Moneywise

Jaksot

• 
  I Asked 40 Millionaires Their Biggest Regret 15.09.2026 22min

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.I asked 40 millionaires their biggest regret. One answer was just two words: "withholding love."This episode started with a simple survey: 40 millionaires, one question — what's your biggest regret? The answers ranged from $22K a year dumped into life insurance instead of Bitcoin ($11M of upside gone) to hundreds of bitcoins sold at $300 to make payroll. But cross-referenced against 100+ Moneywise conversations, every answer collapsed into just three regrets: I can see the life I almost had. I didn't become the person I thought I could become. I thought I had more time.Then it gets into the science. Why bronze medalists look happier than silver medalists. Why finance is only 2.5% of most people's regrets but dominated this survey. Why the person you never became can bother you longer than any mistake you actually made. Why an $80M exit sent one founder to rock bottom. And a three-question Regret Test to figure out whether your regret is still useful — or just expensive entertainment.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — The survey: 40 millionaires, one question, and the answers that looked completely random01:02 — Every regret collapses into three buckets01:24 — Regret vs. disappointment: why regret needs an alternate reality02:25 — The brain science: patients with orbitofrontal damage don't feel regret03:14 — Your brain uses regret to change future decisions before you make them04:02 — Bucket 1: "I can see the life I almost had" — "the stock market is basically a regret calculator"05:23 — The Olympic study: why bronze medalists look happier than silver medalists06:27 — Finance is only 2.5% of most people's regrets — so why was this survey drowning in them?07:36 — The Opportunity Principle: agency creates regret, and rich people have had a lot of agency08:25 — Bucket 2: "I didn't become the person I thought I could become"09:08 — Ought self vs. ideal self — and why ideal-self regrets never get closure10:26 — "The unlived version of you never has a bad quarter"11:02 — The famous "you'll regret what you didn't do" stat — and the 2,600-person study that broke it13:04 — The 23-year-old already in the "never enough stage," and the moving goalposts from $10M to $1B13:56 — Bucket 3: "I thought I had more time" — kids, health, and the $80M founder who hit rock bottom14:52 — Why priorities flip when time feels scarce (and Daniel's midlife crisis at 30)16:13 — When to engage with a regret and when to let it go — what the research on older adults found17:21 — The Harvard study: relationships at 50 predicted health at 80 better than cholesterol19:45 — The Regret Test: three questions to ask about your biggest regret20:44 — "Regret in 4K": why money doesn't eliminate regret — it makes it higher resolutionSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  Patrick & Kathy Terry (P. Terry's): "Why We Said No to $100M" 08.09.2026 1t

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.They turned down a $100M offer for their burger stand — now they're giving the company to their 1,800 employees.Patrick and Kathy Terry opened a 500-square-foot burger stand in South Austin in 2005 — three months into their marriage — selling $1.60 hamburgers. Kathy barely took a salary for over a decade. In 2016, with ten locations, a buyer offered them between $70 and $100 million, and they said no, pulling out just under $10M — the only money they've ever taken in 21 years. Today P. Terry's runs 37 locations, employs 1,800 people, does between $150 and $200 million a year growing 20%+ — and instead of selling, they're transferring the whole company to their employees through an Employee Ownership Trust, something fewer than 100 American companies have ever done.This episode gets into the exact numbers behind the offer they walked away from, why $10M felt like enough, the $900K in interest-free loans they've made to hourly employees (with only $5K in defaults), the "Maggie rule" that governs every company decision, and how an EOT actually works versus an ESOP — including why one protects your culture forever and the other can be forced to sell it. It ends with the question underneath it all: what a business is for when the check stops mattering.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — Cold open: "It was between 70 and $100 million and you turned it down."02:53 — Kathy's West Texas upbringing, quitting the law firm, and giving herself a 500% raise06:33 — Patrick's path: Kool-Aid stand at 5, ad agency by day, running a pizza place nights and weekends09:30 — Springing the burger stand idea on Kathy three months into their marriage: "I didn't think he'd ever do it"11:05 — Year one: $600K in revenue from 500 square feet — and still in the red after depreciation16:09 — The 2016 "dog and pony show": realizing for the first time what the business was worth17:35 — "It was between 70 and $100 million" — a 10–12x offer, and why they turned it down20:23 — Kathy's real fear: "Who's going to take care of our employees? They're not going to bake birthday cakes anymore."23:01 — Patrick was stunned to learn they had 300 employees — he thought it was 80 or 9024:27 — Why the birthday cakes matter: "For a lot of our employees, that is how they celebrate their birthday"25:59 — Barely taking a salary for 12 years, then pulling out just under $10M — the only money ever taken27:17 — The June EOT transition: gifting and selling the first ~11% to the trust via a seller's note33:36 — The origin of interest-free loans: Vinny's broken truck and $15034:05 — $900K loaned to hourly employees over 20 years — only $5,000 ever defaulted37:14 — The Maggie rule: every decision tested against the woman who's worked the grill for 21 years42:05 — Kathy explains EOT vs. ESOP — and why one protects the culture forever49:40 — Profit sharing starts next year: 5% of EBITDA now, 20% in five years, based purely on tenure54:49 — "The island sucks. This is okay." What Patrick learned about what he actually wanted59:20 — Kathy's open offer to walk any founder through the EOT modelSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  He Ran PayPal With Elon. Now He Has $100M and Spends Nothing 01.09.2026 51min

