Ryomen

He was found unconscious in a Nevada brothel after spending $75,000 there in four days. Police suspected an overdose of cocaine and other drugs, and doctors told his family to say their goodbyes. In October 2015, that man was Lamar Odom, a two-time NBA champion with the Lakers. In the video below, he tells Shannon Sharpe the part most people never heard. “I ain’t even do drugs that night.” He says he was mad because he had no cocaine to bring. He had a drink, there were girls around him, and he woke up three days later in a hospital, tearing tubes out of his neck. He shows the scars. Why was he there at all? He had just signed divorce papers with Khloé Kardashian. That, he says, is what took him to the brothel. She showed up at the hospital anyway. Shannon says not a whole lot of women would have done that. Lamar agrees that she did. When he first woke up he couldn’t walk or talk, and he had to learn both again. Then the count. 12 strokes and 6 heart attacks. He says he was pronounced dead twice. Khloé pulled the divorce filing and stayed by his side while he recovered. A year later they divorced for good. She had already signed the papers. Did she owe him anything?

In July 2015, 50 Cent filed for bankruptcy, days after a jury ordered him to pay $5,000,000 over a sex tape he had posted online. Then he went on Instagram and posted himself biting into a sandwich made of cash. In the video below, Conan O’Brien shows him the photos one by one. A fridge full of money, a coffee table made of money, the word BROKE spelled out in bills, and cash falling out of his pants. In March 2016 his lawyers had to file papers telling the bankruptcy court that the money in the pictures was props, and that standing next to something did not mean he owned it. 50 Cent tells Conan his audience doesn’t understand the difference between Chapter 11 and Chapter 7. Chapter 11 is a reorganization, he says, and he had four companies with $3,000,000 or $4,000,000 in each. His other big debt was about $17,000,000 owed to Sleek Audio, a headphone company that won a case against him. He says that once you’re successful and famous, you become a bullseye. Lawyers work on contingency and sue you for anything. In July 2016, the judge approved his plan to pay creditors about $23,000,000 over five years. This is the same man who reportedly made around $100,000,000 when Coca-Cola bought Vitaminwater in 2007. Was he broke, or was he protecting his money?

Michael Vick signed a $130,000,000 extension with the Atlanta Falcons in December 2004, then the richest contract in NFL history. Three years later investigators found a dogfighting operation at his house on Moonlight Road in Virginia, and the friends charged with him agreed to testify against him. By July 2008 he was filing for bankruptcy from prison, with debts listed between $10,000,000 and $50,000,000. In the video below, Vick tells DJ Vlad where the money went, and who he says took it while he was locked up. He says he never spent crazy. A $3,300,000 house, financed. A Nike deal worth a couple million a year, his own shoe, his own apparel line. His problem, he says, was simple: "You can't listen and understand a financial advisor if you don't have financial literacy." So he bought what he calls a whole city. About 12 acres in Union City, Georgia, with strip malls, a movie theater and restaurants. Then came the bankruptcy. "I never found out what happened to it." His wife had warned him about the bad apples in his circle. Law enforcement warned him that state troopers were watching the house. He kept them around. The judge gave him 23 months. The Falcons cut him. His answer: "I would have dropped me too." Then the banks came. Millions here, millions there. He says he handed an advisor enough money to clear everything while he was inside, "but people go missing." In 2011 the Philadelphia Eagles gave him a new $100,000,000 deal. He later paid back what he owed creditors, about $17,600,000. He calls his sentence fair. He says he thought he was above the law. Was Michael Vick robbed by the people he trusted, or did he lose $130 million the day he decided nobody was watching?

Magic Johnson says that at 19 he turned down Nike stock and took the cash from Converse instead, about $100,000 a year. He says that stock would be worth around $5,000,000,000 today. In the video below, he explains the exact moment he realized how badly he had messed up. In 1979 he had just beaten Larry Bird for the national title, and every shoe company in America came after him. Converse offered the most money. Magic says when you're black and broke, you take the most money. Then Phil Knight walked in. Nike was still a young company. Knight told him he couldn't match Converse, but he could give him something called stock. Reports say the offer was $1 for every pair of shoes sold, plus 100,000 shares. Magic passed. He says he knew nothing about stock, and nobody in his family did either. He realized his mistake when Michael Jordan came out with Air Jordan. Jordan took the Nike deal in 1984. Forbes now values Jordan Brand at more than $10 billion. Magic has said he still gets mad every time he walks into a Nike store. He made up for it. After basketball he built a business empire, and he now owns pieces of the Dodgers and the Commanders. Nike and Phil Knight have never confirmed the details of the offer. Would you have taken $100,000 a year at 19, or bet on stock in a company nobody had heard of?

