Dan Bilzerian says he has flipped a coin for $6,000,000. He also says he came close to betting $2,000,000 on Floyd Mayweather against Manny Pacquiao, a bet Aria’s CEO Bobby Baldwin personally approved. In the video below, he explains why he walked away from that one. If Mayweather lost, Bilzerian figured, he would get a guaranteed rematch worth maybe $250,000,000. Losing might have been the best payday of his life. He says one current NBA star, whom he won’t name, lost about $12,000,000 gambling over just a few games. When that player had been up for 24 hours straight, Bilzerian bet against his team. Then there was the ocean. A man bet he could row solo across the Atlantic in 30 days. Bilzerian put up $500,000 against his $50,000. The rower built an ultralight 3-hull boat and packed food for only 30 days, because winning the bet was the whole point. Bilzerian started to think he might make it. So he bought his way out. He says he couldn’t stand checking GPS reports and losing sleep for a month. A coin flip for $6,000,000 is over in a second. A bet you have to watch for 30 days costs you every night. Is it the size of a bet that scares you, or how long you have to live with it?

Antoine Walker says he used his first big NBA check to buy his mother a house. He went on to earn more than $108,000,000 in salary, and two years after his last game he filed for bankruptcy with $12,700,000 in debts. In the video below, he explains where all of that money went. The Celtics drafted him 6th overall in 1996, when he was 19. He played 13 seasons, made 3 All-Star teams and won a title in 2006. He says he owned 5 or 6 cars at a time, including Bentleys and Maybachs, plus a collection of Rolexes. He traveled with 8 to 10 friends from his neighborhood and paid for their flights, hotels and meals in Cancun, Puerto Rico and Las Vegas. He had a financial advisor. He admits he was too young and too proud to listen. He lost a big chunk gambling in Vegas, and by 2009 he faced felony charges over bad checks to casinos tied to more than $800,000 in gambling debts. Real estate finished the job when the market crashed in 2007 and 2008. When he filed in 2010, he listed about $4,000,000 in assets against those debts. Was Antoine Walker generous with the people he grew up with, or did he pay for a lifestyle nobody could afford?

In 2015, Elon Musk co-founded OpenAI to help make sure artificial intelligence turned out well for humans. In 2024, his own AI company, xAI, raised $6 billion at a $24 billion valuation. By then he had spent years warning about where the technology was heading. In the video below, he explains why he doesn’t expect humans to stay in charge. “I find it unlikely that humans would remain in control if there’s a million times more digital intelligence than there is biological intelligence,” he said. “So I hope the AI is nice to us.” His proposed fix isn’t a kill switch. It’s what the machines read. AIs are trained on everything online, he pointed out, and the internet is full of robot apocalypses. A model that has read 80 versions of the Terminator script might decide that’s simply who it is. So he wants more hopeful stories in the training data, enough that an AI might picture itself as a friendly overseer or a gardener instead of a killer robot. The goal itself needed changing too. A friend of his prefers protopia to utopia, because chasing a perfect world usually ends in a dystopia. A protopia is a future we can actually reach, not perfect, but good. Then he named what he’d build in from the start: truth-seeking and curiosity. Billions of dollars build the machine. What it turns into may depend on the stories it was raised on. If an AI learned everything about money from what you post online, what would it think money is for?

In 2021, Scarlett Johansson sued the most powerful studio in Hollywood over one clause in her contract. Disney settled within months, reportedly for more than $40 million. Years later, she was asked whether taking on Disney, and then OpenAI, ever scared her. “I felt right in my stance. And so then I didn’t feel scared,” she said. Then she added: “I believe very much in integrity.” The interviewer asked if she felt lonely. “Some, yeah, maybe a little bit,” she admitted. Not everyone is comfortable standing up to a large corporation, “or, you know, the man.” She didn’t move. “I can shoulder the burden.” Her contract promised Black Widow an exclusive run in theaters. Disney released it on Disney+ the same day for $30. Her pay depended on the box office. In 2024, OpenAI pulled its “Sky” voice after she said it sounded like hers. She had turned down Sam Altman’s offer to voice it. She could fight because she knew exactly what her contract said and what she was owed. Most people never check. Pew found about 70% of US workers did not ask for higher starting pay. Of those who did ask, 66% got more than the first offer. The fix is to know your terms before you need them. Read your offer, your bonus rules and your raise policy. Write down what you’re owed. Ask once, in writing. People have told Johansson her fight changed how they negotiated their own contracts. When was the last time you read your own contract?

