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.
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"]