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?