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He's Worth $50M and Spends $110K a Month on a Zoo That Makes $0 artwork

He's Worth $50M and Spends $110K a Month on a Zoo That Makes $0

Moneywise

October 6, 2026

We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. 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.

Speakers Daniel Berk, Dan Fleyshman

TopicsInvestingBusinessEntrepreneurship

Daniel Berk (0:00)

At 17, Dan Fleyshman snuck into a Las Vegas clothing convention he was too young to register for, using $5 business cards from a vending machine. He walked out with a million dollars in orders, and the next year he did nine and a half million. At 23 years old, he took his energy drink company public. And today, Dan has 43 angel investments. He's raised $56 million across 18 different companies through his syndicate, and only three of them have failed. One Acai chain he backed with a $500,000 check on from 13 locations to 104 Under oath, he says his net worth is for sure over $50 million, but he can't give me the exact number. And by the end of this episode, you'll understand exactly why. This conversation fits Hampton so well. Hampton is a private network of high growth founders doing on average $25 million in revenue. And a lot of them have started and sold companies just like this. Dan's whole philosophy fits into one sentence, go all in on one company with your time, then spread your money everywhere else. Founders inside of Hampton argue about that exact trade-off all the time. I get to bring those conversations out into the open on this show Moneywise. If that sounds like your world, check it out at joinhampton.com. In this episode, we're going to go over a lot. First, how a kid whose family lived on two grand a month flipped candy bars, saved $43,000 and then spent it all on a clothing brand instead of college. Then we'll get into the full money breakdown, the syndicate, the carry, a $9 million ranch with a lake and a zoo and over a million dollars a year in travel. Dan's awesome. I can't wait for you to listen to this episode. This is Moneywise. I'm your host, Daniel Berk. Here's your guest, Dan. Welcome back to another episode of Moneywise. I have an awesome guest today, Dan Fleyshman.

Really excited to hear your story. I wanted to start from the beginning. I was doing a little bit of digging on you and it looks like early on, you were selling baseball cards and you were only four years old. Walk me through that story and really even what went through your mind at four years old that led to, hey, I'm going to start being an entrepreneur is really what that was.

Dan Fleyshman (1:52)

My parents, we just didn't have much money. They were selling Levi's jeans out of the back of the van every Saturday and Sunday at the swap meet in LA. While they were selling their jeans at the back of a van, I had a little table a few feet away and I had my baseball cards. First, I had like 20 cards and I had 100 cards and I had 400 cards. I'd make like $4 and $21 and $18 and one time like $100, $200. I would just buy and flip and sell my way. Because I was so little, a lot of fun deals would happen because people would overpay. They'd pay me $10 for a $6 card. Doesn't sound like a big difference. When you do that multiple times a day, every day, every weekend, rain or shine, it adds up.

I had people who would give me trades of cards like, hey, take this card that's like $50 for your card, that's $30 and blah, blah, blah.

This just kept happening and I'd be five years old, six years old, seven years old and now I had experience. So anyways, I hustled my way up to getting a pretty big collection through those first few years, and then I started buying Magic the Gathering Cards and Pogs and all these other things too.

Daniel Berk (2:59)

So you've been an entrepreneur your entire life.

Dan Fleyshman (3:04)

Oh, yeah.

Daniel Berk (3:05)

Walk me through your money story. You've had a very successful career, you've done a lot of different things, I think almost 50 different angel investments, is that correct?

Dan Fleyshman (3:15)

About 43, yep.

Daniel Berk (3:17)

So you're leveraged in like kind of every direction of the universe. Walk me through your thinking there, why, and lead me up to today. We'll have a good conversation.

Dan Fleyshman (3:25)

Yep, so we didn't have much money growing up and $24,000 to support a family of four in Los Angeles back then.

My mom and dad were making two grand a month between working at Century 21 Real Estate and my dad driving a taxi. There just wasn't much capital. And then when they got divorced, my mom and I lived in this 92-year-old lady's one-bedroom and just slept on the couch. And so money to me was like, I need to make money to help my mom and to not be a burden to her. So like eight, nine, 10 years old, I was selling candy out of my backpack at school. My mom would give me $13 to buy candy at Costco. I then flip it for $30, give her her $13 back.

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