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Moneywise: Daily Summaries Delivered
by Hampton
This is Moneywise, a podcast where host Daniel Berk is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
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- 2 days ago46 min
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-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He 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/mwTimestamps: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 phoneSponsors: - 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.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- 1 weeks ago54 min
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-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He 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/mwTimestamps: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.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- 2 weeks ago1h 34m
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-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He turned down $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/mwTimestamps: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 nowSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/dani
- 3 weeks ago22 min
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-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.I asked 40 millionaires their biggest regret. One answer was just two words: "withholding love."This episode started with a simple survey: 40 millionaires, one question — what's your biggest regret? The answers ranged from $22K a year dumped into life insurance instead of Bitcoin ($11M of upside gone) to hundreds of bitcoins sold at $300 to make payroll. But cross-referenced against 100+ Moneywise conversations, every answer collapsed into just three regrets: I can see the life I almost had. I didn't become the person I thought I could become. I thought I had more time.Then it gets into the science. Why bronze medalists look happier than silver medalists. Why finance is only 2.5% of most people's regrets but dominated this survey. Why the person you never became can bother you longer than any mistake you actually made. Why an $80M exit sent one founder to rock bottom. And a three-question Regret Test to figure out whether your regret is still useful — or just expensive entertainment.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — The survey: 40 millionaires, one question, and the answers that looked completely random01:02 — Every regret collapses into three buckets01:24 — Regret vs. disappointment: why regret needs an alternate reality02:25 — The brain science: patients with orbitofrontal damage don't feel regret03:14 — Your brain uses regret to change future decisions before you make them04:02 — Bucket 1: "I can see the life I almost had" — "the stock market is basically a regret calculator"05:23 — The Olympic study: why bronze medalists look happier than silver medalists06:27 — Finance is only 2.5% of most people's regrets — so why was this survey drowning in them?07:36 — The Opportunity Principle: agency creates regret, and rich people have had a lot of agency08:25 — Bucket 2: "I didn't become the person I thought I could become"09:08 — Ought self vs. ideal self — and why ideal-self regrets never get closure10:26 — "The unlived version of you never has a bad quarter"11:02 — The famous "you'll regret what you didn't do" stat — and the 2,600-person study that broke it13:04 — The 23-year-old already in the "never enough stage," and the moving goalposts from $10M to $1B13:56 — Bucket 3: "I thought I had more time" — kids, health, and the $80M founder who hit rock bottom14:52 — Why priorities flip when time feels scarce (and Daniel's midlife crisis at 30)16:13 — When to engage with a regret and when to let it go — what the research on older adults found17:21 — The Harvard study: relationships at 50 predicted health at 80 better than cholesterol19:45 — The Regret Test: three questions to ask about your biggest regret20:44 — "Regret in 4K": why money doesn't eliminate regret — it makes it higher resolutionSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- Sep 8, 20261h 0m
