Charlie Munger said this on camera, weeks before he died: "I don't regard Elon Musk as truly rich, because I don't think it's sure that everything he's working on can work." Then he went further. "I would not invest in Elon Musk myself." Munger's reasoning wasn't about Tesla's product or Musk's talent. It was about pattern. "He's used leverage so much that he's doubled down right to the edge of extinction maybe two or three times." Asked how many times Musk had walked that edge without falling in, Munger's answer: "he's done it three times. Maybe he's got six more." This is coming from a man who spent six decades building Berkshire on the opposite principle. Munger and Buffett deliberately took smaller stakes than they could have afforded, using less leverage than was available, specifically so a bad stretch would never wipe out the people who trusted them. Munger used the phrase "two hard pile" for things he'd rather not spend time thinking about, things he can't fix himself. He used it earlier in the same conversation for the risk of nuclear war. Elon Musk went in the same pile. "I never met with him," he said. "As far as I'm concerned, he doesn't exist."

Gary Stevenson lost $5 million in three days at 23. His mates were around him playing video games, and he couldn't tell them. In the video below, the former Citibank interest rate trader describes that week. By the end of it, he said, he had lost $8 million. Before that, he had made $12 million for the bank and been paid just under £400,000. A lot of his friends couldn't get jobs. He had graduated into the financial crisis, and they were playing Pro Evolution, a football game, while he sat there thinking, "I've lost $5 million, how much more can I lose?" He feared he would lose his job. And he couldn't say a word about it. "It really dehumanizes you," he said. "You can't turn around and tell them I lost $5 million this week. They're not going to understand." The stress, he said, separated him from his friends and his family. He couldn't think about anything else. Then a Citi economist walked him through government debt in Italy, Spain, Portugal, Greece and Ireland. Stevenson came out of that meeting asking how it could be possible. "We can't all go into debt, somebody has to be on the other side of that." He later wrote a memoir about his years in finance, The Trading Game. Would you have told your friends, or kept it to yourself?

Jeffrey Dahmer was asked in prison, "Do you still feel those same urges?" He answered, "I wish I could say that it just left completely, but no." In the video below, he goes on to say there are times when he still has "the old compulsions." Just before this, the narrator noted that Dahmer may sound like he understands his own mind. The narrator's view is that he does not, and that he cannot stop whatever drove him to kill. He had confessed to murdering 17 young men. As time went on, the narration says, his mind became more and more warped, and he was clever enough to keep eluding police for 13 years. Dahmer dates it to his teens. "I started having these obsessive thoughts when I was about 15 and 16 and they got worse and worse." He described the fantasies as being about "control, power, complete dominance." The narrator says to listen to him talk "about the most unnatural things in the most matter-of-fact of ways." That, the narrator says, is when "you realize that none of it has touched him." Earlier in the interview he said he always knew it was wrong. Asked whether someone like him could have been stopped or helped, he said no, that he was "dead set on going with this compulsion." Asked whether he would still be committing the crimes if he were free, his answer was "probably." Is a confession like this honesty, or a warning?

Ashley St. Clair told Don Lemon she turned down $40 million to stay silent about her child with Elon Musk. Musk denies the offer ever existed, and she points to a call in a new documentary. In the video below, Lemon presses her on the evidence. Her answer is a call with Jared Birchall, which she said is all in the film. Lemon put it to her this way: "you've got the receipts of the offer that he's saying doesn't exist." St. Clair replied that Musk "will lie so loudly to the entire world despite a massive amount of evidence to the contrary." The Wall Street Journal reported the terms as $100,000 a month plus a $15 million lump sum. St. Clair has described the payments as running 20 years. That adds up to about $39 million. Musk wrote on X that she "was never offered that and has a history of making false claims." He has also called the documentary a "hit piece." She also said the film shows how much Musk tries to control the narrative, which she reads as a sign that he cares what the public thinks of him. Her takeaway at the end is short. "The biggest takeaway is to not be silent," she said, and she ends with "don't take the money." Would you have signed it, or walked away like she says she did?

