Artist Marc Dennis joins Jim O'Shaughnessy to explore the intersection of hyper-realism, humor, and the "meta-narrative." Marc shares his incredible non-linear journey—from accidentally starting a forest fire at age seven to becoming a tenured professor and eventually betting it all to become a full-time artist with no plan B. They discuss why the "key to failure" is trying to please everyone, how humor acts as a survival mechanism, and the crucial difference between perception and reality. Marc also offers a masterclass on intention, explaining why he plants hidden stories within his paintings and sharing the profound realization that you cannot love others until you love yourself. This conversation is a deep dive into the creative mind, offering insights on resilience, identity, and the art of betting on yourself. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!", check out our Substack.

#Art #Creativity #Hyperrealism #Philosophy #MentalModels #Resilience #Humor #Psychology

Important Links:

Substack: https://newsletter.osv.llc/

Marc's Website: http://www.marcdennis.com/

Marc's Instagram: https://www.instagram.com/darcmennis/

Books mentioned:

Meditations by Marcus Aurelius

The Twelve Caesars by Suetonius

Professional art advisor Ariel Meyerowitz joins Jim O'Shaughnessy to demystify the complex world of art. Ariel provides an essential guide for aspiring collectors, explaining where to begin, how to develop your eye, and why buying what you love is the most important first step. They explore the inner workings of galleries, auctions, and art fairs, contrasting the emotional value of art with the often-fickle investment market. Ariel also shares her philosophy on patronage, the psychology of collecting, and the profound, stress-reducing impact of living with art. This conversation is a perfect starting point for anyone looking to break into the art world, offering a clear path from intimidation to appreciation.

#Art #ArtCollecting #Investing #Culture #Creativity #MentalModels #Innovation #Design #Psychology #Philosophy

Important Links:

Substack: https://newsletter.osv.llc/

Ariel's Website: https://www.arielmeyerowitz.com/

Books mentioned:

The Painted Word by Tom Wolfe

Adam Moskowitz is the King of Cheese—but his path to the throne was anything but straight. In this delicious episode of Infinite Loops, Adam shares his wild journey from a failed rap career and a battle with addiction to becoming one of the most influential figures in cheese and the host of A Cheese Course.

Whether you are a foodie, a creator battling gatekeepers, or just someone who loves a good comeback story, this episode will remind you to bet on yourself—and maybe eat some better cheese while you're at it.

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.

Show Notes:

• The "Cheese Quake" origin story and the failed rap career

• Why "Creamy" is a texture, not a flavor

• The Artisan Cheese Illuminati

• Creating a documentary when gatekeepers said "No"

• The "Olive Garden" insult that fueled a fire

• Is the "Banana on the Wall" actually art?

• Cognitive diversity and why echo chambers kill creativity

• The "Time Horizon is Infinite" philosophy

• Leaders Lead & Lead with Love

Books & Ideas Mentioned:

• My Dinner with Andre (Movie)

• Candide by Voltaire (Dr. Pangloss)

• Kubla Khan by Samuel Taylor Coleridge

• Claude Shannon (Information Theory)

From a 0.9 GPA in rural Utah to the faculty of Harvard, Todd Rose's life is a testament to the idea that the "standard path" is a myth. In this return appearance on Infinite Loops, Todd opens up about the gritty, unvarnished reality of his origin story—a journey that includes ten minimum wage jobs, a stint administering enemas for a living, and the life-changing intervention of a department secretary named Marilyn Diamond.

We dive deep into the "Dark Horse" mindset and why the pursuit of fulfillment, rather than the pursuit of excellence, is actually the most reliable driver of success. We also bond over our mutual disdain for Frederick Taylor, explore the devastating impact of "average-based" thinking on human potential, and discuss why dignity is the bedrock of a free society—illustrated by a heartbreaking personal encounter with a jar of chunky peanut butter.

If you've ever felt like a square peg in a round hole, or if you're looking for a roadmap to navigate the coming cultural shifts in the age of AI, this conversation is essential listening.

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.

