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The James Altucher Show

James Altucher
The James Altucher Show
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  • Jeff Pearlman on Tupac Shakur: The Myths, the Music, and the Man Behind the Legend
    A Note from JamesTupac Shakur—one of the greatest rap artists ever—was shot and killed almost two decades ago. What else is there left to say about him? What new things can be said?Well, Jeff Pearlman’s new book, Only God Can Judge Me: The Many Lives of Tupac Shakur, takes on that challenge. In our conversation, we talk about what Jeff uncovered in his research, why he wanted to write another Tupac book, and what made this one different.But first, a little story. Back in the ’90s, I was running a company that built websites. Around 1997 or ’98, Tupac’s mom wanted to release a new album of his music and build a website around it. I went in to pitch the project—$90,000, which would’ve covered payroll for another month. I needed that deal.So I show up, ready to impress. Tupac’s manager says, “Okay, here’s my computer. Show me what you’ve got.” And I realize—I’ve never used a Windows machine in my life. I’d only ever used Macs. I couldn’t even figure out how to turn it on.I had a computer science degree. I was a software engineer. I’d been running this company for years. But in that moment, I had to admit: “I don’t know how to use this machine.” He laughed me out of the room. Literally.That was the day I learned that even the smartest pitch can fall apart if you forget to check which operating system you’re using.Anyway—what else is there to talk about with Tupac Shakur? Jeff Pearlman and I figured it out.Episode DescriptionIn this episode, James sits down with bestselling author and journalist Jeff Pearlman (The Last Folk Hero, Showtime, Sweetness) to talk about his latest book, Only God Can Judge Me: The Many Lives of Tupac Shakur.Pearlman explores the contradictions, brilliance, and tragedy of Tupac’s life—how a performing arts kid from Baltimore became the poetic voice of West Coast hip hop, and how his complex identity was shaped by the Black Panther movement, celebrity culture, and the rise of gangsta rap.James and Jeff unpack Tupac’s evolution from Digital Underground hype man to solo artist, his influence on music and film, and the deeper meaning behind songs like Brenda’s Got a Baby. They also trace the events leading up to his death, separating myth from reality, and reflect on what Tupac’s legacy might have become if he’d lived.What You’ll LearnWhy Tupac’s “gangster” persona was more performance than realityHow his upbringing under a Black Panther mother shaped his worldviewThe untold story behind Brenda’s Got a Baby—and how Pearlman found the real “baby” years laterThe truth about Tupac’s relationship with Biggie Smalls and the events that led to both of their deathsWhy Tupac might have gone on to become a political or cultural leader, not just a rapperHow hip hop evolved from the storytelling of the ’90s to today’s more fragmented soundTimestamped Chapters[00:00] Introduction – James shares his connection to Tupac’s world [02:43] A Note from James – The web pitch that went wrong [05:00] Why Jeff Pearlman wrote a Tupac book [07:00] The challenge of writing outside his comfort zone [09:00] Tupac’s background and the myth of the “gangsta” image [11:00] The evolution of rap from the ’80s to now [16:00] What made Tupac’s art different from his peers [18:30] Tupac as a natural actor—and how he almost won an Oscar [21:00] Was his “gangster” side authentic or performance? [23:30] The night Tupac was killed—what really happened [26:00] How the East Coast–West Coast rivalry became fatal [30:00] The origin of Brenda’s Got a Baby and the real-life people behind it [35:00] Tupac’s literal storytelling and emotional honesty [36:30] How he might have evolved as an artist—or politician [38:00] The conversation that inspired a future Newark city councilman [40:00] Hip hop’s intelligence, legacy, and misunderstood brilliance [45:00] From Ice-T to Death Row: how labels, power, and politics shaped the scene [49:00] Wrapping up with gratitude—and a little hair envyAdditional ResourcesJeff Pearlman – Only God Can Judge Me: The Many Lives of Tupac ShakurJeff Pearlman’s Official WebsiteTupac Shakur – Brenda’s Got a Baby (Official Video)Digital Underground – Same Song (Tupac’s first verse)FBI Case File: Death of Tupac ShakurFilm: Juice (1992), starring Tupac Shakur and Omar EppsSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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  • Former FBI Agent, Eric O’Neill on Spies, Lies, and the Cyber Wars We’re Already Losing