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He co-founded PayPal with Elon Musk, sold Personal Capital for nearly $1B — and spends $70K a year.Bill Harris has a résumé that barely fits on one page. He was CEO of Intuit, founding CEO of PayPal — in the room with Elon Musk, Peter Thiel, and Max Levchin above a bakery near Stanford — and then founded Personal Capital, which he grew to $23 billion in AUM before selling it to Empower Retirement for close to $1 billion. He's done something like that 11 times. Today his net worth is around $100 million, he's 70 years old, and he spends less than $100,000 a year. He sold his houses, cars, airplane, and 31 pets (including two mountain goats and an iguana) and moved into a small cottage near Miami Beach where he bikes to work every day.This episode gets into what $100 million actually looks like when it's spread across public equities and private operating companies — and why the man who built one of the most important wealth management firms in history keeps his own annual spend near $70K. We go deep on the PayPal origin story, what it was like being "theoretically the CEO" in a room full of people whose egos "wouldn't fit in a large gymnasium," and the specific moment Bill realized that his houses, cars, and airplane weren't making him richer in the ways that mattered. He also shares his best piece of investing advice for people in their 30s, his take on why the S&P 500 isn't as diversified as most people think, and what he calls "freedom money."Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps: 00:00 — Cold open: "There wasn't a single one of us whose ego would fit in a large gymnasium" 00:36 — Full guest intro: who Bill Harris is and why this episode matters 03:23 — Bill's origin story: the golden boy path, Intuit CEO at 40, and realizing "I am not a good manager" 06:33 — What money actually is: "It is a rocket fuel. It's the scarce resource you need to build the life you want" 07:38 — The monthly spend reveal: $70–80K a year, all in — "my addiction is Amazon" 09:04 — Life phases: family dole → NYC studio → two houses, 31 pets, and a 1906 Woodside farmhouse 14:20 — Net worth reveal: ~$100M, cut in half by divorce, and the barbell portfolio breakdown 15:27 — Why he doesn't do "fancy investing": survivorship bias, absurd fees, and why alternatives rarely outperform 17:31 — The Evergreen Wealth philosophy: why 80–90% equity is what he'd tell a client with his profile 19:07 — How to value a private company: "Two things dominate it — markets and story" 21:47 — "Things are time": the real cost of owning two houses, four cars, and a small airplane 24:33 — PayPal origin story: "We were close to fisticuffs most days. I was theoretically the CEO" 27:38 — Luck vs. skill: "I'd say it's 80 to 90% luck" — and what that actually means 30:13 — The personal payout from PayPal and Personal Capital: specific numbers, post-tax 32:01 — Why he's self-funding Evergreen with $10M of his own money: "Freedom. I have no boss" 38:05 — Why he still works at 70: mastery, not money — "I can't think of a bigger waste of time" than golf 42:48 — Best investing advice for your 30s: "Hive off a piece and let it marinate" 43:44 — Why the S&P 500 is riskier than it looks: top 10 stocks = 37% of the whole index 45:40 — "Freedom money" defined: the thing that lets you say yes to your own life 48:33 — Closing: "Money is a means to an end. It's not an end."Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  How a $1.5B Wealth Manager Spends His Money 25.08.2026 48min