SpaceX made $7.6 billion from AI in a single quarter, and Elon Musk says it could have rented its compute several times over. According to him, years-old Nvidia H100 chips now rent for more than they did when they were brand new. It came up on SpaceX’s third-quarter earnings call this week. “Our belief is that the value of compute per watt will increase over time, not decrease,” he said. Then he added: “We are also, frankly, hounded relentlessly by every hyperscaler.” Wall Street has spent months worrying that the world is building too many AI data centers. Musk didn’t move. He said SpaceX tried to rent extra chips from other clouds and got the Monty Python cheese shop. No GB300s. No GB200s. No TPUs. Maybe some H100s overseas. Then no H100s either. AI made up 52% of SpaceX’s $14.6 billion in quarterly revenue. Its short-term compute contracts are renewing at higher dollars per watt. CoreWeave and Nebius stocks jumped 5% and 6% overnight. Musk keeps contracts short because he expects the price of what he sells to rise. Most people do the opposite with the one thing they sell: their time. A salary is a long contract at last year’s price. Freelancers sign 12-month retainers and never revisit the rate, even as their skills get more valuable. The fix is to shorten the contract on anything that is going up. Check your market rate every year. Ask for a raise at review time. Reprice freelance clients every quarter. Every renewal is a raise you can ask for. When was the last time you repriced your time?

Elon Musk is the richest person alive. He says going from $1 billion to $10 billion “doesn’t make you 10 times happier.” He said it while describing a future where AI and robots can make almost anything anyone wants. “Money becomes irrelevant,” Musk said. Currency, he guessed, would be measured in “wattage and tonnage.” Then he added: “There’s a limit to what any single human can consume. You hit that saturation point pretty fast.” A historian on stage pushed back. In the 1890s, new technology created robber barons, and people picked up pitchforks. Musk didn’t move. Past a certain point, he said, a fortune stops being consumption. It becomes “resource allocation.” The research backs the first half. Kahneman and Deaton found emotional well-being leveled off around $75,000 a year. A 2023 follow-up found it keeps rising for most people, but on a curve. Each doubling of income buys about the same bump, so $50,000 to $100,000 feels like $100,000 to $200,000. Musk can talk about saturation because he passed it billions of dollars ago. Most people never notice where theirs is. Every raise goes into a bigger apartment and a newer car, and each upgrade costs more for the same small lift. The fix is to split your money the way Musk describes. Spend raises on what clearly makes daily life better, like time, health and less stress. Past that point, send the rest to savings and investments. A dollar beyond your saturation point does more as an asset than as stuff. At what income would another upgrade stop making you happier?

In late 2021, Elon Musk was worth close to $300 billion on paper. In the same interview where he was asked to apologize for it, he admitted his cash balance was “very, very low.” The interviewer kept circling back to whether that much wealth was fair. Musk tried to explain what the number actually was. “It’s not like I’ve got some massive cash balance,” he said. “I simply had loans against my stock.” Then he added: “If Tesla and SpaceX went bankrupt, I would go bankrupt, too, immediately.” The interviewer pushed again. “So you’re not apologizing right now? Look in the camera.” Musk didn’t move. He said he never sold because a captain should go down with the ship. Even when bankruptcy was weeks away, he kept his shares. Tesla crossed a $1 trillion valuation that October. Musk owned about 20%, roughly $200 billion. By mid-December he had sold about $12.7 billion of stock, much of it to cover a tax bill CNBC estimated at $15 billion. Musk could keep everything in one ship because he was the one steering it. Most people hold the same structure with none of the control. Their net worth is a house they can’t spend, a 401(k) they can’t touch, and stock in the company that already pays their salary. Their cash is “very, very low” too. The fix is to separate wealth from money. Keep three to six months of expenses in cash. Cap your employer’s stock at a small slice of your portfolio. Cash you can reach keeps a bad month from turning into a forced sale. If your income stopped tomorrow, how much of your net worth could you actually spend?

