Jim O'Shaughnessy

Infinite Loops

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!"

Author

Jim O'Shaughnessy

Category

Technology

Podcast website

infiniteloopspodcast.com

Latest episode

Jul 9, 2026

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Episodes

Nick Maggiulli — Climbing the Wealth Ladder (EP.276) 24.07.2025

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 fo...

Lawrence Yeo — The Inner Compass (EP.275) 17.07.2025

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 y...

Will Storr—The Status Game (Infinite Loops CLASSICS) 10.07.2025

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 autho...

Rupert Sheldrake — On Scientism, Morphic Resonance and the Extended Mind (Infinite Loops CLASSICS) 03.07.2025

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...

Aaron Stupple & Logan Chipkin — The Sovereign Child: Liberating Kids from the Tyranny of Rules 26.06.2025

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 t...

Nadia Asparouhova — An Antimemetic Rollercoaster 19.06.2025

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 m...

Miyoba Hamuhuma and Israel Balogun — Grassroots Solutions for Africa's Impoverished Youth (EP.272) 12.06.2025

I'm joined today by two remarkable men I met through the O'Shaughnessy Fellowships and Grants program. Israel Balogun was homeless and illiterate until the age of 22. Now, he leads a Nigerian youth rehabilitation nonprofit for street kids and is building a self-sustaining village for 200 out-of-school children with the support of an OSV Fellowship. Miyoba Hamuhuma lost both parents by 12 and battl...

Dr. Diane Hennacy Powell — Speculations in Post-Materialism (EP.271) 05.06.2025

Dr. Diane Hennacy Powell, neuropsychiatrist and author of "The ESP Enigma," joins me for a mind-bending exploration of consciousness, savant abilities, and the limitations of materialist science. Trained at Johns Hopkins under a neurologist-turned-psychiatrist, Diane has spent decades investigating phenomena that challenge our fundamental assumptions about how the brain works. We dive deep into wh...

Todd Rose — Are We Living in the Truman Show? (EP.270) 29.05.2025

Todd Rose, co-founder and CEO of Populace and author of books including "Collective Illusions" and "The End of Average," joins the show to discuss the science behind collective illusions and their impact on society. We explore why so many Americans self-silence, the dangers of conformity, and how one person can spark change. Todd and I are simpatico on… pretty much everything! So this was a fun on...

Charles Beames — Welcome to the Second Space Race (EP.269) 22.05.2025

Aerospace investor and York Space Systems chairman Chuck Beames joins me for a fascinating discussion on the commercial space revolution and the future of satellite security. A retired Air Force colonel with over 20 years experience as a space and intelligence officer, Chuck brings unparalleled expertise to our conversation about what many are calling "the second space race". We explore how Americ...

Natasha Joukovsky — On Recursion, Status Games & Manufactured Nonchalance (EP.268) 15.05.2025

Strategy consultant turned writer Natasha Joukovsky joins me to discuss why bourgeois comfort is more conducive to writing than you think, why choice-plots make for better fiction, the eyerolling prevalence of manufactured nonchalance, our shared distaste for Atlantis Bahamas, and MUCH more! I hope you enjoy this conversation as much as I did. For the full transcript, episode takeaways, and bucket...

Tiago Forte — Unlocking the Power of the Annual Review (Ep. 267) 08.05.2025

I've said before that one of the best parts of hosting Infinite Loops is the chance to connect with people who consistently make me think differently — and few do that quite like Tiago Forte. Tiago Forte joins Infinite Loops for the first time, and within minutes we closed the door on his best-selling "Building A Second Brain" and were off to the races: from digitizing 50,000+ words of personal da...

Nir Eyal — The Psychology of Addictive Products (EP.266) 01.05.2025

Author, speaker, founder, investor and behavioral design maestro Nir Eyal joins me for his second appearance on the show. Today, we dig into Nir's first book, "Hooked: How to Build Habit-Forming Products." We also discuss the difference between coercion and persuasion, AI's use case as our personal Jiminy Cricket and MUCH more! I hope you enjoy this conversation as much as I did. For the full tran...

Nathan Baschez — On AI Writing, Thought Design & Solo Foundership (EP.265) 24.04.2025

Nathan Baschez is the cofounder and CEO of Lex, an AI word-processor. He also cofounded Every, was the first employee at Substack AND co-created Product Hunt. Suffice to say, Nathan knows a thing or two about building on the internet. He joins the show to discuss how AI is changing writing, why it's time to rethink the article, the rise of solo founders and MUCH more. I hope you enjoy this convers...