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He manages $1.5 billion for other people — and still tracks his own spending in a paper checkbook.Glenn Ullmann is a former Air Force pilot who left the military at 29 with a couple hundred thousand dollars, cold-called 200 strangers a day out of a Ponte Vedra phone book, and built Ullmann Wealth Partners into a $1.5 billion RIA that has never had a down year — including 2008. He stopped worrying about money somewhere north of $20 million. Now 63, he spends $30–40K a month, flies his own $1.25M Cirrus, gives more to charity than he can deduct, and still shows up to the office every day.This episode gets into the tension between saving and actually living: why Glenn tells clients with health issues to fly private before their kids do it with the inheritance, how a $10M portfolio pays you $300K a year in "rent" whether markets are up or down, and why he thinks stocks are a bad word. We also cover how he gave up 80% of his own firm to keep his partners, the paper ledger that runs his life, the client who started at $100 a month and now takes the best trips on earth, and why he'd tell a 20-year-old to study English or history instead of finance.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:01:46 — Who Glenn is, what Ullmann Wealth Partners does, and why "returns don't matter if you rear-end Melinda Gates without an umbrella policy"04:16 — Growing up in his grandfather's plastics business, the Robin's-egg Cadillac, and the gold coin that says "your friendship means more to me than a pot of gold"06:26 — A Morgan Stanley account at 14, paper route money, and his first stock: Sears Roebuck07:44 — Nobody from his high school went to the military. He went to the Air Force Academy three days after graduation: "the best thing I ever did, other than marrying my spouse"11:50 — The Cirrus G7, the parachute that lowers the whole plane, and the button his wife can push if Glenn stops functioning mid-flight13:35 — From AWACS pilot to pharma rep to stockbroker: dialing 200 people a day, 10 conversations, one client17:45 — Net worth leaving the Air Force at 29 and the million-dollar goal on a piece of paper that "never happened"19:26 — The $2M–$20M client sweet spot, and why the firm has never contracted in 25 years — even 2007–200921:57 — Why he went from owning 100% of the firm to 20%: "How could they not have equity?"24:03 — The 11x17 "life map," and the client who was stabbed and left for dead in her New York apartment26:15 — HENRYs who save $10K a month and still need to be told to go enjoy the rest: "People get cancer. People die falling off a ledge."28:49 — "If you don't spend this money and fly first class, your kids will when you're dead"30:40 — The net worth where Glenn stopped worrying: "probably above 20"31:49 — Alimony, fun, and the pen-and-paper checkbook ledger a $1.5B wealth manager uses to track his Amex33:29 — The $1.25M four-seat plane, $40–50K a year to operate, and a $30–40K monthly burn before philanthropy35:10 — Giving appreciated stock and exceeding his deduction limit every year36:21 — Why he still goes to work at 63, the wingman system, three chronic illnesses, and "sometimes a founder needs to get out of the way"39:40 — The Melissa example: $100 a month in 1993 to the best trips on earth41:26 — Where to park $10M after a liquidity event: "you're going to collect around $300,000 a year in dividends and interest"42:55 — Not a real estate guy, the $100K driveway, and "I never invest in things that eat while I'm asleep"44:48 — 90% in global equity, and why "they're not stocks, they're companies"45:40 — Reframing an $80K private flight as a month and a half of portfolio income47:39 — What he'd tell a 20-year-old picking a major: English or historySponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  5 Things Rich People Refuse to Buy 18.08.2026 17min

