Infinite Loops

In this episode of Infinite Loops, we sit down with venture capitalist and physicist Arkady Kulikov to explore the psychology behind founders, responsibility, and self-deception. Kulik discusses why the hardest problems in business are almost always human problems, how great founders deal with stress, and why the biggest lie entrepreneurs tell is often to themselves. He also explains how investors evaluate founder psychology, why difficult conversations are essential in business, and why resilience is more about adaptability than stubbornness. Important Links: Listen to our last conversation with Arkady here: https://www.infiniteloopspodcast.com/arkady-kulik-bridging-science-entrepreneurship-ep193/ Arkady's deep tech venture fund, rpv global: https://rpv.global/ 

In this episode of Infinite Loops, Jim O'Shaughnessy sits down with Angus Fletcher, Professor of Story Science at Ohio State University's Project Narrative and author of multiple books at the intersection of narrative theory, psychology, and brain science.  Angus' research challenges one of the most widely accepted ideas in modern culture: that the human brain works like a computer. Drawing on his work with U.S. Army Special Operations, he argues that humans think not in equations, but in actions and stories — and that modern education systems are failing to cultivate the kinds of intelligence needed to navigate the real world. Jim and Angus explore the difference between probability thinking and possibility thinking, why standardized education may be suppressing creativity, how stories shape strategy and leadership, and why the most successful innovators think like explorers rather than optimizers. Important Links: Read Angus' book — Primal Intelligence: The New Science of How We Think: https://www.amazon.com/Primal-Intelligence-New-Science-Think/dp/0593712974 Angus' Harvard Business Review Article — Your Brain Doesn't Work the Way You Think It Does: https://hbr.org/2025/01/your-brain-doesnt-work-the-way-you-think-it-does Learn more about Angus here: https://www.angusfletcher.co/

In this episode of Infinite Loops, we sit down with author Jonathan Tepper to discuss his extraordinary childhood. In 1985, when Jonathan was seven, his missionary parents moved the family to San Blas — then the heroin capital of Europe — to start a drug rehabilitation center. Jonathan and his brothers grew up alongside former bank robbers, prison survivors, and people living through the AIDS epidemic. These recovering addicts became like older siblings to them. What began with one man in a small apartment grew into a global movement operating in 20 countries. Jonathan's memoir, Shooting Up: A Memoir of Love, Loss, and Addiction, is out now and published in the US by Infinite Books and in the UK by Little, Brown Book Group. Important Links Buy Shooting Up: A Memoir of Love, Loss and Addiction: https://www.infinitebooks.com/books/products/shooting-up Read the first chapter for free: https://infiniteloops.substack.com/p/give-them-to-anyone-who-looks-like Learn more about Jonathan here: https://jonathan-tepper.com/

Fresh off releasing one of the most beautiful hardcover books we've ever seen, Paul Millerd returns alongside Infinite Books CEO Jimmy Soni for a deep dive into the broken incentives of traditional publishing, why the industry breeds "cynicism at scale," and how the internet is powering a second Renaissance for creators. We get into what it means to build a creative life on your own terms, the Taoist approach to growing an audience, how to navigate financial uncertainty while raising a family, and why seemingly boring daily routines fuel extraordinary creative work. 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: Paul's Website Paul's X Paul's Substack The Pathless Path Premium Hardcover Good Work Infinite Books Jimmy's X Show Notes: Make Books Beautiful Why Paul Turned Down Penguin Creative Work Should Inspire More Creative Work Cynicism at Scale in the Publishing Industry The Long Tail of Book Marketing Why Paul Launched a Hardcover Pathless Path Dre, Spielberg & Chappelle: Design Your Own System Playing Probabilistic Games How to Live a Pathless Life With a Family The Creative Perks of a Boring Life "What If I Do Less?" Books Are Win-Win Paul as World Emperor Books Mentioned: The Pathless Path: Imagining a New Story for Work and Life; by Paul Millerd Good Work: Reclaiming Your Inner Ambition; by Paul Millerd The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley; by Jimmy Soni What Works on Wall Street; by Jim O'Shaughnessy How to Retire Rich; by Jim O'Shaughnessy Walden (Steel Brothers reimagined edition); by Henry David Thoreau Why Greatness Cannot Be Planned: The Myth of the Objective; by Kenneth O. Stanley The Work Is the Win; by Billy Oppenheimer (forthcoming) Reclaim the Book; by Paul Millerd (essay) Tiny Experiments: How to Live Freely in a Goal-Obsessed World; by Anne-Laure Le Cunff The Chronic; by Dr. Dre (album) Tao Te Ching (Dao De Jing); by Lao Tzu  

