Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)
Release Date: 11/06/2025
George Mack — The Game of Life (Infinite Loops CLASSICS)
Infinite Loops
Hello everyone, Jim here. We're taking a brief break from new episodes to spotlight a golden oldie from the Infinite Loops archive. This conversation from December 2023 remains one of my favorites. Fresh episodes return next week, but first, enjoy this conversation with the inimitable George Mack. _________________ Writer, marketer, entrepreneur, and master of mental models, George Mack returns to discuss the top 0.1% of ideas he’s ever come across, from treating life as a video game to spotting high-agency individuals. Important Links: (Rick and Morty) Show Notes: Treating Life...
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Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)
Infinite Loops
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...
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Kenneth Stanley — The Trap of the Objective (EP.288)
Infinite Loops
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"...
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Elle Griffin — Rethinking Ownership and the Future of Work (EP. 287)
Infinite Loops
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...
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Jay Yang — The Power of Permissionless Action (EP. 286)
Infinite Loops
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...
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Jeff Bussgang — The Experimentation Machine (EP.285)
Infinite Loops
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...
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Dan Wang — China, US and our Collective Future (EP.284)
Infinite Loops
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...
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Alex Danco — Speeches and Spells for the Kings and Priests (EP.283)
Infinite Loops
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...
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Sangeet Paul Choudary — AI and our System Reshuffle (EP.282)
Infinite Loops
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...
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Michael Dean — The Architecture of Essays (EP.281)
Infinite Loops
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...
info_outlineWhat 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
- 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