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.A $3 billion founder's money advice: keep driving the Chevrolet. Here's why the richest guests all say the same five things.After 100+ episodes of Moneywise, the same five spending refusals kept showing up — from a $3B founder who's never sold a company, a guy who lost 95% of his net worth and won't buy his own socks, and Bryan Johnson, who spends $2M a year on his body and almost nothing on anything else. None of them read the research. There's 50 years of it, and they all landed in the same place anyway.This episode covers all five: first class, new cars, meaningless stuff, angel checks, and kids' comfort — plus the study behind each one (lottery winners, the MIT Celtics auction, the marshmallow test follow-up). Then Anne Mahlum, who sold SolidCore for nearly $100M and forces herself to spend $200K/month, tears the whole list apart. The episode ends with a 10-minute exercise using two questions that decide what stays on your card statement.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwEpisodes Mentioned:How Rich Is 'Rich Enough' to Fly Private? — https://www.youtube.com/watch?v=5ZyTo6gppPw"I'm worth about $3 billion": What Happens When You DON'T Sell Your Business — https://www.youtube.com/watch?v=uZM0K9eqzx0What It's Like to Lose 95% of Your Net Worth Overnight (the socks guy) — https://youtu.be/fW-F3MKwevIBryan Johnson: I Probably Won't Actually Live Forever — https://www.youtube.com/watch?v=icWHq_xjhacHow to Not Ruin Your Kids with Your Wealth ft. Dr. Becky — https://www.youtube.com/watch?v=uB1SmMA-nLkTimestamps:0:00 — Cold open: the $3B founder, the socks guy, and Bryan Johnson's $2M body budget0:28 — 100 episodes in, the same five patterns kept repeating — and 50 years of research explains them1:05 — Why guests reveal their real numbers on Moneywise1:50 — #1: First class. "I still fly coach unless it's international" — his "poor kid habit"2:27 — Hedonic adaptation, and the lottery winners who scored lower on enjoying breakfast3:52 — #2: New cars. The $3B founder's advice: don't buy the Ferrari, drive the Chevrolet4:14 — The Millionaire Next Door data (most popular millionaire car: Ford F-150), "big hat, no cattle"4:40 — The commute study: zero relationship between car value and happiness5:35 — #3: Stuff. The socks guy's filter: "Does this dollar come back to me or is it gone?"6:03 — Stanford brain scans: every purchase is want vs. hurt6:28 — The MIT Celtics auction — credit card bidders paid double7:26 — #4: Angel checks. Bryan Johnson writes none — half of deals lose money, 7% produce 75% of returns8:41 — Opportunity cost neglect and attention residue: every check is an open tab in your head10:15 — #5: Kids' comfort. Parents who could buy any seat, flying the family in coach on purpose11:06 — The marshmallow test follow-up wealthy parents actually care about12:11 — 70% of family money gone by generation two, 90% by generation three13:17 — The counterargument: Anne Mahlum ($115M, spends $200K/month) — "I hate when people don't spend on principle"14:19 — The 2023 rerun of the $75K happiness study, and buying back time15:55 — The 10-minute exercise: two questions to run against last month's card statement16:33 — If you run a $3M+ company: HamptonSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  He's 27 and Runs His Family's 7 Companies 11.08.2026 41min

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He spends $50,000 a month and keeps $50,000 in the bank. He's 27.Mo Moahid is a 27-year-old who runs the finances for his entire family — parents, brother, sister, and seven operating companies across Canada, Dubai, and Pakistan. His great-grandfather built the family fortune. The next generation lost it. His dad rebuilt the whole thing from a sales job after immigrating to Canada, and Mo grew up watching both halves of that cycle happen in his own house. He started his first company at 18, scaled it to 200 employees, sold it at 21 for low seven figures, and now moves capital between line painting, real estate development, consumer electronics, eSIMs in 125 countries, and the AI company he started with his 21-year-old brother.This episode gets into what it actually looks like to manage generational money instead of making it: why he keeps almost nothing liquid, how a $50,000 monthly burn covers five people, what happens when your dad is the chairman and your brother is your co-founder, and how inheritance gets split between three siblings before anyone dies. We go deep on the acquisition he closed the week before we recorded, the corporate job his father made him take, and the question he's already thinking about at 27 — what he wants his own kids to inherit, and what he'd rather they didn't.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  $247M Net Worth, $100k/Month Burn: Inside Onyi Odunukwe's Money 04.08.2026 42min

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He turned down $250 million for less than half his company — and admits he'd say yes today.Onyi Odunukwe is the son of two Nigerian immigrant doctors who dropped out of nursing school during finals week and opened a tanning salon at 21. By 30 he had seven locations, sold five to Palm Beach Tan for $2.3 million in a single week, and thought he was rich. Eight years later his net worth is $247 million — roughly $100M in commercial real estate, $194M in business equity across 26 companies, and under $10M in cash — and he recently walked away from a $250 million offer for 49% of Glo Tanning.This episode gets into the exact breakdown of a $247M net worth, why he rejected the biggest check of his life and what changed his mind since, his $75-100K monthly burn (full-time driver, live-in nanny, a ranch on the way), the franchise math behind Blackstone's $8B Jersey Mike's deal, how he plans to keep his kids from being ruined by money — and a confession he's never made publicly before.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  He Sold For Over $40M. Here’s His Exact Cut. 21.07.2026 39min

