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

Seth Stephens-Davidowitz, a data scientist and bestselling author, is known for his brilliant use of data to upend conventional wisdom - often with humorous, surprising, and occasionally shocking results. His latest book, Who Makes the NBA, uses data to interrogate some of basketball’s biggest questions, consistently yielding unexpected insights. Here’s the kicker - he wrote the entire book in just 30 days after discovering Code Interpreter.

Unsurprisingly for a former quant, I had a blast chatting to Seth. Topics discussed include why so many NBA players are called Chris, whether basketball is due for a Moneyball moment, and why so many of us misunderstand the rags-to-riches story.

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:

• Seth’s Website
• Twitter

Show Notes:

• Author, data scientist… comedian?
• Using Code Interpreter to write a book in 30 days
• The trait that makes it incredibly easy to become an NBA player
• Why the best NBA player in history isn’t who you think it is
• Is basketball due a Moneyball moment?
• Why are so many NBA players named Chris?
• What people get wrong about the rags-to-riches story
• The hidden magic of data storytelling
• Finding your audience
• The danger of glamour
• Keep it simple, stupid
• Why the standard interview sucks
• Doppelgangers & the power of A/B testing
• The overdue revolution in health data
• Why Google should be worried
• Stated vs revealed preferences
• The power of enormous data sets
• Seth as World Emperor

Books Mentioned:

• Who Makes the NBA?: Data-Driven Answers to Basketball's Biggest Questions; by Seth Stephens-Davidowitz
• Don't Trust Your Gut: Using Data to Get What You Really Want in Life; by Seth Stephens-Davidowitz
• Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are; by Seth Stephens-Davidowitz
• What Works on Wall Street: A Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy

Julian Gough sums up his career as follows: “I just sit in my room and write.”

Well, I think being an acclaimed children’s author, novelist, stage playwright, poet and top-ten Irish musician is a little more impressive than he’s letting on…

Oh, and I didn’t even mention that he wrote the ending to the computer game Minecraft!

His current project, The Egg and The Rock, puts all of this to shame. This book, which Julian is writing in public on Substack, seeks to do no less than redescribe the universe, arguing that is not some random, dead, purposeless sack of chemicals, but instead a living, evolving organism.

Julian joins me to discuss why the arc of human evolution bends towards man-made black holes, the hidden catastrophe at the heart of materialist science, the strange life of subterranean ice aliens, and MUCH more!

This was such an interesting conversation - I can’t wait for you to hear it. 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:

• Julian’s Website
• The Egg and The Rock
• Julian’s Twitter

Show Notes:

• “I just sit in my room and write”
• Why write a book in public?
• Materialism & science’s hidden catastrophe
• “The scientific method is in conflict with human nature”
• The faulty assumption at the heart of cosmology
• Big bangs, supermassive black holes & Darwinian evolution: A ~30 minute masterclass in cosmological natural selection
• “I'm predicting very, very large amounts of life in this universe”
• The strange life of subterranean ice aliens
• Could we spot man-made black holes?
• Bringing consciousness into physics
• Pulling back the curtain
• Julian as World Emperor
• MORE!

Books & Articles Mentioned:

• The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson
• Against Method: Outline of an Anarchistic Theory of Knowledge; by Paul Feyerabend
• What the Tortoise Said to Achilles; by Lewis Carroll
• The Life of the Cosmos; by Lee Smolin
• What Is Life? The Physical Aspect of the Living Cell; by Erwin Schrödinger
• Isis Unveiled: A Master-Key to the Mysteries of Ancient and Modern Science and Theology; by Helena Petrovna Blavatsky
• The Bhagavad Gita
• Did the Universe evolve?; by Lee Smolin
• The Great Filter - Are We Almost Past It?; by Robin Hanson

Ben Reinhardt is the founder of Speculative Technologies “a nonprofit industrial research lab that’s working to unlock a wonderful, abundant future through technologies that don’t have a home in other institutions.”

