A Note from James

I’m really concerned about the level of discourse in this country. It’s almost a cliché to say that now, but especially after the Charlie Kirk assassination, the division feels overwhelming. I even got invited to speak at the Oxford Union—the most prestigious debate society in the world—but ultimately declined because I didn’t like how the whole situation was being handled.

I can’t stand when anyone celebrates a death. Regardless of politics, it disturbs me. And every day, my social media feed is filled with more division and hatred. So I wanted to talk with Charles Duhigg. He wrote Super Communicators (now out in paperback) about how to actually connect with people in a world that seems torn apart. Even in a short conversation, I learned so much from him—things that made me think in new ways.

Episode Description

Pulitzer Prize-winning journalist and bestselling author Charles Duhigg (Super Communicators, The Power of Habit) joins James to explore how we can talk to each other in an age of polarization. From tragic political violence to everyday disagreements with family and friends, Charles explains why humans are wired for connection, how to ask better questions, and what it takes to turn conflict into understanding.

This episode is a practical guide to becoming a better communicator—especially when the stakes are high.

What You’ll Learn

• The three types of conversations—emotional, practical, and social—and why mismatched conversations cause breakdowns.
• How to ask “deep questions” that uncover values and experiences, not just surface facts.
• Why mirroring, looping, and listening carefully make people feel truly heard.
• How to handle anger and cliches with curiosity instead of combat.
• Why disagreements don’t destroy democracy—bad communication does.

Timestamped Chapters

• [03:08] James on division, Oxford Union, and why he turned down an invitation
• [06:06] Why James brought Charles Duhigg on the podcast
• [07:00] Political violence, polarization, and clashing conversations
• [10:42] What made Charlie Kirk an effective communicator
• [12:21] Communication as connection, not just information
• [13:21] Do both sides have to want connection?
• [15:20] Congress, partisanship, and performative politics
• [19:36] How “deep questions” build trust and reveal values
• [21:10] James on why he podcasts—and Charles’s analysis
• [23:39] Social reciprocity and feeling closer through vulnerability
• [24:23] History shows the value of disagreement done right
• [26:00] Why we reward bad behavior—and how to stop
• [27:09] James on gun control neutrality and frustration
• [29:00] Parenting lessons applied to political disagreements
• [30:00] “When you’re furious, get curious”
• [31:53] Moving past cliches by asking about personal experiences
• [33:08] Admitting confidence levels in arguments
• [34:19] Is Charles optimistic about America’s communication future?
• [34:50] A challenge for listeners: ask someone you disagree with “why does this matter to you?”
• [36:09] Closing thoughts: Super Communicators now in paperback

Additional Resources

• 📖 Super Communicators by Charles Duhigg
• 📖 The Power of Habit by Charles Duhigg
• 🌐 Charles Duhigg’s website

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A Note from James

This is a crazy story. Martin Suarez holds the record for the longest continuous undercover assignment in FBI history. He went undercover as a cartel drug lord—smuggling billions of dollars’ worth of cocaine while posing as “Manny.” At one point, the story even starts with a gun to his head, convinced his cover was blown.

The book Inside the Cartel: A True Crime Tale of Espionage, Undercover Operations, and a War Against Billionaire Drug Lords—co-authored with journalist Ian Frisch—captures it all. Martin’s voice may be difficult to catch at times because he’s been battling ALS, but every word is worth hearing. Ian also joins to help tell the story. This conversation had me on the edge of my seat.

Episode Description

Former FBI agent Martin Suarez spent more than a decade living undercover inside Colombian cartels. Known to the underworld as “Manny,” he laundered money, smuggled cocaine, and survived assassination attempts—all while secretly working for the U.S. government.

In this episode, James sits down with Suarez and his co-author Ian Frisch to explore how an ordinary Navy veteran became the FBI’s ultimate undercover agent, why deception works in high-stakes negotiations, and what lessons from cartel infiltration apply to everyday life.

What You’ll Learn

• The psychological techniques Martin used to maintain his cover for years inside violent cartels.
• How undercover work creates “alternate realities” to control narratives and shift blame.
• Why confidence and self-belief are critical in negotiation, business, and personal life.
• The role of deception and patience in both undercover work and real-world persuasion.
• How Martin and his family managed the risks and sacrifices of a life lived undercover.

