In 1990, Vanilla Ice's "Ice Ice Baby" became the first hip-hop song to top the Billboard Hot 100. He says that money helped launch Death Row Records, after Suge Knight walked him onto a hotel balcony. In the video below, Ice describes what happened up there. "I got it. You don't have to hang me over." It started at dinner. A big man sat down at Ice's table and introduced himself as Suge Knight. "He starts eating some of my fries," Ice says. Three weeks to a month later, Ice walked into his Los Angeles hotel room. Knight was already inside with about five men. "Did I see guns? Yes, many of them." Knight took him to the balcony with a stack of papers about 300 pages thick. Ice signed over a few points on his album To the Extreme. He says they "turned out to be worth millions of dollars." The points went to Mario Johnson, a man Knight brought in as a co-writer. By Ice's account, Johnson got a $400,000 advance, and Knight took 25% as his manager. That's $100,000. For Knight, according to Ice, it was "the most money he'd ever made." A couple of weeks later, Ice recalls, Knight came back with two new clients: The D.O.C. and Dr. Dre. Then Death Row released The Chronic and signed Tupac. "I knew the funding came from my record," Ice says. "I'm happy to invest in that, even with no return on my money." Knight denies it. In 2015, he told ABC the deal was friendly and that Johnson wrote the song. Asked if he took Ice to the balcony to sign over the rights, he said: "No, I did not. Never happened." Who do you believe about that balcony: Vanilla Ice or Suge Knight?

In 1994, Pearl Jam wanted fans to pay no more than $20 for a ticket. Ticketmaster's $3.25 fee pushed the price past that line, and the band canceled its summer tour rather than accept it. In the video below, the band tells Congress who it was fighting for. "All the members of Pearl Jam remember what it's like to be young and not have a lot of money." Stone Gossard and Jeff Ament testified before a House subcommittee on June 30, 1994. Gossard said part of Ticketmaster's fee went back to promoters and venues and blamed "this incestuous relationship and the lack of any national competition for Ticketmaster." Asked whether Ticketmaster was entitled to a profit, the band answered: "I think our main concern is, are we entitled to use a different company other than Ticketmaster?" Aerosmith's manager told the subcommittee what Steven Tyler had said to him: "Mussolini may have made the trains run on time, but not everyone could get a seat on that train." Ticketmaster said it had offered, through promoters, to cut the fee to $2.25 or $2.50, depending on the area. It blamed the band: "They said this was it, take it or leave it." Pearl Jam wanted $1.80. The gap was 45 to 70 cents a ticket. The next year, the band sold a tour through a smaller company and canceled half the dates. Eleven days later, the Justice Department closed its investigation without filing a case. On April 15, 2026, 32 years after the testimony, a jury found that Live Nation and Ticketmaster had illegally maintained a monopoly and that fans in 22 states had overpaid an average of $1.72 a ticket. Live Nation is contesting the verdict. Who cost the fans the 1994 tour: Pearl Jam or Ticketmaster?

In 2010, NBC agreed to pay Conan O'Brien roughly $33 million to leave The Tonight Show. He had waited five years for the job and held it for less than eight months. In the video below, Conan discusses reports that ending Jay Leno's contract could have cost NBC up to $150 million. "If you're General Electric, the decision's probably pretty clear." In 2004, the network announced that Conan would replace Jay Leno in 2009. But when the handover happened, NBC kept Leno and gave him a separate show at 10 p.m. Ratings for Leno's new show disappointed local stations, while Conan trailed David Letterman. NBC decided to move Leno back to 11:35 p.m. and push The Tonight Show to 12:05 a.m. Conan refused, arguing that moving past midnight would damage the show itself. After negotiations, NBC agreed to pay him roughly $33 million and his staff another $12 million. Conan understood the financial logic but rejected NBC's account of his performance. Asked whether he had been given a fair chance, he answered: "Absolutely not." When NBC claimed his Tonight Show was on track to lose money, he said: "It's really not possible." He also questioned Leno's return. "He went and took that show back," Conan said, explaining that he would not have done the same if their roles had been reversed. Around 50 stagehands and other crew members received nothing from NBC under the settlement. Conan paid them at least six weeks of severance out of his own pocket. Did NBC keep the better host, or the one it would cost more to let go?

