Infinite Loops

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

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 retirement planning, Christine worked as a fund analyst, bringing a unique perspective that combines deep investment knowledge with practical financial wisdom.

Christine joins the show to discuss why retirement isn't just about hitting your "magic number," how to overcome the psychological barriers to retirement spending, why keeping your inner circle vibrant is crucial for long-term happiness, the surprising power of lifetime giving, 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
• Twitter
• LinkedIn

Show Notes:

• Retirement Focus: Finances or Lifestyle?
• Bring Your Kids In The Loop
• Embrace the Challenges of Social Health
• A Day in The Life of a Retiree
• Defaulting People Into Saving
• Genesis of the FIRE Movement
• Horsemen of The Investment Apocalypse
• The Delicate Balance of Investment Buckets
• Dodging A Single Point of Failure
• How to Sniff Out Fishy Financial Advice
• The Saver vs the Investor Personality Type
• Keeping Up With Mr. Market
• Annuities: The Low-Risk Underdog
• Christine as World Emperor

Books / Authors Mentioned:

• How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement; by Christine Benz
• The works of Jonathan Franzen

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 while maintaining ambitious visions for change. His current work spans housing, infrastructure, and innovation policy, with a particular emphasis on meta-scientific approaches to research funding and development.

In this episode we discuss why Ireland should embrace techno-optimism, how to beat the NIMBY challenge with win-win solutions, why young scientists need more research funding, and MUCH more. Plus, we even touch on drone coffee deliveries (happening now in Dublin) and the things needed to unleash Ireland's entrepreneurial spirit.

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:

• Progress Ireland Website
• Twitter
• LinkedIn

Show Notes:

• The Irish GDP Boom
• The Origins of Progress Ireland
• The Path Past Bureaucratic Barriers
• Where the State Meets the Street
• How Bad Political Vibes Can Seep in
• Where the Creme De La Creme Goes in State Projects
• Innovation Amidst EU's Strict Restrictions
• National EU Friction
• Densification Dilemmas
• Balancing Efficiency and Equity in Public Procurement
• How to Handle NIMBYs
• Pushing Past Infrastructural Comfort Zones
• Fostering Cultural Shifts
• What is Metascience?
• Recalibrating Success Metrics
• The Irish Brain Drain

Books Mentioned:

• Where the State Meets the Street by Bernardo Zacka

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 Congress' drug dealer"
• The Great Financial Crash & America's accountability crisis
• How to disagree agreeably
• How democracy REALLY works
• Why we should bring back Glass-Steagall
• The problem of cluelessness
• Solutions to the accountability crisis
• What has happened to investigative journalism?
• Why partisanship is overstated
• Rudy as World Emperor
• MORE!

Books Mentioned:

• Yellen: The Trailblazing Economist Who Navigated an Era of Upheaval; by Jon Hilsenrath
• Deterring Democracy; by Noam Chomsky
• The Rule of Nobody: Saving America from Dead Laws and Broken Government; by Philip K. Howard