Infinite Loops

• Marc Dennis — Painting the Punchline (EP.293)

  Artist Marc Dennis joins Jim O'Shaughnessy to explore the intersection of hyper-realism, humor, and the "meta-narrative." Marc shares his incredible non-linear journey—from accidentally starting a forest fire at age seven to becoming a tenured professor and eventually betting it all to become a full-time artist with no plan B. They discuss why the "key to failure" is trying to please everyone, how humor acts as a survival mechanism, and the crucial difference between perception and reality. Marc also offers a masterclass on intention, explaining why he plants hidden stories within his paintings and sharing the profound realization that you cannot love others until you love yourself. This conversation is a deep dive into the creative mind, offering insights on resilience, identity, and the art of betting on yourself. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!", check out our Substack.   #Art #Creativity #Hyperrealism #Philosophy #MentalModels #Resilience #Humor #Psychology   Important Links: Substack: https://newsletter.osv.llc/ Marc's Website: http://www.marcdennis.com/ Marc's Instagram: https://www.instagram.com/darcmennis/ Books mentioned: Meditations by Marcus Aurelius The Twelve Caesars by Suetonius

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• Ariel Meyerowitz — Navigating the Art World (EP. 292)

  Professional art advisor Ariel Meyerowitz joins Jim O'Shaughnessy to demystify the complex world of art. Ariel provides an essential guide for aspiring collectors, explaining where to begin, how to develop your eye, and why buying what you love is the most important first step. They explore the inner workings of galleries, auctions, and art fairs, contrasting the emotional value of art with the often-fickle investment market. Ariel also shares her philosophy on patronage, the psychology of collecting, and the profound, stress-reducing impact of living with art. This conversation is a perfect starting point for anyone looking to break into the art world, offering a clear path from intimidation to appreciation. #Art #ArtCollecting #Investing #Culture #Creativity #MentalModels #Innovation #Design #Psychology #Philosophy   Important Links: Substack: https://newsletter.osv.llc/ Ariel's Website: https://www.arielmeyerowitz.com/   Books mentioned:  The Painted Word by Tom Wolfe

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• Adam Moskowitz — The Way of the Cheesemonger (EP.291)

  Adam Moskowitz is the King of Cheese—but his path to the throne was anything but straight. In this delicious episode of Infinite Loops, Adam shares his wild journey from a failed rap career and a battle with addiction to becoming one of the most influential figures in cheese and the host of A Cheese Course. Whether you are a foodie, a creator battling gatekeepers, or just someone who loves a good comeback story, this episode will remind you to bet on yourself—and maybe eat some better cheese while you're at it. 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. Show Notes: The "Cheese Quake" origin story and the failed rap career Why "Creamy" is a texture, not a flavor The Artisan Cheese Illuminati Creating a documentary when gatekeepers said "No" The "Olive Garden" insult that fueled a fire Is the "Banana on the Wall" actually art? Cognitive diversity and why echo chambers kill creativity The "Time Horizon is Infinite" philosophy Leaders Lead & Lead with Love Books & Ideas Mentioned: My Dinner with Andre (Movie) Candide by Voltaire (Dr. Pangloss) Kubla Khan by Samuel Taylor Coleridge Claude Shannon (Information Theory)

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• Todd Rose — Escaping the Trap of the Standard Path (EP.290)

  From a 0.9 GPA in rural Utah to the faculty of Harvard, Todd Rose's life is a testament to the idea that the "standard path" is a myth. In this return appearance on Infinite Loops, Todd opens up about the gritty, unvarnished reality of his origin story—a journey that includes ten minimum wage jobs, a stint administering enemas for a living, and the life-changing intervention of a department secretary named Marilyn Diamond. We dive deep into the "Dark Horse" mindset and why the pursuit of fulfillment, rather than the pursuit of excellence, is actually the most reliable driver of success. We also bond over our mutual disdain for Frederick Taylor, explore the devastating impact of "average-based" thinking on human potential, and discuss why dignity is the bedrock of a free society—illustrated by a heartbreaking personal encounter with a jar of chunky peanut butter. If you've ever felt like a square peg in a round hole, or if you're looking for a roadmap to navigate the coming cultural shifts in the age of AI, this conversation is essential listening. 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. Show Notes: The 0.9 GPA and the "Correct Answer Machine" Ten minimum wage jobs and the advice to "get longer gloves" Marilyn Diamond: The improbable mentor who saved Todd's education The "No Average Brain" discovery in neuroscience Why we both despise Frederick Taylor and Scientific Management Dark Horses: Ignoring the destination to find the path Degrees of Freedom: How Todd hacked the GRE The "Chunky Peanut Butter" story and the importance of dignity Resentment, trust, and the future of AI The "Rainy Day Club" and how paradigms actually shift Books Mentioned: Collective Illusions; Todd Rose The End of Average; Todd Rose Dark Horse; Todd Rose Improbable Mentors; Mike Perry The Principles of Scientific Management; Frederick Taylor The Structure of Scientific Revolutions; Thomas Kuhn The Wealth of Nations; Adam Smith Man's Search for Meaning; Viktor Frankl Dignity; Chris Arnade Capitalism, Socialism and Democracy; Joseph Schumpeter

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• George Mack — The Game of Life (Infinite Loops CLASSICS)

  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: George's Twitter The Lindy Library Roy: A Life Well Lived (Rick and Morty) How to Spot High Agency People The Mack Meditation What is ignored by the media — but will be studied by historians? The Early-Late Razor Show Notes: Treating Life as a Video Game Finding the Important Metrics Embrace Momentum; Embrace Constraints How to Spot High Agency People How to Increase Your Agency The Mack Meditation & Silence as Alpha Why Pessimism vs Optimism is the Wrong Debate The Future of Media What is Ignored by the Media but will be Studied by Historians? The Reddit to Facebook Continuum George's Most Midwit Opinion Randomness & Feeding the Algorithm How to Retain Curiosity George as Emperor of the World Books Mentioned: The Hypomanic Edge: The Link Between (a Little) Craziness and (a Lot Of) Success in America; by John Gartner Happy: Why More or Less Everything is Absolutely Fine; by Derren Brown What Works on Wall Street; by Jim O'Shaughnessy The Secret; by Rhonda Byrne Gödel, Escher, Bach: an Eternal Golden Braid; by Douglas Hofstadter The Beginning of Infinity: Explanations that Transform the World; by David Deutsch

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