A Note from James:

We kept recording because the conversation wasn’t done. Part 1 was about writing and honesty. Part 2? It’s about consequences—what happens when people believe their own hype, when we confuse being loud with being right, and when storytelling gets weaponized. Ryan Holiday has written about ego, stillness, and obstacles. But this part of the conversation gets at something deeper: what happens when power and narrative collide. And how do we live with integrity when the tools we use to create can just as easily be used to manipulate?



Episode Description:

In Part 2 of their conversation, James Altucher and Ryan Holiday explore the darker side of influence—how public figures lose their grounding, how movements become cults, and how audience validation can steer creators away from their original purpose.

They discuss RFK Jr., Jordan Peterson, and Tucker Carlson—not as political figures, but as case studies in how public personas evolve under the pressure of attention. Along the way, they wrestle with their own roles as communicators: when to speak, when to hold back, and what it really means to be useful in a world full of noise.



What You’ll Learn:

 * Why creators are vulnerable to audience capture
 * The line between healthy skepticism and conspiracy thinking
 * What separates honesty from manipulation in public discourse
 * Why power often comes at the expense of self-awareness
 * How James and Ryan each wrestle with responsibility as public thinkers



Timestamped Chapters:

 * [00:00] Continuation from Part 1
 * [01:00] How Personas Get Distorted Over Time
 * [02:00] The RFK Jr. Conundrum
 * [04:00] Audience Capture and Dopamine Loops
 * [06:00] When Truth Becomes Optional
 * [08:00] Jordan Peterson and the Burden of Symbolism
 * [10:00] Platform Power vs. Message Integrity
 * [11:00] What Happens When You Start Believing Your Own Brand
 * [12:00] The "Edge" as a Career Strategy
 * [13:00] The Slippery Slope from Insight to Grift
 * [15:00] Building a Philosophy Business
 * [16:00] How Stoicism Can Be Used or Abused
 * [17:00] Tucker Carlson, Outrage, and Narrative Control
 * [19:00] Being Useful vs. Being Loud
 * [21:00] When You’re More Known Than You Are Understood
 * [23:00] The Fear of Changing Your Mind
 * [24:00] When Silence is the Most Ethical Choice
 * [25:00] Creating in Public Without Losing Yourself
 * [27:00] The Most Powerful Words: “I Don’t Know”



Additional Resources:

 * Ryan Holiday’s website: ryanholiday.net [http://ryanholiday.net]
 * Ego Is the Enemy by Ryan Holiday: Amazon [https://www.amazon.com/Ego-Enemy-Ryan-Holiday/dp/1591847818]
 * James Altucher on Twitter: @jaltucher [https://twitter.com/jaltucher]
 * The Daily Stoic podcast: Daily Stoic [https://dailystoic.com/podcast/]



See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

 Stoicism with Ryan Holiday - Part 2

A Note from James:

Ryan Holiday is one of the few writers I consider a peer—not just because of the work he’s done, but because of the choices he's made along the way. We’ve both published a lot of books. We've both dealt with audiences, platforms, and the weight of having a “point of view” in a world that increasingly wants you to pick a side. This episode wasn’t meant to be a debate or an interview. It was just two people trying to make sense of the tension between creativity and truth, honesty and influence, and why sometimes the best thing you can say is nothing at all.



Episode Description:

In this candid and far-ranging conversation, James Altucher sits down with bestselling author Ryan Holiday to talk about the changing nature of creativity, writing, podcasting, and personal ethics in a polarized media landscape.

They discuss the illusion of having to weigh in on every issue, the danger of algorithmic thinking, and how to stay true to your voice without becoming a prisoner to your audience. Whether you're a writer, a creator, or just trying to think more clearly in chaotic times, this episode offers real insight into the forces shaping our thinking—and how to resist them.



