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Steve Jobs was worth over $200 million at 25. He paid his daughter $385 a month. Her mother cleaned houses and went on welfare. The county had to sue him to pay it back. In the video below, his daughter Lisa talks about growing up with him. Jobs was 23 when she was born. He helped pick her name. Then he denied she was his. A DNA test said he was the father. He told Time magazine that 28% of men in America could be. The same year, Apple went public. He became one of the richest young men in the country. He named a computer after her: the Apple Lisa. For years, he refused to admit it. One day her mother was on the phone with him, sobbing, begging for money. Lisa, a little girl, took the phone and said: “Just give her some money.” Then she hung up. Another time, her mother asked him for a house. He said yes. Then he bought one for himself. At 14 she moved in with him. His condition: she couldn’t see her mother for six months. Years later, he was dying of cancer. She sat by his bed. “The thing he kept on saying is, ‘I owe you one, and I’m so sorry.’” Did she forgive him? “I think not at the time.” “In many ways, yes.” When her memoir came out, his widow and his sister released a statement: her story “differs dramatically from our memories.” The case for Jobs: he was young, he came back, and he tried to make it right before he died. The case for Lisa: a billionaire’s daughter shouldn’t have grown up on welfare. He named a computer after her. He wouldn’t say she was his. On his deathbed, he said, “I owe you one.” Was “I’m sorry” enough, or did it come 30 years too late?

Dave Chappelle walked away from a $50 million contract. Years later, he said he never got paid for the show that made him famous. He says the money was never the point. In the video below, David Letterman asks him if he regrets it. In 2003, Comedy Central gave him his own sketch show. It became one of the most quoted shows on TV. In 2004, he signed a two-year deal for seasons three and four. $50 million. In 2005, in the middle of shooting, he walked off the set and flew to Africa. Almost no one knew where he was. Letterman asks what happened. “Technically, I never quit. I’m seven years late for work.” The trip that started all the rumors? “I was there for two weeks.” Then Letterman asks the real question: does he regret saying no to that money? He answers with a story. He is at a nice restaurant with his wife. Across the room sits a man with $100 million. “We’re eating the same entree.” “The only difference between having $10 million and $50 million is an astounding $40 million.” He admits he would like to have it. “Money is the fuel for choices.” In 2016, Netflix reportedly paid him up to $60 million for a run of stand-up specials. In 2020, Chappelle’s Show appeared on Netflix. He later said Comedy Central licensed it without paying him. He had signed that contract at 28, broke, with a baby on the way. He asked fans to stop watching his own show. Netflix pulled it. A few months later, he said Comedy Central had made it right. The case for Comedy Central: he signed the contract. They offered him $50 million to keep going. He was the one who left in the middle of a season. He left $50 million on the table. Netflix reportedly paid him $60 million. And he still fought for the show with his name on it. So was walking away from $50 million the worst decision of his career, or the best one?

Martha Stewart was worth over $1 billion. She went to prison over $40,000. She told Barbara Walters it was “about 0.006% of my net worth.” Then she said: “I don’t think I will be going to prison.” In the video below, she tells it herself. She grew up in New Jersey, one of 6 kids in a house with 1 bathroom. She modeled at 13, worked as a stockbroker, then built an empire out of cookbooks, TV, magazines and Kmart. In 1999 she took her company public. “Well over a billion dollars,” she says. America’s first self-made female billionaire. On December 27, 2001, on her way to Mexico, she got a message from her broker, Peter Bacanovic. ImClone was about to drop. Its CEO, Sam Waksal, who had dated her daughter, was secretly dumping his shares before the government rejected his cancer drug. She sold that day. “I sold 3,900 shares.” It saved her “approximately $40,000.” Waksal got 7 years. Then prosecutors came for her, not for the trade, but for lying about it. She stepped down from her own company and watched her stock crash. “My net worth has been cut at least in half.” Barbara put it at $400 to $700 million. “Of course I’m scared,” she said. “The last place I would ever want to go is to prison.” In March 2004 she was found guilty on all four counts. In October she reported to a federal prison camp in West Virginia. The case for Martha: more than 7 million ImClone shares traded that day, and she became the face of it. The case against her: she wasn’t convicted for selling. She was convicted for lying. Today she’s 85, rich again, and still says the prosecutors “should have been put in a Cuisinart and turned on high.” She saved $40,000. She lost up to $700 million. She swore she’d never see prison. Was she punished for lying, or for being Martha Stewart?

