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!"
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Gurwinder Bhogal's Guide to Modern Survival (Infinite Loops CLASSICS)
Thursday, August 28, 2025 • Duration 01:41:22
Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to August 2024, when we welcomed the one and only Gurwinder Bhogal.
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“We have created for ourselves a world that we didn't evolve for.”
Gurwinder Bhogal is, for my money, one of the most independent, original and insightful thinkers you’ll find in our corner of the internet.
He returns to discuss how willpower and good old-fashioned human agency can help us reclaim our mental sovereignty and escape the “constant avalanche of concerns that are being vomited over us through our laptop screens, our phones, our TV screens, and in conversations.”
For the full transcript, episode takeaways, and bucketloads of other stuff designed to make you go, “Hmm, that’s interesting!” check out our Substack.
The Weirdest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich
Joe Hudson — The Art of Accomplishment (EP. 280)
Thursday, August 21, 2025 • Duration 01:33:17
What happens when a self-described "not very good" venture capitalist discovers he has an extraordinary gift for coaching the world's most successful CEOs? Joe Hudson joins Infinite Loops to share his unconventional journey from Alaska fishing boats to Hollywood directing to Silicon Valley boardrooms, ultimately finding his calling in helping high-performers unlock their deepest potential.
This conversation dives deep into Joe's revolutionary three-center approach to human development—working with the head, heart, and nervous system simultaneously to create lasting transformation, and MORE!
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.
The Disinterested Observer & Emotional Suppression
John Sarno & The Mind-Body Connection
Fear & Gratitude
Michael Gibson & Danielle Strachman — The 1517 Rebellion (EP.279)
Episode 279
Thursday, August 14, 2025 • Duration 01:31:19
Michael Gibson and Danielle Strachman, co-founders of 1517 Fund, join the show to discuss their rebellion against higher education, why universities stifle creativity, why IQ doesn't correlate with innovation, and how betting on "misfit toys" is the way to go—plus we explore Girardian mimesis, the perishable nature of creativity, the laziness of pessimistic storytelling and MORE!
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.
“It’s cool to be building stuff, it’s not cool to be a Thiel Fellow”
The ‘ATM Founder’ and ‘Rich Too Early’ Syndrome
The Power of Predictive Character Traits
Flipping Credentialist Thinking
"How do we become Spielberg? How do we do something truly great?"
Simple Memes and Powerful Narratives
Avoiding a Monoculture of Misfits
The Incestuous Universities Scene
Choosing Your Own Path
People Contain Multitudes
Michael and Danielle as World Emperor and Empress
Books & Essays Mentioned:
A Mind at Play: How Claude Shannon Invented the Information Age; by Jimmy Soni and Rob Goodman
Ed Latimore — The Art of Self-Transformation (EP.278)
Episode 278
Thursday, August 7, 2025 • Duration 01:45:24
Ed Latimore: boxer, physicist, and author of Hard Lessons from the Hurt Business makes his third appearance on the show to discuss hard-won wisdom about impulse control, self-forgiveness, the challenges of modern parenting and why being discerning (not judgmental) about your social circle might be the simplest rule for a better life.
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.
Sam Arbesman — Science, Complexity and Humanistic Computation (EP.277)
Episode 277
Thursday, July 31, 2025 • Duration 01:45:51
Sam Arbesman, complexity scientist, author of "The Magic of Code," and scientist in residence at Lux Capital, joins me for a wide-ranging exploration of how we navigate an increasingly complex world that often exceeds human comprehension.
We dive into the oral traditions that preserve crucial scientific knowledge, why cognitive diversity trumps demographic diversity, the forgotten innovations hiding in technological history, and Sam's vision for "Maxis 2.0".
This conversation had everything—from science fiction's cultural impact to the philosophy of intellectual humility. Sam and I discovered we're remarkably simpatico on how to think about complex systems, the importance of historical context, and why saying "I don't know" is the foundation of genuine learning.
I hope you enjoy this 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.
Nick Maggiulli — Climbing the Wealth Ladder (EP.276)
Episode 276
Thursday, July 24, 2025 • Duration 01:19:49
Nick Maggiulli, data scientist turned financial writer and COO of Ritholtz Wealth Management, joins me to discuss his latest book,The Wealth Ladder, which presents a six-level framework for building and managing wealth.
