Moneywise

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Jay Berard’s never sold a company, but with $2.5M in cashflow and $10M net worth, is he confidence-rich or risk-blind?"

Here’s what we talk about:

• His early days: a Craigslist job ad, 100% commission, no safety net… and a one-way ticket from Winnipeg.
• Ja...

Jackie breaks down exclusive data from 127 millionaire founders inside Hampton, revealing how motivation, money management, and mindset evolve as net worth grows, from $1M to over $100M.

Here’s what we talk about:

• Why financial security stops being a motivator after $50M—and what takes its place
• The "F*** You" number: What real numbers show is the threshold for total financial freedom
• Wealth allocation shifts: Crypto d...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report.

Andrew Wilkinson became rich in his 20s — but early wealth came with hard lessons. In this episode, Andrew opens up about:

• How he went from buying everything he wanted to nearly going bankrupt in 2008
• The emotional rollercoaster of building and losing wealth while still y...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Jess Chan scaled to 7 figures fast, then tore it all down. Today, she’s worth ~$10M, spends less than ever, and says profit > revenue every time.

Here’s what we talk about:

• Jess hit $40K/month as a freelancer, then walked away to build her agency, Longplay.
• Why c...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Is flying private a waste of money, or the ultimate time hack for the ultra-wealthy? In this episode, we break down what it really costs, who it makes sense for, and why even billionaires think twice.

Here’s what we talk about:

• Private aviation expert Preston Holland e...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Auren Hoffman reveals the unglamorous truth about angel investing—why he still does it, what he’s learned, and why it’s not for everyone.

Here’s what we talk about:

• Auren Hoffman made $60M—and then became an angel investor.
• He shares why angel investing isn’t as sexy as...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

He’s worth 8 figures, owns a private jet, and still tracks every dollar. Nick Huber says avoiding lifestyle creep is harder, and more important, than getting rich.

Here’s what we talk about:

• How Nick Huber built an 8-figure net worth from sweaty startups and smart real...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

After a nine-figure exit, Anastasia Koroleva went through divorce, failure, and identity loss. She reflects on what she didn’t see coming.

Here’s what we talk about:

• Anastasia’s journey from a bootstrapped nine-figure success to divorce, burnout, and identity loss
• Why secon...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Adam Robinson was days away from a $70M exit… then the buyer walked. But the deal collapsing turned out to be a blessing.

Here’s what we talk about:

• His current company now does $25M ARR with $1M monthly profit.
• He accidentally spent millions before the deal closed on l...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

After a $100M+ exit, Jace Mattinson blew $40K a month chasing lost time, until living the dream nearly ruined it.

Here’s what we talk about:

• Jace shares how he turned a failing 135-year-old business into a $160M exit.
• Why buying old and boring beat building from scratch...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

What happens when you grow up alongside a billion-dollar company, lose yourself chasing money, drugs, and approval,  and have to rebuild your life from scratch? That’s what happened to Alex Peycoff.

Here’s what we talk about:

• Why growing up in a soon to be billiona...

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Shane Cultra walked away from his family's five-generation nursery business—triggered, in part, by watching Succession. Along the way, he built up a $10M net worth, stacked Bitcoin, turned a blog into a domain empire, and made peace with a father who didn’t speak to him for ...

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

Mike Brown built an oil & gas empire, scaled his net worth to nearly $20 million, but ended up cash poor, losing $1.8M in a failed bet, and borrowing money from his wife to pay taxes. Now, he’s rebuilt his fortune, redefined what wealth really means, and is living a life designed around freedom, not just big numbers.

He...

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

There is no amount of money that will make you happy. There is also no amount that will stop making you more happy. 

Both of those things are true.

Our producer is not rich. But she has talked to 100+ people who are, and she (I) has learned a lot about your kind (is that wrong to say?).

In the Moneywise pilot,...

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

Eran Galperin bootstrapped a niche SaaS for Brazilian Jiu-Jitsu gyms, sold it for $32.5 million, moved to Japan, and is now quietly living the FIRE dream — with a few luxury upgrades.

Here’s what we talk about:
- How Eran went from $15K in the bank to a $32M exit (with 90% equity!)
- Why he ignored VCs and chose to bo...

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 million, gave most of his early money to his parents, and now he’s looking for internships.

Here’s what we talk about:

• How Vinay went from broke stoner to $50–70 million exit
• Why he voluntarily left tens of millions on the tabl...

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 a weed farm, a beach house, and a comedy club in Thailand.

Here’s what we talk about:

• How Chris accidentally “won” capitalism—despite deeply skeptical views of money
• What happens when your values, ego, and bank accoun...

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/year in sales, check out Hampton: https://www.joinhampton.com/.

Dan Berger sold his company Social Tables for $100 million in 2018. But his net worth today hasn’t moved at all. Why?

Here's what we talk about:

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 winning. From painting garage doors to building A1 Garage Doors into a massive industry leader, Tommy has played the long game—and he’s not slowing down anytime soon.

Tommy’s story is one of grit, sacrifice, and scale. He didn’t just...