Infinite Loops

• Jeff Bussgang — The Experimentation Machine (EP.285)

  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 time of learning, how to distinguish 10X founders and 10X joiners, and why execution velocity matters more than tech moats in the age of AI. One of the most important things Jeff and I discuss is why discernment and taste may be the most valuable human skills of the future. I hope you enjoy this conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!," check out our Substack. Important Links: Flybridge Jeff’s Wikipedia Profile Jeff’s Website Jeff on LinkedIn Jeff’s Twitter Show Notes: AI and the Rise of the 10X Founder The HUNCH Framework for Product-Market Fit Hair-on-Fire Value Props vs. Vanity Metrics Head in the Clouds, Feet on the Ground The Kill Criteria The 3Ts That VCs Look For Creating Win-Win Outcomes: MongoDB What Makes a 10X Founder The Human Edge in the Age of AI Everybody is in Sales Who is a 10X Joiner? Emperor of the World: Jeff’s Two Rules for Humanity

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• Dan Wang — China, US and our Collective Future (EP.284)

  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 millionaires, giving him unique insight into both superpowers' pathologies. This conversation covers everything from why ribbon-cutting ceremonies matter for societal optimism to how lawyers morphed from deal-makers to obstructionists after the 1960s. We explore California's high-speed rail fiasco, the rebellion against NIMBYism, and Dan's prescription: America needs 20% more engineering, China needs 50% more lawyerly protections. Plus we discuss cognitive diversity, the Death Star versus the Rebel Alliance, and why we need synthesis. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack. Important Links: Personal Website X / Twitter LinkedIn Profile at the Hoover Institution Show Notes: The Engineering State vs. the Lawyerly Society America's Lost Building Culture China's Gilded Age & America's Progressive Era Solutions for America's Building Crisis An Oncoming Battle of Elites Becoming Pro Development A Vision for a New Housing Fund China's Challenges Who Has a Better Shot At Change? Rickover: The Grand American Builder Dan's Uncertain Forecast of China Looking Ahead to 2035 Dan As Emperor of the World  

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• Alex Danco — Speeches and Spells for the Kings and Priests (EP.283)

  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 rhetorical genius, authentic weirdos, America's hypomanic DNA, the unexpected similarities between American and Chinese culture, and why listeners who haven't read any recommended books after 10 episodes are wasting their time. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack. Important Links: Website Twitter Newsletter Show Notes: Alex’s New Gig A Civil War Between Elites The Citizen Kane Test for CEOs Communication is the Founder's Job VCs as Legitimacy Banks & Magic-Makers The Lost Art of Speechwriting Reagan's Genius & The American Dream The Hypomanic Edge Mystery, Respect, and Cultural Power Marketing Ideas to the Right Audience The New Internet Economy Maritime Laws for AI Agents The Goth Index and Authenticity Substack's Identity Crisis & The Role of Podcasts Alex as Emperor of the World (Again) Books Mentioned: What Works on Wall Street; by Jim O'Shaughnessy How Music Works; by David Byrne Breakneck: China’s Quest to Engineer the Future; by Dan Wang The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; John D. Gartner The Language of Magic; by Toby Chapel Underwriters of the United States: How Insurance Shaped the American Founding; by Hannah Farber  

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• Sangeet Paul Choudary — AI and our System Reshuffle (EP.282)

  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 world of cheap answers, and why our educational and career structures need complete reinvention rather than incremental reform. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack. Important Links: Reshuffle: Who Wins When AI Restacks the Knowledge Economy (Amazon) Website Twitter Substack LinkedIn Show Notes: Sangeet’s Core Thesis Technology's Second Order Effects Coordination Without Consensus Resistance to Innovation The Bottlenecks of Changing Systems Staying Above The Algorithm An Impending Cognitive Chasm The Limitations of Reskilling Redesigning Hiring for the AI Era The Human Touch Fallacy The End of Linear Career Paths Collective Sense-making in Uncertainty Sangeet as Emperor of the Day Books Mentioned: Platform Revolution; by Geoffrey G Parker, Marshall W Van Alstyne, Sangeet Paul Choudary Reshuffle; by Sangeet Paul Choudary The Hound of the Baskervilles; by Arthur Conan Doyle Why Greatness Cannot Be Planned; by Kenneth Stanley and Joel Lehman  

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• Michael Dean — The Architecture of Essays (EP.281)

  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-pattern framework that maps essays across Idea, Form, and Voice, and how to make craft teachable and AI feedback useful without replacing the writer. Along the way, we dive into architecture school critiques, why publishable doesn’t mean perfect, how editing rewires thinking, and the cultural risks if we keep treating writing as vibes instead of patterns. I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack. Important Links: Michael’s Website Substack X/Twitter Profile Show Notes: The Architecture of Essays: from Design School to Writing Frameworks The Pattern Language: Idea, Form, and Voice Local Nuance vs Global Stylekits Fundamentals before Breaking Rules: Joyce, Picasso, the Beatles Quality Without a Name Leveling the College Playing Field The Two Sandboxes of Fundamentals and Amplification Gamification, Play and Motivation Beyond the Five-paragraph Essay: Emerson and AI in Education Scoring Great Essays: Why David Foster Wallace takes Three Top Spots How Writing Colonized the brain Editing as Belief-rewiring: Why Writers Avoid It and Why Math Helps The King of Biases: Confirmation Bias Michael as Emperor of the World Books Mentioned: Works on Wall Street; Jim O’Shaughnessy Essay Architecture (in progress) ; by Michael Dean A Pattern Language; by Christopher Alexander The Best American Essays 2024 Anthology; by Wesley Morris and Kim Dana Kupperman Consider the Lobster; by David Foster Wallace The White Album; by Joan Didion Shooting an Elephant; by George Orwell Portrait of an Artist as a Young Man; by James Joyce Finnegan’s Wake; by James Joyce Towards a Golden Age; Paul Graham The Limits of Scientific Reasoning; by David Faust The WEIRDest People in the World; by Joseph Henrich    

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