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 data to build an AI-powered life coach, to the emotional intelligence hiding inside envy, to the surprising lessons he learned walking through a tiny historical museum in Coconut Grove.

We also dig into the messy magic of identity shifts, how fit dads triggered a personal transformation, and why letting go of productivity-as-performance might be the most productive thing you can do. Plus: the power of NotebookLM, building AI-native systems of self-awareness, and why the future will belong to those who embrace the one-way door.

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:

• Tiago Forte’s Website
• Tiago Forte on X
• Tiago Forte on LinkedIn
• Tiago Forte’s Annual Reviews
• Building A Second Brain Book
• The PARA Method Book
• I Replaced my $700/hour Coach with NotebookLM — Here’s What Happened (YouTube)
• What I Learned About the Future By Reading 100 Science Fiction Books

Show Notes:

• Closing the Door on Second Brain
• The Power of the Annual Review
• Tiago's Family: Incredibly Vibrant, Visual, Auditory
• Incorporating AI Into Work & Life
• Joe Hudson: Mentorship and Emotional Intelligence
• Miami: The Most Introspective Place on Earth
• Irreversible Decisions
• Archival Material: Underrated Forcing Function
• The Future of Book Publishing
• The Hard Truth on Performance Reviews
• AI Skepticism & Building Moats
• AI-First Mentality for Early Adopters
• Learning From Sci-Fi Books
• Cumulative Cultural Evolution
• Tiago as Emperor of the World

Books Mentioned:

• Building A Second Brain: A Proven Method to Organize Your Digital Life and Unlock Your Creative Potential; by Tiago Forte
• The PARA Method: Simplify, Organize, and Master Your Digital Life; by Tiago Forte
• How Emotions are Made: The Secret Life of the Brain; by Lisa Feldman Barrett
• Tiny Experiments: How to Live Freely in a Goal-Obsessed World; by Anne-Laure Le Cunff
• Why Greatness Cannot Be Planned; by Kenneth O. Stanley and Joel Lehman
• Molecules Of Emotion: The Science Behind Mind-Body Medicine; by Candace B. Pert
• What Works on Wall Street; by Jim O’Shaughnessy
• The Beginning of Infinity; by David Deutsch
• One Summer: America, 1927; by Bill Bryson
• White Mirror; by Tinkered Thinking
• The Forever War; by Joe Halderman

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 transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Nir’s personal blog
• Nir’s LinkedIn
• Nir’s Twitter
• Nir’s YouTube channel
• Nir’s Habit Tracking Tool
• Nir’s Schedule Maker Tool

Show Notes:

• What Makes Silicon Valley’s Tech Products So Sticky?
• The Morality of Manipulation
• The Perils of Legalized Gambling
• Twitter is for Journalists and Nerds
• AI for Behavioural Design
• Believing in our own Agency
• On Labels and Limiting Identities
• Pills Don’t Teach Skills
• The Power of an Internal Locus of Control
• Escaping Discomfort & Getting Hooked
• AI as a Self-Directed Personal Tutor
• Nir As Emperor of the World

Books Mentioned:

• Hooked: How to Build Habit-Forming Products; by Nir Eyal
• Influence; by Robert Cialdini
• Sick Souls, Healthy Minds: How William James Can Save Your Life; by John Kaag

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 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:

• Lex
• Twitter
• Substack
• LinkedIn

Show Notes:

• Lex: Your Spotter In the Writing Gym
• Letting People Into Your Creative Process
• Collaboration-as-a-Service
• Creation Is Fundamentally About Choices
• What Will Become of the AI Holdouts?
• AI Is Like the Internet In 1995
• Can AI Unfuck the Government?
• Blindspots While Working In Organizations
• Rethinking The ‘Article’ As A Medium
• Memes Are Dense Information Packets
• It’s Time for Solo Founders
• Why Learning About Cumulative Cultural Evolution Is Vital
• What’s Next for Lex?
• Writing As A Way To Design Thoughts
• Nathan As World Emperor

Books Mentioned:

• A Swim in a Pond in the Rain: In Which Four Russians Give a Master Class on Writing, Reading, and Life; by George Saunders
• The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich
• The Secret of Our Success: How Culture Is Driving Human Evolution, Domesticating Our Species, and Making Us Smarter; by Joseph Henrich

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 non-linear career paths, embracing authenticity, working with dazzling, delusional people and 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:

• X/Twitter
• Linkedin
• Powerhour: The CIA For Entrepreneurship

Show Notes:

• Tommy’s Origin Story
• Using The Third Door
• Lessons from Documenting the Homeless
• Can We Ever Be Our Authentic Self?
• What Traits Tommy Looks for in People
• Bringing Delusional People Together
• The East Coast - West Coast Bubbles
• Being a ‘Weirdo Broker’
• Process Over Outcomes. Serendipity Over Itinerary.
• Different Personalities in Public vs. Private Markets
• The Importance of Learning People
• Life Isn’t a Highlight Reel - Live It All
• Tommy As World Emperor

Books Mentioned:

• The Third Door: The Mindset of Success; by Alex Banayan
• One-upmanship; by Stephen Potter
• Class: Style and Status in the USA; by Paul Fussell
• Dignity: Seeking Respect in Back Row America; by Chris Arnade
• The Science of Getting Rich; by Wallace D. Wattles
• The Act of Creation; by Arthur Koestler

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:

• Twitter: https://twitter.com/Alex_Danco
• Substack: https://danco.substack.com
• Website: https://alexdanco.com/
• Previous episode: https://newsletter.osv.llc/p/finding-method-in-the-madness?utm_source=publication-search

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)

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:

• Website
• Instagram
• The Sovereign Artist
• KronArête (Community)
• Gumroad
• X
• The Great Reshuffle

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

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:

• Blog
• Twitter
• LinkedIn
• Ritholtz Wealth Management

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

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:

• Jason on X
• Story Company on X
• Story Company on Youtube
• Story Company’s Website
• “New Space” Frontier Film
• Jason’s Fellowship

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)

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:

• Anne-Laure’s Twitter/X
• Ness Labs
• Tiny Experiments Book

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

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 Anton Wilson. I could talk about this stuff for days, and we had a blast discussing Wilson’s ideas, influence and impact. Consider it a beginner’s guide to avoiding cosmic schmuckery.

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:

• Chapel Perilous: The Life and Thought Crimes of Robert Anton Wilson; by Gabriel Kennedy
• The Thinker and the Prover; by Jim O’Shaughnessy
• Gabriel’s Substack

Show Notes:

• The most interesting man of the last fifty years?
• How can we escape chapel perilous?
• The anti-determinist, rock & roll philosophy of Bob Wilson
• Tune in: a 30 minute masterclass on the influences, ideas and impact of Robert Anton Wilson
• How to avoid becoming a cosmic schmuck
• Who influenced Wilson the most?
• Why you should read Wilson
• Gabriel as World Emperor
• MORE!

Books & Articles Mentioned:

• The Thinker and the Prover; by Jim O’Shaughnessy
• Chapel Perilous: The Life and Thought Crimes of Robert Anton Wilson; by Gabriel Kennedy
• Prometheus Unbound by Robert Anton Wilson
• Quantum Psychology: How Brain Software Programs You and Your World by Robert Anton Wilson
• The Illuminatus! Trilogy by Robert Anton Wilson and Robert Shea
• Cosmic Trigger Volume I: Final Secret of the Illuminati by Robert Anton Wilson
• The New Inquisition: Irrational Rationalism and the Citadel of Science by Robert Anton Wilson
• Prometheus Rising by Robert Anton Wilson
• Quantum Psychology: How Brain Software Programs You and Your World by Robert Anton Wilson
• The Waste Land by T. S. Eliot
• From Ritual to Romance by Jessie L. Weston
• Finnegans Wake by James Joyce
• Science and Sanity: An Introduction to Non-Aristotelian Systems and General Semantics by Alfred Korzybski
• On the Einstein Podolsky Rosen Paradox; by John S. Bell
• How the Hippies Saved Physics: Science, Counterculture, and the Quantum Revival by David Kaiser
• Character Analysis by Wilhelm Reich
• Man Meets Dog by Konrad Lorenz