Small tax mistakes can cost you thousands, even when you think you’re doing everything right.

From missing a filing deadline to misunderstanding how a deduction works, small errors can quickly turn into penalties, lost deductions, and a higher tax bill.

In this episode, Mike answers real tax questions from small business owners covering gambling losses, BOI reporting, moving an S corporation to another state, the Augusta Rule, HSAs, late 1099s, estimated tax penalties, startup expenses, vehicle write-offs, and more. He breaks down the rules, explains the available options, and shares practical steps to help you stay compliant and avoid costly tax mistakes.

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Chapters

00:45 Gambling Losses, BOI Reporting, and Moving an S Corp
Mike explains gambling deductions, current BOI filing rules, and what happens when an S corporation moves states.

05:40 The Augusta Rule, HSAs, and Nonprofit Approval
Learn how to document Augusta Rule meetings, coordinate HSA contributions, and apply for 501(c)(3) status.

10:20 Health-Sharing Plans, Late 1099s, and Estimated Tax Penalties
Mike covers health-sharing deductions, missed 1099 deadlines, and penalties after a late-year property sale.

16:25 Seasonal Income, Inventory Credit, and Pre-Revenue Businesses
Find out how seasonal businesses handle estimated taxes, how much inventory to finance, and what to file before earning revenue.

20:15 Late Schedule C Filings, C Corp Owner Pay, and Vehicle Write-Offs
Mike explains prior-year Schedule C filings, how C corporation owners are paid, and choosing between mileage and actual vehicle expenses.

Resources Mentioned:

👉 www.FinCen.gov

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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🎙 ABOUT THE PODCAST
The 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.