Michael Perry — Improbable Mentors and the Art of Midwestern Storytelling (EP. 289)
Release Date: 11/06/2025
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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