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•32 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•47 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•56 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
Are you obsessively checking your portfolio—or avoiding it entirely? What’s the right approach to managing your money post-exit? In this Mini-Wise episode, Sam Parr breaks down how three ultra-wealthy entrepreneurs—Chuck (net worth: hundreds of millions), Travis (net worth: $50M), and Anne Mahlum (net worth: $100M+)—handle the mental rollercoaster of market fluctuations. Each shares their unique strategy, from completely logging off to obsessively staying informed, and how these choices impact t...
Jan 21, 2025•13 min•Ep. 36
Most people think Bryan Johnson just wants to live forever. They’re wrong. Bryan’s real goal is to leave a legacy that will last centuries. In this episode, we uncover the extraordinary vision of Bryan Johnson, an entrepreneur driven by the audacious mission to earn the respect of people living in the year 2500. Bryan isn’t just the man who sold Braintree (the parent company of Venmo) for $300 million—he’s an innovator investing every resource he has into shaping humanity’s future. From building...
Jan 14, 2025•46 min•Ep. 35
Why do we let numbers define us—and what happens when they finally stop moving? Fred’s journey from corporate finance to a multi-million-dollar exit reveals the emotional rollercoaster behind financial success and the unexpected lessons that follow. Fred, an introspective entrepreneur, sold his company for a mid-eight-figure sum. His story isn’t just about numbers—it’s about the sacrifices, anxieties, and the emotional toll of tying your self-worth to success. From his immigrant family upbringin...
Jan 07, 2025•44 min•Ep. 34
RE-RUN If you have the money to put anything you could possibly want in your home, should you do it? This episode’s guest, “Hank” did, and as a result, his home ended up being 24,000 square feet. But with 24,000 square feet, there is a lot to go wrong. So are the upkeep, repairs, and bills worth the square footage? Can a home with all the fancy features you can imagine actually bring more joy to your life? Building (or buying) a house this size is no small feat, and there are numerous things to ...
Dec 31, 2024•35 min•Ep. 33
RE-RUN There was a time when Neil Patel said a $15k/month burn rate was all he needed. But now his monthly burn is $200k. Roughly. He’s not completely certain… because he doesn’t budget. So what changed in his life to make his burn rate increase nearly 14 fold? That’s what this episode is going to find out. Neil Patel is a household name (for marketers). He’s an entrepreneur and blogger known for his expertise in digital marketing and SEO. He co-founded companies like Crazy Egg , Hello Bar, and ...
Dec 24, 2024•31 min•Ep. 32
What’s the real cost of building wealth—and how do you stay grounded after achieving it? Steve Houghton, a billionaire entrepreneur, has a life philosophy that’s as intentional as his business strategies. From self-made success to crafting a fulfilling personal life, Steve shares the five pillars that help him stay healthy, happy, and wealthy. Steve’s journey started with selling books as a teenager, earning the equivalent of $100,000 today, and grew to building successful ventures in real estat...
Dec 17, 2024•40 min•Ep. 31
RE-RUN Imagine being worth $150 million. Liquid. Now imagine being worth that much, and only spending $5,000 a month. That’s the reality for this episode’s guest. “Cam” is going to share a lot of financial details with us, so he’s asked to remain anonymous. What we can tell you, is that he made most of his money when a business he started went public at a valuation of around a billion dollars. That happened in his late 30s. In his early 30s, Cam was still only worth a couple grand. There’re a lo...
Dec 10, 2024•42 min•Ep. 30
What happens when wealth pushes your relationships to the limit? Navigating life after a massive financial windfall isn’t easy—it can transform your life, your marriage, and your happiness in unexpected ways. Our guest, Chuck, shares his story of selling his company for $2.5 billion and the emotional and relational challenges that followed. His perspective is shaped not only by his own journey but also by a family history of building and losing fortunes. Chuck’s background is as bold as it gets....
Dec 04, 2024•35 min•Ep. 29
What happens when the big exit doesn’t fill the void? Josh Payne thought selling his company for $80 million would be the defining moment of his life. Instead, it sent him into one of the darkest periods he’d ever experienced. Josh’s story is a testament to the complexity of success. As the founder of StackCommerce, Josh grew his company from $0 to $32 million in annual revenue, eventually selling it for a life-changing sum. But with his emotional wellbeing tied so closely to his business succes...