Warning: this episode will upend what you think you know about money. We explore why atypical results require atypical actions, how income and not budgeting is the real unlock for wealth mobility, and how many financial myths persist simply because they feel good. Nick also shares the personal rules he lives by, how wealth changes meaning, and why being rich doesn’t guarantee happiness.
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.
Money May Magnify Happiness But Can’t Manufacture It
Atypical Results Require Atypical Actions
The Risk of Financial Generalization
The Loneliness Tax
Some Legacies Can Be Built Without Capital
The Plateau Between Wealthy and Wealthier
When the Job Becomes a Side Hustle
The Spending Myth
The Baby Bond Idea
The Universal Basic Income Debate
Markets Evolve Faster Than Us
Kindness is Rare and Needed.
Lawrence Yeo — The Inner Compass (EP.275)
Episode 275
Thursday, July 17, 2025 • Duration 01:24:56
Lawrence Yeo — writer, illustrator and author of “The Inner Compass” — joins the show to discuss the power of intuition in an uncertain world.
We explore why embracing uncertainty leads to greater curiosity, how social conditioning pulls us away from our true north, why doing things for their own sake builds authentic conviction and how journaling the "whys" rather than the "whats" can transform your self-awareness.
This conversation flowed so naturally we jumped right in without a formal introduction! I hope you enjoy it 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.
Will Storr—The Status Game (Infinite Loops CLASSICS)
Thursday, July 10, 2025 • Duration 01:24:45
Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, here's my September 2022 chat with the always interesting Will Storr.
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Will Storr is an award winning journalist and author. His book ‘The Status Game’ transforms our understanding of human nature by demonstrating how our unconscious desire for status ultimately drives our behaviour.
The Stanford prison experiment and dominance games
The status games played by cults
Luxury beliefs
Why we are all moral hypocrites
The importance of being funny
Social status and socioeconomic status
Human OS and the education system
How status seeking leads to the “very best of human nature”
The murderous nature of reputation destruction
The post WW1 humiliation of Germany
Loaded magazine
Finding the true reason behind seemingly crazy beliefs
The value of religion
Trading status
Spreading humility
Why we could be wrong about our closest beliefs
Books Mentioned:
Rupert Sheldrake — On Scientism, Morphic Resonance and the Extended Mind (Infinite Loops CLASSICS)
Thursday, July 3, 2025 • Duration 01:07:51
Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to February 2024, when we welcomed the one and only Rupert Sheldrake.
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Rupert Sheldrake is a biologist and author of 9 books and over 100 scientific papers. A critic of what he sees as the scientific establishment’s dogmatic dedication to materialism, he is perhaps best known for his theory of “morphic resonance,” via which information and activity can be transferred across space and time. Rupert joins the show to discuss being branded a heretic, how to test for telepathy, his advice for young scientists, and MUCH more!
Aaron Stupple & Logan Chipkin — The Sovereign Child: Liberating Kids from the Tyranny of Rules
Episode 274
Thursday, June 26, 2025 • Duration 01:59:00
What if everything we think we know about raising children is not just wrong, but actively harmful? Aaron Stupple and Logan Chipkin, authors of "The Sovereign Child," join Infinite Loops to make a case so compelling and radical that it challenges the very foundation of modern parenting and education.
From birth, we're told that children need rules, structure, and authority to thrive. But what if this approach is crushing their natural creativity, problem-solving abilities, and authentic self-development? Stupple and Chipkin argue that children are people—full stop. They have reasons, preferences, and the capacity to make decisions about their own lives, yet we systematically ignore this reality in favor of compliance and control.
We dive deep into their concept of the "foul four"—the four devastating ways that imposing non-consensual rules damages children's relationships with themselves, their parents, problem-solving itself, and their understanding of how to navigate the world. From the arbitrary nature of bedtimes to the deeper psychological damage of forcing gratitude and politeness, this conversation will make you question every "because I said so" moment in your childhood and parenting. Whether you're a parent, educator, or simply someone interested in human flourishing, this episode offers a radically different lens through which to view childhood, autonomy, and what it means to raise great adults.
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