Moneywise

The Biltmore: The Vanderbilt Fortune & America's Largest Mansion

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. The youngest Vanderbilt got the smallest inheritance, built the biggest house in America, and died with $11,000 in stocks. George Vanderbilt was the youngest of eight kids in the richest family in America. His brothers inherited about $65 million each. He got $10 million, then spent somewhere between a third and half of it building the Biltmore: 250 rooms, 125,000 acres, 80 servants, electricity before almost anyone had it, and a forestry program that outspent the U.S. Department of Agriculture. He outspent his income every year, dipped into principal to cover it, and when he died at 51 his personal estate came to about $900,000. His widow sold 86,000 acres to the government for $5 an acre to keep the house standing. This episode is the full financial autopsy of the Biltmore. What it cost to build (and why inflation math gets it wrong), what it cost to run, how the family sold off piece after piece just to hold onto the house, and how a grandson who quit banking turned a money pit into a business that now pulls in 1.4 million visitors a year. Along the way, Moneywise guests like Hank and Neil Patel show up with their own versions of the Biltmore problem. It ends with three numbers to run before you buy any house. 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 richest man in America dies; his youngest son gets the smallest check and builds the biggest house 01:14 — What this episode is about, and why the Biltmore problem is still alive in Hampton today 01:55 — Cornelius Vanderbilt, “which is a sick name,” and a $200 million fortune (roughly $6–7 billion today) 02:37 — George the bookworm secretly buys 700 parcels, 50 farms, five cemeteries, and an entire town 03:29 — The architect of the family and the designer of Central Park draw up a French castle in the Blue Ridge 04:12 — No roads, so he builds a private railroad, a brick kiln, and a woodworking factory from scratch 04:56 — Electricity, an Otis elevator, a 70,000-gallon pool, and a bowling alley: “like a spaceship” in 1895 05:41 — 250 rooms, 33 years old, single 06:02 — What it actually cost, and why “$200 million today” is the wrong number (try $9 billion) 07:16 — His brothers spent the same on summer houses they used a few weeks a year 07:53 — Why building the house was the cheapest part: 80 servants and outspending a federal department 09:01 — The estate was supposed to pay for itself; it never did 09:16 — Hank’s 24,000 sq ft house: “we looked at each other like, what did we just do?” 10:00 — Marriage, a canceled Titanic ticket, and death at 51 with $11,000 in stocks and bonds 10:59 — Edith sells 86,000 acres for $5 an acre; 125,000 acres shrinks to 8,000 11:36 — The question nobody in George’s life asked him 12:12 — The Depression forces the doors open at $2 a ticket; WWII hides the National Gallery inside 12:39 — A grandson quits banking in 1960 and runs the house like a business: 64,000 visitors to 1.4 million 13:30 — Still private, still family-owned, assessed at $157 million 13:54 — Was George an idiot? Shirtsleeves to shirtsleeves and the Vanderbilt reunion with zero millionaires 14:53 — “The house isn’t the mistake. The house that only costs money is the mistake.” 15:09 — Three numbers to run tonight before you buy or build a house 16:06 — Hank and Neil Patel both downsized, and both see their kids more 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 Subscribe to Moneywise: / @themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search “Moneywise Hampton”]

$30M Net Worth, $8M Compound: “Owning Is Financially Dumb”

How This Wealth Advisor Spends $1M/Year ($300K on Vacations)