Packy McCormick is one of the most thoughtful writers in tech and investing. In this episode of Infinite Loops, we talk about why writing is still the most powerful way to think clearly, how optimism becomes rational when you spend time with people actually building things, and what happens when the internet punishes you for being early and wrong.   Important Links: Packy McCormick on Optimism: https://www.notboring.co/p/optimism The Internet Contrarian: https://www.osam.com/pdfs/research/The%20Internet%20Contrarian.pdf Elliot Herschberg on GitLab Founder and Cancer: https://www.notboring.co/p/the-builder-cancer-problem Ben Thompson's Aggregation Theory: https://stratechery.com/aggregation-theory/  

What happens when you design a company assuming AI should do everything it possibly can?  Jean-Marc Daecius, OSV's Chief of Staff, joins Infinite Loops to explain what it means to be "AI first" — and why he believes he may be the company's last human chief of staff. The conversation explores how AI can remove meaningless cognitive load, protect deep work, and unlock creative leverage — from reshuffling priorities and filtering email, to reinventing publishing, agriculture, education, and even how we discover books, movies, and ideas.   Important links: Substack: https://newsletter.osv.llc/ Jean Marc's "The Future of Food": https://newsletter.osv.llc/p/the-future-of-food    

The Queens Night Market is one of New York City's most beloved institutions — but it was never supposed to last more than a year. John Wang, founder of the Queens Night Market, joins Infinite Loops to explain how a side project with a "terrible business model" unexpectedly became one of the most celebrated food markets in the world. From leaving a traditional legal career to imposing a strict price cap in one of the most expensive cities on earth, John shares how the market evolved into a cultural institution representing more than 100 countries through food.   Important links: Substack: https://newsletter.osv.llc/ Queens Night Market: https://queensnightmarket.com/  

Cliff Asness — co-founder, managing principal, and chief investment officer at AQR Capital Management — is one of the most influential quantitative investors of the last 30 years. He's also one of the most candid. In this conversation, Cliff joins Infinite Loops to talk about why losses hurt more than wins, how bubbles form, why modern investing increasingly resembles gambling, and what the dot-com era can teach us about today's markets.   Important links: Substack: https://newsletter.osv.llc/ Cliff's Perspectives: https://www.aqr.com/Insights/Perspectives Cliff's X: https://x.com/CliffordAsness  

Tomás Pueyo, the French-Spanish engineer and writer behind the successful "Uncharted Territories" Substack, joins us to dismantle the invisible forces that shape our history and future. We cover why humans are horrible at understanding exponential change, the geographical advantages of the U.S, why the Luddites might have been right, the "social media politician" of the future, why education is mostly signaling, and how air conditioning and mosquito eradication could change the destiny of nations.   Important Links: Tomas's Website X / Twitter LinkedIn Substack: Uncharted Territories YouTube Channel  

Annie Duke — former professional poker player, decision strategist, and bestselling author — joins us for a deep conversation about why smart people so often make bad decisions. Annie explains why misinterpretation is more dangerous than misinformation, why data is often true but misleading, and how our brains are wired for certainty in a probabilistic world. From real-world media examples to investing, health decisions, and AI-generated insights, this episode explores how explanations feel satisfying — even when they're wrong.   Important links: Substack: https://newsletter.osv.llc/ Annie's website: https://www.annieduke.com/  