  We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He got his first $5M check and expected to feel superhuman. The next day was one of the most disappointing of his life.Jesse Pujji walked away from a Goldman Sachs job where he made $500K at 25 — with a boss making $3M and a group head making $20M — to bootstrap an ad agency on $33K per partner and a stack of Amex cards. Ampush cracked the Facebook arbitrage before almost anyone: $100K in monthly revenue in June 2010 became $2M a month with $600K in EBITDA fourteen months later. He scaled it to half a billion in annual ad spend and 250 employees without raising a dollar, turned down $25M at 27, sold 20% to Red Ventures in 2015, and sold the whole thing to New Mountain Capital in 2022 for somewhere between $40M and $60M on a 35% stake. He never got the nine-figure number he made up in his head, and he says chasing it was the mistake.This episode gets into the exact allocation of a post-exit portfolio, why Jesse refuses to let his advisors put illiquid startup equity on his balance sheet, what $500K a year of "normal" spending actually buys, and why he asked his financial advisor how people possibly spend more than that. He's honest about the gap between the money he expected to change him and the money that didn't. And we spend real time on the part most founders avoid: three kids who never saw him grind, a Greenlight allowance split into thirds, a $63 JCPenney paycheck at 16 that taught him more than any of it, and the question of whether to leave them anything at all.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — Jesse's origin story: immigrant household in St. Louis, a snow shoveling business in middle school, and $33K each plus Amex cards to start Ampush02:00 — The Facebook arbitrage that changed everything: $100K/month in June 2010 to $2M in revenue and $600K in EBITDA fourteen months later02:49 — "Sandbox entrepreneurship" — Facebook cold-calls them: "Who the hell are you guys? You're one of our top 100 advertisers"04:24 — Why he left Goldman at 25 making $500K: "I would rather make half of my future expected earnings and do something I feel excited about"06:18 — The $25M offer two years in, why they said no, and the $3M dividend they took instead — $1M each, which bought his SF house07:30 — The made-up number that wrecked them: hoping for $150M, getting $60–75M offers, and turning down $190M in Marin stock09:24 — The Red Ventures deal and $5M after tax: "I thought I would get wings or superhuman strength... nothing changed"11:16 — 2022: selling to New Mountain and walking away without going with the deal13:12 — The exit number, on the record: a $40–60M range on a stake "a little bit more than a third"16:04 — The Zone of Genius framework, and why being a CEO sat in his zone of excellence — good at it, drained by it17:52 — Gateway X by the numbers19:06 — Whether the scarcity ever goes away: "nine days out of ten" became "one day out of ten," and the coach question he couldn't answer20:16 — The Deer Valley condo, and finally understanding why people buy vacation homes21:08 — Full portfolio breakdown and why he tells his advisors to mark his startup equity at zero23:24 — Annual spend 26:52 — The schedule that makes it work: Tuesdays and Thursdays he misses bedtime, Monday/Wednesday/Friday he doesn't, and he deletes Slack on vacation28:16 — The thing that keeps him up: "They've gotten all the fruits of the grind without actually observing the grind"29:23 — Greenlight, allowance equal to their age, and splitting it into thirds — spend, save, give30:19 — Running a Starbucks P&L with his 9-year-old daughter in the store32:30 — The four-bucket framework: spend it, give it to the government, give it to charity, or give it to your kids34:44 — A Schnucks family board member on generational wealth: "Money doesn't ruin kids. Lack of values does."35:36 — What Jesse wants said at his funeralSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  He Turned Down $11B... Here's Why 07.07.2026 53min

  Craig Newmark turned down an $11 billion offer for Craigslist, and he's already given away $570 million of his own money chasing a number even bigger than that.This podcast is made by Hampton, a community for founders doing on average $25 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you're a founder, apply here: joinhampton.com/mwCraig founded Craigslist off a mailing list in 1995. He turned down that $11 billion offer, and since then has given away $570 million through his foundation, aiming for a billion before he dies. He funds NYPD bomb squad gear, an NYU cardiologist's AI research, Wikipedia, journalism schools, and pigeon rescue. He's 73, hasn't owned a car in ten years, and just upgraded from $50 Skechers to $80 Skechers.This one gets into what happens once a founder's number stops being the problem, the Sunday school lesson behind his moral compass, why his own headline net worth is wrong, the two causes eating most of his giving budget, and his plan to train an LLM to keep making his philanthropic decisions after he's gone. It closes on Take Nine, his campaign for the nine-second pause that stops most scams.Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  He Sold For $1.5B But Will Never Retire 01.07.2026 50min