Comedy Central offered Dave Chappelle $50,000,000 to keep making Chappelle's Show. He walked out in the middle of season 3 and flew to South Africa. In the video below, he tells David Letterman why the extra $40,000,000 was never worth it to him. Chappelle's Show had been on for 2 seasons and was one of the biggest shows on cable. Its first season became one of the best-selling TV DVDs ever. The new deal was huge: about $50 million for 2 more seasons. Chappelle agreed. Then the show stopped, and it never came back. Almost 10 years later, Letterman asks if he regrets it. Chappelle says technically he never quit. He's just "7 years late for work." Then he explains the math. He's in a nice restaurant with his wife, and he sees a guy across the room with $100 million eating the same entree. Say Chappelle has $10 million in the bank. The difference in lifestyle is tiny. The only difference between $10 million and $50 million, he says, is "an astounding $40 million." He admits he'd like to have that money. Money is the fuel for choices. But some of the most valuable things in his life weren't bought with it. In 2016 he came back on his own terms. Netflix reportedly paid him $60 million for 3 specials. Would you walk away from $50,000,000 if the job was breaking you, or take the money and figure it out later?

In the 33 months after he got out of prison, Mike Tyson spent $4,500,000 on cars and motorcycles and another $240,000 a month in walking-around money. He also put more than $400,000 into pigeons and cats, and bought himself a house with 38 bathrooms. In the video below, he hears those numbers one by one, and he can barely believe them. He reportedly gave cars to 15 women and 2 men. He once crashed his Rolls-Royce and told the police to keep it. He made around $400,000,000 in his career, the interviewer says. Tyson answers that it could have been. He still filed for bankruptcy, owing about $23,000,000. His explanation is short. He was reckless, young and foolish, and he has an addictive personality. Then he compares it to drugs. You can have everything, he says, and still feel an empty hole, so you keep spending to fill it. The hole has no bottom. He still can’t say what he was trying to fill. He asks himself what the late 90s were even about. What was he so angry about? Why was he so depressed? Why did he bite Evander Holyfield’s ear? He doesn’t know what he wants now. He only knows he doesn’t want what he already had. Was it the money that broke him, or was he already broken when the money came?

Macaulay Culkin’s father skipped his own custody trial over a son who had earned $4,500,000 for a single movie. Then he vanished for about 4 years, and reappeared with a telegram on the night his son went back to work. In the video below, Culkin explains why that telegram told him everything. The trial was the end of it. His father simply didn’t show up, and the case was over. No goodbye, no explanation, no birthday calls, no Christmas. Before that, Culkin says, there was violence. Once his father hit him across the face, knocked him to the floor and told him to get up and fight. He refused, took another hit, locked his door and called the police. He also says nobody ever told him his parents had never been married. He found out from a TV news report in the middle of their custody fight. Then came opening night of his stage comeback. The telegram wished him luck and a long and successful run, and said he would, as always, be wonderful. It was signed Dad. Culkin says he didn’t want contact. What struck him was the timing. His father stayed silent for years and only reached out once his son was working and back in the spotlight. Culkin had already gone to court to remove his parents’ names from his trust fund, reportedly worth $15,000,000 to $20,000,000. Is a parent who only calls when you’re making money still calling for you?

Shaquille O’Neal says he walked away from a $40,000,000 Reebok deal because a woman outside an arena yelled at him. He says the shoes he made instead have now sold more than 400,000,000 pairs. In the video below, he explains what that woman said to him. He was leaving the arena when she started screaming at him for charging kids so much money for sneakers. He had about $2,000 in his pocket and tried to hand it to her. She smacked the money out of his hand. Then she asked him why nobody made a shoe that regular families could afford. He says he thought about it and decided she was right. That same day, he says, he cut ties with Reebok and told them to keep the money they still owed him. He took his idea to Walmart and launched the Shaq brand at $19 to $29 a pair. His insight was about kids. They don’t mind wearing $20 shoes, he says. They mind wearing shoes that look like they cost $20. So he brought in designers who had worked on his Reebok shoes and told them he didn’t care how much money he lost, as long as the kids looked good. Back in 2016, Shaq said the brand had sold over 120,000,000 pairs. Was walking away from $40,000,000 the worst decision of Shaq’s career, or the smartest one?