Timestamped Chapters

• [03:00] A gun to the head: the moment Martin thought his cover was blown
• [07:00] Surviving a cartel hitman
• [10:00] From Navy to FBI: the start of an undercover career
• [12:00] Why Martin was the “perfect” undercover agent
• [14:00] Smuggling versus intelligence gathering: the FBI’s strategy
• [16:00] How to move cartel shipments without breaking cover
• [18:00] The art of deflecting blame and creating alternate realities
• [22:00] Cartel power and control in Colombia
• [23:00] U.S. government ties and the Iran-Contra era
• [25:00] Using FBI agents as “girlfriends” to gather intelligence
• [27:00] Facing long-term risks—and the bigger battle with ALS
• [30:00] Marriage, trust, and sacrifice during undercover life
• [32:00] Art theft undercover operation in Europe
• [36:00] Fooling even the CIA with a perfect legend
• [41:00] How legends are built in the digital age
• [44:00] Negotiation, seduction, and cartel psychology
• [45:00] Ian’s lessons on confidence and self-convincing
• [47:00] Applying undercover strategies to everyday life
• [49:00] The role of greed in cartel decision-making
• [50:00] Marriage, grounding, and long-term support
• [51:00] Are cartel leaders truly evil—or just highly educated?
• 
  

Additional Resources

• 📖 Inside the Cartel by Martin Suarez and Ian Frisch
• ✍️ Ian Frisch’s journalism and other work

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Episode Description

Right after wrapping up their main conversation, James and Brian hit record again for a bonus session. What came out is an unfiltered talk on humility, arrogance, and the strange mix of traits needed to achieve great things. From the wisdom of the Talmud to the Dunning–Kruger effect, they explore why even Nobel Prize winners wrestle with imposter syndrome.

James shares how writing books requires a mix of blind confidence and humility, while Brian connects scientific resilience to obsession, quests, and flow states. The two also talk candidly about the challenges of writing and publishing science books in today’s world—and Brian previews his bold new project exploring Jim Simons, “Chern–Simons Theory,” and the very arrow of time itself.

What You’ll Learn

• Why success requires balancing humility with courage—and sometimes arrogance with ignorance
• How Nobel Prize winners secretly struggle with imposter syndrome
• Why writing books demands both blind confidence and ruthless editing
• The difference between obsession and quest when pursuing success
• What “Chern–Simons Theory” reveals about time, space, and the structure of the universe

Timestamped Chapters

• [02:00] Humility, chutzpah, and the Talmud’s two pockets
• [03:00] Writing, Dunning–Kruger, and the blindness needed for progress
• [05:00] Imposter syndrome—even after winning the Nobel Prize
• [06:00] Resilience, grad school, and the limits of Goggins-style toughness
• [07:00] Obsession vs. quest: two paths to achievement
• [08:00] Flow states, joy, and Nobel Prize winners at play
• [09:00] The cost of careers that don’t allow flow
• [10:00] The challenges of science publishing in the age of AI
• [11:00] James on downloads, inspiration, and writing talks in his sleep
• [12:00] The genius spirit, loneliness, and Hemingway’s advice
• [13:00] Why science books lean on unprovable ideas
• [14:00] String theory, quantum entanglement, and perennial sellers
• [15:00] Jim Simons, Chern–Simons Theory, and the arrow of time

Additional Resources

• Brian Keating – Official Website
• Into the Impossible: Focus Like a Nobel Prize Winner (Volume 2) – Amazon
• Donna Strickland – Nobel Prize in Physics 2018 – Nobel Prize Biography
• Cal Newport – Deep Work – Amazon
• Ali Abdaal – Feel Good Productivity – Amazon
• Ryan Holiday – Perennial Seller – Amazon
• Chern–Simons Theory (Mathematical Physics Overview) – Wikipedia
• Jim Simons Biography (The Man Who Solved the Market) – Amazon

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Episode Description

James sits down once again with cosmologist Brian Keating—longtime friend of the show and author of Into the Impossible: Focus Like a Nobel Prize Winner. In this candid conversation, they challenge each other’s views on focus, curiosity, and the trade-offs of staying in your lane. Brian shares behind-the-scenes lessons from interviewing Nobel Prize winners, the thinking behind his new “Keating Test” for AI, and why communication matters as much as discovery in science.

This episode isn’t about self-help clichés. It’s about real-world insights you won’t hear anywhere else—whether it’s why guarding your time is the most important skill, how to use flow states to sharpen your career, or why great breakthroughs depend on questioning the work of those who came before.

