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
• How to Think Like a Roman Emperor by Donald Robertson
• The Obstacle Is the Way by Ryan Holiday
• "The Smoot-Hawley Tariff and the Great Depression" - The Economist
• Open to Debate

Our Sponsors:

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• Secure your online data TODAY by visiting ExpressVPN.com/ALTUCHER

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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

Sponsors:

• Visit “LandRoverUSA.com” to learn more about the Defender one-ten
• To get 6 bottles of wine for $39.99, head to NakedWines.com/JAMES and use code JAMES for both the CODE AND PASSWORD.
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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 cash
• How Gary made (and learned from) multiple startup failures in 2009
• Why content marketing is about sincerity, not SEO hacks
• How to test new business ideas through arbitrage—like flipping Jets gear on Amazon
• A 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, Products

Additional Resources:

• #AskGaryVee: One Entrepreneur's Take on Leadership, Social Media, and Self-Awareness (Amazon)
• Gary Vaynerchuk’s Twitter
• Wine Library TV Archives
• VaynerMedia
• DailyVee on YouTube

Our Sponsors:

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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 danger
• How James approaches relearning chess after a 27-year break
• What changes in the brain as we age—and how to work with it
• The surprising ways chess opens doors in life, business, and writing
• Why storytelling and vulnerability matter more than "success" alone

Timestamped 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 Journey

Additional 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 episode

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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 college
• What Michael Dell really thought during his showdown with Carl Icahn
• Why most big companies fail to innovate—and how to keep a startup mindset
• How Dell Technologies is preparing for the explosion in AI and edge computing
• What makes a good leader at the head of a $100 billion company

Timestamped 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 website
• Judge rejects Icahn's move on Dell buyout – CT Insider
• Richard Florida on the future of cities – Vital City NYC interview
• What is CRISPR? – Broad Institute
• History of MS‑DOS – Wikipedia

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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 lists
• How to turn your podcast (or other content) into a book—step by step
• The “Jesus Diet” method and how to combine timeless concepts with trending topics
• Why 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 angle
• The truth about book length—and why shorter can be better

Timestamps

00:00 Introduction and Excitement

00:17 Bonus Framework: The Podcast Technique

04:43 Framework 1: The 101 Technique

13:30 Framework 2: The Habits Technique

18:30 Framework 3: The Jesus Diet Technique

27:37 Framework 4: The Academic Research Technique

33:00 Conclusion and Encouragement

P.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.

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Episode Description:

James reconnects with entrepreneurs Michael and Kass Lazerow, whose journey spans selling Golf.com for $24 million, launching and pivoting Buddy Media into a $700 million Salesforce acquisition, and now investing in breakout brands like Liquid Death. This episode isn’t about startup clichés—it’s about emotional resilience, firing with kindness, how marriage can (barely) survive co-founding, and how to spot a trend before the world does.

They break down their “Go Gauge,” the six-part test they use before investing in a company. They talk about the trauma of being betrayed by family. And they reveal the surprisingly simple cheat codes they’ve used to keep building—and keep loving each other—across decades of risk. Whether you're building a business, looking for one good idea, or wondering what failure really feels like behind closed doors—this episode will give you a few new answers.

What You’ll Learn:

• Why transparency—not optimism—is a founder’s best crisis tool
• The six traits every idea needs to pass their “Go Gauge”
• How to fire someone with empathy and still tell them the truth
• What to do when your startup fails and the investors vanish
• Why the best startup strategy might be launching a pizza shop

Timestamped Chapters:

• [00:00] Bacon, milkshakes, and a first meeting
• [03:00] The Golf.com collapse and family betrayal
• [07:30] The psychology of failure and the will not to quit
• [12:00] Buddy Media’s pivot: from Facebook games to SaaS
• [15:00] Why failure sucks—but trends are your friend
• [21:00] Surviving marriage while surviving a startup
• [26:00] Emotional awareness, therapy, and not “shining the turd”
• [33:00] The $500M pizza truck startup fail
• [38:00] The truth about hiring, firing, and reorganizing
• [44:00] The death of venture capital—and rise of bootstrapping
• [50:00] Investing in pets, ice cream, and par-3 golf
• [54:00] Why Liquid Death is a billion-dollar brand
• [57:00] The Go Gauge: 6 filters for a fundable idea
• [01:02:00] Friendship, failure, and why they finally wrote the book

