A $150M Ride: Private Equity, Planes, & a $1M Butt Tattoo

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

Chuck Yates rode the wildest wealth rollercoaster: $150M up, $82K down, now back at $20M. In oil & gas private equity, he made (and lost) fortunes and never flinched. For Chuck, money’s just part of the story. Mindset is everything.

Here’s what we talk about:

How Chuck went from $150M to $82K and why he wasn’t phased
What it’s like to build wealth in the high-stakes world of energy PE
The absurd economics of buying a plane
How he managed to tour with celebrities
Why your relationships matter more than your balance sheet
The mindset shift that came after divorce, getting fired, and starting over
How Chuck accidentally became a podcaster and ended up co-founding an AI startup
Why self-worth shouldn't be tied to net worth and how Chuck redefined success on his own terms

Sponsors:

Get US caliber talent at offshore prices with https://www.oceanstalent.com/
Achieve your dream body with https://www.dailybodycoach.com/moneywise
The best phone system for teams at http://www.openphone.com/moneywise

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/

Chapters:

(0:00) Chuck's Bold Introduction
(3:01) Living Comfortably with $20 Million
(3:25) The Rise in Private Equity
(6:36) Early Career and Entry into Energy
(10:41) The Wild World of Oil & Gas
(13:12) Personal Life Changes and Divorce
(13:46) The Van Halen Plane Era
(22:50) Getting Fired and Hitting Bottom
(31:22) The Comeback: Digital Wildcatters and AI
(35:52) Life Philosophy and Values

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.