What You’ll Learn:

 * Why sharing too early can kill creative momentum
 * How social media shifted from expression to algorithm worship
 * Why long-form podcasts might be bad for your brain
 * How writing differs from other art forms in its tension and permanence
 * The tradeoffs between artistic freedom, platform growth, and audience expectations



Timestamped Chapters:

 * [00:00] Writing Without Talking About It
 * [01:00] Why Book Ideas Need Time in the Dark
 * [02:00] Creative Compulsion vs. Discipline
 * [03:00] Stand-Up, Dopamine, and Daily Feedback
 * [05:00] Point of View in a Binary World
 * [06:00] Silence, Ethics, and Speaking Up
 * [07:00] Noise as a Form of Violence
 * [09:00] Political vs. Philosophical Disagreements
 * [10:00] Social Media’s Shift to Opinion Farming
 * [11:00] The Algorithm as Audience Puppet Master
 * [12:00] When the Audience Has You
 * [13:00] Podcasting’s Algorithm Problem
 * [14:00] Are Podcasts Dangerous?
 * [16:00] Podcasting vs. Books: Tension and Craft
 * [18:00] The Rise of the Longform Grifter
 * [20:00] RFK Jr., Bad Ideas, and No Fact Checks
 * [22:00] Why Audiobooks Outperform Podcasts
 * [23:00] Can the Medium Save Us?
 * [25:00] When Podcasts Work (And When They Don’t)
 * [27:00] Music and the Emotional Power of Simplicity
 * [29:00] Songs vs. Culture War Commentary
 * [30:00] Great Lyrics, Great Feelings
 * [32:00] Bono, Stoicism, and Making You Feel Seen
 * [34:00] The Parasocial Magic of Fame
 * [35:00] Acting, Politics, and Emotional Truth
 * [37:00] Writing as the Hardest Artform
 * [39:00] Why Great Writing Still Matters



Additional Resources:

 * Ryan Holiday’s website: ryanholiday.net [https://ryanholiday.net/]
 * The Daily Stoic by Ryan Holiday: Amazon [https://www.amazon.com/Daily-Stoic-Meditations-Perseverance-Wisdom/dp/0735211736]
 * James Altucher on Twitter: @jaltucher [https://twitter.com/jaltucher]
 * Ryan Holiday’s books on Amazon: Author Page [https://www.amazon.com/stores/author/B007LUHFH8/]
 * Olivia Rodrigo – “Drivers License” (YouTube): Watch here [https://www.youtube.com/watch?v=ZmDBbnmKpqQ]
 * Led Zeppelin lyrics and discograph

Stoicism with Ryan Holiday - Part 1

A Note from James:

When I first said that college was a scam, people thought I was joking—or worse. But I wasn’t. If you’re 18 and listening to this, don’t go to college. And if you’re a parent, don’t send your kid without doing the math. College doesn’t guarantee a better life anymore. In fact, it could cost you years of freedom, tens of thousands of dollars, and saddle you with debt you can’t escape. In this episode, Doug Hill and I talk about why the traditional path of “get a degree, get a job, live happily ever after” no longer holds up.



Episode Description:

In this second installment of the Crazy Finance series, James Altucher and Doug Hill challenge another major financial assumption: that college is necessary for success. James argues that skyrocketing tuition, guaranteed student loans, and outdated curricula make college a bad financial decision for most people. Doug, who sent four kids to college, shares his own experience and ultimately agrees—except in a few key professions.

From alternative education paths to trade school opportunities, this episode breaks down the economics and psychology behind one of the most expensive decisions families ever make.



