Moneywise

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”]

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”]

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"]

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"]

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"]

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"]

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"]

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"]

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 Roebuck
07:44 — 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-flight
13:35 — From AWACS pilot to pharma rep to stockbroker: dialing 200 people a day, 10 conversations, one client
17:45 — 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 2007–2009
21:57 — 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 apartment
26:15 — 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 Amex
33:29 — The $1.25M four-seat plane, $40–50K a year to operate, and a $30–40K monthly burn before philanthropy
35:10 — Giving appreciated stock and exceeding his deduction limit every year
36:21 — 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 earth
41:26 — 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 income
47:39 — 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/@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.

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=uZM0K9eqzx0
What It's Like to Lose 95% of Your Net Worth Overnight (the socks guy) — https://youtu.be/fW-F3MKwevI
Bryan Johnson: I Probably Won't Actually Live Forever — https://www.youtube.com/watch?v=icWHq_xjhac
How 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 budget
0:28 — 100 episodes in, the same five patterns kept repeating — and 50 years of research explains them
1:05 — Why guests reveal their real numbers on Moneywise
1:50 — #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 breakfast
3:52 — #2: New cars. The $3B founder's advice: don't buy the Ferrari, drive the Chevrolet
4:14 — 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 happiness
5:35 — #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. hurt
6:28 — The MIT Celtics auction — credit card bidders paid double
7:26 — #4: Angel checks. Bryan Johnson writes none — half of deals lose money, 7% produce 75% of returns
8:41 — Opportunity cost neglect and attention residue: every check is an open tab in your head
10:15 — #5: Kids' comfort. Parents who could buy any seat, flying the family in coach on purpose
11:06 — The marshmallow test follow-up wealthy parents actually care about
12:11 — 70% of family money gone by generation two, 90% by generation three
13:17 — 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 time
15:55 — The 10-minute exercise: two questions to run against last month's card statement
16:33 — 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/@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 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/@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 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/@themoneywisepodcast
Follow Daniel on X: https://x.com/danielcberk
Listen 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/@themoneywisepodcast
Follow Daniel on X: https://x.com/danielcberk
Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

We did something nuts: we got 50+ founders to reveal their net worth, portfolios, income, expenses. Its free and right here: https://joinhampton.com/mw-wr

Why this podcast exists:

• Hampton is a community for founders. Members do an ave of $20m/year in revenue.
• Tons of the convos within the community are about money: how to invest, how to spend, how much to pay yourself...all this stuff you can't Google.
• We thought "Let’s just make these convos public". And thus, this podcast Moneywise came to be.

We publish weekly. Click the subscribe button and the goodness will be delivered.

Also...we've done 100+ episodes. If you want the aggregate info of all the numbers, meaning the net worth, spending, income of 50+ founders ranging from $10m to $1 billion: https://joinhampton.com/mw-wr

Ok, so let's talk David Royce, today's guest:

He built the same pest control company four times — $13M, $30M, $135M, $1.5B — and says the first exit was the most life-changing.

David Royce sold four pest control companies — Moxie, Eco First, Altera, and Aptiv — each bigger than the last, culminating in a $1.5B sale of Aptiv when it was doing $508M in annual revenue. He kept 100% equity through the first three, gave 25% of the last one to his employees, and personally walked away with hundreds of millions across the run. He's now on an indefinite sabbatical, investing through Iconic (the firm that manages Zuckerberg's and Dorsey's money), with half his net worth in S&P 500 and the rest in private equity, direct deals, and alternatives — including multiple Anthropic investments.

This episode covers the exact mechanics of each asset-sale exit, why David kept restarting instead of holding, his full portfolio framework (including the 4-year cash buffer strategy), the "the answer is just a little more" moment that hit every entrepreneur in the room, and the story of flying his dying father on a private jet from a New Orleans hospital to Cedars-Sinai at 2am — made possible only by one call to a CEO WhatsApp chain.

