01) Deciding when to sell secondaries(24:28) Best performing venture funds ever(27:26) The best VCs have amazing access to the best founders(33:42) Why Cendana backs Solo GPs(35:57) How to invest over time and hype cycles(41:35) Why multi-stage firms are investing earlier(44:45) Cendana’s current thesis: High ownership % to fund size(45:51) Why Cendana started backing non-lead VCs(48:41) How Cendana does diligence on fund managers(52:22) VC NPS Scores and Ron Conway’s Silver Bullet(53:49) Good vs bad new VC firm strategies(56:36) Determining defensibility of a strategy(57:57) “Messy middle” software buyout fund(1:03:25) Portfolio construction best practice(1:08:11) Michael’s 60x Rule(1:14:28) How Seed funds compete with multi-stage funds(1:20:05) Should you collect logos writing small checks?(1:21:07) Becoming an LP for the city of SF(1:24:42) Taking 18+ months to raise Cendana Fund 1 in the GFC(1:26:48) Warehousing the first Cendana Fund 1 investments(1:29:56) How to do a first close(1:34:29) Why it’s hard to kill a VC firm(1:37:00) What happens to ZIRP tourist fund managers(1:40:22) How to raise a Fund 2 or 3 today(1:42:07) “US endowments are under siege”(1:44:55) What the best GP LP relationships look like(1:46:41) What Fund of Funds get wrong(1:50:43) The three most interesting trends in venture todayReferencedCheck out Cendana https://www.cendanacapital.com/Deep Checks https://www.deepchecks.vc/Prior episode with Eric at Bolt https://www.youtube.com/watch?v=7Q6n1vqUrF4Follow MichaelTwitter: https://x.com/MKRocksLinkedIn: https://www.linkedin.com/in/michael-kim-cendana-capital/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Mike Vichich is the Co-founder and CEO of Pursuit, which helps companies generate more revenue from the public sector.We talk about how AI is changing Helmer’s 7 Powers, how it’s impacting the government, if DOGE is actually working, building a startup in the Midwest, and how to disagree with your team.We also get into Mike’s prior company Wisely, and how they went from $11 in the bank account and unable to pay payroll for six months, to over $10 million ARR and a $187 million exit to Olo, a public company.Thanks to Jack Altman and Blake Robbins for their help brainstorming topics for Mike!Timestamps:(3:21) How AI changes Helmer’s 7 Powers(17:06) What becomes important in AI-first economy(21:02) How AI interfaces with the government(24:02) “The rules intended to save taxpayer money ironically cause taxpayer money to be wasted”(29:34) How change orders impact public sector costs(33:20) Why DOGE has not impacted US government spending yet(38:15) Three pieces of wisdom from 2nd-time founders(41:44) Starting Pursuit to make selling to the public sector as easy as the private sector(45:35) Why cities grow expenses 5x faster than tax revenue(51:42) Pros + Cons of building startups in Ann Arbor, MI(57:43) Hiring talent density in the Midwest(59:30) Starting his first company to fix consumer credit cards(1:08:50) Pivoting Wisely to restaurant loyalty(1:12:49) $11 in the bank, missing payroll for six months(1:15:21) Embarrassing demo at an Ann Arbor tech meetup(1:18:18) Why CEOs don’t always have to be right(1:20:54) How to disagree(1:25:48) Hiring at Pursuit(1:28:30) “A bad day with customers is better than the best day in the office”(1:31:33) Crashing their first customer’s PoS on Labor Day Weekend(1:35:55) Using “The Cadence” to hit $10M ARR(1:41:55) Selling Wisely to Olo for $187MReferencedCheck out Pursuit: https://www.pursuit.us/The Four Steps to the Epiphany by Steve Blank: https://www.amazon.com/Four-Steps-Epiphany-Steve-Blank/dp/0989200507Ann Arbor New Tech Meetup: https://www.meetup.com/a2newtech/How to Disagree: https://www.paulgraham.com/disagree.htmlThe Cadence by David Sacks: https://sacks.substack.com/p/the-cadence-how-to-operate-a-saas-startup-436aa8099e8Follow MikeTwitter: https://x.com/mikevichichLinkedIn: https://www.linkedin.com/in/mikevichichFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Sam Ross is the Co-founder and CEO of Numeral.This conversation is a master class on all things growth at the zero to one stage. We talk early growth lessons from Airbnb, and stories from being one of the largest, earliest Facebook advertisers.We get into working backwards from pockets of strong demand to find business ideas, how to establish early social proof around your product, why you shouldn’t hire a growth person as your first growth hire, how he raised Numeral’s Series A in four days, and why sales tax is so complicated and how they’re using AI to make it easy.Timestamps:(3:03) Why sales tax is so complicated(8:06) Running crazy Facebook ads in 2013(11:58) Why you need to be aggressive on new growth channels(16:55) How strong retention unlocks massive businesses (18:24) Using pockets of demand to find business ideas(21:34) Balancing performance vs brand marketing(25:45) How to build a brand from scratch(29:11) When cold outbound actually works(36:18) Building early social proof around your product(43:33) Don’t hire career growth people for growth roles(49:31) Lessons building a jewelry business doing $30m in revenue(58:44) How the 2018 Wayfair v South Dakota decision led to Numeral(1:05:04) Hacking an early product together with spreadsheets(1:07:32) Automating the product(1:15:26) What happens if you don’t pay sales tax(1:20:41) How Numeral uses AI and LLMs internally(1:26:41) How to compete against non-technical incumbents(1:32:57) Why they raised VC for Numeral(1:38:19) Raising a Series A in four days(1:45:43) How big can a sales tax company really be?(1:48:55) Creating a better global tax system(1:54:31) How San Francisco is losing its soulReferencedCheck out Numeral: https://www.numeralhq.com/South Dakota v Wayfair: https://en.wikipedia.org/wiki/South_Dakota_v._Wayfair,_Inc.Follow SamTwitter: https://x.com/SpamRossLinkedIn: https://www.linkedin.com/in/sambross/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Spenser Skates is the Co-founder and CEO of Amplitude.Our conversation gets into the importance of data in product design and company building, how Amplitude is thinking about AI, and the future of user responsive software.We also get into the early days of building Amplitude, when to go multi-product, how to construct your board as a startup, hiring executives at various company stages, lessons from closing three acquisitions, lessons scaling to $300 million in ARR, inside Amplitude’s 2021 IPO, and what most people get wrong about Founder Mode.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(4:45) Using data to build great products(8:31) Why data is existential to every business(13:14) How to go multi-product(15:48) Every startup becomes a distribution company(19:29) Lessons from three acquisitions(29:09) AI hasn’t changed B2B SaaS yet(31:24) Challenges of incorporating AI in B2B SaaS(33:09) Amplitude’s AI experiments(36:29) Navigating technology hype cycles as a public company(39:40) Amplitude’s opportunity in LLMs(43:08) User responsive software(46:16) Surprising things that slow your speed of execution(51:27) What people get wrong about Founder Mode(59:48) Pivoting into Amplitude after YC(1:04:42) Nine months to raise Amplitude’s first round(1:08:31) Surprises from closing the first customers(1:12:46) Two sales lessons for technical founders(1:13:44) Scaling to $300M+ ARR(1:17:14) How to choose board members(1:19:55) Inside Amplitude’s IPO(1:21:56) “Stock price is an output of the business”(1:26:36) Evolving from startup founder to public company CEO(1:31:54) How hiring execs changes as you scale(1:34:32) Why DEI is important at Amplitude(1:39:46) Relevance of gaming and startupsReferencedTry Amplitude: https://amplitude.com/Careers at Amplitude: https://amplitude.com/careersMoxie Marlinspike’s web3 article:https://moxie.org/2022/01/07/web3-first-impressions.htmlSheep Logic: https://www.epsilontheory.com/sheep-logic/Follow SpenserTwitter: https://x.com/spenserskatesLinkedIn: https://www.linkedin.com/in/spenserskatesFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Dan Lorenc is the Co-founder and CEO of Chainguard, the safe source for open source.The internet runs on free, open source software. But as its risen in popularity, its become the latest attack point targeted by hackers and nation states.This conversation with Dan gets into the history of open source software, cloud computing, Linux, the software supply chain, how AI will impact it, and what the next big cyber attack will look like.Dan is an engineer, but he also loves sales and go-to-market. We unpack how Chainguard went from zero to 150 customers and a $40m ARR in two years.Chainguard just announced a $350 million Series D led by Kleiner and IVP, and Dan unpacks the round, plus shares his secret methodology for valuing the company.A big thank you to Dan’s Co-founder Kim Lewandowski, to Clay Fisher @ Spark, Bogomil Balkansky & Andrew Reed @ Sequoia, and Tom Loverro @ IVP for their help brainstorming topics for Dan.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(3:26) A safe source for open source(4:57) The software supply chain(7:19) Can you trust open source code with contributors in Russia?(9:43) Malware attack that almost took down the entire internet(12:40) What the next big cyber attack will look like(15:12) How will AI impact the software supply chain(17:53) The history of cloud computing(21:42) Why all cloud computing runs on Linux(23:16) How Linux + Linux distros work(29:28) Automating open source security(32:43) Chainguard roadmap: Libraries and VMs(36:40) Focusing on FedRAMP(42:44) Impact of DOGE(44:06) Zero to $40m ARR in two years(45:40) Learning to love sales as a technical founder(47:24) Lessons from Frank Slootman(51:15) How to create urgency in sales(53:16) How to build a sales team(58:23) Hiring Ryan Carlson from Wiz & Okta(1:01:45) Inside Chainguard’s $350m Series D(1:07:41) Vibe coding + Dan’s software stack(1:09:51) Cutting his hair in front of the entire company(1:10:27) Wearing a different suit to each board meeting(1:12:32) Bogomil, world’s best SDRReferencedCheck out Chainguard: https://www.chainguard.dev/Jobs at Chainguard: https://www.chainguard.dev/careersPrior episode with Dan: https://www.youtube.com/watch?v=AC4cOJ9n_Z8Linux Origin Email: https://www.reddit.com/r/linux/comments/mmmlh3/linux_has_a_interested_history_this_is_one_of/The Qualified Sales Leader: https://www.amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064Julius, AI data analysis: https://julius.ai/Claude Code: https://www.anthropic.com/claude-codeWorld’s best SDR: https://x.com/BogieBalkansky/status/19132697148828143502025 Chainguard Assemble Keynote: https://www.youtube.com/watch?v=adfU9LJg3I0Follow DanTwitter: https://x.com/lorenc_danLinkedIn: https://www.linkedin.com/in/danlorenc/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management.I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some of the harder moments of the past six years.We hit on three main themes: authentication; lessons raising multiple hard Seed extensions in the early days, including a recap before the A, and the demo that got a16z to invest; and things AI and MCP.We also talk founding a company with his brother, building a compound startup, why components are the new APIs, and what he learned about audacious goals from John Collison @ StripeA big thank you to Reid Christian @ CRV, Paul Klein @ Browserbase, and Joseph Nelson @ Roboflow for helping brainstorm topics for Colin.Timestamps:(3:39) The best developer tool for authentication and user management(5:45) The easiest way to set up billing(7:13) Building a compound startup(9:15) Lesson on audacious goals from John Collison(12:40) Developer tools are now trusted category experts(13:47) How auth impacts billing, CRM, marketing, analytics(19:44) Why auth is always changing(25:40) Coming up with the idea for Clerk(29:24) What its like starting a company with your brother(30:58) Living in a basement during Clerks early days(35:33) Getting early users narrowing focus in South Park Commons(40:10) Fundraising lessons from struggling to raise(43:46) The trick that raised Clerk’s first round from S28(45:09) Launching + the first Seed extension(50:15) Sequoia’s feedback that improved conversion rates(52:22) Why a16z led Clerk’s 2nd Seed extension(58:11) How to do a recap before Series A(1:03:34) Changing Clerk’s pitch to scare investors(1:08:56) Fundraising advice “Why partner alignment is all that matters”(1:11:42) Fast Series A and breaking 7%/week growth(1:16:32) Negotiating Clerk’s Series B at the bar(1:22:15) Investors in the arena vs in their mansions(1:27:57) The three ways AI is changing authentication(1:31:21) Why AI agents all try to steal free AI credits(1:33:09) Remember to have fun(1:36:24) Building a better product to compete in a crowded marketReferencedTry Clerk: https://clerk.com/Jobs at Clerk: https://clerk.com/careersMartin Casado’s tweet https://x.com/martin_casado/status/1558134697753841664Try Inngest: https://www.inngest.com/Follow ColinTwitter: https://x.com/tweetsbycolinLinkedIn: https://www.linkedin.com/in/colin-sidoti-751a219Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Filip Kaliszan is the Founder & CEO of Verkada, the physical security company.Verkada started in 2016 by building the best camera for physical security teams, and has since evolved into a full suite of security products for buildings. Filip takes us inside Verkada’s rapid growth to almost a billion in annual revenue, over 2,000 employees, and raising capital from investors like Sequoia, Meritech, First Round, General Catalyst, and Next47.We get into how AI and LLMs are changing hardware, the power of customer therapy, how Filip iterated on early startup ideas, inside Verkada’s very difficult first funding round, how signing their first big customers changed the trajectory of the business, and how to think about adding new products over time.We also talk through Verkada’s commitment to in-person work in the summer of 2020, how you should evaluate joining a startup as an employee, Verkada’s “software zero” employee bonus policy, and building a rooftop bar for the office.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(4:20) Verkada, the physical security technology company + Demo!(11:02) Building software powered hardware(12:56) LLM opportunities in cameras(15:49) Filip’s lifelong fascination with photography(17:57) Taking one year to come up with the idea for Verkada(22:27) Building his own home security system to learn the $16B market(27:14) Why hardware experimentation is cheaper and easier than you’d think(30:36) The importance of customer therapy(32:37) How to get your first customers, importance of quick time to demo(35:06) Why early fundraising was so hard(40:38) Verkada’s first big customer(42:23) How to decide what startup to join(45:45) The opportunity in “smart building tech”(50:34) How to launch new product lines(58:07) Re-architecting the security industry to be software-native(1:02:31) How hiring and managing a team changes as you scale(1:08:55) Why each team at Verkada has its own recruiters(1:14:00) Adding senior leaders to the team as you scale(1:17:06) Evolving from introverted engineer to CEO of multi-thousand person company(1:21:59) Verkada’s cool office and focus on in-person work during COVID(1:28:12) Building a rooftop bar on the office(1:32:20) Verkada’s Software Zero employee bonus program with 40x ROI(1:36:00) How Filip thinks about IPO vs staying privateReferencedVerkada: https://www.verkada.com/Open roles at Verkada: https://www.verkada.com/careers/Follow FilipLinkedIn: https://www.linkedin.com/in/kaliszan/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Ofek Lavian is the Co-founder and CEO of Forage, the mission driven payments company.This is a special episode, because I’m an investor in Forage, and Ofek shares everything he’s learned building the company. We go deep on food stamps, also known as EBT or SNAP, the government program that provides over $200 billion dollars per year in benefits that help 42 million low income Americans buy food.Our conversation gets into lessons from Ofek’s time leading payments teams at Uber and Instacart, building Instacart’s EBT program up to 40 employees and 10% of its total revenue, and why Ofek is so passionate about helping low income Americans.We get into the history of food stamps, market dynamics that led to low online adoption, the days Ofek thought Forage might not make it all the way to now working with the biggest players in online grocery, like Uber and DoorDash, and the long-term opportunity Forage has to build the rails the government uses to distribute trillions of dollars of restricted consumer benefits.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(4:53) Forage: Helping 42m Americans buy food(5:24) History of food stamps & EBT(9:26) Growing up as an immigrant family with low food access(11:39) 90% of EBT recipients are elderly, disabled, or working parents(12:39) How Forage sells revenue to its customers(14:15) Building Instacart’s EBT program during COVID(18:25) Why no one built an EBT payments product(22:13) Joining Forage as a Co-founder(25:01) Why government payments are so hard(30:25) Growing 15x in six months(33:52) Underdiscussed mental health challenges of startups(37:06) How the political environment impacts EBT(43:20) Why Forage charges more than competitors(45:58) Seasonality in EBT spend(46:59) Why early investors passed on Forage(48:10) The trillion dollar opportunity in restricted payments(50:56) “ There's no single idea that has destroyed more business value on planet Earth than the idea that micromanagement is bad.”(54:45) Why Forage doesn’t care about job titles(58:51) Lessons backpacking across 28 countries after college(1:02:09) How to travel on a budget(1:04:24) Importance of health(1:06:15) Saving a friends life on Mount EverestReferencedForage: https://www.joinforage.com/Ofek’s viral tweet: https://x.com/OfekLavian/status/1766950034581700697Follow OfekTwitter: https://x.com/OfekLavianLinkedIn: https://www.linkedin.com/in/ofeklavian/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Ed Lando is the Co-founder of Pareto, where he’s been an early investor in over 25 unicorns, started and incubated over 10 companies, and was recently named the most active angel investor in the world according to Crunchbase.We get into how Ed first got started angel investing, how he built up deal flow, why he’s historically kept a low profile, and why he hasn’t raised outside capital.We also talk concentration vs diversification, why there’s many ways to build successful companies, advice on hiring your first employees, and his playbook for incubating companies at Pareto, which is where he focuses most of his time. Timestamps:(0:00) Intro(2:51) Getting into angel investing(3:58) Debating high vs low PR strategies(8:27) How to start building deal flow when angel investing(10:00) Pareto: first investor in people leaving school or their job(12:05) Evolving from angel to fund(14:57) Why Ed didn’t raise outside capital(20:33) Concentration vs diversification(28:29) Investing in non-sexy categories(32:50) There’s no one right way to build a company(36:03) When to go against traditional wisdom(39:36) Lessons from his anti-portfolio(45:59) Ed’s close relationship with his parents((49:04) How we’re using AI(54:04) Incubating companies(58:38) Investing beyond spreadsheets and DCF models(1:05:49) How to trust your intuition investing (1:09:47) How to move fast(1:14:24) What most people get wrong when incubating companies(1:18:40) How to hire your first employees(1:26:27) Navigating hype when building and investing1:29:59 Venture math and the Power Law1:35:33 How Ed and Pareto’s strategy might break1:38:45 Differences between the US and EuropeReferencedPareto: https://pareto20.com/Misfit Market: https://www.misfitsmarket.com/Catalina Crunch: https://catalinacrunch.com/Zamp: https://zamp.com/Magnus Carlsen on Joe Rogan: https://www.youtube.com/watch?v=ybuJ_nIXwGEFollow EdTwitter: https://x.com/edwardlandoLinkedIn: https://www.linkedin.com/in/edwardlando/Substack: https://edwardlando.substack.com/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Tommy Nicholas is the Co-founder and CEO of Alloy, the identity and fraud prevention platform trusted by over 700 financial service companies.Our conversation explores the early days of fintech, why more consumer financial protections actually lead to more fraud, and gets into the weeds of various tactics he’s learned building a technical platform company like Alloy.We talk about embracing that the hard parts of company building are actually the best parts, why you’re most likely to give up when things first start getting better, using hands-on sales implementations in the early days to gave Alloy product market fit on steroids, how hiring changes as you scale, getting 100’s of no’s over 20 months raising their Seed round, and why TAM doesn’t matter.Thanks to Charley Ma for his help brainstorming topics for Tommy!Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try them here: https://bit.ly/NumeralThePeelTimestamps:(3:56) The platform to manage fraud(5:48) What fintech risk was like in the early 2010’s(14:34) Why company building never gets easier(19:30) Reasons the hard stuff is actually the good stuff(24:00) You’re most likely to give up when things start getting better(33:47) Doing hands-on sales implementation to get PMF on steroids(42:26) Deciding when PLG or hands-on sales will work best(52:33) Why more consumer financial protections leads to more fraud(58:14) 20 months to raise $2m vs $200m from a spreadsheet(1:06:32) “Make yourself look like a good investment”(1:10:14) Why TAM doesn’t matter(1:14:35) How to hire collaborative problem solvers(1:24:38) Why Alloy didn’t do much marketing early onReferencedTry Alloy: https://www.alloy.com/Charley Ma’s Pod Episode: https://youtu.be/5cxgB1_q2lwTry Artie: https://www.artie.com/Follow TommyTwitter: https://x.com/tommyrvaLinkedIn: https://www.linkedin.com/in/tommynicholasFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Mike Murchison is the Co-founder and CEO of Ada, the AI-powered customer service automation platform.Ada’s product and scale puts Mike at the forefront at how AI is changing software and labor markets, and this conversation felt like both a glimpse into the future, and a look into the past, at a story of pure grit and determination, working seven customer service jobs at once.We talk about why management capabilities becomes even more important in AI-native companies, how customer service is changing from a cost center to a revenue driver, and how to talk to customers more as you scale.We also get into why AI is still underhyped, what truly AI native software looks like, the realities of selling enterprise AI software today, and advice for anyone building an AI agent from scratch.Thanks to Boris Wertz and Fahd Ananta for their help brainstorming topics for Mike!Timestamps:(00:00) Intro(03:49) Making customer service extraordinary for everyone(05:44) Management becomes more important in AI-first companies(12:13) From customer inquiry to solution in production, fully autonomously(16:01) Why companies talk to customers less as they grow(20:36) Creating new products from customer service data(22:45) Broken incentives in customer service(26:10) Working 7 customer service agent jobs at once for a year(37:19) Why pivoting to Ada felt like failure(46:11) How Mike would build an AI agent from scratch today(49:15) Ways AI will change how we build and manage companies(56:44) Why the best managers are great users of AI(1:00:27) How the top 1% of people are using LLMs(1:06:22) Realities of selling enterprise AI software today(1:11:02) Building a sales team from scratch(1:15:21) Reflecting on Ada’s scale + doubling the last six months(1:16:41) Biggest software category of all-time ($750B)(1:19:51) Why AI is still under hyped(1:21:01) Ego is the biggest inhibitor to AI adoption(1:23:33) How AI will fuel explosion of creativity and productivity(1:25:20) Large companies will benefit the most from AI(1:27:41) Multi-modal language models and autonomous (computersReferencedTry Ada: https://www.ada.cx/Follow MikeTwitter: https://twitter.com/mimurchisonLinkedIn: https://www.linkedin.com/in/mikemurchisonFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Cam Doody is the Co-founder and General Partner of Brickyard, the venture capital firm moving founders to Chattanooga, Tennessee to lock-in with no distractions until they find product market fit.Brickyard is one of the most unique venture firms you’ll ever come across, and we get into how it how it was inspired by a 16x fund based in Chattanooga, why Cam and his co-founders started it during ZIRP, and why they hope everyone copies their model.We also get into Cam’s startup Bellhops, which he started in 2011 and has since grown into the third largest moving company in the US. We talk running a local services business, why 5-star review systems don’t work, and how U-Haul almost killed Bellhops overnight back in 2016.Thanks to Nader Khalil, Matt Harb, Austin Beveridge, and Spencer Levitt for their help brainstorming topics for Cam!Timestamps:(0:00) Intro(03:33) Chattanooga: Dirty manufacturing city to high tech(05:23) Brickyard’s precursor, the Lamp Post Group (a 16x fund)(09:46) How ZIRP screwed up early stage investing(13:49) What is Brickayrd?(21:14) Getting Brickyard off the ground in 2021(26:25) 100+ year old rug warehouse + maintenance nightmares(33:13) Cam wants everyone to copy Brickyard(36:31) Why economic development startup programs don’t work(38:59) YC teams doing Brickyard to escape the Trough of Sorrow(44:07) How Brickyard companies raise Series As(46:10) Nvidia acquiring Brev(52:18) How to deal with a co-founder breakup(55:45) Starting Bellhop to build a better moving company(1:02:27) How U-Haul almost killed them overnight(1:06:54) Marketing tactics for a local services business(1:12:05) Why 5-star review systems don’t work(1:18:16) How Cam’s view of VC’s changed after becoming one(1:20:37) Ways VC’s actually add value(1:25:05) The thesis for Bitcoin(1:39:21) Cam’s annual remote desert island vacationReferencedCheck out Brickyard: https://www.justlaybrick.com/The Trough of Sorrow: https://andrewchen.com/after-the-techcrunch-bump-life-in-the-trough-of-sorrow/Bellhops: https://www.getbellhops.com/Follow CamTwitter: https://www.twitter.com/camdoodyLinkedIn: https://www.linkedin.com/in/cam-doody-b489a124Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Eric Simons is the Co-founder and CEO of StackBlitz, best known for its breakout product Bolt, letting anyone build full stack apps from text, in the browser.Bolt launched in October of 2024, quickly growing from zero to a $20 million revenue run rate in two months, making it one of the fastest growing products ever. But Eric will be the first to tell you it wasn’t an overnight success - the product didn’t even work the first time they tried building it.We go behind the scenes of the seven year journey building the tech that eventually led to Bolt, how to avoid distractions, being capital efficient, living in a frat house for $100/month, and squatting in AOL’s headquarters for $1/day when he was 19.Eric also takes us inside the weeks after Bolt’s viral launch, figuring out a new business model on the fly, his strategy for fundraising and PR, why you should open source your code, Bolt’s playbook for building a community around the product that enabled their viral launch, and how AI is changing software forever.Timestamps:(0:00) Intro(2:24) Building full stack apps from text, in your browser(4:19) Running an operating system in the browser(11:48) Why Bolt failed the first time, almost shutting down the company last summer(20:18) How Bolt went viral from one tweet(28:33) Differences between ChatGPT, Claude, Cursor(39:38) Why AI code gen changes the software world order(42:01) What happened inside Bolt going from zero to $20m ARR in two months(47:32) Not sharing fundraises publicly + his PR strategy(58:57) Why the team never gave up for seven years(1:01:07) Living in a frat house for $100/month(1:04:07) How to be capital efficient(1:09:00) Living on $1/day in AOL’s HQ when he was 19(1:14:01) Inside Bolt’s Series B(1:21:03) Bolt’s hiring and product roadmap(1:32:58) Creating a new inference-based AI business model(1:38:07) Eric's playbook for building a community of users(1:44:05) Why you should open source your codeReferencedTry Bolt: https://bolt.new/Bolt on X: https://x.com/boltdotnewCheck out Webcontainers: https://webcontainers.io/$0 to $4m ARR case study with Anthropic: https://www.anthropic.com/customers/stackblitzBolt’s open source code: https://www.bolt.diy/Bolt / StackBlitz is hiring! https://stackblitz.com/careersEric’s favorite cafe, The Lighthouse SF: https://thelighthousessf.com/Lady Gaga’s “one person” montage: https://www.youtube.com/watch?v=iRxsX_30tjsLiving inside AOL HQ at 19 years old: https://www.cnet.com/tech/tech-industry/meet-the-tireless-entrepreneur-who-squatted-at-aol/Bloomberg coverage of StackBlitz Series B: https://www.bloomberg.com/news/articles/2025-01-21/ai-speech-to-code-startup-stackblitz-is-in-talks-for-a-700-million-valuation?embedded-checkout=trueJoel Spolsky’s blog: https://www.joelonsoftware.com/Follow EricTwitter: https://x.com/ericsimons40LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Rick Zullo is the Founder of Equal Ventures. Our conversation gets into Equal’s unique approach to venture capital, thinking more like public market and private equity investors, and why they also think traction is overrated at Seed.We talk through Equal’s thesis-driven model, employing a team of product owners, only investing in only 3 to 5 themes at once, and Rick’s admiration of Charlie Munger.We also talk AI - who will benefit the most, what he does and doesn’t like in terms of investing in the space, why venture capital is not really venture capital anymore, and why it sucks to be a Seed investor right now.Rick also runs the Emerging Manager Circle, a group for emerging fund managers. We get into the origin story of the group, his own struggles raising his first fund, and why talent is leaving the mega funds.Timestamps:(00:00) Intro(03:38) Why venture capital isn’t venture capital anymore(11:33) How founders should approach raising a Seed round(14:13) The realities of downrounds(15:55) Rick’s favorite founders that raised little capital(18:54) Biggest fundraising mistake founders make(21:21) Why we need to stop funding AI companies(28:34) How AI will benefit private equity the most(33:30) Three levels of opportunity in AI right now(38:36) Why traction is overrated at Seed(41:38) Investing in businesses with compounding returns on capital(52:07) VC lessons from PE firms(56:24) Why Seed investing sucks right now(1:04:15) The beauty of small exits(1:12:52) How failing to start a fund in college led to Equal Ventures(1:20:06) The struggle raising Equal’s $55m Fund 1(1:23:23) Why the best talent is leaving mega VC firms(1:30:16) The Emerging Managers CircleReferenced* Equal Ventures: https://www.equal.vc/* EMC Summit: https://www.emcsummit.com/Follow RickTwitter: https://x.com/Rick_ZulloLinkedIn: https://www.linkedin.com/in/rickzullo/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Villi Iltchev is the founder of Category Ventures, where he invests early in enterprise software startups. And he’s done it longer than almost anyone, building Salesforce’s corporate venture arm and investing early in companies like Airtable, Zapier, GitLab, Remote, Hubspot, Gusto, and Box. Fresh off raising his $160m Fund 1, we get into the opportunity he saw to start Category, and how San Francisco and Silicon Valley have changed over the past 30 years. He also shares his story growing up as an illegal immigrant in Greece, moving to the US by himself in high school, the biggest mistake of his career, advice for founders selling their company, why unit economics and profitability always matters, how developer tools went from terrible to amazing businesses, the mistake that almost killed GitLab after he invested, and why you should raise your seed round from a seed fund. Timestamps: (00:00) Intro (03:22) Illegally immigrating from Bulgaria to Greece (05:14) Moving to the US by himself in high school (13:15) Moving to SF in the Dot Com Bubble (15:49) How SF changed over the last 25 years (22:27) Why HP fell from the top of Silicon Valley (25:36) Building Salesforce’s corporate VC arm (30:29) Why SaaS was so transformative (34:35) Angel investing in Airtable (39:52) The biggest mistake of his career (42:13) Why unit economics always matter (47:20) Biggest mistake when selling a tech company (49:00) Almost starting a software PE firm and landing in VC (55:45) Lessons from August Capital + Evolution of venture (59:22) Early days of dev tools + Investing in GitLab (1:09:50) Why being contrarian is dumb (1:11:45) How GitLab almost died and emerged stronger (1:16:48) Villi’s journey to starting Category (1:25:22) Category’s thesis (1:30:48) Why startups always come in batches (1:31:57) The importance of track record in venture (1:35:32) Deciding a $160m fund size (1:39:26) Why you should raise seed rounds from seed firms (1:43:40) What Villi looks for in a startup Referenced Category VC: https://www.categoryvc.com/ Category’s $160m Fund 1: https://www.forbes.com/sites/alexkonrad/2024/12/17/villi-iltchev-raises-160-million-debut-fund-category/ Aaron Levie (Box) on The Peel: https://youtu.be/cLn_tqPvNf4 GitLab’s Recovery Stream: https://www.youtube.com/watch?v=v0TRHLvYGE0 Guy Podjarny (Snyk) on The Peel: https://youtu.be/BzKlZ_v4uCw Why SaaS won’t consolidate: https://medium.com/@villispeaks/why-saas-consolidation-is-not-happening-2b9b722e0250 Follow Villi Twitter: https://x.com/villi LinkedIn: https://www.linkedin.com/in/villi04/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Rahul Sidhu is the co-founder of SPIDRTech and Aerodome, two companies in the public safety space. He’s sold both of them, and our conversation unpacks all the lessons he learned, what he did differently with his second company Aerodome, and why he sold only 17 months after starting it. If you tuned into last week’s episode, Paul told us to never talk to the cops. Rahul gives us the other side of the story, sharing his playbook for selling to police, the government, how he met Nikita Bier in high school, and why he’s still bullish on drones, robotics, and AI in the physical world. Timestamps:(00:00) Intro(04:07) What its like testifying to Congress(08:06) Why 90% of what he knew about police was wrong(13:15) How to sell to police departments(15:24) His first business selling WoW accounts(19:00) Meeting Nikita Bier in high school(21:29) Starting SPIDRTech to improve police + community relationships(27:45) Two biggest mistakes building SPIDR(31:47) How startups break down when scaling(34:19) Selling SPIDR instead of raising a Series B(40:12) Why Aerodome was so much easier to start(42:55) Why Rahul loves unsexy markets with founder market fit(46:03) Starting Aerodome, drones as first responders(53:39) Building a capital efficient hardware startup(56:46) How regulatory changes made an opening for Aerodome(01:00:13) Inside Aerodome’s Series A(01:03:57) Selling Aerodome to Flock Safety within 17 months(01:09:31) Saying “would I work for this team?” when getting acquired(01:14:35) Seeing a homeless guy in an Aerodome shirt(01:17:02) The massive Robotics + AI opportunity this decade(01:21:42) What’s really happening with drones in New Jersey Referenced:SPIDRTech: https://www.spidrtech.com Aerodome: https://www.aerodome.com/ Nikita Bier’s Ted Talk: https://www.youtube.com/watch?v=k9QTVII_lkg  Follow Rahul:Twitter: https://x.com/rahoolsidoo LinkedIn: https://www.linkedin.com/in/rahulsidhu/  Follow Turner:Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak  Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Paul Klein is the Founder and CEO of Browserbase, building infrastructure for AI browsers.Our conversation gets into the future of software and AI agents, why authentication is a huge problem in AI, how the best infrastructure companies become product companies, and the memo he wrote that convinced him to start Browserbase despite not wanting to build another company.A year ago, Paul was a relatively unknown commodity, and definitely did not want to raise venture capital again. He shares the playbook he used to go from zero to raising $27 million in nine months “as a non-famous person” (his words).He shares all his lessons learned in the arena as he’s processing them, like what he thinks will unlock better AI agents, why you should like your own tweets, and how Browserbase competes with incumbents.Timestamps:(00:00) Intro(02:39) How LLMs unlock automation online(08:34) The future of software (AI agents)(11:21) Why AI agents need better authentication(12:59) Lessons from Twilio on building an infrastructure company(17:27) Learnings from his first startup(19:56) Bubbles, and how they drive innovation(20:37) Reasons this moment in AI is special(29:58) Why technical founders love post-PMF(31:55) The memo that started Browserbase(34:09) Why a startup should be a means of last resort(36:53) Being a solo founder(42:24) Importance of in-person culture(45:56) The best place to find engineers(48:34) How Paul hired a contractor army to build Browserbase(50:16) Why you can’t hire mercenaries(54:28) The power of emojis in marketing(57:39) Browserbase's early growth playbook (3 videos)(01:04:00) Benefits of sharing an office with other startups(01:06:00) Sales lessons from his parents(01:08:07) Why startups are like video games(01:13:43) Successful founders work the hardest and are shameless(01:18:44) Customer support is a startups greatest differentiator(01:22:06) Paul’s playbook that raised $27m in nine months as a non-famous person(01:29:03) How investors make decisions(01:33:10) Risks help startups avoid competition(01:36:37) Great infrastructure needs its own frameworks(01:39:05) Long-term thinking in LLMs will enable mass AI agents(01:42:21) Avoiding tech debt with AI moving so fast(01:43:48) Infrastructure companies need to become product companies(01:46:54) The Sine Wave philosophy to startupsReferenced:Browserbase: https://www.browserbase.com/ An Internet Browser for AI: https://memos.hawkhill.ventures/p/an-internet-browser-for-ai Rise of the Product Engineer: https://memos.hawkhill.ventures/p/rise-of-the-product-engineer Death to the Backend: https://memos.hawkhill.ventures/p/death-to-the-backend The three Browserbase marketing videosPre-Seed: https://x.com/pk_iv/status/1775183751800377344 Seed: https://x.com/pk_iv/status/1798731220005883935 Series A: https://x.com/pk_iv/status/1851270308701106383Follow Paul:Twitter: https://x.com/pk_iv LinkedIn: https://www.linkedin.com/in/paulkleiniv/Follow Turner:Twitter: https://x.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

