It’s Alex Danco’s landmark 10th appearance on Infinite Loops!

He joins the show to discuss his move from Shopify to a16z (where he'll be building out their editorial operations), the power dynamics between VCs and founders (the kings and priests of our era), communication theory and the power of speechwriting, Reagan's rhetorical genius, authentic weirdos, America's hypomanic DNA, the unexpected similarities between American and Chinese culture, and why listeners who haven't read any recommended books after 10 episodes are wasting their time.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Website
• Twitter
• Newsletter

Show Notes:

• Alex’s New Gig
• A Civil War Between Elites
• The Citizen Kane Test for CEOs
• Communication is the Founder's Job
• VCs as Legitimacy Banks & Magic-Makers
• The Lost Art of Speechwriting
• Reagan's Genius & The American Dream
• The Hypomanic Edge
• Mystery, Respect, and Cultural Power
• Marketing Ideas to the Right Audience
• The New Internet Economy
• Maritime Laws for AI Agents
• The Goth Index and Authenticity
• Substack's Identity Crisis & The Role of Podcasts
• Alex as Emperor of the World (Again)

Books Mentioned:

• What Works on Wall Street; by Jim O'Shaughnessy
• How Music Works; by David Byrne
• Breakneck: China’s Quest to Engineer the Future; by Dan Wang
• The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; John D. Gartner
• The Language of Magic; by Toby Chapel
• Underwriters of the United States: How Insurance Shaped the American Founding; by Hannah Farber

Sangeet Paul Choudary, bestselling author of Platform Revolution and Reshuffle, and senior fellow at UC Berkeley, joins the show to challenge the conventional wisdom about AI's impact on our economy. We explore why knowledge workers risk falling "below the algorithm," how curiosity and judgment become luxury goods in a world of cheap answers, and why our educational and career structures need complete reinvention rather than incremental reform.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Reshuffle: Who Wins When AI Restacks the Knowledge Economy (Amazon)
• Website
• Twitter
• Substack
• LinkedIn

Show Notes:

• Sangeet’s Core Thesis
• Technology's Second Order Effects
• Coordination Without Consensus
• Resistance to Innovation
• The Bottlenecks of Changing Systems
• Staying Above The Algorithm
• An Impending Cognitive Chasm
• The Limitations of Reskilling
• Redesigning Hiring for the AI Era
• The Human Touch Fallacy
• The End of Linear Career Paths
• Collective Sense-making in Uncertainty
• Sangeet as Emperor of the Day

Books Mentioned:

• Platform Revolution; by Geoffrey G Parker, Marshall W Van Alstyne, Sangeet Paul Choudary
• Reshuffle; by Sangeet Paul Choudary
• The Hound of the Baskervilles; by Arthur Conan Doyle
• Why Greatness Cannot Be Planned; by Kenneth Stanley and Joel Lehman

Michael Dean — architect-turned-writer, O’Shaughnessy Fellow, and creator of Essay Architecture — joins the show to explore the hidden structures beneath nonfiction and why essays, like buildings, can be designed with patterns rather than left to inspiration.

We discuss the origins of Essay Architecture, Michael’s 27-pattern framework that maps essays across Idea, Form, and Voice, and how to make craft teachable and AI feedback useful without replacing the writer. Along the way, we dive into architecture school critiques, why publishable doesn’t mean perfect, how editing rewires thinking, and the cultural risks if we keep treating writing as vibes instead of patterns.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Michael’s Website
• Substack
• X/Twitter Profile

Show Notes:

• The Architecture of Essays: from Design School to Writing Frameworks
• The Pattern Language: Idea, Form, and Voice
• Local Nuance vs Global Stylekits
• Fundamentals before Breaking Rules: Joyce, Picasso, the Beatles
• Quality Without a Name
• Leveling the College Playing Field
• The Two Sandboxes of Fundamentals and Amplification
• Gamification, Play and Motivation
• Beyond the Five-paragraph Essay: Emerson and AI in Education
• Scoring Great Essays: Why David Foster Wallace takes Three Top Spots
• How Writing Colonized the brain
• Editing as Belief-rewiring: Why Writers Avoid It and Why Math Helps
• The King of Biases: Confirmation Bias
• Michael as Emperor of the World

Books Mentioned:

• Works on Wall Street; Jim O’Shaughnessy
• Essay Architecture (in progress) ; by Michael Dean
• A Pattern Language; by Christopher Alexander
• The Best American Essays 2024 Anthology; by Wesley Morris and Kim Dana Kupperman
• Consider the Lobster; by David Foster Wallace
• The White Album; by Joan Didion
• Shooting an Elephant; by George Orwell
• Portrait of an Artist as a Young Man; by James Joyce
• Finnegan’s Wake; by James Joyce
• Towards a Golden Age; Paul Graham
• The Limits of Scientific Reasoning; by David Faust
• The WEIRDest People in the World; by Joseph Henrich

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to November 2023, when we welcomed the one and only Roon.