If you had invested $2 every day in Tesla stock instead of coffee at Starbucks

In January 2002, Mark Cuban took a public shot at the man in charge of every NBA referee. The league fined him $500,000, a record at the time. The video below has the whole story. Cuban's line was: "Ed Rush might have been a great ref, but I wouldn't hire him to manage a Dairy Queen." Cuban paid the fine. Then he gave another $500,000 to charity, matching the league dollar for dollar. Dairy Queen answered with an invitation to work a shift. Three days later he was behind the ice cream machine, and a student newspaper reported that almost 2,000 people showed up. The insult cost him $1 million. Millions of TV viewers heard his name, and the media split over him. Years later, fined $15,000 for cursing at a charity gaming event, he asked if cursing again meant another fine, then did it anyway. "It was worth it," he said. Was the Dairy Queen line a $1 million mistake, or the best money he ever spent on attention?

At 30, Mark Cuban sold his first company for $6 million. The first thing he bought was a $125,000 lifetime pass to fly first class on American Airlines. In the video below, he tells the story. His dad reupholstered car seats, his mom did odd jobs, and when he started that company, he was sleeping on the floor of an apartment he shared with five other guys. He gave $1 million to employees. After his partner's share and taxes, about $2 million was his, and his goal was to retire by 35. He wasn't into cars, but he flew so often that he knew American Airlines' number by heart. The night the checks came in, he called them drunk from an Italian restaurant: "Do you guys sell lifetime passes?" They did. "I spent 125 grand of my 2 million," he says. The rest went to a friend at Goldman Sachs to invest "like an old man." Cuban was ready to live "like a student" and never work again. He never stopped working. Years later, he gave the pass to a friend because he had his own plane. $125,000 right after his first big sale: reckless, or exactly what he built the business for?

By 1995, Forrest Gump starring Tom Hanks had grossed $661 million worldwide. Paramount told novelist Winston Groom, entitled to 3% of net profits, that the film had lost roughly $62 million through the end of 1994. Groom received $350,000 for the rights, with more to come if the film generated net profits. Hanks negotiated a share of gross receipts, so his payments did not depend on what remained after expenses. After theaters took their share, Paramount charged a distribution fee of 32% of its receipts. Advertising, production, overhead, financing interest and payments to Hanks and director Robert Zemeckis further reduced the balance available to net-profit participants. In the video below, Hanks explains how he and Zemeckis personally paid for the cross-country running sequence the studio wanted to cut. In exchange, they negotiated a larger share of the film’s proceeds. In 1995, after threatening legal action, Groom resolved the dispute and signed a seven-figure deal for the sequel rights. This time, his share would be calculated before expenses. The studio collected its distribution fee while reporting a loss for net-profit participants. Did Groom negotiate badly, or was Paramount offering a share of profits its own fees could erase?

In 1989, John Madden turned down the chance to buy EA stock at $7.50 a share. By his death in 2021, the game series bearing his name had generated at least $4 billion in revenue. He called his refusal the dumbest decision of his life. In the video below, Madden explains that he envisioned the game as a tool for teaching American football: “When we started, we had no idea what it was going to be.” EA proposed seven players per side because of technical limitations. Madden insisted on full teams: 11 against 11. Otherwise, he would not put his name on the game. When the game finally launched, EA founder Trip Hawkins offered him the chance to buy shares at the IPO price. According to ESPN, Madden replied: “I gave you my time. I’m not giving you my money.” The Sega Genesis version became a hit, and new editions followed every year. The series brought in sports fans who had never been interested in video games. According to ESPN, EA shares reached $70 by 1999, up from $7.50 in 1989. Madden earned money from the games, but passed up the opportunity to profit from the company’s growth as a shareholder. Did Madden underestimate the business he helped build, or does refusing to invest his own money only look like a mistake because we know how it turned out?

In 2007, Matt Damon said no to the lead role in Avatar and 10% of its profits. Later, at Cannes in 2021, he summed it up in one sentence: "You will never meet an actor who turned down more money." In the video below, he tells the story himself. James Cameron made the offer himself. Damon says Cameron told him he didn't need a star and could cast an unknown instead. Damon was committed to a Bourne movie and didn't want to let that team down. The role went to Sam Worthington. Avatar became the highest-grossing film in history, at about $2.9 billion. GQ estimated his 10% at around $250 million. Damon jokes about it: "I turned down Jim Cameron. What an idiot." But he says he doesn't regret his choices, because "everything shapes who you are." Would you have kept your word to the Bourne team, or taken the $250 million?

