Matthew Perry made $1 million an episode on Friends and spent about $9 million trying to get sober. In his last month, a doctor charged him $57,000 for 20 vials of ketamine that sold for about $15 each. In the video below, a year before he died, he describes the night doctors gave him a 2% chance to live. "Five people had an ECMO machine that night, and the other four died, and I survived." On September 30, 2023, the doctor met Perry for the first time. That day he texted a colleague: "I wonder how much this moron will pay." Then: "Let's find out." Same day, he bought $795 worth of ketamine and supplies from another doctor. Perry's assistant paid him $4,500. Over the next 12 days: 20 vials, $57,000. One shot was given in the back seat of Perry's car in a parking lot. That's about $2,850 a vial. Roughly 190 times the going price. Then the assistant found a cheaper source. He was paid $150,000 a year to manage Perry's medical care. In 11 days he bought 51 vials from a dealer prosecutors called the "Ketamine Queen." On October 27, the doctor texted that he'd been "stocking up." The next day, the assistant gave Perry at least three shots. Perry was found dead. He was 54. Then came the sentences. The dealer: 15 years. The assistant: 41 months. The doctor who called him a moron: 30 months and a $5,600 fine. The doctor who supplied him: 8 months of home detention. Netflix releases a documentary about Perry's life on Tuesday. Wednesday marks three years since he died. The doctor made $57,000 and was fined $5,600. Was 30 months enough?

Steve Jobs’s daughter grew up on $385 a month while he said she wasn’t his. On his deathbed he kept telling her: I owe you one. Lisa was born in 1978 on a farm commune in Oregon. Her mother was Chrisann Brennan, Steve’s girlfriend. Steve said the baby wasn’t his. A DNA test put the probability that he was the father at 94.1%. A court ordered him to pay $385 a month and pay back the welfare her mother had been living on. Days later Apple went public. He was suddenly worth more than $200 million. In 1983 he still told Time magazine that 28% of the male population of the United States could be the father. That same year Apple released a computer called the Lisa. When she asked him if it was named after her, he said: nope, sorry, kid. Years later he told Bono it was. At 14 she moved in with him. He had one condition: she could not see her mother for six months. She asked once if she could have his Porsche when he was done with it. You’re not getting anything, he told her. Nothing. And yet, she says, there was love. She remembers a freezing night when he sat through her boyfriend’s school play without a sweater, because he knew how much it meant to her. At the very end, dying of cancer, he kept apologizing for the time they had missed. I owe you one, he kept saying. I’m so sorry. Did she forgive him? Not at the time. Now, in many ways, yes. We did like each other, she said. I wish there had been more time. He built one of the most valuable companies in the world. The one thing he couldn’t buy back was the years he spent saying she wasn’t his. Can success ever make up for the people you failed on the way? Follow me for more stories like this.

Richard Hatch won $1,000,000 on the first season of Survivor. The IRS says he now owes $3.3 million on it. 51 million people watched him win in August 2000. He never paid the tax on the prize. His defense: he says he caught producers sneaking food to other players, and the show promised to cover his taxes if he won. CBS never commented. The appeals court said he never showed any proof of a deal. In 2006 a jury convicted him. He served 51 months in federal prison. In 2011 he went back for nine more, for not fixing his returns. Then the bill kept growing. This March, 26 years after the finale, a federal judge let the IRS collect about $3.3 million with interest. The government put liens on two of his homes in Newport. He is appealing on his own, without a lawyer. In the video below he explains why he thinks the tax was never his to pay. "The taxes on the million were required by law… to have been paid to Malaysia before we left the island… by CBS or Mark Burnett." The case for Hatch: if the show made that promise, he was set up. The case for the IRS: a $1 million check is income. Everyone else pays theirs. Was the first Survivor winner played by the show, or did he try to outwit the wrong player?