In 2021, about 90% of Twitter’s $5 billion in revenue came from one source: advertisers. Two years later, the man who bought it told those advertisers, on stage, to go f*** themselves. It happened at the 2023 DealBook Summit. Andrew Ross Sorkin asked Elon Musk about the brands that had pulled their ads from X. “If somebody’s going to try to blackmail me with advertising, blackmail me with money, go f*** yourself,” Musk said. Then he added: “Hey, Bob, if you’re in the audience.” Disney CEO Bob Iger had spoken earlier that day. Sorkin noted that X’s CEO, Linda Yaccarino, sold ads for a living and was sitting in the room. Musk didn’t move. If the boycott killed the company, he said, the whole world would know who did it. WARC projected X’s 2025 ad revenue would fall below $2 billion for the first time in over a decade. In March 2025, Musk’s own AI company, xAI, bought X in a deal that valued it at $33 billion, down from the $44 billion he paid. Yaccarino resigned that July. Musk could afford to say it because he had billions coming from somewhere else. Most people have the same setup Twitter did, with a much smaller cushion. One employer pays 100% of their income. When that one source makes a demand, there is no real way to refuse. The fix is to lower the share. Build savings that cover six months of expenses. Add a second income stream, even a small one. Every dollar that doesn’t depend on one boss is a dollar of freedom to say no. How many months could you last if your biggest source of money disappeared tomorrow?

Phil Ivey has won more than $55 million at live poker tables, and he needed four minutes to show that talent is a weak explanation for winning. Away from the table he writes down any hand he might forget and replays it, asking what his opponent was thinking and what he should have done differently. He admits he has never played a perfect session. “Every time I play a session, I always make mistakes.” Some weeks he puts in 100 hours. He also studies how others lose. Opponents on a bad night play “really, really terrible,” he says, so he might quit early against a winner and stay two days with a loser. At 18 he played in Atlantic City on a $50 fake ID and lost often. He now has 11 World Series of Poker bracelets, second only to Phil Hellmuth, and a place in the Poker Hall of Fame. His method works on a bank statement. Once a month, write down your three biggest money decisions and ask what you would do differently next time. Your savings rate, one subtraction and one division, shows whether the replays are working. His second rule protects you from yourself. People decide worst right after a loss, so a bad month is the wrong time to sign a lease, buy a car or sell your investments. Ivey’s video on how he studies poker is free on YouTube and runs four minutes. Almost nobody finishes it. “I’m not a prodigy,” he says near the end. “I just work at what I do.”

Netflix paid $587 million for Ben Affleck’s AI startup. Affleck describes his own coding skills as “pretty shitty Python scripts.” The second fact explains the first. The most profitable skill level in a new technology is bad enough to understand what the experts are talking about. That bad code came from years around visual effects. Hollywood VFX has used machine learning for a long time, mostly to find edges in a frame, separate a window ledge from a green screen, clean up a shot. Before Artists Equity, Affleck ran a small VFX company and got used to working with GPUs. He never became an engineer. He learned enough to follow one. When VFX people told him Google and OpenAI were doing something new with transformers and video, he didn’t need it translated. He called and asked to see it. The company he founded, InterPositive, builds AI tools that train on a film’s own footage to relight shots and remove wires. Netflix bought it in March, and Affleck now advises the streamer. Most people wait to touch a new tool until they can use it well. That keeps them at zero, and from zero you can’t even tell whether the tool matters. The jump from zero to bad is the cheapest one you will ever make. A weekend with a free coding course, a new spreadsheet function, an AI tool pointed at your actual work. You won’t be good. You will know which questions to ask, which tasks it can replace, and who is overselling it. Bad Python on top of decades in film turned out to be worth $587 million. Which tool in your field are you still at zero on?