In March 2026, Netflix bought Ben Affleck's AI company for about $587 million in cash. Affleck says he writes "pretty sh*tty Python scripts." So what did his team build that Netflix paid for? In the video below, he explains how visual effects work led him to machine learning long before the deal. Before Artists Equity, Affleck ran a small VFX company. Colleagues told him to look at what Google and OpenAI were building. He started calling people with a simple question: "Hi, I'm Ben Affleck. Can I just come in and see what you're doing?" What he saw scared him. But he also saw a problem any director would recognize. The models could generate convincing video, but they gave no reliable control over it. A film needs consistent shots and precise edits, not one more impressive image. He quietly founded InterPositive in 2022: "I didn't tell anybody about it." Most video models had been trained on his peers' work, so his team shot its own footage on a controlled soundstage. The system builds a model from a specific film's own footage. Crews can use it to adjust lighting, replace backgrounds and add visual effects. Netflix took over the 16-person team and made Affleck a senior adviser. The price was disclosed in July. How much Affleck personally received was not reported. The interviewer asked him about the theory that Netflix bought the company to "provide cover for all the despicable things" it planned to do with AI. Affleck called it "a very cynical view indeed" and says films using his tools employ the same number of people or more. Is Affleck giving filmmakers more control, or helping Netflix replace the people who do this work today?

Mark Zuckerberg paid about $14 billion to put a man who had never trained a frontier model in charge of Meta's AI lab. His explanation: "Alex is the guy. Like, he's the f*cking guy." In the video below, he explains why. A lot of people asked if "the social media guy" and "the data guy" could really build a frontier lab. Wang's first meetings at Meta didn't help: "Oh, no, I've joined the wrong company." Zuckerberg says he didn't look for an expert in the latest technique. He wanted "a clear thinker" who updates "as kind of an entrepreneur would." Just over a year later, "the data guy" shipped a model puts Meta at the frontier. Did Zuckerberg get lucky, or did he see something everyone else missed?

Mark Zuckerberg was ready to spend up to $200 billion on an AI model nobody at Meta had seen. "We haven't seen the models yet. You know, we're going to write this check for like, I don't know, like $100 billion, $200 billion." In the video below, he tells the story with Alexandr Wang, the man he hired to build it. It started in April 2025. About two weeks after Meta launched Llama 4, Zuckerberg began calling people for advice on what to do. He paid about $14 billion for 49% of Wang's company, Scale AI, and put Wang in charge of a new lab. Wang had never trained a frontier model. His first advice was that you don't need a lot of people, just very good ones. By the end of 2025, Wang had a "vibe report" and a few plots. At an executive offsite in Hawaii, Meta's CFO Susan Li kept pulling him aside: "I really need to impress on you that this model has to work. It has to be good. If it's good, it's all good. We're great. But if it's bad, it's really, really, really bad." He kept building. Meta's cluster in Ohio passed a gigawatt, and a 5-gigawatt one is going up in Louisiana. Zuckerberg puts the cost of running one gigawatt for a year at around $15 billion. On October 12, 2026, Meta released the model, Muse Wonder. Zuckerberg says it brings Meta to the frontier. His CFO warned the model had to work. Zuckerberg's view was that for the money to be lost, "AI overall has to fail." Was it a reckless check, or a calculated one? Would you have signed it on a vibe report?

In 1976, Ronald Wayne gave up 10% of Apple. The document recording his exit shows $800. He feared that staying in a partnership with Steve Jobs would cost him everything he already had. In the video below, Apple's third co-founder explains why he left less than two weeks after signing the partnership agreement. Wayne was 41. Jobs was 21, Steve Wozniak 25. Wayne wrote the agreement and drew Apple's first logo. The two Steves got 45% each. His 10% gave him the deciding vote in their disputes. Each partner was personally liable for the partnership's debts. Wayne had something to lose. Jobs and Wozniak had almost nothing. Jobs had borrowed $15,000 for parts to fill Apple's first big order. If the buyer didn't pay, the creditors could come after Wayne. On April 12, Wayne left the partnership. He later received another $1,500 for giving up any future claims. At a $4 trillion valuation, his 10% would be worth $400 billion. But only if it had never been diluted and he had never sold a share. He told CNN he had no regrets: he admired Apple, but believed he would have been unhappy working there. Would you have put your own assets on the line for the debts of a 21-year-old and a 25-year-old in exchange for 10% of Apple?