Shohei Ohtani signed for $700 million and takes just $2 million a year in cash until 2034. His interpreter took $16,975,010 out of his bank account. Some of it bought Shohei Ohtani baseball cards. Ippei Mizuhara had been at his side since Ohtani arrived in America in 2018. Around November 2021 he got into Ohtani's account, changed its security settings and phoned the bank pretending to be him, 2 dozen times. The money went to an illegal bookmaker. In 2 years he placed about 19,000 wagers and ran up more than $40 million in debt. Prosecutors said he took almost half of everything Ohtani earned with the Angels. Ohtani found out at a clubhouse meeting after his first game as a Dodger. Days later he read a statement through a new interpreter. "Ippei has been stealing money from my account and has told lies." Before sentencing, Mizuhara wrote to the judge that he had been underpaid. His salary had gone from $85,000 to $500,000. Ohtani paid his rent, flew him first class and gave him a Porsche. The judge gave the letter no weight. In February 2025 he got 57 months. Ohtani had to ask a court to give him back his own baseball cards.

Mark Zuckerberg is worth about $250 billion. On Kauai his lawyer called a Native Hawaiian woman to ask how it felt to get $800 for land she never knew she had. Her cousin had already sold her share for $400 to Northshore Kalo LLC, thinking the buyer was a taro farmer. It was Zuckerberg. In 2014 he paid a reported $100 million for 700 acres on the north shore and built a rock wall around them. Inside sat kuleana, small parcels Hawaiian families inherited for generations without wills or deeds. In December 2016 his companies filed quiet title lawsuits against more than 100 people to force those parcels to auction. Shannon Buckner owns land on the other side of his fence. If she walks onto it, she says, she gets arrested for trespassing. Teri Ferreira found out who the buyer was after the sale. "I was mad, I was upset, I felt deceived," she says. "He can offer me $100,000, I won't take it." After the backlash Zuckerberg apologized in the local paper and dropped the lawsuits in January 2017. "It's hard to save your land when you have a billionaire fighting you for it," another descendant says. Teri says that land is not for sale.

Bernie Madoff ran a $50 billion Ponzi scheme. he earned $710 in 12 years of prison work and died with a calculator, four packs of popcorn and a box of gefilte fish: On 29 June 2009 a federal judge sentenced Madoff to 150 years. Two weeks later he was moved out of a New York lockup and sent to the federal prison in Butner, North Carolina. In October, court papers gave the first look at his new life. A lower bunk in a cell shared with a drug offender. Night walks around the track with a mob boss and a convicted spy. Then he went to work. He was an orderly, first in the educational programs section and later around the chapel. Bureau of Prisons records, first reported by The City, show he earned $710 for almost 3,000 hours. About 24 cents an hour. One supervisor called him “not very dependable”. Another wrote that he “needs closer supervision than most.” In April 2021 he died at 82 of kidney failure. He had served about 12 of his 150 years. His property at death: eight AAA batteries, four religious paperbacks, a Casio calculator, four packages of popcorn, one ramen soup and a box of gefilte fish. $50 billion in fraud. $710 in wages.

Mila Kunis called Uber "the worst idea ever." Ashton Kutcher and his partner invested $500,000 in the company. By 2016, that stake was worth roughly $50 million, according to Forbes. In the video below, Kunis tells Stephen Colbert why she tried to talk her future husband out of investments like these. Her family left Soviet Ukraine in 1991, when she was seven. In Los Angeles, her father, a trained engineer, worked as a cab driver. Kutcher described Uber as a cab company where anyone could drive. He offered to order her a ride so she could try it. "You're going to put me in a car with a stranger? What is wrong with you?" Then he told her about Bitcoin. She asked, "Is it FDIC insured?". Kutcher replied: "No. That's the point. It's not." "I think this is a horrible idea," she recalled telling him. His response: "Cool, we're investing it." At the beginning of 2013, Bitcoin traded below $100. During the week of her interview in April 2021, it traded above $50,000. Kunis says she now books accommodation through Airbnb and takes Uber everywhere. "I've never been happier to be wrong."