Living in a home that costs $1,000 a month less than you can afford, and investing the difference at 7%, adds up to about $1.2 million over 30 years. Housing is the biggest bill most people have, and few of them run that number before signing. Warren Buffett made that call in 1958. He bought a house in Omaha for $31,500 and never moved out, even after he became one of the richest people alive. In the video below, his granddaughter Nicole explains how that thinking runs the whole family. Buffett paid for her education and her living costs while she was in school. After that, she got nothing. In 2006, while he was worth more than $40 billion, she was organizing toys for a wealthy family in San Francisco. She says her grandfather would never want any of his children or grandchildren to live flashy. He thinks it would rob them of their own experience. Most people do the reverse. Every raise turns into a bigger apartment, a newer car, a nicer neighborhood. The income goes up and the amount kept stays flat. Buffett’s version is simple to copy. When your pay goes up, keep your housing where it is and invest the gap. Housing is the one cost you set once and then pay every month for years, so it moves your savings more than any coffee you skip. Nicole still admits she sometimes wishes she could stop worrying about money. Her grandfather has given away more than $60 billion from the same corner house. What would you do with an extra $1,000 a month?

Before Brian Tracy crossed the Sahara, the people around him kept saying the same thing: you’ll die in the desert. He was about 20, with roughly $300, trying to get from Vancouver to Johannesburg across three continents. In the video below, Tracy explains why he stopped listening. He quotes a line he still repeats: “If every possible objection must first be overcome, nothing will ever get done.” The warnings were not invented. The trip was one problem after another. They ran out of money over and over. Their Land Rover kept breaking down. They had dysentery and heat stroke before they ever reached the sand. Tracy says those problems are the reason they survived. By the time they reached the Sahara, every breakdown in Europe had already taught them something they would need there. “Difficulties come not to obstruct but to instruct,” he says. They reached Johannesburg in just under 12 months. His advice is to get away from the naysayers. “Fly with the eagles,” he says, and refuse to listen to every reason why you can’t succeed. Money decisions come with the same chorus. Starting a business is too risky. The market is about to crash. Asking for a raise will backfire. Most of it comes from people who never tried. The naysayers were right about every danger in the Sahara. Were they right that Tracy should have stayed home?

In January 2026, Rick Rieder was the prediction-market favorite to become Fed chair. Trump picked Kevin Warsh instead, and Rieder kept running BlackRock’s $2.4 trillion bond business. In the video below, Rieder describes what the stock market looks like from his desk. He calls it “much more of a gambling arena” than anything he has seen in nearly four decades of trading. He explains how he trades against it. When chip stocks tripled, people kept buying call options that only paid off if the shares rose another 50 or 60 percent. Rieder sold them those calls. “You get paid real premium,” he says. “That was unbelievable.” He was ready to sell the stock at those prices anyway. The buyers paid him for a decision he had already made. He calls it “sleeves off your vest.” When fear spikes, he does the reverse. He sells puts on companies he wants to own about 15% lower and collects money while he waits. Rieder says zero-day options, leveraged single-stock ETFs and funds that sell volatility for income have filled the market with cheap options. He buys those too, and his team tracks the same crowds in Korea and Japan. He also admits the job costs him. He says he has never worked harder or been under more stress, and sleep is the first thing he cuts. The call buyers needed a stock that had already tripled to keep climbing. Rieder only needed it to stop. Who was really gambling in that trade?