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AI researcher, memelord extraordinaire, and techno-optimist Roon joins the show to discuss coming up with the shape rotator vs. wordcel meme, what an AGI world could become, and why Tenet is Christopher Nolan’s best movie.

Important Links:

• Roon’s Twitter
• Roon’s Substack
• AGI Futures

Show Notes:

• Shape Rotators Vs. Wordcels
• Why AGI is Possible
• AI in Science Fiction
• AGI Future #1: Neuralink Third Impact
• AGI Future #2: Simulation Theory
• AGI Future #3: Dumb Matter
• AGI Future #4: Balrog Awakened
• AGI Future #5: Ultra Kessler Syndrome
• AGI Future #6: The Tragedy of Taiwan
• AGI Future #7: For Dust Thou Art
• AGI Future #8: CEV Super Intelligence
• Why Tenet is Christopher Nolan’s Best Movie
• Roon as Emperor of the World
• MORE!

Books Mentioned:

• The Lucifer Principle: A Scientific Expedition into the Forces of History; by Howard Bloom
• The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom
• The God Problem: How a Godless Cosmos Creates; by Howard Bloom
• William Blake vs the World; by John Higgs
• The Hitchhiker's Guide to the Galaxy; by Douglas Adams

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to August 2024, when we welcomed the one and only Gurwinder Bhogal.

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“We have created for ourselves a world that we didn't evolve for.”

Gurwinder Bhogal is, for my money, one of the most independent, original and insightful thinkers you’ll find in our corner of the internet.

He returns to discuss how willpower and good old-fashioned human agency can help us reclaim our mental sovereignty and escape the “constant avalanche of concerns that are being vomited over us through our laptop screens, our phones, our TV screens, and in conversations.”

For the full transcript, episode takeaways, and bucketloads of other stuff designed to make you go, “Hmm, that’s interesting!” check out our Substack.

Important Links:

• Gurwinder's Substack
• Gurwinder's Twitter
• Gurwinder’s previous Infinite Loops appearance

Show Notes:

• “We have created for ourselves a world we didn’t evolve for”
• The dogged persistence of our stubborn beliefs
• Gamification; generational differences in agency
• The societal impact of the education system’s changing priorities
• How to zombify a population
• Skin in the game: Gurwinder’s guide to reclaiming agency
• LLMs, bullshit, and the atomization of culture
• How to play better games
• Willpower is the bottleneck
• Gurwinder as emperor of the world
• MORE!

Books Mentioned:

• Why Everything is Becoming a Game; by Gurwinder Bhogal
• Think Again: The Power of Knowing What You Don't Know; by Adam Grant
• The Status Game: On Human Life and How to Play It; by Will Storr
• The True Believer: Thoughts on the Nature of Mass Movements; by Eric Hoffer
• Why the Mental Health of Liberal Girls Sank First and Fastest; by Jonathan Haidt (After Babel)
• America’s Colleges Are Reaping What They Sowed; by Tyler Austin Harper (The Atlantic)
• Joe Biden and the Common Knowledge Game; by Ben Hunt (Epsilon Theory)
• The Emperor’s New Clothes; by Hans Christian Andersen
• Futarchy Details; by Robin Hanson (Overcoming Bias)
• The Enlightenment Trilogy; by Jed McKenna
• The Weirdest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich

What happens when a self-described "not very good" venture capitalist discovers he has an extraordinary gift for coaching the world's most successful CEOs? Joe Hudson joins Infinite Loops to share his unconventional journey from Alaska fishing boats to Hollywood directing to Silicon Valley boardrooms, ultimately finding his calling in helping high-performers unlock their deepest potential.

This conversation dives deep into Joe's revolutionary three-center approach to human development—working with the head, heart, and nervous system simultaneously to create lasting transformation, and MORE!

