813 - How to be a Super Connector with Jen Gottlieb & Chris Winfield

A Note from James:One of the funniest guys I’ve ever spoken to—Dave Barry. I always love talking to him. He’s been America’s top humorist since the early ’80s with a syndicated column in 500 newspapers and a long list of bestselling books. This is his third time on the podcast, and his latest book, Class Clown: Memoirs of a Professional Wiseass, is out now.We get into everything—his process, his adventures, and his signature style of humor that’s made him a legend. It’s always fun with Dave.Episode Description:James sits down with Dave Barry to explore the surprising journey behind his new memoir, Class Clown. Dave shares how his humor evolved from playful everyman columns to a more personal, story-driven style. They talk about his outrageous adventures, from picking up his son in the Oscar Mayer Wienermobile to getting booed by telemarketers and dedicating a sewage station in his honor. They also break down the shifting landscape of writing, how syndication shaped Dave’s career, and why modern humor feels trapped in political silos.This is a rare chance to hear how one of America’s greatest humorists built a career by doing things to write about them—and why his readers became his closest allies.What You’ll Learn:Why Dave Barry was initially reluctant to write a memoir.How performing outrageous stunts became central to his writing.The critical role of reader engagement in building the success of his humor column.How the writing industry—and the path to building an audience—has radically changed.Dave’s candid perspective on modern political humor and why neutrality feels impossible today.Timestamped Chapters:[00:00] Introduction to Dave Barry[01:00] Writing a Memoir: The Journey Begins[02:00] The Humorist’s Approach: Balancing Persona and Reality[03:00] Adventures in Journalism: Creating Stories by Living Them[05:00] Tactical Humor: Rivalries, Stunts, and Getting Involved[08:00] When Humor Becomes the Story: Telemarketers and Public Reaction[12:00] Building a Community: How Dave Engaged His Readers[17:00] The Syndication Era: How Writing Used to Pay[23:00] The New Writing Economy: Substack and the Digital Shift[28:00] Assault Humor and the Loss of Neutral Comedy[31:00] What’s Next: Substack, Slowing Down, and Florida’s Wild Identity[35:00] Writing Novels vs. Columns: Dave’s Fast-Paced Storytelling Style[41:00] Stand-Up Comedy and the Influence of Nate Bargatze[44:00] Comedy Club Lessons: James on Bombing and Recovery[46:00] Criticism: Dave’s Approach to Bad Reviews[47:00] Farewell: Dave’s Thoughts on Humor, Writing, and LegacyAdditional Resources:📖 Class Clown: Memoirs of a Professional Wiseass by Dave Barry📖 The Kite Runner by Khaled Hosseini🎤 Nate Bargatze Official Website🎤 Jim Gaffigan Official Website🎤 Hunter S. Thompson’s Fear and Loathing on the Campaign Trail ’72🎤 P.J. O'Rourke’s Official Website (archived)See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

1 Jul 49min

Notes from James:I had no idea this conversation would go where it did. I thought we’d talk chess. Instead, we talked about life, trauma, manipulation, redemption… and how one of the world’s most popular games can be both a tormentor and a savior.Episode Description:In this raw and powerful episode, I sat down with Danny Rensch—International Master, Chief Chess Officer of Chess.com, and author of the upcoming memoir Dark Squares—to uncover a story that’s anything but a typical chess tale. Raised in a spiritual cult obsessed with chess, Danny’s path to mastery involved trauma, isolation, and resilience. We go deep into the psychological aftermath of cult life, the beauty and torment of the game that saved him, and how he helped turn Chess.com into a global phenomenon with over 200 million users.This isn’t just an episode about chess. It’s about survival, identity, and how to turn pain into purpose.What You’ll Learn:How Danny’s obsession with chess began inside a controlling cultThe complicated relationship between talent, trauma, and identityHow being taken from his family at age 12 shaped his worldviewHow Chess.com exploded from 100k subscribers to millions after The Queen’s GambitWhy cheating in chess is a growing threat—and how they’re fighting itWhat the Hans Niemann scandal revealed about the future of the gameHow to build resilience and purpose from even the darkest beginningsTimestamps:00:00 Introduction: A Unique Upbringing and Chess Obsession00:43 The James Altucher Show: Welcoming Danny Wrench00:58 Danny Wrench's Journey: From Chess Prodigy to Business Success03:19 The Dark Side of Chess: Cult Life and Personal Struggles12:38 Chess.com: Growth and Success14:34 The Impact of COVID-19 and The Queen's Gambit20:30 Cheating Scandals and Controversies in Chess26:26 Future of Chess: Technology and Cheating31:14 Conclusion: Living the DreamOur Sponsors:Pack up and go even further with the Defender 110. Learn more at LandRoverUSA.com/DefenderHead to rugiet.com/JAMES and use code JAMES to get 15% off today!Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHERSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