You’re probably familiar with Baiju Bhatt’s work as the co-founder of Robinhood. But he’s also obsessed with space, and recently started Aetherflux, a space solar power company.We get into the physics of using lasers to beam solar power to the Earth, Aetherflux’s early roadmap, and how he went from zero to one going from building software to physical products.We also talk through the early days of Robinhood, getting turned down by hundreds of early investors, the accidental launch, how to know if you really have product market fit, how Aaron Levie at Box helped get Robinhood.com, the value of creativity and design, Baiju’s philosophies on combining qualitative and quantitative user research, and his favorite animal and classic car. He also tried to cut my hair.Timestamps:(00:00) Intro(02:31) Aetherflux: a space solar energy company(02:50) Origins of space solar power in the 40's & 70's(10:31) Safely beaming energy from space to Earth with lasers(13:46) Building floating space solar farms(21:27) Aetherflux's early roadmap(27:08) Growing up with dad as a Physics professor(32:18) Going zero to one building physical products(35:15) Baiju's favorite car, attempting a haircut, contemplating mustaches(38:27) Trying to prove Einstein wrong(41:42) Meeting Robinhood Co-founder Vlad at Stanford(44:10) Starting an algorithmic trading company(46:41) The beginnings of Robinhood(52:04) Getting turned down by hundreds of early investors(56:49) How they convinced Tim Draper to invest(59:39) Getting Robinhood.com because of Aaron Levie(01:01:28) Accidentally launching on a Friday afternoon(01:03:09) How to know if you have Product Market Fit(01:06:35) Combining qualitative and quantitative user research(01:14:23) Loving cats despite being allergicReferenced: Robinhood: https://www.robinhood.comAetherflux: https://www.aetherflux.com/TechCrunch coverage: https://techcrunch.com/2024/10/09/billionaire-robinhood-co-founder-launches-aetherflux-a-space-based-solar-power-startup/Seinfeld mustache scene: https://www.youtube.com/watch?v=DzZsLaLChRgThe Michelson–Morley experiment: https://en.wikipedia.org/wiki/Michelson%E2%80%93Morley_experimentEpisode with Aaron Levie @ Box: https://www.youtube.com/watch?v=cLn_tqPvNf4Follow Baiju:X/Twitter: https://x.com/BaijuBhatt LinkedIn: https://www.linkedin.com/in/bprafulkumar Follow Turner:X/Twitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Sheel Mohnot is the Co-founder of Better Tomorrow Ventures, an early stage fintech focused fund leading rounds in pre-seed and seed-stage companies.Our conversation weaves through Sheel’s two decades of building and investing in fintech, starting BTV, and why they started a fintech-focused accelerator, The Mint.Fun facts on Sheel, he was a contestant on the Zoom Bachelor during COVID lockdowns, in a Justin Bieber music video, got married in the Taco Bell Metaverse, and was once banned from Uber.We talk lessons competing against Stripe before selling his first company, common fintech startup pitfalls, and the trick every VC should use when fundraising.Timestamps:(00:00) Intro(03:13) Why fintech makes disproportionate positive change(07:49) Most interesting opportunities in fintech today(09:09) The accountant shortage(12:59) Common early fintech startup pitfalls(16:09) Building Fee Fighters to cut payment processing fees(21:15) Lessons competing with Stripe(21:57) Getting acquired by Groupon and adding $600m in market cap(25:11) Biggest first-time startup mistakes(29:21) Getting $10k in Uber credit via paid Google ads(32:13) Investing in Flexport(36:19) Navigating hot vs underhyped rounds(43:39) Sheel’s domain auction company(53:18) How he started angel investing(54:57) Spotify acquiring his podcast “The Pitch”(59:55) Why accelerators succeed and fail(01:06:07) The Mint, BTV’s fintech-focused accelerator(01:09:56) Camp BTV in the Santa Cruz Mountains(01:11:41) Early days of NerdWallet(01:14:55) Raising $75m BTV Fund 1 with Jake to fill a gap in the market(01:18:36) Understanding Fund of Funds incentives(01:22:15) References in VC fundraising(01:24:02) $150m BTV Fund 2(01:27:13) Importance of following-on when leading roundsReferenced:BTV: https://www.btv.vc/ The Mint: https://www.themint.vc/ Fee Fighters: https://techcrunch.com/2011/09/23/feefighters-launches-payment-gateway-samurai/ Follow Sheel:Twitter: https://x.com/pitdesi LinkedIn: https://www.linkedin.com/in/smohnot/ Follow Turner:Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Chris Hulls is the co-founder and CEO of Life360, the social network for families. At the time of recording, its the 15th largest app in the US, with over $330 million in annual revenue, and valued at over $3 billion in the public markets.We go inside the two decade journey building Life360, competing against Sam Altman and Woz, almost getting cancelled on TikTok, and going public twice - first in Australia, then again in the US.Timestamps:(00:00) Intro(02:04) Why CEO’s are getting more authentic(04:59) Building a social network for family(08:14) Starting Life360 after Hurricane Katrina(12:23) $30k from mom and a professor(13:52) $300k grant from Google(16:13) Launching on the first Android phones(18:20) Competing against Sam Altman, Steve Wozniak(19:06) “If we trusted the data, we would’ve shut down”(24:22) Why doubters lead to less competition(25:49) Fundraising in an unsexy market(32:21) Almost getting cancelled on TikTok(41:42) Building a contextual advertising business(48:36) Acquiring Tile, launching hardware products(52:41) Defeating patent trolls(57:22) IPO’ing in Australia and the US(01:01:00) Why its hard to go public below a certain size(01:07:50) 70% drop in downloads during COVID(01:10:03) Get to know your competitors(01:15:05) Lean Startup philosophy went too far Referenced:Try Life360: https://www.life360.com/ Wheels of Zeus: https://en.wikipedia.org/wiki/Wheels_of_Zeus Chris’ TikTok journey: https://www.entrepreneur.com/leadership/how-life360s-founder-dealt-with-teens-mocking-him-on-tiktok/457879 Chris’ TikTok: https://www.tiktok.com/@life360ceo Follow Chris:Twitter: https://x.com/ChrisHulls LinkedIn: https://www.linkedin.com/in/chrishulls/ Follow Turner:Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Joseph Nelson is the Co-founder and CEO of Roboflow, making the world programmable by building computer vision tools for developers and enterprises. We talk about how computer vision creates a new paradigm to program the world, and how visual AI is the missing piece of AGI. Joseph also shares multiple live product examples, how computer vision unlocks new data sources, lessons from Stripe and Palantir, building business models in developer tools, his experience working with David Sacks, and developer marketing tactics and how Roboflow consistently gets to the front page of Hacker News.Timestamps:(00:00) Intro(03:34) Computer vision is the missing piece for AGI(05:59) Vision as a new paradigm to collect data(10:55) Live examples of computer vision(13:45) How a Magic Sudoku solver app led to Roboflow(18:13) Using computer vision for automation(24:49) Computer vision in sports(27:02) How vision unlocks new data sources(28:24) Inside developer tool business models(33:32) The "Collison Install" and hands-on customer service(36:45) When to adopt Palantir's Forward Deployed Engineers(43:44) Why AI companies need to combine PLG and enterprise sales(50:12) Advice on developer marketing(52:30) Roboflow's greatest hits on Hacker News(01:02:19) Benefits of David Sacks as AI & Crypto Czar(01:05:32) Why all new technology has bad actors(01:07:07) Why over-regulation holds back innovation(01:12:01) How to get on the front page of Hacker News(01:19:43) Multi modality, time recognition, and agentic vision(01:28:36) Image-to-image prompting(01:30:42) Growing up in Iowa(01:32:20) Making TI-84 calculator games in high school(01:36:32) Pioneer: hunger games for startups(01:40:16) Why Roboflow does weekly Ship Lists + Ship and Tell(01:42:46) Hiring former founders and "full stack people"(01:45:16) Designing a bottoms-up organization while scaling(01:50:35) Why candidates build with Roboflow in hiring process(01:55:08) Hiring someone to help with the podcastReferenced:Robowflow: https://roboflow.com/ Roboflow Universe: https://universe.roboflow.com/ Paint.wtf: https://paint.wtf/ Roboflows NeurIPS Presentations: https://blog.roboflow.com/neurips-2023-papers-highlights/ Careers at Roboflow: https://roboflow.com/careers Follow Joseph:Twitter: https://x.com/josephofiowa/ LinkedIn: https://www.linkedin.com/in/josephofiowa Follow Turner:Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Austin Rief is the Co-founder & CEO of Morning Brew, building the Wall Street Journal for the next generation. They started the company in 2017, and grew it to 6 million subscribers and $70 million in revenue in six years.We talk through the journey starting Morning Brew with Co-founder Alex Lieberman while students at the University of Michigan, and Austin's playbook for starting a new media company from scratch today. We get into the creator economy, early stage investing, ad based business models, being the first advertiser on Instagram Stories, advice for hiring, and his secret for sourcing remote talent in Sri Lanka.Timestamps:(00:00) Intro(03:42) How to start a media company from scratch today(13:01) Future of the creator economy is niche products(14:42) Opportunity in B2B media today(17:05) Reflecting on investing during ZIRP(21:30) Why its starting to feel like 2021 again(23:16) Talking VC portfolio math(27:09) Starting Morning Brew with Wall Street interview prep(33:35) Being so dumb that they never pivoted from being a newsletter(35:29) How newsletter business models works(38:32) Morning Brew’s first viral Instagram post(40:37) Acquiring subscribers for two cents on Instagram Stories(42:29) Nik Sharma’s poor mans paid ads strategy(44:32) Landing Discover as their first big sponsor(46:06) How agencies and ad buying works(49:49) Why sales roles are so hard to hire for(53:04) Importance of offsheet references(57:43) Sourcing talent in Sri Lanka with Oceans(01:04:23) Austin and Alex’s unique co-founder dynamics(01:07:16) Dental plans, rotisserie chickens, and company laptops(01:10:00) Building WSJ for the next generationReferenced:Morning Brew: ⁠https://www.morningbrew.com  ⁠  Try Oceans: ⁠https://www.oceanstalent.com/ ⁠ Kevin Espiritu episode: ⁠https://www.youtube.com/watch?v=FefGL-qPzDo⁠ Craig Fuller episode: ⁠https://www.youtube.com/watch?v=oPPqO8eBq2M⁠ Forbes article: ⁠https://www.forbes.com/sites/hayleycuccinello/2019/02/07/morning-brew/⁠ Follow Austin:Twitter: ⁠https://x.com/austin_rief⁠ LinkedIn: ⁠https://www.linkedin.com/in/austin-rief/⁠ Newsletter: ⁠https://www.theaustinbrief.com/⁠ Follow Turner:Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak⁠ Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it/⁠

