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Money stories from Wall Street to Hollywood | The more you watch, the more you attract

Joined May 2023
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Mark Cuban's teenage son kept showing him get-rich-quick videos. Dropshipping. Shoe drops. A pressure washer business for sidewalks. Cuban's answer: "If those were good businesses, they wouldn't be telling you about them." He told Steven Bartlett the algorithm feeds you more of whatever you watch, so the schemes just keep coming. Same with markets: "Nobody who has an edge in the stock market is selling it. They're using it." What he says works instead: 1. Learn the new thing before everyone else. When PCs were new, he stayed in the store overnight reading software manuals. Now he says the same about AI: "There's the creator and everybody else is tied for second." 2. Get great at one thing. "Once you're great at something, doors open up wide." 3. You don't have to raise money. His first company was profitable every single month for 8 years, then sold for $5 million. In the video below, he tells Bartlett about the videos his son showed him. Listen for what he says about people selling stock market secrets. Try this: next time an ad promises easy money, ask who's actually making money from it. Here's the lesson. People with a real edge don't sell it. They use it. Save this for the next time someone pitches you a course. What's the worst get-rich-quick pitch you've ever seen? I break down one lesson like this from a billionaire every day.
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Josh Brolin got sober at 19, after jail time. At 23, he went back to drinking. Then Anthony Hopkins told him why that's a gift. Brolin is Thanos. No Country for Old Men. Dune. He sat down with Theo Von, who's sober too, and they talked like two guys after a meeting. Here's what they said: 1. Brolin: "I did jail time. But then I stayed sober for three and a half years. Then I went back out." 2. Theo: "Did you ever have yourself as a resentment?" Brolin: "Of course. Probably the biggest one." 3. Theo: "Somebody said something in a meeting the other day... 'I'm unacceptable to myself.'" 4. Hopkins to Brolin: "Given no direction and no tools, we create more harm and hurt than most people. But given a few tools, we can have a bigger impact than most people." In the video below, listen for Brolin's two-word reaction when Hopkins tells him this. Try this: write down the trait people always called your problem. Then write what it could build if you pointed it somewhere. Here's the lesson. Your worst trait is just your engine without a steering wheel. What's the trait people used to call your problem? I post one lesson like this every day.
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Before his first hit, Timbaland's family lost their house. In 2025, he got a foreclosure notice on his own. Now he's suing his managers for $15 million He came from Virginia with nothing but a keyboard. Then came Aaliyah, Missy, Jay-Z and Justin Timberlake. Here's what he said in this interview: 1. "We had lost our house... I stayed in the grandma house." 2. "I was making so much producer money. Like NBA money." 3. "My accountant at one point said, 'Man, you don't spend no money.'" 4. "People like, 'You got to enjoy the fruit of your labor.' That's what f*cked me up." His lawsuit says his manager "stole millions." The mortgage and federal taxes went unpaid. His ex-manager denies it. He says Timbaland was already in debt in 2017. In the video below, listen for what his accountant told him, and what he did next. Try this: once a month, open every account and read every statement yourself. Even if someone else "handles it." Here's the lesson. You can hire someone to manage your money. You can't hire someone to care about it. Who's watching your money right now? I post one money story like this every day.
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Same app. Same eggs. Same minute. One shopper paid 23% more than the other. Theo Von's guest just explained why 馃憞 Lindsay Owens runs a consumer watchdog in Washington DC. Her team sent 400 secret shoppers into the Instacart app. Same store. Same 23 items. Same time. Here's what she told Theo: 1. "For 75% of the items in the cart, Instacart was charging different people different prices at the exact same time." 2. "You could be charged 23% more for a dozen eggs than me." 3. "They were just running experiments to see how much they could charge us for every item in the cart." 4. On a DoorDash patent: "Your phone battery was one of the variables." Instacart called it "typical A/B testing." After the backlash, they shut the AI pricing tool down. In the video below, listen for the moment she explains why a dying phone means a higher price. Try this: next time you're out with friends, everyone open Uber at the same time. Book from whoever gets the lowest price. Here's the lesson. It used to be one price for everyone. Now it's your price. Have you ever caught an app charging you more? I post one money story like this every day.
