Five Founders, Same Exit Value – Wildly Different Payouts

I’m Jackie Lamport, and on Money Wise we’re unpacking what founders actually keep from exits around thirty million. We’ll walk through five deals from past guests—the size sold, what cleared to founders, and why the results diverge so much.

First up, Aaron Galperin sold a majority stake in his gym software company for thirty two and a half million while holding close to half the equity; what did that mean for his pocket and role?

About thirty million went to me with a seller note and some dilution from an option pool, I stayed active at the company, and I had moved from California to Texas ahead of time to avoid the state tax hit.

So his payout was part cash, part note, taxed in Texas, and he still owns a big slice and remains involved.

Scott Galloway’s first big number shows how a sticker price can compress fast.

I sold Profit for thirty three million while owning roughly a quarter, split proceeds in a divorce, paid taxes, and netted two to three million; years later L2 sold for one hundred fifty eight million with founders and key staff holding most of the pie, which changed everything.

Alex Hormozi’s outcome was cleaner but even more striking.

We sold two thirds of Gym Launch for thirty one, all cash, paid about twenty percent tax, and I had already taken forty two million in distributions, so my total after tax take home was roughly forty five to fifty while keeping around thirty percent.

Brothers Chris and David Sinkinson accepted a forty million Canadian offer after a strong pandemic pivot, with no investors and no debt.

It was just the two of us on the cap table, we each received twenty million, and since we could not hold U.S. equity we got a small contingent instrument that later paid a few hundred thousand and was taxed more aggressively.

In Ontario, share sales typically incur about twenty five to thirty percent capital gains tax, so each likely cleared mid-teens Canadian, roughly ten to eleven million U.S.

Finally, Marshall Haas sold a controlling stake to Nick Huber at a company value near fifty two million.

I took about eighteen million in cash at close plus an eight point two million seller note with strong interest, kept meaningful equity, stayed on the board, and structured it for cash flow and purpose rather than an all-or-nothing exit.

Net, that was roughly twenty six million across cash and note with more upside from equity, and no day-to-day role.

Here’s the punchline: the sticker price is just a headline—ownership, structure, taxes, timing, and life circumstances decide your real outcome, so do not judge yourself by someone else’s scoreboard. Scott and Marshall sold for similar amounts yet walked with a few million versus tens of millions, and even near‑billion deals can leave a founder with around seventy million; the backstory there is wild if you want us to dig in next.