He made $110 million in the NBA. Two years after he retired, he was bankrupt. His filing showed $4.3 million in assets and $12.7 million in debt. He says nobody stole it from him. In the video below, he tells it himself. Antoine Walker grew up in Chicago with nothing. At 20, the Boston Celtics drafted him 6th overall. 3 All-Star games. An NBA title with Miami. 13 seasons. While he was still playing, he put his name on real estate loans with 7 to 8 banks. Then 2008 hit. The banks wanted their money back. All at once. But that wasn’t the only hole. Private flights. The best hotels. Everywhere he went, his crew went too. Stephen A. asked how many people he was paying for. “10 to 15 people. On a consistent basis.” Not family. Friends. “How much did they cost you?” “A couple million dollars.” “When I made it, I wanted to make sure my guys got to enjoy it too.” Then Skip Bayless gave him an easy way out. Did he blame his financial advisers? “No. I blame myself.” After the bankruptcy, the former All-Star went back to the minor leagues, playing for a fraction of his old salary to pay off what he owed. Today he talks to young players about money, so they don’t end up like him. He made $110 million. He owed $12.7 million. He still says it was his fault. Was he a loyal friend, or did his friends cost him everything?

At 13, she was a meme on Dr. Phil. At 18, she made $1 million on OnlyFans in six hours. Now the number people ask her about is $75 million. In the video below, she’s asked if it’s true. She doesn’t argue. She explains how the money arrives. In 2016, Danielle Bregoli went on Dr. Phil as a “troubled teen.” She told the audience to “cash me outside.” The clip went viral. She became one of the biggest memes on the internet, and the joke was on her. She didn’t disappear. She turned the meme into a rap career as Bhad Bhabie. Then, in April 2021, just over a week after her 18th birthday, she opened an OnlyFans account. By her own account, she made about $1 million in the first six hours. And about $4 million by the end of the first day. In 2024, she posted a screenshot: $57 million in net earnings. So how does that kind of money show up? “I’m signed to an agency, and they pay me bi-weekly.” “Every other week.” Direct deposit. What does she do with it? “I bought a lot of cars. I bought a lot of houses. I have three houses. I have like seven cars.” “I don’t really go too crazy.” The case for the critics: she became famous as a child crying on daytime TV, and the internet never let her forget it. The day she turned 18, the same internet was ready to pay. The case for Bhabie: everyone made money off her at 13. At 18, she made sure the money finally went to her. Dr. Phil got the ratings. The internet got the meme. She got the $75 million. So who really profited from the “cash me outside” girl?

She told them no to porn. Two weeks later, her parents were watching her on Pornhub. The company behind it reportedly made $17 million. She says she never saw a dime. In the video below, she tells it herself. She was 22. A yoga instructor, paying her own way through college with clothed fitness modeling. The ad on Craigslist said: “Female fitness models wanted, age 18 to 22.” The website looked professional. She talked to the photographer. She did FaceTime calls with two “reference models” who swore the guys were great. After about 10 calls, they mentioned they also made adult films. $10,000, instead of “just a couple thousand” for yoga clothing. “Absolutely not.” “It’s always an option,” they said. She flew to San Diego. Her parents had her flight and hotel details. A black Escalade picked her up at the airport. The doors locked. They took her purse with her phone in it. In the hotel room, they unplugged the phone and put papers in front of her. “Sign here. Initial here.” She asked to read them. “No, no, we have to hurry.” She says she was raped through the night. When she tried to stop it, they told her: “We’ll put everything on the internet with your full name, or we’ll send it to your parents. Do you want them to find out?” Two weeks later, it was online. With her full name. A boy from high school sent it to her first. Her parents got it from family friends that same night. The link everyone was passing around was on Pornhub. The company was GirlsDoPorn. Performer Ruben Andre Garcia got 20 years. Prosecutors said owner Michael Pratt made about $17 million before he fled the country. The women won millions in court. She says she has never seen a dime. She has changed her phone number six times. “I’ve never done any of this for money.” They promised her $10,000. They made $17 million. She’s still trying to get the video taken down. Should the sites that hosted her video pay too, or is a prison sentence enough?