What You’ll Learn:

 * Why student loan debt is structurally predatory and practically inescapable
 * How government-backed loans have inflated tuition for decades
 * Which professions still require college—and which don’t
 * Why trade schools and alternative education may offer better returns
 * How personal development can happen outside the college system



Timestamped Chapters:

 * [00:00] Don’t Go to College (Seriously)
 * [01:00] Why “Personal Finance” Advice Feels Generic
 * [02:00] College as a Scam, Explained
 * [03:00] When College Is Actually Worth It
 * [04:00] Do Doctors Really Need 8 Years of School?
 * [06:00] The Business Degree: What Did It Even Teach?
 * [07:00] Entrepreneurship vs. Education
 * [08:00] The Myth of Higher Earnings
 * [09:00] Remedial Programming After Grad School
 * [10:00] Why Tuition Keeps Rising
 * [11:00] Government Guarantees = No Risk for Colleges
 * [12:00] The Hidden Costs and Opportunity Costs
 * [13:00] Who Actually Benefits From College?
 * [14:00] Trade Schools and Skilled Labor
 * [15:00] Electricians, Mechanics, and the Real ROI
 * [16:00] Useless Courses, Forgotten Skills
 * [17:00] Dropping Out and Getting Ahead
 * [18:00] Sales Skills vs. College Classes
 * [19:00] AI and the Future of Professional Work
 * [20:00] Socialization: Real World vs. Campus
 * [21:00] Google Certificates and Online Education
 * [22:00] James Insults His Alma Mater (Again)
 * [23:00] Who Really Wins in the College System?



Additional Resources:

 * James Altucher on Twitter: @jaltucher [https://twitter.com/jaltucher]
 * James’s article archive on college: Altucher Confidential – Why College is a Scam [https://archive.jamesaltucher.com/blog/college-scam/]
 * Coursera Professional Certificates (Google, Meta, etc.): coursera.org [https://www.coursera.org]
 * Khan Academy (Free Education): khanacademy.org [https://www.khanacademy.org]
 * U.S. Department of Education – College Scorecard: collegescorecard.ed.gov [https://collegescorecard.ed.gov/]
 * Trade School Info & Averages: Trade-Schools.net [https://www.trade-schools.net]
 * Federal Reserve Rep

Crazy Finance: Episode 2 - Is College Still Worth It?

A Note from James:

Owning a home has been sold to us as the American dream. But what if it's actually a financial nightmare? In this episode, I talk with my friend Doug Hill about why I think buying a house is a bad idea—not just a little bad, but one of the worst investments you can make. Doug and I disagree on some points, and that's the fun part. This isn't about being contrarian for the sake of it. It's about questioning assumptions that most people never even stop to think about.



Episode Description:

In this premiere episode of the Crazy Finance series, James Altucher and Doug Hill take on one of the most sacred cows in personal finance: home ownership. James argues that buying a house isn’t the milestone of success it’s made out to be—it’s an expensive, illiquid, and overrated investment. Doug offers a counterpoint rooted in emotional and lifestyle value. Together, they break down the numbers, psychology, and cultural narratives that shape the decision to rent or buy.

If you’ve ever wondered whether you should buy a house—or regret that you did—this conversation challenges the conventional wisdom with real numbers and uncommon insight.



What You’ll Learn:

 * Why owning a home may be one of the least financially sound decisions you can make
 * How homeownership locks you into inflexible geography and limits job mobility
 * The hidden costs of maintenance, property taxes, and lost opportunity
 * Why emotional security often drives people to buy homes, not financial logic
 * How rental life can be financially and psychologically freeing



Timestamped Chapters:

 * [00:00] Homeownership Is a Scam?
 * [01:00] Introducing the Crazy Finance Series
 * [02:00] James’s 11-Item Airbnb Life
 * [03:00] Why Freedom Costs Less Than You Think
 * [04:00] The Myth of "Throwing Away" Rent
 * [06:00] What Makes a House a Bad Investment
 * [07:00] Real Estate vs. Diversified Assets
 * [08:00] The Illusion of Home Equity
 * [09:00] Historical Returns on Housing
 * [10:00] "Found Money" and Forced Savings
 * [11:00] When You Never Truly Own Your Home
 * [13:00] Renting vs. Buying: Lifestyle Tradeoffs
 * [14:00] James vs. Doug: Dominican Property Math
 * [16:00] Renting as Freedom, Not Failure
 * [17:00] The 40-Year Trap of the Down Payment
 * [18:00] Recession Horror Stories
 * [19:00] Emotions vs. Economics
 * [20:00] Getting Stuck (Just Like Factory Towns)
 * [21:00] Why James Still Owns a Home (Kind Of)
 * [22:00] Gender, Culture, and Nesting Instincts
 * [23:00] Listener Homework: Is It Really a Good Investment?



