Infinite Loops
Infinite Loops

Infinite Loops

Jim O'Shaughnessy

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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

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