Искал в интернете, запущен агент, выполнил команду In 2021, MLS hit David Beckham’s Inter Miami with a record $2,000,000 fine for breaking salary rules and hiding parts of player contracts. Two years later, the same club signed Lionel Messi, and Forbes now values it at about $1,200,000,000. In the video below, Beckham explains how he kept chasing Messi through all of it. The league also cut $2,271,250 from the club’s allocation money and suspended its sporting director. Beckham’s partner Jorge Mas was fined another $250,000. Beckham says there were so many obstacles over 10 years of trying to build the team that sometimes it looked like it would never happen. Around 4 years before Messi arrived, he sneaked into the Barcelona hotel of Messi’s father for a meeting. Neither side was ready, but Beckham told the dad that Miami wanted his son whenever he was. When Messi finally left PSG, he also had offers from Saudi Arabia and a chance to return to Barcelona. Beckham says Barcelona scared him most, because Messi never got a proper goodbye there. He found out Messi chose Miami at 5 in the morning in Japan, when his phone started blowing up. His original right to buy the team cost $25,000,000, written into his 2007 LA Galaxy contract. Did Beckham build a $1,200,000,000 club, or did Messi rescue one that was in trouble?

Alex Rodriguez says that after he retired, his income fell about 90%, from $30,000,000 a year to $3,000,000. In 2018, he was still paying his ex-wife roughly $155,000 a month in spousal and child support, and he went to court to cut it. In the video below, he talks about what that kind of money did to him long before the bills came due. He signed a $252,000,000 contract at 25, the richest deal in sports at the time. He says success that early shrinks your self-awareness and grows your ego, and he didn’t have the tools to handle it. He and Cynthia Scurtis divorced in 2008. A decade later, he argued she now had a new fiancé, 3 homes and millions in the bank. He reportedly offered $20,000 a month for their 2 daughters. She reportedly wanted $50,000. Then her brother came after him too. Constantine Scurtis, his former real estate partner, sued him for $50,000,000, claiming Rodriguez cut him out of the business they built together. Rodriguez countersued, saying Scurtis took $1,400,000 from the partnership without permission. Rodriguez says he has now been in therapy for more than 10 years, and that it saved his life. When a fortune comes this early, is the biggest risk spending it, or the people who expect a share of it later?

Stephen A. Smith says ESPN once offered him a little under $2,000,000 a year for 3 years, and he turned it down. In 2025, ESPN gave him a 5-year extension worth at least $100,000,000. In the video below, he explains how saying no to that first offer almost ended his career. He had his own show on the network, with more than 300 episodes, and fans screamed his name in arenas. He thought that kind of popularity equaled dollars. ESPN had the data, and he didn’t. The network knew he had nowhere better to go. So it made what it considered a fair offer and stopped there. He says he expected the talks to keep going. Instead, they shut down, his airtime shrank, and about a year later he was let go. It happened shortly after he became a father. He lived off his savings with no income, afraid he would never be allowed back and couldn’t take care of his baby daughters. His conclusion is harsh. If you don’t understand your own business, he says, you don’t deserve more than what you’re offered. It’s your job to know your worth and prove it in their eyes. Looking back, he says he would have taken the deal. Did Stephen A. Smith lose because he asked for too much, or because he walked into the room knowing less than the people across the table?

John Daly won 2 majors and had earned about $8,700,000 in PGA Tour prize money by 2006. When he and his co-writer went through his tax records for his book, they found he had lost $55,000,000 to $57,000,000 gambling. In the video below, he explains how that number happened. He says he expected 20 or 25 million. The real figure works out to about $3,200,000 a year from 1991 to 2007. At blackjack, he played 7 hands at once, at $5,000, $10,000 or $15,000 a hand. One casino had $5,000-a-pull slot machines, and he played those too. After losing a playoff to Tiger Woods, he lost $1,650,000 in 5 hours, mostly on those slots. He says he once sat at a slot machine for 2 days straight and played blackjack for a day and a half, getting up only to use the bathroom. He has been up $4,000,000 to $5,000,000 in a night and walked out down $2,000,000, because he wouldn’t stop. His biggest mistake, he says, was walking in with $1,000,000 to $3,000,000 casino credit lines and thinking he was going to win. He says he doesn’t regret it. He had fun, and now he plays $25 slots. Is $55,000,000 a fair price for the fun John Daly says he had, or did the casinos win the only game that mattered?

