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Charlie Munger died with about $2.2 billion. his partner Warren Buffett is worth well over $100 billion. they ran Berkshire side by side for decades. In the clip below Munger, 95 at the time, gets asked why the gap is so big. his answer takes ten seconds. “Well, he got an earlier start.” Munger was actually six years older. but Buffett bought his first stock at 11, and Munger only set up his own investment partnership at 38. He adds two more reasons, almost as an afterthought: Buffett is probably a little smarter, and he works harder. “There are not a lot of reasons.” Then he turns the question back on the room. “Why was Albert Einstein poorer than i was?” This was the Daily Journal meeting in 2019. Munger died four years later, a few weeks short of 100. So is the head start the whole story - or is Munger just being modest about the other two reasons?

In 2003 an accountant named Chris Moneymaker joined an $86 poker tournament by accident, then tried to lose it on purpose. He failed at both and won $2.5 million. In the video below he tells it himself: "I couldn't sell the seat and 4th place was $8,000 in cash. I tried to get 4th place. That was my goal. I wanted to get 4th place. We got down pretty deep and I started trying to dump some chips to get 4th place." He had meant to join a cash game. He says he had about $200 in his account at the time, and only worked out afterwards that he had registered for a satellite into a satellite into the World Series of Poker. He says he never would have played if he had known. That $86 game fed into a $630 one with 69 players and three seats to the Main Event. Three seats meant fourth place was the first losing position, and it paid $8,000 in cash. He wanted the cash. The seat couldn't be sold or transferred in 2003 you played it or you burned it. So he started throwing chips away. While he was doing it, a friend noticed, called him, and bought half his action. He couldn't lose. He got a seat. He had never played a live tournament in his life. In Vegas he knocked out Phil Ivey without knowing who Ivey was, he only knew three players in the world. Then he beat Sam Farha heads-up, going all in on the river with King high and nothing else. $86 became $2,500,000. That is 29,070 times his money. He was aiming for $8,000. He missed by $2,492,000. He calls the whole run a lottery ticket. But nobody bluffs Sam Farha off a pair with King high by accident. So which is it, was he lucky, or is he a genius?

Michael Jackson left one of the biggest fortunes in music. His father, the man who built the Jackson 5, got $0. Michael’s 2002 will left everything to his mother, his three children and charity. His father wasn’t even mentioned. Joe Jackson was the man who had pushed his sons from Gary, Indiana to Motown. He managed the Jackson 5. He was there before anyone knew Michael’s name. Five months after Michael died, Joe went to court. His lawyers asked the estate for a monthly allowance. His expenses, they said, exceeded $15,000 a month. His only other income was $1,700 a month in Social Security. At the same time, the court had approved more than $26,000 a month for Katherine and $60,000 a month for the children. In 2010, Joe withdrew the request. A year later, he sat down on camera and said what he really thought. “All that money that they’ve taken from the Jackson family, I wish it would go retroactive. Make them give it all back.” And then, with a laugh: “Everybody got paid but us.” Was Joe Jackson a father who was robbed, or a father who got exactly what Michael wanted him to get? Follow me for more stories of famous names who lost everything to the people closest to them.

In 2009, a CBS producer demanded $2 million from David Letterman to keep quiet about his affairs with employees. Letterman went to prosecutors, then told his audience what he had been hiding. In the video below, Letterman admits on his own show: "I have had sex with women who work for me on this show." It began with a package he found in his car around six in the morning. It contained evidence of his affairs and a threat to turn them into a film unless he paid. The demand came from Robert "Joe" Halderman, a producer for 48 Hours at the same network, CBS. Letterman's lawyer met him three times, and prosecutors arranged a sting involving a fake $2 million check. Halderman deposited the check. On October 1, Letterman testified before a grand jury, Halderman was arrested, and that evening the host told the story on air. Halderman's defense initially described it as a screenplay sale. In 2010, he pleaded guilty to attempted grand larceny and received six months in jail. Letterman had married Regina Lasko just six months before the scandal; his spokesman said the affairs predated the wedding. On October 5, he apologized to his wife and staff, saying his behavior had deeply hurt Regina. Was this an honest confession from Letterman, or a way to make the main scandal the blackmail rather than his affairs with employees?

Arnold Schwarzenegger says he saved every dollar until he had about $26,000, then put all of it into a $235,000 apartment building. Two or three years later he sold it for roughly double, and by 30 he was a millionaire, before his Hollywood career took off. In the video below, he explains how a bodybuilder with almost no income pulled that off. He started working at 13 because his parents couldn’t afford his gym clothes or a bike. At a glass factory he swept up broken glass and talked them into paying him like an adult. In America, he saved every dollar from seminars, posing exhibitions and a small mail-order business. Before buying a home to live in, he wanted property that paid him. His first purchase was a 6-unit building with an owner’s apartment twice the size of the others, and he moved into it. When he sold, his $26,000 had turned into a profit of $150,000 to almost $200,000 in about 3 years. He says there was not a single dollar left after the deal. He kept doing it anyway, until he owned more than 100 apartments plus offices in Santa Monica. Would you put every dollar you have into one building, or is that a risk only someone with no backup plan would take?

Cornelius Vanderbilt died in 1877 with $100 million, more money than the U.S. Treasury. In 1973, 120 of his descendants gathered at Vanderbilt University. Not one of them was a millionaire. His great-great-great-grandson is Anderson Cooper. At 14 he was walking up the stairs at home and heard his mother, Gloria Vanderbilt, on the phone: "Well, I'll always be able to make money." "I remember stopping and freezing… and thinking: we are doomed." At 13 he'd been telling her to open a savings account. By 14 he was working as a child model. By 1885 the Commodore's son had more than doubled the fortune, to about $230 million. Then the next generation's wives decided to take over New York society. "And then the spending begins." Worked out. $230 million in 1885. Left alone at a plain 5% a year until 1973: about $17 billion. Split 120 ways: about $140 million each. What the 120 actually had: not one had $1 million. Spending only the 5% would have paid the family $11.5 million a year, in 1885 dollars, forever. Keep this part. A fortune doesn't need a thief. It only needs each generation to spend a little more than it earns, and more heirs to split what's left. Gloria inherited what remained, then made her own money with jeans. Anderson's parents made sure he knew: "There wasn't some pot of gold waiting for me, and I'm glad." The clip is three minutes. Watch him on the stairs, then decide. You have $100 million and one child. How much do you leave them?

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."