Martin Shkreli paid $2 million for the only copy of a Wu-Tang Clan album. On camera, he joked the Feds might end up owning it. They did. Late 2015. His Midtown apartment. A VICE reporter, a bottle of wine, a chess game. A few months earlier he raised the price of an HIV drug from $13.50 a pill to $750. Is he evil? "I think I'm the opposite of evil." His view of the business is simple. Companies have owners. "Their owners demand that they extract as much profit as possible." "That's the way the world works." Then the album. Two CDs in an embossed case in his living room. Will anyone ever hear it? "I could see myself in a place where I break it." Snap it in half. Bury the pieces. "I just bought it a few months ago, and I was arrested a month ago." 2017. A jury convicts him of securities fraud. 7 years. The government seizes the album to pay what he owes. He bought it so nobody else could have it. "Who knows, maybe the Feds will own it soon."

Vince Young's mother told him he'd end up dead, crippled or in jail. He ended up with a $58 million NFL contract. Then bankruptcy. Houston. Middle school. A big fight after spring break. The police pick him out of the crowd and put him in handcuffs. His mom comes to get him. In the car, she's screaming. "You're going to end up dead, crippled or in jail." He looked around and saw she was right. Friends shot. Friends in and out of prison. "I didn't want to fall into that bunch. Be that stat." At home there was fighting. So he climbed out his bedroom window and sat in a tree. What did he think about up there? "Why is our family fighting all the time?" He knew the answer. "It was because we was broke." 2006. The Titans draft him third. $58 million, about $26 million guaranteed. 2012. He's out of the league. His lawyer: "Vince needs a job." 2014. Bankruptcy. The boy in the tree knew what broke does to a family. The man with $26 million guaranteed ended up there anyway. "It always goes back to not having income."

Michael Vick signed the biggest contract in NFL history. $130 million. From a federal prison cell, he handed $8 million to a financial adviser who turned out to be a med school graduate. 2007. Dogfighting. 23 months in federal prison. He says the hardest part wasn't the cell. "The toughest part was being in there and filing bankruptcy." He couldn't believe it. "I just gave eight million dollars to this guy over here. I'm not filing bankruptcy." He filed anyway. $16 million in assets. Over $20 million in debts. The Falcons wanted their signing bonus back. "I respect them for that." He had admitted in court he never balanced a checkbook or reconciled a bank statement. Inside, he made a promise. "I'm gonna make full restitution to everybody." He played again. And by 2017 he had paid back $17.4 million of the $17.6 million he owed. His reason was simple. If he paid everyone back, maybe the $8 million would come back too. "A lot of money came up missing." He paid back every creditor. Nobody paid him back. "Where's the rest of it?"

$80 million in the NFL. Two years after his last game, Terrell Owens told Dr. Phil he couldn't afford his child support. May 2012. Three of the four mothers of his kids are in the studio. One of them says they never needed a judge. "I never took Terrell to court ever." He says he kept raising her payments himself. "6,000 to 8 to 10 to 12 on my own." Then she found out another mother was getting $20,000. She hired a lawyer. "So I had to start paying her 20." Dr. Phil cuts to it. Can you afford all this? "Not at this moment in time, no I can't." She says he spent the money on fighting her in court instead. His answer to all three: "The only time any of you really have picked up the phone is because of money." The cars? The houses? "Well I did, and those were investment properties." "You're not going to see me popping bottles in the club." At his peak he paid about $45,000 a month. $80 million earned. Not enough for four kids. "It wasn't a plan."

Burt Reynolds was once the biggest box office star in Hollywood. At 79, his proof that he wasn't broke was a red tie. 2015. His Florida home. A TV crew asks him to set the record straight. "I'm not bankrupt. If I was bankrupt, I wouldn't have my red tie on." At his peak he made $10 million a year. Then came the restaurants. Po' Folks. Daisy's Diner. Both failed. $20 million gone, and he had signed for it personally. 1996. Chapter 11. His second wife, Loni Anderson? He says she maxed out a $45,000 credit card in half an hour. "She liked to spend money. Mine." "I really couldn't afford her." He turned down Han Solo, James Bond and Pretty Woman. Which one does he regret most? "All of those. I wish I had done them all." His advice: "Watch out who your friends are." In the '80s he was worth an estimated $200 million. When he died in 2018, about $500,000. Would he marry again? "No, ma'am." "Check, please."