28 Jun 27min

A Note from James:Man, what a fascinating career Robert Rosenkranz has had—multi-billionaire, involved in virtually every part of finance and American industry. He wrote a book called The Stoic Capitalist, and what really stands out is how he's actively applied stoic principles to achieve immense success throughout his career. Even from a young age, stoicism played a crucial role, guiding him through critical business decisions. It's a real pleasure speaking with Robert—an American icon.Episode Description:James welcomes Robert Rosenkranz, author of The Stoic Capitalist: Advice for the Exceptionally Ambitious, to discuss how applying stoicism's timeless principles helped him navigate pivotal career decisions and financial challenges. Robert candidly shares his experiences—from early high-stress deals to launching a private equity firm where he risked his entire net worth—and explains why stoic philosophy remains essential for rational decision-making in business and life. The conversation highlights how embracing uncertainty and questioning assumptions can lead to clarity and resilience in a constantly changing world.What You'll Learn:How to differentiate between rational risks and emotional fears in critical decisions.Strategies for recognizing and overcoming cognitive distortions like catastrophizing.Practical applications of stoicism in modern investing and entrepreneurship.Insights into adapting to rapid technological changes, particularly AI.The importance of spousal support and personal relationships in career success.Timestamped Chapters:[00:00] Introduction to Robert Rosenkranz[02:00] The First Major Deal and Stoic Principles[05:00] Risk and Rational Decision Making[09:00] The Role of Biographies and Early Influences[12:00] The Importance of Spousal Support[28:00] Stoicism and Cognitive Behavioral Therapy[34:00] Exploring Financial Trends and Technology[35:00] The Impact of Artificial Intelligence[36:00] Addressing Fears and Job Displacement[37:00] Adapting to Technological Change[44:00] The State of the US Economy[48:00] Investment Strategies and Market Behavior[54:00] Stoicism and Its Influence on Investing[57:00] The Role of Social Media in Society[63:00] Reflections on Public Service and Education[67:00] Conclusion and Final ThoughtsAdditional Resources:The Stoic Capitalist by Robert RosenkranzHow to Think Like a Roman Emperor by Donald RobertsonThe Obstacle Is the Way by Ryan Holiday"The Smoot-Hawley Tariff and the Great Depression" - The EconomistOpen to DebateOur Sponsors:Pack up and go even further with the Defender 110. Learn more at LandRoverUSA.com/DefenderHead to rugiet.com/JAMES and use code JAMES to get 15% off today!Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHERSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

25 Jun 1h 3min

Notes from James:When I turned 40, I was depressed. I checked the top 50 chess players and saw only one person around my age: Viswanathan Anand. That moment gave me hope.Episode Description:I met one of my lifelong heroes—five-time World Chess Champion Viswanathan Anand—and got to sit down with him at the Norway Summit to unpack what it really takes to stay at the top… for four decades. We didn’t just talk about chess—we talked about life, legacy, improvement, and how to overcome self-doubt at any age.Vishy and I broke down how talent evolves, why confidence matters more than skill early on, and how he battled through plateaus, age, and even failure to remain among the world’s elite players—well into his 50s. This episode is a masterclass in longevity, performance, and reinvention.Whether you're into chess or not, Vishy's insights apply to anyone striving to master their craft, overcome obstacles, and stay in the game.What You’ll Learn:The real reason most people plateau—and how to push through itWhy youth is powered by “inaccurate self-confidence” (and why that’s not a bad thing)How to adapt when the game—or the world—changes faster than you can keep upWhat to do when your best effort still leads to lossHow to retrain your mindset after failure or self-doubtWhy reinvention is a lifelong skill, not a one-time fixTimestamps:00:00 The Relentless Nature of Chess00:39 Meeting My Hero: Viswanathan Anand01:12 A Personal Story of Inspiration02:55 Interview with Viswanathan Anand06:43 The Evolution of Chess and Personal Growth28:57 The Role of Youth and Confidence in Chess31:14 Concluding Thoughts and Future ProspectsSponsors:Visit “LandRoverUSA.com” to learn more about the Defender one-tenTo get 6 bottles of wine for $39.99, head to NakedWines.com/JAMES and use code JAMES for both the CODE AND PASSWORD.Elevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.Visit northwestregisteredagent.com/james and start building something amazing! Get more with Northwest Registered Agent at northwestregisteredagent.com/james.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