Niels Hoven is the founder of Mentava, building software to accelerate kids’ education, starting with teaching two year old’s to read. We talk about how public education isn’t designed for ambitious kids, the power of hater marketing, product design from zero to one, how too much data leads to Frankenstein products, Seed stage fundraising advice, parenting hacks, why AI won’t have a big impact on education, and the future of elite higher ed. For full show notes, visit: https://highlightai.com/share/0a0869a7-c345-4974-ba2b-726bacf7a534   Timestamps:(00:00) Intro(03:49) Why schools don’t challenge overachievers(11:58) How a hater made Mentava go viral(18:14) The secret that teaches little kids to read(24:22) How people actually learn to read(27:35) 2/3 of 4th graders can’t read proficiently(29:29) The downfall of one-size fits all education(33:44) How California almost banned middle school algebra(40:41) SF’s lottery system and how it impacts low income families(42:41) How COVID changed education(47:41) Early prototypes and going all-in on Mentava(50:56) Best practices from gaming in education(55:10) Raising a party round from lots of angels(01:03:03) Designing business models in education(01:13:19) Being pro-tech + anti-screens for kids(01:18:04) Top parenting hacks(01:22:53) How data-driven product design leads to Frankenstein products(01:25:34) Why gaming’s the best industry to learn how to build product(01:27:46) The trick Niels used to find startup ideas for 20 years(01:31:03) Why AI won’t be that impactful in education(01:36:28) What happens to elite higher education over the next decade(01:43:15) Admiring Stripe Referenced:Mentava: https://www.mentava.com/ Ryan Delk podcast episode: https://open.spotify.com/show/3QqtxGHqsPnKTG4CS7NgX5  | https://youtu.be/GTfsMEOIIxQ  How Neils raised Mentava’s Seed round: https://www.mentava.com/blog/how-i-got-50-high-profile-angel-investors-to-join-our-seed-round  Mentava’s Alphabet Book: https://www.mentava.com/alphabet-sounds-book  | https://www.amazon.com/Mentavas-Alphabet-Sounds-Niels-Hoven/dp/B0DKTQ9FW4   Follow Niels:X / Twitter: https://x.com/NielsHoven  LinkedIn: https://www.linkedin.com/in/nielshoven   Follow Turner:Twitter: https://twitter.com/TurnerNovak  LinkedIn: https://www.linkedin.com/in/turnernovak   Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Nirav Tolia is the co-founder and two-time CEO of Nextdoor. He started the company in 2011, stepped down as CEO in 2018, watched the company go public in 2021, and re-joined as CEO the summer of 2024. He also founded Epinions which IPO’d in 2004, and before that was an early employee at Yahoo. We go inside the decision to re-join the company after he thought he’d never come back, and how Nextdoor’s trying to act like a startup while running a public company. He also takes us back to the very early days of Nextdoor, the deliberate product decisions that made growth hard but led to 100M+ neighbors on the platform, the lessons learned operating his first company through the Dot Com Bubble, and what it was like being a guest shark on Shark Tank. For full show notes, visit: https://highlightai.com/share/d7bcd655-9b2f-47f7-a6e3-fdf3e109c97e  Recommended Podcast:🎙️Unpack Pricing Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more.Apple: https://podcasts.apple.com/us/podcast/id1765716600 Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg  Timestamps:(00:00) Intro(02:39) Leaving Nextdoor in 2018(07:30) Coming back in 2024(10:31) The importance of family in career decisions(17:37) Why you have to listen to learn(24:47) The Founders Mentality(26:45) “Develop and Deliver”(32:03) Local, the last remaining consumer opportunity(36:58) Why being a founder is so hard(39:21) Going to the high school from Friday Night Lights(42:07) What Nirav learned at Stanford(46:22) Working at Yahoo from $500m to $100B(49:37) Starting Epinions with Naval in 1999(51:11) Operating through the Dot Com Bubble(56:34) How Bill Gurley’s challenge led to Nextdoor(58:16) Early product experimentation(01:05:19) Why early growth was so hard, and scaling to 100 million neighbors(01:10:10) The opportunity in local news(01:12:14) Being a Shark on Shark Tank Referenced:Nextdoor: https://nextdoor.com/ The Founder’s Mentality: https://www.amazon.com/Founders-Mentality-Overcome-Predictable-Crises/dp/1633691160  Follow Nirav:Twitter: https://x.com/niravtolia LinkedIn: https://www.linkedin.com/in/niravtolia  Follow Turner:Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to get new episodes + transcript in your inbox every week: https://www.thespl.it/

Nakul Mandan is the founder of Audacious Ventures. Prior to Audacious, he was a partner at Lightspeed, joining from Battery, which he joined in ‘09 in the middle of the financial crisis while living in India. This conversation explores his journey immigrating to Silicon Valley and building an early stage venture firm from the ground up. We get into why most VCs aren’t helpful with recruiting at the zero to one stage, his thesis on starting an early stage venture firm to help founders hire A+ teams, a crash course on early stage recruiting and building a sales team, and how COVID hit right after he left Lightspeed to raise Audacious Fund 1. Timestamps:(00:00) Intro(03:43) Evolution of VC platform teams(09:53) How Audacious runs in-house recruiting processes(15:16) The reason large firms can’t help with Seed stage recruiting(17:06) Immigrating from India to the US mid-financial crisis(21:59) Silicon Valley's secret weapon(25:59) The opportunity to start a recruiting-focused Seed firm(30:14) Raising Audacious $90m Fund 1 in April of 2020(36:58) The new guard of Seed firms(39:23) Why $50-75m is the minimum viable institutional fund size(41:48) How to work with the best founders(45:30) Navigating deal dynamics, term sheets, and valuations(52:24) The two hardest parts about starting your own fund(54:32) Lessons applied raising Audacious $125m Fund 2 in 2023(58:46) Evolving from a PMF-first to Founder-first investor(01:02:09) Five traits of force of nature founders(01:07:05) How to build an A+ team(01:11:46) The importance of backchanneling(01:13:54) Why everyone thinks they’re a good people reader(01:14:35) Two most common mistakes in recruiting(01:20:59) Determining urgency of a customer’s problem(01:22:55) Hiring and scaling your first sales team(01:25:55) Why marketing is the hardest role to hire for(01:31:59) What good sales people look like(01:35:43) How to move up market + how to do pilots(01:43:40) Why Nakul admires Rafael Nadal Referenced:Audacious: ⁠https://www.audacious.co/ ⁠ Nakul’s immigration journey: ⁠https://www.nakulmandan.com/blog/2024/an-immigrant-living-the-american-dream⁠ Force of nature founders: ⁠https://www.nakulmandan.com/blog/2024/traits-i-look-for-in-founders⁠ Early GTM hiring: ⁠https://www.nakulmandan.com/blog/2023/initial-gtm-hiring-for-saas-startups⁠ Follow Nakul:Twitter: ⁠https://x.com/nakul⁠ LinkedIn: ⁠https://www.linkedin.com/in/nakulmandan⁠ Follow Turner:Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak/Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it⁠

Jenny Fleiss is the Co-founder of Rent the Runway, and more recently started Roll Rider with her three kids. We get into the early insights that led to Rent the Runway, building the company with no fashion or tech background, fundraising advice, what she’s thinking about the future of AI and commerce, and the latest company she’s building with her kids, Roll Rider. For full show notes, visit: https://highlightai.com/share/9bc59c07-05ab-41aa-b37e-f35a7c92092d  Timestamps:(00:00) Intro(05:31) How social media was Rent the Runway’s first tailwind(07:21) Being early to sustainable fashion(09:21) Starting the company at HBS in 2008(12:36) Launching with no fashion or tech background(14:49) The three biggest early surprises(18:44) Using “show don’t tell” to fundraise(20:06) Why customer social proof was so important(23:04) Spending only 10% of revenue on marketing(25:12) Getting the NYT to cover their launch(29:43) Early mistakes(31:29) Re-building the product a few weeks before launch(33:11) Why building their own logistics was so important(38:59) Subscriptions, retail, and other key product decisions(45:15) How the internet makes it harder to shop(49:30) Building conversational commerce at Walmart(53:48) Lessons from starting a company with her kids(58:38) Favorite startups in AI and commerceReferenced:Rent the Runway: https://www.renttherunway.com/ NYT’s Launch Coverage: https://www.nytimes.com/2009/11/09/technology/09runway.htmlCheck out Roll Rider: https://rollrider.com/ Use code TURNER15 for 15% offFollow Jenny:Twitter: https://x.com/Jenny_RTR LinkedIn: https://www.linkedin.com/in/jennifer-fleiss-18577314Follow Turner:Twitter: https://x.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Daryna Kulya is the Co-founder of OpenPhone, the world’s best business phone This episode is a masterclass on startup marketing, chronicling the first six years of OpenPhone, how they acquired their first customers, and inside all the different channels they used to scale the business to over 100k customers, including FB Groups, Reddit, SEO, and cold outbound.We also get into why founder-led content is so important today, and why design is a crucial core competency. For full show notes, visit: https://highlightai.com/share/28b95226-9936-4ae9-882d-6c68a1b578d5  Timestamps:(00:00) Intro(02:10) OpenPhone’s new API launch(06:41) Why a better business phone is a big deal(13:18) Immigrating from Ukraine to the US and building OpenPhone(15:39) Hacking a custom business phone(25:29) How OpenPhone got its first customers from Facebook Groups(33:02) Tricks for unlocking word of mouth(39:11) Transitioning from free to paid users(43:05) How OpenPhone cracked word of mouth on Reddit(46:29) OpenPhone’s YC experience(49:01) Why the Seed round was hard to raise(53:49) Using Slack to aggregate all customer feedback across the internet(57:38) How YC helped redefine their ICP(01:01:33) Tactics for sending cold emails(01:06:24) How to get and benefit from press(01:12:18) Daryna’s “behind the scenes” approach to founder-led content(01:16:26) Using long-tail keywords to kickstart an SEO strategy in 2020(01:23:05) When to do founder-led content vs SEO(01:28:38) How your customers should pull you up-market(01:30:18) Why OpenPhone cares about design Referenced: OpenPhone: https://openphone.com/ Ahrefs: https://ahrefs.com/ Follow Daryna: Twitter: https://twitter.com/darynakulya LinkedIn: https://www.linkedin.com/in/darynakulya Follow Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Lisa Rapuano outperformed the market 15 years in a row in the 90’s and 2000’s. We go deep on how she did it, including early investments in AOL, Dell, and owning 24% of Amazon in 2002. She shares what she learned from Jeff Bezos and Michael Dell, what makes a good investor, plus her experience as a startup CFO and how it influenced how she thinks about investing. For full show notes, visit: https://highlightai.com/share/883f2cc9-9771-4331-9a42-6ae236f50344 Timestamps: (00:00) Intro (03:18) Growing up middle class while dad worked at NASA (12:31) Moving to Baltimore to work for Bill Miller (18:12) What Lisa learned from Bill (19:41) How value investing changed over the last 30 years (26:40) Investing in internet stocks in the 90’s and 00’s (29:50) Thinking a 13x win on AOL in 1996 would be the biggest of her career (37:33) Teaching Barry Diller about the internet (41:30) How Dell reinvented PC manufacturing and created a negative cash conversion cycle (46:46) How Amazon survived the Dot Com Crash (51:53) Buying 24% of Amazon in 2002 (53:15) Why companies get the investors they deserve (57:22) What Lisa learned from Jeff Bezos (1:04:31) Lessons from raising too much money (1:07:57) Running her own fund from 2006-2016 (1:13:32) Why fees in asset management are too high (1:15:20) Joining Facet out of retirement 2017 (1:20:20) What she learned about investing from operating (1:23:47) Why women are better investors than men (1:26:43) How to hire outlier candidates (1:35:06) Why no one can be the next Warren Buffett (1:39:54) When to sell your winners Follow Lisa:LinkedIn: https://www.linkedin.com/in/lisa-rapuano/ Follow Turner:Twitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Gokul Rajaram is an early stage technology investor. As a product leader, operator and board member, he’s helped build seven generational technology companies, including Alphabet, Block, Coinbase, DoorDash, Meta, Pinterest, and The Trade Desk.We talk about lessons learned from Zuck, Sergey Brin, and Jack Dorsey, when big acquisitions can go well, how to define your ICP, why you should always size markets bottoms-up, having a fast response time, how seed investing has changed since 2007, and Gokul’s hot takes on titles at a startup. Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at ⁠https://bit.ly/WorkOS-Turpentine-Network⁠. Timestamps:(00:00) Intro(02:14) Common thread of success between the founders of Google, DoorDash, Facebook, and Square(05:50) Gokul’s first job in Silicon Valley(07:46) How Serendipity led to PMing Adsense, one of Google’s biggest products(12:20) Lesson from Sergey Brin on reducing friction before a products magic moment(18:50) How Zuck used founder mode to beat Google Plus in 2011(22:51) When big acquisitions can go well(24:47) How Gokul switches from startup helper to public company board member(28:09) The evolution of Seed investing since 2007(33:27) How to have a fast response time(37:40) Lessons from Jack Dorsey always selling(39:54) How to define your ICP(42:40) Using bottoms-up to size a market(44:05) Why Director and VP titles are bad for startups Referenced:Who’s Got the Monkey? https://hbr.org/1999/11/management-time-whos-got-the-monkey   Getting Things Done: The Art of Stress-Free Productivity https://www.amazon.com/Getting-Things-Done-Stress-Free-Productivity/dp/0142000280   How to Size a Market in 30 Minutes https://blog.blingcap.com/2023/02/13/How-to-Size-a-Market/ Follow Gokul:Twitter: https://x.com/gokulr  LinkedIn: https://www.linkedin.com/in/gokulrajaram1 Follow Turner:Twitter: https://twitter.com/TurnerNovak  LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Guy Podjarny is the founder of Blaze, Snyk, and now Tessl. He’s spent decades building at the center of developers and security. His newest company Tessl is reimagining software development, helping shape a new paradigm he calls AI Native Development.We talk through his four quadrant framework for building and investing in AI, plus go into the early days of Blaze and Snyk. He shares lessons on marketing to developers, hiring when no one wanted to work for him, overcoming multiple difficult funding rounds, and lessons from multiple M&A processes.Timestamps:(00:00) Intro(02:21) The four quadrants of building and investing in AI(14:59) Why AI startups are riskier than non-AI startups(19:42) When to sell your company vs keep building(24:57) Why hiring the early team is so hard(26:32) Early marketing tricks from Guy’s first company, Blaze(29:09) Strategies for using conferences to grow your brand(33:33) Getting three days of free PR(38:04) Moving to Ottawa(42:11) Why Sales Engineer is an underrated founder stepping stone(45:49) What he learned as CTO of Akamai(48:31) Starting his third company Tessel, and why there’s no satisfaction without struggle(50:41) How Snyk got started(54:10) Creating developer-first security(59:59) Secrets for developer marketing(01:02:31) Why podcasts work so well for marketing(01:06:26) Snyk’s failed Series AReferencedTessl: https://tessl.io/Snyk: https://snyk.io/Charting Your AI Native Journey: https://www.tessl.io/blog/charting-your-ai-native-journeySecure Developer Podcast: https://snyk.io/podcasts/the-secure-developer/AI Native Dev Podcast: https://www.tessl.io/podcastWe didn’t mention it in the podcast, but Guy just announced the AI Native Dev Conference, a virtual conference on Thurs, November 21st. Join him + many others here https://ai-native-devcon.heysummit.com/Follow GuyTwitter: https://x.com/guypodLinkedIn: https://uk.linkedin.com/in/guypoFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it/

Chris Hladczuk is the Co-founder and CEO of Hanover, where he’s building 1-click migration and 1-minute time to value fund administration for the $8 trillion in private market assets. Chris takes us through his story of building an audience online at nights while working at Goldman, breaking into tech and going from an IC to Chief Revenue Officer at a Series A startup in nine months. This episode is packed with advice on sales, getting your first startup role, and everything he’s up to at Hanover. Timestamps(00:00) Intro(02:11) Why B2B SaaS is dead(07:20) Competing against companies that have “IT departments”(11:37) Going from 0 to 100k on Twitter in one year(19:06) The ASS networking framework(25:17) Interviewing at 50 startups before quitting Goldman to join Meow(28:41) Lessons going from sales IC to Chief Revenue Officer in nine months(32:47) Using SSS to send good cold emails(35:51) Learnings as a first-time manager(40:46) How to make a good first impression(47:22) Why sales and copywriting are underrated(49:17) Navigating the startup idea maze to fund admin(56:47) 1-click fund admin migration, 1-minute time to value(59:46) Turning down Hanover’s first term sheet with no backup plan(01:03:28) Using polite persistence to get customers(01:08:41) Why the best companies are cults(01:11:01) John D Rockefeller and vertical integration(01:13:26) Doing culture fit questions at the beginning of the hiring process(01:15:34) Chris’ favorite AI tools(01:17:58) How to make founder-led content ReferencedCheck out Hanover: https://www.hanover.co/Brick: https://getbrick.app/Alex Hormozi’s Sales Podcast: https://open.spotify.com/show/6YNopzKDGDwf0auIpPTIIDSweetgreen: https://www.sweetgreen.com/Chipotle: https://www.chipotle.com/Eight Sleep: https://www.eightsleep.com/Turner’s episode with Jonathan Neman at Sweetgreen: https://open.spotify.com/episode/1Emm6VOq6MCEfQlXv05q6U?si=hJMc8LhBTeeonYJGza4gxQThe Hanover Manifesto: https://www.hanover.co/manifestoClaude Sonet: https://claude.ai/Cursor: https://www.cursor.com/Hemingway Editor: https://www.hemingwayapp.comFollow ChrisTwitter: https://twitter.com/chrishladLinkedIn: https://www.linkedin.com/in/chris-hladczuk-b09204153Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it/

Charley Ma and Mahdi Raza are the Co-founders of Pathlight Ventures, and were early employees at five unicorns, Plaid, Ramp, Alloy, Robinhood, and Stytch. They share tactical advice for early stage startup employees, lessons getting Plaid and Ramp their first customers, and deciding to build Pathlight together. Timestamps(00:00) Intro(02:30) Growing up in basements(05:15) Charley’s journey to first biz hire at Plaid(15:01) Advice on being a good startup employee(19:34) Mahdi’s path to Robinhood(26:33) Deciding between joining an early or late stage startup(32:39) Why Charley joined Plaid despite VCs telling him not to(38:52) Benefits of case studies in hiring(39:58) Why every hyper growth company is a shit show(44:24) Startup comp: equity, QSBS, early exercise, vesting(49:59) Joining Ramp as the first Head of Growth(58:35) How Ramp got its first customers(01:02:06) Advice and common traps on early GTM strategies(01:05:04) Why $1M ARR does not mean you have PMF(01:06:51) Meeting when Robinhood bought, churned, then returned to Plaid(01:09:54) Deciding to build Pathlight together(01:23:06) Raising Fund 1 in 2021 and how bad timing almost killed it(01:29:55) Reasons founders work with Pathlight(01:32:04) Why most investors add no value and give bad advice(01:36:44) Founders Pathlight invests in + Artie case study(01:44:44) Competing with incumbent funds(01:53:57) Raising a $75m Fund 2 in 2023(02:02:22) Are Seed extensions good investments?(02:07:45) Discussing startup valuations(02:09:09) Mahdi’s 10-minute market outlook (as of 8/8/24) Referencedhttps://www.pathlight.vc/https://plaid.com/https://robinhood.com/us/en/https://ramp.com/https://stytch.com/https://www.alloy.com/https://www.artie.com/ Follow CharleyTwitter: https://twitter.com/charleymaLinkedIn: https://www.linkedin.com/in/charleyma Follow MahdiTwitter: https://twitter.com/mahdirazamrLinkedIn: https://www.linkedin.com/in/mahdirazany Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it/

Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at https://bit.ly/WorkOS-Turpentine-Network. He’s had six near death experiences, and we talk about how those influenced him throughout life. We also talk about some of his early businesses, including one that had the FBI at his house when he was a kid, and lessons driving the monorail at Disney. We also get into the founding story of ClickUp, bootstrapping to $10m in ARR, hiring mistakes from scaling too fast, why Zeb likes hiring users, how ClickUp shipped generative AI features so fast, its new chat product launched earlier this week, and the trend of software convergence. Timestamps:(00:00) Intro(02:11) Zeb’s first near death experience(08:19) Childhood businesses that had the FBI at his house(18:23) Lessons from driving the monorail at Disney(25:19) Mistakes scaling from 100 to 800 employees in one year(31:04) Dropping out of college after being robbed at gunpoint(33:19) How building a CraigsList competitor led to ClickUp(35:32) Three waves of ClickUp’s product evolution(39:25) How the product slowly got worse over time(44:45) Hiring the guy who built Microsoft Teams to rebuild ClickUp(48:11) Zeb’s favorite interview question(49:59) Daily 5am standups in the first year(54:28) How ClickUp got its first customers(57:16) Bootstrapping to $10m in ARR with strong retention(58:13) Zeb’s best kept secret, user surveys (and how to run them)(1:02:42) The trend of software convergence(1:08:26) Reasons Zeb likes hiring users(1:12:19) Why VCs didn’t invest, and why it led to a better business(1:19:02) Raising from Craft, Georgian, and a16z(1:21:08) Peter Thiel: “I think you’re right”(1:24:35) How ClickUp was early to AI(1:28:03) Launching chat and video calls to hit ClickUp's original vision(1:32:02) What Zeb’s excited and cautious about in AI(1:37:24) Why Zeb journals every day Referenced:ClickUp: https://www.clickup.com ClickUp’s new chat feature: https://clickup.com/features/chat Follow ZebTwitter: https://x.com/dj_curfew LinkedIn: https://www.linkedin.com/in/zebevansclickup Follow TurnerTwitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/

