Are You Going to Jail for Tax Planning? Tax Attorney Sets the Record Straight

Are you worried a tax strategy could land you in trouble with the IRS? In this episode, Mike Jesowshek sits down with tax attorney Ed Lyon to break down what tax risk actually means. They explain why most business owners do not get in trouble for smart tax planning, where the line between gray-area strategy and fraud really sits, and why proper implementation matters just as much as the strategy itself. They cover audit risk, common red flags, what to ask before moving forward with an advanced strategy, and how business owners should think about their own risk tolerance when building a tax plan. 👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: 🚀 Book your free demo call today. Click here or visit: Chapters (02:00) Why Business Owners Fear Tax Planning People don't go to jail for legal tax planning. They go to jail for fraud, lying, and backdating documents. (05:00) Why Tax Strategies Exist in the First Place The tax code is designed to encourage certain behavior. Congress uses tax incentives to push homeownership, healthcare benefits, investing, and charitable giving. (12:00) When a Legal Strategy Becomes Illegal A strategy can be perfectly valid in theory, but fail when implemented poorly. (24:00) How to Vet an Advanced Tax Strategy When someone pitches an advanced strategy, transparency matters. Ed explains what questions to ask, what red flags to look for, and why business owners need to understand who they are dealing with before moving forward. (27:00) How Business Owners Should Think About Risk Tax risk is just another business risk. The real goal is to understand your own risk tolerance, know where your advisor falls on the conservative-to-aggressive spectrum, and make informed decisions. (31:00) A Favorite Strategy for the Right Client Ed closes by sharing one tax strategy he likes for the right candidate, the charitable lead trust, and explains why the best strategy always depends on the client’s goals, income, and long-term plan. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join TaxElm: 🚀 Visit: 🚀 Check Out TaxElm: 🚀 Join our Free Facebook Group: 🚀 YouTube: 👋🏼 GET IN TOUCH You 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 REVIEW If 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 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.

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Are You Going to Jail for Tax Planning? Tax Attorney Sets the Record Straight is an episode from Small Business Tax Savings Podcast by Mike Jesowshek, CPA.

This episode is 34:07 long.

This episode was published on Mar 25, 2026.

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