Infinite Loops

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Jim O'Shaughnessy
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#175 in Technology Business Entrepreneurship Education Society & Culture
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3.4K - 5.7K listeners Neutral 4.6 rating 228 reviews 266 episodes USA
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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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Recent Hosts, Guests & Topics

Here's a quick summary of the last 5 episodes on Infinite Loops.

Hosts

Jim O'Shaughnessy

Previous Guests

Alex Danco
Alex Danco is a Product Director at Shopify, known for his insightful commentary on culture and technology. He has made multiple appearances on the podcast 'Infinite Loops', where he discusses various topics ranging from parenting to cultural phenomena. Danco is also a writer and has contributed to discussions on meme culture and societal trends through his Substack and other platforms.
Vizi Andrei
Vizi Andrei is a creative entrepreneur and the founder of The Sovereign Artist program. He is the author of 'Sovereign Artist: Meditations on Lifestyle Design'. Vizi's journey has been marked by a diverse range of creative projects, leading him to recognize the unique opportunities presented by the internet. He advocates for stepping away from toxic hustle culture to embrace a lifestyle rooted in creativity, deep work, and sacred leisure. His insights focus on slow living, the dangers of unrealistic success benchmarks, and the importance of creative freedom.
Barry Ritholtz
Barry Ritholtz is a prominent market observer and the founder of Ritholtz Wealth Management, which has received accolades such as ETF Advisor of the Year and recognition as one of America's fastest-growing RIAs. He is also the host of 'Masters in Business,' a highly popular podcast on Bloomberg Radio with over 50 million streams/downloads. Ritholtz has a strong background in behavioral finance and data analytics, and his new book, 'How Not To Invest,' focuses on avoiding common investing mistakes to improve financial outcomes. He is known for blending engaging storytelling with data-driven insights.
Jason Carman
Jason Carman is a prolific filmmaker known for creating optimistic and inspiring films that explore the frontiers of modern technology and science. In less than two years, he has produced over 70 high-quality mini-documentaries that delve into startups shaping the future, amassing more than 130,000 subscribers on YouTube. His latest venture, Story Company, premiered 'New Space', a comprehensive exploration of the modern space industry, to a full theater in San Francisco. With multiple projects underway, including a full-length sci-fi feature, Carman aims to redefine the genre for the 21st century. He was awarded the $100k O'Shaughnessy Fellowship for his ambition and filmmaking skills.
Anne-Laure Le Cunff
Anne-Laure Le Cunff is the founder of Ness Labs and the author of 'Tiny Experiments: How to Live Freely in a Goal-Obsessed World.' She holds a PhD in neuroscience and has over 100,000 newsletter subscribers. Previously, she worked at Google and has developed a new model of success centered around conducting tiny experiments to create a fulfilling life on her own terms.

Topics Discussed

Citizen Kane performance art of parenting dinner parties status signals meme culture slop culture Vizi Andrei The Sovereign Artist lifestyle design slow living hustle culture creative freedom experimentation productivity myths behavioral finance data analytics investing financial advisor market psychology rookie mistakes financial innovations filmmaking optimism technology science mini-documentaries space industry sci-fi films O'Shaughnessy Fellowship tiny experiments neuroscience productivity culture cognitive scripts model of success goal-obsessed world
Episodes

Here's the recent few episodes on Infinite Loops.

0:00 1:42:14

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

Hosts
Jim O'Shaughnessy
Guests
Alex Danco
Keywords
Citizen Kane performance art of parenting dinner parties status signals meme culture slop culture

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.

Unsurprisingly, this was a fun one. 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:

Show Notes:

  • What EVERYONE gets wrong about Citizen Kane
  • Jim’s hardest interview question
  • Elon & Lutnick: clash of the cartoons
  • The status hierarchy of baby strollers
  • What happened to Yuval Noah Harari? (With a diversion via digital girlfriends and North Korean crypto hackers)
  • Dinner parties as status signals
  • Parenting as performative art
  • History’s greatest memers
  • Infinite Jest: the sequel (an Alex Danco & Jim O’Shaughnessy production)
  • GIF culture vs AI slop
  • From “code is capital” to “code is labour”
  • “Did I mention that I dropped out of Stamford?”
  • From Clint Eastwood to Cloud Atlas
  • MORE!