Boris Becker won Wimbledon at 17 and made about $50 million on court. On the day he was sentenced, he wore a tie in Wimbledon's purple and green. April 29, 2022. London. "To make a matter even more dramatic, it was the birthday of my wife." Flowers in the morning. Then court. "There was a 50/50 chance I got a suspended sentence." His lawyers told him: "Get ready. You might have to go inside." He had been declared bankrupt in 2017. After that, he moved hundreds of thousands of pounds to other accounts, including his ex-wife's. The rent on his Wimbledon house was £22,000 a month. The sentence: 30 months. That night he became prisoner A2923EV. "Those numbers I'll never forget." Wandsworth didn't care who he was. "I was one of many." How did it start? Wimbledon at 17. Again at 18. "Everybody wanted a piece of me." At 17 he won Wimbledon unseeded. At 54 he was a number. "I'm a human being. I make mistakes."

Gary Coleman made about $18 million as a child star. When his trust was opened at 18, his parents' share was $770,000. His was $220,000. 1978. Diff'rent Strokes. He's 10, with failing kidneys. His parents set up the trust. Then they put themselves on the payroll of his production company. 1989. He's 21. His mother asks a court to take control of his $6 million fortune. She says he can't handle his affairs. His answer: "Obviously stems from her frustration at not being able to control my life." That same year he sues his parents and his business manager. $3.8 million. They deny all of it. 1993. A judge awards him $1.28 million. Taxes, lawyers and dialysis take most of it. That year, on TV: "If someone had told me... I would've got out." 1999. He files for bankruptcy. He takes a job as a security guard. He never speaks to his parents again. May 2010. He dies at 42. His mother tells People: "We loved Gary very much." They managed his money for 18 years. They hadn't heard his voice in over 10. "I'm sick of all of you people."

Jack Whittaker won $315M on Christmas 2002. He gave his 17-year-old granddaughter $2,000 a week and 4 cars. He was already a millionaire. His construction business was worth $17M. In the video below, he is asked whether 4 cars made sense for a teenager. "To a young kid cars mean a lot, and I'm very proud that she had four cars." Her name was Brandi. He calls her the shining star of his life. "She was very responsible with her money." Her boyfriend, Jesse Tribble, starts showing up in new clothes. His father notices. "I know firsthand she bought things for Jesse." Soon they are both on drugs. "Papa, all I care about is drugs." Jack checks her into 3 treatment programs. None of them work. September 2003. Jesse is found dead of an overdose in an empty house Jack owns. His father: "I blame her for my son's death." December 2004. Brandi disappears. On December 20, she is found dead behind a junked van. The cause of death is listed as unknown. "I really had my arms around her and protected her before I won the lottery." He could buy her 4 cars. He couldn't get her through 3 treatment programs. His wife said she wished she had torn the ticket up. "I wish that we had torn the ticket up too." Then he says this about himself. "I don't like Jack Whittaker."

Archie Karas turned $50 into $40M in Las Vegas. It took him almost 3 years. Losing it took 3 weeks. December 1992. He has just lost his whole bankroll at poker. He gets in his car with $50 in his wallet and drives to Vegas. First, pool. One man keeps raising the stakes. $40,000 a game. Karas walks away with $1.2M. Then poker. He beats Chip Reese. Only Johnny Chan beats him in a first round, for $900,000. Then dice, because dice are faster. "I ended up winning every $5,000 chip at Binion's Horseshoe." By 1995 he is up more than $40M. "Money means nothing to me." Then the 3 weeks. Craps: $11M. Back to Chip Reese: $2M. Baccarat: $17M. Total: $30M. He goes home to Greece, comes back, and bets $300,000 a roll until it is gone. Years later, he is asked how much he won in total. "I lost the money back anyway." "I consider myself the king of gamblers." Asked what he was most proud of in his life: "Not much, to tell you the truth." He died in 2024, at 73. $50 to $40M took almost 3 years. $40M back to nothing took 3 weeks.

Evander Holyfield made $230 million in the ring. His own sister took out a second mortgage on his house without telling him. The house had 109 rooms. Outside Atlanta. The bank behind the loan goes under. The mansion goes to auction. Chase Manhattan buys it for $7 million. What happened? "One of the family members borrowed money off my house." The interviewer stops him. A second mortgage on a house she didn't even own? How much? "Too much." He's the youngest in the family. His older sisters were almost like a mother to him. "After my mama passed, now everybody want to steal from me." He didn't want to call them out. Would he press charges? "I wasn't going to put them in jail." Rick Ross ends up with the house for $5.8 million. He fought Mike Tyson for money. He wouldn't fight his sister for his house. "I made too much money to stoop that low."

