He Sold For $8M and Regrets It, And The Reason Why Is Shocking.

He Sold For $8M and Regrets It, And The Reason Why Is Shocking.

Please answer our short Moneywise listener survey! (Very, very short): joinhampton.com/moneywisefeedback JOIN HAMPTON: These episodes often come directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw. HOW FOUNDERS ARE BUILDING WEALTH: How much do founders actually make, spend, invest, work, and keep in net worth? Hampton surveyed founders directly and put the answers into one report. Download it for free here: https://joinhampton.com/mw-wr EPISODE DETAILS: Thibault — known online as Tibo — is a French indie hacker who spent six years failing at startups before building Tweet Hunter during Covid lockdown and selling it for $10 million. Except the real number was more complicated than that: $2 million up front, $8 million in earn-out, and 18 months of some of the most stressful building of his life to get there. He walked away with just under $3 million post taxes — and says he regrets the sale entirely. Today, Tibo is doing over $1 million a month in revenue across a portfolio of five software products he's built since that exit. His personal spend is negligible. He has no financial advisor, keeps roughly 50% of his net worth in cash, and puts almost everything investable into index funds. This episode gets into the full deal structure, the psychological cost of the earn-out period, what he calls the "frozen state" that hits founders after a big exit, and why he says he will never sell a company again. Timestamps: * 02:12 — Full guest intro: who Thibault is, the Tweet Hunter story, deal structure breakdown, and episode roadmap * 08:08 — The $10M deal unpacked: earn-out structure, revenue milestones, and what he actually collected * 10:17 — The co-founder split, the 25% influencer equity deal, and whether he'd do it again * 14:09 — How the influencer partnership worked and why they replicated it on Tapio * 26:17 — "Getting a ton of money up front feels unhealthy" — Thibault on why lump-sum exits are psychologically dangerous * 28:14 — The "frozen state": why founders can't ship after a big exit * 30:42 — The earn-out burnout period: stress, loss aversion, and the 18 hardest months of his life * 34:37 — "It was a bad decision financially" — Thibault's verdict on the sale * 38:15 — Nomadic life, the Vietnam hacker residency, and how wealth changes how he travels * 42:42 — No financial advisor, no trust in wealth managers — why everything goes into S&P 500 * 45:29 — Personal spend breakdown: ~$8K/month — rent, food, tech gadgets, and that's basically it * 48:27 — What happens to the ~$90K/month delta: cash, S&P 500, and acquiring more products * 49:45 — The portfolio strategy: five products, two unannounced, and the 2026 scaling challenge * 51:12 — Building a distribution bridge between all his products with an AI agent * 53:06 — Raising kids with money: unconditional safety as the foundation for risk-taking

You’re Rich. Here’s How To Raise Great Kids.

JOIN HAMPTON: This episode came directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw. HOW FOUNDERS ARE BUILDING WEALTH: How much do founders actually make, spend, invest, work, and keep in net worth? Hampton surveyed founders directly and put the answers into one report. Download it for free here: https://joinhampton.com/mw-wr THIS EPISODE OF MONEYWISE: 70% of wealthy families lose all their money by the second generation. 90% lose it by the third. The data is even worse for the kids themselves. Children from households making $200K+ have rates of anxiety, depression, and substance abuse 2 to 3 times the national average. 22% of affluent suburban girls show clinically significant depressive symptoms. So how do you raise a kid in a wealthy household without breaking them? In this episode of MoneyWise, I went back through every conversation we've had on the show about parenting and money. Doctor Becky. Taylor Adams (from a multi-generational billionaire family in LA). Alex Peikoff. Shane. Jane. Hank. Neil Patel. Scott Galloway. The pattern they all kept landing on was uncomfortable. Most parents with real money are accidentally setting their kids up to fail. Not because they're bad parents. Because they're doing exactly what their instincts tell them to do. I'm a dad of two. I'm trying to figure this out in real time. Here's what the research, the experts, and the founders who already screwed it up are telling us. WHAT YOU'LL LEARN: - Why "entitlement" is actually a fear of frustration, not a character flaw - The Carol Dweck Columbia study that should change how you talk to your kids - Why your kid is running on your behavior, not your rules - The "shirtsleeves to shirtsleeves in three generations" trap (and why it's not about money) - How allowance teaches financial trade-offs (and why unlimited Amazon access kills it) - The single biggest regret of founders after a life-changing exit - Why downsizing your house might be the best parenting decision you ever make CHAPTERS: 00:00 The 16-year-old in the airport 02:57 Frustration tolerance is the most important life skill 05:30 Why wealthy kids have 2-3x higher anxiety and depression 08:00 Monkey see, monkey do: the emulation problem 11:00 70% lose it in 2 generations. 90% in 3. 14:00 Praise effort, not traits (the Dweck study) 18:00 Just because you love business doesn't mean your kid will 21:00 Why allowance only works if money is finite 25:00 The Scarsdale busboy who sees $300 sweatshirts as 30 hours of work 28:00 Scott Galloway's moving goalpost 30:17 The presence problem (the hardest one for me) 33:00 The 5 rules I'm taking with me REFERENCED EPISODES: - Taylor Adams: How a multi-generational billionaire family thinks about wealth - Doctor Becky on parenting through money - Hank: Inside a 24,000 sq ft home - Neil Patel on going from 10,800 sq ft to 3,000 sq ft - Alex Peikoff: The Macedonian milk family - Jane: Finding out about a $20M inheritance in her late 30s - Pete: $80M exit, rock bottom after ABOUT MONEYWISE: MoneyWise is the podcast where wealthy founders open up about the real numbers behind their lives. Net worth. Monthly burn. Portfolio allocation. The stuff nobody talks about in public. Hosted by Daniel Berk and produced by Hampton. SPONSORS: Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now.