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 $75M 01:16 — What Adam does and why a wealth advisor is as wealthy as his clients 02:31 — 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 24 05:17 — Cold-calling the white pages into Merrill Lynch: a $50K job vs. his dad’s $48K after 31 years 08:37 — Leaving Merrill, building a multifamily office, and selling it 09:53 — “Raising kids in a Zillow world”: the $125K safari and the net worth guessing game 11:40 — The balance sheet: 75% illiquid, 60–65% equities, 10% private credit, 30 K-1s 14:16 — Why he’s sitting on 20% cash and spends all $1M of his after-tax income every year 16:33 — The mortgage move: buy with cash, take the loan after, deduct 100% of the interest 19:28 — “You’re either going to get paid on time or over time”: how he picks private credit 22:23 — Vacations as a line item, and why you have to explain your why 24:00 — The whole family flies first class, and the three-digit rule 26:30 — 6 to 8 trips a year, $250–300K: South Africa, Iceland, Galapagos, Thailand 29:00 — He reads the last page of his book: the scarcity seesaw 31:37 — $100K at restaurants this year, $35K of it in tips 33:24 — The tipping system: $25 breakfast, $50 lunch, $100 dinner, only 20s and 100s in his pocket 35:27 — 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 bill 38:06 — $400–500K donated, renovating the synagogue, and 1,000 people asked to stand 40:20 — The $37K all-inclusive and the $250-a-day tip epiphany 42:00 — 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 insurance 50:43 — The Alpina green BMW and the bell curve of consumption 52:13 — 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 year 57:28 — 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/moneywise 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”]

250 CEOs Confessed Their Pay. Half Earn Less Than Employees (Research Backed)

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 anonymously 00:42 — How to read the data: 296 records, 250 complete, answers in ranges, and who qualifies for Hampton 02:03 — Founder salaries stay "normal": about $150K under $10M in revenue, about $400K at $30–50M 02:25 — About 47% pay at least one functional leader more than their own base salary 03:12 — The "founder discount" research, and Josh Payne's climb from $0 to $250K before selling StackCommerce for about $80M 04:12 — 15 founders report a $0 salary, and six of them take $500K+ in additional compensation 04:50 — Bootstrapped vs. venture-backed: 39% of bootstrapped founders at $500K+, zero VC-backed founders above $300K 05:47 — 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 IRS 07:55 — 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 estate 10:15 — Senior team pay: sales leaders earn the most, HR the least 10:43 — Company-wide bonuses: 5% of companies under $1M in revenue, 44% above it 11:08 — "Equity isn't a coupon code for underpaying someone," and what happens when employees see coworkers' salaries 12:35 — 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 early 14:43 — 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/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

He's Worth $50M and Spends $110K a Month on a Zoo That Makes $0

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 van 01:58 — A family of four on $24K a year, sleeping on a couch, and turning his mom's $13 into $30 of candy sales 04:00 — Three jobs at 15, $43K saved for college, and spending all of it on a clothing brand instead 04:40 — Sneaking into the MAGIC convention at 17 with $5 business cards and writing $1M in orders next to Sean John and FUBU 06:47 — 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 live 11:00 — $56M raised across 18 companies, a 20% carry, and only three failures 12:25 — How Elevator Studio works: 3,500 influencers and trading services for equity 14:01 — Personal checks of $25K to $250K, and why he charges his 2,214 syndicate investors no management fee 16:37 — 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 104 20:08 — Joyride candy, Cards and Coffee with Gary Vee and Steve Aoki, and $28M in small business loans 22:50 — 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 worth 28:15 — High-stakes cash games, charity tournaments, and why he still plays 29:35 — Cards and Coffee revenue drops from $12M+ to $6M, and the $250K-a-year security guard 31:17 — 250 travel days a year, private 20 to 30% of the time, Southwest the rest 33:02 — Charging for a private jet in his speaking fee, then flying JetBlue and keeping the difference 36:04 — His daughter joined a mastermind call on her first day alive, and why he won't pretend he's slowing down 38:48 — 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/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

This Guy Built a $90M Company on YouTube in 2006

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 IGN 09:18 — 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 mortgage 16:14 — "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 margins 23:25 — Paying himself $32K a year for the first five years 24:59 — The 2012 offer he almost took ($3.5M + earn-out) and why he was relieved it fell through 28:32 — Turning down $75M, $80M, and $90M valuations in 2017 30:36 — "I was like a drunk sailor at a bar saying yes to everything" — EBITDA falls by half 31:39 — Why walking away wasn't greed: the call-option trap he saw coming 32:58 — The 2020 deal: selling 25% to Star Mountain Capital at $90M CAD 37:54 — Net worth reveal: "anywhere from 100 to 250 million" 39:03 — Monthly spend, paying off the house, and $5M into 15 startups 43:37 — Was the deal life-changing? "More mindset changing than life changing" 44:34 — What he never shares about money 45:34 — 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/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