In 1990, Donald Trump owed $3.4 billion and went on NBC acting like nothing was happening. He's 44. Sitting in Trump Tower. The Taj Mahal just opened for $1 billion, funded almost entirely by junk bonds at 14% interest. Revenue projections are already falling short. Contractors aren't getting paid. He owes money to over 70 banks. $800 million of it he'd personally guaranteed. He doesn't flinch. A year earlier he was on the cover of every magazine in New York. He owned a yacht, an airline, three casinos, the Plaza Hotel. Forbes pegged his net worth at $1.7 billion. By summer 1990, regulators warned of "the possibility of a complete financial collapse of the Trump Organization." The Taj Mahal filed for bankruptcy in 1991. Trump Castle and Trump Plaza followed in 1992. The Plaza Hotel filed the same year. His yacht was sold. The airline shut down. The banks put him on a personal budget. The New York Post ran the headline "UH-OWE!" His father sent a lawyer to one of his casinos to buy $3.5 million in chips. Not to gamble. To inject emergency cash. The Casino Control Commission fined them $30,000 for the illegal loan. The banks could have buried him. They didn't. They calculated that the name on the building was worth more than the debt behind it. So they restructured. He gave up equity, sold assets, and clawed back deal by deal. In 1995 he declared a $916 million loss on a single tax return. By 2004 he was hosting the most watched show on television. By 2016 he was President of the United States. The man on this tape is $3.4 billion underwater and talking like he owns the room. That's either delusion or the reason he survived.

Steve Ballmer sat in a golf club in 2023 and Charlie Munger, 99 years old and partner to Warren Buffett for 60 years, confronted him in front of a full room about why he had held his Microsoft stock for 34 years when every one of his executive partners had sold a 60 second exchange that captured the exact reason Ballmer is now worth more than Bill Gates The video is 60 seconds long and has already crossed 15 million views Munger looked at him in front of the whole room and said: "I know you're not that smart" Ballmer answered without pausing: "no, but I'm that loyal" Microsoft stock went flat for 13 straight years between 2000 and 2013. every analyst on Wall Street said sell. every executive partner Ballmer had at Microsoft did sell Ballmer did not sell a single share in 1980 Bill Gates called him at Stanford Business School and offered him 8 percent of a 24-person startup instead of the safe consulting path his father wanted. Ballmer took the equity in 2000 the dot-com bubble burst and Microsoft dropped over 60 percent in 18 months. every analyst said the party was over. Ballmer held every share in 2014 the Microsoft board pushed Ballmer out as CEO. he could have cashed the entire position on the way out. he held every share three decisions across 34 years. every one of them was Ballmer holding when the smart money was running that 8 percent he took in 1980 is now worth over $140 billion. Ballmer is personally worth more than Bill Gates today, because Gates gave most of his away and Ballmer never did intelligence tells you when to sell loyalty tells you when to hold the paycheck goes to the one who outsmarts the market the fortune goes to the one who outlasts it

In 2019, Tobey Maguire won $15.6 million playing poker against billionaire Andy Beal. Beal delayed payment and asked for a discount. Maguire spent $500,000 on a lawyer and collected his full $7.8 million share. In the video below, private poker organizer Molly Bloom describes what the Spider-Man actor was like at her table. She recalls him saying: “It’s not really about money. It’s more about crushing souls.” Bloom remembers Maguire assuring an opponent during one hand: "Listen, I have the top hand. I swear on my mother's life". The man agonized, eventually folded, and Maguire revealed the bluff. According to Bloom, he made a different demand of her: to receive a tip, she had to climb onto the table and bark like a seal. Bloom refused. She says the standoff lasted 35 minutes: the game stopped while everyone at the table watched. A few weeks later, Bloom says, Maguire arranged for one of the wealthy players to host the games at his house. The other players followed, leaving her without the game she had been running. Then Maguire called her: “You’re done. You’re over.” Lawyer Tom Goldstein helped Maguire collect the money from Beal. In January 2026, the actor described the arrangement in court, where Goldstein himself was facing tax charges. Beal had lost money to Maguire and owed him payment. Bloom refused to be humiliated and lost the game she organized. Was winning the money enough for Maguire, or did he need the people at the table to feel defeated?