What You’ll Learn

• Why Brian created the “Keating Test” as a new measure for true artificial intelligence
• How Nobel Prize winners balance intense focus with curiosity across disciplines
• Why communication skills matter as much as scientific discovery for lasting impact
• How to guard your time from “time bandits” and apply the power of saying “no”
• Practical ways to find your lane—or combine lanes—while still pursuing flow and mastery

Timestamped Chapters

• [02:00] The Keating Test: AI, free will, and the act of survival
• [06:00] Humor, history, and reclaiming the “worst joke ever told”
• [08:00] Friendship, TEDx, and 11 years of conversations
• [09:00] Lessons from Nobel Prize winners: beyond self-help habits
• [10:00] Publishing with Scribe/Lioncrest and connections to James and David Goggins
• [12:00] Into the Impossible, Volume One: why distilling Nobel wisdom matters
• [13:00] Imposter syndrome, Alfred Nobel, and Volume Two’s focus
• [15:00] Donna Strickland, LASIK, and the power of saying no
• [18:00] Stay in your lane—or widen it? A debate on mastery and curiosity
• [23:00] Newton, Pascal, and the discipline of sitting in a room
• [26:00] Regrets, diversification, and finding flow
• [28:00] Crystallized vs. fluid intelligence in the age of AI
• [31:00] The importance of novelty—and the Lindy test
• [35:00] Math, reality, and the unreasonable effectiveness of ideas
• [38:00] Teaching quantum computing: bridging theory and life skills
• [43:00] From cryogenics to code: skills that outlast AI
• [47:00] Why communication defines success in science
• [50:00] Doing things that don’t scale: relationships, meteorites, and networks
• [52:00] The missed opportunities of office hours—and how to build relationships
• [54:00] Reading theses, genuine curiosity, and non-scalable networking
• [55:00] Into the Impossible, Volume Two: life lessons and scientific breakthroughs
• [57:00] How old is the universe? The cosmic controversy
• [59:00] Gravitational waves, BICEP2, and losing the Nobel Prize
• [61:00] Dust, data, and the Simons Observatory’s quest for origins
• [63:00] What comes next: Jim Simons’ legacy and Brian’s future book

Additional Resources

• Brian Keating – Official Website
• Into the Impossible: Focus Like a Nobel Prize Winner (Volume 2) – Amazon
• Into the Impossible: Think Like a Nobel Prize Winner (Volume 1) – Amazon
• Losing the Nobel Prize – Amazon
• David Goggins – Can’t Hurt Me – Amazon
• Steven Pressfield – The War of Art – Amazon
• Arthur Brooks – From Strength to Strength
• Jim Simons Biography (The Man Who Solved the Market) by Gregory Zuckerman – Amazon

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A Note from James

I’ve been on and off writing. From 2004 to 2021, I wrote one to two books a year, without fail. Since then, nothing. But I’ve been working on an idea: obsession. When I’m not obsessed, I can’t do much—sometimes not even the basics. But when I am obsessed, I can turn that energy into real outcomes: a business, a book, a skill, sometimes success, sometimes failure.

This episode comes from a recent conversation I had with the Ventura Labs team. We talked about obsession, but also about AI, crypto, and how those obsessions have led to building TAO Synergies ($TAOX), a public company on Nasdaq. I’d love to hear your thoughts: should I write this as a book? Reach out on Twitter or anywhere.

Episode Description

James Altucher joins the Ventura Labs Podcast to explore the link between obsession, creativity, and execution. From contributing to IBM’s Deep Blue in the 90s to co-founding TAO Synergies, James shares how obsessions with chess, AI, and crypto have shaped his life and career.

The conversation covers the philosophy behind decentralized AI, the rise of treasury strategies, and why writing down ten ideas a day can change everything. This episode isn’t about trends—it’s about frameworks: how to spot real opportunities, how to build around them, and how to know when obsession is worth pursuing.

What You’ll Learn

• Why obsession can be both a weakness and a superpower—and how to channel it productively.
• How Bittensor ($TAO) creates decentralized AI opportunities at a fraction of traditional costs.
• The mechanics of treasury companies and how TAO Synergies is building its playbook.
• The risks and rewards of subnet investing, and how tokenomics actually drive value.
• Lessons James learned from failure, from HBO web series experiments to company collapses, and why generating ideas daily can reset your career.