  He had $15 in the bank and a $1M judgment against him. Eight years later, Nestlé bought his company for $1.5B — then shut it down.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwMichael Wystrach built Freshly out of the wreckage of a failing restaurant, with $15 in the bank and a personally-guaranteed lease that left him with a $1M judgment against him. Six years later he sold the company to Nestlé for $1.5B — then watched it get shut down. He never took time off. He started a veterinary platform with his sister, raised a $75M venture fund, and put almost his entire payout back to work.This episode gets into what really happens to your bank account after a nine-figure exit — secondary sales, earn-out math, his actual living costs, his real estate philosophy at 2% interest rates, and what it felt like to lose the company he built after selling it. He also shares why he believes the first $10M matters more than the hundredth, and why he plans to keep building for the rest of his life.Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  He Sold 4 Companies for $1.5B. The $13M Exit Changed His Life. 23.06.2026 42min

  We did something nuts: we got 50+ founders to reveal their net worth, portfolios, income, expenses. Its free and right here: https://joinhampton.com/mw-wrWhy this podcast exists:Hampton is a community for founders. Members do an ave of $20m/year in revenue.Tons of the convos within the community are about money: how to invest, how to spend, how much to pay yourself...all this stuff you can't Google.We thought "Let’s just make these convos public". And thus, this podcast Moneywise came to be.We publish weekly. Click the subscribe button and the goodness will be delivered. Also...we've done 100+ episodes. If you want the aggregate info of all the numbers, meaning the net worth, spending, income of 50+ founders ranging from $10m to $1 billion: https://joinhampton.com/mw-wrOk, so let's talk David Royce, today's guest:He built the same pest control company four times — $13M, $30M, $135M, $1.5B — and says the first exit was the most life-changing.David Royce sold four pest control companies — Moxie, Eco First, Altera, and Aptiv — each bigger than the last, culminating in a $1.5B sale of Aptiv when it was doing $508M in annual revenue. He kept 100% equity through the first three, gave 25% of the last one to his employees, and personally walked away with hundreds of millions across the run. He's now on an indefinite sabbatical, investing through Iconic (the firm that manages Zuckerberg's and Dorsey's money), with half his net worth in S&P 500 and the rest in private equity, direct deals, and alternatives — including multiple Anthropic investments.This episode covers the exact mechanics of each asset-sale exit, why David kept restarting instead of holding, his full portfolio framework (including the 4-year cash buffer strategy), the "the answer is just a little more" moment that hit every entrepreneur in the room, and the story of flying his dying father on a private jet from a New Orleans hospital to Cedars-Sinai at 2am — made possible only by one call to a CEO WhatsApp chain.Timestamps:00:01:39 — David's full intro: four companies, four exits, what actually happened with the money01:55 — First company (Moxie): nearly went bankrupt the first year, how a cash flow crisis taught him "cash was king"03:14 — The asset-sale strategy: selling customers and technicians to Terminix while keeping the sales operation04:57 — "Pretty close" — David confirms Forbes' reported $13M and $30M exit figures05:37 — Why he gave 25% of Aptiv to employees and stepped back as chairman06:23 — Aptiv was doing $508M in revenue; Daniel and David settle on $1.5B as the sale range07:13 — What he actually took home: cap gains, California taxes, "hundreds of millions"08:37 — Net worth today: "do the math backwards and figure it out"09:09 — Portfolio breakdown: 4-year cash buffer in fixed income, S&P 500 with tax-loss harvesting, alternatives11:31 — "I just invested in Anthropic — three different times in the last year and a half" via Iconic14:35 — "The one that was life-changing was the first one" — $13M from nothing hits differently than $1.5B17:46 — Why pest control? A starving college student, a friend who made $25K in a summer, and zero sales for five days straight21:16 — His boss's question that changed everything: "What on earth would you go work for somebody else?"27:31 — Fifth grade through eleventh grade: watching his family nearly lose the house, the fear that built everything36:35 — Flying his dying father on a private jet from New Orleans to Cedars-Sinai at 2am39:36 — What he wants to be remembered for: "The sign of a good leader is not how many followers you have, but how many leaders you create"Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
• 
  How Anne Mahlum Spends $200k/month with a $115M Net Worth 16.06.2026 47min