Tobey Maguire won more than $300,000 playing poker against a hedge-fund manager. Then it emerged that the man had been losing money stolen from relatives and friends. In 2011, a bankruptcy trustee came after the actor's winnings. In the video below, Molly Bloom describes Maguire's appetite for beating people at her table. She recalls him saying: "It's not really about money. It's more about crushing souls." One of the players was Bradley Ruderman. He ran Beverly Hills hedge funds and raised more than $44 million, promising annual returns as high as 60%. His investors received statements showing profits. Ruderman later admitted losing $5.2 million of their money in private poker games. The complaint against Maguire included $110,000 from a single hand in 2007. Ruderman's clients weren't being told about those losses. In December 2008, he wrote to them condemning Bernie Madoff and promising that "such disgraceful practices will never happen under my watch." He was stealing their money as he wrote it. The funds collapsed in 2009. Ruderman pleaded guilty to fraud and received more than ten years in prison. The trustee pursued the players to recover money for his victims. The lawsuit sought $311,300 from Maguire. He denied wrongdoing and agreed to settle for $80,000. Some victims had known Ruderman since childhood. They had welcomed him into their homes and trusted him with their money. Some of that money ended up paying people who beat him at cards. Maguire didn't know where the money came from. But once he found out, was returning $80,000 enough when the lawsuit sought more than $300,000?

India's telecom minister sued his own father and grandmother before he turned 20. Jyotiraditya Scindia wanted the family's royal inheritance to go to him alone. At stake: 623 kg of gold, 332 kg of silver, palaces and land. The inventory of movable assets alone filled 300 pages. His claim rested on an old royal rule: the eldest son inherits the estate. His aunts demanded their shares. A disputed will attributed to his grandmother excluded both him and his father. The family fought for roughly 40 years. Some relatives died before the cases ended. Their children replaced them in court. By 2026, a settlement was finally taking shape. Then came Elon Musk. On October 9, he addressed Mukesh Ambani as "Dear Prime Minister Ambani" and accused him of blocking Starlink to protect his business. Scindia once argued in court that the entire royal inheritance should belong to him alone. Now he's responding to Musk's monopoly allegations. In the video below, his answer is: "India does not allow a monopoly in any sector."

Before Chris Gardner became a multimillionaire, he sometimes had to choose between feeding his son and paying for a hotel room. They ate, then slept in a train station bathroom. In the video below, the man whose life inspired The Pursuit of Happyness recalls raising his son while homeless. Gardner was 28. His boy was 14 months old. After their relationship ended, the boy's mother asked Gardner to take care of him. His boarding house did not allow children, and his income as a brokerage trainee could not cover a home for them both. Gardner had grown up with a violent stepfather who told him, "I am not your daddy." As a child, he had promised himself his own children would always know their father. They stayed in shelters and cheap hotels when they could. On other nights, they rode trains or slept in public washrooms, where Gardner bathed his son in the sink. Sex workers who saw him pushing the stroller began giving him $5 bills. He says there were times he could not have fed his son without their help. At Dean Witter, he made 200 calls a day while keeping his homelessness from colleagues. A visiting Bear Stearns partner noticed his work and eventually offered him a job. Gardner asked for $5,000 a month. The partner guaranteed it for a year and gave him a month's advance to buy clothes. Gardner went on to found Gardner Rich in 1987 and become a multimillionaire. But he still keeps the key to the home he found after being homeless. There was no furniture when they moved in. He remembers telling his son: "We got a key now. We're home." Why do we admire fathers like him when their stories become movies, yet so often walk past them when they need help?