Books, Articles & Films Mentioned:

  • Two Thoughts: A Timeless Collection of Infinite Wisdom; by Jim O'Shaughnessy and Vatsal Kaushik
  • Finnegans Wake; by James Joyce
  • Invest Like the Best; by Jim O'Shaughnessy
  • Sapiens: A Brief History of Humankind; by Yuval Noah Harari
  • Underwriters of the United States: How Insurance Shaped the American Founding; by Hannah Farber
  • The Magic Mountain; by Thomas Mann
  • The Gervais Principle; by Venkatesh Rao
  • Scarcity & Abundance in 2025; by Alex Danco
  • Cloud Atlas; by David Mitchell
  • Citizen Kane; directed by Orson Welles
  • F for Fake; directed by Orson Welles
  • My Dinner with Andre; directed by Louis Malle
  • Letters from Iwo Jima; directed by Clint Eastwood
  • Million Dollar Baby; directed by Clint Eastwood
  • Fawlty Towers (TV show)
  • Absolutely Fabulous (TV Show)

0:00 1:20:09

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

Hosts
Jim O'Shaughnessy
Guests
Vizi Andrei
Keywords
Vizi Andrei The Sovereign Artist lifestyle design slow living hustle culture creative freedom experimentation productivity myths

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 Sovereign Artist program to help creators step away from the toxic hustle culture and build sustainable, meaningful lives rooted in creativity, deep work, and sacred leisure. His insights into Slow Living, the Sicilian Dream, and embracing experimentation over optimization can help one break free from comparison traps.

He joins me to discuss the dangers of chasing unrealistic benchmarks of success, the myths of modern productivity, how to unlock creative freedom, and MUCH more!

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:

Show Notes:

  • Is procrastination a signal for something bigger?
  • The Sicilian Dream: challenging the hustle culture
  • The Pursuit of Busyness
  • The rise of the pseudo-entrepreneur
  • Are we taking the internet for granted?
  • The outlier obsession can kill your creative potential
  • Are your goals your own? or borrowed from prepackaged societal narratives?
  • Drunk with too many choices
  • Crossing the bridge of nihilism
  • The art of boredom: slow living might just be the answer
  • Knowledge is existential; energy is everything
  • MORE!

Books Mentioned:

  • Sovereign Artist: Meditations on Lifestyle Design; by Vizi Andrei
  • The Pathless Path: Imagining a New Story for Work and Life; by Paul Millerd
  • Status Anxiety; by Alain de Botton
  • The Soul of the World; by Roger Scruton
  • Escolios to an Implicit Text; by Nicolás Gómez Dávila
  • Antifragile: Things That Gain from Disorder; by Nassim Taleb
  • The Infinity of Lists; by Umberto Eco
  • The Myth of the Eternal Return; by Mircea Eliade
  • Happy: Why More or Less Everything is Absolutely Fine; by Derren Brown

0:00 1:27:53

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

Hosts
Jim O'Shaughnessy
Guests
Barry Ritholtz
Keywords
behavioral finance data analytics investing financial advisor market psychology rookie mistakes financial innovations

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/downloads), which he started way back in 2014.

In his new book, How Not To Invest, Barry emphasizes how avoiding rookie mistakes can significantly help you do better financially. He blends engaging stories with data-driven insights, and explores overlooked aspects of behavioral finance, psychology and the market. Reading his book is like having a casual drink with an experienced, wise, and honest friend.

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:

Show Notes:

  • How Amateurs Win
  • Managing Emotions When the Market Goes Down
  • If You Can't Afford a Financial Advisor Yet…
  • Notable Financial Innovations
  • Barry’s Transition from a Trader to an Investor
  • Varieties of Investor Personas
  • What To Do When Randomness Derails Your Plans
  • Finding Your Own Maintainable Processes
  • Having Reliable Information Sources
  • Barry As World Emperor

Books Mentioned:

  • How Not to Invest: The Ideas, Numbers, and Behaviors That Destroy Wealth - And How to Avoid Them; by Barry Ritholtz
  • Winning the Loser’s Game; by Charley Ellis
  • How We Know What Isn't So: The Fallibility of Human Reason in Everyday Life; by Thomas Gilovich

0:00 1:45:39

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

Hosts
Jim O'Shaughnessy
Guests
Jason Carman
Keywords
filmmaking optimism technology science mini-documentaries space industry sci-fi films O'Shaughnessy Fellowship

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 100+ minute-long exploration of the modern space industry, to a packed San Francisco theater this year. Story Company has multiple projects in the pipeline, including a full-length sci-fi feature. Ultimately, he intends to create a new generation of sci-fi films: a Star Wars for the 21st century.