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26 years old. A YouTuber who wrote a horror script at his coffee shop job. He shot it for $750,000. It made $522 million. Then he reportedly turned down $2 million to change the ending. Curry Barker started out making horror shorts for YouTube. His first feature, he put online for free. His second, Obsession, sold at the Toronto film festival for $16.2 million. A24, Neon and Netflix wanted it too. It became the highest-grossing movie ever made for under $1 million. This Halloween, its main character was one of the most-searched costumes in America. Now A24 has him directing a new Texas Chainsaw Massacre. What he says got him there: 1. Make the idea that won't leave you alone. "I have ideas all the time and I write them in my notes. But when you have an idea that you just can't stop thinking about, that's when you should make it." 2. Read the comments. "YouTube taught me through the comments that people are really smart." 3. Keep it small. His budget: "seven hundred and fifty thousand, max." 4. Don't sell the part that makes it yours. He reportedly passed on $2 million to make the villain a hero. In the video below, he explains the idea behind the movie. Listen for what he says you have to earn. Try this: pick the one idea you keep coming back to, and put a rough version in front of people this month. Here's the lesson. You don't need permission anymore. You need proof people want it. Would you have taken the $2 million? I post one money story like this every day.
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Jay-Z will headline the Super Bowl for about $1,000 a day. He's worth $2.8 billion. His money advice is the opposite of what rappers post online. The NFL pays halftime acts union scale. His company Roc Nation co-produces the show, and fans are furious he picked himself. He's done this before. When he helped bring the Nets to Brooklyn, he says he took "the smallest piece." What he says about money: 1. Don't flex it. "That can't be our goal to get money and then show it on the internet." 2. Build your own thing. "Nike had to start somewhere." 3. Stop giving your value away. "We are culture. Nothing moves without us. We just continue to give it away." 4. Move on your timeline. "No matter what, don't let anyone rush your process." 5. Don't chase fame. "Fame comes and goes." In the video below, from 2017, he explains why he barely took money for the Nets. Listen for what he says about people who call him "all about money." Try this: next time you get paid, put a piece into something you own before you spend on something you show. Here's the lesson. A paycheck pays for your time once. Ownership keeps paying. What would you do for almost nothing if it built something you own? I post one money story like this every day.
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Jimmy Carr didn't drink for his first 12 years in comedy. His reason, told to Joe Rogan this week: "Alcohol is borrowing happiness from tomorrow." He found comedy in his mid-20s and went all in. Anything that could derail him had to go. His rules for getting anything done: 1. Ask one question every day. "What could I do today that I would be super happy I did tomorrow?" 2. Treat it as "giving a gift to your future self." 3. Think in days, not decades. "Whether it's with regret or nostalgia depends what you do today." The whole life is "too big to think about," he says. "But I could think about tomorrow." 4. Make it small. "If I write some jokes today and I test them tonight, I'll be so pleased I did that tomorrow." 5. And if you want to make money from what you love: "Just do it. Don't worry about making money. If you get good, then maybe." The 10,000 hours still apply. In the video below, he explains it to Rogan. Listen for what Rogan says you need if you want to get anything done. Try this: tonight, ask yourself what you could do today that you'd be glad you did tomorrow. Here's the lesson. Every good day is a gift you give tomorrow. Save this for the next time you're about to borrow from tomorrow. What's one thing you could do today that future you would thank you for? I break down one lesson like this from someone at the top, every day.
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2000: Mark Cuban buys the Mavericks for $285 million. 2023: He sells control and keeps 27%. 2025: The new bosses trade Luka Don膷i膰. Nobody asks him. In 2020 he joked he'd pick Luka over his wife. Today he told Steven Bartlett why he sold: the NBA "went from being about basketball to being about valuations." Reports valued the sale at $3.5 billion. His 27% alone is still worth roughly $945 million. In the video below, listen for the price he confirms at the end. Billions in his pocket, Luka in Los Angeles. Worth it?
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1979: Nike offers Magic Johnson stock. He takes Converse's cash. 1984: Nike signs Michael Jordan. Now: Nike pays Jordan nearly $300 million a year. Magic was 19 and had just beaten Larry Bird for the national title. Converse, Adidas and Nike all came to him. "Converse offered me the most money." Then Phil Knight came in himself: "I can't offer you the same type of money. But I can offer you stock." "I didn't even know what stocks was at that time. So, I passed on the stocks." His family "didn't come from money," he says. Five years later Nike signed a rookie from North Carolina. A reported $2.5 million over five years, plus a cut of every shoe with his name on it. Forbes now puts Jordan at $4.7 billion. Magic became a billionaire too, just not from shoes. In the video below, Magic tells Matt Barnes and Stephen Jackson about that meeting with Knight. Listen for what he says the stock would be worth today. The case for Magic: he was a 19-year-old who never had money, and he took the sure thing. The case for Jordan: he bet on a piece of something that didn't exist yet. Do the math. Nearly $300 million a year is about $820,000 a day, from one shoe deal. Here's the lesson. Cash pays you once. A piece of the company keeps paying. Cash or stock: which one would you have taken at 19?
