Episode Details

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You 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.

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Chapters: 

01:00 Doug Breaker’s Journey to Owning Shoeboxed
Doug explains how he went from working as a corporate CEO to purchasing Shoeboxed and becoming a business owner.

05:00 How Shoeboxed Simplifies Recordkeeping
Doug 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 Receipts
Business 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 Include
A 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 Mileage
Driving 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 Money
Expenses 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 Savings
Consistently 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 Podcast
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