22 Jun 23min

A Note from James:So I’ve been doing this podcast for a long time—over 1500 episodes—and I’ve spoken to everyone from billionaires to best-selling authors, athletes to entrepreneurs. But there are a handful of episodes that still ring in my ears years later. One of them was Episode 156 with Gary Vaynerchuk.I was just re-listening to it while pulling together notes for a potential book, and I realized this conversation is timeless. It’s not about hype. It’s about freedom. Gary’s blueprint—learn, build, create community, stay self-aware—is the real deal. No shortcuts. No tricks. Just pure, actionable wisdom. Whether you’re 23 or 53, if you're serious about building the life you want, this one’s worth a listen.Send it to your kids. Your friends. Your future self.Thanks again for listening.Episode Description:In this re-release of one of the most downloaded episodes of The James Altucher Show, James sits down with Gary Vaynerchuk just before the release of his book #AskGaryVee. What unfolds is a candid, highly tactical conversation about business, content creation, self-awareness, and the true meaning of entrepreneurship.Gary breaks down his framework for success—from selling wine via YouTube in the early 2000s to launching VaynerMedia and investing in Facebook, Twitter, and Tumblr. He also explains why patience, practicality, and micro-failure are essential ingredients for long-term freedom.This isn’t motivational fluff. It’s the strategy, mindset, and playbook of someone who’s been in the trenches—and is still hungry.What You’ll Learn:Why "entrepreneurship" is really just a path to freedom—not fast cashHow Gary made (and learned from) multiple startup failures in 2009Why content marketing is about sincerity, not SEO hacksHow to test new business ideas through arbitrage—like flipping Jets gear on AmazonA tactical breakdown of self-awareness (and how to get it from people you trust)Timestamped Chapters:[00:00] Leisure vs. Freedom: What You’re Really Trading[01:00] Recommending Competitors as a Sales Tactic[03:00] Early YouTube, Wine Library, and ROI Before Social Was “Social”[06:00] Entrepreneurship vs. Lifestyle Marketing[08:00] Ego, Confidence, and What Scares Gary Vee[10:00] The Trainwreck Year: 2009 and Four Failed Startups[12:00] Experiments, Micro-Failures, and Million-Dollar Misses[14:00] Offense vs. Defense in Business[15:00] Building Trust Through Sincerity in Content[18:00] Self-Awareness: Gary’s Most Important Entrepreneurial Trait[22:00] The Real Numbers: What It Means to Be in the 1%[25:00] Leisure Costs More Than You Think[29:00] Why Gary Loves Losing and Chasing More Than Winning[34:00] The Self-Awareness Dinner Party Hack[38:00] Redefining Success: From $213K to $87K and Happy[42:00] Clouds and Dirt: Finding Your North Star and Executing in the Weeds[43:00] The Arbitrage Blueprint: eBay to Amazon[47:00] Community Building Through Twitter and Micro-Engagement[49:00] Jab, Jab, Jab, Right Hook (And What People Get Wrong About It)[52:00] Avoiding Negative Energy in Business and Relationships[54:00] Tactical Social Media Growth: Commenting, Listening, Engaging[56:00] Scaling Beyond Arbitrage: Events, Podcasts, ProductsAdditional Resources:#AskGaryVee: One Entrepreneur's Take on Leadership, Social Media, and Self-Awareness (Amazon)Gary Vaynerchuk’s TwitterWine Library TV ArchivesVaynerMediaDailyVee on YouTubeOur Sponsors:Pack up and go even further with the Defender 110. Learn more at LandRoverUSA.com/DefenderElevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audienceTo get 6 bottles of wine for $39.99, head to NakedWines.com/JAMES and use code JAMES for both the code AND PASSWORDDon’t wait, protect your privacy, build your brand and set up your business in just 10 clicks in 10 minutes! Visit northwestregisteredagent.com/james and start building something amazing!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

