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.
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"]