Chris Tucker was paid about $10,000 to play Smokey in “Friday.” The movie made nearly $28 million. A few years later, he was reportedly getting $20 million a movie. In the video below, Shannon Sharpe asks him about it on Club Shay Shay. “It was just a small movie. We filmed it in 20 days.” “I got about ten thousand dollars for it or whatever. I didn’t care. I wanted the opportunity.” The whole movie, he says, cost “either two million or three million.” There was no money for mistakes. “We only had two takes. If I mess up one time, you get one more time, and that’s it. We’re gonna cut you out.” They shot on one street almost the entire time. A few small scenes in a studio. That was it. “It was just a camera and me and Cube on the porch.” “And magic came out of it.” Smokey became one of the most quoted characters in movie history. “Friday” turned into a franchise with two sequels. Tucker wasn’t in either of them. Instead, “Rush Hour” made him a global star. For “Rush Hour 2,” he was reportedly paid $20 million. From $10,000 to $20 million in six years. The case for the studio: he was an unknown comedian in a tiny movie with a $3 million budget. $10,000 was a normal deal, and he says himself he didn’t care about the money. The case for Tucker: Smokey is the reason people still quote “Friday” 30 years later. The franchise kept going. His check didn’t. So was $10,000 fair for Smokey, or did “Friday” owe Chris Tucker a lot more?

Paul McCartney told Michael Jackson to get into music publishing. Then Jackson bought the rights to Paul’s own songs. Over 200 Beatles songs, for a reported $47.5 million. In the video below, David Letterman asks him about it. Paul tells the whole story. They were friends. Jackson called him at home on Christmas Day, and Paul thought it was a fan who’d found his number. They made hits together. Then Jackson asked for advice. Paul took him aside: think about getting into music publishing. Owning songs is where the real money is. Jackson’s answer: “I’m gonna get yours.” “I thought that was a joke,” Paul says. In 1985, it wasn’t. The catalog came up for sale, and Jackson bought it. Paul says he didn’t even mind that part. Jackson had the cash, and someone was selling. What hurt came later. Paul wrote to him. More than once. “Even if I was just a writer on the payroll, after 30 years of being reasonably successful for this company you now own, don’t you think I could have a raise?” Jackson’s reply: “That’s just business.” “He won’t even answer my letters,” Paul says. Letterman suggests they go in together and buy the songs back. Paul shakes his head. “The trouble is, I wrote them for nothing. And buying them back at these phenomenal sums, it just rubs you the wrong way.” Years later, Sony paid $750 million for Jackson’s half of that catalog. The case for Jackson: it was a public sale, and he paid the market price. Paul had the money too, and could have bid. The case for Paul: he gave Jackson the idea, as a friend. Then he had to ask that friend for a raise on his own songs. One wrote the songs for nothing. The other bought them, and called it business. So was Michael Jackson a smart businessman, or a friend who took the advice and kept the songs?

Dana White said Francis Ngannou left the UFC because it was “all about the money.” Ngannou says he turned down $5 million while he was broke and owed a friend $200,000. In the video below, he tells the story, sitting next to the man he owed. Ngannou was the UFC heavyweight champion. His contract was running out, and the UFC wanted him on a new deal. He says the new deal would have paid him $5 million for his next fight. Under the old one, he got $600,000. “I took $600,000 for my last fight in the UFC as opposed to 5 million that they were offering. For the same fight.” “And I was broke.” Then he points at one of the hosts: “I owe him 200,000.” “Hey, let’s not talk about that,” the host laughs. So why walk away from $5 million? “I couldn’t sell out what I wanted just because of more money. Obviously I needed that money. Obviously, I never had that amount of money.” One of the hosts says the UFC later offered him $8 million to stay. He still left. He wanted to box. As a free agent, he fought Tyson Fury, put him on the canvas, and reportedly made $10 million. His next fight, against Anthony Joshua, was estimated by Forbes at around $20 million. The case for Dana White: the UFC offered him millions to stay, and every fighter signs the same kind of contract. Ngannou chose to leave. The case for Ngannou: he said no to $5 million while he was in debt. Whatever it was about, it wasn’t the money. One man said he left for money. The other turned down $5 million to leave. So was Dana White right about Ngannou, or did he never understand what Ngannou was fighting for?

