Episodes

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 da...

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 w...

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 ...

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 ...

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 ...

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 bu...

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 beco...

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 ...

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 ...

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 ca...

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 novel...

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 socie...

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 assumption...

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. We dive into...

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 ...

It’s Alex Danco’s landmark 10th appearance on Infinite Loops! He joins the show to discuss his move from Shopify to a16z (where he'll be building out their editorial operations), the power dynamics between VCs and founders (t...

Sangeet Paul Choudary, bestselling author of Platform Revolution and Reshuffle , and senior fellow at UC Berkeley, joins the show to challenge the conventional wisdom about AI's impact on our economy. We explore why knowledge...

Michael Dean — architect-turned-writer, O’Shaughnessy Fellow, and creator of Essay Architecture — joins the show to explore the hidden structures beneath nonfiction and why essays, like buildings, can be designed with pattern...

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 bac...

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 bac...

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 f...

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...

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 an...

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 c...