  She sold for $88M, almost bought a lake house she didn't want, and spent $340K on Knicks playoff tickets — then gave two away because it felt better.We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.Also, this podcast is made by Hampton, which is a community for founders doing on average $20M a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "Why not, let's make it public." If you are a founder, apply here: https://joinhampton.com/mwAnne Mahlum built Solid Core from $175,000 of her own savings into an $88M exit. Two years later, her net worth is $115–120M, with $65M in public equities and $15M in a single stock alone. But the numbers are the least interesting thing that's happened since.After the sale, she secretly launched a second fitness company, had panic attacks she's never talked publicly about, shut the whole thing down, and spent two years in legal fallout. Then she had a baby, pulled an accepted lake house offer the morning after making it, and started forcing herself to spend $200K a month just to stop the money from piling up.This episode covers the full portfolio breakdown two years post-exit, why she's done with private investments, the Ambition story she's never told, what a baby did to how she thinks about money and time, and what she actually wants to be remembered for — which has nothing to do with net worth.Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
• 
  He Studied 38,000 Twins and Says Your Money Habits Are Genetic 09.06.2026 53min

  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-wrEPISODE DETAILS:Most founders spend years learning how to make money. Almost none of them prepare for what their brain does once they have it.Henrik Cronqvist is a behavioral finance professor who trained under Nobel laureate Richard Thaler and has spent 25 years studying exactly that. His research has been cited over 7,000 times. He has studied 38,000 people to answer one uncomfortable question: how much of the way you save, spend, and invest is actually hardwired into your DNA?The answer will change how you think about every financial decision you make after an exit.This episode covers the science behind why the traits that made you a great founder may work against you as an investor, what actually happens in your brain the day the wire hits, and the one thing Henrik says every founder should do before making a single investment.TIMESTAMPS:00:00 — The traits that made you a great founder will make you a bad investor 01:45 — What is behavioral finance and why should founders care 04:35 — How Henrik got into this research (the Stockholm subway story) 06:39 — The 38,000 twin study: how much of your money behavior is genetic 10:56 — The first thing to do when the wire hits your account 12:49 — Loss aversion, performance chasing, and home bias explained 20:35 — Your personal mortgage predicts how you'll run your company's finances 30:08 — Why your brokerage app is designed to work against you 37:07 — Why founders feel depressed after selling (the science behind post-exit emotions) 47:14 — "I think I'm the exception" — and what the data actually says about that
• 
  He Sold For $8M and Regrets It, And The Reason Why Is Shocking. 02.06.2026 56min

  Please answer our short Moneywise listener survey! (Very, very short): joinhampton.com/moneywisefeedbackJOIN 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-wrEPISODE 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 roadmap08:08 — The $10M deal unpacked: earn-out structure, revenue milestones, and what he actually collected10:17 — The co-founder split, the 25% influencer equity deal, and whether he'd do it again14:09 — How the influencer partnership worked and why they replicated it on Tapio26:17 — "Getting a ton of money up front feels unhealthy" — Thibault on why lump-sum exits are psychologically dangerous28:14 — The "frozen state": why founders can't ship after a big exit30:42 — The earn-out burnout period: stress, loss aversion, and the 18 hardest months of his life34:37 — "It was a bad decision financially" — Thibault's verdict on the sale38:15 — Nomadic life, the Vietnam hacker residency, and how wealth changes how he travels42:42 — No financial advisor, no trust in wealth managers — why everything goes into S&P 50045:29 — Personal spend breakdown: ~$8K/month — rent, food, tech gadgets, and that's basically it48:27 — What happens to the ~$90K/month delta: cash, S&P 500, and acquiring more products49:45 — The portfolio strategy: five products, two unannounced, and the 2026 scaling challenge51:12 — Building a distribution bridge between all his products with an AI agent53:06 — Raising kids with money: unconditional safety as the foundation for risk-taking
• 
  How To Raise Great Kids When You’re Rich 20.05.2026 35min

  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-wrTHIS 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 makeCHAPTERS:00:00 The 16-year-old in the airport02:57 Frustration tolerance is the most important life skill05:30 Why wealthy kids have 2-3x higher anxiety and depression08:00 Monkey see, monkey do: the emulation problem11:00 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 will21:00 Why allowance only works if money is finite25:00 The Scarsdale busboy who sees $300 sweatshirts as 30 hours of work28:00 Scott Galloway's moving goalpost30:17 The presence problem (the hardest one for me)33:00 The 5 rules I'm taking with meREFERENCED 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 afterABOUT 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 12.05.2026 34min