Mike Tyson says Don King brought fight contracts to him in prison, and he signed them from his cell. He went on to earn an estimated $300,000,000 to $400,000,000 in his career, and still filed for bankruptcy owing about $23,000,000. In the video below, he explains what happened to him after the money was gone. Tyson served 3 years in prison. He admits he behaved badly inside, fighting guards and getting sent to the hole until more time was added to his sentence. Within 11 months of getting out, he held 2 title belts again, and he says his ego came right back with them. In 1998, he sued King for $100,000,000, claiming King had cheated him out of millions. They settled in 2004 for $14,000,000. Tyson says losing everything sent him into drugs, drinking and shame so heavy he wanted to die. He went through AA and started over with nothing but experience. Now, he says, nobody in his family gets anything for free. Not even his kids. They have to work and earn their inheritance. The case was settled out of court, and King never admitted cheating him. Did Don King take Mike Tyson’s money, or did Tyson spend a fortune nobody taught him to keep?

In 1983, Steve Jobs told a design conference in Aspen that getting computers into society would take about 15 years. In 1998, 15 years later, Apple launched the iMac and posted $309 million in profit, its first profitable year since 1995. In the video below, Jobs explains why he saw the computer as a new medium, even though sending a drawing across town still meant dialing a phone number. “Computer programs have no physical manifestation at all,” he said. “They’re simply ideas expressed on paper.” He couldn’t draw, he admitted. But he could paste a picture into a document and mail it to someone in Aspen who dialed in to read it. What excited him wasn’t the gadget. Television could only replay an experience. A program captured the rules behind it, so it could create thousands of different experiences that all follow the same laws. So he pointed to a kids’ game called Hamurabi. A seven-year-old gets 1,000 bushels of wheat, 100 people and land at 24 bushels an acre. Plant too little, and next year people starve. He applied the same thinking to learning. Books kept him going in school, he said, but you can’t ask Aristotle a question. Someday, he hoped, a machine could carry someone’s way of thinking so we could ask it what Aristotle would have said. Then he named the stakes. The next 15 years could be done great or just so-so, and Apple was trying to do it great. A video replays one moment. A model lets you live a thousand versions of it. If you could practice your money decisions in a simulation first, which one would you test before making it for real?

Molly Bloom says she made $4 million to $6 million a year in tips running private poker games. In 2013 she was arrested, and in 2014 a judge gave her probation, community service and a $125,000 forfeiture. Her tables included Ben Affleck, Tobey Maguire and Leonardo DiCaprio, along with heads of major banks, movie studios and politicians. In the video below, she explains where the money came from, and why she threw out one of the best players. “From the winners,” she said. “If they won, they would tip a percentage, one to five percent of their wins.” She once watched someone lose $100 million in a single night. Dan Bilzerian showed up playing a clueless trust fund kid, she says, and “people bought it.” She saw through it. “You’re going to take everyone’s money,” she told him. “You’re bad for business.” So the best player at the table had to go. Her income depended on rich losers coming back every week, and a shark would empty the room. Then the business picked up a partner it never wanted. Italian organized crime demanded a piece of her New York games. She declined “in business terms” and stopped taking their calls. A man showed up at her apartment, put a gun in her mouth, beat her and emptied her safe, down to things from her grandmother. “I think your answer will be different next time,” he said. The house never needs to win a hand. It needs the game to keep going. With your own money, are you the player at the table, or the one collecting a percentage from it?

In 1980, Apple went public and Steve Jobs became a multimillionaire. Around then, a court case over a daughter he denied was his ended with him paying $385 a month in child support. After the IPO, he raised it to $500. Her name is Lisa Brennan-Jobs. Apple named a computer after her while Jobs publicly insisted it stood for something else. In the video below, she describes what those years looked like from the back seat of her mother’s car. In 1983, Time magazine quoted Jobs arguing that “28% of the male population of the United States could be the father.” Her mother read that article. “We had no money,” Lisa says. She was three or four. They were driving home in the rain, lost, and her mother started screaming, not at her but “at the world,” and slammed the dashboard. “Her feeling of hopelessness and her rage was terrifying.” Decades later, Lisa went to see her father before he died. He apologized fiercely, crying, and kept repeating one phrase: “I owe you one. I owe you one.” She didn’t know how to make sense of it. So she told him that if there are multiple lifetimes, “maybe next time we could be friends.” She meant it as a kindness, and as a way to name her frustration. They had been good as friends, she explains. “We liked each other. We would laugh together. It was fun when we were young.” In 2018 she published a memoir about all of it, Small Fry. By the end, he could afford almost anything. The debt he kept repeating was the one money couldn’t settle. What do you owe someone that no amount of money could pay back?