Ron Wayne sold his 10% of Apple for $800 twelve days after it was formed. Fortune estimates the stake could now be worth between $75 billion and $360 billion. In the video below, Wayne and Steve Wozniak tell Bloomberg West how it started. Wozniak said Steve Jobs introduced Wayne "as a person that we could trust as an intermediary" if the two ever disagreed. Wozniak called Wayne the one with "a mature adult mentality," and said he typed up their partnership agreement so it looked "like it came from a lawyer." Wayne said he settled a dispute between them. Jobs then proposed 45% each for himself and Wozniak, and 10% for Wayne "as a philosophical tiebreaker." Wayne gave his own reason for leaving. He said he could see himself "shuffling papers for the rest of my life" in a back office. He also felt "intimidated" standing in the shadow of "real geniuses." Wozniak offered another theory. The two Steves were buying parts on credit with no savings, and the 10% partner might have felt he was on the hook for the money. In Wozniak's words, Wayne "was taking the majority of the risk and he only had 10%." You can hear both versions back to back. Was it the worst deal in history, or a sane exit from a startup with no cushion? Save this video to finish Wayne's story later.

Ray Dalio never went bankrupt, by his own account. He just had to borrow $4,000 from his dad after being right about Mexico, and he calls it the best thing that ever happened to him. CNBC has reported that he also had to lay off all of his employees at Bridgewater, the firm he had started. Dalio himself calls that period "one crash." Early in his career he calculated that American banks had lent far more to emerging countries than those countries could repay. By his account, the calculations were controversial and correct. Mexico then defaulted, and a wider debt crisis followed. Then he made the wrong call on the market. He expected the economy and stocks to fall a lot. "The economy and stock market went up a lot," he said. He lost money for himself and for his clients. In his words, "I was so broke that I had to borrow $4,000 from my dad." You can hear him say it, including how he describes that stretch. He called it "very, very painful," and also "the best thing that ever happened to me." It moved him from thinking "I know" to thinking "how do I know." The most important lesson, he said, was fear and humility, used to balance his bets. Do you learn more from your biggest loss, or from your biggest win?

Don Johnson took $5.8 million from the Tropicana at blackjack. The casino's answer, per its CEO, was to invite him back to host a $100,000 tournament and to raise its own lottery prize from $1 million to $5 million. In the video below, nj.com looks back at how Johnson won $15 million in Atlantic City and made headlines worldwide. The host first put the Tropicana's loss at $5.5 million, then corrected it to $5.8 million. Tropicana CEO Tony Rodio said the casino changed its marketing after all that publicity. The first move was a lottery. "We had this lottery where a customer could win a million dollars and we changed it to five million dollars." That is a prize five times larger. Rodio said the point was that you did not have to be a high roller like Johnson to win it. Next came a $100,000 winner-take-all blackjack tournament, with Johnson as the host. The casino also donated to a charity he supports, Jon Bon Jovi's Soul Foundation. Johnson said any win would go there too. Asked what he bought first with the $5.8 million, Johnson answered "Nothing." Rodio had a different memory. "I know he bought an expensive bottle of champagne somewhere along the way. I saw that photo." You can hear him say it, including the CEO's reaction. Is hosting the man who beat you smart marketing, or an expensive way to chase headlines?

Masayoshi Son was 17 when a photograph of a microprocessor made him cry on the street, he recalls. He predicted then that chips would one day outthink people, and gave it about 50 years. The SoftBank founder, who started the company in 1981, told the story on the Inside Blackstone podcast. He was asked whether his past bets, including Alibaba, Yahoo, Arm and the Vision Fund, were all just a warm-up. His answer was “Yeah, I truly think so.” What comes next in AI, he said, is “so remarkable, so big.” Then he explained where his conviction comes from. By his own account, he was reading a magazine on the street, saw the picture, and “physically, I start crying.” In his words, “this is going to change the future of mankind.” He reasoned that the microprocessor would eventually become smarter than people’s brain, and guessed it could take about 50 years. “It’s damn right, it’s now 50 years,” he said. He was 17 then and is 69 now. You can hear him say it, including the part about reading on the street. Son says that same technology is now moving into the brain of robots, which he says will bring it into the physical world. Is Son’s 50-year call a sign of rare foresight, or is it easy to look right with the benefit of hindsight?