Bobby DeSimone is the Founder and CEO of Pomerium, the best way to authenticate, authorize, monitor, and secure user access to any application without a VPN. Bobby explains why access control is so important, how it led to the biggest corporate hack ever, how its related to the day CrowdStrike took down the global economy, and how AI will change security. Pomerium has a unique open source approach, and Bobby takes us inside the early days of building the product, how he got the first customers, lessons learning enterprise sales as a technical founder, and inside his funding rounds, including a recent Series A led by Eric Vishria at Benchmark.  Timestamps(00:00) Intro(02:02) Access Control: a sneaky large problem(07:22) How an unsecure air conditioner led to the biggest credit card breach in history(10:23) Google’s internal security software inspiring Pomerium(16:41) Making his first money online selling a WoW bot(19:24) How CrowdStrike took down the global economy in July, 2024(22:29) Deep dive on access control and security(29:39) How access controls impacted Google vs Uber’s self-driving lawsuit(30:52) Why Zero Trust security is marketing bullshit(32:09) Advice for building access control(34:39) How open source built early trust with customers(41:39) Missing a 7-figure deal because he didn’t use LinkedIn(44:52) Everything he’s learned about sales as a technical founder(50:06) Inside Pomerium’s Series A(51:41) Advice on evaluating potential investors(56:06) How AI will change security(01:01:15) Getting in trouble at the first Pomerium board meeting(01:02:15) How to hire good engineers(01:04:00) When to scale back IC work as a founder(01:06:56) Favorite new AI tools(01:11:09) Why Meta’s open sourcing its AI models(01:12:32) Life lessons from Charlie MungerReferencedCheck out Pomerium: https://www.pomerium.com/ Crowdstrike outage post-mortem: https://www.crowdstrike.com/falcon-content-update-remediation-and-guidance-hub/ Pomerium on GitHub: https://github.com/pomerium/pomeriumFollow BobbyTwitter: https://x.com/bdd_io LinkedIn: https://www.linkedin.com/in/bobby-desimone/Follow TurnerTwitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/

Tyler Denk is the Co-founder and CEO of beehiiv, the newsletter platform built for growth. We go inside beehiiv’s early days, including joining MorningBrew as the second employee, lessons scaling to 3.5 million subscribers, the $75 million sale to Business Insider, and why I didn’t invest in beehiiv despite being an early customer. Tyler takes us inside the playbook that grew to $1.5m in monthly revenue in less than three years, including how they first positioned the product in a crowded market, how beehiiv ships so fast, when a co-founder passing away less than one year into building the business, and the day GoDaddy took the entire beehiiv platform offline for 8 hours. Timestamps(00:00) Intro(01:36) Why Turner didn’t invest in beehiiv (twice)(03:04) Joining MorningBrew as the first employee(15:28) Why newsletters are so powerful(19:40) Scaling MorningBrew to 3.5 million subscribers and exiting to Business Insider(23:14) Difference between startups and big companies(26:26) Why beehiiv has two days of no meetings(27:53) The initial insight to start beehiiv(35:39) Building a programmatic newsletter ad marketplace(39:52) Dissecting beehiiv’s nearly $20m rev run rate business model(45:21) Inside beehiiv’s first funding round(46:58) Where Turner’s reference check went wrong(50:45) Litquidity and beehiiv’s initial product positioning(52:59) How beehiiv builds in public(57:41) Banning meetings two days per week(01:00:13) Why the best remote teams always beat in-person(01:06:19) The impact of a co-founder dying one year into the business(01:11:50) Raising a Series A despite operating at breakeven(01:16:14) Why Tyler writes public investor updates(01:21:04) Moving fast, and “why perfect kills all momentum”(01:26:03) When GoDaddy took beehiiv down for 8 hours(01:29:57) Why Tyler writes a newsletter(01:32:21) His Big Desk Energy Spotify playlist(01:36:08) Why you never regret firing bad hires(01:39:53) Looking up to Elon and Brian Chesky(01:41:34) Monk mode in Columbia ReferencedThe Power of Investor Updates: https://mail.bigdeskenergy.com/p/power-investor-updatesbeehiiv’s old investor updates: https://mail.bigdeskenergy.com/c/beehiiv-investor-journeyThe BDE Spotify Playlist: https://open.spotify.com/playlist/5s8443tfYUq3LLARJwGeYP Where to find TylerTwitter: https://twitter.com/denk_tweetsLinkedIn: https://www.linkedin.com/in/tyler-denkNewsletter: https://mail.bigdeskenergy.com Where to find TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it

Michelle Valentine is the Co-founder and CEO of Anrok, the sales tax platform for software companies. We talked trends in software consolidation, lessons working with Anrok’s first customers, advice on fundraising, scaling a sales team, and early tricks for founders to avoid future tax-related headaches. Timestamps (00:00) Intro (02:19) The trend of software consolidation (03:00) Why billings and payments isn’t consolidating (06:09) Early tricks for avoiding future tax headaches (08:42) Founder lessons from first being a VC (09:28) The two catalysts that led to Anrok (17:15) How software companies used to figure out sales tax (22:51) Raising Anrok’s Seed round in 48 hours (25:42) How to join a VC's scout program (28:24) Fundraising lessons from being an investor (34:24) Surprising results from the very first “easy file” product (38:30) Lessons getting the first customers from outbound (40:19) Why you should make your first two sales hires at the same time (41:50) Sales advice when scaling into enterprise customers (46:19) How your Seed round helps raise your A and B (47:24) The reason AI and LLMs are so hard to predict (50:58) Michelle’s favorite Claude use cases (53:51) Predicting market sizes, and why Figma’s seemed small (57:39) How to invest in AI right now (1:01:01) Advice on changing your opinion (1:04:10) Getting outside your comfort zone (1:05:04) Michelle’s go-to interview question (1:34:50) The most ridiculous SPACs (1:07:23) Lessons from Scott Cook, the founder of Intuit Referenced Check out Anrok: https://bit.ly/3YTb0ED Anrok’s Journal Entries Newsletter: https://bit.ly/3AxrtUV Anrok Mid-year SaaS Sales Tax Review: https://www.anrok.com/resources/mid-year-saas-sales-tax-review-2024 Michelle’s Article on AI, Part 1: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-one-michelle-valentine Part 2: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-two-michelle-valentine Part 3: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-three-michelle-valentine Superintelligence: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/1501227742 Where to find Michelle: Twitter: https://twitter.com/_vltn LinkedIn: ⁠https://www.linkedin.com/in/michellevalentinehk/ Where to find Turner: Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak/⁠ Newsletter: ⁠https://www.thespl.it/

Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at https://bit.ly/WorkOS-Turpentine-Network. Aaron Rubin is the Founder and CEO of ShipHero, a warehouse management system for brands and 3PL providers. We talk through Aaron’s journey building ShipHero, starting with what is now the largest Jiu Jitsu apparel brand in the US, which he almost went bankrupt running during the financial crisis. He shares how that business led to ShipHero, takes us inside the early days, explains why warehouse robotics and 4PL’s are overhyped, and discuss the rapid rise of TikTok Shop, Temu, and Shein. Timestamps (00:00) Intro (02:01) The USPS shipping label scam (07:10) Starting the largest Jiu-Jitsu apparel brand (09:46) Narrowly avoiding bankruptcy in 2008 (17:08) Why ecommerce is so hard (21:16) Starting ShipHero to manage their own warehouse (28:00) Powering Shopify’s early fulfillment network (30:59) How 3PL’s are still solving basic problems (34:02) Why warehouse robotics is overhyped (41:48) Where drones fit into logistics (44:55) Aaron argues why the 4PL model doesn’t work (55:40) TikTok Shop is the fastest growing US ecommerce channel ever (58:42) How Temu and Shein leverage the 321 program to avoid tariffs (1:02:49) Why Temu and Shein are slowing US ecom growth (1:04:17) Topgrading: The most boring, most valuable hiring strategy (1:11:29) Business lessons from playing poker Referenced ShipHero: https://shiphero.com/ Topgrading: https://www.amazon.com/Topgrading-Hire-Coach-Keep-Players/dp/094400234X Where to find Aaron Twitter: https://x.com/AaronandML LinkedIn: https://www.linkedin.com/in/aaronandml Where to find Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it

Logan Bartlett is a Managing Director at Redpoint. If you like startups and you listen to podcasts, you’re probably familiar with his podcast, the Logan Bartlett Show. We talk about how it first got started, plus all his tricks for growing the podcast, including his canonical episodes in 2022 that helped pop the web3 bubble. We also talk market cycles and bubbles, and what Logan’s seeing in the data today, especially in AI, plus Logan’s philosophy’s on venture capital as an asset class, his favorite under the radar investors, and advice for his younger self. Timestamps: (00:00) Intro (01:33) Not getting invited to Michael Rubin’s white party (04:29) Meeting on Twitter during COVID (11:09) How Logan and I benefited from Twitter (16:55) Early days of the Logan Bartlett Show (22:10) Why podcasts are so hard to grow, and how Logan did it (24:50) Learning YouTube’s the best for podcast growth (29:51) Inside Logan’s web3 episodes with Zach Weinberg (32:07) Lessons from studying history and market cycles (33:15) Producer Ben fact checking Logan's historical railroad statistics (39:42) How to invest in and around bubbles (51:00) Market data from Redpoint’s 2024 AGM update (55:12) Differences between companies valued at 100x and 5x ARR (1:00:04) The Barbell Theory of asset management and why Logan disagrees it will happen in VC (1:09:40) Ways VCs can actually add value (1:12:27) Redpoint’s founding story + greatest hits (1:18:14) The most underrated investors and founders (1:21:35) Advice for young people: pick a niche, go deep, stay focused If you enjoy this conversation and you’re not already, make sure to like, comment, follow, and subscribe to my newsletter in the show notes to get future episodes in your inbox every week. Referenced: Clearspace https://www.getclearspace.com/ Acquired’s TikTok episode https://www.acquired.fm/episodes/tiktok Gorilla Game https://www.amazon.com/Gorilla-Game-Picking-Winners-Technology/dp/0887309577 Redpoint’s AGM Update https://docs.google.com/presentation/d/1T3kGf-n4cmd6_UqOQNb79ZXFL723b9HdZyTnk9sLOlM/edit Where to find Logan: Twitter: ⁠⁠⁠https://x.com/loganbartlett LinkedIn: ⁠https://www.linkedin.com/in/loganbartlett/ Where to find Turner: Twitter: ⁠⁠⁠https://twitter.com/TurnerNovak⁠⁠⁠ LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/turnernovak/ Newsletter: ⁠⁠⁠https://www.thespl.it/⁠

Ryan Denehy is the founder and CEO of Electric, software that helps businesses manage their IT and IT support. We talk through his first two startups from founding to exit, the early days of getting Electric off the ground, and Ryan’s frameworks for fundraising, recruiting, and sales. Timestamps: (00:00) Intro (03:05) Building an ad network for extreme sports websites (11:07) Why a better pipeline solves all problems (13:24) Ryan’s trick for hiring executives (17:00) Selling the ad network to USA Today (18:11) Moving to SF to start a software company (21:33) Getting rid of his car to extend runway (24:23) Paying rent with credit cards (29:17) Struggling to raise a Series A (31:55) Using channel sales to grow the business (37:05) Almost running out of money before selling to Groupon (43:37) How cloud created the perfect timing to build Electric (48:33) Leveraging software and AI to automate manual human tasks (51:45) Why you should avoid buzzwords in marketing (53:57) Pros and cons of being a solo founder (56:14) Why Electric built a large initial board (01:02:41) Advice for picking lead investors (01:06:35) How VC fund dynamics have inflated Seed rounds (01:09:16) The downsides of high valuations (01:12:45) Almost wiring back the Seed round (01:16:37) Why every fundraise is a Pipeline problem (01:21:04) The reasons VCs actually pass on founders (01:26:42) Cutting the burn rate in 2022 Electric.ai: ⁠https://www.electric.ai/⁠ Where to find Ryan: Twitter: ⁠⁠⁠https://twitter.com/DenehyXXL⁠ LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/ryandenehy/ Where to find Turner: Twitter: ⁠⁠https://twitter.com/TurnerNovak⁠⁠ LinkedIn: ⁠⁠https://www.linkedin.com/in/turnernovak/⁠⁠ Newsletter: ⁠⁠https://www.thespl.it/

Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Frank Rotman is the Co-Founder and CIO of QED Investors, and before that helped start Capital One. Frank and I go deep on their founding stories, as well as one of QEDs first big winners, Nubank. Frank also gives us a crash course on fintech, lending businesses, and crypto use cases; his hot takes on the venture asset class as a whole, with lots of advice for emerging managers; plus a case study on how high valuations too early on are bad for a startup. Timestamps: (00:00) Intro (04:22) Starting Capital One in 1988 (07:04) Spinning out as an IPO (10:42) Starting QED in 2008 before Fintech was a category (20:51) Raising their first outside fund (22:03) Investing early in Nubank (25:11) Fintech opportunities in India (27:45) De-risk investing in new markets (29:55) How financial services have changed over the past 30 years (31:33) Inside a new Capital One credit card in the 90’s (36:31) How most companies launched new cards in the 90’s (39:46) The most profitable types of credit card customers (42:00) Mistakes founders make building credit businesses (48:33) Frank’s “Three Body Framework” for VC (54:48) Losing strategies in VC (01:03:39) Unpacking why high valuations are bad for startups (01:16:20) Frank’s journey in and out of crypto (01:24:23) Actual use cases for stable coins and NFTs (01:34:09) Unpacking the lending supply chain (01:41:44) The difference between Fundamentalist and Revolutionary investors Referenced: VCs Three Body Framework: https://cdn.prod.website-files.com/605db59b78445cf5ae548e49/628b9d826f9af3217c9807a2_Three-Body%20Problem_%20Finding%20the%20New%20Stable%20Points%20in%20Venture%20Capital.pdf The House Money Effect: https://x.com/fintechjunkie/status/1466217991532650496 Fundamentalist vs Revolutionary Investors: https://www.linkedin.com/posts/frank-rotman_there-has-been-and-always-will-be-two-competing-activity-7128137991654445057-NuXf/ Where to find Frank: Twitter: https://twitter.com/fintechjunkie LinkedIn: https://www.linkedin.com/in/frank-rotman/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Warp: Don’t let payroll and compliance hold your startup back: visit https://www.joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Yossi Levi shares his incredible story: transforming a small family car lot into a $28 million dollar powerhouse, founding venture-backed Gettacar and growing it to $90 million in revenue, before returning the capital to investors and growing his anonymous Twitter account into Car Dealership Guy, a B2B automotive media empire. Yossi takes us inside his early marketing strategies, the hard earned lessons from chasing product-market fit, and the playbook to building a lean, scalable B2B media machine. Timestamps: (00:00) Intro (07:26) Helping at his dad’s used car lot (11:22) How car dealerships make money (14:32) $28m revenue with Facebook ads  (17:48) Putting gifts in customer trunks and filming it (22:58) Starting Gettacar to sell cars online (25:04) When a VC pulled his first term sheet (31:08) Recruiting full-time hires with part-time consulting gigs (34:45) Personally guaranteeing the debt used to finance vehicles (36:50) Helping subprime consumers buy cars online (39:24) How 2021 tricked them into thinking they had a sustainable business (41:57) Why you can’t rush Product Market Fit (42:23) Pivoting Gettacar to a profitable, PE-backed business before winding it down (47:22) Starting an anonymous Twitter to share insights from his day-to-day (50:08) Turning Car Dealership Guy into a media business  (53:38) Doxing himself with a 13-minute documentary  (58:29) Why you have to consume to be a good creator (1:00:04) Screensharing CDGs content schedule (1:02:59) Why every employee needs to generate content or revenue (1:09:27) Creating a car / auto influencer agency (1:11:34) Building a B2B automotive ad network (1:14:50) Evolving into a holding company (1:20:27) Importance of moving fast  (1:23:34) Why people actually like sponsored content (1:28:08) Wishing he pivoted to B2B faster More on Car Dealership Guy: ⁠https://www.dealershipguy.com/ Referenced Who the F*ck is Car Dealership Guy: ⁠https://www.youtube.com/watch?v=_wTsAez_nMs⁠ Russ Flips Whips: ⁠https://russ.dealershipguy.com/⁠ Freight Waves’ Craig Fuller on The Peel: ⁠⁠https://youtu.be/oPPqO8eBq2M⁠ Epic Gardening’s Kevin Espiritu on The Peel: ⁠https://youtu.be/FefGL-qPzDo⁠  Where to find Yossi: Twitter: ⁠https://twitter.com/GuyDealership⁠ YouTube: ⁠https://www.youtube.com/@CarDealershipGuy⁠ Where to find Turner: Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak/⁠ Newsletter: ⁠https://www.thespl.it/

Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Edwin Dorsey is the author of The Bear Cave, a weekly newsletter exposing publicly traded companies that are misleading investors and harming customers. I’ve enjoyed Edwin’s writing since he launched his newsletter the Bear Cave in 2020, and he shares his best kept secret for doing customer research: FOIA requests. We also get into short selling more broadly, common corporate red flags, the economics of his media business, almost getting kicked out of Stanford for raising issues at Care.com his sophomore year, Planet Fitness’s illegal billing operation, Hershey’s Mr. Beast problem, and the creator economy more broadly. (00:00) Intro (05:11) How shorting works (07:20) How short sellers exposed Enron (10:51) Edwin’s process for finding bad companies (15:52) Root Insurance and aggressive pricing (20:14) FOIA: the best kept secret for company research (24:30) Biggest corporate red flags (28:17) Most common industries for bad actors (29:32) Why scammers target minorities and low income consumers (31:46) Edwin’s $1B to $10B market cap sweet spot (34:03) The challenges of mainstream media (38:15) Exposing Care.com as a student at Stanford (45:25) Why immediate board resignations are a red flag (49:45) Launching The Bear Cave in Feb 2020 (49:37) Using podcast appearances to grow (56:06) The newsletter's business model (1:00:00) Experimenting with side-newsletters, job boards, and consumer surveys (1:10:04) Planet Fitness: gym or illegal billing operation? (1:18:45) Herbalife the pyramid scheme (1:21:05) Hershey’s MrBeast problem (1:28:15) Marketing and social signaling in CPG products (1:30:47) AgEagle Aerial Systems: $4B market cap, zero revenue (1:34:50) The most ridiculous SPACs (1:41:06) How Edwin differentiates his research (1:47:07) Favorite short sellers (1:47:59) Companies that will lose to AI (01:49:29) Why creator-led business will steal share from incumbents Referenced The Bear Cave: https://thebearcave.substack.com/ FOIA Request Template (#13 here): https://www.readideabrunch.com/p/our-2023-hedge-fund-analyst-christmas SEC Full Text Search: https://www.sec.gov/edgar/search/ WSJ’s Care.com Story: https://www.wsj.com/articles/care-com-puts-onus-on-families-to-check-caregivers-backgroundswith-sometimes-tragic-outcomes-11552088138 Planet Fitness CEO resignation letter: https://x.com/StockJabber/status/1762220603715596460 Aurelius Value: https://x.com/AureliusValue Big River Capital: https://x.com/BigRiverCapita1 Marc Cahodes: https://x.com/AlderLaneEggs David Orr: https://x.com/orrdavid Citron Research: https://x.com/CitronResearch Where to find Edwin: Twitter: https://twitter.com/StockJabber LinkedIn: https://www.linkedin.com/in/edwin-dorsey-a9195273/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Lisa Wehden is the Founder and CEO of Plymouth Street, making fast and simple immigration for technologists. We go deep on the broken US immigration system, how its holding back US innovation, and the secret 0-1A Visa you can get in as fast as four weeks. Lisa lived in a sawmill while building her first climate tech startup, and we go inside that journey, giving the VC money she raised back to start Plymouth, raising grants to fund it, and how she broke into Silicon Valley as an outsider. Timestamps: (00:00) Intro (04:51) The state of US immigration (09:26) Why immigrants are good founders (11:43) The secret O-1A Visa (12:18) Why the O-1A is easier to get (16:54) Founders that have gotten their O-1A (20:00) Getting a Visa in four weeks with Plymouth (22:01) The 500-page, physical paper Visa application (25:57) Lisa’s US immigration COVID hobby (27:58) Living in a Sawmill building a climate tech startup (30:59) Giving VCs their money back (32:19) Joining Interact in SF (33:51) Raising grant money instead of VC (34:40) Becoming a paralegal to learn the industry (37:24) The Plymouth 100 community (39:20) How Lisa raised grant funding from Eric Schmidt and Tyler Cowen (43:55) Talent is the bottleneck to AI development (46:04) How to break into Silicon Valley as an outsider (52:43) Hiring on hopes and fears (55:31) "Write it down, make it happen" (56:45) Benefits of doing a calendar audit (1:01:54) Anyone can be an entrepreneur (1:04:53) Why Lisa doesn’t work from her phone (1:06:38) How to fix the US immigration system More on Plymouth Street: https://www.plymouthstreet.com/ Referenced: Interact: https://joininteract.com Lisa’s 0-1 Visa Guide: https://lisa-wehden.medium.com/a-guide-to-applying-for-the-o-1-visa-for-extraordinary-individuals-8ca5f22ff86b Writing a forwardable email intro: https://also.roybahat.com/introductions-and-the-forward-intro-email-14e2827716a1 Where to find Lisa: Twitter: https://twitter.com/lisawehden LinkedIn: https://www.linkedin.com/in/lisa-wehden-aa111385/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Melissa Cash is the Co-founder and CEO of Pok Pok, a montessori-inspired collection of digital toys that spark creativity and learning through open-ended play. Prior to Pok Pok, Melissa spent a decade working in marketing and design roles, helping Snowman drive 9-digits of downloads across its game portfolio and designing physical products at Disney. Timestamps: (00:00) Intro (05:46) Creating a Montessori inspired game (12:18) Why it's impossible to avoid screen time (15:35) Designing a non-addictive product (17:38) Monetizing a non-addictive game (21:47) How to price a subscription game (24:18) Using new features to drive retention (26:04) Marketing a kids game to parents (30:59) Why Pok Pok waited to launch Android (34:12) How getting pickpocketed in Germany led to a job designing products at Disney (39:23) How great products can define a childhood (43:21) Lessons from having a great idea while working at Disney (46:03) First coming up with the idea for Pok Pok (49:00) Advice for starting your first company (50:10) Fundraising tactics from Pre-Seed to Series A (54:08) How to build your network from zero (57:08) Getting the most out of Slack groups (59:07) Melissa’s hack for in-person events (01:01:33) Tactics for meeting people at events (01:03:39) Winning multiple Apple design awards (01:07:07) How to get press for your startup (01:13:17) Prioritizing getting women on Pok Pok’s cap table (01:18:38) Strategies for staying creative (01:21:58) Melissa’s influencer marketing hacks (01:24:24) Lessons from failed influencer campaigns (01:28:19) Growing 5x YoY, adding STEM content (01:30:28) What surprised her about starting a company Referenced: Try Pok Pok for 50% off an annual subscription with code POKPOK50: https://apple.co/3XAGSwT Snowman Studios: https://www.builtbysnowman.com/ Hampton Private Founder Group: https://joinhampton.com/ VC Backed Mom’s: https://www.vcbackedmoms.com/ The Peel Podcast episode with Eric Newcomer: https://www.youtube.com/watch?v=HXH_peQWtnc More on Pok Pok’s Series A: https://techcrunch.com/2024/06/18/now-a-series-a-startup-kids-app-and-digital-toy-pok-pok-is-coming-to-android/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Ed Sim is the Founder of boldstart ventures, which partners with bold founders reinventing the enterprise stack at the inception stage. Ed takes us inside the journey building boldstart, from its first $1m fund in 2010 up to $850m in AUM today. Timestamps: (00:00) Intro (03:48) Evolution of early stage investing(05:11) Inception stage investing (10:32) Backing bold founders reinventing the enterprise stack(11:20) Repeatable ways to build enterprise businesses (12:04) The 5 P’s of early stage investing (14:12) Backing Guy Podjarny and Snyk (18:18) Knowing when to follow-on (19:18) The 3 Ch's of a good board member (22:01) How Ed’s board role changes over time (24:20) Balancing founder friendly with returns (27:20) How to build customer relationships (30:24) Advice for closing customers (33:47) Creating the Seed category in 2009/10 (37:31) boldstart’s $1m Fund 1 (39:00) Why Ed didn’t join a large firm in 2012 (39:55) boldstart’s $16.5m Fund 2 (40:26) Why LPs passed on the first funds (43:11) Leading rounds in Kustomer, Snyk, BigID, and Blockdaemon in Fund 3 (47:09) Why $112m Fund 4 was the hardest to raise(50:52) Ed’s approach to LP fundraising (55:12) Inside Meta’s acquisition of Kustomer and sale back to the founders (59:52) Backing Rahul from Superhuman a 2nd time (01:00:52) The different GTM playbooks (01:02:20) Importance of contract size and time to close (01:05:07) Why AI makes security more important (01:06:11) When to switch from founder-led sales(01:07:46) Backing ProtectAI after a conference (01:08:28) Balancing between inbound and outbound sales (01:09:55) Winners and losers in AI (01:15:26) Building the boldstart team (01:25:19) Lessons being an interim CEO (01:27:15) How ZIRP pulled revenue forward (01:29:08) The death of high growth software (01:32:58) Identifying startup opportunities incumbents won’t crush (01:35:00) Second order effects of AI (01:36:46) Using "Intuitive TAM" to size new markets (01:38:04) Investing before there’s a market map (01:38:57) Balancing family, fitness, and career Referenced: https://boldstart.vc/ Turning Down HBS: https://x.com/edsim/status/1315644287007240193 Ed’s tweet on raising Fund 4: https://x.com/edsim/status/1315644287007240193 Second Order Effects of AI: https://www.whatshotit.vc/p/whats-in-enterprise-itvc-379 Death of Hyper Growth: https://x.com/edsim/status/1797613384994623808 Where to find Ed: Twitter: https://twitter.com/edsim LinkedIn: https://www.linkedin.com/in/edsim/ Newsletter: https://www.whatshotit.vc/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelNilam Ganenthiran is the founder and CEO of Beacon Software. Previously, he was the 12th employee and President at Instacart.We talk tactics for customer research, building customer relationships, balancing strategy and execution, how to serve on and manage a board, what happened when Amazon bought Instacart’s biggest customer Whole Foods, inside its COVID response, surviving eight months of runway in 2015, his new company Beacon Software, and more.Timestamps:(00:00) Intro(04:23) Inside Amazon acquiring Instacart’s biggest customer, Whole Foods(12:13) Lessons from quickly signing 8 of the top 10 grocers(13:06) Why grocers were slow to adopt ecommerce(15:29) Building “Shopify for grocers”(16:22) Sales = building relationships(19:05) Why Wegman’s is one of the best grocers in the world(20:43) Cold calling Wegman’s and signing them two years later(24:33) How to do customer research(26:59) Catching an Uber in suits on the highway(28:50) Why Instacart was possible back in 2013(30:36) Launching Instacart’s advertising network(38:46) Growing 5x in 5 weeks during COVID(45:20) How Nilam started angel investing(47:56) Advice for sitting on boards(50:00) The roles and incentives of a board member(54:03) Deciding when to keep going and when to give up(56:02) Nilam’s framework around optionality(59:17) Seven years of weekly redeye flights(1:00:30) Almost running out of money 8 months after Instacart’s Series C(1:07:54) Why time is your scarcest resource & startups are default dead(1:10:00) Nilam’s new company, Beacon Software(1:11:28) Why he’s excited about AI(1:13:25) How AI makes human relationships more important(1:14:41) Turner’s investing lessons from family membersBeacon Software: https://beaconsoftware.ca/Where to find Nilam:Twitter: https://twitter.com/nilamgLinkedIn: https://www.linkedin.com/in/nilamganenthiran/Where to find Turner:Twitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovak/Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Ankur Goyal is the Founder and CEO of Braintrust, the end to end developer platform for building the world's best AI products. Their customers include companies like Instacart, Zapier, Notion, Airtable, Replit, and more. We hit on the importance of LLM evals, advice for building AI products, why the best companies have two AI product roadmaps, and his non-conventional advice for founders. Timestamps: (00:00) Intro (04:04) Why everyone’s now an AI company (06:03) Reasons LLM evals are so important (08:10) Typescript becoming the language of AI (09:19) Replacing vibe checks with Braintrust (10:37) Making OpenAI’s protocols the standard (11:27) Why the best companies have two AI roadmaps (13:06) Building your product so each LLM release makes it better (14:54) Predicting AGI is impossible (15:54) Why people who work with LLMs aren’t worried about AI safety (16:52) The best developers are all-in on co-pilots (18:11) How AI is changing software development (21:09) Combining IDE, CIDC, and observability in one product (27:18) Are models more like CPU’s or relational databases? (30:14) How to pick an LLM (33:00) Advice for staying on top of new AI developments (34:30) Why tool calling is so important (38:02) Advice for young software engineers (40:25) Learning to code doing linear algebra homework (42:36) Lack of purpose interning in big tech (44:07) Working at MemSQL learning to be a founder (47:52) How to get a job at a startup (50:43) Building his first startups product on an international flight (52:39) Three lessons from his first failed startup (54:46) Don’t delegate what you’re good at (55:46) Why you should be careful listening to VCs advice (57:34) Tactics for successful delegation (59:36) Why Ankur doesn’t do any meetings (01:02:42) The importance of self-service in unlocking certain customer segments (01:05:14) How Braintrust got started (01:07:45) Advice on picking your target customers (01:10:35) How Braintrust hires with work trials (01:15:21) Balancing security with a modern UI (01:17:49) Why it’s hard to sell non-AI products right now (01:19:21) Advice for selling to large enterprises (01:23:10) Ankur’s favorite AI products Referenced: https://www.braintrustdata.com/ SICP Book PDF: https://web.mit.edu/6.001/6.037/sicp.pdf Hardcopy: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871 Linear’s guide to work trials: https://linear.app/blog/why-and-how-we-do-work-trials-at-linear Where to find Ankur: Twitter: https://twitter.com/ankrgyl LinkedIn: https://www.linkedin.com/in/ankrgyl/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelAlan Feld is the Founder and Managing Partner of Vintage Investment Partners. Vintage is one of the largest fund of funds in the world, managing over $4 billion across what is mostly investments into other venture funds, plus some secondary and direct startup investments at the growth stage. Timestamps: 00:00 Intro 03:53 What is Vintage 05:40 Why VCs adding value can waste a founder’s time 09:01 VC, where the asset chooses the investor 10:14 Fund size is the enemy of returns in VC 14:57 What people get wrong about FoFs 16:01 The value FoFs bring to LPs 17:11 Why entrepreneurs drive VC returns 17:55 Vintage’s unique FoF model 19:05 Does replacing the founders with an outside CEO work? 21:39 Starting Vintage after the Dot Com Crash in 2002 23:41 Buying secondaries at 70-80% discounts 25:13 Biggest mistakes when buying secondaries 26:18 Research around what makes the best entrepreneurs 31:09 Lessons from six downturns 34:41 Comparisons between 2002 and 2022 37:07 Advice for raising your first VC fund 41:16 The importance of differentiation 45:57 Sustainable ways to differentiate 49:05 What Vintage looks for in new fund investments 49:57 Advice for scaling a VC firm 53:47 Succession planning 57:50 What Alan’s doing post-Vintage Vintage Investment Partners: https://www.vintage-ip.com/ Where to find Alan: Twitter: https://twitter.com/alanf_feld LinkedIn: https://www.linkedin.com/in/alan-feld-1744389/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Anu Sharma is the Co-founder and CEO of Millie, building a better care system from the inside out. Our conversation covers the existing maternal health system, how Millie is reinventing it, and how to succeed building a healthcare company. Timestamps: (00:00) Intro (03:16) Problems in US maternity care (13:21) Why insurance reimbursement drives healthcare (16:11) How bundled care unlocks personalization (18:48) From fiction writer to 20 years in healthcare (24:22) Why consumers don’t act like consumers in healthcare (26:09) The reason scale matters (27:43) Bundled payments and new care design (32:16) What make Millie unique (35:58) Importance of picking regional markets in healthcare (37:08) The two paths for insurance reimbursement (41:08) Why distribution is the product in healthcare (44:25) Opportunities in cash pay care (48:28) How Anu fundraised without a product (51:06) The future of in-person, hybrid, and virtual healthcare (52:56) Building maternity clinics for $150k Check out Millie: https://www.millieclinic.com/ Where to find Anu: Twitter: https://twitter.com/anu_anusharma1 LinkedIn: https://www.linkedin.com/in/anu-sharma-b169b12 Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Aaron Levie is a co-founder and the CEO of Box. This conversation covers opportunities in AI, the early days of Box, and lessons Aaron's learned on his founder journey. Timestamps (00:00) Intro (03:11) Why ChatGPT was an iPhone moment (04:37) Advice for large companies incorporating AI (11:16) Why AI will add jobs, not steal them (16:13) How AI is supercharging Box’s products (19:03) AI agents: the $1 trillion opportunity (25:27)Estimating size of new markets(29:58) Starting Box with high school friends (33:18) Living out of their first office (34:52) Why early investors passed on Box (37:24) Pivoting from consumer to B2B (39:53) How Box got its first customers (41:57) Should founders talk to Associates at VC firms? (43:26) How Mamoon at Kleiner saved Box at its Series B (46:25) Turning down an acquisition before IPO (50:51) Why Box’s IPO was so hard (54:11) Fending off an activist investor during COVID Check out Box: https://www.box.com/ Where to find Aaron: Twitter: https://twitter.com/levie LinkedIn: https://www.linkedin.com/in/boxaaron/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Elad Gil is the founder of Color Genomics and Mixer Labs, which he sold to Twitter, and an early investor in iconic companies like Airbnb and Stripe, plus upstarts like Perplexity and Anduril. This is a wide ranging conversation that covers education, AI, and advice for building a startup. Timestamps (00:00) Intro (03:46) Building cool monuments (09:12) Fixing education (16:38) Why AI is underhyped (19:02) Four trends to watch in AI (19:55) Why there aren’t large biotech companies (23:21) The current state of Elad Gill (24:32) How he incubates companies (26:32) Contemplating AI-driven buyouts (27:29) His investing strategy, from early to late stage (36:57) Why he remained solo for so long (40:19) How to get conviction in unpopular investments (42:53) What made Steve Jobs a good communicator (44:00) The importance of ambition and leadership (46:28) Why Elad puts so much weight in the market (47:45) The evolution of Google’s business model (49:17) How to monetize consumer products (50:06) Analyzing a potential startup market (51:23) How successful products eventually become distribution companies (56:30) Non-obvious startup advice (59:54) When its OK to give up (01:02:20) Advice on raising your first round (01:03:21) Picking board members (01:04:45) How to hire your first three employees (01:06:48) Avoiding bad hires (01:08:39) The importance of speed of execution (01:12:36) Why he’s adding to his team (01:14:31) Gardening Referenced: Elad’s Blog: https://blog.eladgil.com/ Elad’s Podcast: https://www.youtube.com/@NoPriorsPodcast/ Elad’s Book: https://growth.eladgil.com/ Where to find Elad: Twitter: https://twitter.com/eladgil LinkedIn: https://www.linkedin.com/in/eladgil Elad’s Website: https://eladgil.com/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

