For those who sold for $5M+ what surprised you most about the tax bill?

Starting to run the numbers on what I’d actually walk away with after selling and it’s honestly shocking how much goes to taxes. Between federal capital gains, state taxes, and whatever else gets pulled out I’m starting to wonder if the net number is even worth it at certain price points. Feels like there’s a range where you sell for what looks like a life-changing number but after taxes and broker fees you’re sitting there wondering if you should’ve just kept the cash flow.

For those who’ve actually closed, was the tax hit what you expected or did it catch you off guard? And did anyone structure the deal specifically to manage the tax burden, installment sales, seller financing, opportunity zones, anything like that?

(Talked about QSBS in a previous post)

Trying to figure out what’s worth exploring with a CPA now vs what’s just noise.