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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-wr Why 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. His dad died with $133,000. Now he’s worth $35 million, and his life is optimized for moments of financial generosity. Adam Katz is a wealth advisor to venture-backed founders who’s as rich as the people he advises. His dad was a guidance counselor in the Bronx who made $48,000 after 31 years and died with $133,000. Adam didn’t board a plane until he was 16. He cold-called his way into Merrill Lynch, left to start a multifamily office, sold it to one of the largest non-bank wealth managers in the world, and now sits on a net worth somewhere between $25M and $50M. He asked his kids to guess the number. One said $8M. The other said $75M. This episode gets into exactly where that money sits (75% illiquid, 30 K-1s, 20% in cash on purpose), the mortgage move he and most of his clients use to deduct every dollar of interest, and a full walkthrough of his $1M annual spend: $300K on vacations, $150K in donations, $100K at restaurants with $35K of it in tips. He explains his tipping system, why he tipped $2,000 on a $3,000 bill, the $33K mattress, the $200K watch, and the “three-digit rule” that reshaped how I think about giving. Also, this podcast is made by Hampton, which is 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 are a founder, apply here: http://joinhampton.com/mw Timestamps:00:00 — Cold open: a dad who died with $133K, a son worth $35M, and two kids who guessed $8M and $75M01:16 — What Adam does and why a wealth advisor is as wealthy as his clients02:31 — Growing up in the Bronx: “I used to think luxury for an automobile was a headrest in the back”04:43 — First plane at 16, first time his feet touched sand at 2405:17 — Cold-calling the white pages into Merrill Lynch: a $50K job vs. his dad’s $48K after 31 years08:37 — Leaving Merrill, building a multifamily office, and selling it09:53 — “Raising kids in a Zillow world”: the $125K safari and the net worth guessing game11:40 — The balance sheet: 75% illiquid, 60–65% equities, 10% private credit, 30 K-1s14:16 — Why he’s sitting on 20% cash and spends all $1M of his after-tax income every year16:33 — The mortgage move: buy with cash, take the loan after, deduct 100% of the interest19:28 — “You’re either going to get paid on time or over time”: how he picks private credit22:23 — Vacations as a line item, and why you have to explain your why24:00 — The whole family flies first class, and the three-digit rule26:30 — 6 to 8 trips a year, $250–300K: South Africa, Iceland, Galapagos, Thailand29:00 — He reads the last page of his book: the scarcity seesaw31:37 — $100K at restaurants this year, $35K of it in tips33:24 — The tipping system: $25 breakfast, $50 lunch, $100 dinner, only 20s and 100s in his pocket35:27 — The $33K mattress and $100 to each delivery guy: “If I don’t know what I have in my pocket, I don’t have the right to keep it there”37:00 — A $2,000 tip on a $3,000 bill38:06 — $400–500K donated, renovating the synagogue, and 1,000 people asked to stand40:20 — The $37K all-inclusive and the $250-a-day tip epiphany42:00 — 13 years on an Apple Watch, the Rolex his wife chased for nine months, the $200K “house watch”47:23 — The full annual spend: mortgages, taxes, vacations, food, donations, shopping, $45K liability insurance50:43 — The Alpina green BMW and the bell curve of consumption52:13 — Die with $600M or $800M? “I don’t meet anyone that actually cares”53:06 — The legacy plan, the roach apartment, and being “supportive, not overly enabling”54:35 — Threshold number: $20–25M throwing off $1M a year57:28 — Daniel’s takeaway: the three-digit rule works at $20 too Sponsors:Silvia, your personal AI CFO. Bring your investments, cash, property, and debt into one view and get answers built around your finances, your family, and creating generational wealth. https://www.cfosilvia.com/moneywiseDaily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search “Moneywise Hampton”]

Nearly half of 250 founders pay someone on their team more than they pay themselves. 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-wr Why 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. In late August 2026, Hampton anonymously surveyed 250 founders and CEOs about what they actually take home. Founder salaries turn out to look pretty normal even when the companies don't: about $150K below $10M in revenue and about $400K at $30–50M. Fifteen founders reported a $0 salary, and six of those took at least $500K on top of it. Daniel walks through the split between bootstrapped and venture-backed founders, where 39% of bootstrapped founders took $500K+ in additional compensation and not one venture-backed founder reported more than $300K. He covers the IRS rules that make the "tiny salary, big distributions" advice risky, the compensation that never shows up on payroll (credit card points, vehicles, real estate), and what senior teams get paid. The episode closes on why being personally broke changes the decisions you make for your company, plus a three-question exercise to check your own pay. 