I love Jason’s ambition, drive and enthusiasm (not to mention his filmmaking chops), which is why we awarded him a $100k O’Shaughnessy Fellowship last year.

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:

Show Notes:

  • How Jason fell in love with filmmaking
  • Laziness as an edge
  • How to build a good team
  • How to fix Hollywood
  • Frontier Films: a new category of movie
  • From science-fact to science-fiction
  • Finding the right infinite loops
  • The roots of the idea of America
  • A Complete Unknown: Jason’s slideshow & Bob Dylan’s anti-authoritarianism
  • Getting woo on Tenet’s Sator square
  • How do you know when a movie is finished?
  • The fragility of the artist
  • We are all co-creators
  • Jason as World Emperor
  • MORE!

Books Mentioned:

  • I Am a Strange Loop; by Douglas Hofstadter
  • The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom
  • One Summer: America 1927; by Bill Bryson
  • The Hypomanic Edge: What Built America; by John D. Gartner
  • The Hitchhiker's Guide to the Galaxy; by Douglas Adams

Movies Mentioned:

  • New Space (directed by Jason Carman)
  • Flow (directed by Gints Zilbalodis)
  • My Dinner With Andre (directed by Louis Malle)
  • Star Wars (directed by George Lucas)
  • A Complete Unknown (directed by James Mangold)
  • Tenet (directed by Christopher Nolan)
  • Dune: Part Two (directed by Denis Villeneuve)

0:00 1:30:05

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

Hosts
Jim O'Shaughnessy
Guests
Anne-Laure Le Cunff
Keywords
tiny experiments neuroscience productivity culture cognitive scripts model of success goal-obsessed world

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 about it. A neuroscience PhD, 100,000+ newsletter subscribers, and a newly published book later, she’s developed a new model of success — one built around conducting “tiny experiments” that help her build a life on her own terms.

She joins me to discuss how we get trapped in cognitive scripts, the hidden dangers of productivity culture, how we can experiment our way to a better life and MUCH more!

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:

Show Notes:

  • How do you know you are bored out?
  • People who love us the most might turn out to be our biggest blockers
  • Don't confuse activity with effectiveness
  • We will do virtually anything to gain what is really an illusion of control
  • The map is not the territory, the menu is not the meal. And yet, words are magic spells.
  • The Winner’s Script and the Loser’s Script
  • "You got to run at the top speed if you just want to stay in place.”
  • Let go of the linear and replace it with the loop- a more cyclical approach for growth
  • Can you sit alone in a room for 15 minutes?
  • Procrastination is just a signal from your brain that something is not quite working right now
  • We know nothing
  • AI is a rocket ship for the mind
  • In 100 years, nobody will remember you

Books Mentioned:

  • Why Greatness Cannot Be Planned; by Ken Stanley
  • Thinking in Bets; by Annie Duke
  • Collective Illusions; by Todd Rose
  • Maybe Logic; by Robert Anton Wilson
  • Beginning of Infinity; by David Deutsch
  • Science and Sanity: An Introduction to Non-Aristotelian Systems and General Semantics; by Alfred Korzybski
  • The Science of Storytelling: Why Stories Make Us Human and How to Tell Them Better; by Will Storr

Ratings
Global:
4.6 rating 228 reviews
USA
4.6 ratings 168 reviews
Canada
4.7 ratings 22 reviews
UK
4.8 ratings 18 reviews
Australia
4.6 ratings 10 reviews
Ireland
4.3 ratings 3 reviews
Singapore
5.0 ratings 3 reviews
New Zealand
5.0 ratings 2 reviews
South Africa
5.0 ratings 2 reviews