Michelle Williams was paid less than $1,000 to reshoot “All the Money in the World.” Mark Wahlberg got $1.5 million. Same movie. Same reshoots. She calls it “the exact same amount of work.” In the video below, she stands on Capitol Hill and tells the story herself. In 2017, Kevin Spacey was cut from the film after allegations against him. The studio replaced him with Christopher Plummer and reshot his scenes, weeks before release. Williams offered to help for nothing. She told ET Canada: “You can have my salary, you can just take it.” Director Ridley Scott said the same thing in public: “Everyone did it for nothing.” Not everyone. Wahlberg’s team negotiated $1.5 million. Williams got an $80 per diem. When the numbers came out, Wahlberg gave his $1.5 million to the Time’s Up legal fund, in her name. Their agency added $500,000. But for Williams, the worst part came after. “The news broke that I had been paid less than $1,000 compared to the $1.5 million that my male counterpart had received for the exact same amount of work. And guess what, no one cared.” Then she asks why she came to Washington: “If it was like this for me, a white woman in a glamorized industry, how were my sisters suffering across their professions?” The next year, she won an Emmy. On stage, she thanked the studio for one thing in particular: “paying me equally.” The case for Wahlberg: his reps asked for money, which is their job. He didn’t set her pay. And when it came out, he gave every dollar away. The case for Williams: she worked for free because she was told everyone was. He didn’t. She offered her salary to save the movie. He was paid $1.5 million for the same days. So was Wahlberg the problem, or the system that let one actor ask and told the other not to?

Snoop Dogg says his music hit a billion streams on Spotify. His check wasn’t even $45,000. That’s about $45 for every million plays. In the video below, he tells the Business Untitled podcast how he found out. His publisher sent him the Spotify numbers. A billion streams. He asked for one thing: “Break that down. How much money is that?” “That shit wasn’t even $45,000.” Then he says it again, slower: “Crazy.” This is one of the most famous rappers alive. 30 years of hits. And a billion plays paid less than a mid-level salary. So he tried something else. With his son, he started selling music directly to fans through NFTs. His split was simple: he takes 60% for putting the song out, the artist takes 40%. “That may sound like a lot, but you just made $100,000.” And every time the song is resold, the original artist gets 10%. “Without Sony, Apple, all these taking percentages.” His point is transparency. Every sale shows up in the artist’s wallet. No waiting for a statement from a label. His closing line: “You got to get a billion streams to get 45,000. You sell a hundred, and if you’re selling it for $10, you do the math.” The case for Spotify: it doesn’t pay artists directly. It pays labels and publishers, and they pay artists under their own contracts. Snoop’s $45,000 may only be one slice of what that billion streams earned. So who really got Snoop’s money: Spotify, the labels, or the contracts he signed?

Harrison Ford was paid about $10,000 to play Han Solo. Star Wars made over $300 million in its first release. Alec Guinness took a cut of the box office instead. Over his lifetime, it reportedly made him about $100 million. In the video below, Ford tells Good Morning America how he got the part, and what he said when he heard the offer. He wasn’t even auditioning. A producer friend got him to read lines with the actors trying out for Luke and Leia. He thought he was just doing George Lucas a favor. When it was over, they asked if he wanted to play Han Solo. His first question: “How much?” They said $1,000 a week. “And I said no.” Then he laughs. “But I did. I did it for $1,000 a week for the first one.” That came to about $10,000 for the whole film, reportedly. Alec Guinness, who played Obi-Wan, made a different deal: a $150,000 salary plus 2.25% of the gross. Star Wars became the highest-grossing movie in history at the time. Asked if his pay went up for the sequels, Ford smiles: “A little bit.” 38 years later, for The Force Awakens, he was reportedly offered up to $25 million upfront. The case for the studio: in 1976, Ford was a supporting actor with almost no leading roles. Nobody knew if a space movie would work, and $1,000 a week was a normal rate for an unknown. Guinness was already an Oscar winner, so he had the leverage to ask for a percentage. So was $1,000 a week fair for an unknown actor, or did Star Wars owe Han Solo more?

