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

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 why podcasts are dangerous (😬), why content creators should have a 10 post limit, how he identifies kaleidoscopic aliens to invest in, 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:

• Digital
• Mark’s Twitter
• Mark’s LinkedIn

Show Notes:

• Why podcasts are dangerous
• Why content creators should be limited to 10 posts
• Advice is simple; life is hard
• How to find a kaleidoscopic alien
• How to win the great game
• Mania-immune investing
• Jim’s “I’m a sports guy” algorithm
• What beliefs would you die for?
• What have you unlearned in the past year?
• The fragility of morality
• Passion as a forcing function
• Movie recommendations: My Dinner With Andre & Elevator to Gallows
• Mark as World Emperor
• MORE!

Books & Articles Mentioned:

• How to Be Successful; by Jim O’Shaughnessy
• How to Win Friends and Influence People; by Dale Carnegie

John Kennedy, a director at the Corsi-Rosenthal Foundation, is tackling an overlooked crisis in American education: air quality. 

With the ingenious use of a simple $60 box fan, he's on a mission to revolutionize the health and learning environments of students nationwide.

It's mind-boggling how much low-hanging fruit there is here. The difference that clean air makes to health and brain capacity is enormous, and it's a surprisingly cheap problem to fix. In fact, as you'll hear about halfway through our conversation, I was so convinced by John and the Corsi-Rosenthal team's solution that I committed to offering him a $100k Fellowship on the spot.

But our discussion went far beyond air quality. John shared fascinating insights into the future of education—how we can reorganize it from the ground up to produce happy, healthy, and high-agency adults ready for the challenges of the 21st century.

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:

• The Corsi-Rosenthal Foundation
• John’s LinkedIn
• John’s Twitter

Show Notes:

• Nobody gets to choose the air they breathe…
• Why has air quality been overlooked?
• When Jim got stranded up a mountain
• How do you scale a K-12 solution?
• What would it cost to put a Cori-Rosenthal box in every New York classroom?
• Surprise! Welcome to the O’Shaughnessy Fellowships
• What would a model 21st-century K-12 system look like?
• How to overcome systemic inertia
• Do Charter schools work?
• Why public schools can’t mimic private school innovations
• What exciting developments are happening in edtech?
• What does public school look like in 2044?
• John as World Emperor
• MORE!

Books Mentioned:

• The Unwinding: An Inner History of the New America; by George Packer

Michael Strong has spent decades quietly revolutionizing education by designing innovative schools and programs built around agency, critical thinking, entrepreneurship and creativity.

He is the founder and CEO of The Socratic Experience, a virtual school that equips students for lifelong happiness and success through Socratic dialogue.

Alongside his work in the US, he has educational consulting experience in multiple developing nations.

And… he’s a fellow Minnesotan!

Michael joins the show to discuss whether Socratic education can scale, the benefits of the Mormon model, why high agency is the default, 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:

• Michael’s Substack
• Twitter
• The Socratic Experience

Show Notes:

• One book a night and mental chess - a Minnesotan childhood.
• Can Socratic education scale?
• Are we entrenching a new elite?
• Why high agency is the default
• Creating new subcultures & the benefits of the Mormon model
• Experimenting our way to prosperity
• Tearing down the citadel, secret censorship & claiming the moral high ground
• Prediction markets & why we should be betting on our reputation
• The heroic tradition of reason
• Michael as World Emperor
• MORE!

Books Mentioned:

• Dr. Semmelweis vs. the World (Infinite Loops Substack)
• Ignore. Fight. Ridicule (Infinite Loops Substack)
• The Habit of Thought: From Socratic Seminars to Socratic Practice; by Michael Strong
• Be the Solution: How Entrepreneurs and Conscious Capitalists Can Solve All the World's Problems; by Michael Strong and John Mackey
• The Case Against Adolescence: Rediscovering the Adult in Every Teen; by Robert Epstein
• The Status Game: On Human Life and How to Play It; by Will Storr
• The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson
• Hierarchy in the Forest: The Evolution of Egalitarian Behavior; by Christopher Boehm
• Collective Illusions: Conformity, Complicity, and the Science of Why We Make Bad Decisions; by Todd Rose
• Can Gambling Save Science? Encouraging an Honest Consensus; by Robin Hanson
• Skin in the Game: Hidden Asymmetries in Daily Life; by Nassim Nicholas Taleb
• Hothouse Earth: An Inhabitant's Guide; by Bill McGuire
• Think in Bets: Making Smarter Decisions When You Don't Have All the Facts; by Annie Duke
• The Ultimate Resource; by Julian L. Simon
• Keep Your Identity Small; by Paul Graham

Sahil Bloom, a prolific creator, founder and investor, has mastered the art of translating complex ideas about wealth and success into wisdom that resonates with millions. His newsletter, The Curiosity Chronicle, grew from just 100 readers to over 800,000 subscribers in three years - a testament to his ability to cut through the noise with clarity and insight. His upcoming book, "The 5 Types of Wealth," challenges our conventional understanding of what it means to be truly wealthy, arguing that financial success is just one piece of a much larger puzzle.

Here's what makes Sahil fascinating - he's built his empire not through traditional paths (he left his high paying private equity job), but by following his curiosity and sharing what he learns along the way. Today, we'll explore the frameworks that have helped him impact millions, why traditional definitions of success might be holding us back, and how Sahil’s relationship with time reshaped the way he thinks about wealth, wisdom, and the pursuit of a meaningful life.

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:

• Sahil’s Website
• Sahil’s Twitter
• Sahil’s Blog

Show Notes:

• The Ripple Effect of spreading good ideas
• Sahil’s Origin Story
• The Finite Impermanence of Time
• Would you trade lives with Warren Buffett?
• The Loneliness Epidemic
• The Paradox of setting Big Goals and needing Small Steps to get there
• Why waking up at 5am can rewire your brain
• Why do people chase the wrong things?
• Jim and Sahil’s Memento Mori
• Factoring in the 5 Types of Wealth when making a decision
• What makes A Wonderful Life?
• Money As a Byproduct of Pursuing Purpose
• Sahil’s Message As World Emperor

Books Mentioned:

• Zorba the Greek; by Nikos Kazantzakis
• Adventures of a Bystander; by Peter Drucker
• The Anxious Generation; by Jonathan Haidt
• Tao Te Ching; by Lao Tzu
• Collective Illusions; by Todd Rose
• The Psychology of Money; by Morgan Housel