Additional Resources:

 * James Altucher on Twitter: @jaltucher [https://twitter.com/jaltucher]
 * U.S. Housing Returns Historical Data: Case-Shiller Home Price Index via FRED [https://fred.stlouisfed.org/series/CSUSHPISA]
 * Mortgage Interest Rates: Bankrate.com [https://www.bankrate.com/mortgages/mortgage-rates/]
 * U.S. Property Tax Statistics: Tax Foundation – Property Taxes by State [https://taxfoundation.org/data/all/state/property-taxes-by-state-county/]
 * Choose Yourself by James Altucher – Amazon [https://www.amazon.com/Choose-Yourself-James-Altucher/dp/1490313370]



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Crazy Finance: Episode 1 – Why Buying a House Might Be the Worst Financial Decision

A Note from James:

So Chef Curtis Duffy—he’s won Michelin Stars, a James Beard Award. He’s been on Netflix’s Iron Chef, was a judge on Top Chef season 21, and he’s even shown up in The Bear. He runs the Chicago restaurants Ever and Grace, and he wrote this incredible memoir called Fireproof: Memoir of a Chef.

I could list all the accolades, but what really got me was his story—it's one of the most intense and heartbreaking I’ve ever read. The kind of story that stops you in your tracks. We talk about all of it—the trauma he lived through, the discipline he built, and what it takes to truly be great at anything. If you're chasing excellence in any part of your life, this episode will hit hard.



Episode Description:

James sits down with acclaimed chef Curtis Duffy for a raw and powerful conversation that goes far beyond the kitchen. From the trauma of losing both parents in a murder-suicide to earning multiple Michelin stars, Duffy shares the personal and professional disciplines that shaped his life. This isn’t just a story about food—it’s about resilience, focus, and the high cost of mastery. Whether you're building a business, learning a craft, or rebuilding your life, Curtis’s story offers something rare: clarity on what it really takes.



What You’ll Learn:

 * The difference between discipline and motivation—and why only one sustains greatness.
 * How Curtis transformed personal tragedy into a lifelong drive for excellence.
 * What separates a 2-star Michelin restaurant from a 3-star—and why consistency matters more than you think.
 * Practical ways to develop expertise, even in everyday tasks (like boiling an egg).
 * The importance of emotional control and quiet leadership in high-pressure environments.



Timestamped Chapters:

 * [00:00] Intro: Why Curtis Duffy’s story matters
 * [01:45] Chef vs. metalhead: Black Sabbath and personal intensity
 * [04:50] The family tragedy that shaped everything
 * [10:30] Processing the unimaginable: police, negotiation, and aftermath
 * [13:00] What Curtis wishes he had heard from his mother
 * [15:45] Breaking the cycle of abuse
 * [19:00] Leadership in the kitchen: discipline, not yelling
 * [22:00] Hiring red flags and building the right team
 * [26:00] The value of obsession and sacrifice
 * [30:00] Curtis’s first spark of culinary creativity
 * [32:00] What makes great chefs great
 * [34:00] The science of boiling an egg—and why it matters
 * [36:30] Developing "chunks" of expertise over decades
 * [38:00] Talent vs. skill: what really wins
 * [41:00] The role of discipline and why most people stop short
 * [43:00] Going from chef to restaurateur and media personality
 * [47:30] The pressure of competition shows vs. real kitchens
 * [49:00] How to train consistency into a restaurant culture
 * [52:00] Where restaurants are headed next
 * [53:00] James gets BLT advice from a Michelin-starred chef
 * [56:00] What makes a perfect baguette—and why most are awful
 * [58:00] Final thoughts and how to connect with Curtis