Timestamps:
00:01:39 — David's full intro: four companies, four exits, what actually happened with the money
01:55 — First company (Moxie): nearly went bankrupt the first year, how a cash flow crisis taught him "cash was king"
03:14 — The asset-sale strategy: selling customers and technicians to Terminix while keeping the sales operation
04:57 — "Pretty close" — David confirms Forbes' reported $13M and $30M exit figures
05:37 — Why he gave 25% of Aptiv to employees and stepped back as chairman
06:23 — Aptiv was doing $508M in revenue; Daniel and David settle on $1.5B as the sale range
07:13 — What he actually took home: cap gains, California taxes, "hundreds of millions"
08:37 — Net worth today: "do the math backwards and figure it out"
09:09 — Portfolio breakdown: 4-year cash buffer in fixed income, S&P 500 with tax-loss harvesting, alternatives
11:31 — "I just invested in Anthropic — three different times in the last year and a half" via Iconic
14:35 — "The one that was life-changing was the first one" — $13M from nothing hits differently than $1.5B
17:46 — Why pest control? A starving college student, a friend who made $25K in a summer, and zero sales for five days straight
21:16 — His boss's question that changed everything: "What on earth would you go work for somebody else?"
27:31 — Fifth grade through eleventh grade: watching his family nearly lose the house, the fear that built everything
36:35 — Flying his dying father on a private jet from New Orleans to Cedars-Sinai at 2am
39:36 — What he wants to be remembered for: "The sign of a good leader is not how many followers you have, but how many leaders you create"

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She sold for $88M, almost bought a lake house she didn't want, and spent $340K on Knicks playoff tickets — then gave two away because it felt better.

We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-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.

Also, this podcast is made by Hampton, which is a community for founders doing on average $20M a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "Why not, let's make it public." If you are a founder, apply here: https://joinhampton.com/mw

Anne Mahlum built Solid Core from $175,000 of her own savings into an $88M exit. Two years later, her net worth is $115–120M, with $65M in public equities and $15M in a single stock alone. But the numbers are the least interesting thing that's happened since.

After the sale, she secretly launched a second fitness company, had panic attacks she's never talked publicly about, shut the whole thing down, and spent two years in legal fallout. Then she had a baby, pulled an accepted lake house offer the morning after making it, and started forcing herself to spend $200K a month just to stop the money from piling up.

This episode covers the full portfolio breakdown two years post-exit, why she's done with private investments, the Ambition story she's never told, what a baby did to how she thinks about money and time, and what she actually wants to be remembered for — which has nothing to do with net worth.

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JOIN HAMPTON:
These episodes often come directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw.

HOW FOUNDERS ARE BUILDING WEALTH:
How much do founders actually make, spend, invest, work, and keep in net worth? Hampton surveyed founders directly and put the answers into one report. Download it for free here: https://joinhampton.com/mw-wr

EPISODE DETAILS:
Most founders spend years learning how to make money. Almost none of them prepare for what their brain does once they have it.

Henrik Cronqvist is a behavioral finance professor who trained under Nobel laureate Richard Thaler and has spent 25 years studying exactly that. His research has been cited over 7,000 times. He has studied 38,000 people to answer one uncomfortable question: how much of the way you save, spend, and invest is actually hardwired into your DNA?

The answer will change how you think about every financial decision you make after an exit.

This episode covers the science behind why the traits that made you a great founder may work against you as an investor, what actually happens in your brain the day the wire hits, and the one thing Henrik says every founder should do before making a single investment.

TIMESTAMPS:

00:00 — The traits that made you a great founder will make you a bad investor
01:45 — What is behavioral finance and why should founders care
04:35 — How Henrik got into this research (the Stockholm subway story)
06:39 — The 38,000 twin study: how much of your money behavior is genetic
10:56 — The first thing to do when the wire hits your account
12:49 — Loss aversion, performance chasing, and home bias explained
20:35 — Your personal mortgage predicts how you'll run your company's finances
30:08 — Why your brokerage app is designed to work against you
37:07 — Why founders feel depressed after selling (the science behind post-exit emotions)
47:14 — "I think I'm the exception" — and what the data actually says about that