Cliff Asness — co-founder, managing principal, and chief investment officer at AQR Capital Management — is one of the most influential quantitative investors of the last 30 years. He's also one of the most candid.

In this conversation, Cliff joins Infinite Loops to talk about why losses hurt more than wins, how bubbles form, why modern investing increasingly resembles gambling, and what the dot-com era can teach us about today's markets.

Important links:

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

Cliff's Perspectives: https://www.aqr.com/Insights/Perspectives

Cliff's X: https://x.com/CliffordAsness

Tomás Pueyo, the French-Spanish engineer and writer behind the successful "Uncharted Territories" Substack, joins us to dismantle the invisible forces that shape our history and future.

We cover why humans are horrible at understanding exponential change, the geographical advantages of the U.S, why the Luddites might have been right, the "social media politician" of the future, why education is mostly signaling, and how air conditioning and mosquito eradication could change the destiny of nations.

Important Links:

• Tomas's Website
• X / Twitter
• LinkedIn
• Substack: Uncharted Territories
• YouTube Channel

Annie Duke — former professional poker player, decision strategist, and bestselling author — joins us for a deep conversation about why smart people so often make bad decisions.

Annie explains why misinterpretation is more dangerous than misinformation, why data is often true but misleading, and how our brains are wired for certainty in a probabilistic world. From real-world media examples to investing, health decisions, and AI-generated insights, this episode explores how explanations feel satisfying — even when they're wrong.

Important links:

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

Annie's website: https://www.annieduke.com/

Jimmy Soni, CEO and editor in chief of Infinite Books, is back on Infinite Loops. We discuss what's broken in traditional publishing and how we're fixing it. We also dig into Jimmy's forthcoming book on Kobe Bryant, why the world needs more "problem authors," and why our goal is to make our authors millionaires.

We explore why most industries optimize for prestige instead of outcomes, how digital distribution has reshaped attention, and why authors — and creators more broadly — have more leverage than they realize.

Important Links:

Infinite Books: https://www.infinitebooks.com/

Jimmy's X: https://x.com/jimmyasoni

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

Books Mentioned:

The Founders by Jimmy Soni

A Mind at Play by Jimmy Soni

The Dao of Kobe by Jimmy Soni (Upcoming)

What Works on Wall Street by Jim O'Shaughnessy

Invest Like the Best by Jim O'Shaughnessy

How to Retire Rich by Jim O'Shaughnessy

The 4-Hour Workweek by Tim Ferriss

The Almanac of Naval Ravikant by Eric Jorgenson (transcribed as "Naval Akan")

Dispatches from Grief (Upcoming)

Mamba Mentality by Kobe Bryant

Slow Horses by Mick Herron

The Boys in the Boat by Daniel James Brown

Happy Holidays! We're taking a short break from new episodes this week so you can focus on finishing that Christmas dinner. We'll be back next Thursday with something new. In the meantime, why not tuck into this conversation with Guy Spier from January 2024, which remains one of my favorites. Enjoy!

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Guy Spier runs the Aquamarine Fund, an "investment partnership closely modeled on the original Buffet Partnerships." He is also a podcast host, YouTube creator, author of The Education of a Value Investor and the host of the annual investment gathering VALUEx. He describes his life's project as "a quest for wealth, wisdom and enlightenment."

Guy joins the show to discuss the differences between Switzerland and the US, how to unlock the British class system, what he learned from Warren Buffett, and MUCH more!

Important Links:

• Guy's Website
• Guy's Twitter
• Guy's YouTube Channel
• 3Blue1Brown (YouTube Channel)
• Numberphile (YouTube Channel)

Show Notes:

• The Differences Between New York, Switzerland & Paris
• Exploring the Dark Underbelly of New York Nightlife
• Psychedelics, Guns & Regulation
• The Advantages of Swiss Democracy
• Don't Short the United States
• The Branding Skill of the Royal Family
• Unlocking the Rules of the Class System
• Life Paths & Premeditation
• Luck, Opportunity & Non-Canonical Science
• Jim's Music Taste
• Mathematical Shenanigans
• Guy as Emperor of the World
• MORE!

Books Mentioned:

• How to Change Your Mind: What the New Science of Psychedelics Teaches Us about Consciousness, Dying, Addiction, Depression, and Transcendence; by Michael Pollan
• The Hypomanic Edge: The Link Between (a Little) Craziness and (a Lot Of) Success in America; by John Gartner
• Write It Down, Make It Happen: Knowing What You Want and Getting It; by Henriette Anne Klauser
• Invest Like The Best; by Jim O'Shaughnessy
• Outside, the Sky is Blue: The story of a family told with searing honesty, humour and love; by Christina Patterson

What if the invention that truly made us human wasn't the wheel, language, or even agriculture — but art? In this episode of Infinite Loops, we sit down with internationally renowned artist Vik Muniz to explore a radical and deeply human idea: that art — the ability to represent the world — may be humanity's most important invention after fire. Born in São Paulo and now collected by major museums around the world, Muniz reflects on his own life journey — from growing up in a Brazilian favela to redefining what art can be — and explains why the artwork is only ever half complete. The viewer finishes it.

#Art #Creativity #VicMuniz #Perception #Photography #Innovation #Documentary #Mindset #VisualArt #InfiniteLoops

Important links:

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

Vik's website: https://vikmuniz.net/

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.

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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:

• 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