Additional Resources:

 * 📖 Fireproof: Memoir of a Chef by Curtis Duffy [https://www.amazon.com/Fireproof-Memoir-Life-Curtis-Duffy/dp/1639511350]
 * 🍽️ Ever Restaurant – Chicago [https://www.ever-restaurant.com/]
 * 🍷 Grace (Curtis Duffy’s former restaurant) [https://en.wikipedia.org/wiki/Grace_(restaurant)]
 * 🥁 Charlie Benante – [https://en.wikipedia.org/wiki/Charlie_Benante]

Michelin Stars, Tragedy, and the Discipline to Be Great | Chef Curtis Duffy

A Note from James:

Miesha Tate—at first, I’ve got to admit, I didn’t know much about UFC or MMA. But Miesha was the World Bantamweight Champion, and she fought Ronda Rousey—probably the most famous female fighter in the sport. I watched one of their fights, and honestly, I don’t know how I’d survive even a quarter of a second.

But the conversation we had wasn’t what I expected. Miesha opened up about the mindset behind championship success, the weight of public expectations, and how depression can still hit even after you’ve reached the top. We talked about how personal growth sometimes means burning down everything and rebuilding. This wasn’t just about fighting—it was about resilience, reinvention, and figuring out what matters when the title belt doesn’t solve your problems.

It was raw, honest, and eye-opening. I look forward to talking with her again.



Episode Description:

What happens when you reach the top of your field—and it still doesn’t fix what’s broken inside?

Former UFC Bantamweight Champion Miesha Tate shares the brutal truth about chasing success, surviving toxic relationships, and rebuilding her life from rock bottom. In this candid conversation, Miesha and James explore the psychology of high performance, the danger of tying self-worth to achievement, and how to know when it's time to walk away—even from something you love.

She tells stories from her early wrestling days to her UFC career, opens up about depression, and explains why learning to fail—and rebuilding—might be the most important skill of all.



What You’ll Learn:

 * Why reaching your ultimate goal might make you feel worse, not better
 * The hidden costs of high achievement and fame
 * How to identify toxic environments and take back control
 * Why learning to “rebuild your metaphorical home” is essential to resilience
 * How Miesha used mindset—not just physical training—to fight through adversity



Timestamped Chapters:

 * [00:00] The Broken Nose That Started It All
 * [03:00] High School Wrestling with the Boys
 * [06:00] Early Lessons in Grit and Gender Barriers
 * [08:00] From Wrestling to MMA: Embracing the Unknown
 * [11:00] Chasing the Win, Fearing the Loss
 * [13:00] Building the Metaphorical Home
 * [17:00] Blood, Grit, and the First Amateur Fight
 * [21:00] Getting Knocked Out and Coming Back
 * [27:00] The Problem with Thinking Winning Will Save You
 * [34:00] Fighting Ronda Rousey: Lessons in Obsession
 * [39:00] Training for the Unexpected
 * [45:00] When Success Doesn’t Fix Anything
 * [50:00] Rock Bottom and a 10-Day Drive to Nowhere
 * [55:00] Rebuilding from Scratch
 * [59:00] Miesha’s Life Today: Mindset, Family, and Homesteading



Additional Resources:

 * Miesha Tate on Instagram [https://www.instagram.com/mieshatate/]
 * Miesha Tate’s Podcast: Built for Growth [https://mieshatate.com/built-for-growth/]
 * UFC Fighter Profile: Miesha Tate [https://www.ufc.com/athlete/miesha-tate]
 * “The Weight of Gold” HBO Documentary [https://tv.apple.com/us/movie/the-weight-of-gold/umc.cmc.1w1mf7oz0hvtbkuupfsw6yt5u]



Our Sponsors:

 * Elevate your workspace with UPLIFT Desk. Go to https://upliftdesk.com/james for a special offer exclusive to our audience.