Jimmy Soni, CEO and editor in chief of Infinite Books, is back on Infinite Loops. We discuss what's broken in traditional publishing and how we're fixing it. We also dig into Jimmy's forthcoming book on Kobe Bryant, why the world needs more "problem authors," and why our goal is to make our authors millionaires. We explore why most industries optimize for prestige instead of outcomes, how digital distribution has reshaped attention, and why authors — and creators more broadly — have more leverage than they realize. Important Links: Infinite Books: https://www.infinitebooks.com/ Jimmy's X: https://x.com/jimmyasoni Substack: https://newsletter.osv.llc/   Books Mentioned: The Founders by Jimmy Soni A Mind at Play by Jimmy Soni The Dao of Kobe by Jimmy Soni (Upcoming) What Works on Wall Street by Jim O'Shaughnessy Invest Like the Best by Jim O'Shaughnessy How to Retire Rich by Jim O'Shaughnessy The 4-Hour Workweek by Tim Ferriss The Almanac of Naval Ravikant by Eric Jorgenson (transcribed as "Naval Akan") Dispatches from Grief (Upcoming) Mamba Mentality by Kobe Bryant Slow Horses by Mick Herron The Boys in the Boat by Daniel James Brown

Happy Holidays! We're taking a short break from new episodes this week so you can focus on finishing that Christmas dinner. We'll be back next Thursday with something new. In the meantime, why not tuck into this conversation with Guy Spier from January 2024, which remains one of my favorites. Enjoy! _________________ Guy Spier runs the Aquamarine Fund, an "investment partnership closely modeled on the original Buffet Partnerships." He is also a podcast host, YouTube creator, author of The Education of a Value Investor and the host of the annual investment gathering VALUEx. He describes his life's project as "a quest for wealth, wisdom and enlightenment." Guy joins the show to discuss the differences between Switzerland and the US, how to unlock the British class system, what he learned from Warren Buffett, and MUCH more! Important Links: Guy's Website Guy's Twitter Guy's YouTube Channel 3Blue1Brown (YouTube Channel) Numberphile (YouTube Channel) Show Notes: The Differences Between New York, Switzerland & Paris Exploring the Dark Underbelly of New York Nightlife Psychedelics, Guns & Regulation The Advantages of Swiss Democracy Don't Short the United States The Branding Skill of the Royal Family Unlocking the Rules of the Class System Life Paths & Premeditation Luck, Opportunity & Non-Canonical Science Jim's Music Taste Mathematical Shenanigans Guy as Emperor of the World MORE! Books Mentioned: How to Change Your Mind: What the New Science of Psychedelics Teaches Us about Consciousness, Dying, Addiction, Depression, and Transcendence; by Michael Pollan The Hypomanic Edge: The Link Between (a Little) Craziness and (a Lot Of) Success in America; by John Gartner Write It Down, Make It Happen: Knowing What You Want and Getting It; by Henriette Anne Klauser Invest Like The Best; by Jim O'Shaughnessy Outside, the Sky is Blue: The story of a family told with searing honesty, humour and love; by Christina Patterson

What if the invention that truly made us human wasn't the wheel, language, or even agriculture — but art? In this episode of Infinite Loops, we sit down with internationally renowned artist Vik Muniz to explore a radical and deeply human idea: that art — the ability to represent the world — may be humanity's most important invention after fire. Born in São Paulo and now collected by major museums around the world, Muniz reflects on his own life journey — from growing up in a Brazilian favela to redefining what art can be — and explains why the artwork is only ever half complete. The viewer finishes it.   #Art #Creativity #VicMuniz #Perception #Photography #Innovation #Documentary #Mindset #VisualArt #InfiniteLoops   Important links: Substack: https://newsletter.osv.llc/ Vik's website: https://vikmuniz.net/  

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

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

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)

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

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

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  

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