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May: Floyd Mayweather sues his former business manager over $175 million. September: He drops the case. This week: He says $550 million was stolen from him. He said it on the PBD Podcast and wouldn't say the names on air. One of them, he says, "was sitting next to me acting like he was a friend." That one took $200 million, he says. The other $350 million was Showtime money sent "to someone else account." He's suing Showtime for at least $340 million, saying it helped his former manager Al Haymon move his earnings. Haymon isn't a defendant. Showtime denies it. The manager he sued in May, Jona Rechnitz, pledged about $100 million of his jewelry for roughly $13 million in financing, the suit said. Rechnitz denies everything: "It's sad that Floyd blew through his money." In the video below he tells Patrick Bet-David how the money went missing. Listen for how he says he's living now. The case for Floyd: he says the people running his business took it, and he's in court to get it back. The case for Rechnitz: Floyd dropped that suit, and his two lawsuits add up to about $515 million, not $550 million. Do the math. $100 million of jewelry for $13 million is 13 cents on the dollar. Here's the lesson, in Floyd's words: "Trust but verify." Was Floyd robbed, or did he blow through his money? Six more deals like his are in the article below.
Paul McCartney told Michael Jackson to buy songs. Jackson bought the Beatles'. John Fogerty got sued for copying his own song. Same team: Pippen made under $2.8 million, Jordan $33.1 million. Arnold took $0 for a movie. His biggest payday ever.
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Paul McCartney told Michael Jackson to buy songs. Jackson bought the Beatles'. John Fogerty got sued for copying his own song. Same team: Pippen made under $2.8 million, Jordan $33.1 million. Arnold took $0 for a movie. His biggest payday ever.
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Jay-Z's old partner Dame Dash once said "saving money is for suckers." Ten years later he filed for bankruptcy with $4,350 to his name. This month his life story sold at auction for over half a million dollars. He won't see any of it. Every dollar goes to the people he owes. His filing listed $25.3 million in debts. The buyer, Everlasting Films, gets his life story worldwide, 100 hours of video, photos, memorabilia and an unfinished documentary about him. The opening bid was $37,000. His biggest creditor, Josh Webber, won a $4 million defamation award against him. A judge is set to sign off on the sale on October 27. In the video below, from 2015, Dash tells The Breakfast Club hosts he's flipping all his money to get to a billion: "I'm not going to hold any money till I have a football team." Listen for who he says jobs are for. The case for Dame: he bet on himself. He says he and his partners put their own money into Roc-A-Fella, the label behind Jay-Z's and Kanye's early albums. The case for the hosts: they took the steady paycheck, and 11 years later The Breakfast Club is still on the air. Do the math. $25.3 million owed against $4,350 in assets. That's about $5,800 of debt for every dollar he had. Here's the lesson. Savings aren't for suckers. They're what keeps your name yours. Who won that argument: the man with no boss, or the hosts with a job?
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At a rally for Ohio Senate candidate Jon Husted, Trump told the crowd he "examined his ass." Then his shoulders, his feet, his hand, his jawline and his legs. "I don't do this with men very often. I started examining his body because I didn't know he was a great athlete." "I've never studied the body of a man before. But I looked at his ass." In the video below, listen for what he says Husted's ass is like. Seth Meyers had a question: "You maybe want to talk about gas or grocery prices, something people actually care about, or you just want us to vote based on the tightness of a candidate's ass?" Do the math. In this clip Trump says "ass" five times in about 30 seconds. Gas prices come up zero times. The case for Trump: it's a rally, and he was hyping a candidate's athletic build, not giving an economy speech. The case for Seth: the midterms are less than two weeks away, and people vote on what they pay at the pump. Rally riff or wasted pitch?