See Privacy Policy at https:/ [https://art19.com/privacy]

How UFC Champion Miesha Tate Overcame Rock Bottom with a Resilient Mindset

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 Legacy



Additional Resources:

 * 📖 Class Clown: Memoirs of a Professional Wiseass by Dave Barry [https://www.amazon.com/Class-Clown-Memoirs-Professional-Wiseass/dp/1668021781]
 * 📖 The Kite Runner by Khaled Hosseini [https://www.amazon.com/Kite-Runner-Khaled-Hosseini/dp/159463193X]
 * 🎤 Nate Bargatze Official Website [https://natebargatze.com/]
 * 🎤 Jim Gaffigan Official Website [https://jimgaffigan.com/]
 * 🎤 Hunter S. Thompson’s Fear and Loathing on the Campaign Trail ’72 [https://www.amazon.com/Fear-Loathing-Campaign-Trail-72/dp/0446698229]
 * 🎤 P.J. O'Rourke’s Official Website [https://www.pjorourke.com/] (archived)



The Secret of Dave Barry’s Humor: Class Clown Memoir and Florida Tales

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 cult
 * The complicated relationship between talent, trauma, and identity
 * How being taken from his family at age 12 shaped his worldview
 * How Chess.com exploded from 100k subscribers to millions after The Queen’s Gambit
 * Why cheating in chess is a growing threat—and how they’re fighting it
 * What the Hans Niemann scandal revealed about the future of the game
 * How to build resilience and purpose from even the darkest beginnings



Timestamps:

00:00 Introduction: A Unique Upbringing and Chess Obsession

00:43 The James Altucher Show: Welcoming Danny Wrench

00:58 Danny Wrench's Journey: From Chess Prodigy to Business Success

03:19 The Dark Side of Chess: Cult Life and Personal Struggles

12:38 Chess.com: Growth and Success

14:34 The Impact of COVID-19 and The Queen's Gambit

20:30 Cheating Scandals and Controversies in Chess

26:26 Future of Chess: Technology and Cheating

31:14 Conclusion: Living the Dream



Our Sponsors:

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How Chess Saved Danny Rensch’s Life: From Cult Roots to Chess.com’s Success

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 Thoughts



Additional Resources:

 * The Stoic Capitalist by Robert Rosenkranz [https://www.amazon.com/Stoic-Capitalist-Advice-Exceptionally-Ambitious/dp/1399423231/]
 * How to Think Like a Roman Emperor by Donald Robertson [https://www.amazon.com/How-Think-Like-Roman-Emperor/dp/1250196620]
 * The Obstacle Is the Way by Ryan Holiday [https://www.amazon.com/Obstacle-Way-Timeless-Turning-Triumph/dp/1591846358]
 * "The Smoot-Hawley Tariff and the Great Depression" - The Economist [https://www.economist.com/economics-brief/2018/09/27/how-the-smoot-hawley-tariff-made-the-great-depression-worse]
 * Open to Debate [https://opentodebate.org/]



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The Stoic Capitalist: How Rational Thinking Creates Success | Robert Rosenkranz

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 it
 * Why 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 up
 * What to do when your best effort still leads to loss
 * How to retrain your mindset after failure or self-doubt
 * Why reinvention is a lifelong skill, not a one-time fix



Timestamps:

00:00 The Relentless Nature of Chess

00:39 Meeting My Hero: Viswanathan Anand

01:12 A Personal Story of Inspiration

02:55 Interview with Viswanathan Anand

06:43 The Evolution of Chess and Personal Growth

28:57 The Role of Youth and Confidence in Chess

31:14 Concluding Thoughts and Future Prospects



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How to Master Anything—at Any Age: Lessons from World Chess Champion Viswanathan Anand

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.

Jay Yow

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