A tough tax lesson you don’t have to learn the hard way

I wasn’t the one selling a business.

But a friend, an advisor, was. He’d spent decades building something incredible. When a buyer came along, the number looked good. The handshake felt right.

But then the tax bill showed up.

And just like that, hundreds of thousands of dollars were gone. Not because he did anything wrong, but because he didn’t know what questions to ask before signing.

It wasn’t just about price. It was about deal structure, entity type, asset vs. stock sale, capital gains vs. ordinary income, state tax rules, it all added up fast.

That experience stuck with me. Because as a CPA, I see clients and advisors plan for exits and retirements all the time. But too many go in blind, unprepared for the tax implications and complexities that come with selling or transitioning a business. Taxes can dramatically affect the final outcome, sometimes turning what seemed like a great deal into a costly mistake.

Understanding the nuances of business tax planning is essential to protect your legacy and financial future. Too often, this critical step gets overlooked until it’s too late, and that’s where proactive guidance makes all the difference.

That’s why I’m grateful to have partners like JPTD Partners, who are proud sponsors of the Summit 2025 later this year.

They specialize in helping advisors maximize the value of their business and avoid getting crushed by taxes when it’s time to sell, whether that’s part of the business, or the whole thing. They know how to structure deals, ask the right tax questions, and prevent the costly surprises that can undo years of hard work.

You don’t need to be selling now to learn from someone else’s expensive lesson. As part of their sponsorship of the Summit they have offered to provide free “Street Level” valuations for anyone in the RTS Nation. No matter where you are in the process or even if you’re years from even considering it this can be incredibly valuable insight on your practice so don’t miss this opportunity.

Happy Tax Planning,

Steven Jarvis, CPA