Elon Musk was fired from the company that became PayPal while he was flying to his honeymoon. The stake he kept later brought him about $180 million after tax. In the video below, Musk explains why he chose not to fight the men who removed him and how he later rebuilt those relationships. In March 2000, X.com merged with Peter Thiel and Max Levchin's Confinity, and Musk became CEO. He wanted X.com and Windows. Much of the team wanted PayPal and Unix. The product was still crashing. That September, Musk finally flew to Australia for a delayed honeymoon during the Olympics. While his plane was in the air, Levchin, Thiel, Reid Hoffman and David Sacks delivered letters of no confidence to the board. The board removed Musk. Thiel became CEO, and the company was later renamed PayPal. Musk said, "I could have fought it really hard," but decided it was "best to sort of concede" while the company was at a critical point. He kept his stake. When eBay bought PayPal in 2002, Musk put almost all of the payout into SpaceX and then Tesla. Isaacson wrote that Musk first thought about revenge, then decided the coup had saved him. But Musk still added: "Of course, if I had stayed, PayPal would be a trillion-dollar company." Did the coup save Musk, or did PayPal lose the man who says he would have made it a trillion-dollar company?

In 2006, Warren Buffett pledged Berkshire shares worth about $37 billion to charity. That same year, he told Nicole Buffett, who had called him Grandpa since childhood, that she was not his granddaughter. The message came in a letter. "I have not emotionally or legally adopted you as a grandchild", Buffett wrote. He signed it "Warren." A year earlier, he had signed a card “Grandpa.” Nicole was four when her mother married Buffett’s son Peter. Peter later legally adopted Nicole and her twin sister. She grew up visiting Buffett in Omaha and spending family holidays with him. His late wife Susan named Nicole one of her "adored grandchildren" in her will. Nicole knew she would not inherit Buffett’s fortune. He paid for her education and living expenses while she studied. After graduation, she supported herself through her art and also worked for another wealthy family, organizing their home and helping care for their children. Then she appeared in Jamie Johnson’s documentary The One Percent and spoke publicly about wealth, the Buffett family, and feeling excluded from its philanthropy. Buffett believed she had exaggerated their closeness and used the family name without warning him. The letter followed. In the clip below, Nicole holds photographs of herself and her sister as little girls. She remembers the months and years spent at Buffett’s home. Then she reads the sentence saying she had never really been part of his family. At the same time, the world was celebrating Buffett’s pledge to give five foundations Berkshire shares then worth about $37 billion. Buffett had every right to leave Nicole no inheritance. His letter went further. It denied the family relationship itself. Nicole described the divide in one sentence: the public Warren Buffett and Warren Buffett as a grandfather were "two completely different things."

In September 2025, 81-year-old Oracle co-founder Larry Ellison briefly became the richest person in the world. His adoptive father used to tell him he would never amount to anything. His mother was 19 and unmarried. At 9 months he was adopted by relatives in Chicago. At 12, he was told at the door: meatloaf for dinner, and by the way, you're adopted. Ellison shares his childhood memories in the interview below. His adoptive father, a Russian immigrant, lived by "my country, right or wrong" and didn't want his son questioning authority. Ellison later called the authority figures of his childhood "wonderful examples of how not to be." He found his biological mother only at 48. After they met, he said his real family was the people who raised him. The man who told him he would never amount to anything was part of that family. Could you call someone family after hearing that from them?

On December 8, 1980, a San Mateo County child support case required 25-year-old Steve Jobs to pay $385 a month for his daughter Lisa. Four days later, Apple went public at $22 a share. Jobs was suddenly worth $217 million. He had been denying she was his since the day he met her. "It's not my kid," he told everyone on the Oregon farm where she was born. In a sworn deposition he said he was sterile and named another man as the father. The DNA test came back above 94 percent. Two years later he told Time that 28 percent of American men could be the father. Apple even had a computer called the Lisa. For years he said it wasn't named after her. She was 27 when Bono asked him over lunch: "So, was the Lisa computer named after her?" Jobs looked down at his plate for a long moment. "Yeah, it was." "That's the first time he's said yes," she told Bono. Lisa had asked him the same question in high school. He said, "Nope." Then: "Sorry, kid." Near the end of his life, Jobs cried and told her he was sorry. He wished he had spent more time with her. It was too late to change it, he said. Then he repeated one sentence: "I owe you one." It took him more than 30 years to say it. By then there was almost no time left. If you were Lisa, would that apology have been enough?