Episodes

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 wh...

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 fulfil...

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...

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 navigati...

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 tak...

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 becomi...

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, ultimat...

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 Jef...

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...

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 recommende...

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...

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 ar...

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to November 2023, when we welcomed the one and only Roon. _________________ AI researcher, memelord extraordinaire, and techno-optimist Roon joins the show to discuss coming up with the shape rotator vs. w...

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to August 2024, when we welcomed the one and only Gurwinder Bhogal. _________________ “We have created for ourselves a world that we didn't evolve for.” Gurwinder Bhogal is, for my money, one of the most i...

What happens when a self-described "not very good" venture capitalist discovers he has an extraordinary gift for coaching the world's most successful CEOs? Joe Hudson joins Infinite Loops to share his unconventional journey from Alaska fishing boats to Hollywood directing to Silicon Valley boardrooms, ultimately finding his calling in helping high-performers unlock their deepest potential. This conversation dives deep into Joe's revolutionary three-center approach to human development—working w...

Michael Gibson and Danielle Strachman, co-founders of 1517 Fund, join the show to discuss their rebellion against higher education, why universities stifle creativity, why IQ doesn't correlate with innovation, and how betting on "misfit toys" is the way to go—plus we explore Girardian mimesis, the perishable nature of creativity, the laziness of pessimistic storytelling and MORE! I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of o...

Ed Latimore: boxer, physicist, and author of Hard Lessons from the Hurt Business makes his third appearance on the show to discuss hard-won wisdom about impulse control, self-forgiveness, the challenges of modern parenting and why being discerning (not judgmental) about your social circle might be the simplest rule for a better life. 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, tha...

Sam Arbesman, complexity scientist, author of "The Magic of Code," and scientist in residence at Lux Capital, joins me for a wide-ranging exploration of how we navigate an increasingly complex world that often exceeds human comprehension. We dive into the oral traditions that preserve crucial scientific knowledge, why cognitive diversity trumps demographic diversity, the forgotten innovations hiding in technological history, and Sam's vision for "Maxis 2.0". This conversation had everything—fr...

Nick Maggiulli, data scientist turned financial writer and COO of Ritholtz Wealth Management, joins me to discuss his latest book,The Wealth Ladder, which presents a six-level framework for building and managing wealth. Warning: this episode will upend what you think you know about money. We explore why atypical results require atypical actions, how income and not budgeting is the real unlock for wealth mobility, and how many financial myths persist simply because they feel good. Nick also shar...

Lawrence Yeo — writer, illustrator and author of “The Inner Compass” — joins the show to discuss the power of intuition in an uncertain world. We explore why embracing uncertainty leads to greater curiosity, how social conditioning pulls us away from our true north, why doing things for their own sake builds authentic conviction and how journaling the "whys" rather than the "whats" can transform your self-awareness. This conversation flowed so naturally we jumped right in without a formal intr...

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, here's my September 2022 chat with the always interesting Will Storr. _________________ Will Storr is an award winning journalist and author. His book ‘The Status Game’ transforms our understanding of human nature by demonstrating how our un...

Hello everyone, Jim here. We're taking a brief two-week break from new episodes to spotlight a couple of golden oldies from the Infinite Loops archive. Years later, these remain some of my favorite conversations. We’ll be back soon with fresh episodes, but in the meantime, enjoy this trip back to February 2024, when we welcomed the one and only Rupert Sheldrake. _________________ Rupert Sheldrake is a biologist and author of 9 books and over 100 scientific papers. A critic of what he sees as the...

What if everything we think we know about raising children is not just wrong, but actively harmful? Aaron Stupple and Logan Chipkin, authors of "The Sovereign Child," join Infinite Loops to make a case so compelling and radical that it challenges the very foundation of modern parenting and education. From birth, we're told that children need rules, structure, and authority to thrive. But what if this approach is crushing their natural creativity, problem-solving abilities, and authentic self-de...

Nadia Asparouhova, author of "Antimemetics: Why Some Ideas Resist Spreading," joins me for a fascinating exploration of why some ideas go viral while others—often the most important ones—resist transmission entirely. We dive into antimemes, Curtis Yarvin's journey from being canceled to becoming mainstream, St. Paul as history's ultimate memetic engineer, and why "Don't Mess with Texas" became a masterpiece of viral messaging. Plus her current research on advanced meditation techniques, interne...