Infinite Loops

• Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)

  What happens when a shy farm kid from rural Wisconsin who never dreamed of being a writer becomes one of America's most beloved storytellers? Michael Perry joins Infinite Loops to share his remarkable journey from cleaning calf pens to pitching scripts at Universal Studios, all while maintaining his day job as a volunteer firefighter and EMT in his hometown. This conversation is a masterclass in authentic storytelling, practical wisdom, and the power of staying true to your roots while navigating an industry that often values credentials over character. Perry shares unforgettable stories about turning down Oprah (yes, really), why he sells hundreds of books to "people who don't read" at firefighter conventions, and how his nursing background taught him the most important skill for any writer: human assessment. We explore his philosophy of "kindness is not weakness," the difference between cash and cachet, and why sometimes the best career move is knowing when not to move at all. Whether you're a writer, entrepreneur, or simply someone who believes in the power of authentic storytelling, this episode will remind you that sometimes the best way forward is to embrace your own improbable path and never stand behind a sneezing cow. 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 Perry's website Substack - Michael Perry's Voice Mail Michael's X / Twitter LinkedIn Instagram Michael Perry's Mailing List Show Notes: Connections with Mark Twain The NFL Friend & First Investment Mark Twain's European Fame & American Diplomacy Blue Collar vs. Capital 'A' Art Flying Under the Radar Midwestern Wisdom & Family Stories Charity, Humility, & Fundamentalist Upbringing The Positive Side of Imposter Syndrome Happy Tangents vs. Detailed Blueprints Publishing Industry Frustrations EMT Requires Pulse & Driver's License The Oprah Story First Mover Disadvantage Brothers, Guns, & Material Sources Mortality & Perspective The Gimlet-Eyed Drive Visiting Tom The Reality of Writing Today Pragmatism & Adaptation Voltaire & Historical Perspective Mike as Emperor of the World Books Mentioned: A Tale of Two Cities; Charles Dickens Mark Twain; Ron Chernow Improbable Mentors and Happy Tangents; Michael Perry Population: 485; Michael Perry Visiting Tom; Michael Perry Truck: A Love Story; Michael Perry Million Billion; Michael Perry 40 Acres Deep; Michael Perry Montaigne in Barn Boots; Michael Perry The Peter Principle; Laurence J. Peter What Works on Wall Street; Jim O'Shaughnessy Invest Like the Best; Jim O'Shaughnessy How to Retire Rich; Jim O'Shaughnessy Greatness Cannot Be Planned; Ken Stanley The Bible All Quiet on the Western Front; Erich Maria Remarque Tao Te Ching; Laozi Gone With the Wind; Margaret Mitchell Serpico; Peter Maas Candide; Voltaire  

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• Kenneth Stanley — The Trap of the Objective (EP.288)

  Ken Stanley – AI researcher and author of "Why Greatness Cannot Be Planned" – joins me to explore why ambitious objectives can blind us to the stepping stones that make breakthroughs possible. Ken is the inventor of the novelty search algorithm and co-creator of Picbreeder, a crowdsourced evolutionary art experiment that has led to important insights about our objective-obsessed culture. This conversation covers everything from why vacuum tubes had to come before computers, how the path you take to success matters more than the success itself, the "fractured entangled representation" hypothesis, why grant applications kill innovation, how education beats the playground mentality out of children, and why "interesting" is the opposite of random. 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 Google Scholar Wikipedia Book: Why Greatness Cannot Be Planned Show Notes: Are We Deterministic Thinkers Living in a Probabilistic World? Evolving Complexity and the NEAT Algorithm The Origins of Picbreeder The Power of Novelty Search The Cultural Impact of Non-Objective Thinking Why Pursuing Interestingness is Not the Same as Being Random Mechanizing Serendipity via Stepping Stones The Allure of the Security Blanket The Omni-culture of NSF Funding What Makes an Innovator? The Fractured Entangled Representation Hypothesis What does it say about LLMs if They Are Fractured and Entangled? Path Dependency and Careers Ken as Emperor of the World Books Mentioned: Why Greatness Cannot Be Planned; by Kenneth Stanley (and Joel Lehman) The God Problem; by Howard Bloom The Lucifer Principle; by Howard Bloom Global Brain; by Howard Bloom The Beginning of Infinity; by David Deutsch Invest Like the Best; by Jim O'Shaughnessy A Mind At Play; by Jimmy Soni  

