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"]