Timestamped Chapters

• 02:15 – Introduction
• 02:58 – What is Bittensor
• 06:24 – AI background and Deep Blue
• 09:34 – Chess interest and journey
• 11:46 – $TAOX inspirations and getting TAO-pilled
• 14:09 – TAO Synergies origin story
• 16:57 – Reaching 100M and playbook
• 19:41 – Treasury strategies and validators
• 22:02 – Launching TAO Daily
• 25:51 – Bitcoin adoption and involvement
• 29:32 – Subnet investing and analysis
• 30:59 – Token warnings and TAO demand
• 35:46 – Subnet proposals and increases
• 37:36 – Successful sectors and examples
• 40:04 – Yanez and Metanova
• 43:17 – Decentralization benefits
• 46:13 – AI jobs and countering fears
• 49:34 – Beneficial sectors: AI and stablecoins
• 53:59 – Bryan Johnson documentary
• 55:17 – Starting podcast and interviews
• 57:14 – Interests and obsessions
• 01:00:56 – Daily writing obsession and origins
• 01:03:47 – Confidence and opinions
• 01:07:33 – Company failures and lessons
• 01:10:42 – HBO series and 3AM show
• 01:14:26 – Hesitancy, regrets, pivotal points
• 01:17:38 – Advice on time and experiments

Additional Resources

• TAO Synergies: @TAOSynergies
• TAO Daily (community news hub): taodaily.io
• Naval Ravikant – AngelList founder and Bitcoin advocate
• Ventura Labs Podcast (YouTube): @VenturaLabsPodcast

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A Note from James

The man, the myth, the legend—Rick Harrison. You know him as the star of Pawn Stars, the reality show based on the Gold & Silver Pawn Shop in Las Vegas. The show has been running for over 21 seasons, and Rick himself has become the godfather of the pawn business.

I even joined Rick and Chumlee on their own podcast, Pawn After Dark, which was a blast. On this episode, Rick shares the ins and outs of the pawn world—why he thinks it’s the best business model ever, how it’s really the oldest form of banking, and why every object in his shop is more than just an item—it’s a story.

Episode Description

Rick Harrison didn’t just create one of the most successful reality shows of all time—he’s spent decades running the world’s most famous pawn shop. In this episode, Rick and James explore why pawn shops have been a cornerstone of finance for centuries, how collectibles get their value, and why storytelling is the real currency behind every object.

From Rolex watches to cowboy hats with mobster histories, Rick breaks down how he decides what’s valuable, how emotions shape the market, and why gold has remained the ultimate store of value for over 6,000 years.

What You’ll Learn

• Why the pawn business is “the oldest form of banking” and how it still thrives today.
• How items gain value not just from material, but from the stories attached to them.
• Why so many Americans rely on pawn shops over banks and payday lenders.
• The economics of Rolex watches, diamonds, and gold in the pawn industry.
• How Pawn Stars became a global hit and what keeps the show fresh after 750+ episodes.

Timestamped Chapters

• [01:00] A Note from James: introducing Rick Harrison
• [02:00] The legacy of Pawn Stars and 21 seasons on TV
• [04:15] Why Rick still loves his job after 750 episodes
• [05:30] Every object is a story: the cowboy hat with a mob connection
• [06:15] Pawn shops as the oldest form of banking
• [07:20] Why millions of Americans rely on pawn shops instead of banks
• [09:15] Rolexes, lawyers, and quiet transactions
• [10:30] How Rick values collectibles, art, and gold
• [11:45] Diamonds, divorces, and why jewelry stores buy from pawn shops
• [13:10] Charlie Chaplin’s pawn shop comedy and the stigma shift
• [14:00] Lab-grown diamonds, fakes, and what people really want
• [15:30] The emotions (and fights) inside pawn shops
• [17:10] Silverware, grandma’s heirlooms, and misplaced expectations
• [18:30] When sentiment meets market value
• [20:00] The most expensive items Rick has for sale
• [21:15] Civil War coins, rare history, and collectors’ obsessions
• [22:30] How U.S. money once carried fine art
• [23:00] Gold vs. silver: why gold endures as the ultimate store of value
• [24:15] The making of Pawn Stars and its runaway success
• [25:15] Why the show works: family-friendly, educational, and fun
• [26:00] Rick on Chumlee, drama, and why the show will keep going

Additional Resources

• Pawn Stars on History Channel – Pawn Stars Official Site
• Pawn After Dark (Rick’s podcast) – Pawn After Dark
• Gold & Silver Pawn Shop (Las Vegas) – gspawn.com
• Charlie Chaplin’s The Pawnshop

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A Note from James

I’m honored to have today’s guest: Tristan de Montebello, a finalist in the World Championship of Public Speaking. He also co-founded UltraSpeaking (ultraspeaking.com/james), where he teaches techniques to improve communication through games and real-world practice. We even played some of those games during this episode, and they surprised me with how much they revealed about my own speaking.