Warren Buffett ran Berkshire Hathaway for 60 years and turned its stock into a 5,502,284% gain from 1965 to 2024. His first lesson in markets came at 21, from an insurance agent named Moose who would not take free money. Kansas City Life was a solid, well-known insurer. Its policies assumed 2% interest. Its stock sold for less than three times earnings, so buyers got about 35% of the price back in earnings every year. Buffett went to the local agent, who had worked there 20 years. His paycheck came from that company. His family’s policies depended on it. “Stocks aren’t any good,” Moose said. Buffett called himself a lousy salesman and admitted he sometimes wondered if he was the crazy one. Then he watched it happen at scale. In 1970 pension funds put more than 100% of their net new money into stocks. By 1978, with stocks far cheaper, that fell to a record low of 9%. The Dow closed 1964 at 874 and 1981 at 875. He told the students it doesn’t take brains. “It takes temperament.” Moose never ran one division comparing 2% to 35%. Most people never run the one on their own paycheck either, one subtraction and one division that shows how much of it they keep. His full answer is free online. Most people scroll past it. Moose spent 20 years selling 2% policies inside a company earning 35% on its stock price.

Leonard Cohen spent five years cooking for an 87-year-old Zen master on a mountain outside Los Angeles. A few years after he came down, his retirement money was gone. At 73 he went back on tour, and he was still on the road at 79. On Mount Baldy he was given a monk’s name, Jikan, which means “silent one.” He worked as cook and personal assistant to his teacher, Joshu Sasaki Roshi. In 2004, at 70, he learned that his savings of more than $5 million had shrunk to about $150,000. His longtime manager, Kelley Lynch, was accused of taking it. In the video below he is asked whether it was important to rebuild his nest egg. “It was a matter of financial survival,” he says. “It’s important to produce some income. So I got busy.” “You can put forward your best effort, but there’s no guarantee,” he adds. “Nobody can do that.” Between 2008 and 2013 he played about 370 shows on two world tours. In 2014, at 80, he said getting back on the road had improved his mood “considerably because I was never good at civilian life.” In 2012 Lynch got 18 months in jail for harassing him. In court Cohen wished her “a spirit of understanding” that would “convert her heart from hatred to remorse.” A man trained to want almost nothing still needed an income at 73. Savings can be taken. The ability to earn stays where it is. Would you have gone back to work at 73, or made peace with $150,000?

Rick Rieder oversees $2.7 trillion at BlackRock, and he showed why he only needs to be right about 60% of the time. The other 40% decides whether he survives. The rule came from a mistake right out of school. He bought a bond, the market turned, and he bought more because he was sure he was right. He learned to cut size so no single position could ruin him. Then came Peloton. He was one of its original owners, Covid pushed the company toward a $50 billion valuation, and he held on. The stock later lost more than 90%. His fix is to invest the way a casino runs its tables. Diversify, keep liquid assets, win 60 to 65% of the time across many bets, and use a stop loss. Rieder launched a hedge fund months before the 2008 crisis. BlackRock bought it in 2009, and he has run its bond business since. A household runs on the same math. Your savings rate is one subtraction and one division, and it decides how big a loss you can absorb before a bad month forces you to sell at the bottom. His Hard Lessons interview with Morgan Stanley is free on YouTube and runs 19 minutes. Almost nobody finishes it. He plans an exit for every position he owns. He also says that if you have never missed a flight, you are not taking enough risk.

Phil Ivey has won 11 World Series of Poker bracelets and over $54 million in tournaments. In 2012 he won about $20 million at baccarat, a game of pure chance, without ever touching the cards. The method is called edge sorting. Casino cards are cut unevenly, so a trained eye can tell some of them apart by the pattern on their backs. Ivey asked for things. One brand of cards. The same decks all night. A shuffle machine that keeps cards in order. A Mandarin-speaking dealer, so his companion Cheung Yin Sun could ask her to turn certain cards. Both casinos said yes to everything. He had wired £1 million to Crockfords in London and $3 million to the Borgata in Atlantic City up front. He walked out £7.7 million ahead in London and $9.6 million ahead in Atlantic City. By his own estimate the edge was 5 or 6 percent. Baccarat normally gives the house about 1 percent. The UK Supreme Court ruled in 2017 that it was cheating. A US judge ordered him to return $10.1 million to the Borgata. A house edge is a small percentage applied to every hand. Your savings rate works the same way on every paycheck, one subtraction and one division, and whoever controls that percentage ends up with the money. The full interview is free online. Almost nobody finishes it. Crockfords never paid him a penny of the £7.7 million.