Warren Buffett told Elon Musk he wouldn't want to take him on in candy. Musk said he was super super serious about starting a candy company. Buffett's had already made over $2 billion on a $25 million bet. It started on a Tesla earnings call. Musk said moats are lame. If your only defense against invading armies is a moat, you will not last long. What matters is the pace of innovation. A moat is Buffett's word for whatever protects a business from competitors. A brand, low costs, loyal customers. Days later the question was read to Buffett on stage in front of his shareholders. Is Elon right? Charlie Munger went first. Warren does not intend to build an actual moat. Buffett admitted that the pace has picked up and more moats are open to attack than before. You have to defend yours all the time. He said Elon may turn things upside down in some areas. Then he added one line. "I don't think he'd want to take us on in candy." Berkshire owns See's Candies. Buffett bought it in 1972 for $25 million. Musk fired back on Twitter. He was starting a candy company, and it was going to be amazing. Then he promised to build a moat and fill it with candy. The candy company never happened. See's has given Berkshire over $2 billion in pretax income, and it needed only about $40 million of investment along the way. What protects a business better, a moat or the pace of innovation? Follow me for more stories like this.

In 2012, Jeff Bezos's biological father learned who his son had become after 45 years without seeing him. He asked the biographer who found him: "Is he still alive?" Ted Jorgensen had lost contact with Jeff after his marriage ended. He agreed to let the boy's stepfather, Miguel Bezos, adopt him and to stay out of their lives. Decades later, biographer Brad Stone found him in his bicycle shop in Glendale, Arizona. The name Jeff Bezos meant nothing to him. Stone had to explain that the Amazon founder was his son. Then he showed Jorgensen photographs on his phone. According to Stone, it was the first time in 45 years he had seen his son, even in a picture. In a 2014 interview with Inside Edition, Jorgensen described giving up custody in two words: "Big mistake." A reunion, even if it happened, could never give him those years back. Jeff had grown up with another man as his father. While you wait for the right moment to call, someone you care about is living a life you may eventually hear about from other people. Think of the person you keep meaning to call. What are you waiting to change before you do? Watch Jorgensen discuss the decision in his Inside Edition interview.

Professional poker player Phil Ivey won $9.6 million at the Borgata. The casino paid him, then sued to get it back. At London’s Crockfords, he won another £7.7 million. They refused to pay. In the video below, Ivey says his job is to play the game, find a weakness in the casino and use it to win. He calls the casino his opponent and points out that it spends millions of dollars protecting its games. He wanted a specific brand of cards, a Cantonese-speaking dealer and the same decks reused. The casinos agreed. His playing partner, Cheung Yin Sun, asked the dealer to rotate certain cards, presenting it as a matter of luck. The cards had tiny differences along their backs. Once high-value cards faced one way and the others faced the opposite way, those differences helped identify what was coming next. Ivey never marked the cards. The dealer handled them. But the casino didn’t understand what those requests were doing to the odds. He called it an advantage. The casinos called it cheating. In 2017, the UK Supreme Court ruled against him: persuading the dealer to arrange the cards crossed the line. The casino had approved his requests while expecting to win. Ivey knew something about its own cards that it didn’t. Was he cheating, or should a casino know its own game before accepting someone’s money?

Stanley Druckenmiller, legendary macro investor and head of Duquesne Family Office, has a warning for young people chasing portfolio manager roles: "I've seen it ruin people's lives who weren't built for trigger pulling." Asked what advice he’d give someone entering the investment business, Druckenmiller started with motive: "First of all, if they're going in it for the money, they should go elsewhere." Druckenmiller's reasoning is competitive. "There's too many people in the business like me that just love the game. And they're not going to be able to outwork the people that are passionate in the game. And it's not a fun game if you're losing. It's horrible." On career progression, he separates two roles most people treat as one ladder: "I would say an analyst skill set in our business is completely different than a portfolio manager skill set. Once in a while, you'll get an overlap." His advice to analysts who love the research: think hard before assuming promotion is mandatory. "I would be careful if they really love the analyst part, which is where we all start, of thinking they have to become a portfolio manager." The upside of either path, in his words: "I got in the business because I wanted intellectual stimulation, and you're going to get plenty in either one."

