Infinite Loops
Infinite Loops

Infinite Loops

Jim O'Shaughnessy

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Episodes

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Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!"

Recent Episodes

Ariel Meyerowitz — Navigating the Art World (EP. 292)
DEC 4, 2025
Ariel Meyerowitz — Navigating the Art World (EP. 292)

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

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96 MIN
Adam Moskowitz — The Way of the Cheesemonger (EP.291)
NOV 27, 2025
Adam Moskowitz — The Way of the Cheesemonger (EP.291)

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)

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74 MIN
Todd Rose — Escaping the Trap of the Standard Path (EP.290)
NOV 20, 2025
Todd Rose — Escaping the Trap of the Standard Path (EP.290)

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

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123 MIN
George Mack — The Game of Life (Infinite Loops CLASSICS)
NOV 13, 2025
George Mack — The Game of Life (Infinite Loops CLASSICS)

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.

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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:

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
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103 MIN
Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)
NOV 6, 2025
Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)

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:

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

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112 MIN