Podcast Episodes

I'm worth $50m and Have No Idea What To Do With My Life

Episode 45

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

Vinay Hiremath co-founded Loom and sold it for nearly $1 billion… then walked away from $60 milli…

Published on 9 months ago

I'm worth $50m and Have No Idea What To Do With My Life

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

Vinay Hiremath co-founded Loom and sold it for nearly $1 billion… then walked away from $60 milli…

Published on 9 months ago

Inside the $30M Exit of a Socialist Buddhist

Episode 44

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

Chris Cooke is a socialist Buddhist who sold his company for $30 million… then blew most of it on…

Published on 9 months, 1 week ago

I Sold for $100M and Now I Spend $1M/Year

Episode 43

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.

Inspired by real conversations happening in the Hampton community.

If you're a founder doing at least $3M/yea…

Published on 9 months, 2 weeks ago

How Tommy Mello Became a Billionaire Painting Garage Doors (And How He Shares the Wealth)

Episode 42

What does it take to turn a blue-collar business into a billion-dollar empire?

For Tommy Mello, the answer is simple: relentless competition, strategic investing, and an unwavering commitment to winni…

Published on 9 months, 3 weeks ago

"I Fast-Forwarded My Life 10 Years”: How Geo-Arbitrage 3X’d My Wealth and Changed My Life

Episode 41

What if you could fast-forward your financial goals by ten years just by moving abroad?

That’s exactly what entrepreneur Rob Hoffman did when he relocated to Colombia, where his $3M net worth stretche…

Published on 10 months ago

How Comic Books Are Making Me Richer with Rob Walling

Episode 40

Would you put millions into comic books? It sounds crazy, but for Rob Walling, it’s part passion, part strategy.

He’s met people at the airport just to pick up a single book. But this isn’t just nosta…

Published on 10 months, 1 week ago

From Startup to $40M Exit – And We’re Still Just Brothers

Episode 39

Most founders feel isolated after selling their company. Chris and David Sinkinson didn’t—because they had each other.

The brothers built and sold their startup, AppArmor, for $40 million. But unlike …

Published on 10 months, 2 weeks ago

Elon Musk's Acquisition Made Me $50M, But Fatherhood Redefined My Life

Episode 38

What if the key to success wasn’t grinding harder—but learning to let go?

Chris Bakke made 10s of millions selling two companies, including one to Elon Musk’s Twitter. But after years of chasing big w…

Published on 10 months, 3 weeks ago

$500M and Still Asking "What’s Next?": Peter Wokwicz’s Guide to Curiosity-Driven Success

Episode 37

What if chasing curiosity, not cash, was the key to a richer, more fulfilling life? 

Peter Wokwicz turned his relentless curiosity into a $500 million fortune—and found happiness along the way.

Peter d…

Published on 11 months ago