Q&A: Are You Making These Common Small Business Tax Mistakes? episode artwork

EPISODE · Jun 10, 2026 · 26 MIN

Q&A: Are You Making These Common Small Business Tax Mistakes?

from Small Business Tax Savings Podcast · host Mike Jesowshek, CPA

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.👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:https://www.taxsavingspodcast.com/starterkit🚀 Book your free demo call today. Click here or visit:https://taxelm.com/demo/Chapters00:45 Gambling Losses, BOI Reporting, and Moving an S CorpMike explains gambling deductions, current BOI filing rules, and what happens when an S corporation moves states.05:40 The Augusta Rule, HSAs, and Nonprofit ApprovalLearn 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 PenaltiesMike covers health-sharing deductions, missed 1099 deadlines, and penalties after a late-year property sale.16:25 Seasonal Income, Inventory Credit, and Pre-Revenue BusinessesFind 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-OffsMike 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 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.

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, vehic...

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Q&A: Are You Making These Common Small Business Tax Mistakes?

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How long is this episode of Small Business Tax Savings Podcast?

This episode is 26 minutes long.

When was this Small Business Tax Savings Podcast episode published?

This episode was published on June 10, 2026.

What is this episode about?

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...

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