He Made $400k/Month Before 30... Then Realized It Meant Nothing

MoneyWise is a Hampton podcast. Hampton is a private, vetted community for founders doing $3M or more in revenue. Apply at https://www.joinhampton.com/?utm_source=youtube&utm_medium=video&utm_campaign=yt051126. From Minecraft maps to $400k months — but the money isn't the story. Nathan May grew up in one of the poorest neighborhoods in Ohio. His mom made $32,000 a year. He never left the state until he was 18. At 15, he was selling custom Minecraft maps to famous YouTubers and making his first $100K. He went to Wharton, joined BCG, quit, and built one of the fastest-growing newsletter agencies in the country before turning 30. But the week he hit his first million dollars, his mom died. And he felt nothing. In this episode, Nathan gets brutally honest about what money actually gave him — and what it didn't. We go deep on the community he's built in New York with a group of founders sharing an office, a monthly revenue leaderboard, and the kind of real talk that doesn't happen anywhere else. He calls it the Media Mafia. He says it's changed his life more than any dollar amount ever has. We also get into: * Growing up in poverty and never leaving Ohio until 18 * How a Minecraft addiction became his first real business * Leaving a six-figure BCG career to bet on himself * Building a $1M ARR agency in under a year with 1,000 newsletter subscribers * His actual net worth, his $10M target, and why he keeps almost no cash * Why he thinks the wealthiest people he knows are often the least happy Timestamps 00:00 - Cold open 00:58 - Introducing Nathan May 01:23 - Small talk / how Nathan starts his day 02:32 - The agency, the numbers, how life has changed 03:24 - Growing up poor in Ohio — never left the state until 18 05:35 - He originally wanted to be an actor 06:04 - The Minecraft business: how a video game addiction made him $100K at 15 09:05 - Wharton, Wall Street culture shock, and the path to BCG 10:36 - What BCG actually changed about his life 12:01 - Building the agency: newsletters, Schwarzenegger, and why it felt like video games again 15:32 - His real relationship with money: checking account, savings, leverage strategy 16:52 - The $10M number: how he used ChatGPT to find his "enough" 18:34 - The Media Mafia: seven founders, one office, a monthly revenue leaderboard 20:31 - Being at the cusp — exciting, terrifying, or both? 23:07 - Why IRL community is the highest-leverage thing a founder can build 26:03 - What Hampton means to him 27:31 - His mom's passing, the $1M milestone, and why none of it felt like anything 29:24 - Can you be successful without community? 31:39 - What's next and closing thoughts MoneyWise is the podcast where high-net-worth founders get radically transparent about how they actually make, spend, invest, and think about money. Hosted by Daniel Berk and presented by Hampton. Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com

He Made $3M a Year and Decided He Had Enough

MoneyWise is a Hampton podcast. Hampton is a private, vetted community for founders doing $2M or more in revenue. Apply at https://www.joinhampton.com/?utm_source=youtube&utm_medium=video&utm_campaign=yt050526. MoneyWise | Jonathan Goodman Jon Goodman built a $35M fitness education empire from a one-bedroom apartment in Toronto, never raised a dollar, never sold a company, and never left Canada — even though the government takes 53 cents of every dollar he earns above a certain threshold. In this episode, Jon breaks down exactly where his $14M net worth lives, why he found his "safe number" at $7M, how he spends $22-25K a month across Toronto and six months abroad every year, and why he thinks moving to a tax haven is a rich person's dumbest game. Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now.

Does Making $100M Make You Happy?

Chapter Timestamps 00:00 — Homeless at 26, $100M exit at 32 02:22 — Building Mutesix: one of the first productized Facebook ad agencies 09:39 — The 2019 sale and what Steve actually took home 11:52 — The wire hits — at the Western Wall in Israel 14:46 — "The money didn't change my life": post-exit identity crisis 16:31 — How Steve actually spends: the chef, the donations, the Birkin he never bought 19:55 — Why he's obsessed with insurance (and what he tells founders) 23:18 — Post-exit on a Tuesday: the daily search for meaning 25:07 — Did the $100M exit actually make him happy? 32:03 — Looking back 15 years — and what the next 5 look like At 26, Steve Weiss was homeless in Los Angeles, sleeping in his car in a 24 Hour Fitness parking lot with $200 to his name. Six years later, his Facebook ads agency Mutesix sold for $100 million to Dentsu. The day the money hit his account, he was standing at the Western Wall in Israel — and got a phone call that made him realize money doesn't fix what's broken inside you. In this episode of MoneyWise, host Daniel Berk sits down with Steve Weiss to walk through the parts of a nine-figure exit nobody puts in the press release: how much he personally took home, if the wire made him happy, and what post-exit life actually looks like on a random Tuesday when you've already "won." In this conversation: * How Steve built Mutesix from 4 clients in 2013 into one of the first productized Facebook ad agencies — and sold it to Dentsu in 2019 for $100M * The emotional moment the wire hit at the Western Wall, and the tragedy that hit the same day * His real spending today: a private chef 3–4 days a week, why his wife asks for nonprofit donations instead of Birkin bags, and the cause they're funding * Why he over-indexes on life and health insurance — and the advice he gives every founder * The post-exit purpose vacuum — what he calls "almost impossible to replicate" — and how he's filling it now with family, angel investing through SGD, his podcast, real estate, and possibly politics * What he'd do differently if he could rewind 15 years * The honest answer to the question every founder secretly asks: did $100 million actually make him happy? If you've ever wondered whether the exit really fixes anything, this is the episode. MoneyWise is the personal finance podcast for high-net-worth founders. Hosted by Daniel Berk and produced by Hampton — a private, vetted community for founders and CEOs running businesses doing $2M+ in revenue. Apply at joinhampton.com. Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now.