the biggest bets, trades and fortunes, told from the first move. real people, sourced stories.
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Dan Bilzerian once signed away a third of his trust fund to get his father out of jail. His dad didn't talk to him for months after that.
Dan was in the military at the time. His father had been held in contempt of court for 9 or 10 months and kept getting moved from one maximum security prison to the next, until they came to Dan with a deal:
"If you sign over a third of your trust fund, we'll let him out."
He signed, and his dad was not happy about it. That money was set up for his sons, and Dan says his father would have sat in jail for 10 years before giving them 50 bucks.
The fund was once worth around $96 million. When Dan sold it in 2019 or 2020 it was worth about $1.5 million, a little under.
In the video below he explains where the rest of it went.
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Tom Hanks once had $25 in the bank and a kid to feed. He had to fight a bank manager to get $50 of his own unemployment money.
This was New York, before anyone knew him. He'd sold the car and a few other things to put a deposit on a dark little apartment in Hell's Kitchen. Groceries were $45 a week, and he rounded every price up at the store so he'd walk out a few bucks ahead.
Then his first unemployment check came in, close to $500, from the state of Ohio. The bank wanted to hold it until it cleared.
"I'm not a contentious guy, but I did cause a stink."
"I got a kid who needs groceries. This check is from the state of Ohio. It's good."
The manager was furious and let him take about $50.
A few years later he played Forrest Gump. In the video below he says what that bank branch is today.
Steve Jobs was worth over $200 million at 25. His daughter Lisa grew up on $385 a month.
He denied she was his. The county sued him for child support, and a paternity test said he was the father.
In her memoir she remembers her mom on the phone with him, sobbing and begging for money. Lisa was a little girl. She took the phone and said: "Just give her some money." Then she hung up.
Years later he was dying, and she was sitting by his bed. He kept saying the same thing.
"I owe you one, and I'm so sorry."
In the video below she says whether she ever forgave him.
Brad Keselowski's family lost their NASCAR team in 2006. His mom says he later paid off what they owed himself, "to the tune of six-digit numbers."
K-Automotive was his dad Bob's truck team, and Brad drove for it. He's talked about hotel credit cards getting declined and working in the shop through Michigan winters with the heat off to save money. They sold the shop and the trucks, and it still didn't cover the debt.
What stuck with him was the week it all got moved out the door, down to the pictures coming off the wall. He still puts that one on himself: "I called for the ball."
His mom: "He gave us every penny he had to pay our bills." Without it they'd probably have lost their home.
He won the Cup title in 2012. In the video below he says what paying it all back actually felt like.
J.J. Watt signed a $100 million contract in 2014. Then he and his friend from back home went on Google and typed "what do rich people buy?"
His buddy Taylor was hanging out at his house that day. Watt came home from work and told him they got the deal done. Taylor asked what he got. "A hundred million dollars."
They're both from Pewaukee and have been friends forever. He says they just looked at each other with "the craziest, stupidest grin."
So they went through lists and lists of yachts, jets and cars, because he felt like you almost have to buy something after a deal like that.
His mom still looks over his money. She worked her way up from secretary to vice president at her company, and he says she'll always make sure he's not doing anything stupid.
In the video below he says what he found on those lists that he actually needed.
Paul Heyman put most of what his family had into a wrestling company that taped its TV in a Philadelphia bingo hall. 7 and a half years later he was filing for personal bankruptcy.
When he took over ECW, the owner was already $470K deep into a $500K line of credit. In his words, they were on death's door.
The interviewer says it was $4 million from his parents. Heyman says he honestly doesn't know how much he spent. He never paid himself, whatever he had just went into keeping the company alive.
He was up against Ted Turner's WCW and Vince McMahon, both billion dollar companies on national cable.
"And here I am at a bingo hall in Philadelphia with a local sports channel clearance."
Then came the day he had to accept it was going into bankruptcy. He calls even that day a great day.
The interviewer didn't buy it either. In the video below he explains exactly why he meant it.
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Kelly Slater went on to win 11 surfing world titles. Around 21, with one title already won and over $1 million made, he found out he was in debt.
He was trying to buy a house with his then fiancée. That's how it came out.
He grew up with no money. His mom raised 3 boys on about $2,000 a month without much help from his dad, and most days she was scraping quarters together to pay for his school lunch.
"It's not a sob story. It's just the way it was in my family."
He says when you're raised like that you don't have a lot of intelligence around money. So once he was getting paid he didn't handle his finances at all, his mom just took care of it for him.
"It was a real kind of quick wake-up lesson."
I kind of get it. If nobody ever showed you, you don't go looking at the numbers until something like a house makes you.
In the video below he says the first thing he changed after that.
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Charlie Sheen was paid $1.8 million an episode on Two and a Half Men. Today he wears a Timex and drives a Cadillac.
