x

75% of people globally want unbiased news (Pew Research) but are concerned they're not getting that.

Get balanced coverage with Symby. See how stories are covered across diverse outlets and spot when one side covers a story the other skips.

PODCAST

Infinite Loops

Jim O"Shaughnessy

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!"

technology entrepreneurship

All Episodes

01:52:55

Michael Perry — Improbable Mentors and the Art of...

Infinite Loops ·

2025/11/06

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

en

01:25:34

Kenneth Stanley — The Trap of the Objective (EP.288)

Infinite Loops ·

2025/10/30

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

en

01:38:47

Elle Griffin — Rethinking Ownership and the Future of...

Infinite Loops ·

2025/10/23

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

en

01:23:53

Jay Yang — The Power of Permissionless Action (EP. 286)

Infinite Loops ·

2025/10/16

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

en

01:19:34

Jeff Bussgang — The Experimentation Machine (EP.285)

Infinite Loops ·

2025/10/09

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

en

01:37:43

Dan Wang — China, US and our Collective Future (EP.284)

Infinite Loops ·

2025/10/02

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

en

01:20:33

Alex Danco — Speeches and Spells for the Kings and...

Infinite Loops ·

2025/09/25

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 recommended

en

01:39:44

Sangeet Paul Choudary — AI and our System Reshuffle...

Infinite Loops ·

2025/09/18

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. For

en

01:34:25

Michael Dean — The Architecture of Essays (EP. 281)

Infinite Loops ·

2025/09/11

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

en

01:06:17

Roon — On Shape Rotators, AGI & Tenet (Infinite Loops...

Infinite Loops ·

2025/09/04

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

en

01:41:22

Gurwinder Bhogal's Guide to Modern Survival (Infinite...

Infinite Loops ·

2025/08/28

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

en

01:33:17

Joe Hudson — The Art of Accomplishment (EP. 280)

Infinite Loops ·

2025/08/21

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 with

en

01:31:19

Michael Gibson & Danielle Strachman — The 1517...

Infinite Loops ·

2025/08/14

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 other

en

01:45:24

Ed Latimore — The Art of Self-Transformation (EP.278)

Infinite Loops ·

2025/08/07

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, that’s

en

01:45:51

Sam Arbesman — Science, Complexity and Humanistic...

Infinite Loops ·

2025/07/31

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—from

en

01:19:49

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

Infinite Loops ·

2025/07/24

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 shares

en

01:24:56

Lawrence Yeo — The Inner Compass (EP.275)

Infinite Loops ·

2025/07/17

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

en

01:24:45

Will Storr—The Status Game (Infinite Loops CLASSICS)

Infinite Loops ·

2025/07/10

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

en

01:07:51

Rupert Sheldrake — On Scientism, Morphic...

Infinite Loops ·

2025/07/03

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

en

01:59:00

Aaron Stupple & Logan Chipkin — The Sovereign Child:...

Infinite Loops ·

2025/06/26

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

en

296 results

Similar Podcasts

Lead With AI

Tamara Nall

Linux in the Ham Shack

Black Sparrow Media

Data Engineering Podcast

Tobias Macey

Eye On A.I.

Craig S. Smith

Reflections

Livewire Labs