He Said $35M Was Enough, Then Moved His Family to a 150-Acre Farm (Ryan Levesque)

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 roadmap 5:30 — The WSJ headline reads "AIG to file for bankruptcy." He resigns the same day with ~$100K in the bank 9:56 — 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 markets 14:29 — Dead orchids in Shanghai become a $500K/year business. Then 23 businesses at once 17:19 — 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+ company 21:00 — 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 offer 28:30 — Russia invades Ukraine. The deal, and the entire M&A market, evaporates 33:23 — The life insurance rejection letter. Kidney failure. Ten days in ICU. Undiagnosed type 1 diabetic 40:16 — "My kid can't grow up without a dad." Shutting down 23 businesses 41:42 — 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 night 49:13 — Reading Peter Lynch at age 10 and turning $5K into $100K+ by 18 51:57 — What he looked for in land: top of watershed, no PFAS, good schools. 12 months of Airbnbs 56:41 — 48 beehives, 1,000 maple taps, 500 fruit trees, seven freezers. 100% of their own protein 58:40 — The farm numbers: just under $5M for the land, $2M mortgage at 6.5%, $220K/year before a single animal 1:03:59 — $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/month 1:11:20 — His net worth when he decided it was enough: $30–35M liquid 1:12:47 — "I've never been less money motivated in my life." $1M webinars and the Mexican fisherman 1:15:08 — Goldenrod, purple aster, and the WhatsApp voice memo to Daniel Priestley. Company sold three months later 1:20:20 — 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 selfish 1:31:36 — 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/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

I Asked 40 Millionaires Their Biggest Regret

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 random 01:02 — Every regret collapses into three buckets 01:24 — Regret vs. disappointment: why regret needs an alternate reality 02:25 — The brain science: patients with orbitofrontal damage don't feel regret 03:14 — Your brain uses regret to change future decisions before you make them 04:02 — 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 medalists 06:27 — 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 agency 08:25 — 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 closure 10:26 — "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 it 13:04 — The 23-year-old already in the "never enough stage," and the moving goalposts from $10M to $1B 13:56 — Bucket 3: "I thought I had more time" — kids, health, and the $80M founder who hit rock bottom 14:52 — 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 found 17:21 — The Harvard study: relationships at 50 predicted health at 80 better than cholesterol 19:45 — The Regret Test: three questions to ask about your biggest regret 20:44 — "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/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

Patrick & Kathy Terry (P. Terry's): "Why We Said No to $100M"

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% raise 06:33 — Patrick's path: Kool-Aid stand at 5, ad agency by day, running a pizza place nights and weekends 09:30 — 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 depreciation 16:09 — The 2016 "dog and pony show": realizing for the first time what the business was worth 17:35 — "It was between 70 and $100 million" — a 10–12x offer, and why they turned it down 20:23 — 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 90 24:27 — 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 taken 27:17 — The June EOT transition: gifting and selling the first ~11% to the trust via a seller's note 33:36 — The origin of interest-free loans: Vinny's broken truck and $150 34:05 — $900K loaned to hourly employees over 20 years — only $5,000 ever defaulted 37:14 — The Maggie rule: every decision tested against the woman who's worked the grill for 21 years 42:05 — Kathy explains EOT vs. ESOP — and why one protects the culture forever 49:40 — Profit sharing starts next year: 5% of EBITDA now, 20% in five years, based purely on tenure 54:49 — "The island sucks. This is okay." What Patrick learned about what he actually wanted 59:20 — 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/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

He Ran PayPal With Elon. Now He Has $100M and Spends Nothing

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"]