Public speaking isn’t just about giving a good talk—it’s about understanding who you are, what you stand for, and how you connect with others. I’ve been speaking for more than 25 years, but I’m still always looking for ways to improve. At the end of the day, sharing ideas—through writing, storytelling, or speaking—is how you can change the world.

This conversation with Tristan is fascinating because he’s gone from zero experience to becoming one of the best in the world, all while reverse-engineering what it takes to truly connect with an audience.

Episode Description

How does someone go from a complete beginner to a world-class speaker in less than a year? Tristan de Montebello did exactly that—and in the process, he uncovered the strategies, mindsets, and training methods that make communication powerful.

In this episode, James and Tristan break down the mechanics of storytelling, humor, vulnerability, and flow in speaking. They explore why audiences respond the way they do, how to use analogies to create connection, and why mindset is the foundation of every great communicator.

Whether you’re on a stage, in a meeting, or simply trying to share an idea with friends, these lessons will change the way you approach communication.

What You’ll Learn

• How Tristan went from novice to World Championship finalist in under a year.
• Why humor and vulnerability are essential ingredients for authentic connection.
• Practical ways to use storytelling and analogies to make ideas stick.
• How to handle insecurity, fumbles, and “tough audiences” without breaking flow.
• Why mindset—not technique—is the foundation of great communication.

Timestamped Chapters

• [01:00] A Note from James and introducing Tristan de Montebello
• [04:15] Inside the World Championship of Public Speaking
• [07:45] Humor, storytelling, and why connection matters
• [11:10] The Fear Olympics: lessons from Tristan’s grandmother
• [16:30] “Never be the hero of your own story”
• [20:15] Breaking down stories like Finding Nemo
• [24:45] How Tristan trained humor like a stand-up comic
• [28:30] What great speakers and clowns have in common 
• [33:20] Managing insecurities and staying in character
• [41:40] From finalist to struggling in an online mastermind
• [50:20] Slacklining as a metaphor for learning
• [54:10] Building analogies as a core communication skill 
• [60:30] Reading tough or quiet audiences
• [67:15] Handling bias and building trust with skeptical crowds
• [69:45] Flow state in public speaking

Additional Resources

• UltraSpeaking – ultraspeaking.com/james
• Toastmasters International – toastmasters.org
• Rich Dad Poor Dad by Robert Kiyosaki – Amazon link
• Eight Mile (film referenced by James & Tristan) – IMDb

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A Note from James

What does it take to make a discovery that changes the world? Think about landing on the moon — a true moonshot. Along the way, countless technologies were invented that reshaped life back on Earth.

My guest today, Astro Teller, has been part of that same kind of world-changing work. At X — Alphabet’s Moonshot Factory — he’s led projects that gave us self-driving cars, Google Brain, drone delivery, augmented reality with Google Glass, and much more. We even talk about quantum computing, drones that bring your groceries to your backyard, and the mindset it takes to believe in something that once sounded like science fiction.

Astro and I first crossed paths when I visited Google X back in 2012 or 2013. He was on this podcast in 2015, and now, ten years later, he’s back to talk about his own show — The Moonshot Podcast — and the latest bold projects that could shape our future

.

Episode Description

Astro Teller, Captain of Moonshots at Alphabet’s X, joins James to share how impossible-sounding ideas become real. From Waymo’s self-driving cars to Wing’s drones, from the birth of Google Brain to breakthroughs in quantum networking and modernizing electric grids, Astro explains the engineering mindset that drives innovation.

This episode goes beyond technology — it’s about how to think like a moonshot maker. You’ll hear how X chooses projects, why systems engineering often matters more than pure science, and how to break down massive problems into solvable steps.

