Warren Buffett made his son pay rent on a 400-acre farm, priced by his body weight. Howard Buffett didn’t know he was rich. His sister told her class their dad was a security guard. He was a security analyst. Howard tried 3 colleges. He finished 0. Warren wasn’t worried. “It made no difference to me whether he found it in a college or not.” Then Howard chose farming. Warren bought the land. Howard paid the rent. The terms: Target weight: 182.5 pounds. Howard weighed about 200. Over the line: 26% of gross income. Under it: 22%. “Financial incentives are supposed to work in some things,” Warren said. “They don’t work very well at weight.” Why not just give him the farm? “I don’t think he’s entitled to be given a farm just because his last name is Buffett.” September 18, 2026. Howard, 71, became chairman of Berkshire Hathaway. Warren wouldn’t give his son a farm. The board gave him a $1 trillion company.

Anna Nicole Smith won $474M from her late husband's fortune. 11 years later, her estate got $0. In 1995, she sits in Howard Stern's studio. Her husband, oil billionaire J. Howard Marshall, is in the hospital. "He's very sick." They married in 1994. She was 26. He was 89, worth about $1.6B. Prenup? "I didn't sign a prenup." His son Pierce controls the money. "He's absolutely evil." Will she get anything? Not even $1M? "Nothing." "My husband doesn't even know what's going on." Stern asks: "Are you just waiting till he goes?" "I'm just waiting." In August 1995, Marshall died at 90. His will left her nothing. In 2000, a judge awarded her $474M. In 2002, another judge cut it to $88M. In 2006, the Supreme Court let her keep fighting, 9-0. Weeks later, Pierce died at 67. In 2011, the Supreme Court ruled 5-4 against her estate. She died in 2007, at 39, still waiting.

Hulk Hogan told CNN he couldn't believe his best friend filmed him. The friend paid $5,000. A jury hit Gawker for $140M. CNN, October 2012. Gawker has posted 1 minute 41 seconds of his 30-minute sex tape. About 7M people will watch it. "I had no idea there was a camera set up." Piers Morgan asks who betrayed him. TMZ points to Bubba the Love Sponge. Tampa radio host. The woman on the tape is his wife. "He's been such a close friend. I would have to see that to believe it." TMZ says the tape keeps rolling after Hogan leaves. Bubba turns to his wife. "If we ever did want to retire, all we'd have to do is use this footage." Hogan sued. Within weeks, Bubba settled. $5,000 and an on-air apology. Gawker fought for 3 years. In March 2016, a Florida jury hit it for $140M. 3 months later, Gawker was bankrupt. Earlier in the interview, one line. "Sometimes you don't even know if they're your friends."

Michael Jackson died $500M in debt. In 4 years, his estate made over $600M. That is the $500M from the post below. $380M of it was borrowed against the songs he owned. "He never stopped spending like it was the 1980s," Forbes' Zack O'Malley Greenburg told 60 Minutes. His lawyer, John Branca, took over the estate. To keep the songs from creditors, he sold future music rights to Sony. A reported $250M. The real prize was other people's songs. In 1985, Branca helped Jackson buy the Beatles catalog. "The price was $47.5 million." Jackson later merged it into Sony/ATV. The estate owned half. In 2013, Lara Logan asked what that half was worth. Branca: "You never really know what something's worth until you go to sell it, and we are not sellers." "We are not going to sell any assets." By then, the debt was gone. In 2016, the estate sold its half to Sony for $750M. Jackson told Bashir he was good with money. On one deal, he was. $47.5M in 1985. $750M in 2016.

Michael Jackson told Martin Bashir he was worth over $1B. In 2009, he died more than $500M in debt. Las Vegas, 2002. "I remember getting $200,000 checks in the mail when I was like 12, 13 years old." Bashir asks what he's worth now. "It's way up there." "Come on, Martin. I've done really well." Over $1B? He says yes. Then his favorite store in town. "See, this is the shop. I bought so much stuff here." 2 urns. $275,000 each. Bashir guesses the bill at a couple of million dollars. The manager won't say. Later, Bashir put the day at $6M. To Bashir, it looks like Louis XIV's palace. "It's my taste." In 2005, a forensic accountant testified. His finances at the time of the documentary: $415M owed, about $130M in assets. He was spending $20M to $30M a year more than he earned. In June 2009, he died owing more than $500M. One question came before the shopping. "Have you always been good with your money?" "With my money? Yes."