This episode is brought to you by Warp. Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1000 gift card when you first run payroll. Celine Halioua is the founder and CEO of Loyal, a biotech company developing medicine to help dogs live longer and healthier lives. And dogs are just the start - Celine thinks Loyal could one day do the same for humans. She takes us inside what it’s like to build a biotech company from scratch. We talk through how Loyal’s longevity drugs work, the process of getting FDA approval, her biggest mistakes as a founder, how to approach building in a new market, lessons learned failing to raise her Series B, why rate of growth is all that matters in hiring, and almost not starting the company in the first place. Timestamps: (00:00) Preview (03:30) How a longevity drug works (06:08) Predictions around longevity (08:26) Why Celine cares so much about not failing (12:05) Differences between biotech and software startups (14:15) Sizing a new market (16:53) Why biotech startups are more dilutive early on (20:22) Getting FDA approval (22:57) Why its hard to prove longevity drugs actually work (24:48) The reason Loyal started with dogs (25:27) How Loyal’s drug slows aging (33:42) Working on longevity to increase free will (34:25) Culture shock at Oxford and dropping out of her PhD (37:22) What makes Josh Koppelman a good VC (39:44) Celine’s two biggest mistakes as a founder (42:39) Why rate of growth is the best indicator of success but the hardest to predict (45:33) Self awareness & how being a CEO is both fun and miserable (48:11) How Laura Deming convinced her to start Loyal (50:18) Finding the science behind Loyal (54:21) Deciding it was the right path to start a company (56:30) Lessons from failing to raise a Series B initially (1:02:18) Why Silicon Valley can build 10x more deep tech startups (1:04:05) Doing big things that improve the world (1:04:50) What Celine looks for in startups Where to find Celine: Twitter: https://twitter.com/celinehalioua LinkedIn: https://www.linkedin.com/in/celinehh/ Celine's Website: https://www.celinehh.com/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Rahul Sonwalkar is the founder and CEO of Julius, an AI data scientist. He takes us inside his epic “Ligma Johnson” prank where he pretended to be fired from Twitter the day Elon acquired the company. He then goes inside his journey of building Julius, sharing lessons learned along the way and his vision for the product. Timestamps: (00:00) Preview (04:16) The "Ligma Johnson" prank (09:02) Meeting Elon (13:10) Doing hackathons in college (14:30) Scraping emails from Hacker News to get internships (16:25) Using Twitter to learn and meet people (22:26) Lessons from his first failed startup (26:19) Taking too long to quit Big Tech & his failed startup idea in trucking (32:12) Convincing Guillermo Rauch to invest with speed of execution (34:48) How to avoid analysis paralysis (36:15) Building Julius, the AI data scientist (39:25) How COO of a hot tub company uses Julius (40:40) Professor embracing AI, using Julius to teach his class (42:47) Iterating on early versions of the product (44:42) PMF is as much about the market as the product (45:08) Building dozens of ChatGPT plugins to acquire Julius’ first users (45:41) Using dev API keys and missing the first paying customers (49:22) Talking to hundreds of early customers (50:10) Why customers love when you ship new features every week (52:14) The power of Julius’ small team (54:38) Why Rahul gives his number to customers (57:47) How to avoid idea backlogs (59:27) Why Julius tests so many models (01:01:44) Why it feels great when people love your product (01:03:43) AI will write more code than humans (01:06:33) Giving an AI a computer (01:11:05) What happens to all the AI startups? (01:12:36) Why you have to Ride the Tiger (01:16:43) How NVIDIA beat 89 other graphics card startups (01:20:14) Building a moat as a startup (01:22:50) Rahul’s favorite AI companies (01:25:11) Why Julius’ changes UI components based on the use case (01:27:42) Benefits of lifting (01:29:54) Why Rahul loves SF (01:31:38) The early days of Microsoft Referenced: https://julius.ai/ Guillermo’s tweet: https://x.com/rauchg/status/1773168477957919055 Where to find Rahul: Twitter: https://twitter.com/0interestrates LinkedIn: https://www.linkedin.com/in/rahulsonwalkar23 Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel Bill Shufelt is the Founder and CEO of Athletic Brewing, the craft brewer that created the non-alcohol beer market in the US. Bill takes us inside the early days of starting the company, including realizing there was an opportunity to make non-alcoholic beer, finding a co-founder, struggling to find early investors, building multiple breweries, and getting into Whole Foods before launching. Our conversation is a case study on creating a new market - I hope you enjoy. Timestamps: (00:00) Preview (04:10) Becoming the #1 beer in Whole Foods(05:54) The history of non-alcoholic beer(10:41) Why an outsider had to create this new category(15:34) Health benefits of avoiding alcohol(17:51) Turner tries the beer(22:49) Bill’s wife pushing him to start Athletic Brewing(26:38) Writing a 96 page white paper on non-alcoholic beer(28:42) Quitting his job to start six months of research and networking(30:21) Meeting the perfect co-founder after 100’s of meetings(32:34) Putting his life savings into a warehouse and brewing equipment(33:04) The importance of setting company values early on(34:23) Brewing the first beer in Gatorade jugs(36:16) Selling the first bottles to retailers(37:42) Explosive growth in 2019(39:39) Why new products and D2C helped them scale so fast(40:39) Using TikTok to sell-out new product launches in 30 seconds(42:00) The value of doing early customer service himself(44:45) Getting to 61% market share in non-alcoholic beer(46:10) Struggling to raise the first angel round(48:34) Using consistent investor updates to easily raise the Seed, Series A, and Series B(50:47) Transitioning to institutional capital for its Series C(52:33) Betting on a new category to expand market size(55:44) Information access is enabling healthier consumer behavior(58:11) Bill’s early strategy for marketing the product(1:01:43) The importance of over communicating with your investors(1:03:44) Why retailers like Athletic Brewing’s unique omni channel approach(1:06:16) How building its own breweries and supply chain enabled its unique strategy and better margins at scale(1:09:04) Getting into Whole Foods before launching(1:11:31) Doing unscaleable things over and over again(1:13:50) Why entrepreneurship is a long game(1:14:22) Most of Athletic’s new products come from the team Check out Athletic Brewing: https://athleticbrewing.com/ Where to find Bill: LinkedIn: https://www.linkedin.com/in/bill-shufelt-650059138 Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Dane Atkinson is the Founder and CEO of Odeko, the all-in-one operations partner for local businesses. Dane has spent his entire career helping small businesses. This episode is a masterclass on selling to SMBs. He shares all his lessons learned as a founder, and how Odeko survived zero revenue during COVID and hit $150 million in revenue two years later. Timestamps (00:00) Intro (03:33) The magic formula to sell to SMBs (04:06) Why every small business starts as a dream (21:57) The reasons you shouldn’t listen to customers (25:16) Lessons running Squarespace for four years (27:12) Why simplicity is better for SMBs (28:58) How Squarespace ran the very first podcast ads (35:35) Lessons messing up his second company (37:46) How to demote an employee (50:29) Coming up with the idea for Odecco (52:05) Why VCs screw their portfolio companies (55:16) How to navigate pivots with your board (01:04:27) Growing revenue from zero to $100m+ in two years (01:12:10) Advice for first-time founders (01:14:18) How Dane would re-design the food system (01:15:39) Why our food is so bad for our health (01:16:17) How Odeko empowers local makers Check out Odeko: https://odeko.com/ Where to find Dane: Twitter: https://twitter.com/daneatkinson LinkedIn: https://www.linkedin.com/in/daneatkinson Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Josh Miller is CEO and co-founder of The Browser Company, which is building a new internet browser. He explains why effective hiring requires caring a lot and trusting your taste and why Arc Search, a default mobile browser, could be The Browser Company’s next act. TIMESTAMPS: (00:00:00) Intro (00:02:35) Working for Obama (00:03:55) Giving up 8-figures in Meta stock (00:08:19) Barack Obama’s favorite web browser (00:09:02) Why Arc released a mobile browser (00:10:03) How Josh met Josh Kushner (00:11:26) Becoming an EIR at Thrive Capital (00:12:09) How The Browser Company got started (00:15:51) Why they named it The Browser Company (00:18:49) Pivoting to consumer when COVID hit (00:20:37) Leaving Thrive to join as a Co-founder in February 2020 (00:21:05) Why COVID made browsers relevant (00:22:42) How to hire a great team (00:25:02) Hiring Josh Lee to edit their videos (00:26:52) The biggest difference between Josh as a first-time and second-time founder (00:28:46) Learning to delegate (00:34:03) Why Thrive gave up double-digit equity back to the founders (00:40:18) Launching (00:40:52) Why build a web browser (00:42:17) This history of browsers (00:43:36) Why they’ve gotten worse over time (00:50:26) The reasons people use Arc (00:53:23) How Arc will make money (00:56:45) Why Arc’s existential question is getting people to care about their browser (00:59:47) The story behind Arc Search (01:00:45) Arc’s potential growth flywheel (01:09:17) Why Arc bet big on building in public on YouTube (01:10:16) The publisher backlash to Arc Search (01:11:33) Why praising your team publicly is so important (01:13:39) How Josh hired Nate Parrott More on The Browser Company: https://thebrowser.company/ https://arc.net/https:// www.youtube.com/c/TheBrowserCompany Where to find Josh: Twitter: https://twitter.com/joshm LinkedIn: https://www.linkedin.com/in/josh-miller-b31259106 Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel Peter Walker is Head of Insights at Carta and writes a newsletter called “The Data Minute”, a weekly newsletter highlighting data from over 43,000 private tech companies that use Carta’s platform to manage their cap table. He gives us into a deep dive on VC valuation trends, the fundraising landscape, and startup strategies. Timestamps: (00:00) Intro (04:50) Valuation trends in 2023 (08:10) Why Seed valuations went up over the past two years (12:27) AI startups are getting higher valuations (17:40) Why Biotech might be the next big bubble (19:15) Boston as the 2nd largest VC ecosystem (21:15) How SAFE’s work (24:06) The impending SAFE reckoning (26:13) Why startups don’t pay dividends (28:31) Downrounds were 2x more common in 2023 (32:11) Almost half of all 2023 Series As were extensions (35:34) Is there really a lot of dry powder? (40:43) The emerging manager fundraising landscape (48:19) Exit environment (51:45) Why pre-Series B is the most common acquisition stage (52:47) Liquidation preference & why an acquisition at Seed might make a founder more money than at a Series B (55:59) Compensation market data (56:38) Why the number of total startup employees shrank in 2023 (57:38) Why startup employees aren’t exercising their options (1:00:57) Health of the secondary markets (1:04:51) Most co-founder splits aren’t 50/50 (1:06:47) Why you should always vest co-founder equity (1:09:30) 2023 record year for startup shutdowns (1:17:19) Will other startup ecosystems ever catch Silicon Valley? Links: Carta’s Q4 ‘23 Private Market Report: https://carta.com/blog/state-of-private-markets-q4-2023/ Peter’s Newsletter: https://carta.com/subscribe/data-newsletter-sign-up/ Where to find Peter: Twitter: https://twitter.com/PeterJ_Walker LinkedIn: https://www.linkedin.com/in/peterjameswalker/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Chris Bakke has founded and sold three companies for between $25-100 million to Zillow, Indeed, and most recently Twitter / X. He shares how he convinced Elon to buy his company, what it's like working for Elon, exactly how the Twitter algorithm works, and all his meme making secrets. — — — — Timestamps: (00:00) Intro (02:52) Inside Twitter’s acquisition of Laskie(05:38) Why Twitter / X works so well for recruiting(08:11) A sneak peek at upcoming Premium features(13:58) How the X algorithm works(20:48) Why “dwell time” is the most important metric(24:07) What it’s like reporting to Elon(27:40) Elon’s crazy ability to context-switch(29:16) Why you should consider selling your company for $25-100 million(35:39) The reasons large M&A deals are so rare(42:07) Surviving inside Big Tech as a founder(46:23) Chris's philosophy on company building(51:23) Why “Time in Market” is so underrated(53:44) YC’s “sandwich incident”(55:44) How to use memes for marketing(58:55) Chris’ 100+ page Google Slide meme library(1:01:46) His top three favorite meme templates(1:03:48) His favorite proprietary trade secret at X(1:05:03) Turning down jobs at Coinbase and WhatsApp — — — — Twitter jobs: https://twitter.com/jobs — — — — Where to find Chris Twitter: https://twitter.com/ChrisJBakke LinkedIn: https://www.linkedin.com/in/bakk3/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel Mike is currently a partner at Lightspeed Venture Partners. Before Lightspeed, he spent five years building Anchor, which he sold to Spotify in 2020, and then led Spotify’s podcast, video, and live products for three years. It's probably safe to assume every podcast you listen to uses Mike’s product, and we go way back to the very beginning and talk through how the team at Anchor pulled it all off.Mike also shares his frameworks of “Doing the Dumb Thing” and "Super Goals," which are high-stakes, focusing goals with a clear and urgent time frame, open-ended method of achievement, and a single measure of success. Chapters: (00:00) Intro (4:22) Why AI makes consumer investing interesting again (8:05) Podcasting in the early 2010’s (14:03) The benefits and drawbacks of RSS (21:50) Building v1 “Instagram for audio” (25:53) Advice for building a close-knit community (29:28) Raising their first small round (31:38) Inside their splashy launch at SXSW (39:17) Why the first product failed, but allowed them to raise money to build Anchor (45:26) What makes a good product founder (47:39) Re-launching v2 a year later (53:51) What is a Super Goal (56:32) Finding Product Market Fit with months of runway left (59:02) Getting to a million podcast creators (01:02:09) Launching the first podcast ad network (01:04:10) Why anchor started sponsoring its own ad network (01:08:13) Spotify’s acquisition of Anchor (01:14:22) How Spotify won in podcast market share (01:16:34) Why the future of podcasts is video Referenced: Mike’s Podcast “Generative Now”: https://www.youtube.com/playlist?list=PLXW6zY9x-gk1oPyjZ_qBCDEYKTbPpGa8S Mike’s blog posts: https://mignano.substack.com/p/the-standards-innovation-paradox https://mignano.substack.com/p/the-power-of-supergoals https://mignano.substack.com/p/startups-vs-incumbents-the-battle https://mignano.substack.com/p/all-podcast-roads-lead-to-video Where to find Mike: Twitter: https://twitter.com/mignano LinkedIn: https://www.linkedin.com/in/mignano Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Eric Newcomer is the founder of Newcomer, a publication he launched in October of 2020 to cover the business of startups and venture capital. He had just left Bloomberg after nearly six years, and was previously the first employee at The Information. — — — — Timestamps: (00:00) Intro (02:46) The current state of media (05:59) Anchoring his 4th grade newscast (07:21) Becoming the 1st employee at The Information (09:34) How reporters get stories (21:12) The moment he quit Bloomberg to start Newcomer (26:02) Why he writes for VC insiders (32:19) The VC top fund survey (34:01) The Founders Choice VC leaderboard (35:51) Why leaked documents grow his newsletter the fastest (39:45) When Eric knew Newcomer was going to work (43:31) How events become Newcomers most profitable business (51:56) Why Eric invested in Substack (57:42) Why its harder to cover tech’s downturn than boom times (59:10) How to pitch a story to a reporter (01:02:59) Why the internet incentivizes negative media coverage (01:06:06) Advice for starting a media company (01:10:33) Why media works so well to sell adjacent products (01:12:55) Newcomer Banking Summit (01:14:27) The $1.3B acquisition that happened at his first conference (01:20:05) New products Eric’s thinking about — — — — Referenced: Newcomer Passes $1m in Revenue: https://www.axios.com/2024/01/04/substack-writer-eric-newcomer-says-his-revenue-surpassed-1m-in-2023 Pragmatic Engineer Newsletter: https://blog.pragmaticengineer.com/ Lenny’s Newsletter: https://www.lennysnewsletter.com/ Mike Solana’s Pirate Wires: https://www.piratewires.com/ Mentioned Newcomer Articles: VC Survey: https://www.newcomer.co/p/sequoia-founders-fund-usv-elad-gil Founder's Choice: https://www.newcomer.co/p/founders-choice-vc-rankings-revealed Paywalled Bill Gurley Interview: https://www.newcomer.co/p/above-the-crowd SBF’s Leaked FTX Email: https://www.newcomer.co/p/exclusive-read-sam-bankman-frieds Eric’s first article on Sequoia: https://www.newcomer.co/p/sequoias-political-paradox — — — — Where to find Eric: Twitter: https://twitter.com/EricNewcomer LinkedIn: https://www.linkedin.com/in/ericpnewcomer/ Newsletter: https://www.twitter.com/newcomer Email: newcomer@newcomer.co Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Siqi Chen is the Co-Founder and CEO of Runway, the modern and intuitive way to model, plan, and align your business for everyone on your team. Or, in Siqi’s words, “revolutionizing the $80 trillion business industry”. A few months ago, Runway’s new website went viral across the internet. Siqi takes us inside how that happened. He’s no stranger to going viral, having previously built multiple companies that went from zero to millions of users within weeks, including the fastest growing product ever before ChatGPT took the crown in late 2022. — — — — Brought to you by Attio, the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at ⁠https://bit.ly/AttioThePeel⁠ — — — — Timestamps: (00:00) Intro(02:00) Sponsor: Attio (02:59) How Siqi goes viral (06:13) Why conversion doesn’t always matter (11:23) How to make B2B software more fun (14:31) Working on the Curiosity and Spirit rovers at NASA (16:50) Re-designing at the entire codebase and product at his first startup job (21:13) Earning the nickname “FB Millz” making a million dollars building Facebook games (25:11) Selling to Zynga and building the fastest growing product before ChatGPT (28:36) Building a game with 90% Day 1 retention (30:09) Being played by Kim Kardashian, Jack Dorsey, and shut down by Tim Cook (32:10) Almost getting fired building a growth team at Postmates (35:04) Building Sandbox VR: “escape rooms in VR” (40:35) Meeting Kanye (44:38) Getting the idea for Runway when COVID hit (47:32) Why spreadsheets run every business (54:40) Disrupting the $80 trillion business industry (57:55) Making formulas 50x easier than Excel (01:02:32) Why Runway’s building a painkiller (01:06:32) How to fundraise (01:08:32) Why the first question from an investor is the reason they won’t invest (01:11:28) How to tell a company’s story (01:15:23) The three layers of a story (01:17:28) The importance of positioning in storytelling (01:18:56) Runway’s flexible remote work strategy (01:21:34) Why their hiring strategy changed over time (01:22:39) Siqi’s single interview question & the three traits he looks for when hiring (01:26:10) Unlearning consumer to learn B2B (01:30:26) Navigating the first three years of no customers (01:31:45) What surprised Dylan Field the most about building Figma — — — — Referenced: Runway’s website: https://runway.com/ Reform Collective Design Agency: https://www.reformcollective.com/ Amplitude: https://amplitude.com/ SandboxVR: https://sandboxvr.com/ Lulu Cheng’s Android Playbook: https://www.piratewires.com/p/anduril-comms-strategy-early-days — — — — Where to find Siqi: Twitter: https://twitter.com/blader LinkedIn: https://www.linkedin.com/in/siqic/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Shrav Mehta is the Founder and CEO of Secureframe, which empowers businesses to build trust with customers by automating information security and compliance. Shrav started the company in 2019 after being an early employee at Scale, Pilot, Lob, and Hired, and has since raised from investors like Kleiner Perkins, Backend Capital, Soma Capital, and Banana Capital. Shrav takes us inside how Secureframe’s automating the compliance market, lessons learned on recruiting and scaling teams, and his contrarian take on finding product market fit. — — — — Timestamps: (00:00) Intro (2:10) Automating the $80 billion compliance market (15:49) Learning to program building Android apps (22:50) Joining Lob, Hired, and Scale early (27:25) Joining Pilot to learn marketing and growth (33:31) Shrav’s secret discount furniture supplier (35:04) Finishing three years of college in one year (39:06) Getting 30-40 customers before starting Secureframe (44:24) Non-intuitive fundraising advice from pre-product to IPO (50:08) Why the IPO isn't the ultimate goal (54:40) How Shrav approaches hiring (58:04) Tactics for effective reference checks (1:01:01) Why warm intros are so helpful (1:02:32) How to send good cold emails (1:05:31) Why you should not use LinkedIn “open to work” (1:06:54) Lessons learned scaling teams (1:13:45) Why finding PMF is a 24/7 job and never ends — — — — Referenced: Secureframe: https://secureframe.com/ Lob: https://www.lob.com/ Hired: https://hired.com/ Scale: https://scale.com/ Zapier’s Secrets to PMF: https://www.youtube.com/watch?v=NJMjuYt9jEc What it took to raise a Series A in 2023: https://news.crunchbase.com/venture/seed-to-series-a-funding-2023-jones-kruze — — — — Where to find Shrav: Twitter: https://twitter.com/shravvmehtaa/ LinkedIn:https://www.linkedin.com/in/shravmehta/ Where to find Turner: Twitter: https://twitter.com/turnernovak/ LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Kevin Espiritu is the founder and CEO of Epic Gardening, which is, by multiple measures, one of the largest brands in gardening on the planet.What started in 2013 as a blog has since evolved into a gardening empire spanning YouTube, TikTok, Instagram, Facebook, 4,500 gardening stores, and three gardening books. Epic raised a $17.5m Series A from The Chernin Group in 2021, and according to external sources did $27 million in revenue in 2022. — — — — Brought to you by Attio, the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioThePeel — — — — Timestamps: (00:00) Intro (04:03) Sponsor: Attio (05:09) A deep dive on the history of YouTube (12:04) The YouTube algorithm and meta game (40:17) Using Reddit to drive initial blog traffic (46:56) How creator-led businesses have negative CAC (47:12) Why creator businesses must be very small or very large (49:38) How YouTube is changing today (50:00) Acquiring a gardening blog for $1k from an Indian VC (52:43) His process for doing acquisitions (53:38) Launching his first product (57:54) His biggest mistakes launching new products (58:30) Buying his own warehouse (59:04) Non-intuitive ways a product can influence your cost structure (1:03:00) Kevin’s approach to hiring (1:04:40) Why he raised a Series A as a YouTube creator (1:05:27) How to approach investing in AI (1:19:53) Why Kevin wrote three books (1:23:26) Why more people will grow food at home (1:25:20) How he approaches celebrity partnerships — — — — Referenced: Epic Homesteading: Your Guide to Self-Sufficiency on a Modern, High-Tech, Backyard Homestead https://www.amazon.com/Epic-Homesteading-Self-Sufficiency-High-Tech-Homestead/dp/0760383766 MrBeast https://www.youtube.com/@MrBeast MrBeast's Feastables https://feastables.com/ Logan Paul x KSI PRIME https://drinkprime.com/ MatPat of @GameTheory https://www.youtube.com/channelUCo_IB5145EVNcf8hw1Kku7w Michelle Phan https://www.youtube.com/user/michellephan Ipsy: https://www.ipsy.com/ by Michelle Phan Matthew Beem https://www.youtube.com/channel/UCR_J_SntqJh5eXw66d5hJxA The Chernin Group https://tcg.co/ — — — — Where to find Kevin / Epic Gardening Twitter: https://twitter.com/KevinEspiritu YouTube 1: https://www.youtube.com/user/kevinmespiritu YouTube 2: https://www.youtube.com/@epicgardening Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/

Kirsten Green is the founder of Forerunner Ventures, a venture capital firm that focuses on understanding the mindset of the modern consumer. Kirsten started Forerunner in 2010, and was an early investor in companies like Faire, Chime, Warby Parker, Dollar Shave Club, Hims, Glossier, Jet, Bonobos, HotelTonight, and The Farmer’s Dog. This episode takes us behind the scenes of Kirsten’s two decade journey building Forerunner from scratch. She talks about her biggest mistakes, wins, and lessons learned along the way. Timestamps: (00:00) Intro (02:50) Doing market research at the mall  (08:00) Her journey from public markets to venture (18:30) Lessons from her first investment going to $0 (28:51) How she raised her first $5m angel fund (31:11) Transitioning to a $41.7m institutional fund (43:20) Why she almost didn’t invest in Dollar Shave Club (sold for $1.1 billion) (51:05) How Forerunner thinks about fund size (57:05) How she led Faire’s Series A with a small fund (58:46) How Kirsten builds relationships with LPs (01:02:10) Is consumer investing dead? (01:15:00) Her unfair advantage as an investor Where to find Kirsten Twitter: https://twitter.com/kirstenagreen LinkedIn: https://www.linkedin.com/in/kirstengreen Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/

Craig Fuller is the Founder and CEO of FreightWaves, a media company and data provider for the global supply chain. He’s also the CEO of Flying Media Group, which he founded in 2021 to acquire Flying Magazine, the largest US-based print magazine for the aviation industry. This conversation is split into three parts: a crash course on logistics and supply chains, how to build and run a media company, and finally all things print magazines. Topics discussed include: (00:00) Intro (02:39) Why logistics is the most important industry no one talks about (04:23) The rise of deglobalization (11:07) How Colombia benefits from US manufacturing (14:52) Why Craig’s watching US onshoring and Mexican nearshoring (18:18) How the supply chain function is changing (28:59) The US labor availability problem (32:40) Why AI will never fully replace humans in media (34:56) The early days of FreightWaves (41:04) Predicting recessions months before it shows up in data (48:51) Why logistics is the best barometer of the global economy (52:44) Taking 12+ months to raise FreightWaves first venture round (59:24) Surviving COVID with only two months of runway (01:05:20) How FreightWaves accidentally became a media business (01:08:15) Why the best startups make low risk, high upside decisions (01:13:27) Why media business are the arbitrage opportunity this decade (01:15:55) Getting 200%+ IRR’s buying print magazines, starting with flying (01:17:50) Building his own airport and flying community (01:30:16) Almost failing to turnaround his first magazine acquisition (01:39:06) His non-intuitive lessons from building media businesses (01:43:39) Craig’s favorite media businesses (01:48:50) How to build a brand in media Referenced: https://www.freightwaves.com/ https://www.flyingmag.com/ Where to find Craig: Twitter: https://twitter.com/FreightAlley LinkedIn: https://www.linkedin.com/in/incab Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Danielle Cohen-Shohet is the CEO and Founder of GlossGenius, the all-in-one booking, payments and POS solution that helps beauty and wellness professionals drive bookings and grow their business. Danielle started the company in 2016 and has since grown it to a $510 million valuation. This is while taking a disciplined approach to fundraising, raising roughly $70 million throughout the life of the company. — Topics include: A crash course on the $160 billion beauty, health, and wellness market How the industry's shifting to time-based billing and upfront payments Why GlossGenius spends so much time on customer experience Surviving a 90% drop in revenue during COVID Why she credits talking to and listening to customers to GlossGenius success A look inside each funding round, and why Danielle kept them small How she learned to delegate as the company scaled Why the big picture is often made of little details Danielle’s secret for running a capital efficient business GlossGenius’ Hiring and Interviewing Manual Why most companies aren’t good at hiring Danielle’s favorite interview questions — Where to find Danielle: Twitter/X: https://twitter.com/dcohenshohet LinkedIn: https://www.linkedin.com/in/dcohenshohet — Where to find Turner: Newsletter: https://www.thespl.it Twitter/X: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io —For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Cristina Junqueira is the Co-founder and Chief Growth Officer of ⁠Nubank⁠, the largest neobank in Latin America – and in the world – with more than 80 million customers. She is also the second self-made female billionaire in Brazil. Cristina and her co-founders David Vélez and Edward Wible launched Nubank in 2013, essentially building the fintech category in a market where it was nonexistent, and went on to release a no-fee credit card, app, and other banking products across Brazil, Mexico, and Colombia.Cristina takes us through the rise of Nubank, from the scrappiest days building in a house in Sao Paulo to being backed by investors like Sequoia, Founders Fund, DST, TCV, Tiger Global, and Warren Buffett, and then on to their IPO in December 2021. We also touch on the impact of Nubank’s distinctive brand choices, how they navigated government regulations that nearly shut them down, and how they were able to spend $0 on marketing throughout most of their history.— — — —TIMESTAMPS:(00:00) Preview(02:38) Fintech and the preconditions for disrupting financial services in LatAm(05:38) Educating investors on the opportunity for fintech in LatAm(07:35) The scale of unbanked and underbanked populations in Brazil, Mexico, and other countries; and why expanding access to these products increases NuBank's market share(08:21) Expanding the pie and just how profitable banks can be in LatAm(15:37) Starting NuBank and the lessons Cristina learned from incumbent banks(18:11) The biggest hurdle to starting NuBank(19:33) Navigating Nubank’s first product from inception to successful credit card(21:08) Spending $0 CAC in an industry with hugely expensive marketing pushes(22:32) $0 on marketing and scrappy ethics(26:40) The crazy circumstances around Nubank’s Series A fundraise(36:54) Cristina’s reflections on the IPO in December 2021 (39:31) How Nubank navigates a changing macro environment(40:40) The importance of Nubank’s distinctive brand(42:57) Surviving an existential threat from Brazil’s government(46:28) Scaling from a small scrappy team to a multinational global publicly traded company(49:02) Personal growth and maintaining strong co-founder relationshipsReferenced:Nubank: ⁠https://nubank.com.br/en/Nubank's IPO mints Cristina as a billionaire: https://www.forbes.com/sites/jeffkauflin/2021/12/09/Where to find Cristina:Twitter: https://twitter.com/junqueira_crisLinkedIn: https://www.linkedin.com/in/crisjunqueira/Where to find Turner:Newsletter:https://www.thespl.itTwitter: https://twitter.com/TurnerNovakBanana Capital: https://bananacapital.vc

Sid Yadav is the Co-founder and CEO of Circle, the all-in-one community platform trusted by creators like Tiago Forte, David Perell, and Miles Snider. Sid started the tech blog Rev2 when he was a teenager in New Zealand, writing about the launch of YouTube and the iPhone. He was the founding engineer and designer of Teachable, which he helped scale to +25m+ in ARR before it was acquired in 2020. He started Circle in 2019 with co-founders Rudy Santino and Andrew Guttormsen, which they scaled to $16m in ARR by December of 2023. Circle has since raised $31m from Investors like Tiger Global, Notation Capital, Bungalow, Todd Goldberg, Rahul Vohra, Scott Belsky, Josh Buckley, Ankur Nagpal, Wade Foster, and Dharmesh Shah. Sid immigrated with his family from India to New Zealand as a teenager and to the US after college. His story is a perfect encapsulation of the American Dream, and I’m excited to share this conversation. — — — — Brought to you by Deel, the global HR + payroll platform used by 20,000+ teams. Deel’s in-house immigration team gets you and your team worldwide visas without the legwork. Book a Demo: bit.ly/thepeelxdeel — — — — Topics discussed include: (03:53) Why the creator economy is booming despite negative sentiment (13:22) Writing a popular tech blog as a teen in the mid 00’s (23:16) Joining Teachable as the 2nd employee (40:30) Why Teachable CEO Ankur Nagpal invested 90% of his liquid net worth in Circle’s $1.7m Pre-seed round (48:44) Sid’s inside view at the creator economy before, during, and after COVID (52:50) The magic of Lenny Rachitsky’s creator flywheel (56:10) The reason Sid raised a Seed from lots of investors instead of one large check (01:14:30) Inside raising a Series A from Tiger Global in 2021 (01:22:19) Why Sid writes an investor update every month (01:25:15) Going from Zero to $16m ARR in four years (01:27:28) How Circle approaches its product roadmap (01:29:20) Building a community around your product (01:37:03) Advice for running a remote-first team (01:46:54) How Sid convinced the founder of Zapier to be his CEO coach (01:54:20) Why founders need to deal with reality Referenced: https://circle.so/ https://www.teachable.com “Cost of a meeting” tweet: https://twitter.com/0xgaut/status/1620815168921038850 Tiago Forte Building a Second Brain: https://www.buildingasecondbrain.com/foundation PARA Method: https://fortelabs.com/blog/para/ Lenny’s interview with Brian Chesky: https://www.youtube.com/watch?v=4ef0juAMqoE Turner’s interview with Wade Foster, Co-founder and CEO of Zapier:  https://youtu.be/NJMjuYt9jEc Myles Snyder: https://mylessnider.com/ Where to find Sid: Twitter: https://twitter.com/sidyadav LinkedIn: https://www.linkedin.com/in/sidyadav Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc

Pim de Witte is the Co-founder and CEO of Medal, which enables millions of gamers to capture and share their favorite gaming moments with friends. Pim started the company in 2015 and has since raised over $72 million, supported by investors like OMERS Ventures, Makers Fund, Dune Ventures, and Horizon Ventures.Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGCRead the transcript: https://www.thespl.it/p/growing-medal-to-tens-of-millionsIn this episode, we discuss: Why we play video games Why 200 million gamers play Roblox Learning to code at 13 to build a private Runescape server that did $1.5 million in revenue Why paid acquisition is so important in mobile gaming Why consumer platforms need a social inflection point How Medal blew up during COVID Why multiplayer platforms die when network effects unravel Why Medal’s Seed round was so hard to raise Pim’s biggest mistake building Medal His three favorite interview questions Medal’s unique hybrid in-person / remote work environment Why it’s a mistake to focus on competitors instead of customers Why rapid iteration is everything How to acquire another startup Why building product is the ultimate game How Elon’s changes at Twitter caused a great reset in techWhere to find Pim:Twitter: https://www.twitter.com/PimDeWitteLinkedIn: https://www.linkedin.com/in/pimdw/Where to find Turner:Newsletter: https://www.thespl.itTwitter: https://twitter.com/TurnerNovakRead the transcript: https://www.thespl.it/p/growing-medal-to-tens-of-millionsProduction and distribution by: https://www.supermix.ioFor sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Itai Damti is the Co-founder and CEO of Unit, the platform that helps leading tech companies store, move, and lend money.Unit has raised over $170 million from investors like Better Tomorrow Ventures, Accel, Insight, and dozens of angels. — In this episode, we discuss: The first and second wave of fintech innovation How the second wave brings financial services inside other software How Unit beat the competition and raised $170 million by focusing on product and expanding the market size Itai’s framework for leveraging his investors His strategy for prioritizing as a founder How Unit operates with precision And why they haven’t built any crypto products — Brought to you by Artie, the real-time database replication solution that sets up in minutes and requires zero day-to-day maintenance. Sign-up for a demo and get two weeks free: https://bit.ly/3uWTzWJ — Where to find Itai: Twitter: https://twitter.com/itaidamti LinkedIn: https://www.linkedin.com/in/itaidamti — Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io —For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Kevin Liu is the Co-founder and CEO of Metronome, which enables software companies to launch, iterate, and scale their business models with billing infrastructure that works at any size and stage. Prior to Metronome, Kevin and his co-founder Scott Woody both sold their respective separate companies to Dropbox. Kevin and Scott started Metronome in 2019, and have since raised over $30 million from investors like a16z, General Catalyst, Elad Gil, Lachy Groom, and dozens of other angels. — Brought to you by Artie, the real-time database replication solution that sets up in minutes and requires zero day-to-day maintenance. Sign-up for a demo and get two weeks free: https://bit.ly/41gQbSy — In this episode, we discuss: The history and evolution of software business models A crash course on all things software pricing Kevin’s framework for iterating on new startup ideas His 2-days on, 1-day off strategy for early customer needfinding How he leveraged angels to raise Metronome’s Seed and Series A rounds The dangers of over-building a product Why Metronome sacrificed its own margins to scale with OpenAI How Kevin thinks founders should prioritize their time Frameworks for building a pricing model The biggest pricing mistakes companies make — Referenced: https://www.metronome.com — Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevinyliu — Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io —For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Wade Foster is the Co-founder and CEO of Zapier, an automation platform that helps you work faster. Wade and his co-founders Mike and Bryan started the company in 2011, and have always done things a bit differently. From being a startup based in Missouri, working as a remote team since 2011, and raising very little outside capital despite being one of the fastest growing startups in the world. — Brought to you by Secureframe, the automated compliance platform built by compliance experts. Get compliant with security and privacy frameworks like SOC 2, ISO 27001, HIPAA, GDPR, and more. Sign-up here: https://bit.ly/3QOr2eo — Topics discussed include: The founding story of Zapier Wade’s contrarian take on Product Market Fit Why new products are usually built on emerging distribution channels How Wade deals with imposter syndrome Never raising more money after a $1.3 million Seed during YC How Zapier thinks about it’s product roadmap Shutting the company down for a weeklong AI hackathon Why Wade thinks LLMs will unlock new types of product interfaces How he delegates work without losing track of the details — Referenced: https://zapier.com — Where to find Wade: Twitter: https://twitter.com/wadefoster LinkedIn: https://www.linkedin.com/in/wadefoster — Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io — Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Gaurab Chakrabarti and Sean Hunt are the Co-founders of Solugen, which replaces petroleum based products with plant-derived substitutes without sacrificing affordability or performance. They met playing poker in college, kickstarted the company with $10k from an MIT pitch competition, and have since scaled the business to over nine-figures in revenue. Solugen has raised over $642 million from investors like Fifty Years, Lowercarbon Capital, Founders Fund, Refactor Capital, and Cantos Ventures. — Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/47sxTQ0— Topics discussed: How the chemicals industry touches 25% of US GDP Why the industry is like real estate: fragmented and focused on asset utilization The reason chemicals companies have terrible NPS scores How Solugen’s manufacturing process converts plants and C02 into chemicals Meeting over a game of poker while getting their PhD’s Winning $10k from an MIT pitch competition to capture 10% of the float spa market in Dallas, Texas Why the first wave of Cleantech startup fail Why logistics and supply chain are the biggest problems in Chemicals Their framework for thinking big, but taking little steps to get there Running their homemade metal catalyst reactor at YC Demo Day Launching, scaling, and selling a CPG wipes company to prove their chemicals worked Building their first factory (the BioForge) on the site of an exploded wax distillery Their strategy for getting large, multinational companies to try their products — Referenced: YC Application video: https://www.youtube.com/watch?v=tItLPnLIH4o Solugen - The First Carbon Negative Molecule Factory: https://jeffburke.substack.com/p/solugen-the-first-carbon-negative Solugen - The Century of Biology: https://centuryofbio.com/p/solugen — Where to find Gaurab: Twitter: https://twitter.com/gaurabc LinkedIn: https://www.linkedin.com/in/gaurabchakrabarti — Where to find Sean: Twitter: https://twitter.com/TungstenSeanide LinkedIn: https://www.linkedin.com/in/huntsean — Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak — Production and distribution by: https://www.supermix.io —For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Jonathon Barkl is the Co-founder and CEO of AirGarage, a full-stack parking management company that helps real estate owners increase their income.Jonathon and his co-founders Chelsea and Scott started the company in 2017. They’ve since raised roughly $15 million from investors including Founders Fund, Floodgate, a16z, Abstract, and prior guest of the show Ryan Delk.— Brought to you by Secureframe, the automated compliance platform built by compliance experts. Get compliant with security and privacy frameworks like SOC 2, ISO 27001, HIPAA, GDPR, and more.Sign-up here: https://bit.ly/3QOr2eo— Topics discussed: A crash course on the business model of parking Why parking lots make most of their money from tickets and towing The reason American cities dedicate up to 30% of space to parking How the $131 Billion parking industry evolved to be so complicated and outdated Why dynamic pricing in parking is harder than hotels and airlines The three primary business models for a parking lot Why Air Garage can increase a parking lots profitability by 4-5x How part of its business was inspired by scooter companies like Bird and Lime Starting “Airbnb for Driveways” in 2016 to solve their own problem as college students The sales lessons Jonathon learned doing door-to-door sales in the Arizona heat How getting scammed out of $6,000 led to pivoting their business model Moving to San Francisco with no connections and raising a Seed round How they closed a Series A in a week The importance of investor brand when hiring early employees Why Jonathon cares so much about branding as a parking company—Referenced: https://www.airgarage.com/ https://parkingreform.org/resources/parking-lot-map/ Mac vs PC ads: https://www.youtube.com/watch?v=0eEG5LVXdKo Never Split the Difference: https://www.amazon.com/Never-Split-Difference-Negotiating-Depended/dp/0062407805 https://en.wikipedia.org/wiki/Detroit https://en.wikipedia.org/wiki/List_of_recessions_in_the_United_States—Where to find Jonathon: Twitter: https://twitter.com/jonathonbarkl LinkedIn: https://www.linkedin.com/in/jonathonbarkl—Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc—Production and distribution by: https://www.supermix.io—Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Dan Lorenc is the Co-founder and CEO of Chainguard, the best way to secure your open source software. Dan and his co-founders Kim, Matt, and Ville started the company in 2021 after spending a decade working together at Google on all things open source and software security. They’ve since raised $116 million from investors including Spark (led Series B), Sequoia (led Series A), Amplify (led Seed), The Chainsmoker’s Mantis VC, Banana Capital, and dozens of angels in the cyber security and open source communities. — Topics discussed: What is the “software supply chain”? How the SolarWinds breach created the software supply chain security market The history of open source software Why open source software makes software supply chains even less secure The moment Dan and his co-founders decided to start Chainguard Why they started selling consulting services before even building a product The reason their first two products solved completely different problems (top-down and bottoms-up), and why the one that didn’t work at first is now their main business Why Chainguard decided to focus on a broad communications and marketing strategy so early on How Dan gets quoted in major media publications as an early stage startup founder Why Chainguard uses memes for marketing Why Dan thinks startups should “make content optimized for the group chat” How they raised their Seed round from Amplify a week after leaving Google Raising a Series A from Sequoia as the market started collapsing in Spring of 2022 Dan’s advice for founders on dealing with investor inbound when not fundraising Why he wish he hired sales reps sooner Raising a Series B from Spark Capital to accelerate their enterprise sales process — Referenced: https://www.chainguard.dev https://www.sigstore.dev/ Battling the Trojan Horse in Open Source: https://www.sequoiacap.com/article/dan-lorenc-chainguard-spotlight/ Chainguard Series B Announcement: https://www.chainguard.dev/unchained/series-b-funding Dan’s favorite open source project: https://github.com/jqlang/jq Reflections on Trusting Trust: https://www.cs.cmu.edu/~rdriley/487/papers/Thompson_1984_ReflectionsonTrustingTrust.pdf — Where to find Dan: Twitter: https://twitter.com/lorenc_dan LinkedIn: https://www.linkedin.com/in/danlorenc — Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io — Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Nichole Wischoff is the founder of Wischoff Ventures, a Pre-Seed and Seed firm that invests up to $1 million in non sexy industries. Nichole closed her first fund in 2021, and previously was an early employee at Blend (NYSE:BLND), One (acquired by Walmart in 2022), and Built. — Brought to you by Secureframe, the automated compliance platform built by compliance experts. Sign-up here: https://bit.ly/3Sif1PH — Topics discussed include: • Growing up on food stamps in Arkansas • How studying abroad in Belgium changed Nichole’s life • How falling in love with running got her into college and her first job • Why Taylor Swift could be the first female President • Opening a bakery to pay rent while teaching English in Spain • Getting her first job at Citi’s non-profit housing financing team • Leveraging that experience to get a job in fintech • Making her first angel investment in Vesta • How Nichole got One Financial its first 25k users • Helping sell One Financial to Walmart • How Lee Fixel and Chad Byers helped raise her first $5m fund • Lessons learned going from a $5m to $20m fund in 2022 • Nichole’s advice for anyone raising their first fund • Behind the scenes of her viral “Third Tier VC” moment — Referenced: •Taylor Swift (Acquired’s Version): https://www.acquired.fm/episodes/taylor-swift-acquireds-version • Nichole’s $20m Fund Announcement https://techcrunch.com/2022/12/16/solo-gp-nichole-wischoff-raises-20m-fund-backed-by-peter-thiel-to-invest-in-unsexy-businesses/ • J Cal’s “3rd or 4th Investor in Uber” Montage: https://www.youtube.com/watch?v=OK4Mku_s4H4 — Where to find Nichole: • Twitter: https://twitter.com/NWischoff • LinkedIn: https://www.linkedin.com/in/nicholewischoff • Wischoff Ventures: https://www.wischoff.com/ — Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak • Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io — Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Waseem Daher is the Co-founder and CEO of Pilot, the bookkeeping, CFO, and tax provider for startups and fast growing businesses. Prior to Pilot, Waseem and his co-founders Jeff and Jessica sold companies to Oracle and Dropbox. — Waseem, Jeff, and Jessica started Pilot in 2017, and have since raised over $160 million from investors like Index Ventures, Stripe, Sequoia, Whale Rock, Jeff Bezos, and over 40+ angel investors. — Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3FoYm52 — In this episode, we discuss:• Why Waseem’s building a startup that does your accounting• The reason he first started doing his own bookkeeping, and why he doesn’t recommend it to other founders• When startups should build something themselves and when to outsource• All the mistakes Waseem made building and selling his first two startups to Oracle and Dropbox• How to avoid “fake work”• How to get ROI from conferences• His disastrous first ever meeting with a VC• Why the best fundraising advice is to build a business that doesn’t need to raise money• “Companies are bought, not sold” and his framework for startup M&A• Why it’s a mistake to build your startup just to be acquired• Why consensus startup ideas rarely work, and the best startups need some secret or structural change that no one else has noticed yet• Why tech-enabled service businesses are so hard to scale• How Pilot got its first customers• Pilot’s unique approach to raising its Seed round• The initial scare when raising their Series A• Why its Series B was half of what they could have raised —Where to find Waseem: • Twitter: https://twitter.com/waseem • LinkedIn: https://www.linkedin.com/in/wdaher • Newsletter: https://waseem.substack.com/ — Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak — Production and distribution by: https://www.supermix.io — For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Vlad Magdalin is the Co-founder and CEO of Webflow, software that empowers designers to build websites without code. Vlad started the company with his co-founders Sergie Magdalin and Bryant Chou in 2013, and has since raised roughly $335 million supported by investors like Accel, Khosla Ventures, YCombinator, Capital G, and Eric Bahn. — — — — Brought to you by Mercury, the bank built for startups. Join more than 100,000 startups and venture capital firms on Mercury, the powerful and intuitive way for ambitious companies to bank.Sign-up now: https://bit.ly/46ImCuD Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC. — — — — Topics discussed include: • The history of web browsers, websites, and web design • Why websites are the ultimate economic enablers • How Webflow empowers anyone to design websites without code • Why website design is a gateway into programming • How the movement to CSS and web standards in the 2000’s and 2010’s created the opportunity for Webflow to build a product around responsive design • Moving to the US with his parents and five siblings as refugees from the USSR at nine years old • How losing half of their luggage and immigration documents in the move enabled his dad to buy the family’s first computer • The first website Vlad ever designed for a Brad Pitt movie • How his experience dropping out of a computer science degree to work in 3D animation at Pixar, then going back to school gave him the idea for Webflow • Failing to build Webflow three times between 2005 and 2008 • Why the spouses and partners of founders are the unsung heroes of startups • The moment he immediately quit his job and attempted Webflow for the fourth time • Burning three months of runway on a Kickstarter that never went live • Liquidating his retirement account, paying rent with credit cards, and selling and leasing back the family car’s to keep the business running • Vlad’s exuberant optimism that kept him going for 10 years • Failing to get into YC, and the crazy story behind getting accepted the second time • The trajectory-altering customer and fundraising advice they got from Paul Graham • The “Investing on Principle” contract they signed with Accel who led Webflow’s Series A • Why Vlad thinks every startup founder should operate with the assumption they’ll never be able to raise money again Referenced: • Inventing on Principle (Video): https://www.youtube.com/watch?v=PUv66718DII • Inventing on Principle (Transcript): https://jamesclear.com/great-speeches/inventing-on-principle-by-bret-victor • The Infinite Game: https://simonsinek.com/books/the-infinite-game/ Where to find Vlad: • Twitter: https://twitter.com/callmevlad • LinkedIn: https://www.linkedin.com/in/vladmagdalin Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Keith is the Co-founder and CEO of OpenStore, a portfolio of brands building its own shopping destination. Before starting OpenStore, Keith was an early executive at companies like PayPal, eBay, LinkedIn, and Square, a co-founder of OpenDoor, and an early investor in companies like DoorDash, Faire, Affirm, Webflow, Ramp, and Stripe, and is also currently a General Partner at Founders Fund Keith started the company in 2021 with co-founders Jack Abraham, Matt Lanter, and Jeremy Wood, and has since raised over $150 million supported by investors like Atomic, Founders Fund, General Catalyst, Khosla Ventures, Lux Capital, and Vine Ventures. — Brought to you by Packsmith, better fulfillment for growing brands. Sign-up here https://bit.ly/PacksmithBanana — In this episode, we discuss: • The 3-minute conversation that started OpenStore • All the problems that still exist in ecommerce • Why Instagram Shopping failed • What Keith and team are building at OpenStore • Why Wish failed • The margin profile of most consumer brands • A crash course on contribution margin and profitability for startup founders • How OpenStore gets 3x higher contribution margin than other consumer brands • As a VC, the one thing Keith looks for in the founders he backs • A framework for founders and investors to consider when incubating companies • Why Keith thinks no great SF-based startups has been founded since March of 2020 • The reasons he moved to Miami • Why he’s bearish on most AI startups • His favorite interview questions for candidates Referenced: • Email Keith - keith@foundersfund.com Where to find Keith: • Twitter: https://twitter.com/rabois • LinkedIn: https://www.linkedin.com/in/keith Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Natasha Vernier is the Co-founder and CEO of Cable, the all-in-one effectiveness testing platform for financial services. Prior to Cable, Natasha joined UK neobank Monzo when it had less than 100 customers. She built and led their financial crime team for five years, and is one of the most knowledgeable individuals in the world on financial crime, which amounts to over $4 trillion per year, or 4% of global GDP. Natasha started Cable in 2020 with her co-founder Katie Savitz, and has since raised over $16 million supported by investors like LocalGlobe, CRV, Stage 2, and Jump Capital. — Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3ZyBhWM — Topics discussed: • How crime is a $4 trillion market • Why 80% of crime is carried out for financial gains • Why the UN estimates we only catch 0.2% of financial crime • The reason banks are incentivized to stop fraud, but not crime • Why it's so hard to stop financial crimes • How $20B in financial crime was committed on crypto rails in 2022 • What “Synthetic ID Fraud” is, and why it's the fastest growing type of fraud in the US • What Natasha thinks are the new frontiers of fraud • Joining Monzo as one of the first employees and staying through a $4B valuation • What it’s like to be fully invested in a startup when you’re not a founder • Building Cable to enable regulatory and financial crime teams • Raising a Pre-Seed round and signing the first customer without a product built • Why compliance officers want to buy complicated products • How Natasha diversified her cap table, raising a Seed round from CRV and a group of angels with broad skill sets, ethnicity, race, and sexuality • How she got two funds to pre-empt her Series A • Why founding a startup means getting punched in the face every day, and her biggest mistake is not enjoying the little things sooner • The two founders she most looks up to • The one interview question she asks every candidate at Cable Referenced: • Cable’s site: https://cable.tech • Cable’s Seed round: https://community.cable.tech/weve-raised-5-3m-from-crv-localglobe-and-a-diverse-group-of-exceptional-angels/ • How They Built the Hoover Dam (Part 1): https://www.youtube.com/watch?v=rXFjLaUxpaw • How Vegas Became VEGAS (Part 2): https://www.youtube.com/watch?v=3QNuYHEzS2o Where to find Natasha: • Twitter: https://twitter.com/natashavernier • LinkedIn: https://www.linkedin.com/in/natashavernier Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Alex Bouaziz is the Co-founder and CEO of Deel, a full stack global HR and payroll platform. But the company didn’t start that way, and we’ll talk through Alex and his co-founder Shuo’s journey from zero to one, starting with a product that helped startups hire international employees. Alex and Shuo launched the company one week before YC Demo day in 2019, and have since scaled to 20,000+ customers and raised over $685 million. They’re supported by investors like YC, a16z, Spark Capital, Weekend Fund, Coatue, SV Angel, Soma Capital, Quiet Capital, and angels like Lachy Groom, Nat Friedman, Ryan Petersen, Alexis Ohanian, John Zimmer, Dara Khosrowshahi, Rex Salisbury, Justin Mateen, and more. — In this episode, we discuss: • The initial insight around remote work that started Deel in 2019 • How they initially built the wrong solution • Pivoting one week before YC demo day • Listening to customers to build a better product • Growing 20% every month for a year • Being a default optimist • Dealing with the emotional ups and downs of building a startup • Moving at “Deel Speed”, and how the team operates so fast • Deel’s remote-first approach and its “WeWork Squads” • His advice to other leaders building remote teams • Why founders shouldn’t share too much information with early investors • How Alex’s approach to fundraising changed through his Seed to Series D rounds • Why founders should always be selling their product • How picking board members is a form of marriage, and what founders should prioritize when picking them • Why Deel raised a Series A and B in a three month span despite only burning $300k since closing its Seed round • How deep pocketed investors unlock optionality as a company scales • The benefits to taking on lots of angel investors • How Deel prioritized international expansion as it grew • Deel’s new Visa / immigration and HR AI products • Two things Alex would do differently if he could start over • The founders he most looks up to — Read the transcript: https://www.thespl.it/p/growing-deel-to-300m-arr-in-four Where to find Alex:Twitter: https://twitter.com/BouazizalexLinkedIn: https://www.linkedin.com/in/alexbouaziz/ Where to find Turner:Newsletter: https://www.thespl.itTwitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Semil Shah is the Founder of Haystack, an institutional venture capital firm that backs outlier founders at the earliest stages. Semil started Haystack in 2013, and has since invested in X unicorns like DoorDash, Instacart, Figma, HashiCorp, Ironclad, Carta, Applied Intuition, and Opendoor.This episode takes us behind the scenes of Semil’s two decade journey building Haystack from scratch. We’ll dive into how he raised and deployed each of the first six Haystack funds, including all the mistakes made along the way, plus the details around Haystack’s new $75 million and $25 million funds announced the date this episode was published.Read Haystack's announcement here: https://semilshah.com/2023/09/10/announcing-haystack-vii-same-model-fresh-funds-and-new-era/—Brought to you by Mercury, the bank built for startups. Join more than 100,000 startups and venture capital firms on Mercury, the powerful and intuitive way for ambitious companies to bank.Sign-up now: https://bit.ly/3sQRzOwListen to my conversation with Immad, the Co-founder and CEO of Mercury:Spotify: https://open.spotify.com/episode/24ujuXZ2uws48bvwOh9NcRApple: https://podcasts.apple.com/us/podcast/lessons-from-building-mercury-with-immad-akhund-co/id1694440669?i=1000619360042 Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC. —Topics discussed include:Juggling multiple jobs while living paycheck to paycheck his first eight years in Silicon Valley Failing to get his first job in venture three timesInvesting in the Seed rounds of unicorns DoorDash, Instacart, Hashicorp, and Envoy within the first six months of starting Haystack Why he initially thought Haystack would be a short-term thingTurning down multiple lucrative job offers two years inHow the best LPs evaluate VC funds on the “Entry Ownership to Fund Size” ratio Semil’s strategy of “crawl, walk, run” to increase Haystack’s check sizes over time The pain he felt failing to hit his target fund size on the first four fundraises and how he handled it Why everyone should “pre-market” a fundraise, and how to do itThe things most founders don’t appreciate about raising a venture fund Fighting to invest in Ironclad’s Seed round before he had his next fund raised How LPs reference VCs, and how a VC can become referenceableWhy Haystack Fund IV was the scariest fund to raiseHow Semil builds relationships with LPsThe hardest questions he faced raising each fund and what other VCs should anticipate while raising their own fund How LP investment committees make decisionsWhat’s going on behind the scenes at most large venture LPs todayWhy the traditional advice of “finding an anchor LP” makes no senseSpilling his secret on the best quarter to fundraiseWhy VCs should fundraise with a hard cap on fund sizeWhy every VC should appreciate and remember how LPs supported them through the pandemic All the details on Haystack’s new $75 million and $25 million fundsSemil’s plan for the next 10 yearsThree pieces of advice for emerging fund managersWhere to find Semil:Twitter: https://twitter.com/semilLinkedIn: https://www.linkedin.com/in/semilshah/Where to find Turner:Newsletter: https://www.thespl.itTwitter: https://twitter.com/TurnerNovakProduction and distribution by: https://www.supermix.io/For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Sean Frank is the CEO of Ridge Wallet, a men’s wallet and accessories brand that does over 9-figures in annual revenue. The company started in 2012 and raised $266,000 in a Kickstarter campaign to sell the first 5,200 wallets. Ridge hasn’t raised a single dollar of outside capital since, and has also expanded into new categories like rings, knives, watches, backpacks, and keys, with dozens of more products coming soon. Sean is known in some circles as the “Einstein of Ecommerce”, and he gives us an inside look at running a consumer brand in 2023. Brought to you by Packsmith, better fulfillment for growing brands: https://bit.ly/PacksmithBanana In this episode, we discuss: Why wallets are a terrible product category How Ridge has 80% gross margins Why brands should generally not raise venture capital When a founder should step down as CEO, and how to hire a new one Why Ridge is one of the top 10 advertisers on Twitter When and how to hire a marketing agency Why Ridge never raised outside capital Closing clients in a 1991 Honda Civic A crash course on the men’s and women’s fashion markets Why Sean thinks women’s fashion will have 50% return rates this holiday season Investing in a watch manufacturer and building a factory in Arizona to vertically integrate Why every company needs a core competency The simple tech stack Ridge uses to run their business Why Crocs is a great business Sponsoring 5,000+ influencers Why Amazon shut down its private label program and every brand should sell on it Why influencer marketing performs so well, and how to start and scale an influencer marketing program Why more companies should incorporate creators in their content How FTX and other crypto companies inflated influencer marketing prices Paying $1,000,000 to hire a creator in-house How the Ridge Wallet has saved customers from a bullet and a chainsaw Where to find Sean:Twitter: https://twitter.com/SeanEcomSubstack: http://seanecom.substack.com/Podcast: https://9operators.com/ Where to find Turner:Newsletter: https://www.thespl.itTwitter: https://twitter.com/TurnerNovak Referenced:https://www.amazon.com/Great-CEO-Within-Tactical-Building-ebook/dp/B07ZLGQZYChttps://www.theloganbartlettshow.com/https://www.maryruthorganics.com/ Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Dimitri Dadiomov is the Co-founder and CEO of Modern Treasury, an operating system for the new era of payments. Dimitri and his co-founders Matt and Sam started the company in 2018 after running into the same problem working together at their previous startup. Modern Treasury has since raised over $183 million, supported by investors like YCombinator, Benchmark, Altimeter, Salesforce Ventures, Quiet Capital, WndrCo, TQ Ventures, and Edward Lando. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGC Sign-up for Ramp and get $500: https://bit.ly/3KSqfFV Read the transcript: https://www.thespl.it/p/how-to-move-quadrillions-of-dollars In this episode, we discuss: How the global banking system moves over $1 quadrillion per year Why B2B products should be easy to use with broad use cases What makes a good API business Why the YC application is a great forcing function for founders How it took them six months to get their first customer, but never pivoted Why the first customers of a B2B business should get more credit How PLG helped build a better product Finding holes in the market for an initial go-to-market strategy The depth of Modern Treasury’s product Why they should have built a sales team sooner How deep customer relationships across many industries helped them raise a Series A Why it’s important to go slow to go fast How Dimitri set an intentional culture around studying other businesses When distribution can be more important than product What happened inside Modern Treasury during the collapse of SVB and Signature Bank Why Dimitri sends Saturday update emails to entire company The founders Dimitri really admires Where to find Dimitri: Twitter: https://twitter.com/dadiomov LinkedIn: https://www.linkedin.com/in/dadiomov/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Read the transcript: https://www.thespl.it/p/how-to-move-quadrillions-of-dollars Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Kendall Baker currently leads Yahoo’s sports newsletter business. In 2017 he launched the first daily sports newsletter called Sports Internet, which he sold to Axios in 2019. Before Sports Internet, he convinced the founders of The Hustle to focus their online tech blog on a daily newsletter, which he wrote for a year and a half. And before The Hustle, he produced SportsCenter at ESPN. He’s spent nearly a decade at the intersection of daily news and sports, and this episode is packed with insights on both. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGC Read the transcript: https://www.thespl.it/p/the-business-of-newsletters In this episode, we discuss: The history of the newsletter industry Why the best writers delete more than they write How he got on ESPN SportsCenter A crash course on the sports media business How to write a daily newsletter The importance of experimenting How he got his first dollar of revenue Why Kendall spent $0 on growth Selling his “Sports Internet” newsletter to Axios Why Adam Silver, commissioner of the NBA, reads Kendall’s writing Why Yahoo’s the next rocketship The surging momentum in US soccer And the most underrated athletes (current and all-time) Listen on other platforms: Apple: https://podcasts.apple.com/us/podcast/the-business-of-newsletters-kendall-baker/id1694440669?i=1000624033211 YouTube: https://youtu.be/4es4p7sFMf0 Where to find Kendall: Twitter https://twitter.com/kendallbaker Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Read the transcript: https://www.thespl.it/p/the-business-of-newsletters Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Dan Porter is the Co-founder and CEO of Overtime, a sports network for the next generation of fans. OT reaches 85 million fans per month and runs a basketball league (Overtime Elite, OTE), a flag football league (OT7), and is launching a boxing league (OTX) the week this episode airs. Dan started Overtime with his co-founder Zack Weiner in 2016, and has since raised over $215 million. OT is supported by investors like the late ex-NBA Commissioner David Stern, Jeff Bezos, Drake, Carmelo Anthony, Trae Young, over 25 other NBA players, Spark Capital, Redpoint, a16z, Greycroft, Afore Capital, and Banana Capital. [Turner Novak and Banana Capital are investors in Overtime]. Brought to you by Secureframe, the automated compliance platform built by compliance experts: ⁠http://bit.ly/3Qk4RNd In this episode, we discuss: The business of sports Why people love sports The founding story of Overtime How to raise money for a unique idea Overtime’s very first product How to bet on technological change The changing professional sports landscape How to launch a sports league Why founders must obsess over their product Read the transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans Where to find Dan: Twitter: ⁠https://twitter.com/tfadp⁠ LinkedIn: ⁠https://www.linkedin.com/in/danporter/⁠ Where to find Turner: Newsletter: ⁠https://www.thespl.it⁠ Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/TurnerNovak⁠ Where to find The Peel: YouTube: ⁠https://www.youtube.com/@ThePeelPod⁠ Instagram: ⁠https://www.instagram.com/ThePeelPod⁠ TikTok: ⁠https://www.tiktok.com/@ThePeelPodcast⁠ Read the full transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans Production and distribution by: ⁠https://www.supermix.io⁠ For sponsorship inquiries: ⁠https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform⁠