Show Notes:

• The 0.9 GPA and the "Correct Answer Machine"

• Ten minimum wage jobs and the advice to "get longer gloves"

• Marilyn Diamond: The improbable mentor who saved Todd's education

• The "No Average Brain" discovery in neuroscience

• Why we both despise Frederick Taylor and Scientific Management

• Dark Horses: Ignoring the destination to find the path

• Degrees of Freedom: How Todd hacked the GRE

• The "Chunky Peanut Butter" story and the importance of dignity

• Resentment, trust, and the future of AI

• The "Rainy Day Club" and how paradigms actually shift

Books Mentioned:

• Collective Illusions; Todd Rose

• The End of Average; Todd Rose

• Dark Horse; Todd Rose

• Improbable Mentors; Mike Perry

• The Principles of Scientific Management; Frederick Taylor

• The Structure of Scientific Revolutions; Thomas Kuhn

• The Wealth of Nations; Adam Smith

• Man's Search for Meaning; Viktor Frankl

• Dignity; Chris Arnade

• Capitalism, Socialism and Democracy; Joseph Schumpeter

Hello everyone, Jim here. We're taking a brief break from new episodes to spotlight a golden oldie from the Infinite Loops archive. This conversation from December 2023 remains one of my favorites. Fresh episodes return next week, but first, enjoy this conversation with the inimitable George Mack.

_________________

Writer, marketer, entrepreneur, and master of mental models, George Mack returns to discuss the top 0.1% of ideas he's ever come across, from treating life as a video game to spotting high-agency individuals. Important Links:

• George's Twitter
• The Lindy Library
• Roy: A Life Well Lived (Rick and Morty)
• How to Spot High Agency People
• The Mack Meditation
• What is ignored by the media — but will be studied by historians?
• The Early-Late Razor

Show Notes:

• Treating Life as a Video Game
• Finding the Important Metrics
• Embrace Momentum; Embrace Constraints
• How to Spot High Agency People
• How to Increase Your Agency
• The Mack Meditation & Silence as Alpha
• Why Pessimism vs Optimism is the Wrong Debate
• The Future of Media
• What is Ignored by the Media but will be Studied by Historians?
• The Reddit to Facebook Continuum
• George's Most Midwit Opinion
• Randomness & Feeding the Algorithm
• How to Retain Curiosity
• George as Emperor of the World

Books Mentioned:

• The Hypomanic Edge: The Link Between (a Little) Craziness and (a Lot Of) Success in America; by John Gartner
• Happy: Why More or Less Everything is Absolutely Fine; by Derren Brown
• What Works on Wall Street; by Jim O'Shaughnessy
• The Secret; by Rhonda Byrne
• Gödel, Escher, Bach: an Eternal Golden Braid; by Douglas Hofstadter
• The Beginning of Infinity: Explanations that Transform the World; by David Deutsch

What happens when a shy farm kid from rural Wisconsin who never dreamed of being a writer becomes one of America's most beloved storytellers? Michael Perry joins Infinite Loops to share his remarkable journey from cleaning calf pens to pitching scripts at Universal Studios, all while maintaining his day job as a volunteer firefighter and EMT in his hometown.

This conversation is a masterclass in authentic storytelling, practical wisdom, and the power of staying true to your roots while navigating an industry that often values credentials over character. Perry shares unforgettable stories about turning down Oprah (yes, really), why he sells hundreds of books to "people who don't read" at firefighter conventions, and how his nursing background taught him the most important skill for any writer: human assessment. We explore his philosophy of "kindness is not weakness," the difference between cash and cachet, and why sometimes the best career move is knowing when not to move at all.

Whether you're a writer, entrepreneur, or simply someone who believes in the power of authentic storytelling, this episode will remind you that sometimes the best way forward is to embrace your own improbable path and never stand behind a sneezing cow.

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 Perry's website
• Substack - Michael Perry's Voice Mail
• Michael's X / Twitter
• LinkedIn
• Instagram
• Michael Perry's Mailing List

Show Notes:

• Connections with Mark Twain
• The NFL Friend & First Investment
• Mark Twain's European Fame & American Diplomacy
• Blue Collar vs. Capital 'A' Art
• Flying Under the Radar
• Midwestern Wisdom & Family Stories
• Charity, Humility, & Fundamentalist Upbringing
• The Positive Side of Imposter Syndrome
• Happy Tangents vs. Detailed Blueprints
• Publishing Industry Frustrations
• EMT Requires Pulse & Driver's License
• The Oprah Story
• First Mover Disadvantage
• Brothers, Guns, & Material Sources
• Mortality & Perspective
• The Gimlet-Eyed Drive
• Visiting Tom
• The Reality of Writing Today
• Pragmatism & Adaptation
• Voltaire & Historical Perspective
• Mike as Emperor of the World

Books Mentioned:

• A Tale of Two Cities; Charles Dickens
• Mark Twain; Ron Chernow
• Improbable Mentors and Happy Tangents; Michael Perry
• Population: 485; Michael Perry
• Visiting Tom; Michael Perry
• Truck: A Love Story; Michael Perry
• Million Billion; Michael Perry
• 40 Acres Deep; Michael Perry
• Montaigne in Barn Boots; Michael Perry
• The Peter Principle; Laurence J. Peter
• What Works on Wall Street; Jim O'Shaughnessy
• Invest Like the Best; Jim O'Shaughnessy
• How to Retire Rich; Jim O'Shaughnessy
• Greatness Cannot Be Planned; Ken Stanley
• The Bible
• All Quiet on the Western Front; Erich Maria Remarque
• Tao Te Ching; Laozi
• Gone With the Wind; Margaret Mitchell
• Serpico; Peter Maas
• Candide; Voltaire

Ken Stanley – AI researcher and author of "Why Greatness Cannot Be Planned" – joins me to explore why ambitious objectives can blind us to the stepping stones that make breakthroughs possible. Ken is the inventor of the novelty search algorithm and co-creator of Picbreeder, a crowdsourced evolutionary art experiment that has led to important insights about our objective-obsessed culture.

This conversation covers everything from why vacuum tubes had to come before computers, how the path you take to success matters more than the success itself, the "fractured entangled representation" hypothesis, why grant applications kill innovation, how education beats the playground mentality out of children, and why "interesting" is the opposite of random.

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:

• Personal Website
• X / Twitter
• LinkedIn
• Google Scholar
• Wikipedia
• Book: Why Greatness Cannot Be Planned

Show Notes:

• Are We Deterministic Thinkers Living in a Probabilistic World?
• Evolving Complexity and the NEAT Algorithm
• The Origins of Picbreeder
• The Power of Novelty Search
• The Cultural Impact of Non-Objective Thinking
• Why Pursuing Interestingness is Not the Same as Being Random
• Mechanizing Serendipity via Stepping Stones
• The Allure of the Security Blanket
• The Omni-culture of NSF Funding
• What Makes an Innovator?
• The Fractured Entangled Representation Hypothesis
• What does it say about LLMs if They Are Fractured and Entangled?
• Path Dependency and Careers
• Ken as Emperor of the World

Books Mentioned:

• Why Greatness Cannot Be Planned; by Kenneth Stanley (and Joel Lehman)
• The God Problem; by Howard Bloom
• The Lucifer Principle; by Howard Bloom
• Global Brain; by Howard Bloom
• The Beginning of Infinity; by David Deutsch
• Invest Like the Best; by Jim O'Shaughnessy
• A Mind At Play; by Jimmy Soni

Writer, editor, and founder of The Elysian, Elle Griffin joins me on Infinite Loops to discuss her vision for participatory capitalism, a world where ownership, reputation, and creativity are shared more broadly across society.

We explore the evolution of capitalism from the industrial era to the networked age, how broad-based ownership could rebuild the middle class, why optimism is revolutionary, and how storytelling shapes our collective imagination.

We also discuss how reputation is becoming a new form of capital and how writers can become architects of meaning in a world reshaped by AI and automation. I hope you enjoy this 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:

• The Elysian
• Elle Griffin on X (Twitter)
• LinkedIn
• Website
• Elle's Novel Obscurity

Show Notes:

• The New GI Bill for Stock Ownership
• Rethinking ESOPs, RSUs, and Equity for All
• The Founder's Dilemma: Risk, Ownership & Exit
• Tax Incentives for Employee Ownership
• A Tale of Two Experiments
• The Ownership Czar for the Day
• The Future of Work
• The State with Baby Bonds
• The Problem with Worth and Deserving
• The Power of Utopian Fiction
• The Currency of Belief and Reputation
• Empress of the World Question

Books and References Mentioned:

• Obscurity; by Elle Griffin
• The Elysian; by Elle Griffin
• The Beginning of Infinity; by David Deutsch
• The Lessons of History; by Will & Ariel Durant
• The History of Civilization; by Will & Ariel Durant
• Why Greatness Can't Be Planned; by Kenneth O. Stanley
• Looking Backward; by Edward Bellamy
• Herland; by Charlotte Perkins Gilman
• Les Misérables; by Victor Hugo
• Frankenstein; by Mary Shelley
• The Republic; by Plato
• Das Kapital; by Karl Marx
• The Count of Monte Cristo; by Alexandre Dumas
• 20,000 Leagues Under the Sea; by Jules Verne
• A Tale of Two Cities; by Charles Dickens
• White Mirror Stories; by Infinite Books

What if the biggest barrier between you and your dreams isn't talent, connections, or luck— but simply the belief that you need permission to act? Jay Yang joins Infinite Loops to challenge one of the most limiting assumptions of our time: that opportunities must be handed to us rather than created by us.

At just 16, Jay cold-emailed the CEO of Beehiiv with a concrete plan that led to an internship. At 17, he sent Noah Kagan a 19-page audit of his email funnel with ready-to-ship assets, ultimately becoming head of content and helping put "Million Dollar Weekend" on the New York Times bestseller list. His secret? Understanding that preparation beats bravado, that most doors don't even have locks, and that the fastest way to get what you want is to do the work upfront and make saying "yes" a no-brainer for others.

This conversation dives deep into Jay's philosophy of permissionless action, exploring why most people accept the "standard pace" when there's actually no speed limit, how to reprogram limiting beliefs through small wins, and why high agency people focus on outputs while low agency people get trapped tracking inputs.

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:

• Jay Yang's website
• Jay Yang's X
• Jay Yang's Instagram
• Jay Yang's Book, You Can Just Do Things
• Jay Yang's LinkedIn

Show Notes:

• The Philosophy of Permissionless Action
• Breaking Free from Era-Defining Ideas
• Overcoming Limiting Beliefs
• Starting Small: Building Confidence Through Micro-Actions
• Inner vs. Outer Orientation
• Inputs vs. Outputs: The Agency Divide
• Failure as Feedback
• The Power of Persistence
• Curiosity and Cognitive Diversity
• AI and the Future of Work
• The Busy-ness Trap
• Signal vs. Noise in the AI Era
• People You Learn From Don't Have Huge Following
• The TAG Method Explained
• The New Way of Hiring
• Learning from the Greats
• Motivation vs. Clarity
• Jay's North Star and Anti-Goals
• Viktor Frankl and Finding Your Why
• Working in Public
• The Second Book Preview
• The Emperor Question
• Closing & Contact Information

Books Mentioned:

1. You Can Just Do Things: The Power of Permissionless Actions (Jay Yang)
2. Million Dollar Weekend by Noah Kagan
3. The Tao of Kobe (forthcoming 2026, Jimmy Soni)
4. Greatness Cannot Be Planned (Ken Stanley)
5. Man's Search for Meaning (Viktor Frankl)

Jeff Bussgang — entrepreneur, venture capitalist, Harvard Business School professor, and co-founder of Flybridge Capital — joins Infinite Loops to explore how AI is transforming the operating systems of startups.

We dive into Jeff's framework from his new book The Experimentation Machine, why AI compresses the cost and time of learning, how to distinguish 10X founders and 10X joiners, and why execution velocity matters more than tech moats in the age of AI.

One of the most important things Jeff and I discuss is why discernment and taste may be the most valuable human skills of the future. I hope you enjoy this 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:

• Flybridge
• Jeff's Wikipedia Profile
• Jeff's Website
• Jeff on LinkedIn
• Jeff's Twitter

Show Notes:

• AI and the Rise of the 10X Founder
• The HUNCH Framework for Product-Market Fit
• Hair-on-Fire Value Props vs. Vanity Metrics
• Head in the Clouds, Feet on the Ground
• The Kill Criteria
• The 3Ts That VCs Look For
• Creating Win-Win Outcomes: MongoDB
• What Makes a 10X Founder
• The Human Edge in the Age of AI
• Everybody is in Sales
• Who is a 10X Joiner?
• Emperor of the World: Jeff's Two Rules for Humanity

Dan Wang, author of "Breakneck: China's Quest to Engineer the Future," joins me to explore why China builds while America blocks, how lawyers strangled U.S. infrastructure, and why Connecticut trains run slower than they did in 1914. Dan lived through China's trade war, Zero COVID, and the exodus of 15,000+ Chinese millionaires, giving him unique insight into both superpowers' pathologies.

This conversation covers everything from why ribbon-cutting ceremonies matter for societal optimism to how lawyers morphed from deal-makers to obstructionists after the 1960s. We explore California's high-speed rail fiasco, the rebellion against NIMBYism, and Dan's prescription: America needs 20% more engineering, China needs 50% more lawyerly protections. Plus we discuss cognitive diversity, the Death Star versus the Rebel Alliance, and why we need synthesis.

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:

• Personal Website
• X / Twitter
• LinkedIn
• Profile at the Hoover Institution

Show Notes:

• The Engineering State vs. the Lawyerly Society
• America's Lost Building Culture
• China's Gilded Age & America's Progressive Era
• Solutions for America's Building Crisis
• An Oncoming Battle of Elites
• Becoming Pro Development
• A Vision for a New Housing Fund
• China's Challenges
• Who Has a Better Shot At Change?
• Rickover: The Grand American Builder
• Dan's Uncertain Forecast of China
• Looking Ahead to 2035
• Dan As Emperor of the World