I Have $12M But I'm Broke Every Month

About this episode

We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wr

Why do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.

He sold his company for a headline $54 million — the number that actually hit his account was $12 million.

Brandon Harris is the founder of Playmaker, a sports media company he built starting with $15 shoutout posts on Facebook pages and grew into a business with 20+ million followers and shows featuring athletes like Shaquille O'Neal and Jalen Brunson. The deal that sold it carried a $54 million headline — but between a brutal, near-failed first year with the acquirer and an earn-out he ended up negotiating his way out of early, what actually hit his account was $12 million. Today all of it stays invested, he borrows against it instead of selling, pays himself just $75,000 a year at his new startup, and hasn't taken a single day off since the deal closed.

This episode gets into the real mechanics behind a $54 million number — the earn-out structure, the ugly first six months with a Danish acquirer that nearly tanked the whole deal, and the negotiation that got Brandon out early. We go deep on exactly where his money lives today: a 60/40 portfolio, a $600,000 "high risk" Robinhood account, and a $3 million credit line he taps instead of ever selling a share. Brandon also opens up about the 2008 crash that cost his family everything, the tattoo on his shoulder that explains why he can't stop building, and the one regret from the whole Playmaker run that still bothers him.

Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mw

Timestamps:
00:00 — Intro: the $54M headline, the real number that hit his account, and how he funds his life today without selling a single share
01:30 — Growing up "very privileged" — until his dad's real estate portfolio got wiped out in the 2008 crash
02:07 — Supporting his family financially at 18: "basically roller coaster"
04:14 — Buying $15 shoutout posts on Facebook pages — the move that led him into media
05:06 — Inside the $54M Better Collective deal — "one of the most complicated structures" he's dealt with
07:42 — "Where I netted out was about 12 million total"
09:48 — The first six months of the earn-out: missing a $17M revenue target by more than half
12:18 — "That was probably the least healthy I've been personally in my life"
12:51 — The turnaround: landing Shaq and Jalen Brunson, "the thrill of my career"
15:56 — Where the $12 million actually lives today — a 60/40 portfolio and a credit line built to avoid capital gains
17:35 — The $600,000 Robinhood account for his concentrated AI and robotics bets
18:28 — The real debt picture: $3 million tapped on the credit line, $1 million left on the mortgage
19:01 — Why he only pays himself $75,000 a year — "a big discount from the corporate 250 I was making"
22:19 — His actual number before he can stop working: "I'd like to get to 20 million"
24:13 — Zero days off since the exit: "No time, no time"
25:09 — The tattoo on his shoulder and the "trauma" behind the drive to keep building
33:51 — The regret that still bothers him: "no wins really mattered"

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