What You’ll Learn

• The three elements that define a true moonshot at X.
• Why self-driving cars succeeded not because of new science, but because of paradigm-shifting systems engineering.
• How Google Brain kickstarted the modern AI revolution by betting on scale when neural nets were out of fashion.
• Why Wing’s drone delivery service may soon feel as ordinary as rideshare apps.
• How Project Tapestry is mapping and optimizing the electric grid to cut connection times from years to days.
• The promise (and risks) of quantum networking, quantum sensing, and the looming “Q-Day” when current cryptography could break.
• Why empathy is crucial for workers displaced by new technologies.

Timestamped Chapters

• [01:00] A Note from James
• [04:00] Inside Alphabet’s Moonshot Factory (X)
• [06:00] Defining moonshots: problem, radical solution, breakthrough tech
• [08:00] Waymo and the hidden challenges of self-driving cars
• [13:00] Safety, comfort, and the “body language” of cars
• [17:00] Google Brain and the rebirth of neural networks
• [20:00] Cats, YouTube, and AI’s first big proof point
• [23:00] Wing: drones delivering groceries like magic
• [29:00] Moonshot mindset vs. the Apollo mission
• [31:00] How X evaluates and selects moonshots
• [34:00] Breakthroughs behind Waymo and simulation at scale
• [39:00] What if every car was autonomous?
• [40:00] Project Tapestry: modernizing the electric grid
• [45:00] Mapping PJM and national-scale grids
• [46:00] Lessons from Google Glass: too early, or misframed?
• [48:00] The future of AR glasses and AI assistants
• [51:00] Why X left longevity research to Calico and Verily
• [52:00] Quantum computing, networking, and sensing explained
• [57:00] The coming “Q-Day” and what it means for security
• [59:00] AI, jobs, and the importance of empathy
• [61:00] Closing thoughts and Astro’s Moonshot Podcast

Additional Resources

• The Moonshot Podcast with Astro Teller (YouTube)
• X, the Moonshot Factory
• Waymo (Self-Driving Cars)
• Wing (Drone Delivery)
• Google Brain
• Project Tapestry – Grid Modernization
• PJM Interconnection (Eastern US Grid)
• Calico (Alphabet’s Longevity Research)
• Verily Life Sciences
• Sandbox AQ (Quantum & AI)
• Carnegie Mellon University School of Computer Science

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A Note from James

There’s always been debate about whether college is worth it. But what if there’s a better alternative—one that actually prepares you to become the person you want to be? My good friend Matt Smith just wrote a book with Doug Casey called The Preparation. It’s not theory—he’s been putting his own son through it as a real-world experiment. Instead of college, Maxim has spent the past two years learning skills like EMT training, firefighting, building houses, working cattle, and even launching a business. This is a practical roadmap for turning those years of 18–22 into a hero’s journey. I loved this conversation, and I’m sending the book to all of my kids.

Episode Description

James talks with entrepreneur and writer Matt Smith about his new book The Preparation, co-authored with Doug Casey. The book lays out a four-year alternative to college built around “cycles”—three-month intensive experiences designed to build practical skills, personal codes, and real-world wisdom. From earning an EMT license to fighting wildfires, training in Muay Thai, or running a small business, these cycles are designed to help young people become independent, capable, and resilient. James and Matt discuss why the traditional college path often fails, how to build a personal code of values, and why the future belongs to “expert generalists” who know how to learn across disciplines.

What You’ll Learn

• Why “be, do, have” is a more powerful framework for life than chasing possessions or credentials.
• How creating a personal code builds self-respect and identity.
• Why intergenerational relationships matter more than peer validation.
• How cycles of hands-on learning—from EMT work to entrepreneurship—prepare young people better than a classroom ever could.
• Why becoming an expert generalist is the best hedge against a future dominated by AI and automation.