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/mw Timestamps:00:00 — Founders know their revenue cold and go quiet about take-home, so Hampton asked 250 of them anonymously00:42 — How to read the data: 296 records, 250 complete, answers in ranges, and who qualifies for Hampton02:03 — Founder salaries stay "normal": about $150K under $10M in revenue, about $400K at $30–50M02:25 — About 47% pay at least one functional leader more than their own base salary03:12 — The "founder discount" research, and Josh Payne's climb from $0 to $250K before selling StackCommerce for about $80M04:12 — 15 founders report a $0 salary, and six of them take $500K+ in additional compensation04:50 — Bootstrapped vs. venture-backed: 39% of bootstrapped founders at $500K+, zero VC-backed founders above $300K05:47 — What VC-backed CEOs earn by stage: "the paycheck is really only half the bet"06:40 — Why "tiny salary, big distributions" is bad advice, and the accountant who paid himself $24K and lost to the IRS07:55 — How a low salary caps your retirement contributions: "boring is really good when the alternative is explaining your creativity to the IRS"08:52 — The comp nobody counts: a third of founders mention credit card points, plus vehicles and real estate10:15 — Senior team pay: sales leaders earn the most, HR the least10:43 — Company-wide bonuses: 5% of companies under $1M in revenue, 44% above it11:08 — "Equity isn't a coupon code for underpaying someone," and what happens when employees see coworkers' salaries12:35 — What are you optimizing for? "I own a lot of equity" is not the same as "I am financially secure"13:38 — The sugarcane farmer study on money stress, and Andrew Wilkinson's case for paying yourself well early14:43 — The exercise: add up everything you took last year, then ask three questions Sponsors: - Silvia, your personal AI CFO. Bring your investments, cash, property, and debt into one view and get answers built around your finances, your family, and creating generational wealth. https://www.cfosilvia.com/moneywise- Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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 took a company public at 23, lost a $65M poker business in one day, and now spends $110K a month on a private zoo. Dan Fleyshman started selling baseball cards at an LA swap meet at four years old while his parents sold Levi's out of a van. At 17 he snuck into a Vegas trade show with $5 vending-machine business cards and wrote $1M in orders. At 23 he took his energy drink company public. Then the government shut down online poker in 2011 and his $65M poker site was gone in a day. Today he runs Elevator Studio, has raised $56M for 18 companies through a 2,214-person syndicate, holds 43 angel investments, and puts his net worth north of $50M. This episode gets into how Dan actually makes money: the 20% carry, trading agency services for equity, and why only 3 of his 18 syndicate deals have failed. He walks through the $6.6M ranch with a lake, a wedding venue that has never hosted a wedding, and 208 rescue animals. He explains why he rents both of his homes, flies Southwest while spending over $1M a year on travel, and refuses to slow down as a new dad. He closes with the list of 39 names in his phone that explains all of it. 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/mw Timestamps:00:00 — Selling baseball cards at four years old at an LA swap meet while his parents sold Levi's out of a van01:58 — A family of four on $24K a year, sleeping on a couch, and turning his mom's $13 into $30 of candy sales04:00 — Three jobs at 15, $43K saved for college, and spending all of it on a clothing brand instead04:40 — Sneaking into the MAGIC convention at 17 with $5 business cards and writing $1M in orders next to Sean John and FUBU06:47 — Going public at 23: two years, $2M, and "you literally hire an auditor to audit your auditor"10:31 — Daniel asks for the net worth number and Dan starts working it out live11:00 — $56M raised across 18 companies, a 20% carry, and only three failures12:25 — How Elevator Studio works: 3,500 influencers and trading services for equity14:01 — Personal checks of $25K to $250K, and why he charges his 2,214 syndicate investors no management fee16:37 — The $6.6M ranch, the $1.5M lake, 208 animals, and $110,250 a month in overhead: "I've never done a wedding"18:43 — Why he rents both of his homes, plus the $500K Everbowl check that went from 13 locations to 10420:08 — Joyride candy, Cards and Coffee with Gary Vee and Steve Aoki, and $28M in small business loans22:50 — The day online poker shut down and his $65M company disappeared: "diversify with investments, not with attention"24:47 — "If you were under oath": Dan puts a floor on his net worth28:15 — High-stakes cash games, charity tournaments, and why he still plays29:35 — Cards and Coffee revenue drops from $12M+ to $6M, and the $250K-a-year security guard31:17 — 250 travel days a year, private 