Matthew McConaughey turned down $14.5 million to make one more romantic comedy. A few years later, he won an Oscar for a movie made on $4.9 million. In the video below, he tells Steven Bartlett on The Diary of a CEO how the offer kept going up. In the 2000s, he was Hollywood’s go-to rom-com guy. The movies paid well, and the scripts kept coming. But he wanted dramas, and nobody would cast him in one. So he moved to his ranch in Texas and told his agent: no more rom-coms. His wife Camila was pregnant with their first child. For months, nothing came. He says he thought about becoming a teacher or going back to law school. Then an offer came in. $8 million. He said no. They came back with $12 million. No. Then $14.5 million. “Let me read that again.” He says it was the same script he had already turned down at $8 million. “But it was better written.” He still said no. His brothers asked him: “What is your major malfunction, little brother?” He believes that one “no” told Hollywood he was not bluffing. “He’s not for rent.” About 20 months after he walked away, the offers he wanted started coming in. Mud. Magic Mike. True Detective. Then Dallas Buyers Club. It was shot in 25 days on $4.9 million, and it won him the Oscar for best actor, a goal he says he had written down in 1992. The case for the skeptics: he already had years of rom-com money in the bank. Saying no to $14.5 million is easier when you can afford 20 months without a paycheck. Most people can’t. So was it courage, or a bet only a millionaire could afford to make?

Steve Jobs reportedly put $10 million into Pixar in 1986. Disney paid $7.4 billion for it in 2006. That sale price was 740 times his investment. Ten years before the sale, Jobs explained in an interview why Pixar gave its employees stock instead of contracts. In the video below, he walks through that choice, and the commercials business Pixar walked away from. He met Ed Catmull in 1985. Catmull ran the computer division at Lucasfilm. Catmull had a dream: the first computer-animated feature film. Jobs says he bought into it financially and spiritually. It took 10 years. Toy Story opened in November 1995. A week later, Pixar went public at a valuation of about $1.5 billion, the largest IPO of the year. Pixar also had a commercials unit. Jobs says it won almost every award in the business. It was work for hire. Pixar got paid once and shared none of the upside. His example: if a client sold more Listerine because of a Pixar ad, Pixar earned nothing extra. In 1996, Pixar pulled out. Twenty-five people had been working there. Hollywood keeps talent with contracts, Jobs says. Silicon Valley uses stock options. Pixar chose stock. He also says power flips in a studio like that: “the CEO is actually at the bottom.” The case for contracts: Jobs admits there are good reasons to lock people in for a film. If someone leaves mid-project, the studio is at risk. A contract guarantees the team. Stock only pays off if the company wins. Was Jobs right that stock beats a contract, or did it only work because Toy Story was a hit?

Arnold Schwarzenegger took no salary for Twins. The movie made $216 million. He says it paid him more than $40 million. More than any movie he has ever made, including The Terminator. In the video below, Andy Cohen asks which film earned his biggest paycheck, then starts guessing the number. He has said Universal doubted an action star could carry a comedy. So Schwarzenegger, Danny DeVito and director Ivan Reitman skipped their salaries and took a piece of the back end. The budget was under $20 million. Cohen asks: more than $20 million? “Much more,” Arnold says. More than $40 million? He says it was more than that. A sequel, Triplets, was planned, with Eddie Murphy as the third brother. It never happened after Reitman died in 2022. The case for the studio: it was betting on an action star in a comedy he had never done. Skipping salaries kept the risk low. Nobody expected the film to become his biggest payday. So did Universal protect its budget the smart way, or hand Arnold the best deal of his career?