Infinite Loops

David Gelles joins guest host Jimmy Soni to discuss his career covering business for The New York Times. They talk about his books - Mindful Work, The Man Who Broke Capitalism, and Dirtbag Billionaire - and the reporting behind major stories on Bernie Madoff, Jack Welch, Boeing's 737 Max crashes, and Patagonia's Yvon Chouinard.

David explains how he broke a front-page story five weeks into journalism school, how he convinced Bernie Madoff to grant him a prison interview, and his process for writing books while working full-time. They also discuss raising kids who read for hours every day...

Gretchen Rubin joins guest host and Infinite Books CEO Jimmy Soni to discuss her journey from Supreme Court clerk to bestselling author, the creative obsessions that shaped her career, and the daily habits that fuel her work.

They cover her transition from law to writing Power Money Fame Sex, why she often ends up writing the book before the proposal, the art of editing until the final hour (even during pass pages), her 5:30 AM writing routine, and why "know thyself" remains the foundation of all her books - from 40 Ways to Look at Winston Churchill to Life in...

Wall Street Journal columnist Ben Cohen joins guest host Jimmy Soni, CEO of Infinite Books, to explore the hidden art of making things better. They explore the hot hand phenomenon in basketball, why Moneyball shaped a generation of journalists, the peanut butter and jelly crisis in the Warriors locker room, why ASML is the most important company you've never heard of, the strange story of Driscoll's tastiest berries, and the troubled development of The Princess Bride.

Important Links:

Learn more about Ben here: https://www.wsj.com/news/author/ben-cohen

Read The Science...

AI is no longer just a tool creators use to make content faster. It is beginning to reshape the entire creator economy.

Revan Lazarus is the founder of Jamie, an AI platform for podcast networks and digital sales teams.

He joins Infinite Loops, guest-hosted by Nick Tawil, to discuss how AI is changing podcasting, media sales, audience analytics, creator monetization, brand deals, and the future of content itself.

Important Links:

Learn more about Jamie AI: https://www.jamie-ai.com/

What actually happens after you donate a bag of clothes? Most people assume it gets sold locally to someone in need, but the reality is much bigger, stranger, and more global.

In this episode of Infinite Loops, hosted by OSV's Nick Tawil, we sit down for a roundtable on the hidden global economy of secondhand textiles with Brian London, Marisa Adler, and Eric Stubin, all experts in the field. We discuss how the industry works, why fast fashion has made the problem harder, why 70% of the world uses secondhand clothing, what AI can and can't solve, and why turning...

Jason Buck, founder and CIO of Mutiny Funds, joins Infinite Loops to tell the painful and darkly funny story of how the 2007–2008 crash destroyed his real estate business, wiped out his paper wealth, and taught him one of the hardest lessons in markets: being right is not the same thing as making money.

Jason explains how he went from real estate developer to volatility trader and eventually built his philosophy around survival, resilience, and the "Cockroach Portfolio." He and Jim explore why true diversification always feels uncomfortable, why human behavior is the most persistent source of market mi...

Chelsea Follett joins Infinite Loops to explain why the "good old days" were far darker than most people imagine — and why progress should never be taken for granted.

Chelsea is the managing editor of Human Progress and author of Centers of Progress and the forthcoming The Grim Old Days. We discuss why humans are so drawn to nostalgia, what life was really like in the preindustrial past, why doomsday predictions keep failing, and how freedom, innovation, and open inquiry helped create the modern world.

Important Links:

Learn More about Chelsea's upcoming book here: ht...

Mykhailo Marynenko joins Infinite Loops for for a fascinating conversation about the future of AI, creative tools, privacy, and data ownership. 

From growing up in his father's phone repair shop in Ukraine to building experimental AI systems today, Mykhailo has spent his life taking things apart, figuring out how they work, and rebuilding them in unexpected ways. 

We explore how AI can help creators without replacing them, why privacy and data ownership matter, and what it means to design tools that give people more control over complex information.

Important Links

More ab...

On a February morning, Danielle Crittenden's world cleaved in two: the life before her daughter Miranda was found dead in her Brooklyn apartment, and the life after.

Two years and three months later, Danielle joins Infinite Loops to discuss her luminous memoir, Dispatches from Grief, which unflinchingly traces the strange afterlife of grief with precision, restraint, and unexpected humor.

