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"]

What is Moneywise?

This is Moneywise, a podcast where host Daniel Berk is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Check it out at https://joinhampton.com/.