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

Moneywise

Hampton

Business, Entrepreneurship, Investing

4.8 • 674 Ratings

🗓️ 5 August 2025

⏱️ 44 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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.

Transcript

Click on a timestamp to play from that location

0:00.0	All right, so here's the deal. I just came from our 25-person all-hands meeting with all my staff at Hampton.
0:08.6	About four of the 25 people there, they were people we found via a company called Oceans.
0:15.3	Offshoring, it gets a bad rap. And it gets a bad rap because a lot of people think that the people you hire via
0:21.8	offshoring firms are low-level talent and do low-level work, or they just do stuff that AI is
0:28.0	already replacing. That is not true at all. The people who we have, they help us with marketing,
0:33.4	they do operations, and we treat them as fully part of our team because they are.
0:39.5	And what's great about oceans is you can get top talent and finance marketing operations,
0:44.0	basically any role that you're hiring for, for only about $3,000, at least that's the starting
0:48.9	point.
0:49.6	And you can get amazing, talented people in like two weeks.
0:52.9	I think we've got one of these folks who work for us. I think we've got her in like five days and she's amazing. We've worked with her for like a year now. If you don't want to burn a lot of cash, but you still want the best high caliber people, you guys got to check them out. It's oceanstalent.com. And please tell them that Sam sent you and they're going to give you a little bit extra special
1:11.5	treatment. Again, oceanstalent.com.
1:18.2	He looked at me and he goes, Chuck, how much are you worth? And I said, well, I'm worth a million
1:24.3	dollars. I didn't have a million dollars to my name. I just, it was, I just didn't want to sound like a broke dick, right?
1:31.0	Chuck Yates has some guts.
1:33.0	He's confident, he's bold, and when he was in private equity,
1:36.4	his methods were unconventional.
1:39.0	I got tattooed on my butt at one of my roast, but it raised a million dollars. That's the attitude that made Chuck peak at $150 million, and then dropped down to 80K.
1:50.0	And now he's back to a nice 20 million again.
1:53.0	It might all sound completely crazy, but for Chuck, it was all just part of the game.
1:57.0	It's a roller coaster. Even the drops are fun, you know? I'm Harry Morton, and this is Money Wise, a podcast not about how to make money, but about how substantial wealth changes your life, for better or worse. It's made for the members of Hampton, a community of high net worth founders to connect and learn from each other on exactly the topics that we're going to talk about today with Chuck. So I'll speak more about it later on, but for now, if you're a founder doing at least 3 million in revenue,
2:21.3	go and check it out at joinhampton.com.
	...

Transcript will be available on the free plan in 13 days. Upgrade to see the full transcript now.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Hampton, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Hampton and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.