This MIT lecturer explained why most people should think twice before starting a company. The reason is uncomfortable. The man who built a $5 trillion company said he wouldn't do it again. Joe Hadzima opens his MIT course with Jensen Huang. Huang co-founded Nvidia in 1993, and in October 2025 it became the first company ever to hit that number. On the Acquired podcast he was asked if he would start a company again. "I wouldn't do it." Building Nvidia was "a million times harder" than he expected, and with all the pain and shame up front, "nobody in their right mind would do it." Then Hadzima puts up the numbers. About 1 in 10 startups succeed. Kleiner Perkins, in his words the most successful long-term VC firm, with all its money and connections, won about 3 times out of 10. Hadzima has been a startup lawyer, co-founder and investor for decades and has run this course since the late 1980s. You don't need to quit your job and bet your savings to build something. A one-person business that sells what you already know costs almost nothing to test. Keep the paycheck until strangers pay you. Then decide how big you want it. Hadzima's full lecture is free on MIT OpenCourseWare and runs 69 minutes. Almost nobody finishes it. Huang got the $5 trillion company. He still said nobody in their right mind would start it.

A Stanford venture capitalist showed how a group of investors got their $5 million back and walked away from a company Elon Musk later bought for $44 billion. In her lecture she sorts every startup portfolio into three groups. Unicorns are the billion-dollar outcomes. Dragon eggs could become one. The walking dead keep operating but will never return the fund. Her example was Odeo, a podcasting startup founded in 2005 with $5 million from Charles River Ventures and angels. That summer Apple put podcasts into iTunes, and Odeo stalled. In 2006 co-founder Evan Williams bought the company back, paying enough to make the investors whole. A side project came with the deal. It was called Twitter, and it went public in 2013. The lecturer is Ernestine Fu. She joined Alsop Louie Partners at 19, while still a Stanford undergrad, and later earned four Stanford degrees, including a doctorate. Most people handle their own small bets the way Odeo's investors did. A stock that went nowhere for three years, a side business that barely covers its costs. The moment it gets back to break-even, they sell to feel safe. Before you cash out of something just to get your money back, write down everything that leaves with it. Fu's full lecture is free on Stanford's YouTube channel and runs 41 minutes. Almost nobody finishes it. Odeo's investors got every dollar back and kept none of Twitter.

Every new hire should watch this lecture before their first boss asks for "just this one weekend." Clayton Christensen spent decades at Harvard explaining how smart companies make logical decisions that destroy them. At LinkedIn, he showed the same math running people's lives. In 1989, U.S. Steel engineers wanted $300 million for a mini mill to make sheet steel. The CFO said no. The old mills sat 30% empty, and one more ton there cost $15. Christensen said that mill would have returned $3 billion over two decades. The cheap option wins every quarter. Use the old mill, the old sales team, the old brand. A startup has none of those, so it builds the new thing and takes the market. He called it marginal cost thinking. Each decision is judged by today's cost, and the full cost, which you almost always pay, shows up years later. He never let it into his own life. At Boston Consulting Group, a manager wanted him in on a Sunday, then a Saturday. He refused both, because life is an endless stream of extenuating circumstances, and a rule is easier to keep 100% of the time than 98%. Decide your lines before the pressure arrives. In the moment, the exception always looks cheap. Your paycheck follows the same math. One subtraction, one division, and each small purchase looks harmless until you add up the year. He gave this talk a year and a half after a stroke, in English he relearned with Rosetta Stone. How many of your "just this once" moments happened more than once this year. The whole talk is attached. Watch it before your next exception.