Jack Whittaker won $315 million in the Powerball on Christmas 2002. Two years later, his granddaughter was found dead behind a junked van at a place called Scary Creek. Brandi was 17. The center of his life. He gave her about $2,000 a week. And four cars. "I'm very proud that she had four cars." New friends came with the money. Then drugs. "She said, Papa, all I care about is drugs." Three treatment programs. None of them worked. September 2003. Her boyfriend overdoses in an empty house Jack owns. December 2004. Brandi stops calling. "Brandi never went a day without calling me." His wife goes on local TV. "We need you here with us at Christmas time." December 20. They find her. "I really had my arms around her and protected her before I won the lottery." "Once I won the lottery, there wasn't enough of me to get my arms around everything." His wife says she wishes she'd torn the ticket up. "I wish that we had torn the ticket up too." He won on Christmas. He lost her five days before one. "I just don't like what I become."

Antoine Walker earned $110 million in the NBA. His first big check bought his mother a house. Years later, a million dollars of his checks bounced at three Las Vegas casinos. June 1996. The Celtics draft him sixth. He's 19. His mother raised six kids on welfare. He talks the team into paying him a lump sum up front. It goes on a home for her. Then the circle grows. Eight, nine guys from the neighborhood. "I actually wanted them to see the same lifestyle that I was enjoying." Five or six cars at once. Bentleys. Maybachs. Rolexes. Cancun. Puerto Rico. Vegas. "I would travel eight to 10 people with me and pay for their flights, hotel rooms." He had a financial advisor. "As any young arrogant kid, I didn't want to listen to him." 2008. He retires. The recession hits his real estate. "I lost the bulk of my money investing in real estate." And the rest? "I lost a significant portion of money gambling." 2010. He files for bankruptcy. $12.7 million in debts. $4.3 million left. One check bought his mother's house. Seven or eight banks came for the rest. Does he regret the career? "I would never take it back."

Nicolas Cage outbid Leonardo DiCaprio for a dinosaur skull. $276,000. Then he had to hand it back to Mongolia, and he never got his money back. At one point he was worth $150 million. Two castles. Homes in New Orleans, Malibu and the Caribbean. Then came the creditors and the IRS. April 2023. 60 Minutes finds him in Las Vegas. Was it the spending? "It wasn't because I spent $80 on an octopus." The real estate market crashed. He couldn't get out in time. "I paid them all back, but it was about $6 million. I never filed for bankruptcy." So he takes the roles. All of them. "Work was always my guardian angel." "It may not have been blue chip, but it was still work." The critics call it a paycheck. "Even if the movie ultimately is crummy, they know I'm not phoning it in." 2021. He plays a heartbroken chef in Pig. "I wasn't acting." "I think it's probably my best movie." He puts it up against Leaving Las Vegas. The one that won him the Oscar. The skull never came back. Nicolas Cage did.

George Lucas could have asked 20th Century Fox for a million dollars to make Star Wars. He asked for T-shirts instead. The studio does what it always does. Hands him a boilerplate contract. Here, sign this. His deal memo says a salary and 40% of the net profits. "If you have net you never see anything out of it." So he goes back and does what nobody had done before. He reads the entire agreement. "I want to change everything to be in my favor." He asks for the sequel rights. And the licensing. Fox shrugs. If the film flops, who cares about sequels? Licensing isn't worth anything. Nobody can license anything. Why does he want it? "I was only doing it really to get t-shirts and posters." He's afraid the studio won't promote the movie. He doesn't ask for the million. "So they thought they were getting a good deal." May 1977. Star Wars opens. 2012. Lucas sells Lucasfilm to Disney for $4 billion. Fox kept the million. Lucas kept the sequels. It started with T-shirts.

Bobbi Brown built a makeup empire with her own name on every lipstick. Her next company is named after a road she saw on Waze. 1995. Estée Lauder buys Bobbi Brown Cosmetics. A reported $74.5 million. The deal comes with a 25-year non-compete. She counts it on her fingers. "I'm not going to want to work when I'm in my 60s." 22 years later she leaves Estée Lauder. Four and a half years still left on the non-compete. Her name stays behind. She needs a new one. Driving through the Hamptons, she looks down at the map. Jones Road. "I couldn't use Brown because of the noncompete I'd signed." October 2020. The day the non-compete ends, Jones Road launches. Profitable from year one. Too old to start over? "I'm so much better at 67 than I ever was at 37." "There's nothing you can't do at any age." Her advice to everyone else? "Stop complaining. Stop making excuses." Estée Lauder kept Brown. She took Jones. "If something doesn't work out, it's okay. Do something different." She did. She found the name on a map.