In 1976, Apple sold its first computer for $666.66, and Steve Jobs knew exactly what each one cost to build in the garage. A few years later, inside a real factory, Apple’s accountants were guessing. They used something called a standard cost: set an estimated number, then adjust it with a “variance” at the end of each quarter. In the video below, Jobs explains why he spent six months digging into that rule even though everyone told him it was just the way it’s done. “The reason you do it is because you don’t really have good enough controls to know how much it costs,” he said, “so you guess, and then you fix your guess at the end of the quarter.” In the garage, they knew the cost of every Apple I. In a factory worth millions, nobody did. And nobody asked why. “Nobody knows why they do what they do,” Jobs said. “Nobody thinks about things very deeply in business.” So when Apple built an automated factory for the Macintosh, it threw out the guesswork. It could tell exactly what something cost, “to the second.” He applied the same thinking to learning business itself. Much of it, he said, is folklore, things “done because they were done yesterday and the day before.” Ask enough questions and work hard, and “you can learn business pretty fast.” Most household budgets run on a standard cost too. A rough monthly guess, quietly corrected when the card statement arrives. A guess you fix every quarter feels like control. Knowing the real number is control. Do you know what your last month actually cost, or are you still adjusting a guess?

In fiscal 1997, Apple lost $1.05 billion. In fiscal 1998, it made $309 million, its first profitable year since 1995. In between, Steve Jobs spent months killing projects that Apple’s own engineers loved. In the video below, he explains why he cut a technology called OpenDoc even though, as he admitted, it did things nothing else could. “You’ve got to start with the customer experience and work backwards to the technology,” he said. “You can’t start with the technology and try to figure out where you’re going to try to sell it.” Nobody bought a LaserWriter for the Canon engine inside it. They bought it for the page that came out. Jobs knew how tempting the other way is. “I’ve made this mistake probably more than anybody else in this room,” he said. “And I’ve got the scar tissue to prove it.” So OpenDoc went, even though a developer stood up in front of the room and told Jobs he didn’t know what he was talking about. “I’m sorry that OpenDoc’s a casualty along the way,” Jobs answered. He applied the same thinking to the people. His engineers were getting calls offering three times as much money, and none were leaving. “Some mistakes will be made,” he said. “That’s good. Because at least some decisions are being made.” Then he pointed to the first LaserWriter printout. Apple didn’t need to explain PostScript or AppleTalk. It held up the page and asked one question: “Do you want this?” Technology is what’s inside the box. A sale is the page that comes out of it. Are you selling what’s inside your box, or what comes out of it?

In the late 1980s, American companies spent heavily advertising “quality” and chasing quality awards. Ask people on the street which products had the best quality, and they named Japanese ones, from companies that barely used the word in their ads. Steve Jobs, then running NeXT, had been learning from Joseph Juran, the engineer who taught quality to Japanese executives in 1954. In the video below, Jobs explains why all that American spending didn’t work. “Customers don’t form their opinions on quality from marketing,” he said. “They form their opinions on quality from their own experience with the products.” You can’t advertise your way out of a product that breaks. “One can spend enormous amounts of money on quality, one can win every quality award there is,” Jobs said, “and yet if your products don’t live up to it, customers will not keep that opinion for long.” So the work had to start with the product, not the marketing department. Treat everything as a repetitive process, measure it, take it apart and rebuild it. “No magic, no pep rallies.” He applied the same thinking to the people. In most companies, the answer to “why is it done this way” is “that’s the way we do it here.” At NeXT, the people doing the work could fix their own processes without asking. Jobs called it “the permission to not have to ask permission.” Then he pointed to Juran himself, still flying across the country in his 80s to teach a small startup, with nothing to gain. “His pocketbook is not what’s propelling him,” Jobs said. An ad tells customers what to think. The product decides what they actually think. When you pay extra for “quality,” are you paying for the product or for the ad?

In 1985, Steve Jobs left Apple and started a new computer company called NeXT. In 1997, Apple paid $427 million for it and brought him back. Six months after NeXT began, Jobs gathered his team for a retreat. In the video below, he explains why he opened by telling them the honeymoon was over. “The world doesn’t really care,” he said. “What the world cares about is what we produce.” They had been a startup for six months, and they had been spending money like one. In some areas they had a lot to show for it. In others, not much. “It would be a shame to have lost the war because we’ve won a few battles,” Jobs said. So he named the war out loud: “not run out of money until we get our product on the market.” The logo, the bank accounts, the coffee maker were all just part of the work of getting there. He applied the same thinking years later at Apple. “Focusing doesn’t mean saying yes, it means saying no,” he said. “We decide not to do a lot of things so we can focus on a few handfuls of things and do them well.” Then he pointed to the founders who come to him wanting to start a company to make lots of money. His answer: “Forget it.” The ones he’d seen succeed had an idea they needed to get out into the world, and often started a company only because nobody else would listen. Winning small battles feels like progress. Running out of money ends the war. Are you winning small battles with your money, or making sure you never lose the war?