Charlie Munger says he turned $70 million into "a billion dollars worth of property in about two seconds." The property is a ranch of about 1,800 acres near Santa Barbara, per the Independent, with two miles of ocean frontage, avocado trees and a private lake. Munger says its owner, the widow of the last grandchild of a major California oilman, needed to sell but could not. The county had denied the family's request to subdivide it, according to Noozhawk. The Independent reported the asking price fell from $108 million to $90 million. So Munger offered UC Santa Barbara $70 million. He had already given the school $65 million in 2014, its largest gift at the time, per Noozhawk. He knew, he says, that the university "is not subject to the damn Santa Barbara zoning rules." You can hear him say it. "I didn't get the billion, the university did, but I like helping the university." Both the Independent and Noozhawk reported that Munger bought the ranch to donate it to the school. The billion is Munger's own estimate. The university's chancellor said the school plans to keep it "as a working ranch." By his account, the same land was worth far more in a university's hands than in a family's. Clever workaround, or a billion-dollar guess? Save this video to finish Munger's story later.

Charlie Munger says he tried to shorten his own life with whipped cream. It didn't work. As a young man, he ate plenty of cream, animal fat and sugar. By his own account, he was afraid of spending his last years drooling into a cup in a nursing home. "I just kept living and living and living." Then Munger noticed something in his golf foursome. Two members of it outlived everybody else, and both had been late bloomers. At a birthday celebration a friend hosted at Harvard, Munger asked a famous medical professor, Atul Gawande, if late puberty and long life were linked. Gawande said, "I don't know." Munger went back to Los Angeles. A week later, he says, a big stack of research arrived. In both men and women, the later the puberty, the longer the life expectancy. Munger was "terribly pleased" with himself. The first night out, he told a "lovely young woman of about 60" about the correlation, brimming with his new knowledge. She called him by his full name and asked why he had to tell her this. She "started menstruating when I was 10 years old." You can hear him say it. The moderator later said Munger had just turned 95. As he tells it, the cream plan never worked. Longer life from late puberty, or just a lucky golf foursome?

On Sunday, August 18, 1991, Warren Buffett told the Treasury Secretary, "Nick, this is the most important day of my life." The Treasury had moved to bar Salomon Brothers, where he was the largest shareholder, from its debt auctions. By about 2:30 that afternoon, it had backed off in part. According to Fortune, Buffett spent the day on the phone arguing that the firm could not survive the ban. The Secretary, Nicholas Brady, kept taking his calls. Charlie Munger says Salomon might have gone under had Brady not relented on a key point. Brady went with Buffett because he trusted him. "It shows how having a good reputation is really helpful in life." You can hear him say it. Then Munger adds an irony. He says Brady's family once owned stock in Berkshire Hathaway, back when it was a textile company. At Harvard Business School, Munger says, Brady decided it was a lousy business and had his branch of the family sell out. The other branch kept its shares. Munger says that relative came to like Buffett, held on, and became enormously rich. "Life is full of little ironies like that," Munger says. He does not think it bothers Brady, whom he calls a pretty mature fellow. Was it reputation or luck that saved Salomon?

Warren Buffett, widely considered the greatest investor of all time, suggested his son use his Berkshire stock to buy time. The son sold it. CNBC once calculated those shares would be worth over $200 million. Peter Buffett got $90,000 of that stock at 19. It came from a family farm, he says in the interview. His dad disliked inherited wealth and misallocated capital, so he sold the farm and bought Berkshire stock. That left Peter with a choice. A house or a car, he says, and the money would be gone. With his dad's suggestion, he chose to buy time. The advice behind it was short. When Peter asked what to do with money, he says the world's most famous investor would answer T-bills. It fits the man Peter describes at home. He says growing up as Buffett's son was surprisingly normal, with the same house, no fence and a father who drove himself to work. Then comes a line Peter says his father is famous for. "Enough to do anything but not enough to do nothing." You can hear Peter say it. What Peter says he learned from his father was how to build a life his own way. He stayed in Milwaukee, much like Buffett stayed in Omaha instead of moving to Wall Street. The time went to music. In his memoir, he wrote that he does not regret it for a second. Was it a $200 million mistake, or the best investment he ever made?

John Daly, a five-time PGA Tour winner, lost an estimated $55 million gambling between 1991 and 2007. His career PGA Tour prize money, as of 2014, was $10.1 million, less than a fifth of that. Daly says he was shocked when the number came up, and his co-author could not believe it either. Daly had guessed $20 million or $25 million. He and his co-author went through his tax records to find the real figure. "I really didn't know." You can hear him say it. Asked how that is even possible, he gives a one-word answer. Stupidity. Seven blackjack hands at once, $5,000 to $15,000 a hand. By his own account, some sittings lasted a day and a half or two days, with breaks only for the bathroom. At one point he was up four or five million dollars and still ended up losing $2 million, he says, because he would not get up. On other trips, he says, he hit $60,000 to $80,000 on slot machines and walked out. Thinking you are going to win, Daly says, is the worst thing you can do in a casino. He will not claim to regret any of it. "I had a lot of fun doing it." By his math, that is about $3.1 million lost every year. Today, he says, he plays $25 slots and might move up to $100 if he hits something. Was it bad luck, or no plan for when to leave?