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Scottie Pippen won six titles next to Michael Jordan. By the last one, 121 NBA players were paid more than him. Jordan made $33.1 million that season. Pippen made less than $2.8 million. The reason was a contract he signed at 25. During the 1991 Finals, he agreed to $18 million, spread over eight seasons. One of 12 kids from a small Arkansas town, he didn't want one injury to wipe out the money. His agents reportedly told him not to. Even Bulls owner Jerry Reinsdorf reportedly warned it was too long. By 1998 he was sixth in pay on his own team. The Bulls refused to renegotiate. Nine days after Jordan retired in 1999, Pippen signed a five-year, $67 million deal with Houston. In his 2021 memoir, Pippen wrote that Jordan got $10 million for The Last Dance "while my teammates and I didn't earn a dime." "I was nothing more than a prop." In the video below, Patrick Bet-David quotes the text Jordan sent him during The Last Dance: "Hey Scotty, I heard you were upset." Listen for how Pippen sums up their last call. The case for Scottie: six rings next to Jordan, and by 1998 the 122nd-biggest paycheck in the league. The case for Jordan: he never set Pippen's salary. Pippen signed that deal himself and still earned about $109 million in his career, more than Jordan's $90 million. Do the math. Nike now pays Jordan nearly $300 million a year. That's almost three of Pippen's careers, every year. Here's the lesson. A long contract signed out of fear is a bet against yourself. Did Jordan owe Pippen anything, or did Pippen rob himself?
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LeBron made $52.6M last season. This season he makes $3.9M. By choice. Tomorrow he plays his first game for the 76ers. Philly had already paid Joel Embiid, Tyrese Maxey and Jaylen Brown, so all it could offer was the veteran minimum. HoopsHype calls it the biggest pay cut in NBA history. He's also the NBA's only billionaire player, worth about $1.7 billion per Sportico. On his podcast he explained why he signed anyway. "I think I'm more in love with the pursuit of, like, how much can I continue to defy the odds." Embiid, he says, has "a bunch of money" and "everything" except a ring. "I want to try to help him get that first one." Would you take a $48 million pay cut for one more ring? Clip below.
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$16B from scam and banned-goods ads. Suspected scammers paid Meta more to stay. Emmy-winning journalist Mariana van Zeller went through Meta's internal documents with Joe Rogan this week. By Meta's own estimate, that was 10% of its revenue, and users saw 15 billion "higher risk" scam ads a day. If Meta was less than 95% sure an advertiser was a fraud, the ads stayed up at a higher price. Inside Meta, that's a "penalty bid." Rogan's first reaction was "What?" The case for Meta: it told Reuters the documents "present a selective view" and called the estimate "rough and overly-inclusive." The case against: a penalty that pays Meta isn't a penalty. Bug or business model? Clip below.
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OpenAI's 3 months: +$1B revenue, +$3B costs. The man who called 2008 says America can't afford it to fail. That's Steve Eisman. Steve Carell played him in The Big Short. His breakdown has 4 million views. This week CoreWeave, which rents AI chips to OpenAI, saw its bonds hit 16% on $50 billion of debt. "Basically 50% of future revenue of Oracle is from a company that loses money like crazy." "Let's just imagine that OpenAI fails. Could happen. The whole United States of America would go into a recession overnight." Would you bet against OpenAI? Clip below.
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$4.4M budget. $163M box office. 5 Oscars. Paid for by Creedence Clearwater Revival. That's One Flew Over the Cuckoo's Nest. Michael Douglas told Joe Rogan this week how he got it made. His dad Kirk had tried for six years and was about to sell the rights. Michael found Saul Zaentz, a Berkeley jazz-label owner with one rock band. "So, Creedence Clearwater Revival paid for Cuckoo's Nest." The band's John Fogerty spent about 50 years fighting that same label to own his songs. He got them back in 2023. Did CCR get robbed? Clip below.
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Zuckerberg's Guinness face went viral this week. His $200 billion confession didn't. He says the face is "just my face." Fine. But in the same Cheeky Pint episode, he looks back at the end of last year, when Meta still hadn't even seen its new AI models: "We're going to write this check for like, I don't know, like $100 billion, $200 billion." "I'm like, Alex, are you sure this is going to work?" At a Hawaii offsite, Meta's CFO kept pulling Alexandr Wang aside: if it doesn't work, "it's going to be very, very bad in financial terms." Would you trust Zuck with $200 billion after the metaverse?
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Josh Brolin starred in a Best Picture winner that made $171 million. He took home about $30,000. The actor who later played Thanos told Theo Von he'd barely worked for years. At 30 he learned to trade stocks and did it full-time from home. "I was at home with one, two, three screens and four tabs per screen." "I made more money in those four years... than I had made in 20 years acting." Then came No Country for Old Men. "How much do you think I made from No Country?" Theo guessed $200,000. "That was a good guess. 100. So I cleared what? 30?" Would you have gone back to acting?
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