Tommy Potter — Building the CIA for Entrepreneurs (EP.264) 17.04.2025

Young, polymathic, and full of energy — Tommy Potter is on a quest to build a "CIA for Entrepreneurs." He calls it "The Power Hour" — a startup community in Michigan that hosts dropouts, undergrads and PhDs across many industries: enterprise, consumer, CPG, aviation, gaming, robotics and AR/VR, as they work together to build cool projects. I had a great time chatting with Tommy as we spoke about n...

Alex Danco — On Strollers, Slop & Citizen Kane (EP.263) 10.04.2025

Shopify Product Director Alex Danco returns for his NINTH appearance on the show — and he comes in hot. As you'll hear, I didn't even get a chance to introduce him before he launched into his take on what everyone gets wrong about Citizen Kane. We also unpack the performance art of parenting, why dinner parties are the new status signals, the difference between meme and slop culture and MUCH more....

Vizi Andrei — The Way of the Tinkerer (EP.262) 03.04.2025

My guest today is my former teammate Vizi Andrei, founder of The Sovereign Artist program and author of Sovereign Artist: Meditations on Lifestyle Design . Vizi's journey has been anything but conventional. After dabbling in various creative projects, he realized that the internet offers a unique opportunity: the freedom to take countless small risks without catastrophic consequences. He built The...

Barry Ritholtz — Make Fewer Errors, Make More Money (EP.261) 27.03.2025

My friend Barry Ritholtz has spent his career being an astute market observer, investigating behavioral finance and data analytics. He runs Ritholtz Wealth Management which has been named ETF Advisor of the Year, Financial Times Top 300 Advisors, and one of America's fastest-growing RIAs. He's also the host of Masters in Business , Bloomberg Radio's most popular podcast (50+ million streams/downlo...

Jason Carman — Filmmaking at the Frontier (EP.260) 20.03.2025

The relentlessly prolific Jason Carman is making the films our culture needs: optimistic, inspiring and positioned at the frontiers of modern tech and science. In under two years, he has shipped more than 70 high-quality mini-documentaries exploring the startups shaping the future, racking up over 130,000 YouTube subscribers along the way. His new venture, Story Company, premiered "New Space", its...

Anne-Laure Le Cunff — Experiment Your Way to a Better Life (EP.259) 13.03.2025

My guest today is Anne-Laure Le Cunff, founder of Ness Labs and author of Tiny Experiments: How to Live Freely in a Goal-Obsessed World . On paper, Anne-Laure had it all: top grades, a high-flying job at Google, and a life that seemed to hit all the markers of success. But something was off. No matter how "traditionally" successful she became, she felt… "empty." So, she decided to do something abo...

Gabriel Kennedy — The Life and Thought Crimes of Robert Anton Wilson (EP.258) 06.03.2025

If you've heard me speak for more than five minutes you've probably caught me dropping a Robert Anton Wilson reference (or several). Wilson is one of the most interesting (and underappreciated) writers I've ever come across — a Nostradamus for modern times. I was delighted to sit down with Gabriel Kennedy, author of the excellent biography Chapel Perilous: The Life and Thought Crimes of Robert Ant...

The Art of Retirement — Christine Benz (EP.257) 27.02.2025

Christine Benz is the Director of Personal Finance and Retirement Planning at Morningstar, where she has spent over three decades helping investors navigate the complexities of financial planning. She is also the author of "How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement" and serves as the president of the John C. Bogle Center for Financial Literacy. Before focusing on re...

Luke Fehily — Ireland's Innovation Playbook (EP.256) 20.02.2025

Luke Fehily is the Director of Innovation Policy at Progress Ireland — an independent think tank backed by the likes of the Collison brothers — that's on a mission to connect Ireland to proven policy solutions from around the world. Before joining Progress Ireland, Luke cut his teeth in both public and private sectors, developing a unique perspective on how to navigate bureaucratic challenges whil...

Rudy Havenstein — How to Fix America's Accountability Crisis (EP.255) 13.02.2025

Rudy Havenstein is a writer and satirist known for his sharp critiques of America's sprawling institutions and the elites who run them. He joins the show to discuss the accountability crisis in America — how it manifests across political life and, most importantly, what we can do to fix it. Important Links: Rudy's Twitter Rudy's Substack Show Notes: Why we should fear hyperinflation "The Fed is Co...

Mark Daniel — How to Find a Kaleidoscopic Alien (EP.254) 06.02.2025

Mark Daniel is the co-founder and managing partner of the investment firm Digital, whose portfolio extends across accelerated computing, gaming, crypto, social networking, AI, extended reality, cybersecurity, creator tools, spatial computing, and immersive learning. Back in 2013, he was also one of the very first recipients of a Thiel Fellowship. This was a fun one. Mark joins the show to discuss...

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