Stan Druckenmiller once made over a billion dollars in a single day. Over 30 years he averaged a little over 30% a year and never had a single losing year. Ask him how, and he skips the big wins entirely. His secret is a pile of boring years, "I had a lot of 5 and 7s in there," and one rule about the number 50. Asked why not losing mattered so much, he didn't talk about genius. "It's just mathematics. If you go down 50, you've got to go back 100 to get it back to even." "If you make a bunch of 30s and then you lose 55 or 60%, you've got a long, long way back, and it's just the way the numbers work." His rule for the other side of it: "when you really see the ball, swing really big, and when you don't see the ball, don't swing." "It was a matter of never losing and then throwing some big numbers in there, maybe 10 times." Most people do the opposite. They chase one huge year, then give it back. A 50% gain followed by a 50% loss doesn't leave you flat. It leaves you down 25%. The fix is his: keep the average years small and safe, and only size up when the setup is obvious. And he admits part of it is temperament. "I'm a sore loser, I don't like to lose." Even he breaks his own rule. "Full disclosure, I missed the dollar, probably the biggest miss of my career in currency trades." He saw it and didn't swing: "I just couldn't bring myself to own Joe Biden and Jerome Powell." Save this and watch the two minutes before your next big swing.

Jeff Bezos put $250,000 into Google months after its funding round had closed. By the IPO six years later, that check was worth about $280 million. In August 1998 Amazon bought a comparison-shopping startup called Junglee. Its president, Ram Shriram, moved to Amazon with the deal. He had also been one of the first people to back a search engine that two Stanford PhD students, Larry Page and Sergey Brin, were building. So he brought his new boss to meet them over breakfast at his house. The founders showed him how their search worked. The round had closed months earlier. As his biographer Brad Stone tells it, Bezos still said, "I want in." He asked only for the same terms everyone else had gotten. Shriram took the request to Page and Brin and argued that the Amazon founder's advice and rising fame could help the company. They let him in. In August 2004 Google went public at $85, and his stake equaled 3.3 million shares. Later The New Yorker asked him why he had done it. "I just fell in love with Larry and Sergey."

In 2011, Warren Buffett called Bank of America to offer $5 billion. The call center wouldn't put him through to the CEO. Berkshire eventually found a way to reach Brian Moynihan. When Buffett offered to invest, Moynihan told him the bank didn't need the capital. "I know you don't. That's why I'm calling you." Moynihan later recalled Buffett explaining that the bank needed stability, which his backing could provide. Bank of America was facing mortgage litigation and a collapse in investor confidence. On August 25, they announced the deal. Berkshire would invest $5 billion in preferred shares paying 6% a year, or $300 million annually. It also received the right to buy 700 million common shares at about $7.14 each. That gave Berkshire years to decide whether to become a common shareholder at a price fixed during the turmoil. In 2017, Berkshire exercised those rights, using its $5 billion of preferred shares to pay for the common shares. It had collected preferred dividends while waiting for the bank to recover. An ordinary investor could have profited from the same recovery. But buying common stock meant accepting different risks and receiving none of Buffett's contractual terms. Before copying a famous investor's purchase, check what they actually bought. Moynihan tells the story of the phone call in the video below. Following Buffett into the same company doesn't mean making the same investment. Munger studied how trust in an authority can lead us to skip our own judgment. The answer is in this video.