20 to 30% of the time, Southwest the rest33:02 — Charging for a private jet in his speaking fee, then flying JetBlue and keeping the difference36:04 — His daughter joined a mastermind call on her first day alive, and why he won't pretend he's slowing down38:48 — The 39 people he's lost and the list he keeps in his phone Sponsors: - Silvia, your personal AI CFO. Bring your investments, cash, property, and debt into one view and get answers built around your finances, your family, and creating generational wealth. https://www.cfosilvia.com/moneywise- Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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 took a second mortgage to keep WatchMojo alive. Today he's worth over $100M and is trying to buy a baseball team. Ashkan Karbasfrooshan is the founder and CEO of WatchMojo, one of the largest media companies ever built on YouTube. He started it in 2006 with a $282,500 check from the AskMen sale, racked up roughly $1M in losses by 2011, sold his retirement savings, took a second mortgage, and paid himself $32,000 a year for the first five years. Then the top-10 format hit, revenue went from $1M to $10M+ in a few years with EBITDA margins as high as 80%, and he turned down offers at $75M, $80M, and $90M valuations. In 2020 he sold 25% to Star Mountain Capital at a $90M CAD valuation. He still owns most of the company, and puts his net worth between $100M and $250M. This episode gets into what it's like to sign a second mortgage at a notary with no idea if you'll end up homeless, why he moved payroll to twice a month just to have two fewer panic attacks a year, the real reason he walked away from an $80M offer (it wasn't greed), and how saying yes to everything cut his EBITDA in half. We also go deep on how he actually invests now — $5M across 15 startups, two-thirds of his stock portfolio self-managed — why he still takes the $40-cheaper flight, and his current mission to bring the Montreal Expos back to MLB. 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/mw Timestamps:00:00 — Ash's background: born in Iran, raised in Montreal, and why "the self-made man is a myth"02:50 — 31 jobs and the reluctant entrepreneur: "Wall Street is not rolling out the carpet for anybody named Ashkan"07:03 — The AskMen exit: a $282,500 check at 27, plus ~$150K when News Corp bought IGN09:18 — Why he bet on YouTube in 2006: "You don't go to war with the army you want, you go to war with the army you have"14:23 — The dark years: $1M in losses, selling his RRSPs, and the second mortgage16:14 — "I made payroll twice a month instead of every two weeks because I wanted 24 anxiety incidences, not 26"18:24 — Being early vs. being too early (and the Quibi problem)20:37 — The hockey stick: $1M → $3M → $5M → $10M revenue, 67-80% EBITDA margins23:25 — Paying himself $32K a year for the first five years24:59 — The 2012 offer he almost took ($3.5M + earn-out) and why he was relieved it fell through28:32 — Turning down $75M, $80M, and $90M valuations in 201730:36 — "I was like a drunk sailor at a bar saying yes to everything" — EBITDA falls by half31:39 — Why walking away wasn't greed: the call-option trap he saw coming32:58 — The 2020 deal: selling 25% to Star Mountain Capital at $90M CAD37:54 — Net worth reveal: "anywhere from 100 to 250 million"39:03 — Monthly spend, paying off the house, and $5M into 15 startups43:37 — Was the deal life-changing? "More mindset changing than life changing"44:34 — What he never shares about money45:34 — The Montreal Expos comeback plan: "It's not impossible, it's improbable" Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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 $42M, lost a $70M deal to a war, and sold his company over WhatsApp instead. Ryan Levesque is the author of the #1 national bestseller Ask and the founder of the Ask Method Company, a seven-time Inc. 5000 business that did over $100M in revenue. He grew up blue collar, quit AIG in China the morning the Wall Street Journal said the company was going bankrupt, and built his first business selling Scrabble tile jewelry tutorials on Etsy. Then he tried to sell his company twice. The first buyer flipped a $42.5M deal to $17M at the eleventh hour. The second, a $70M offer, evaporated the week Russia invaded Ukraine. Today he sits on $30–35M in liquid net worth and runs a 150-acre farm in Vermont with his wife and two boys, where 80% of what his family eats comes off their own land. This is the longest Moneywise episode we've ever cut, and I barely interrupted. We go deep on the two failed exits, the life insurance rejection letter at age 30 that turned out to be organ failure, the photo of his sons that made him stop chasing the number, and what it actually costs to run a 150-acre farm (spoiler: free food runs about half a million a year). Ryan also breaks down the money curriculum he built for his kids, why $35M didn't feel like enough until he decided it was, and the honeybee epiphany that led to selling his company to his biggest competitor. 