In 1938 two 23-year-olds from Cleveland sold every right to Superman for $130. In 2024 one copy of the comic they were paid for sold for $6 million. In the video below they tell how they made him, decades later, side by side. Then CBS News, December 1975. Listen to what Joe Shuster says their American dream became. Jerry Siegel wrote. Joe Shuster drew. For five years every newspaper syndicate turned them down. In 1938 a comic book publisher finally said yes: $10 a page, 13 pages, all rights. The check line read "Superman, $130." They kept writing and drawing him for nine years and were paid well for it, more than $400,000 between them by one count. In 1947 they sued to get the rights back. They lost, settled for about $94,000, and lost their jobs and their names on the comic. By 1975 Shuster was almost blind and living in near poverty in New York. Siegel was a $7,000-a-year clerk in Los Angeles. That October, with the Superman movie in production, Siegel sent the press a letter putting a curse on it. Two months later Warner gave them $20,000 a year each and put their names back on every Superman story. Worked out. 1938: all rights to Superman, $130. 1975: the pension, $20,000 a year, 37 years later. 2012: the $130 check itself, which DC had thrown in the trash, sold at auction for $160,000. 2024: one copy of Action Comics #1, $6,000,000. That's 46,000 times what they got for the whole character. Invested at 7% a year from 1938, the $130 would be about $44,000 today. The publisher has a case. Every syndicate had passed. It paid for the printing, took the risk on 200,000 copies, and $10 a page was the going rate. Nobody in 1938 knew what a superhero was worth, including the two kids who made him. You're the publisher in 1938. A character everyone rejected for five years just became the biggest hit you've ever had. Do you give the two kids a royalty, or hold them to the contract they signed?

In 1961 Jim Monaghan traded his half of Domino's to his brother Tom for a used Volkswagen Beetle. Today Domino's is worth about $10 billion. Decades later an interviewer asked Tom if his brother got the better part of that deal. "Yeah," he said. In the video below Tom tells it himself. Listen to what he sees out the window. Tom grew up in an orphanage. His father died when he was 4, on Christmas Eve 1941. At 23 he put everything he had, including his college money, into a failing pizza place in Ypsilanti, Michigan, with his brother Jim. $500 down, $900 borrowed from a credit union. Jim was a mailman. After they signed, he couldn't give up the route. "Too much security." Within months Tom was working seven days a week. One night Jim walked into the shop: "This is your type of thing, not mine. You can have it." Tom had nothing to pay him with. He looked out the window at the delivery car. "You take the Volkswagen. I'll keep making the payments." Worked out. 1961: half of a pizza place that was "just a negative, all kinds of debt and losing," Tom says. Price: a '59 Beetle. 1998: Tom sold his stake for about $1 billion. 2026: Domino's is worth about $10 billion. Jim's half: about $5 billion. Here's the uncomfortable part. On the day Jim made that trade, it was probably the right call. A steady paycheck beat half of a shop that lost money every week. It just turned out to be the wrong side of the next 60 years. Tom later gave most of his fortune away. "At one point I was a billionaire, but I gave all my money away. So now I'm a trillionaire." You're Jim in 1961. Steady mail route, and half of a pizza shop that loses money every week. Do you take the car?

Stu Ungar won the World Series of Poker three times and earned an estimated $30 million at the tables. When he died in a cheap Vegas motel at 45, investigators found $800 in his pocket. In the video below: the night he won his third title in 1997, holding up a photo of his 14-year-old daughter, and then his daughter herself, years later. The night before the final, she told him on the phone: "Daddy, I'm going to disown you if you don't win the tournament." "I'm going to win the tournament," he said, "and it's for you." He won. Then, on camera, he said something champions don't say: "I've neglected my kids… The only one that ever beat me was myself, in my bad habits." And: "I love you, honey, and I'll be seeing you soon." She found out later that he'd had her picture in his pocket the whole tournament. Eighteen months later a cleaning lady found him dead. Friends and fellow gamblers paid for the funeral. Worked out. Estimated career winnings: $30,000,000. Found in his pocket: $800. He kept about 1 dollar of every 37,500 he won. Nobody beat him at the table. The table was never where he lost. It's the night he won in 1997. You get to give him one rule. What is it?

In 1995 Jeff Bezos asked his parents to put money into his online bookstore. He told them there was a 70% chance they'd lose all of it. They wrote a check for $245,573. In the video below he tells the story himself, in 2001. Listen to his dad's first question. "What's the internet?" He wasn't betting on the company, Bezos says. He was betting on his son. It was a large part of their life savings. Worked out. His odds, by his own account: 30% it works, 70% it's gone. He thought a normal startup had about 10%, so he was already giving himself triple. On those odds, the most likely outcome of their check was zero. What happened instead: Bloomberg estimated in 2018 that the stake could be worth almost $30 billion if they still held it. $245,573 to about $30 billion is roughly 120,000 times the money in 23 years, about 66% a year. On his own 30%, the check's expected value was about $9 billion. Its most likely value was zero. Both numbers were true on the day they signed. "And they did it anyway." Your son asks for a big part of your life savings and tells you himself it's 70% likely to go to zero. Do you write the check?