

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

26 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!

87 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.

369 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.

35 snips
Aug 7, 2025 • 1h 45min
Ed Latimore — The Art of Self-Transformation (EP.278)
Ed Latimore, a boxer, physicist, and author, shares his insights on impulse control and self-forgiveness. He emphasizes the critical role of modern parenting, advocating for empathetic dialogue over authoritative methods. Latimore discusses the transformative power of social circles and the importance of being discerning rather than judgmental. He reflects on learning from adversity, the significance of self-talk, and how one's environment shapes personal growth, all while navigating complex societal issues.

58 snips
Jul 31, 2025 • 1h 46min
Sam Arbesman — Science, Complexity and Humanistic Computation (EP.277)
Sam Arbesman, a complexity scientist and author of "The Magic of Code," joins the discussion to explore the intricacies of our increasingly complex world. He delves into the value of oral traditions in preserving scientific knowledge and argues why cognitive diversity trumps demographic diversity. The conversation highlights the importance of humility in learning and the role of history in informing future technology. Sam also envisions the transformative potential of gaming in education and advocates for optimistic narratives in science fiction to inspire positive societal change.

78 snips
Jul 24, 2025 • 1h 20min
Nick Maggiulli — Climbing the Wealth Ladder (EP.276)
Nick Maggiulli, COO of Ritholtz Wealth Management and author of "The Wealth Ladder," dives into personal finance with a fresh perspective. He challenges financial myths and emphasizes that unusual results demand unusual actions. Discussion points include the importance of income over budgeting for wealth growth, the emotional aspects of wealth, and how happiness isn't guaranteed by riches. Nick also shares insights on navigating the complexities of wealth dynamics and the societal impacts of inherited fortunes, encouraging listeners to rethink their views on money.

138 snips
Jul 17, 2025 • 1h 25min
Lawrence Yeo — The Inner Compass (EP.275)
Lawrence Yeo, a writer, illustrator, and author of “The Inner Compass,” discusses the transformative power of intuition and self-understanding in a rapidly changing world. He emphasizes that embracing uncertainty cultivates curiosity and genuine personal insight. The conversation touches on how social conditioning veils our true desires and highlights the significance of journaling to enhance self-awareness. Plus, Yeo shares personal reflections on creativity, mistakes as learning opportunities, and fostering authentic connections through self-discovery.

99 snips
Jul 10, 2025 • 1h 25min
Will Storr—The Status Game (Infinite Loops CLASSICS)
In this engaging conversation, award-winning journalist Will Storr dives into his book 'The Status Game,' revealing how our quest for social status drives behavior. He discusses irrational beliefs shaped by personal narratives and the psychology behind status-seeking, including its ties to social media and cults. Storr also explores the complexities of humiliation, its impact on individuals and societies, and the importance of empathy in education—to counteract tribal instincts and promote understanding in an increasingly divided world.