    A Note from JamesOh my gosh—I was scared after this one. In this episode, I learned about what’s really on the dark web… and the even scarier stuff on what’s called the deep web.Eric O’Neill—who, by the way, is the former FBI agent who brought down Robert Hanssen, the biggest double agent in U.S. history—joined me for this conversation. Hanssen was the FBI’s top analyst on the Soviet Union, and at the same time, he was secretly working for the Soviet Union—for twenty-two years. Eric was the one who caught him. There was even a movie made about it—Breach (2007).Now Eric has written a book called Spies, Lies, and Cybercrime: Cybersecurity Tactics to Outsmart Hackers and Disarm Scammers. And honestly, it’s terrifying what’s out there right now—the dark web, the black markets, the cyberattacks, the scams that most of us have no idea are happening in the background of our digital lives.I’ll let Eric tell the stories.Episode DescriptionIn this episode, James talks with Eric O’Neill—former FBI counterintelligence operative and the man who captured the most notorious spy in U.S. history—about the unseen cyber battlefield shaping our world today. O’Neill explains how hackers, state actors, and scammers exploit human psychology far more than technology, and why every one of us is a potential target.From the lessons of his undercover work tracking Robert Hanssen to the rise of ransomware and AI-assisted phishing, O’Neill offers both a chilling reality check and a practical guide for staying safe in the digital age. He and James break down how modern espionage has moved online—and what ordinary people can do to protect themselves before it’s too late.What You’ll LearnHow Eric O’Neill captured Robert Hanssen, the most damaging spy in FBI historyWhy modern cybercrime depends more on human manipulation than hacking codeWhat really happens on the dark web and how it fuels global criminal networksHow AI is changing the speed and sophistication of digital attacksSimple but critical steps you can take right now to protect your data and identityTimestamped Chapters[00:00] Introduction — James sets the stage for a chilling conversation [02:15] Who is Eric O’Neill? The story behind capturing Robert Hanssen [07:45] The day Hanssen was caught — inside the FBI sting [13:10] From spycraft to cybercrime — how espionage went digital [17:30] The real difference between the dark web and the deep web [22:00] Why hackers target people, not systems [27:40] Social engineering and the psychology of manipulation [32:15] AI and the next generation of scams [37:55] How to recognize phishing and digital traps [44:20] Why cybersecurity starts with self-awareness [49:10] Lessons from the field — how espionage teaches us to think critically [54:05] The future of cyber warfare and personal protection [59:00] Final thoughts — the cost of complacencyAdditional ResourcesEric O’Neill – Spies, Lies, and Cybercrime: Cybersecurity Tactics to Outsmart Hackers and Disarm ScammersEric O’Neill – Gray Day: My Undercover Mission to Expose America’s First Cyber SpyFilm: Breach (2007) – starring Ryan Phillippe and Chris CooperFBI Official Case Summary – Robert Hanssen Espionage CaseEric O’Neill Official WebsiteSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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  • I Know that She Knows that I Know that She Knows: Steven Pinker on the Mysteries of Money, Power, and Everyday Life
    A Note from JamesI first got really impressed with Steven Pinker when he wrote The Better Angels of Our Nature: Why Violence Has Declined. He basically shows that over the past 10,000 years, every single century has been less violent than the one before it. You might think, “That can’t include the 20th century,” right? We had World War I, World War II, atomic bombs, the flu pandemic of 1920, Vietnam—all these massive wars. But when you look at violent deaths per capita, the 20th century was actually less violent than the 1800s, which were less violent than the 1700s, and so on. It’s a beautiful, data-driven argument for optimism.But it’s his latest book that really fascinated me: When Everyone Knows That Everyone Knows: Common Knowledge and the Mysteries of Money, Power, and Everyday Life. That subtitle alone—“common knowledge and the mysteries of money, power, and everyday life”—you can’t just skip past that. You have to know what it means.Take poker, for example. If someone bluffs you, you have to think: are they bluffing? Or are they making me think they’re bluffing, but they’re not? Or do they know that I think they’re bluffing, so now they’re actually not bluffing at all? That kind of circular reasoning—what philosophers call “common knowledge”—shows up in real life all the time.Like when you ask someone up for “a cup of coffee” after a date. You’re not really talking about coffee. But you’re also not saying what you actually mean. You’re hinting. You’re creating a safe, ambiguous space where both people know what’s being suggested without anyone having to say it outright. The same thing happens when you ask your boss, “Can we discuss taking on more responsibilities?” instead of saying “I want a raise.” We give partial information all the time, because being direct can change the relationship—or close off possibilities.Steven and I talked about why we communicate this way, how shared knowledge shapes everything from flirtation to power to money, and what happens when that balance breaks down.And by the way—if you’ve never seen Steven Pinker—he looks exactly like what you’d imagine a Harvard professor to look like. Long white hair, sharp blue eyes, and this kind of wild genius energy. Jay and I joked that he looks like Einstein meets Jimmy Page meets Beethoven. He’s the best-looking academic I’ve ever seen.Anyway, here’s our conversation on When Everyone Knows That Everyone Knows: Common Knowledge and the Mysteries of Money, Power, and Everyday Life, with my good friend Steven Pinker.Episode DescriptionIn this conversation, James and Steven Pinker explore how much of life runs on signals, innuendo, and the unsaid. Pinker explains how “common