Are Your Business Expenses Audit-Ready? With Shoeboxed Owner Doug Breaker
Are Your Business Expenses Audit-Ready? With Shoeboxed Owner Doug Breaker  
Podcast: Small Business Tax Savings Podcast
Published On: Wed Jul 22 2026
Description: 👉 Ready to simplify your recordkeeping? Check out Shoeboxed to organize receipts, track mileage, and keep your business expenses audit-ready. Visit https://referrals.shoeboxed.com/mb4p7wl1ithiYou could qualify for thousands of dollars in tax deductions, but without the right documentation, the IRS could take them away.Mike sits down with Doug Breaker, owner of Shoeboxed, to explain how proper recordkeeping helps business owners protect their tax deductions. They break down what to document for receipts, meals, mileage, home offices, and business travel, how long to keep your records, and how simple tracking systems can help you stay organized and audit-ready.👉Find out how much your business could save in taxes.TaxSavingsPodcast.com/scorecard 🚀 Book your free demo call today. Click here or visit:https://taxelm.com/demo/Chapters: 01:00 Doug Breaker’s Journey to Owning ShoeboxedDoug explains how he went from working as a corporate CEO to purchasing Shoeboxed and becoming a business owner.05:00 How Shoeboxed Simplifies RecordkeepingDoug shares how Shoeboxed helps business owners digitize receipts, automatically collect expense information, and classify business mileage.06:00 What Counts as Proper Documentation?Receipts should capture details such as the date, vendor, amount, and business purpose, while mileage logs require the date, destination, mileage, and purpose of the trip.11:00 How to Organize a Backlog of ReceiptsBusiness owners with years of disorganized receipts should begin by digitizing recent records and creating a consistent process for tracking new expenses.15:00 What an Audit-Ready Mileage Log Should IncludeA proper mileage log should record the date, destination, miles driven, and business purpose of each trip rather than relying on an annual estimate.19:00 How Long Should You Keep Business Tax Records?Doug recommends keeping receipts, mileage logs, and supporting documentation for at least three years in a secure and accessible location.22:00 When Driving From Home Becomes Deductible MileageDriving from home to a regular workplace is generally commuting, but traveling from a qualifying home office to another business location can create deductible mileage.27:00 Deducting Expenses Before a Business Makes MoneyExpenses incurred before a business begins operating may be treated as startup costs. Establishing a paying customer can help show that the business has moved into its operational stage.32:00 Why Better Recordkeeping Protects Your Tax SavingsConsistently tracking every receipt and business mile helps protect deductions, reduce audit anxiety, and keep more money in the business.Podcast Host:Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings PodcastJoin TaxElm: https://taxelm.com🚀 Visit:  https://www.TaxSavingsPodcast.com 🚀 Check Out TaxElm: https://taxelm.com/🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/🚀 YouTube: www.TaxSavingsTV.com👋🏼 GET IN TOUCHYou can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏🙌LEAVE A REVIEWIf you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐🎙 ABOUT THE PODCASTThe Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.