Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300)
Infinite Loops
What happens when you design a company assuming AI should do everything it possibly can? Jean-Marc Daecius, OSV's Chief of Staff, joins Infinite Loops to explain what it means to be “AI first” — and why he believes he may be the company's last human chief of staff. The conversation explores how AI can remove meaningless cognitive load, protect deep work, and unlock creative leverage — from reshuffling priorities and filtering email, to reinventing publishing, agriculture, education, and even how we discover books, movies, and ideas. Important links: Substack: Jean...
info_outline
John Wang - The Man Who Built The Queens Night Market (Ep. 299)
Infinite Loops
The Queens Night Market is one of New York City’s most beloved institutions — but it was never supposed to last more than a year. John Wang, founder of the Queens Night Market, joins Infinite Loops to explain how a side project with a “terrible business model” unexpectedly became one of the most celebrated food markets in the world. From leaving a traditional legal career to imposing a strict price cap in one of the most expensive cities on earth, John shares how the market evolved into a cultural institution representing more than 100 countries through food. Important links:...
info_outline
Cliff Asness - Surviving the Meme Stock Bubble (Ep. 298)
Infinite Loops
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: Cliff's Perspectives: Cliff's X:
info_outline
Tomás Pueyo — Explaining the World Through Geography, History and Data (EP. 297)
Infinite Loops
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:
info_outline
Annie Duke — Why We Make the Wrong Decisions (Ep. 296)
Infinite Loops
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: Annie's website: ...
info_outline
Jimmy Soni — The Publishing System is Broken (EP. 295)
Infinite Loops
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/...
info_outline
Guy Spier — Wealth, Wisdom & Enlightenment (Infinite Loops CLASSICS)
Infinite Loops
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! _________________ 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...
info_outline
Vik Muniz — The Art of Perception (EP.294)
Infinite Loops
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....
info_outline
Marc Dennis — Painting the Punchline (EP.293)
Infinite Loops
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...
info_outline
Ariel Meyerowitz — Navigating the Art World (EP. 292)
Infinite Loops
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...
info_outlineFrom 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