Michael Jackson, the King of Pop, paid $47.5 million in 1985 for 251 Beatles songs. According to a famous story, the man who taught him why songs are worth owning was Paul McCartney. In the video below, it starts in the early 1980s. McCartney reportedly showed Jackson a book of songs he owned and explained how much money owning songs could make. Jackson reportedly joked, "One day, I will own your songs." It probably sounded like a joke at the time. A few years later, it came true. Then the company holding those songs, ATV, came onto the market in 1984. After months of negotiations, Jackson's offer won, and he outbid Richard Branson along the way. Some people reportedly thought he had overpaid. The video says he was betting on what the songs could earn for decades. In 1995, he sold half of ATV to Sony for $95 million, creating Sony/ATV. In 2016, Sony agreed to pay his estate $750 million for the other half. Forbes had valued the whole venture at about $2 billion two years earlier. McCartney was reportedly unhappy, and in 2015 he filed a notice with the U.S. Copyright Office, a first step toward recovering his rights. Was buying the Beatles a genius bet, or the luckiest deal in music?

Warren Buffett, widely considered the greatest investor of all time, gave his kids an allowance. Then, according to his daughter Susie Buffett, he opened the back of a slot machine and took all of it back. She says they grew up in a very normal, father-knows-best household. The kids walked out the door the minute they got their allowance and spent it on candy and magazines. Her mother handled the money in the house. Susie kept her paycheck money from her own job in her room, and she says she never thought of her father as cheap. She uses the word thrifty. Then came the kitchen. Susie says she asked him for a loan and thought, "Oh come on, can't you do this?" She joked to her mother that she would end up on the cover of People magazine homeless, because her dad would be a super rich guy. He loosened up with age, she says, partly because her mother kept poking at him for years. "There's not an ounce of greed in him." You can hear her say it. She says he does not really care about the money, and that making so much of it was by accident. Watch his daughter's interview to hear how she describes the man behind the money. She says he made sure the money would do good in the world, and he does not care about owning 25 boats and 16 houses. Was the slot machine a lesson about money, or just good business?

In late 2016, Supreme Court lawyer Tom Goldstein won a staggering $26.4 million at poker in two months, according to his indictment. Less than a year later, he had lost more than $16 million to one man. By 2026, a jury had convicted him on 12 counts. In the video below, a poker creator walks through the indictment, including the text Goldstein sent after a $13.8 million win in Asia. "I've got the money. Let's go." You can hear it in the video below. Across 77 hours, prosecutors say, his gross winnings reached $50.8 million. He had coaches who took a cut and a 24-page memo built on computer simulations. Then the money went the other way. In February 2017, he lost more than $9.5 million to a California businessman. He was no longer backed by any pros and owed the loss immediately. In late 2018, prosecutors say, he flew home from Hong Kong with about $968,000 in cash in a duffel bag. In 2021, the IRS put a lien on his house over $1.3 million in back taxes. He also helped Tobey Maguire collect poker winnings from billionaire Andy Beal. The February 2026 verdict covered 12 of 16 counts, including tax evasion. His lawyers said most of the $50 million went to backers. Was the $26.4 million his biggest win or the start of his biggest problem? Save this video to finish his story later.

In May 2024, just before Berkshire Hathaway's first annual meeting without Charlie Munger, Warren Buffett made a staggering $8 billion in a single evening without placing one trade or lifting a finger. At least that is what investor Mario Gabelli said. In the video below, Gabelli, CEO of GAMCO Investors and a Berkshire shareholder who has known Buffett since the 1960s, explains how. Apple stock had just ticked up about 10 points after the market closed, he said. Berkshire's Apple stake was worth $135.4 billion at the end of March, after it sold an estimated 13% of its shares in the first quarter. Even without Apple, the cash pays him. Berkshire held $189 billion in cash, and at 5% that is roughly $9.5 billion a year, if all of it earned that rate. "If he sits back and does nothing and yawns, he's making 5% T-bills." You can hear him say it in the video below. Gabelli added that Berkshire's Japan holdings grew from $15 billion to $25 billion in a year, even with the yen at 155 versus 133 the year before. So the question for Buffett is what he wants to own next. When cash pays 5%, every stock has to beat doing nothing. Would you rather own a stock that jumps overnight or cash that pays you while you wait?

