Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.com Rob Townsend says you’re wrong about financial advisors… mostly. And he’s built an 8-figure firm to prove it. Here’s what we talk about: Why $3M liquid is Rob’s version of “f*** you money” How he went from $0 to 8 figures by modernizing financial planning Why the old guard of wealth management is fa...
Aug 26, 2025•51 min•Ep. 67
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.com Everything you need to know about turning art into a real (and risky) investment strategy. Carlos Cardenas is a Private Wealth Advisor at Austin Wealth Management, bringing over 20 years of experience in alternative asset management. His background spans commercial real estate, technology, and healt...
Aug 19, 2025•43 min•Ep. 66
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report Inside Alex Hormozi’s decade-long climb from $0 to $200M+. Here’s what we talk about: A transparent breakdown of his $200M+ net worth: $95M in liquid assets, $100M+ in illiquid equity The Gym Launch explosion: from near-bankruptcy to $42M in distributions and a $31M cash sale by age 31 Why selling made him feel poorer , and why he’ll never cut off his “cash flow firehos...
Aug 12, 2025•40 min•Ep. 64
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...
Aug 05, 2025•41 min•Ep. 65
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report Amber Lee was literally brought back to life, and then decided to start over. Here’s what we talk about: After a near-death experience in 2020, Amber finally launched her dream matchmaking business from the hospital. She bought her mom a house and moved to Puerto Rico, prioritizing freedom over wealth. Year one: $1M revenue. Now: $3M+ with fewer clients and higher margi...
Jul 29, 2025•40 min•Ep. 63
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 How Ronan Berder accidentally built a consulting agency, scaled it to 8 figures, and sold it, despite never enjoying the work. Here’s what we talk about: Why Ronan stayed in China running a business he didn't love, and the deep sense of duty he felt to his team. Walking away from an opportunity to follow his passion in order to focus on scaling t...
Jul 14, 2025•44 min•Ep. 61
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. Jay’s net worth: ~$10M, mostly liquid, mostly public equities, and why he values his business eq...
Jul 08, 2025•42 min•Ep. 60
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 disappears, bonds and real estate dominate at the ultra-high end Surprising ins...
Jul 01, 2025•22 min•Ep. 59
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 young What it's actually like to cross the nine-figure mark Why luxury spend...
Jun 24, 2025•34 min•Ep. 58
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 chasing $1M in revenue nearly burned her out, and what she did to rebuild. The shif...
Jun 17, 2025•43 min•Ep. 57
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 explains the true cost of flying private, from charter to full ownership. When d...
Jun 10, 2025•37 min•Ep. 56
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 it sounds. The truth about money: yes, it did make him happier. How he tracks...
Jun 03, 2025•37 min•Ep. 55
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 estate plays. Why he keeps over $2M liquid and doesn’t touch stocks. His exact...
May 27, 2025•43 min•Ep. 54
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 second businesses often fail, and how success the first time around can actuall...
May 20, 2025•1 hr•Ep. 53
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 land, crypto, and a new mortgage. Then came a surprise 60% tax bill, thanks to ...
May 13, 2025•41 min•Ep. 52
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. He hit a $5M net worth—then spent $40K/month trying to “make up for lost tim...
May 06, 2025•42 min•Ep. 51
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 billionaire status family taught Alex the wrong lessons about value and self-worth. How wild...
Apr 29, 2025•37 min•Ep. 50
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 a year after he left. Here’s what we talk about: How Shane went from pit ...
Apr 22, 2025•43 min•Ep. 49
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. Here’s what we talk about: How Mike went from $2K in his bank account to ...
Apr 15, 2025•51 min•Ep. 48
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, we asked the question “at what point will more money stop making you happy”. Turns ou...
Apr 08, 2025•33 min•Ep. 47
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 bootstrap — and how it paid off years later - The long, slow ramp: 4 years to $1...
Apr 01, 2025•48 min•Ep. 46
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 table—and doesn’t regret it The emotional crash that came after the deal closed W...
Mar 25, 2025•57 min•Ep. 45
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 account collide Why he spent nearly his entire fortune in six months—and doesn’t regret...
Mar 18, 2025•47 min•Ep. 44
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: How Dan went from bootstrapping websites to an eight-figure exit Why his net worth hasn’t gro...
Mar 11, 2025•48 min•Ep. 43
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 grow a company; he mastered the art of exiting, reinvesting, and buildi...
Mar 04, 2025•31 min•Ep. 42
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 stretches as if it’s $9M. Rob, a member of the Hampton community, shares how he built a successful marketing agency while living in Medellín. Once an anti-capitalist hippie, Rob’s journey took him from hitchhiking across Canada to scaling a business with $3.6M in annual revenue—all while crafting a lifestyl...
Feb 25, 2025•32 min•Ep. 41
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 nostalgia—it's an investment play. Rob Walling is a serial entrepreneur who sold his SaaS companies for millions. But instead of Ferraris, he spends big on collectibles—rare comics, original artwork, and even historical autographs. For him, it’s about diversification, but also about reliving childhood jo...
Feb 18, 2025•44 min•Ep. 40
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 many founders who struggle with identity and purpose post-exit, they had a built-in support system: each other. With a 10-year age gap and complementary skills, they navigated the highs and lows of entrepreneurship as a team. And when they suddenly found themselves financially free, their brotherhoo...
Feb 11, 2025•44 min•Ep. 39
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 wins, something changed: he had kids. And suddenly, the drive that once defined him wasn’t as important as being present for his family. Chris started as a scrappy startup founder, building and selling multiple companies for over $50 million each. He worked directly with Elon, made bold investments, ...
Feb 04, 2025•47 min•Ep. 38
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 didn’t build his wealth by following the typical playbook. Instead of just chasing cash, he let his curiosity lead the way—and it’s resulted in over 40 successful exits, groundbreaking innovations, and a life that’s anything but boring. Now, with a thriving family office and a long list of projects, ...
Jan 28, 2025•42 min•Ep. 37