At the 1995 Berkshire Hathaway Annual Meeting, a shareholder asked Buffett to identify the wonderful investment opportunities that were too small for Berkshire but suitable for individual investors. Buffett’s answer was disappointing but instructive: “We don’t look anymore.” Before studying an investment, Buffett first considered its size. If the opportunity was too small to become meaningful to Berkshire and was unlikely to become large enough anytime soon he stopped there. Berkshire’s enormous capital base had eliminated thousands of potential investments from consideration. An individual investor managing a smaller portfolio faced the opposite situation. “You run into companies that are less followed as you get smaller. And there’s more chance for inefficiency when you’re dealing with something where you can buy $100,000 worth of it in a month rather than $100 million.” Buffett was not carrying around a secret list of 25 small companies. He simply believed such opportunities continued to exist because they had always existed. When Buffett began investing, he went through every page of the Moody’s and Standard & Poor’s manuals approximately 20,000 pages in total. A number of attractive investments appeared in no brokerage reports. They were simply overlooked. “You could find out about them, but nobody was going to tell you about them.” Munger then remembered an extreme example from Buffett’s early years: the Delta Duck Club. The club had been formed by 100 people contributing $50 each, although two never paid, leaving 98 shares outstanding. The club purchased land in Louisiana and later discovered oil and gas beneath it. The company was renamed Atled Delta spelled backward which Buffett joked demonstrated the group’s sophistication. Years later, with oil selling for approximately $3 per barrel, the property was collecting about $1 million annually in royalties. Each share had approximately $20,000 in cash and generated roughly $11,000 in pretax income. The stock traded for only $29,000 per share. Buffett used it as an example of market efficiency: “$29,000 for $20,000 of cash plus $11,000 of royalty income at 25-cent gas and $3 oil. I don’t think so.” Buffett’s small-investor advantage was not privileged information. It was scale, effort and a willingness to search where almost nobody else was looking. “You can find things out there.”

James Simons, the mathematician who built a multi billion hedge fund that averaged 66 percent annual returns for thirty straight years: "There's one specific way of thinking about randomness that made my fund more money than any hedge fund in history, and it started as a piece of pure math I never once thought would matter to anyone." this is the exact pattern explaining why some of the most valuable discoveries look completely useless the moment they're actually made. cut through the physics and the timeline is the whole story. the math came first, built purely because it was elegant, with zero application in mind. it sat untouched, cited by almost nobody, for close to twenty years. then an entirely separate field, studying a completely different set of physical questions, needed exactly that structure to describe something they'd just started observing, and the old, dormant result turned out to be the missing piece the whole time. nobody could have connected the two fields at the moment the math was first written down. the connection only became visible once the second field had developed far enough to even ask the right question. most people evaluating a piece of research ask whether it has an obvious application right now, never suspecting that the most valuable results are often the ones that look completely useless for years before the right problem finally catches up to them. zoom out to how this plays out sitting on a dormant statistical result that doesn't obviously connect to markets yet on a desk today. a piece of pure mathematics or an old, forgotten result from an unrelated field can sit completely dormant for years, looking like nothing more than an academic curiosity, until the right market structure or the right dataset finally emerges to make it suddenly, urgently relevant. this is exactly what "this doesn't have any practical use" dismissals skip. having no visible application today and having no value at all are different claims, and the entire history of this specific result is proof of exactly how large that gap can be. the math was never useless. it just hadn't met the problem it was actually going to solve yet. Bookmark this alpha and watch full lecture. The answer is in this video

"You can cry all right, but you can't quit." In his final interview, 99-year-old Charlie Munger spoke about losses that cannot be undone. His nine-year-old son, Teddy, had died of leukemia. "I cried all the time when my first child died." Munger said you cannot bring back the dead or fix every tragedy. If you have to walk through the streets crying for hours, you can keep going that way. He called it "soldiering through." His words offer reassurance when you're struggling: crying doesn't mean you've given up. Decades later, he described the pleasure it had given him to watch doctors learn to save children with leukemia. He couldn't bring Teddy back, but he could feel joy for families who now had a chance. His words are in the two-minute clip below.