TL;DR:
A business owner sold his HVAC company and paid nearly $3 million in taxes — despite working with a financial advisor. With proactive planning, we could have saved him $1.7 million. If you're even thinking about selling your business, the planning must begin 3–5 years before the sale. And not all advisors are equipped for that kind of work.

I recently shared a story in a Yahoo Finance article about one of the most common — and expensive — mistakes I see business owners make when selling a company.

Here’s the quote:

“One of my clients sold an HVAC business without tax planning. It was a mistake. Between federal capital gains, NIIT, and state taxes, he paid close to $3 million straight to the IRS.”

“With proper planning, we could’ve saved him about $1.7 million.”

The surprising part?

He was already working with a financial advisor.

The Wrong Advisor at the Wrong Time

This client wasn’t careless. He was smart, successful, and had professional help during the sale.

The problem?
His advisor wasn’t equipped for the complexity of a business exit.

There was:

• No coordinated tax plan

• No entity restructuring

• No QSBS or installment sale strategy

• No charitable trust, gifting, or reinvestment blueprint

They focused on managing money — not helping the client manage the sale.

And that difference?
It cost him $1.7 million.

Selling a Business Isn’t Just a Financial Event — It’s a Tax Event

Most people underestimate how much tax can eat into a sale. Between federal capital gains, the Net Investment Income Tax, and state income taxes, the bill can climb fast.

The worst part?
Once the deal closes, there’s no way to unwind it. You either planned properly in advance, or you didn’t.

This is why I tell every business owner:
If you're even thinking about selling your company, start planning 3 to 5 years before the sale.

That timeline gives you access to tools and strategies most people never hear about until it’s too late.

What That $1.7 Million Could Have Done

With the right team in place and a few years of runway, he could have:

• Qualified for QSBS and paid $0 on a large portion of the gains

• Created a charitable remainder trust to offset income and support causes

• Used installment sales to reduce his overall tax rate

• Funded a tax-free income plan through Roth conversions or SBLs

• Built multi-generational wealth through trust planning and gifting

Instead, his old advisor didn’t bring these strategies to the table. And that’s exactly why planning — and who you plan with — matters.

One Sale. One Shot.

You only sell your business once. There are no do-overs.

That’s why we built our Compound Cultivator™ process — to help business owners make smart, strategic decisions around their exit, taxes, reinvestment, and long-term planning.

We coordinate every piece — financial, legal, tax, estate — so your wealth isn’t eroded by oversight or inexperience.

If you're planning to sell your business — or already sold and wondering what’s next — let’s talk.
👉 Book Your Free 15-Minute Strategy Call

Keep Compounding.

-Heath