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Sign up for a complimentary transformation guide: artofaccomplishment.com
• Listen to the Art of Accomplishment Podcast on Spotify
• Listen to the Art of Accomplishment Podcast on YouTube
• Joe Hudson's Twitter
• Joe Hudson's LinkedIn

Show Notes:

• Opening
• Joe's Unconventional Coaching Philosophy
• The Artist in the Art
• The "Should" Trap & The Trash Can Experiment
• Game Rules & Emotional Decision-Making
• The Curiosity Override
• The Big Five & CEO Personality Patterns
• The Three-Center System
• The Disinterested Observer & Emotional Suppression
• John Sarno & The Mind-Body Connection
• Fear & Gratitude
• Escaping the Logic Box
• Invest in Great Entrepreneurs
• The Tennis Ball & Quarter Analogy
• Micro Expressions & Unconditional Love
• Buddhist Monks & The last Taboo
• Trustafarians & Multi-Generational Wealth
• AI, Wandering & The Rat Park
• Joe as Emperor of the World

Authors & Books Mentioned:

1. Prometheus Rising; by Robert Anton Wilson
2. Quantum Psychology; by Robert Anton Wilson
3. Zen and the Art of Motorcycle Maintenance; by Robert Pirsig
4. Mind Over Back Pain; by John Sarno
5. Molecules of Emotion; by Candace Pert
6. Adventures of a Bystander; by Peter Drucker
7. The Love Song of J. Alfred Prufrock; by T.S. Eliot
8. The Enlightened Brain; by Andrew Newberg

Michael Gibson and Danielle Strachman, co-founders of 1517 Fund, join the show to discuss their rebellion against higher education, why universities stifle creativity, why IQ doesn't correlate with innovation, and how betting on "misfit toys" is the way to go—plus we explore Girardian mimesis, the perishable nature of creativity, the laziness of pessimistic storytelling and MORE!

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• 1517 Fund
• Michael’s Twitter
• Danielle’s Twitter
• 1517 Substack

Show Notes:

• Why 1517 Fund Rebels Against Higher Education
• Giving Individuals a Shot
• “It’s cool to be building stuff, it’s not cool to be a Thiel Fellow”
• The ‘ATM Founder’ and ‘Rich Too Early’ Syndrome
• The Power of Predictive Character Traits
• Flipping Credentialist Thinking
• "How do we become Spielberg? How do we do something truly great?"
• Simple Memes and Powerful Narratives
• Avoiding a Monoculture of Misfits
• The Incestuous Universities Scene
• Choosing Your Own Path
• People Contain Multitudes
• Michael and Danielle as World Emperor and Empress

Books & Essays Mentioned:

• A Mind at Play: How Claude Shannon Invented the Information Age; by Jimmy Soni and Rob Goodman
• Collective Illusions: Conformity, Complicity, and the Science of Why We Make Bad Decisions; by Todd Rose
• "A Gift for My Daughter"; by Harry Browne (Full text available here)
• Paper Belt on Fire; by Michael Gibson
• The Idea Factory: Bell Labs and the Great Age of American Innovation; by Jon Gertner
• The Right Stuff; by Tom Wolfe
• The Status Game; by Will Storr
• The Two Cultures; by C.P. Snow
• What Works on Wall Street; by Jim O'Shaughnessy
• White Mirror: Stories; by Tinkered Thinking
• Zero to One; by Peter Thiel
• The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley; by Jimmy Soni
• Rome's Last Citizen: The Life and Legacy of Cato, Mortal Enemy of Caesar; by Jimmy Soni and Rob Goodman
• How I Found Freedom in an Unfree World; by Harry Browne

Ed Latimore: boxer, physicist, and author of Hard Lessons from the Hurt Business makes his third appearance on the show to discuss hard-won wisdom about impulse control, self-forgiveness, the challenges of modern parenting and why being discerning (not judgmental) about your social circle might be the simplest rule for a better life.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Ed’s Twitter
• Ed’s Website
• Ed’s Substack
• Ed’s Previous Appearances: #1, #2

Show Notes:

• Punctuality and Impulse Control
• Ed’s Parenting Philosophy
• The Dilemmas of Raising Kids
• Having Socratic Dialogues with Six Year Olds
• Exposure to Different Realities
• The Journey to Getting Sober
• Learning from Experience
• How Stories Transmit Values
• Justice and Forgiveness
• Self-Talk and Internal Narratives
• Race, Merit, and Cultural Double Standards
• Falsifiability and Rational Thinking
• Ed as World Emperor

Books Mentioned:

• The Triple Package; by Amy Chua and Jed Rubenfeld
• Hard Lessons from the Hurt Business; by Edward Latimore
• What Works on Wall Street; by Jim O'Shaughnessy
• Boxing and the Art of Life; by Edward Latimore