Nov 26, 2024•38 min•Ep. 28
What would you do if you became a millionaire at 18? For MLB pitcher Jacob Turner, the real question was: how do I make sure I don't lose it all? Jacob signed a $7 million contract with the Detroit Tigers as a teenager, and suddenly, his life changed overnight. While most of us can’t imagine dealing with that level of wealth so young, Jacob had to figure it out fast—and he didn’t want to be another cautionary tale of an athlete who blew it all. Jacob Turner isn’t just a former MLB pitcher—he’s a...
Nov 19, 2024•41 min•Ep. 27
We just hit our 25th episode! To celebrate, we’re doing a special recap of the best lessons from all our past conversations. Sam’s looking back at the standout advice from founders, entrepreneurs, and experts who opened up about what really happens when you hit major financial success—and the stuff no one talks about. You’ll hear insights from Mike Beckham on why giving back keeps lifestyle inflation in check, Dr. Becky’s take on raising resilient kids in a world of privilege, and advice from fo...
Oct 29, 2024•31 min•Ep. 26
Jess Mah is worth half a billion dollars—and she’s tired of pretending otherwise. Jess Mah, entrepreneur and founder of InDinero, dives into the power of radical transparency and how it’s impacted her personal and professional life. Raised by an entrepreneurial mother, Jess aspired to success from a young age, but her path to wealth wasn’t always smooth. By 34, she has built ownership stakes in several companies, but more importantly, she’s learned to stop caring what others think about her weal...
Oct 22, 2024•47 min•Ep. 25
What’s the true value of money when faced with a life-or-death situation? Mitch found out the hard way when his wife was diagnosed with cancer. As a highly successful entrepreneur with a net worth of nearly $100 million, Mitch had built a life of financial security. But when faced with his wife’s illness and his own health scare, he discovered that no amount of money could buy control over life’s toughest moments. Mitch's story is one of resilience, from his early entrepreneurial days, selling c...
Oct 15, 2024•46 min•Ep. 24
What happens when you don’t sell your company and keep growing it for decades? For Oscar, it means you become a billionaire. Oscar bought a company every six weeks for 20 years and now his business is worth about $50 billion. Yet, he still wears $15 t-shirts and lives by the values that helped him achieve success. In this episode, he shares how he became a billionaire while always putting family and faith first. He discusses his humble beginnings, the influence of his father, and how he’s now pa...
Oct 08, 2024•44 min•Ep. 23
Can success create a false sense of invincibility? For Pete, it did—and it cost him millions. After selling his business for $80 million, Pete felt unstoppable. But his overconfidence led him into a risky venture that didn’t pay off. Determined to prove he wasn’t a one-hit wonder, Pete ignored the warnings, thinking his past success guaranteed future wins. Instead, he faced one of the hardest losses of his career. In this episode, Pete shares how his upbringing shaped his hunger for security, ho...
Oct 01, 2024•38 min•Ep. 22
How Do You Stop Hustling When You’ve Already Won? Laura Roeder told herself that at $5 million liquid she could live the life she wanted and refocus her life on what matters most: living. Unlike a lot of entrepreneurs who get caught up in the game and keep chasing more, Laura stayed true to that goal and quit hustling harder than she had to. But how did she avoid the endless treadmill for more? Laura Roeder, founder and successful SaaS entrepreneur, joins the show to share her journey of hitting...
Sep 24, 2024•41 min•Ep. 21
Ever wondered what it feels like to be the richest person in a tiny town in the middle of nowhere? Today’s guest, Travis, is worth $50m, yet he’s never been tempted to leave his hometown of 2400 people. Travis has already had an exit of $25m, and he’s about to double that with a second exit. Now he’s navigating life as the local big shot. From curious neighbors asking about his money to balancing wealth without being flashy, Travis shares the surprising perks—and awkward challenges—of being a bi...
Sep 17, 2024•37 min•Ep. 20
13 million dollars is a lot. But is it enough to retire on? For pre-epiphany Ryan Begelman, the answer is no. Ryan built his wealth working in the corporate world, then decided to risk it all and bought into Bisnow. That risk paid off, and Ryan made a huge profit. But despite his successes, he found himself grappling with lifestyle inflation, misguided investments, and financial uncertainty. In this episode, Ryan opens up about his struggles with managing wealth after a big exit, how flashy spen...
Sep 10, 2024•40 min•Ep. 19