19 Jun 1h 1min

A Note from James:So the question is, I really feel that in order to get not good at something, but great at something, you have to be obsessed. You can't just wake up and decide to be obsessed—it has to be deep, almost irrational. Obsession is like addiction. It throws your life off balance, and yet... there’s this insane joy when you enter the subculture of your obsession and get better at it.I’ve seen this recently in crypto. I saw it in chess in Norway, commenting on what might’ve been the best chess tournament ever. And I felt it again when I sat down with Dirk Jan ten Geuzendam from New In Chess.We didn’t just talk about chess. We talked about obsession, aging, failing at something you love, and trying to find your place in a subculture that’s moved on without you.If you care about learning, obsession, or just love chess, you’re going to get something out of this episode. Dirk and I recorded this in Stavanger, Norway. I hope you love this conversation as much as I did being a part of it.Episode Description:What does it mean to return to your first love after nearly 30 years away? In this special crossover episode, James Altucher sits down with Dirk Jan ten Geuzendam, editor of New In Chess magazine, to reflect on his lifelong (and recently rekindled) obsession with chess. They explore how obsession shapes mastery, why wisdom sometimes trumps raw skill, and what it’s like to try and reclaim an old identity as an older version of yourself.James opens up about losing games to kids half his age, obsessively chasing improvement, and why it still might be okay to fail—as long as the journey is honest. From teenage blitz tournaments to dinner with Garry Kasparov, from neuroscience to narrative writing, this episode is as much about how to live as it is about how to play.What You’ll Learn:Why obsession is both a superpower and a dangerHow James approaches relearning chess after a 27-year breakWhat changes in the brain as we age—and how to work with itThe surprising ways chess opens doors in life, business, and writingWhy storytelling and vulnerability matter more than "success" aloneTimestamped Chapters:[00:00] The Power of Obsession[01:00] Travel Tales: Norway and Crypto[03:00] Chess Commentary and Podcasting with Dirk Jan[05:00] Dirk Jan's Intro on James Altucher[08:00] James' Curiosity and Love of Learning[10:00] Starting Chess at 17 and Becoming Addicted[13:00] Losing to Irena Krush and Facing Limits[17:00] Chess, Ego, and Real-World Consequences[22:00] How Chess Skills Apply to Business Problems[26:00] Writing as a Path Through Vulnerability[33:00] Returning to Chess: Memory, Aging, and Rediscovery[37:00] Eric Rosen, Coaches, and Mental Decline[41:00] Pattern Recognition vs. Calculation[47:00] What Makes Chess Players Unique[50:00] Interviewing Kasparov, Judit Polgar, Hikaru[56:00] Obsession and the Myth of Talent[58:00] Will the Book Get Written?[60:00] The James Altucher Invitational[62:00] Reflecting on the JourneyAdditional Resources:📘 New In Chess Magazine – The legendary publication covering elite and amateur chess alike🎙️ New In Chess Podcast – Hosted by Dirk Jan ten Geuzendam📚 Choose Yourself by James Altucher📺 Eric Rosen’s YouTube Channel – Where James first relearned modern chess💻 Chess.com – Popular online chess platform♟️ lichess.org – Free, open-source chess platform📘 Game Changer by Matthew Sadler & Natasha Regan – On AlphaZero’s influence on modern chess🧠 Andrew Huberman's Podcast – Neuroscience insights referenced in the episodeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