Elizabeth Holmes told Charlie Rose her finger-prick test gives the same results as a lab. A year later, Forbes cut her $4.5B to $0. She started Theranos at 19. By 2014, investors valued it at $9B. Her board: Henry Kissinger, George Shultz, James Mattis. "Same results as a vial of blood from your veins?" "We do." In October 2015, the Wall Street Journal looked inside. Her machine ran only about 15 of 240+ tests. The rest ran on ordinary machines from companies like Siemens. In 2016, Theranos voided 2 years of its device's results. Forbes cut her to $0. Rose had asked if being worth $10B mattered to her. "Yeah, it's not what matters." In 2022, a jury found her guilty of fraud. 11 years and 3 months in prison. In 2023, a judge ordered $452M paid to victims. Big labs only wanted to know how the test worked. "We don't think that we need to explain ourselves to competitive companies."

Warren Buffett went 30 years without buying a tech stock. His Apple stake later hit $174 billion. In 1985, a TV host can't believe it. "In 30 years of investing, not one?" "I haven't understood any of them." "Never owned IBM. Marvelous company." "It's gone right past me." "There are no called strikes in the business." The market throws pitches all day. US Steel at $25. General Motors at $68. "You don't have to swing at any of them." You can watch for 2 years. Most managers can't. "Boredom is a problem with most professional money managers." In 2011, he finally swung at tech. $10.7 billion on IBM. IBM went nowhere. By 2018, he owned zero. In 2016, Berkshire swung at Apple. $1 billion at first, $35 billion by 2018. At the end of 2023, the stake was worth $174 billion. He had described that pitch 31 years earlier. "Something that you understand, and then you swing."

Muhammad Ali, 30, told Johnny Carson why champions go broke. At 38, he was still taking punches for $8M. November 1972. The Tonight Show. A ban had cost Ali over 3 years of his prime. The Frazier fight paid $2.5M. Carson asks if he'll end up broke. Beau Jack, a former champion, is "shining shoes somewhere down in Florida." Ali blames the men around the fighters. "He cannot watch his money. He cannot watch his accountants. He cannot watch his lawyers or his managers." "Half of them are crooked and conniving." The managers went to school for money. The fighter didn't. "They always remember the name Joe Louis." Louis made millions. He ended up owing the IRS over $1M and greeting tourists at Caesars Palace. And Ali's own money? "I have accountants and everybody checking everybody." 8 years later, he lost to Holmes. Parkinson's followed in 1984. In 2006, he sold 80% of his own name for $50M. The money held. The body didn't. "It won't be because I wasn't watching."

Warren Buffett gave Bill Gates $31 billion. His own kids got $1 billion each, for charity. People called Gates "Warren's third son." Vacations together. Birthdays together. June 2006. Warren pledges $37 billion to 5 foundations. Gates gets the biggest share. His son Howard knew it growing up. The bulk of the money would never be his. "From time to time that was a little frustrating." Sibling rivalry? "No." "Maybe." "That's why we call him brother Bill." "Bill Gates is the smartest guy in the world. Next to my dad, maybe." In 2021, Warren quits as a Gates Foundation trustee. In 2024, he changes the plan. "The Gates Foundation has no money coming after my death." More than 99% of his fortune will go to a charitable trust. About $130 billion at the time. 3 trustees: Howard, Susie and Peter. Howard paid rent on a farm. Now he helps decide where the fortune goes.

Days before Bernie Madoff was arrested, a 58-year-old Manhattan lawyer was caught in a $400 million fraud. Almost nobody remembers him. Marc Dreier ran a firm of 250 lawyers. His name was on the door. It wasn’t enough. “I wanted to be as important as I thought I deserved to be.” He had one client whose name could open any wallet: Solow Realty, a billionaire’s real estate company. Dreier sold hedge funds promissory notes from Solow. The notes were fake. So were the financial statements. So were the audits. “Well, I invented it.” His biggest single deal: $100 million. Nobody called Solow to check. The money bought the look of a billionaire. A 120-foot yacht called Seascape. $18 million. A crew of 10. A $10.5 million apartment in Manhattan. A Picasso, 3 Matisses and 12 Warhols. December 2008. Toronto. He walks into the Ontario Teachers’ Pension Plan posing as its own lawyer to sell a $45 million note. This time, someone checks. Toronto police arrest him that day. In July 2009, a judge gives him 20 years. He didn’t hide the stolen money. He used it as bait.