He says he did money in reverse. Most people start in apartments and townhouses, strike gold, then move into mansions. He had the mansions early. Now it's totally flipped.
"It's kind of refreshing."
He once owned one of the nicest vintage watch collections in the country. He was still late to everything. Sometimes not by hours. By days.
"How many cars can you drive at the same time? How many watches can you wear?"
Then he talks about a drive with his buddy Eddie Braun, his old stunt double. Years earlier Sheen had handed Eddie a $1 million check to stop doing stunts.
In the car Sheen said he gave it all away. Burned it all to the ground.
"Now what?"
In the video below he repeats exactly what Eddie told him.
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Jason Tatum signed a $314 million deal with the Celtics. The morning after a trip with his friends, his mom still calls him.
"Who is Mr. Jones? Why did you give him $12,000?"
He only takes those trips once or twice a year. LA, Vegas, Miami. Everything that has to do with Jason Tatum goes through her, so she processes every wire and gets every receipt.
She says she can tell from his face when he walks into her office that a wire is coming. He's already picked something out. He likes nice watches.
"What does this watch do?"
Before he got drafted, they made a deal. He couldn't spend the money he made from the Celtics. He had to live off endorsements. His mom and his accountant both agreed.
They didn't know he'd make as much off the court as he did.
In the video below he explains the loophole he found in that deal.
Joe Gibbs had already won three Super Bowls. Six months into his NASCAR team, he found out they were $250,000 in the hole.
He heard it at dinner, right as he was about to take a bite of his swordfish.
"This is absolute panic."
The team started with nothing. His son JD told him he'd rather do racing than football. Gibbs said they didn't have anything, but they could put a dream on a piece of paper and try to sell it.
He showed up at Interstate Batteries. First question: who's your driver?
"We don't have one."
Where's your race shop?
"We don't have one."
Two days later the answer was yes. Year one was 17 people, one car and zero wins. They cut back, watched every dollar and stopped going deeper into debt.
Year two, first race of the season, the Daytona 500. They were running up front, and it came down to the last pit stop. JD was changing the tires.
In the video below he repeats exactly what JD said when they asked if he got the lug nuts tight.
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Greg Norman was getting paid millions to wear other companies' logos. He decided that was the problem.
He was one of the few athletes in the world getting that kind of endorsement money. He was repped by IMG, the famous sports management firm.
They paid him. He wore their logo. Every time he played well, their brand got minutes of TV time.
"I really didn't get anything out of it except dollars."
Most athletes would stop there.
"I didn't want that. I wanted to build equity in my own brand."
One problem. He didn't have a brand.
Then the man who owned Reebok told him something about the Shark logo. When his management contract came up in 1993, Norman didn't renew and paid for everything himself.
In the video below he says exactly what he heard, and what happened once the cash started going out.
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Barry Diller took Home Shopping Network from losing $70 million a year to making $60 million. Within a year.
Asked how, he gave a one-word answer.
"Easy."
The company wasn't broken, he said. It was mismanaged. Then the internet showed up, and he already knew how people bought things through a screen.
"That created 100 billion dollars of value."
Then 9/11 hit. Travel stopped worldwide, and Expedia, the travel company he was buying, had no revenue at all.
"It was like dead cold."
What one person in the room said next, and what Diller decided to bet on, is in the video below.
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Tony Romo was an undrafted backup making the league minimum when Jerry Jones and Bill Parcells offered him $500,000. He asked for $2 million.
It was his second year in the NFL. They sat him down right before a preseason game.
His logic was simple. If they had real money in him, they would have to put him in a game and see if he was worth it.
"Believe me, I didn't want to do it."
Jerry said yes on the spot.
What Parcells told Jerry the second Romo walked out of that room is in the video below.
"Oh my gosh, I'm the richest guy in the world."
Shaq once turned down Howard Schultz and his own Starbucks stores with one sentence.
Schultz wanted him to open Starbucks locations in Black neighborhoods.
Shaq grew up on sweet tea and hot chocolate. He had never seen anyone in his family drink coffee.
So he looked Schultz in the face and told him it wouldn't work.
In the video below he explains exactly what he said, and who took the deal right after him.
"On every corner, in every city, in every country, I see a Starbucks."
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Donald Trump once mailed John McEnroe a letter offering $1 million to play Serena or Venus Williams. McEnroe said no.
He was calling a match when the envelope showed up.
"Dear John, I want to offer you $1 million to play either Serena or Venus."
Serena and Venus had been saying they could beat a lot of guys. Somehow McEnroe became the one everybody asked.
He was the number one player in the world. He wasn't going to sit there and say he couldn't beat them.
So why turn down $1 million?
In the video below he explains exactly why. Then he asks a question about the NBA that nobody else gets asked.
"Somehow it's me, the old fart."