Nick Saltarelli is the Co-founder of Mid-Day Squares, a healthy, functional chocolate bar. Nick, his wife Lezlie, and her brother Jake started the company in 2018 from their kitchen in Montreal, and have since built their own factory with $70 million in capacity, and grown the company to a $26 million revenue run rate. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/building-a-70-million-chocolate-factory In this episode, we discuss: The history of the $200 billion chocolate market Competing against 100+ year-old monopolies Finding a huge opportunity in healthier chocolate The dirty secrets of contract manufacturing Why no one knows how to make a Snickers bar, and Coca-Cola doesn't have a patent How to build a moat in CPG Why Mid-Day Squares had to build their own factory Making chocolate like Tesla makes cars Copying Facebook’s launch strategy Measuring product market fit in CPG Almost running out of money during COVID Why every founding team should go to therapy Surviving an 85% drop in revenue How to raise a bridge round Building an enduring brand Why marketers should study the music industry Timestamps [00:00:00] Intro [00:03:07] The insane politics of chocolate [00:04:53] The history of chocolate [00:07:11] The enormous market for chocolate [00:10:24] The nutrition of chocolate [00:15:00] The Mid-Day Squares origin story [00:20:05] Creating the first product [00:25:53] Why Coca-Cola never filed a patent on their formula [00:29:08] Why they built their own manufacturing plant [00:31:35] A crazy and creative fundraising strategy [00:39:26] Taking over an island and finding PMF [00:46:32] Raising $2m to prove 2 things [00:47:15] Automating production and navigating manufacturing chaos [00:51:11] Why he had to "plead with the government on public TV” [00:53:51] On "eating shit sandwiches” [00:57:30] The COVID mistake that dropped revenue by 85% [01:03:02] Advice for raising a bridge round [01:04:55] How to build fans not customers [01:07:12] How to build in public [01:12:23] Rapid fire questions Where to find Nick Twitter: https://twitter.com/nickywonka Where to find Turner LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/ Twitter: https://twitter.com/TurnerNovak Where to follow The Peel podcast YouTube: https://www.youtube.com/@ThePeelPod Instagram: https://www.instagram.com/ThePeelPod TikTok: https://www.tiktok.com/@ThePeelPodcast Read the transcript: https://www.thespl.it/p/building-a-70-million-chocolate-factory Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Ilir Sela is the Founder & CEO of Slice, the online ordering and all-in-one software platform that helps pizzeria’s manage their business. Ilir started the company in 2010 as MyPizza, rebranded to Slice in 2015, and has since raised over $125 million and supports over 20,000 independent pizza shops. Slice is supported by investors like GGV, KKR, 01 Advisors, Primary Ventures, FJ Labs, and RiverPark Ventures. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/arming-the-pizza-rebels-ilir-sela In this episode we cover - The three reasons small pizza shops are growing 24x faster than big chains - How franchising and "reverse franchising" works - Ilir's biggest mistakes building a franchise business before starting Slice - How to explain a new business model to investors - The customer acquisition benefits of a multi-product model - Bootstrapping Slice to $3 million in profit - Turning down two acquisition offers, one that would have made him nine figures personally - Why MrBeast Burger failed - Why we don't need more cloud kitchens - Empowering entrepreneurs to open their own pizza shops - Building a strong board - Advice for founders selling to small businesses Referenced Cloud Kitchens: ⁠https://www.thefoodcorridor.com/blog/everything-you-need-to-know-about-cloud-kitchens-ghost-kitchens/ Frank Slootman from Snowflake, who Illir said inspires him: ⁠https://www.linkedin.com/in/frankslootman/ Growth in independent pizzerias vs big chains in 2022: ⁠https://www.pmq.com/pizza-power-report-2023/ Jeff Richards from GGV Capital, who invested in Slice and gave Illir some advice mentioned in the podcast: ⁠https://www.linkedin.com/in/jeffrichards/ Michelle Obama on whether pizza is a vegetable: ⁠https://www.youtube.com/watch?v=G14qNHPE4qo&t=21s ⁠ MrBeast’s MrBeast Burger: ⁠https://www.mrbeastburger.com/ The growth of Domino’s stock since 2010: ⁠https://www.cnbc.com/2020/02/25/dominos-stock-yields-higher-returns-than-google-since-ipos.html Slice’s website: ⁠https://slicelife.com/ Where to find Turner Newsletter: https://www.thespl.it/ Twitter: https://twitter.com/TurnerNovak Where to find Ilir: LinkedIn: https://www.linkedin.com/in/ilirsela Twitter: https://twitter.com/ilirsela Timestamps [00:03:34]: The enormous and fascinating pizza industry [00:04:30]: Why there are so many independent pizza shops [00:07:33]: Illir's deep family history with pizza [00:10:43]: What Slice provides independent pizzerias [00:14:21]: The origins of Slice (mypizza.com) [00:16:55]: Building "Nerd Force" before Slice [00:18:22]: How franchises like “Nerd Force” work [00:22:15]: Selling his first company: Nerd Force [00:23:46]: Forming the idea for Slice [00:27:19]: The very first customers [00:32:37]: Turning down $18 million to double down on Slice [00:33:41]: Raising money and starting Slice phase 2.0 [00:39:27]: An acquisition offer that was “tough to say no to” [00:41:55]: Slice's focus now and in the near future [00:45:01]: Why there are so many pizza shops [00:46:46]: Hot takes on Cloud Kitchen and Beast Burgers [00:51:55]: Why online customers are worth 4x more than offline ones [00:53:32]: Why some investors doubted Slice [00:57:58]: The underrated value of a good board [01:00:57]: Advice for founders serving small businesses [01:03:29]: Hitting $500m annual revenue with Slice 3.0 [01:04:31]: Other categories Slice could go after [01:06:25]: Rapid fire questions Read the transcript: https://www.thespl.it/p/arming-the-pizza-rebels-ilir-sela Production and distribution by: https://supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Adrian Aoun is the Founder and CEO of Forward Health, which is rebuilding healthcare as a product, not a service. Forward is supported by investors like Founders Fund, Khosla Ventures, Softbank, Expa, Marc Beinoff, Ashton Kutcher, The Weeknd, Lee Linden, Josh Kushner, First Round Capital, Eric Schmidt, DCVC, and more, Before starting Forward, Adrian worked with Larry Page at Google to setup and launch new companies inside of Alphabet. He joined Google through the acquisition of his AI startup Wavii, and spent his first year at Google helping create and build its AI division. Adrian was on the President's Council of Advisors on Science and Technology, and is an angel investor in companies including Stripe, Uber, Anduril, and more. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit In this episode, we discuss: Rad the transcript: https://www.thespl.it/p/making-healthcare-a-product-not-a - How the healthcare industry actually works - Why poor incentives make technology in the industry ROI-negative - The founding story of Forward - Why healthcare should be a product, not a service - Building doctor's offices like Tesla builds cars - Being Larry Page’s right hand man at Google - Building a “healthcare operating system” like Apple builds the app store - Adrian’s contrarian views on the food industry - Why animal farming is a bigger climate issue than you might think - Zuck: the man in the arena Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Where to find Adrian: Twitter: https://twitter.com/adrianaoun LinkedIn: https://www.linkedin.com/in/adrianaoun Read the transcript: https://www.thespl.it/p/making-healthcare-a-product-not-a Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Immad Akhund is the Co-founder and CEO of Mercury, a digitally native bank for startups. Mercury is supported by investors like a16z, Coatue, CRV, Chapter One, Ryan Peterson, Scott Belsky, Serena Williams, Terrence Rohan, Zach Coelius, Todd Goldberg, and more. Before Mercury, Immad was a part-time partner at YC, co-founded Heyzap which sold for $45 million, and co-founded and scaled Clickpass to millions of users. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/the-future-of-banking-remote-work In this episode, we discuss: - The future of banking - Why Mercury’s beautiful onboarding was an accident - Cultural mistakes most startups make - Two lessons from selling his first company for $45 million - How to get free legal advice - Why it’s better to build a network of entrepreneurs than investors - How to fundraise - Why its contrarian to start a non-AI company right now - How Mercury is thinking about AI - Why each operational team has its own engineering team - The embarrassing pitch meeting that raised his Series A from a16z - How crypto used up all its goodwill - The hiring advice he gives every founder Where to find Immad: Twitter: https://twitter.com/immad LinkedIn: https://www.linkedin.com/in/iakhund Podcast: https://curiositypodcast.substack.com/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Mentioned in this episode: Mercury https://www.mercury.com The Logan Bartlett Show: https://www.youtube.com/watch?v=QcL_cjZDeFU Timestamps: (0:00) Intro (5:58) Mercury's "accidentally great" onboarding experience (8:13) The fundamental banking business model (9:34) The basics of banking regulation (11:07) How Mercury works with banks (13:27) The future of banking (19:34) Immad's previous startups (22:30) What culture actually means (27:06) Importance of ideas vs execution (32:03) Learning banking from scratch (35:54) Why the first banking partnership failed (37:56) Why the second banking partnership worked (39:24) The difference between compliance and risk teams (42:08) Why compliance is so relevant for better banking (50:13) The biggest mistake for doing remote work (51:21) Mercury Raise (53:33) The game theory of fundraising (54:54) Playbook for generating fundraising momentum (60:45) Common fundraising mistakes (63:12) Hilarious fundraising mishap in front of a16z (68:16) Companies that aren't like this shouldn't touch AI (70:57) Who will win big from AI? (72:10) Immad's take on crypto (86:14) Outro Read the transcript: https://www.thespl.it/p/the-future-of-banking-remote-work Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Ryan Delk is the Co-Founder and CEO of Primer, a startup helping ambitious kids unlock their potential by empowering teachers to launch and run their own micro-schools. Primer’s supported by investors like Founders Fund, Khosla Ventures, Village Global, Susa Ventures, Sam Altman, Naval, Ryan Peterson, Amjad Masad, Julie Zhuo, Tobias Lutke, Lachy Groom, Howie Liu, Dylan Field, Packy McCormick, and many more. Before Primer, Ryan was the COO at peer-to-peer rental marketplace Omni (sold to Coinbase), and prior to that led Growth and Partnerships at Gumroad from $10,000 to $50 million in GMV. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/turning-techers-into-superheroes In this episode, we discuss: - How the $1 trillion US K-12 education system works - The broken incentive structures in education - Why teachers are superheroes - How to double a teacher’s income - Primer’s origin story - How to open a school - If online school works - Why founders make the best employees - How the US government wastes billions of dollars - Why everyone should care more about local politics Where to find Ryan: Twitter https://twitter.com/delk LinkedIn: https://www.linkedin.com/in/delk/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Timestamps: (3:42) The state of K-12 education in the US (6:35) The structural problem causing a radical misallocation of resources (8:00) The importance of teachers (9:34) The “totally flipped” incentive structure for teachers  (12:22) The problem of bureaucracy in education  (13:38) Primer’s thesis (14:52) How to start a school (16:00) How Primer helps teachers start their own schools (18:20) Using underutilized real estate to host micro-schools (20:05) Ryan’s take on digital vs in-person learning (21:59) How Primer supports teachers (23:21) Inspirational stories from Primer users (28:00) The underestimated entrepreneurship of teachers  (29:12) How Primer stays affordable for all users  (30:26) How Primer gets teachers on board  (32:04) The role of after-school activities  (33:07) How Primer sets its Curriculum (35:14) Ryan’s unique education and how it inspired Primer  (38:39) Why someone hadn’t solved this problem yet (40:24) Primer’s initial strategy (41:30) The breakfast that changed everything (42:09) The concept of “Barrels” from Keith Rabois (42:36) Finding and recruiting Ian Bravo (43:31) How Primer recruits ex-founders (44:52) The 3 things Primer screens for in teachers (46:27) What Primer messed up when launching (48:19) Re-thinking school admissions from first principles (51:03) How they convinced the very first teachers to try Primer (51:59) The ineffective usage of education spending (53:28) Policymakers prioritizing “signal over outcomes” (57:21) The worst public schools are worse than you think  (59:08) How the Government wastes billions of dollars and Ryan’s idea for solving this (61:31) The importance of increasing engagement with local politics (63:37) The vision for Primer Read the transcript: https://www.thespl.it/p/turning-techers-into-superheroes Production and distribution by: https://www.supermix.io/ For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Ken Ehrman is the co-founder and Managing Partner of Halo Collar, a smart dog collar that tracks your dog with GPS. Halo Collar uses patented technology that allows customers to instantly create up to 20 unique virtual dog fences from their phone using GPS. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/the-iphone-for-your-dog-ken-ehrman In this episode, we discuss: - Working for Mike Markkula, the first investor in Apple - Building hardware and the importance of patents - Listening to customers, solving their problems, and sizing a market - Qualifying enterprise customers and selling with "calm confidence." - Early investors trying to buy 95% of his first company - Getting the US Post Office and Army to fund $15 million in R&D - Taking a company public in 1999 with $3 million in revenue - Using AI to train dog movements and make "the Apple Watch" for dogs - The crazy story of how he met his celebrity co-founder, Cesar Millan the Dog Whisperer - What happened when they met famous TikToker Charli D'Amelio Where to find Ken: LinkedIn: https://www.linkedin.com/in/ken-ehrman Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Referenced: Buy the Halo Collar: https://www.halocollar.com/ Cesar Millan, 'the Dog Whisperer': https://www.cesarsway.com/ More on RFID tags: https://www.youtube.com/watch?v=Ukfpq71BoMo&ab_channel=ALLABOUTELECTRONICS Read the transcript: https://www.thespl.it/p/the-iphone-for-your-dog-ken-ehrman Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Jonathan Neman is Co-Founder & CEO of Sweetgreen, an American fast casual restaurant chain that serves salads. Jonathan and his co-founders started the company in 2007, opening their first restaurant just three months out of college. Sweetgreen opened its second and third locations in the middle of the 2008 Global Financial Crisis, and went public in 2021 in the middle of the COVID-19 pandemic. Sweetgreen’s focus on locally sourced quality ingredients has built it into a national brand with more than 200 restaurants across the US. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/the-peel-episode-1-building-mcdonalds In this episode, we discuss: - How the restaurant industry actually works - How the US food system leads to over $2 trillion in indirect healthcare and environmental costs - Sweetgreen’s origin story - The early constraints that led to Sweetgreen’s ingenious business model - Launching a music festival headlined by Kendrick Lamar, The Weeknd, and The Strokes - Killing a major product line to double down on online ordering in 2015 - How to build an enduring brand - Sweetgreen’s new salad subscription and gamified loyalty program - The surprising benefits of Sweetgreen’s new automated Infinite Kitchen - How the best entrepreneurs never give up Where to find Jonathan: Twitter https://twitter.com/jonnynemo LinkedIn: https://www.linkedin.com/in/jonathan-neman-9a28aa8/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Timestamps: (2:35) The state of the restaurant industry since 2007 (6:03) How COVID-19 changed the restaurant industry (9:05) The bad incentives holding back the US health system (10:58) How Sweetgreen built a local AND national brand (13:07) How he made $40,000 a year in high school (15:30) How a stint in Australia inspired Sweetgreen (17:45) Sweetgreen’s 50-person friends & family round (20:14) Challenges of opening the first restaurant (21:58) How a tiny 500-square-foot restaurant unlocked Sweetgreen's success (22:50) When sales suddenly dropped 70% (23:40) The moment he realized he wanted to start his own business (26:23) Opening early restaurants during the Global Financial Crisis (27:35) Using a farmer's market to start a music festival and promote Sweetgreen (29:49) Landing Kendrick Lamar, The Weeknd and The Strokes as festival headliners (32:41) Why they shut down their second-largest product line (35:16) Launching Sweetpass (a gamified loyalty program) (38:19) Launching Infinite Kitchen (a fully automated restaurant) (42:05) Online ordering trends (44:13) The challenge with customizable food (45:36) Using automation to reduce preparation error rates (46:50) Acquiring a startup built by MIT grad students (49:04) The surprising benefits of Infinite Kitchen (52:25) The key to making healthy food accessible (53:30) Unfortunate facts of the US food system (57:25) How to “do the right thing” AND maximize profits (59:58) His favorite board game is... (60:52) We need to stop glamorizing overnight success Read the full transcript: https://www.thespl.it/p/the-peel-episode-1-building-mcdonalds Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform