Stay ConnectedEvery 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!”
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!
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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:
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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.
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