  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 18How a Minecraft addiction became his first real businessLeaving a six-figure BCG career to bet on himselfBuilding a $1M ARR agency in under a year with 1,000 newsletter subscribersHis actual net worth, his $10M target, and why he keeps almost no cashWhy he thinks the wealthiest people he knows are often the least happyTimestamps00:00 - Cold open00:58 - Introducing Nathan May01:23 - Small talk / how Nathan starts his day02:32 - The agency, the numbers, how life has changed03:24 - Growing up poor in Ohio — never left the state until 1805:35 - He originally wanted to be an actor06:04 - The Minecraft business: how a video game addiction made him $100K at 1509:05 - Wharton, Wall Street culture shock, and the path to BCG10:36 - What BCG actually changed about his life12:01 - Building the agency: newsletters, Schwarzenegger, and why it felt like video games again15:32 - His real relationship with money: checking account, savings, leverage strategy16:52 - The $10M number: how he used ChatGPT to find his "enough"18:34 - The Media Mafia: seven founders, one office, a monthly revenue leaderboard20:31 - Being at the cusp — exciting, terrifying, or both?23:07 - Why IRL community is the highest-leverage thing a founder can build26:03 - What Hampton means to him27:31 - His mom's passing, the $1M milestone, and why none of it felt like anything29:24 - Can you be successful without community?31:39 - What's next and closing thoughtsMoneyWise 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 05.05.2026 57min

  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 GoodmanJon 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.comOceans - 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? 28.04.2026 37min

  Chapter Timestamps00:00 — 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 likeAt 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 $100MThe emotional moment the wire hit at the Western Wall, and the tragedy that hit the same dayHis 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 fundingWhy he over-indexes on life and health insurance — and the advice he gives every founderThe 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 politicsWhat he'd do differently if he could rewind 15 yearsThe 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.comOceans - 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 Has $70M And Thinks Financial Advisors Are a Waste of Money 21.04.2026 51min

  John Arrow bootstrapped Mutual Mobile from a $0.99 iPhone app to a 350-person company — with zero investors — and sold it twice. In this episode of MoneyWise, John breaks down exactly how he built and exited one of Austin's most successful tech companies, what he did with the money, and what his financial life actually looks like today.John gets radically transparent about his net worth (well into 8 figures), his monthly spending ($50–65K/month), his investment strategy, and why he thinks most wealth managers are a waste of money.Plus: the illegal Cuba trip right before signing a life-changing deal, the $500K bet to hack Apple's encryption, how he sued American Express on behalf of a friend and won in 48 hours, and the new AI company he built the morning of this recording.Topics covered:How John made his first $1,000/day at 14 years oldBootstrapping Mutual Mobile to a $70M exit with no outside fundingWhat actually happens the day a wire hits your accountWhy he sold the company a second time — and for how muchHis exact portfolio breakdown (stocks, private investments, real estate)Why he never drinks (the real reason)FreedomGPT and the future of uncensored AIHow to think about money once you never have to work againStop 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: https://www.joinhampton.com Sponsors:Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comOceans - 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.
• 
  This 23-Year-Old Dropout Bootstrapped His Company to Millions 14.04.2026 36min

  Josh Suggs is 23 years old and already running a company generating millions in revenue, completely bootstrapped. But the money story here isn't just about the numbers. It's about a kid who grew up in Westport, CT, one of the wealthiest zip codes in America, feeling like he didn't belong, watching his mom stress about retirement while surrounded by hedge fund dads, and channeling that into an obsession with building things from the age of 13.Daniel and Josh get into the real numbers: what Josh actually takes home, where it sits (mostly cash, barely invested, and he'll tell you why), and what his monthly spend actually looks like living in New York. Spoiler: $3,000/month on Uber because he refuses to take the subway.ABOUT MONEYWISEMoneyWise is a Hampton podcast about what wealthy founders actually do with their money. Not how they made it — what they do after. Real numbers. Real allocation. Real feelings about wealth. Hosted by Daniel Berk.New episodes in production now.____________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: https://www.joinhampton.com This episode's sponsor is Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com