Additional Resources:

• 📘 Shoveling Sh*t: A Love Story About the Entrepreneur’s Messy Path to Success by Michael and Kass Lazerow
• 💧 Liquid Death – The canned water startup redefining beverage branding
• 🧾 Slice – Supporting independent pizza shops with tech
• 🐎 Commonwealth – Fractional ownership of racehorses and athletes
• 🍦 Van Leeuwen Ice Cream – The indie creamery with 70+ locations

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Notes from James:

Let’s be honest: most people who write a book never make money from it. Why? Because they stop at the last page. I want you to go further. In this episode, I show you how I turned my books into speaking gigs, consulting work, investment deals, and more. You don’t need a big publisher or a massive budget—just the right strategy.

Episode Descriptions:

In Part 4 of my 30-day writing series, I tackle one of the biggest questions aspiring authors face: Should you self-publish or go the traditional route? I’ve done both—some of my books were published by big-name houses, others I put out myself. This episode breaks down the pros, cons, and misconceptions of each approach—and how to make the smartest decision for your goals.

You’ll also learn exactly what to do after the writing is done. I cover how to market your book, build buzz, land media, grow your audience, and ultimately make your book work for you—financially, professionally, and personally.

Whether you're writing your first book or your fifth, this episode lays out the modern publishing roadmap and how to turn your words into real-world results.

What You’ll Learn:

• The truth about traditional publishing—what it offers and what it takes away
• Why self-publishing can earn you more money and give you more control
• What agents, publishers, and bookstore placement actually mean today
• How bestseller lists really work (and why most are just marketing tools)
• Exactly how to market your book after it’s published: newsletters, podcasts, and more
• How to build momentum before your book even comes out

Timestamps

00:00 Traditional vs. Self-Publishing: The Debate Begins

00:41 The Evolution of Self-Publishing

01:10 Benefits of Traditional Publishing

03:17 Challenges with Traditional Publishing

06:58 The Power of Self-Publishing

15:09 Steps to Professionally Self-Publish

16:34 The Importance of Audiobooks

21:15 Marketing Your Book: An Overview

21:53 Building and Utilizing an Email List

24:48 Leveraging Online Platforms for Book Promotion

27:08 The Power of Podcasts and Public Speaking

32:31 Maximizing Social Media for Book Sales

38:47 Final Thoughts on Book Marketing

P.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.

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A Note from James:

Well, you can't get more information about tariffs and the economy than what I just got and you're about to listen to. Wilbur Ross, who was Secretary of Commerce under the first administration of Trump, just came on the podcast. I got to ask any question I wanted—about tariffs, the economy, everything.

Don't forget, in Trump’s first administration, we saw steel and aluminum tariffs, and there were all the same concerns—about the economy, inflation, political blowback. Wilbur Ross was right at the center of it. And now, he’s giving me the full picture on what’s happening today and where it’s all heading.

This is a guy who built entire industries, served in the Cabinet, and is worth billions. He’s also the author of Risks and Returns: Creating Success in Business and Life, which I highly recommend. He’s an economic and business inspiration. I learned a lot from this conversation—I’m sure you will too.

Please share this episode with anyone who wants to better understand what’s really going on with tariffs and the economy. Enjoy!

Episode Description:

James sits down with Wilbur Ross, former Secretary of Commerce and seasoned investor, for a candid and highly detailed discussion on tariffs, China, inflation, pharmaceutical policy, and the state of the U.S. economy. Ross offers a firsthand look at the economic strategies being proposed for a possible second Trump administration—explaining why blanket tariffs might make sense, what’s really going on with China and rare earths, and how executive power is being used to bypass bureaucratic gridlock.

