Exit Planning Strategies That Can Eliminate Capital Gains
February 26, 2026 •
In this episode, Jason is joined by Jamie Stinson of Advanced Exit Solutions to discuss strategies that can dramatically reduce—or even eliminate—capital gains taxes when selling a privately held business. They examine planning opportunities for both long-range exits and imminent sales, including charitable structures and valuation strategies that may significantly limit tax exposure. If you’re a business owner thinking about succession, private equity offers, or rollover equity, this episode outlines options worth considering before signing a deal.
Tune into this episode to also learn:
● How early exit planning can shield future business appreciation from taxation.
● Strategies available when a sale is already in motion.
● How charitable components can reduce capital gains exposure by 60–70%.
● Why rollover equity may create a second opportunity for tax elimination.
What we discussed
● [00:00:40] Introduction to Jamie Stinson and his focus on tax mitigation strategies for business owners.
● [00:03:28] The difference between long-term exit planning and imminent sale strategies.
● [00:05:46] A real-world example of shielding $40 million in appreciation from capital gains tax.
● [00:08:28] How charitable structures can reduce capital gains taxes by 60–70% in near-term sales.
● [00:10:23] A case study involving a $40 million sale and multi-generational income planning.
● [00:15:23] How valuation timing impacts tax outcomes in growing businesses.
● [00:20:39] Using rollover equity to eliminate taxes on the “second bite of the apple.”
3 Things To Remember
- The earlier you begin planning for a business exit, the more opportunities you may have to limit taxes on future appreciation.
- Even if a sale is imminent, there may still be structures available that substantially reduce capital gains exposure.
- Rollover equity and charitable planning strategies can transform a taxable event into a multi-generational wealth opportunity.
Memorable moments
(00:02:45) “If this is actually doable, this is really the coolest tax planning idea that I’ve ever seen.”
(00:05:58) “So $40 million of that transaction was not subject to any taxes, state capital gains.”
(00:21:30) “It’s not deferral. It’s elimination.”
Useful Links
Connect with Jason Gabrieli: jgabrieli@hfmadvisors.com | LinkedIn
Connect with Jamie Stinson: LinkedIn
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HFM Investment Advisors, LLC is a registered investment adviser. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. All investments involve risk and are not guaranteed. Information expressed does not take into account your specific situation or objectives and is not intended as a recommendation appropriate for any individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment advisor to determine whether any information presented may be suitable for their specific situation. Past performance is not indicative of future performance.
