Infinite Loops
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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Ariel Meyerowitz — Navigating the Art World (EP. 292)
<p>Professional art dealer 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...
Adam Moskowitz — The Way of the Cheesemonger (EP.291)
<p >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.</p> <p>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.</p> <p>I hope you...
Todd Rose — Escaping the Trap of the Standard Path (EP.290)
<p>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.</p> <p>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 dr...
George Mack — The Game of Life (Infinite Loops CLASSICS)
<p>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.</p> <p>_________________</p> <p>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.<br /> <br /> Important Links:</p> George's Twitter The Lindy Library Roy: A Life Well Lived (Rick and...
Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)
<p>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.</p> <p>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...
Kenneth Stanley — The Trap of the Objective (EP.288)
<p>Ken Stanley – AI researcher and author of "Why Greatness Cannot Be Planned" – joins me to explore why ambitious objectives can blind us to the stepping stones that make breakthroughs possible. Ken is the inventor of the novelty search algorithm and co-creator of Picbreeder, a crowdsourced evolutionary art experiment that has led to important insights about our objective-obsessed culture.</p> <p>This conversation covers everything from why vacuum tubes had to come before computers, how the path you take to success matters more than the success itself, the "fractured entangled representation" hypothesis, why grant applications kill innovation, how education beats the...
Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287)
<p>Writer, editor, and founder of The Elysian, Elle Griffin joins me on Infinite Loops to discuss her vision for participatory capitalism, a world where ownership, reputation, and creativity are shared more broadly across society.</p> <p>We explore the evolution of capitalism from the industrial era to the networked age, how broad-based ownership could rebuild the middle class, why optimism is revolutionary, and how storytelling shapes our collective imagination.</p> <p>We also discuss how reputation is becoming a new form of capital and how writers can become architects of meaning in a world reshaped by AI and automation...
Jay Yang — The Power of Permissionless Action (EP. 286)
<p>What if the biggest barrier between you and your dreams isn't talent, connections, or luck— but simply the belief that you need permission to act? Jay Yang joins Infinite Loops to challenge one of the most limiting assumptions of our time: that opportunities must be handed to us rather than created by us.</p> <p>At just 16, Jay cold-emailed the CEO of Beehiiv with a concrete plan that led to an internship. At 17, he sent Noah Kagan a 19-page audit of his email funnel with ready-to-ship assets, ultimately becoming head of content and helping put "Million Dollar Weekend" on th...
Jeff Bussgang — The Experimentation Machine (EP.285)
<p>Jeff Bussgang — entrepreneur, venture capitalist, Harvard Business School professor, and co-founder of Flybridge Capital — joins Infinite Loops to explore how AI is transforming the operating systems of startups.</p> <p>We dive into Jeff's framework from his new book The Experimentation Machine, why AI compresses the cost and time of learning, how to distinguish 10X founders and 10X joiners, and why execution velocity matters more than tech moats in the age of AI.</p> <p>One of the most important things Jeff and I discuss is why discernment and taste may be the most valuable human skills of the futu...
Dan Wang — China, US and our Collective Future (EP.284)
<p>Dan Wang, author of "Breakneck: China's Quest to Engineer the Future," joins me to explore why China builds while America blocks, how lawyers strangled U.S. infrastructure, and why Connecticut trains run slower than they did in 1914. Dan lived through China's trade war, Zero COVID, and the exodus of 15,000+ Chinese millionaires, giving him unique insight into both superpowers' pathologies.</p> <p>This conversation covers everything from why ribbon-cutting ceremonies matter for societal optimism to how lawyers morphed from deal-makers to obstructionists after the 1960s. We explore California's high-speed rail fiasco, the rebellion against NIMBYism, and Dan's prescription: America needs 20...
