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Episodes

Tax Loss Harvesting After A Liquidity Event With Earned

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June 3, 2026
Tax-Loss Harvesting After a Liquidity Event with Earned

A great deal can still fall short if taxes aren’t part of the strategy. Few business owners spend time planning for what happens after the transaction closes and the tax impact that follows.

In this episode of The Advisor’s Table, Brian and Michael sit down with Senior Wealth & Tax Advisor Carson Henderson from Earned to understand how proactive tax planning can change that outcome.

They explore how tax-loss harvesting strategies can be used for business owners after a large capital gain and how far ahead you should be thinking about implementation. Carson shares examples of healthcare owners who have executed these strategies through a private equity sale and a private doctor-to-doctor sale.

“While tax-loss harvesting has existed for some time, it was largely reserved for ultra-high-net-worth individuals. Today, with advancements in technology, more business owners have access to strategies that can help reduce their tax burden and better position them for long-term financial success in retirement.” — Carson Henderson, Senior Wealth & Tax Advisor at Earned

Key Takeaways for Healthcare Business Owners

  • Starting this process early produces better results. Tax-loss harvesting strategies can be implemented early in your career.
  • You don’t need a major exit to benefit. Tax-loss harvesting strategies can still be beneficial in other ways outside of selling your practice or business.

Why This Matters for Healthcare Business Owners

Tax strategy isn’t something to consider after decisions are made. This episode emphasizes how the difference between reacting to taxes and planning for them early can meaningfully change your long-term outcome.


Listen to the full episode above for the complete conversation with Carson Henderson from Earned.

"Everything I did with 7 Pillars was not only thorough, detailed, and well done, it was enjoyable. I really had a great time working with all of them...The peace of mind that I had knowing that every 'i' was dotted and every 't' was crossed and that I wasn't missing something was huge."
Dr. Kelly Toombs, DDSPractice Owner
Dr. Kelly Toombs, DDS
"I can't even imagine doing this process on my own... not only the negotiations way more than paid for itself, but just the process of due diligence—the way that 7 Pillars walked me through due diligence—I barely had to do anything... I highly recommend 7 Pillars. They were phenomenal."
Dr. Hilton Goldreich, DDSMulti-Location Practice Owner
Dr. Hilton Goldreich, DDS
"7 Pillars made sure that we knew what we were getting into, what to expect, and questions we didn't even know to ask and you know they had the answer before we even knew we needed them...I just couldn't imagine doing it by ourselves. I would recommend 7 Pillars to anybody going through this process."
Dr. Jason Montgomery, DDSPractice Owner
Dr. Jason Montgomery, DDS
"One of the things that really stood out to me was that they were very direct. They were very honest about what the process was going to look like, what our involvement was going to be, and also what to expect."
Alix LaurainCEO
"7 Pillars were not forcing us into the marketplace... they were really willing to value our practice, see if this makes sense for us, and provide us with the information ahead of time. 7 Pillars is to us what we are to our patient... they had the information, I could ask questions, I could do some research on my own if I wanted, but they were the experts."
Dr. Kimber Holmes, DDSPractice Owner
"7 Pillars gave me the whole picture. They understood my practice, they understood the offers, they broke it down to that next level so that I really understood what the deal was. We felt that even towards the end and after our transaction took place that everybody was still there still working to make sure that everything got put to bed... everything was done to a sublime level."
Dr. Joseph GrayPractice Owner
"Once they've got a feel for who you are and what your practice is, they can connect you with the right people. 7 Pillars just went over and beyond what I think anybody else would do to help, and that's what really stands out with them. If I had to do it all all over again, I wouldn't use anybody but 7 Pillars."
Dr. Richard BoatmanPractice Owner
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