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-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.They turned down a $100M offer for their burger stand — now they're giving the company to their 1,800 employees.Patrick and Kathy Terry opened a 500-square-foot burger stand in South Austin in 2005 — three months into their marriage — selling $1.60 hamburgers. Kathy barely took a salary for over a decade. In 2016, with ten locations, a buyer offered them between $70 and $100 million, and they said no, pulling out just under $10M — the only money they've ever taken in 21 years. Today P. Terry's runs 37 locations, employs 1,800 people, does between $150 and $200 million a year growing 20%+ — and instead of selling, they're transferring the whole company to their employees through an Employee Ownership Trust, something fewer than 100 American companies have ever done.This episode gets into the exact numbers behind the offer they walked away from, why $10M felt like enough, the $900K in interest-free loans they've made to hourly employees (with only $5K in defaults), the "Maggie rule" that governs every company decision, and how an EOT actually works versus an ESOP — including why one protects your culture forever and the other can be forced to sell it. It ends with the question underneath it all: what a business is for when the check stops mattering.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — Cold open: "It was between 70 and $100 million and you turned it down."02:53 — Kathy's West Texas upbringing, quitting the law firm, and giving herself a 500% raise06:33 — Patrick's path: Kool-Aid stand at 5, ad agency by day, running a pizza place nights and weekends09:30 — Springing the burger stand idea on Kathy three months into their marriage: "I didn't think he'd ever do it"11:05 — Year one: $600K in revenue from 500 square feet — and still in the red after depreciation16:09 — The 2016 "dog and pony show": realizing for the first time what the business was worth17:35 — "It was between 70 and $100 million" — a 10–12x offer, and why they turned it down20:23 — Kathy's real fear: "Who's going to take care of our employees? They're not going to bake birthday cakes anymore."23:01 — Patrick was stunned to learn they had 300 employees — he thought it was 80 or 9024:27 — Why the birthday cakes matter: "For a lot of our employees, that is how they celebrate their birthday"25:59 — Barely taking a salary for 12 years, then pulling out just under $10M — the only money ever taken27:17 — The June EOT transition: gifting and selling the first ~11% to the trust via a seller's note33:36 — The origin of interest-free loans: Vinny's broken truck and $15034:05 — $900K loaned to hourly employees over 20 years — only $5,000 ever defaulted37:14 — The Maggie rule: every decision tested against the woman who's worked the grill for 21 years42:05 — Kathy explains EOT vs. ESOP — and why one protects the culture forever49:40 — Profit sharing starts next year: 5% of EBITDA now, 20% in five years, based purely on tenure54:49 — "The island sucks. This is okay." What Patrick learned about what he actually wanted59:20 — Kathy's open offer to walk any founder through the EOT modelSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- Sep 1, 202651 min
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-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He co-founded PayPal with Elon Musk, sold Personal Capital for nearly $1B — and spends $70K a year.Bill Harris has a résumé that barely fits on one page. He was CEO of Intuit, founding CEO of PayPal — in the room with Elon Musk, Peter Thiel, and Max Levchin above a bakery near Stanford — and then founded Personal Capital, which he grew to $23 billion in AUM before selling it to Empower Retirement for close to $1 billion. He's done something like that 11 times. Today his net worth is around $100 million, he's 70 years old, and he spends less than $100,000 a year. He sold his houses, cars, airplane, and 31 pets (including two mountain goats and an iguana) and moved into a small cottage near Miami Beach where he bikes to work every day.This episode gets into what $100 million actually looks like when it's spread across public equities and private operating companies — and why the man who built one of the most important wealth management firms in history keeps his own annual spend near $70K. We go deep on the PayPal origin story, what it was like being "theoretically the CEO" in a room full of people whose egos "wouldn't fit in a large gymnasium," and the specific moment Bill realized that his houses, cars, and airplane weren't making him richer in the ways that mattered. He also shares his best piece of investing advice for people in their 30s, his take on why the S&P 500 isn't as diversified as most people think, and what he calls "freedom money."Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps: 00:00 — Cold open: "There wasn't a single one of us whose ego would fit in a large gymnasium" 00:36 — Full guest intro: who Bill Harris is and why this episode matters 03:23 — Bill's origin story: the golden boy path, Intuit CEO at 40, and realizing "I am not a good manager" 06:33 — What money actually is: "It is a rocket fuel. It's the scarce resource you need to build the life you want" 07:38 — The monthly spend reveal: $70–80K a year, all in — "my addiction is Amazon" 09:04 — Life phases: family dole → NYC studio → two houses, 31 pets, and a 1906 Woodside farmhouse 14:20 — Net worth reveal: ~$100M, cut in half by divorce, and the barbell portfolio breakdown 15:27 — Why he doesn't do "fancy investing": survivorship bias, absurd fees, and why alternatives rarely outperform 17:31 — The Evergreen Wealth philosophy: why 80–90% equity is what he'd tell a client with his profile 19:07 — How to value a private company: "Two things dominate it — markets and story" 21:47 — "Things are time": the real cost of owning two houses, four cars, and a small airplane 24:33 — PayPal origin story: "We were close to fisticuffs most days. I was theoretically the CEO" 27:38 — Luck vs. skill: "I'd say it's 80 to 90% luck" — and what that actually means 30:13 — The personal payout from PayPal and Personal Capital: specific numbers, post-tax 32:01 — Why he's self-funding Evergreen with $10M of his own money: "Freedom. I have no boss" 38:05 — Why he still works at 70: mastery, not money — "I can't think of a bigger waste of time" than golf 42:48 — Best investing advice for your 30s: "Hive off a piece and let it marinate" 43:44 — Why the S&P 500 is riskier than it looks: top 10 stocks = 37% of the whole index 45:40 — "Freedom money" defined: the thing that lets you say yes to your own life 48:33 — Closing: "Money is a means to an end. It's not an end."Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast Follow Daniel on X: https://x.com/danielcberk Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- Aug 25, 202648 min
How a $1.5B Wealth Manager Spends His Money
We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He manages $1.5 billion for other people — and still tracks his own spending in a paper checkbook.Glenn Ullmann is a former Air Force pilot who left the military at 29 with a couple hundred thousand dollars, cold-called 200 strangers a day out of a Ponte Vedra phone book, and built Ullmann Wealth Partners into a $1.5 billion RIA that has never had a down year — including 2008. He stopped worrying about money somewhere north of $20 million. Now 63, he spends $30–40K a month, flies his own $1.25M Cirrus, gives more to charity than he can deduct, and still shows up to the office every day.This episode gets into the tension between saving and actually living: why Glenn tells clients with health issues to fly private before their kids do it with the inheritance, how a $10M portfolio pays you $300K a year in "rent" whether markets are up or down, and why he thinks stocks are a bad word. We also cover how he gave up 80% of his own firm to keep his partners, the paper ledger that runs his life, the client who started at $100 a month and now takes the best trips on earth, and why he'd tell a 20-year-old to study English or history instead of finance.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:01:46 — Who Glenn is, what Ullmann Wealth Partners does, and why "returns don't matter if you rear-end Melinda Gates without an umbrella policy"04:16 — Growing up in his grandfather's plastics business, the Robin's-egg Cadillac, and the gold coin that says "your friendship means more to me than a pot of gold"06:26 — A Morgan Stanley account at 14, paper route money, and his first stock: Sears Roebuck07:44 — Nobody from his high school went to the military. He went to the Air Force Academy three days after graduation: "the best thing I ever did, other than marrying my spouse"11:50 — The Cirrus G7, the parachute that lowers the whole plane, and the button his wife can push if Glenn stops functioning mid-flight13:35 — From AWACS pilot to pharma rep to stockbroker: dialing 200 people a day, 10 conversations, one client17:45 — Net worth leaving the Air Force at 29 and the million-dollar goal on a piece of paper that "never happened"19:26 — The $2M–$20M client sweet spot, and why the firm has never contracted in 25 years — even 2007–200921:57 — Why he went from owning 100% of the firm to 20%: "How could they not have equity?"24:03 — The 11x17 "life map," and the client who was stabbed and left for dead in her New York apartment26:15 — HENRYs who save $10K a month and still need to be told to go enjoy the rest: "People get cancer. People die falling off a ledge."28:49 — "If you don't spend this money and fly first class, your kids will when you're dead"30:40 — The net worth where Glenn stopped