knowledge”—what everyone knows that everyone else knows—shapes everything from romantic attraction to political polarization to financial panics.They discuss why laughter matters, how game theory explains social awkwardness, and why being “brutally honest” all the time can destroy relationships. From Seinfeld to poker tables to the stock market, Pinker shows that our most human moments depend on the subtle art of leaving things unsaid.What You’ll LearnWhy subtle hints and shared assumptions keep relationships, negotiations, and societies stableHow laughter creates “common knowledge” and strengthens social bondsThe role of game theory and “recursive thinking” in everything from dating to diplomacyWhy total honesty isn’t always a virtue—and how “rational hypocrisy” preserves relationshipsHow stock market behavior, toilet paper hoarding, and bank runs all reflect the same hidden logicTimestamped Chapters[00:00] Introduction – When everyone knows that everyone knows [03:00] A Note from James: Why Pinker’s optimism matters [08:00] The hidden rules of communication and “weasel words” [10:00] Why we hint, wink, and avoid blurting the truth [13:00] “I love you” and the creation of common knowledge [16:00] How humor and laughter level the playing field [20:00] Politics, laughter, and social signaling [27:00] Bluffing, poker, and recursive thinking [31:00] Negotiation, honesty, and the limits of directness [38:00] Rational hypocrisy vs. radical honesty [42:00] Stock markets, speculation, and public knowledge [47:00] The toilet paper paradox: when panic becomes reality [56:00] Why intimacy can’t be legislated [01:00:00] Trade-offs, awareness, and flexible social norms [01:01:00] The “Sagan Curse” and being a public intellectual [01:04:00] The logic behind life’s unspoken rulesAdditional ResourcesSteven Pinker – When Everyone Knows That Everyone Knows: Common Knowledge and the Mysteries of Money, Power, and Everyday LifeSteven Pinker – The Better Angels of Our Nature: Why Violence Has DeclinedSteven Pinker – Rationality: What It Is, Why It Seems Scarce, Why It MattersSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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  • Obsession, Secrets, and Sleight of Hand: Inside the Hidden World of Modern Magicians with Ian Frisch
    A Note from JamesI’ve always loved books where a journalist gets so deep into a subculture that they become part of it. Magic Is Dead by Ian Frisch is one of those. He starts out covering a secret society of magicians—“The 52,” named for the cards in a deck—and ends up becoming one of them.It reminded me of other favorites like Word Freak (Scrabble), The Game (pickup artists), and Moonwalking with Einstein (memory champions). I love that genre of participation—when curiosity turns into obsession and then into mastery.Ian’s journey pulled me right in. He didn’t just report on the world of magicians; he lived in it, practiced card tricks until his hands hurt, and learned how obsession, storytelling, and performance shape every great craft. Talking to him made me think about how every one of us could benefit from being part of more than one “world”—to have different lives, different subcultures where we’re known and respected for something unique. That’s real diversification. Not just financial, but personal.Episode DescriptionIn this episode, James talks with journalist and author Ian Frisch about his book Magic Is Dead: My Journey into the World’s Most Secretive Society of Magicians and what it means to go all-in on obsession.They explore the underground network of modern magicians reinventing the art for the social-media age—tattoos, streetwear, viral videos, and all—and what these creative subcultures can teach the rest of us about mastery, storytelling, and risk.It’s a conversation about transformation: how curiosity becomes discipline, and how the principles behind sleight of hand apply to persuasion, business, and everyday life.What You’ll LearnWhy obsession—not balance—is often the key to getting great at somethingHow social media reshaped the art and culture of modern magicThe real psychology behind deception, storytelling, and human connectionHow magicians build trust with skeptical audiences (and what leaders can learn from it)Why belonging to multiple “worlds” or subcultures creates resilience and happinessTimestamped Chapters[00:00] Introduction — Obsession as a superpower [03:00] A Note from James — The journalist who became a magician [06:00] Participatory journalism and the power of total immersion [10:00] What makes this genre work: transformation and obsession [11:30] Discovering the new generation of social-media magicians [14:00] From top hats to tattoos: how magic reinvented itself online [18:30] The challenge of trust when magic meets video editing [20:30] The return of live magic and the human reaction [23:30] Subcultures, hierarchies, and belonging [26:00] Magic as a social tool for outsiders [29:00] How magicians train for a decade to master their craft [37:00] Ian’s own training: learning sleight of hand as an adult [40:00] The poker connection and card control secrets [44:00] Why mystery matters more than the trick itself [47:00] Storytelling, psychology, and reading people [52:00] Applying magician skills to real-world persuasion [54:00] Comedy, showmanship, and performance overlap [55:30] The secret societies of magic and “The 52” [58:30] Competition, creativity, and the economics of exclusivity [01:00:40] How Ian earned his place as the “Two of Clubs” [01:03:00] Inventing a new trick and becoming part of the storyAdditional ResourcesMagic Is Dead: My Journey into the World’s Most Secretive Society of Magicians by Ian FrischIan Frisch's WebsiteRelated titles discussed:Word Freak by Stefan FatsisMoonwalking with Einstein by Joshua FoerThe Game by Neil StraussThe Biggest Bluff by Maria KonnikovaMentioned magicians:Chris RamsayDaniel MadisonLaura LondonDoug McKenzieSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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  • Morgan Housel on The Art of Spending Money and Why Independence Is the Real Luxury
