

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
17 snips
Nov 27, 2025 • 1h 14min
Adam Moskowitz — The Way of the Cheesemonger (EP.291)
Adam Moskowitz, the King of cheese and host of A Cheese Course, shares his captivating journey from a failed rap career to becoming a leading figure in the artisan cheese world. He discusses how cheese reignited his purpose during recovery, the fascinating dynamics of American artisan cheesemaking, and the emotional connections people have with cheese. Adam emphasizes the importance of cognitive diversity in creativity and delves into the art of storytelling through cheese, all while tasting various delightful cheeses and sharing his innovative ventures.

122 snips
Nov 20, 2025 • 2h 4min
Todd Rose — Escaping the Trap of the Standard Path (EP.290)
Todd Rose, an author and former Harvard faculty member, shares his remarkable journey from a 0.9 GPA in rural Utah to championing individuality. He discusses the hazards of average-based thinking and the transformative influence of a mentor. Rose explores the 'Dark Horse' mindset, advocating for fulfillment over rigid success metrics. He critiques standardized institutions, emphasizing dignity and personal potential. The conversation also delves into the implications of AI on human values and the importance of embracing individuality in societal progress.

86 snips
Nov 13, 2025 • 1h 44min
George Mack — The Game of Life (Infinite Loops CLASSICS)
George Mack, a writer and marketer known for his insights on high-agency thinking, dives into the intriguing idea of treating life as a video game. He discusses how designing projects like game levels can boost motivation and reduce procrastination. George shares how to identify high-agency individuals and emphasizes that agency can be cultivated. He also explores the future of media and how overlooked trends may shape historical narratives. With a focus on curiosity and adapting to change, this conversation is a playbook for living intentionally.

39 snips
Nov 6, 2025 • 1h 53min
Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)
Michael Perry, a beloved Midwestern writer and volunteer firefighter, shares his incredible journey from farm kid to storyteller. He discusses the balance between blue-collar roots and literary aspirations, emphasizing the value of humility and practical wisdom. Perry recounts unforgettable tales, including his experience declining Oprah and selling books at firefighter conventions. He highlights the importance of kindness, adaptability in creativity, and the unique storytelling lessons learned from everyday encounters. Don't miss his humorous farm wisdom on avoiding sneezing cows!

111 snips
Oct 30, 2025 • 1h 26min
Kenneth Stanley — The Trap of the Objective (EP.288)
In this enlightening conversation, Kenneth Stanley, an AI researcher and author known for his work on novelty search, critiques the pitfalls of objective-driven innovation. He explains how unexpected discoveries often arise from serendipitous pathways rather than rigid goals. The discussion dives into the NEAT algorithm’s role in evolving complex neural networks and the insights gained from Picbreeder, a crowdsourced art project. Stanley also addresses the detrimental effects of traditional education on creativity and proposes a world free from constraining objectives.

78 snips
Oct 23, 2025 • 1h 39min
Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287)
Elle Griffin, writer and founder of The Elysian, dives into the concept of participatory capitalism, advocating for a future where ownership is more widely distributed. She argues that broad-based ownership can rebuild the middle class and explains how reputation has become a new form of capital. The conversation highlights innovative policies for employee ownership, the impact of AI and automation, and the necessity of optimistic narratives in storytelling. Griffin emphasizes the power of ownership to boost engagement and reshape workplaces for a better future.

98 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.

161 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.

135 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.