15 Jun 1h 2min

A Note from James:Michael Dell. Founder of Dell. I remember in college, hearing about this kid who was building computers in his dorm and making millions. I thought it was a myth. It wasn’t. He’s the real thing—and he just kept going.I wanted to understand what drove him, what it felt like to deal with Carl Icahn trying to wrestle his company from him, and what success feels like after decades of being in the game. Also: I had to ask why Dell didn’t invent Google. That, plus how he’s now thinking about AI, cancer, and what “focus” really means.Episode Description:James Altucher sits down with Michael Dell, founder and CEO of Dell Technologies, to trace the entire arc of Dell's career—from building computers in a college dorm room to defending his company against Carl Icahn and taking it private. In this candid conversation, Dell shares how early obsession with tech and business turned into a multibillion-dollar global enterprise, the lessons he’s learned about leadership, and how he’s positioning for the future with AI, cybersecurity, and gene tech on the horizon.This is more than a business story. It’s about risk, conviction, reinvention—and knowing when to walk away from Steve Jobs.What You’ll Learn:How Dell’s dorm-room business scaled to $80,000/month before he even left collegeWhat Michael Dell really thought during his showdown with Carl IcahnWhy most big companies fail to innovate—and how to keep a startup mindsetHow Dell Technologies is preparing for the explosion in AI and edge computingWhat makes a good leader at the head of a $100 billion companyTimestamped Chapters:[00:00] James introduces Michael Dell and the origin story of Dell Computers[01:00] The economics of building PCs in the early 1980s[03:00] Winning state bids with a bike and a dorm room[05:00] Pressure to become a doctor—and the 10-day “intervention”[10:00] Meeting Steve Jobs and licensing DOS from Bill Gates[13:00] Dell’s early B2B focus and international expansion[15:00] Going public and the Icahn showdown[18:00] How activist investors play poker with billion-dollar stakes[21:00] What focus really means in business[24:00] Defining leadership at global scale[26:00] Encouraging innovation inside massive companies[28:00] The failed Mac OS licensing deal[30:00] Philanthropy, education, and urban poverty[33:00] COVID lockdowns and a $100M response[35:00] The future of work and city migration[39:00] AI, edge computing, and exponential data[42:00] Gene editing, mRNA vaccines, and solving cancer[45:00] Blockchain in enterprise (no bitcoin on Dell’s balance sheet—yet)[47:00] Why cybersecurity is an arms race\Additional Resources:Play Nice But Win – Michael Dell’s memoir (Amazon)Dell Technologies – Official websiteJudge rejects Icahn's move on Dell buyout – CT InsiderRichard Florida on the future of cities – Vital City NYC interviewWhat is CRISPR? – Broad InstituteHistory of MS‑DOS – WikipediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

12 Jun 52min

Notes from James:Most people get stuck at the idea stage. That’s why I’m sharing frameworks—so you’re not staring at a blank screen. These techniques have helped hundreds of people (including me) go from idea to published book in just 30 days.Episode Descriptions:In Part 5 of my 30-day writing series, I unveil four of the most powerful book-writing frameworks I’ve ever used or taught—and they’ve helped hundreds of people write their first book in just a month. These aren’t theoretical. They’re real-world, repeatable methods that have led to bestsellers, media appearances, consulting gigs, and new careers.From the "101 List Technique" to the "Jesus Diet" method, each framework simplifies your creative process, helps you structure your ideas fast, and shows you how to turn your interests into income. I even share how you can write a book using past podcast interviews or unreadable academic research.If you’ve ever thought, “I have an idea, but I don’t know how to turn it into a book,” this episode gives you the blueprint—four times over.What You’ll Learn:The “101 List” format and why people LOVE books with listsHow to turn your podcast (or other content) into a book—step by stepThe “Jesus Diet” method and how to combine timeless concepts with trending topicsWhy academic research papers are gold mines (and how to use them to write your book)How to choose a niche, research efficiently, and find your book’s unique angleThe truth about book length—and why shorter can be betterTimestamps00:00 Introduction and Excitement00:17 Bonus Framework: The Podcast Technique04:43 Framework 1: The 101 Technique13:30 Framework 2: The Habits Technique18:30 Framework 3: The Jesus Diet Technique27:37 Framework 4: The Academic Research Technique33:00 Conclusion and EncouragementP.S. Want to go deeper? Check out my full course on Udemy or visit chooseyourselfacademy.com: How to Write and Publish a Book in 30 Days – available now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

5 Jun 33min