Infinite Loops

Updated: 16 Oct 2025 • 291 episodes
infiniteloopspodcast.com

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!"

Show episodes

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. At just 16, J

83 min
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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 Jeff’s framework from his new book The Experimentation Machine, why AI compresses the cost and

79 min
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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 mil

97 min
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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 (the kings and priests of our era), communication theory and the power of speechwriting, Reagan's

80 min
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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 workers risk falling "below the algorithm," how curiosity and judgment become luxury goods in a

99 min
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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 patterns rather than left to inspiration. We discuss the origins of Essay Architecture, Michael’s 27-p

94 min
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