

Infinite Loops
Jim O'Shaughnessy
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!"
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!"
Episodes
Mentioned books

79 snips
Oct 16, 2025 • 1h 24min
Jay Yang — The Power of Permissionless Action (EP. 286)
Jay Yang, an author and creator focused on 'permissionless action,' challenges the conventional belief that you need permission to pursue your dreams. He shares his journey, from cold-emailing CEOs to landing impactful internships. Discussions revolve around building confidence through micro-actions, the importance of preparation over bravado, and how to rewire limiting beliefs. Yang emphasizes clarity of purpose as a motivator, the role of AI in accelerating progress, and using the TAG method to create no-brainer opportunities. His insights inspire listeners to take initiative and embrace curiosity.

136 snips
Oct 9, 2025 • 1h 20min
Jeff Bussgang — The Experimentation Machine (EP.285)
In this intriguing conversation, Jeff Bussgang, a venture capitalist and Harvard Business School professor, shares insights from his book, The Experimentation Machine. He discusses how AI is revolutionizing startups by compressing learning time and emphasizes the importance of execution velocity over mere technical advantages. Jeff introduces the concept of 10X founders and joiners, highlighting traits like judgment and a growth mindset. He also warns against being seduced by AI flattery, advocating for rigorous prompts to ensure critical thinking in AI interactions.

79 snips
Oct 2, 2025 • 1h 38min
Dan Wang — China, US and our Collective Future (EP.284)
Dan Wang, author of "Breakneck: China's Quest to Engineer the Future," shares his insights as a research fellow at the Hoover Institution. He discusses the stark contrast between China's engineering-driven growth and America's lawyer-dominated stagnation. The conversation dives into the consequences of legal obstructionism on U.S. infrastructure, the failures of California's high-speed rail, and the need for a cultural shift towards building. Dan argues both countries require significant adjustments: America needs more engineers, while China requires enhanced legal protections.

121 snips
Sep 25, 2025 • 1h 21min
Alex Danco — Speeches and Spells for the Kings and Priests (EP.283)
In this lively chat, Alex Danco, a communications expert and writer now with a16z, delves into the intricate dance between VCs and founders, whom he dubs the 'kings and priests' of tech. He emphasizes the need for founders to own their narratives and revives the lost art of speechwriting, referencing Reagan's rhetorical finesse. The discussion spans America's 'hypomanic DNA' and its surprising cultural parallels with China, culminating in a call for authenticity in communication and a warning against neglecting thoughtful reading.

161 snips
Sep 18, 2025 • 1h 40min
Sangeet Paul Choudary — AI and our System Reshuffle (EP.282)
Sangeet Paul Choudary, a bestselling author and senior fellow at UC Berkeley, dives into the profound impacts of AI on the economy. He argues that knowledge workers may soon find themselves 'below the algorithm,' with curiosity and judgment becoming rare commodities in a world of automated responses. Sangeet advocates for a complete overhaul of education and career structures, emphasizing the need for innovative hiring practices and collective sense-making to navigate systemic changes. His insights challenge conventional wisdom and provoke thought about our future.

198 snips
Sep 11, 2025 • 1h 34min
Michael Dean — The Architecture of Essays (EP.281)
Michael Dean, an architect-turned-writer and creator of Essay Architecture, delves into the hidden structures of nonfiction writing. He introduces his 27-pattern framework for essays, emphasizing how design principles can enhance writing. The conversation touches on the evolution from rigid formats to more innovative approaches, the role of AI in education, and the importance of blending traditional techniques with modern tools. Michael also advocates for personal expression and shares his insights on effective essay techniques and the significance of documenting thoughts for self-awareness.

77 snips
Sep 4, 2025 • 1h 6min
Roon — On Shape Rotators, AGI & Tenet (Infinite Loops CLASSICS)
In this engaging conversation, Roon, an AI researcher and techno-optimist, dives into the dynamic between 'shape rotators' and 'wordcels' in tech culture. He explores the potential futures of AGI, discussing concepts like Neuralink and simulation theory, and argues why Christopher Nolan's 'Tenet' is his best film. Roon emphasizes the importance of storytelling in conveying complex ideas and reflects on how AI intertwines with geopolitical realities, particularly Taiwan's semiconductor industry. His blend of humor and insight makes this a must-listen!

101 snips
Aug 28, 2025 • 1h 41min
Gurwinder Bhogal's Guide to Modern Survival (Infinite Loops CLASSICS)
Gurwinder Bhogal, an independent thinker focused on mental sovereignty, dives into how our modern world overwhelms our evolved social instincts. He discusses belief perseverance and its impact on society, emphasizing the need for integrity in activism. The dangers of misinformation and the rise of technology are explored, especially regarding critical thinking. Bhogal critiques gamification, warning against addictive behaviors while advocating for personal growth. Through engaging dialogues, he highlights the power of accountability and long-term thinking in reclaiming agency.

400 snips
Aug 21, 2025 • 1h 33min
Joe Hudson — The Art of Accomplishment (EP.280)
Joe Hudson, a coach to CEOs and founder of Art of Accomplishment, shares his unconventional journey from diverse careers to transformative coaching. He discusses his innovative three-center approach, bridging head, heart, and nervous system for personal development. Fear is explored as a catalyst for growth, and the conversation emphasizes the balance of logic and emotion in decision-making. Joe also delves into the importance of trust in coaching relationships and reflects on the impact of inherited wealth on identity and parenting.

105 snips
Aug 14, 2025 • 1h 31min
Michael Gibson & Danielle Strachman — The 1517 Rebellion (EP.279)
Michael Gibson, co-founder of the 1517 Fund and author of *Paper Belt on Fire*, along with Danielle Strachman, also a co-founder and advocate for dropouts, discuss their rebellion against traditional higher education. They challenge the idea that universities foster creativity, arguing that personal potential often trumps credentials. The duo explores nostalgia in innovation, critiques dystopian narratives, and emphasizes the need for cognitive diversity in entrepreneurship, promoting unique cultural expressions as essential for creative breakthroughs.