This conversation explores what grief really feels like. With extraordinary honesty and grace, Danielle shares the physical pain, the loneliness of loss, and the slow work of carrying her daughter's memory forward. 

Dispatches from Grief is ou...

Saloni Dattani, author of the Scientific Discovery Substack and founding editor of Works in Progress magazine, joins Infinite Loops to discuss why medical innovation is often much slower than it needs to be.

We explore why so much research still begins in animal models, how poor data distorts our understanding of disease, why clinical trials are one of the biggest bottlenecks in medicine, and how better systems could help promising treatments reach patients faster.

Important Links:

Read more from Saloni here: https://worksinprogress.co/our-authors/saloni-dattani

And here: https://substack.com/@sa...

Why has America become so bad at building housing, infrastructure, and major projects?

Brian Potter, author of The Origins of Efficiency and writer of Construction Physics, explains why prefab housing keeps failing and why there are no easy fixes to America's building problem. We discuss Katerra, California's anti-growth turn, and the deeper logic behind local opposition to growth: concentrated harms and diffuse benefits.

Important Links:

Read Brian's newsletter Construction Physics here: https://www.construction-physics.com/

Read Brian's book The Origins of Efficiency here: https://press.stripe.com/origins-of-efficiency

Learn...

What can Aristotle, Plato, Prometheus, and the Greek city-states teach us about AI, innovation, and the future of human flourishing?

Alex Petkas joins the show to explore how old myths still matter in a world shaped by technology. We talk about Prometheus as the foundational myth of tech, Plato's fear that writing would become a tool for forgetting, the real lesson of Icarus, why decentralization creates cultural power, and what it means to remain fully human in the age of AI.

Important Links:

Learn More about The Cost of Glory: www.costofglory.com<...

Scientist and writer Sam Arbesman joins us for a wide-ranging conversation on AI, optimism, science, education, archives, science fiction, and why the history of computing still has so much to teach us.   We talk about why pessimism is often mistaken for sophistication, why AI may reward open-mindedness more than intelligence, why science works even though scientists are imperfect, and why the future may depend on revisiting forgotten ideas from the past.

Important Links:

Learn more about Sam here: https://arbesman.net/

Read Sam's latest book: https://www.hachettebookgroup.com/titles/samuel-arbesman/the-magic-of-code

S...

Johnathan Bi returns to Infinite Loops for a conversation about founders, delusion, America, religion, mysticism, and the strange tension between truth and action.

We explore why some of the most effective builders may be the least introspective, why societies often run on useful fictions, how America encourages megalomania, what happens when materialism starts to feel incomplete, and why the "seeker" may matter even more in the age of AI. The episode moves from Plato and Caesar to founders, mystics, near-death experiences, and the future of human creativity.

Important Links:

Johnathan's Youtube Channel: https...

Polina Pompliano studies some of the most successful people in the world—and what she's found challenges how we think about success, creativity, and human behavior.

In this episode of Infinite Loops, we explore the mental models behind high performers, why we misunderstand people (including ourselves), and what it really takes to see the world differently. From creativity and rationality to identity, media bias, and the hidden motivations driving success, this conversation is a deep dive into how great thinkers actually operate.

Important Links:

Check out Polina's new book: 

https://www.ama...

In this episode of Infinite Loops, we speak with Adam Mastroianni—experimental psychologist and sharp critic of modern culture and science. We ask, why does creativity feel like it's fading?

From endless remakes to cultural sameness, Adam argues that as society becomes more stable and risk-averse, we may be unintentionally reducing the "deviance" that drives originality and breakthrough thinking. We also discuss why science should get weirder, how to fight credentialism, and the dangers of professionalization.

Important Links:

To learn more about Adam Mastroianni: https://www.adammastroianni.com/

Adam's Piece on...

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...

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 navig...

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 L...

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...

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 G...

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...

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.

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/Cli...

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:

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/

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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/

Ji...

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!

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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...

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 comple...

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 yo...

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...

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...

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 dr...

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.

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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:

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...

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...

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 and automation...

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 th...

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 futu...

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 high-speed rail fiasco, the rebellion against NIMBYism, and Dan's prescription: America needs 20...