worrying: "probably above 20"31:49 — Alimony, fun, and the pen-and-paper checkbook ledger a $1.5B wealth manager uses to track his Amex33:29 — The $1.25M four-seat plane, $40–50K a year to operate, and a $30–40K monthly burn before philanthropy35:10 — Giving appreciated stock and exceeding his deduction limit every year36:21 — Why he still goes to work at 63, the wingman system, three chronic illnesses, and "sometimes a founder needs to get out of the way"39:40 — The Melissa example: $100 a month in 1993 to the best trips on earth41:26 — Where to park $10M after a liquidity event: "you're going to collect around $300,000 a year in dividends and interest"42:55 — Not a real estate guy, the $100K driveway, and "I never invest in things that eat while I'm asleep"44:48 — 90% in global equity, and why "they're not stocks, they're companies"45:40 — Reframing an $80K private flight as a month and a half of portfolio income47:39 — What he'd tell a 20-year-old picking a major: English or historySponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- Aug 18, 202617 min
5 Things Rich People Refuse to Buy
We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.A $3 billion founder's money advice: keep driving the Chevrolet. Here's why the richest guests all say the same five things.After 100+ episodes of Moneywise, the same five spending refusals kept showing up — from a $3B founder who's never sold a company, a guy who lost 95% of his net worth and won't buy his own socks, and Bryan Johnson, who spends $2M a year on his body and almost nothing on anything else. None of them read the research. There's 50 years of it, and they all landed in the same place anyway.This episode covers all five: first class, new cars, meaningless stuff, angel checks, and kids' comfort — plus the study behind each one (lottery winners, the MIT Celtics auction, the marshmallow test follow-up). Then Anne Mahlum, who sold SolidCore for nearly $100M and forces herself to spend $200K/month, tears the whole list apart. The episode ends with a 10-minute exercise using two questions that decide what stays on your card statement.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwEpisodes Mentioned:How Rich Is 'Rich Enough' to Fly Private? — https://www.youtube.com/watch?v=5ZyTo6gppPw"I'm worth about $3 billion": What Happens When You DON'T Sell Your Business — https://www.youtube.com/watch?v=uZM0K9eqzx0What It's Like to Lose 95% of Your Net Worth Overnight (the socks guy) — https://youtu.be/fW-F3MKwevIBryan Johnson: I Probably Won't Actually Live Forever — https://www.youtube.com/watch?v=icWHq_xjhacHow to Not Ruin Your Kids with Your Wealth ft. Dr. Becky — https://www.youtube.com/watch?v=uB1SmMA-nLkTimestamps:0:00 — Cold open: the $3B founder, the socks guy, and Bryan Johnson's $2M body budget0:28 — 100 episodes in, the same five patterns kept repeating — and 50 years of research explains them1:05 — Why guests reveal their real numbers on Moneywise1:50 — #1: First class. "I still fly coach unless it's international" — his "poor kid habit"2:27 — Hedonic adaptation, and the lottery winners who scored lower on enjoying breakfast3:52 — #2: New cars. The $3B founder's advice: don't buy the Ferrari, drive the Chevrolet4:14 — The Millionaire Next Door data (most popular millionaire car: Ford F-150), "big hat, no cattle"4:40 — The commute study: zero relationship between car value and happiness5:35 — #3: Stuff. The socks guy's filter: "Does this dollar come back to me or is it gone?"6:03 — Stanford brain scans: every purchase is want vs. hurt6:28 — The MIT Celtics auction — credit card bidders paid double7:26 — #4: Angel checks. Bryan Johnson writes none — half of deals lose money, 7% produce 75% of returns8:41 — Opportunity cost neglect and attention residue: every check is an open tab in your head10:15 — #5: Kids' comfort. Parents who could buy any seat, flying the family in coach on purpose11:06 — The marshmallow test follow-up wealthy parents actually care about12:11 — 70% of family money gone by generation two, 90% by generation three13:17 — The counterargument: Anne Mahlum ($115M, spends $200K/month) — "I hate when people don't spend on principle"14:19 — The 2023 rerun of the $75K happiness study, and buying back time15:55 — The 10-minute exercise: two questions to run against last month's card statement16:33 — If you run a $3M+ company: HamptonSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
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About Moneywise
This is Moneywise, a podcast where host Daniel Berk is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
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