
Advertise on podcast: Infinite Loops
Rating
4.6from
This podcast has
318 episodes
Language
EnglishPublisher
Jim O'ShaughnessyExplicit
Yes
Date created
2019/11/25
Latest episode
2026/04/23
Average duration
93 min.
Release period
8 days
Description
Every Thursday, join Jim O'Shaughnessy and his favorite people as they arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Visit our Substack at newsletter.osv.llc for full transcripts, highlights, weekly doses of timeless wisdom, and a bounty of other goodies designed to make you go, "Hmm that's interesting!"
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Podcast episodes
Check latest episodes from Infinite Loops podcast
Brian Potter - How to Fix America's Building Problem (Ep. 311)
2026/04/23
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.
Alex Petkas - What Ancient Greece Can Teach Us About AI and the Future (Ep. 310)
2026/04/16
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
Check out Alex's Youtube Channel: https://www.youtube.com/@costofglory
Alex's Twitter: https://x.com/costofglory
The Cost of Glory Substack: https://costofglory.substack.com/
Sam Arbesman - Why Future Belongs to Curious People (Ep. 309)
2026/04/09
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
Sam's Substack: https://arbesman.substack.com/about
Neal Stephenson's Innovation Starvation: https://www.wired.com/2011/10/stephenson-innovation-starvation/
David Deutsch's The Beginning of Infinity: https://www.thebeginningofinfinity.com/
Johnathan Bi - Why the Best Founders Might Need a Little Delusion (Ep. 308)
2026/04/02
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://www.youtube.com/@bi.johnathan
Johnathan's Substack: https://substack.com/@johnathanbi
Polina Pompliano - What Truly Drives Successful People (Ep. 307)
2026/03/26
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.amazon.com/Hidden-Genius-Thinking-Successful-People/dp/0593715604
More from Polina Pompliano — The Profile: https://theprofile.substack.com
Adam Mastroianni - Why Creativity Feels Like It's Dying (Ep. 306)
2026/03/19
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 the Decline of Deviance: https://www.experimental-history.com/p/the-decline-of-deviance
Slime Mold Time Mold: https://slimemoldtimemold.com/
Our Conversation with Julian Gough: https://newsletter.osv.llc/p/the-egg-and-the-rock-ep-249
Arkady Kulik - The Psychology of Self-Deception (Ep. 305)
2026/03/12
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/
Angus Fletcher - The Biggest Mistake We Made About Intelligence (Ep. 304)
2026/03/05
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/
Jonathan Tepper - Growing Up in the Heroin Capital of Europe (Ep. 303)
2026/02/26
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/
Paul Millerd & Jimmy Soni — The Creative Opportunities of a Boring Life (EP. 302)
2026/02/19
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 - How Writing Shapes Companies (Ep. 301)
2026/02/12
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/
Jean-Marc Daecius - The Last Human Chief of Staff (Ep. 300)
2026/02/05
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
John Wang - The Man Who Built The Queens Night Market (Ep. 299)
2026/01/29
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 - Surviving the Meme Stock Bubble (Ep. 298)
2026/01/22
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 — Explaining the World Through Geography, History and Data (EP. 297)
2026/01/15
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
Podcast reviews
Read Infinite Loops podcast reviews
MH1928 2024/04/26
Excellent
Thank You
javk777 2024/07/22
This guy is high
Take a breath.
derekva 2024/02/06
A unique standout show
Brilliant, interesting, inspiring, provocative, independent thought, out-of-the-box just the right amount, and entertaining enough without going into ...
alexrwheeler 2024/01/12
Great interviewer, great guests
Perfect mix of listening, asking great questions and letting the guests talk fully, all while subtly and tactfully adding his value. This guy is incre...
DaveNKait 2022/12/24
Psychedelics for chronic pain
Loved your interview with Brom! Started a newco developing psychedelic NCEs for chronic pain (Cacti Therapeutics) so especially appreciated the bit ab...
t.8 2023/08/29
Let the guests talk
Jim has really interesting people on but he talks far more than they do. Sometimes he barely let's them get more than a couple words in before startin...
Yoodleyou 2022/07/29
Such a gem of a show
Love most of the content and excellent guests. Jim can be a little preachy sometimes but with zero doubt he only means well for the world at large and...
AC4684 2022/07/16
Learning & Knowledge in every Episode
Great show! Jim & his guests teach me something new or a new way to think about the world in each episode. I highly recommend it.
Bsizzle 1 2022/04/18
Something a little different
This pod was on a recommended list of PODS to listen to. Let’s just say I’m glad I stumbled onto it. Host is excellent at letting guest speak and brin...
MitchCumstein6969 2022/04/23
Domineering
I’ve tried. I really have. The guests are top notch. However Jim dominates the conversation by asking 5 minute questions with multiple tangents then g...
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