Listeners will get a rare window into how economic policy is being formed, the political forces shaping it, and what it all means for growth, inflation, and American manufacturing.

What You’ll Learn:

• Why blanket tariffs are being reconsidered—and how they differ from past policies
• The strategic role of tariffs in foreign policy, especially with China
• How U.S. dependence on China for pharmaceuticals and rare earths is being challenged
• What role executive orders and emergency powers play in trade and healthcare reform
• The real economic trade-offs between inflation, recession, and reshoring production

Timestamped Chapters:

• [00:03] Complexity of Tariffs and China's Role
• [03:18] Trump's Tariff Strategy and Economic Impact
• [07:21] China's Influence on Global Supply Chains
• [16:13] Pharmaceutical Dependencies and Economic Policies
• [26:47] Impact of Tariffs on Inflation and Recession
• [45:18] Conclusion and Final Thoughts

Additional Resources:

• Wilbur Ross’s Book: Risks and Returns: Creating Success in Business and Life
• International Emergency Economic Powers Act (IEEPA): Legal summary on IEEPA
• Naked Wines (Podcast Sponsor): https://www.nakedwines.com/james

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

A Note from James:

So I’ve been podcasting for, gosh, 11 years—over 1500 episodes. And through that whole journey, PodcastOne always stood out to me. They recently went public, and today I’ve got Rob Ellin and Kit Gray joining me. What’s the future of podcasting? If you're thinking about starting a podcast—or wondering how to grow one you already have—this episode's for you. These guys helped shape the entire industry, and they're sharing what works now, what doesn't, and how creators and networks can stay ahead.

Episode Description:

James Altucher sits down with Kit Gray and Robert Ellin, the powerhouse duo behind PodcastOne, to explore where podcasting is headed next. From YouTube’s dominance to AI-driven analytics, they dissect the changing landscape of content creation, monetization, and brand-building. They also discuss PodcastOne’s public market journey and how creators can turn niche ideas into multi-platform empires. Whether you're a podcast listener, creator, or investor, this episode gives you a real look at how podcasting is evolving from bedroom hobby to billion-dollar business.

What You’ll Learn:

• Why YouTube has become the most important platform for podcasters
• How to build a podcast brand that lasts—and makes money
• Why Gen Z is reshaping the future of content creation
• The real metrics that drive podcast growth and advertiser interest
• How PodcastOne is planning to become a billion-dollar company

Timestamped Chapters:

• [00:00] Introduction: The Future of Podcasting
• [00:06] The Rise of YouTube in Podcasting
• [01:08] James Altucher’s Podcasting Journey
• [01:53] Interview with Rob Ellin and Kit Gray
• [02:13] Evolution and Challenges in Podcasting
• [02:49] The Impact of Video and Live Shows
• [05:36] The Importance of Audience Engagement
• [06:19] Diverse Podcast Formats and Their Success
• [07:35] Building Relationships and Networks
• [09:32] Monetizing and Expanding Podcast Content
• [22:05] The Role of Gen Z in Podcasting
• [25:10] Debating College and Entrepreneurship
• [25:43] The Evolution of Media and Content Creation
• [26:53] The Power of Celebrity Influence
• [27:55] Building and Branding in the Modern Era
• [31:03] The Impact of Podcast Advertising
• [34:07] The Future of Podcasting and AI
• [40:34] The Growth and Influence of PodcastOne
• [41:59] Podcasting During COVID and Beyond
• [45:13] PodcastOne’s Public Journey and Future Plans
• 
  

Additional Resources:

• PodcastOne – Official Site
• Northwest Registered Agent
• BetterHelp Online Therapy
• Land Rover Defender
• Entrepreneurs on Fire by John Lee Dumas

This episode is brought to you by BetterHelp. Give online therapy a try at betterhelp.com/james

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