Timestamped Chapters

• [00:00] A Note from James: College vs. alternatives
• [01:00] Introducing Matt Smith and The Preparation
• [03:00] Origins of the book and Doug Casey’s vision
• [05:00] Writing the book for his son Maxim
• [06:00] Why homeschooling replaced high school
• [07:00] “Be, Do, Have” explained
• [09:00] Stacking cycles vs. stacking skills
• [10:00] Why the book focuses on young men (and how women can adapt it)
• [11:00] How to build your own cycle
• [13:00] Why traditional education fails to prepare people for real skills
• [14:00] Establishing a personal code
• [16:00] Examples of personal rules for self-respect
• [18:00] Practicing courage and choosing virtues
• [20:00] Skills Maxim has gained so far—EMT, chess, horses, firefighting
• [22:00] Adventures with Doug Casey and small-country nation building
• [24:00] Maxim’s cycles: EMT work, ranch apprenticeship, wildfire EMT
• [27:00] Structure, resistance, and learning by doing
• [28:00] Shelter Institute and learning to build a house
• [29:00] Entrepreneurship cycle: precision agriculture with drones
• [31:00] Lessons from entrepreneurship
• [32:00] Muay Thai training in Thailand
• [33:00] Cooking school in Florence
• [34:00] Travel with purpose vs. aimless wandering
• [36:00] James on biographies and meaningful decisions
• [37:00] Preparing for AI and the future of work
• [39:00] Why being an “expert generalist” matters
• [41:00] Learning how to learn across environments
• [42:00] The problem with peer-only education
• [44:00] Intergenerational relationships as mentorship
• [45:00] What comes after the preparation
• [47:00] Why the program can work for adults too
• [49:00] Rethinking retirement as another cycle of preparation
• [56:00] Matt’s personal growth through writing and learning new skills
• [58:00] Designing The Preparation as a beautiful, interactive book
• [59:00] Closing thoughts and sending the book to the next generation

Additional Resources

• Matt Smith & Doug Casey — The Preparation
• Doug Casey’s Take (Podcast): YouTube Channel
• Doug Casey’s Official Site: internationalman.com
• The Shelter Institute (Learn to Build a House): shelterinstitute.com
• Muay Thai Training in Thailand (Example School): Santai Muay Thai Gym
• Florence Cooking School Example: Apicius International School of Hospitality
• Stripe Press (Books mentioned by Matt): stripe.press
• Doug Casey’s Classic Book — Crisis Investing: Amazon

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Episode Description

James sits down with Case Kenny, author of The Opposite of Settling and host of New Mindset, Who Dis?, to talk about how our expectations around relationships shape the way we date and commit. Case shares the research, stories, and mindset shifts that helped him go from avoiding commitment in his twenties to finding fulfillment in a relationship that amplifies his independence. This episode challenges old narratives about “settling down” and offers a practical framework for building relationships that energize rather than diminish.

What You’ll Learn

• Why “settling down” is the wrong framework for love—and how to reframe it as “settling up.”
• How the liking gap skews our perception of how others see us, and what that means for dating.
• The importance of dating to be seen instead of dating to be liked.
• Why non-conforming traits (your “weirdness”) can actually make you more attractive.
• How playfulness and humor serve as the foundation for strong, lasting relationships.

Timestamped Chapters

• [00:00] Rethinking independence in relationships
• [01:00] James introduces Case Kenny and The Opposite of Settling
• [02:00] Why the phrase “settle down” shaped Case’s early resistance to commitment
• [05:00] Letting relationships fade: what Case learned from avoidance
• [07:00] Meeting Emily and the power of a “slow burn”
• [09:00] Timing vs. compatibility in finding a partner
• [11:00] The “liking gap” and how it affects dating behavior
• [13:00] Performance mode vs. being present
• [14:00] Dating to be seen, not just to be liked
• [15:00] The value of non-conforming traits in attraction
• [17:00] From introversion to self-expression through podcasting
• [20:00] Knowing yourself before you can know what you want
• [21:00] The peak-end rule and distorted memories of relationships
• [23:00] Appreciating past relationships without villainizing them
• [25:00] How the brain can reinforce unhelpful dating patterns
• [27:00] The case for showing up fully on first dates
• [29:00] Learning from rejection and getting clarity fast
• [31:00] Why regret often comes from the wrong relationship, not from being single
• [33:00] Playfulness as the true purpose of relationships
• [35:00] Humor and “bids for connection” as relationship foundations
• [37:00] The importance of noticing your partner
• [38:00] Why James listened to standup comedy before dates
• [39:00] Wrapping up with Case Kenny

Additional Resources

• Case Kenny — The Opposite of Settling: PenguinRandomhouse.com
• Case Kenny — Single Is Your Superpower: New Mindset, Who Dis?
• New Mindset, Who Dis? (Apple Podcasts): Apple Podcasts
• The Gottman Institute — “Bids for Connection” (overview): Start paying more attention to bids. Gottman Institute
• Research — “The Liking Gap” (Boothby et al., 2018, PDF): Yale Clark Relationship Lab. Clark Relationship Lab
• Explainer — Peak–End Rule: The Decision Lab
• Case Kenny on X (Twitter): @thecasekenny

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