TLC's CrazySexyCool went diamond. Each of the 3 women behind it was taking home less than $50K a year. In the video below, February 28, 1996, they walk into the Grammy press room with 2 new Grammys and tell reporters the truth. "We're as broke as broke can be." July 3, 1995. The best-selling American girl group of all time files for bankruptcy. $3.5M in debt. How? The deal: About 7% per album. Minus studio costs. Minus videos, promotion, tour support, advances. What was left: about 20 cents per album. Split 3 ways. "You can sell 10 million albums and still be broke." By the LA Times count, they got about 1% of $175M in sales. T-Boz says they never understood what the contract would cost them. Then there was the name. 2013. The Breakfast Club. T-Boz explains what it cost to own the name TLC. "A million dollars per letter, honey." $3M total. Who sold it to them? "Y'all know who I'm talking about." Their old manager Pebbles called their story "mess and lies." She later sued Viacom for $40M over the TLC biopic. The label sold their albums by the million. They bought their name back by the letter. In 1995 each of them made less than $50K a year. Each letter of TLC cost $1M.

In 1989 Wally Amos started a new cookie company. Famous Amos sued him for using his own name. March 1975. Los Angeles. The first Famous Amos store opens. By 1981 it is a $12M company. By 1985 it is losing money, and he brings in outside investors. "I found I had lost all ownership in the company I founded." 1988. The Shansby Group buys it for $3M. He stays on as a paid spokesman. In 1989 he walks out. Then the lawsuit. "They were saying I didn't even have the right to my own name." He calls the new company Uncle Noname. "You don't need a name to have a product and no name is a name." 1991. Famous Amos sells to a Taiwanese company for $63M. He owns none of it. 1996. Uncle Noname files for bankruptcy. 2016. Shark Tank. He is 80, asking $50K for 20% of The Cookie Kahuna. Under the deals he signed, he can't even use his own face to sell it. No Shark invests. Did he blame them? "Blaming everyone else for your position in life, it is like being in quicksand." Past 80, on a morning TV show, he launches one more brand. Aunt Della's. Named for the aunt whose cookies started it all. Famous Amos still puts his face on the bag. He couldn't put it on his own. In 2007 he told the AP: "Being famous is highly overrated anyway."

Wally Amos built Famous Amos into a 12 million dollar cookie company by 1981. Then he lost it, and the right to use his own name went with it. In the clip below, he is past 80, on a morning TV show, launching yet another cookie brand. Look at the name on the screen. Aunt Della's. Not Amos. He opened his first store on Sunset Boulevard in 1975. The AP described him as a great promoter who struggled as a businessman. New investors kept taking more of his share. In a book he titled Man With No Name, he wrote: "I found I had lost all ownership in the company I founded." In 1991 Famous Amos was sold to a Taiwanese company for 63 million dollars. By then he owned none of it. One of the brands he started afterwards was called Uncle Noname. In 2016, at 80, he walked into Shark Tank with a cookie company called The Cookie Kahuna. He asked for 50,000 dollars for 20 percent. Because of agreements he had signed with Famous Amos, he could not even use his face to sell it. No Shark invested. In 2017 he posted a video saying he was flat broke and struggling to pay for rent, food and gas. He never blamed only the buyers. In 1999 he told The Times he lost the company because he didn't listen to people, since he was Famous Amos. 12 million dollars. 50,000 dollars. The bag kept his name. He had to keep inventing new ones. He died in August 2024, at 88. Famous Amos still sells cookies with his name on them. Did investors take Wally Amos's name, or did he sign it away one deal at a time?

The CEO of a bank that moves $5 trillion a day sat down at Stanford and gave away the two rules her most famous shareholder handed her for dealing with people. for free. business schools spend two years teaching people to map out their next job title. a former Citi CEO took her version of that plan and tore it up. it changed the next 10 years of her life. her name is Jane Fraser. CEO of Citi since 2021. the first woman to run one of America's Big Four banks. at the tail end of the mortgage crisis she left the private bank in London to run a mortgage call center 45 miles outside St. Louis. 22,000 people, and they all knew half of them would probably get fired. she opened by telling them her 11-year-old had just run the baseball bases the wrong way because he only knew cricket. the shareholder was Warren Buffett. rule one: you can always call them an asshole tomorrow. rule two: criticize by category, praise by name. a payments fintech pitched Citi on its IPO and bragged it had hit a trillion dollars, then asked how much Citi moves. she told them 2,000 trillion a year. "good people in a bad culture, they'll go back to being good people again and fix the culture. but an asshole is always an asshole." she got the top job at Citi by collecting skills instead of titles. whoever writes your performance review will never tell you to do the same.