Peter Lynch, the man Time magazine called America's number one money manager, walked away in 1990 from the job that made him famous. At the very top of his game, he left by choice. In the video below, he explains why he quit after 13 years of running Fidelity's Magellan Fund in Boston, a top-ranked general equity mutual fund. He said he adored the job. He also said he left home at 6 in the morning and got back at 7 at night, six days a week. On top of that, he traveled 14 days a month. He called it just too much. His kids were getting older, and older kids need more than a bedtime story. He could afford to stop, because he had already made enough money. That meant he did not have to give up his family or his outside activities. So he cut his week from 80 or 90 hours to 40 or 50. Now he makes breakfast and lunch for the kids and does spelling and Spanish words with them. His wife handles the math and science. Then he goes to an office every morning, because he says you have to go somewhere to do something. Most of his time goes to charity work, including inner city schools, libraries and housing. "I said that's it, I can't take it." You can hear him say it in the video below. Few people at the top of any field get to choose their hours. He chose his. Top job in your field or your evenings back. Which one do you pick? Save this video to finish Lynch's story later.

In 1985, Warren Buffett, who would later rank among the five richest people in the world, put $517 million behind the deal that let Capital Cities buy ABC for $3.5 billion. Around that deal, he said on TV that he might not make an investment for two years. The host puts his net worth "far in excess of 500 million dollars." Asked how he could stay away from Wall Street, Buffett says he would probably be "a lot poorer" there. You can hear him say it in the video below. His whole method, he says, fits in two rules. The first is don't lose. The second is don't forget the first. Then comes baseball. "There are no called strikes in the business." In baseball, a pitch between the knees and the shoulders forces you to swing or take a strike. In investing, he says, "the pitcher just stands there and throws balls at you." You can watch thousands of pitches until one is "something that you understand." Then you swing. "You might not swing for six months, might not swing for two years." Buffett says that would bore most people. Clients of professional managers start yelling "swing, you bum" from the stands. Watch his full interview to hear why he never bought a technology company in 30 years. He says he did not understand them. "I don't have to make money in every game." Is waiting two years a strategy, or a luxury only a rich man can afford?

Charlie Munger says Bill Ballhaus made "many millions of dollars" by raising the price of one product. In the video below, Munger says Ballhaus ran Beckman Instruments, a company founded by a Caltech professor. One of its complex products sold for less than two competitors, and Munger says it was much better. Its financial numbers were bad. Ballhaus took one look and saw the problem. If this product failed, it imposed enormous costs on the owner. A low price sent the wrong signal. Buyers would think, in Munger's words, "this can't be very good." So he raised the price "enormously," Munger says, and sold way more units. Profits went up "in a truly dramatic way." In another telling, Munger put the increase at about 20%. Munger says only about 1 in 50 people with business school training can name a case where raising the price sells more. The usual answer is luxury goods, where price signals quality. He says the rest are leaving a lot of money on the table, and the world is full of opportunities like that. Passing a test, he says, "won't get you the many millions of dollars Ballhaus made by raising the price." It also will not get you "really fabulous investment results in life." Would you have had the nerve to raise it?

Warren Buffett says he and Charlie Munger never had a single argument, in a partnership that lasted more than five decades. People tell him that is impossible. "I'm telling you we've never had an argument," Buffett says. They met in 1959 at a dinner party in Omaha. Munger was a lawyer in Southern California. Buffett ran an investment partnership in Omaha. Both had worked at the same family grocery store, but Buffett says they never met there. Munger became vice chairman of Berkshire Hathaway in 1978. Buffett later said he would call Munger for advice on every major decision. Buffett says they did not agree on everything. When one of them believed something, the other would say what he believed, and they did not argue about it. Then Buffett names the people he least wanted to disappoint. After his father, he says, it was Munger, along with Tom Murphy and Joe Rosenfield. In 2008, Buffett said, "Charlie has taught me a lot about valuing businesses and about human nature." In this interview, he calls the relationship "the best" he has had outside of family. Munger died in November 2023, at 99, just over a month before his 100th birthday. Who in your life do you least want to disappoint? Save this video to finish Buffett and Munger's story later.