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/mw Timestamps:0:00 — "Mr. Levesque, you should be in a coma right now." Cold open and episode roadmap5:30 — The WSJ headline reads "AIG to file for bankruptcy." He resigns the same day with ~$100K in the bank9:56 — Reverse-engineering an Etsy seller's income and building a Scrabble tile jewelry tutorial business: "emulate before you innovate"12:32 — The crash of the Scrabble tile jewelry market. Lesson: pick evergreen markets14:29 — Dead orchids in Shanghai become a $500K/year business. Then 23 businesses at once17:19 — A nine-figure sale to NBC (Golf Pass) and a $168M sale to PayPal. His cut: "less than seven figures"19:00 — Ask becomes the #1 bestselling book in America and births a $100M+ company21:00 — The $42.5M deal gets flipped to $17M at the eleventh hour. "We basically gave them the middle finger"25:13 — Interviewing 12 investment banks, going back to market, and landing a $70M offer28:30 — Russia invades Ukraine. The deal, and the entire M&A market, evaporates33:23 — The life insurance rejection letter. Kidney failure. Ten days in ICU. Undiagnosed type 1 diabetic40:16 — "My kid can't grow up without a dad." Shutting down 23 businesses41:42 — Two photos of his boys, seven years apart. "It was like a heartbeat"43:00 — Texting his wife from a tent in Vermont. Full-price cash offer on the Austin house the same night49:13 — Reading Peter Lynch at age 10 and turning $5K into $100K+ by 1851:57 — What he looked for in land: top of watershed, no PFAS, good schools. 12 months of Airbnbs56:41 — 48 beehives, 1,000 maple taps, 500 fruit trees, seven freezers. 100% of their own protein58:40 — The farm numbers: just under $5M for the land, $2M mortgage at 6.5%, $220K/year before a single animal1:03:59 — $260K in year one, $175K/year after. "Free food costs a lot of money"1:06:28 — The kids' money curriculum: Rich Dad Poor Dad read-alouds, Greenlight accounts, a real estate syndication paying them $300–400/month1:11:20 — His net worth when he decided it was enough: $30–35M liquid1:12:47 — "I've never been less money motivated in my life." $1M webinars and the Mexican fisherman1:15:08 — Goldenrod, purple aster, and the WhatsApp voice memo to Daniel Priestley. Company sold three months later1:20:20 — Legacy, $120K/year in tuition, and how much to hand to your kids: "the brownies are not fully baked"1:25:39 — Seven weeks in Europe, giving back, and why all altruism is selfish1:31:36 — Daniel's takeaway: figure out what you're optimizing for and start living it now Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Timestamps: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 resolution Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Timestamps: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 model Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Timestamps:  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.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Timestamps: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 history Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Episodes 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-nLk Timestamps: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: Hampton Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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-wr Why 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/mw Timestamps: 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 Ampush 02:00 — The Facebook arbitrage that changed everything: $100K/month in June 2010 to $2M in revenue and $600K in EBITDA fourteen months later 02:49 — "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 house 07:30 — The made-up number that wrecked them: hoping for $150M, getting $60–75M offers, and turning down $190M in Marin stock 09:24 — 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 deal 13:12 — 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 it 17:52 — Gateway X by the numbers 19:06 — Whether the scarcity ever goes away: "nine days out of ten" became "one day out of ten," and the coach question he couldn't answer 20:16 — The Deer Valley condo, and finally understanding why people buy vacation homes 21:08 — Full portfolio breakdown and why he tells his advisors to mark his startup equity at zero 23:24 — 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 vacation 28:16 — 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, give 30:19 — Running a Starbucks P&L with his 9-year-old daughter in the store 32:30 — The four-bucket framework: spend it, give it to the government, give it to charity, or give it to your kids 34:44 — 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 funeral Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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/mw Craig 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.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

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/mw Michael 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.com Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]