    A Note from JamesI’m such a fan of this guy. I loved The Psychology of Money — it felt like he was writing directly about me. I’ve made a lot of money, lost it all, made it again, lost it again. Over and over. And Morgan gets it.His new book, The Art of Spending Money, hits even deeper. It’s not just about being rich; it’s about freedom, simplicity, and contentment — the real returns of life. Every word of this conversation is a reminder that money is never about money. It’s about independence.Episode DescriptionIn this episode, James sits down with bestselling author Morgan Housel (The Psychology of Money, Same as Ever, The Art of Spending Money) to explore how wealth, happiness, and identity intersect.They talk about why most people spend money to impress strangers who aren’t even paying attention, why saving isn’t “delayed gratification,” and why independence is the ultimate luxury.Housel and Altucher go beyond finance — into psychology, meaning, and what happens when your identity gets tied up in your success. This is one of the most personal and useful conversations you’ll hear about money this year.What You’ll LearnWhy the goal of money isn’t happiness — it’s contentment.How to “purchase independence” instead of possessions.The hidden trap of social signaling and lifestyle inflation.How to build a healthy “psychology of money” that lasts through boom and bust.Why compounding memories might be more valuable than compounding interest.Timestamped Chapters[02:00] “Saving is purchasing independence.”[02:29] Happiness vs. contentment — why wealth brings fewer bad days, not more good ones.[03:00] A Note from James: how Morgan’s books mirror his own financial rollercoaster.[04:01] The social trap of spending for admiration.[05:19] Why signaling is universal — and why we overestimate who’s watching.[06:29] The three skills of money: making, keeping, and growing it.[07:02] Saving as joy, not sacrifice: how independence is pleasure in the present.[09:08] Why wealth means fewer bad days, not more good ones.[10:00] The quest for the simple life — why simplicity equals freedom.[11:04] James’s minimalist experiment: life with one backpack.[12:00] The billionaire’s regret — Harvey Firestone and the mansion paradox.[14:15] The psychology of downgrades and why people can’t go back.[15:40] Who are you trying to impress? The six people who actually matter.[17:21] Money as a tool vs. money as a scoreboard.[18:35] Why the desire for status falls when you find meaning elsewhere.[21:30] The fear of losing freedom — and how it drives bad decisions.[23:00] Even billionaires worry about losing it all — why fear never goes away.[25:11] Are we wired to worry about money? Nature vs. nurture in financial behavior.[27:39] Envy as outsourced thinking — how jealousy hijacks your decisions.[30:00] The five-minute rule: happiness never lasts, contentment does.[32:00] Saving in your 20s — when it matters and when it doesn’t.[33:51] The habits that stick: why early saving teaches independence.[35:29] Why the best memories come when you have the least money.[37:07] Scarcity, gratitude, and why effort creates value.[38:35] Wiping the slate clean: how to escape identity traps.[40:00] Retirement, identity loss, and why former athletes struggle.[42:25] “Keep your identity small.” — lessons from Paul Graham and Tim Ferriss.[45:00] When obsession fuels creation — how James moves between identities.[49:22] Sticking with one thing vs. exploring many — the range paradox.[51:25] The barbell of wisdom: compounding stability vs. compounding experiences.[53:27] The compounding of memories — why they may outlast wealth.[55:15] Simplicity, location, and the emotional geography of memory.Additional Resources📖 The Art of Spending Money by Morgan Housel📖 The Psychology of Money by Morgan Housel📖 Same as Ever by Morgan Housel📰 MorganHousel.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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About The James Altucher Show

James Altucher interviews the world's leading peak performers in every area of life. But instead of giving you the typical success story, James digs deeper to find the "Choose Yourself" story - these are the moments we relate to... when someone rises up from personal struggle to reinvent themselves. The James Altucher Show brings you into the lives of peak-performers: billionaires, best-selling authors, rappers, astronauts, athletes, comedians, actors, and the world champions in every field, all who forged their own paths, found financial freedom and harnessed the power to create more meaningful and fulfilling lives.
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