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• Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287)

  Writer, editor, and founder of The Elysian, Elle Griffin joins me on Infinite Loops to discuss her vision for participatory capitalism, a world where ownership, reputation, and creativity are shared more broadly across society. We explore the evolution of capitalism from the industrial era to the networked age, how broad-based ownership could rebuild the middle class, why optimism is revolutionary, and how storytelling shapes our collective imagination. We also discuss how reputation is becoming a new form of capital and how writers can become architects of meaning in a world reshaped by AI and automation. 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: The Elysian Elle Griffin on X (Twitter) LinkedIn Website Elle's Novel Obscurity Show Notes: The New GI Bill for Stock Ownership Rethinking ESOPs, RSUs, and Equity for All The Founder's Dilemma: Risk, Ownership & Exit Tax Incentives for Employee Ownership A Tale of Two Experiments The Ownership Czar for the Day The Future of Work The State with Baby Bonds The Problem with Worth and Deserving The Power of Utopian Fiction The Currency of Belief and Reputation Empress of the World Question Books and References Mentioned: Obscurity; by Elle Griffin The Elysian; by Elle Griffin The Beginning of Infinity; by David Deutsch The Lessons of History; by Will & Ariel Durant The History of Civilization; by Will & Ariel Durant Why Greatness Can't Be Planned; by Kenneth O. Stanley Looking Backward; by Edward Bellamy Herland; by Charlotte Perkins Gilman Les Misérables; by Victor Hugo Frankenstein; by Mary Shelley The Republic; by Plato Das Kapital; by Karl Marx The Count of Monte Cristo; by Alexandre Dumas 20,000 Leagues Under the Sea; by Jules Verne A Tale of Two Cities; by Charles Dickens White Mirror Stories; by Infinite Books    

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• Jay Yang — The Power of Permissionless Action (EP. 286)

  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, Jay cold-emailed the CEO of Beehiiv with a concrete plan that led to an internship. At 17, he sent Noah Kagan a 19-page audit of his email funnel with ready-to-ship assets, ultimately becoming head of content and helping put "Million Dollar Weekend" on the New York Times bestseller list. His secret? Understanding that preparation beats bravado, that most doors don't even have locks, and that the fastest way to get what you want is to do the work upfront and make saying "yes" a no-brainer for others. This conversation dives deep into Jay's philosophy of permissionless action, exploring why most people accept the "standard pace" when there's actually no speed limit, how to reprogram limiting beliefs through small wins, and why high agency people focus on outputs while low agency people get trapped tracking inputs. 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: Jay Yang's website Jay Yang's X Jay Yang's Instagram Jay Yang's Book, You Can Just Do Things Jay Yang's LinkedIn Show Notes: The Philosophy of Permissionless Action Breaking Free from Era-Defining Ideas Overcoming Limiting Beliefs Starting Small: Building Confidence Through Micro-Actions Inner vs. Outer Orientation Inputs vs. Outputs: The Agency Divide Failure as Feedback The Power of Persistence Curiosity and Cognitive Diversity AI and the Future of Work The Busy-ness Trap Signal vs. Noise in the AI Era People You Learn From Don't Have Huge Following The TAG Method Explained The New Way of Hiring Learning from the Greats Motivation vs. Clarity Jay's North Star and Anti-Goals Viktor Frankl and Finding Your Why Working in Public The Second Book Preview The Emperor Question Closing & Contact Information Books Mentioned: You Can Just Do Things: The Power of Permissionless Actions (Jay Yang) Million Dollar Weekend by Noah Kagan The Tao of Kobe (forthcoming 2026, Jimmy Soni) Greatness Cannot Be Planned (Ken Stanley) Man's Search for Meaning (Viktor Frankl)  

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• 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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