Tax-Free Exits? Understanding Section 1202 Qualified Small Business Stock
Transaction Talk30 Okt 2025

Tax-Free Exits? Understanding Section 1202 Qualified Small Business Stock

Smart tax planning starts when you form your business! Today, we are joined by Caleb Powers to discuss one of the best-kept secrets in the tax code, Section 1202. Tuning in, you'll hear about our guest's impressive career, what 1202 stock is, why it's important to consider it when planning to sell a business, who qualifies, and so much more. We delve into the drawbacks of being a C-Corp business before Caleb tells us how the Big Beautiful Bill has enhanced Section 1202. We also discuss common mistakes he sees businesses make that cause them to lose their Section 1202 status, and Caleb reminds listeners of the importance of having a good team when planning an exit. Finally, Caleb ends with his invaluable tip of the day. If you want to save a fortune in exit taxes, this episode is for you, so be sure to press play now!

Key Points From This Episode:

  • Introducing Caleb Powers and a brief overview of his career.
  • What 1202 stock is and why it should be considered when selling a business.
  • Caleb walks us through who qualifies and who doesn't for Section 1202.
  • The drawbacks of being a C-Corp and what to consider when converting.
  • How the Big Beautiful Bill has enhanced Section 1202 and why it's for small businesses.
  • Some potential burdens that may come with having a Section 1202 business.
  • Common mistakes Caleb has seen that have caused businesses to lose their 1202 status.
  • The importance of having the right team in place when considering your exit options.
  • Caleb tells us a story about an entrepreneur who saved massively using Section 1202.

Tip of the Day: Surround yourself with people who understand Section 1202! It can make an enormous difference to the wealth you're trying to build!

Links Mentioned in Today's Episode:

Caleb Powers on LinkedIn

Caleb Powers Email Address
Jennifer Fox on LinkedIn

Eric Sigman on LinkedIn

Transaction Talk

Disclaimer:

The material on this site may be considered advertising under the rules of the Supreme Judicial Court of Massachusetts. This site is solely for informational purposes and provides general information only. Nothing on this site should be construed as legal advice or consultation either generally or in a particular case. Neither the receipt nor the distribution of materials constitutes the formation of an attorney-client relationship.

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