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May 2, 2025 8 mins

Would You Sell Your Family Business If You Could Avoid Capital Gains Tax?” - Dave Lorenzo

What You’ll Discover Today:
Would you sell your family business if you could pay no capital gains tax, reward your employees, and preserve your legacy? In this episode of the Inside BS Show, Dave Lorenzo explores how an ESOP (Employee Stock Ownership Plan) might make that possible. It’s a compelling option for business owners with $10M+ in annual revenue and 50+ employees—and it might be the best exit you’ve never considered.


Key Topics Discussed:

  • What an ESOP is and how it works
  • How family business owners can exit with zero capital gains tax under Section 1042
  • Why ESOPs help preserve legacy and boost employee engagement
  • When an ESOP makes the most sense (and when it doesn’t)
  • The costs and complexities of setting up and managing an ESOP
  • How ESOPs offer flexibility for long-term transition planning
  • A real-world story of a business owner rethinking their exit after learning about ESOPs
  • Why ESOPs are especially valuable when there's no clear successor in the family
  • The importance of stability, cash flow, and operational independence in ESOP suitability
  • Dave’s call to action for family business owners to explore this underutilized exit strategy

Links and Resources:

Call to Action:
If your family business is doing more than $10 million in annual revenue and you’re curious about exiting without giving a big chunk to the IRS, this episode is for you. Don’t wait for a buyer to knock on your door—build your own. Reach out to Dave Lorenzo or check out the interview with ESOP expert Andrew Nicolai to take the next step.

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