He has previously worked at NASA and Bay Area startups/VC firms, founded a startup building robotics for eldercare, and helped entrepreneurs start companies in Singapore. Oh, and he has a Ph.D. in space robotics from Cornell University and is one of the few people with a B.Sc. in history!

Ben, who brings his expertise in emerging technologies to the OSV advisory council, joins the show to discuss why tech people don’t do philanthropy, when to trust a credential, why there aren’t more government moonshot programs, why academia is beholden to the new, 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:

• Speculative Technologies
• Ben’s Twitter
• Ben’s LinkedIn

Show Notes:

• Speculative Technologies: the four-stage roadmap
• How early VC funding can affect incentives
• From ‘eureka!’ to getting it out into the world
• Market failure & institutional consolidation
• Where are the moonshot programs?
• The skills needed to run a research program
• Why tech people don’t do philanthropy
• Turning philanthropy into a status game
• The hidden importance of materials & manufacturing
• When to trust a credential
• Agency & American culture
• Lean ideas vs. fat ideas
• Why academia is beholden to novelty
• Ben as World Emperor
• MORE!

Books Mentioned:

• What Works on Wall Street, Fourth Edition: The Classic Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy
• The Beginning of Infinity: Explanations that Transform the World; by David Deutsch
• The Road; by Cormac McCarthy
• The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; by John D. Gartner
• The Coffee Can portfolio; by Robert G. Kirby

My guest on Infinite Loops this week knew he wanted to be an entrepreneur from the time he was buying and selling things on eBay.

Jay Reno claims he didn’t know what the word ‘arbitrage’ meant back then, but if you tug on the colourful threads of his career, you’d reveal the kind of tenacity and resourcefulness that allows special founders like him to repeatedly find value in places that have long been deserted by everybody else.

If you listen in on today’s episode, it will become apparent why O’Shaughnessy Ventures invested in Jay and his current venture. Jay is the CEO and Founder of Pointhound, which helps people find amazing deals on flights and travel using their credit card points and miles. He’s also a partner at 645 ventures.

Among other fun pursuits, he’s spent the last ten years building all sorts of cool things; like a same-day grocery delivery service, a craft coffee company, a restaurant and bar reservation app, and a furniture rental service for city dwellers.

We spent our conversation talking about his advice for first-time founders; his learnings from building Pointhound; the whimsical world of credit card point programmes; his thoughts on consumer psychology; and much more!

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:

• Jay’s Twitter
• Jay’s LinkedIn
• 645 Ventures
• Pointhound HQ

Show Notes:

• How To Bring Your Idea To Life
• The Virtues of the Y-Combinator Model
• Picking the Right Investor
• Pointhound & The Points Game
• On Consumer Psychology and Trying New Things
• Removing the Invisible Barrier
• Product Cycles and User Feedback
• Slow Down to Speed Up
• The Common Pitfalls in Building Consumer Products
• The Credit Card Prestige Factor
• The Cashback Conundrum
• The Future of Pointhound
• Jay, The Emperor of The World

Books & Articles Mentioned:

• My Inventions: The Autobiography of Nikola Tesla; by Nikola Tesla
• Mistakes were Made. (And, Yes, by Me.); by Jim O’Shaughnessy

My guest today is Michael Garfield, a paleontologist, futurist, writer, podcast host and strategic advisor whose “mind-jazz” performances — essays, music and fine art — bridge the worlds of art, science and philosophy.

This year, Michael received a $10k O’Shaughnessy Grant for his “Humans On the Loop” discussion series, which explores the nature of agency, power, responsibility and wisdom in the age of automation.

This whirlwind discussion is impossible to sum up in a couple of sentences (just look at the number of books & articles mentioned!) Ultimately, it is a conversation about a subject I think about every day: how we can live curious, collaborative and fulfilling lives in our deeply weird, complex, probabilistic world.

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 Website
• Humans On The Loop
• Twitter
• Future Fossils Substack

Show Notes:

• What is “mind jazz”?
• Humans “ON” the loop?
• The Red Queen hypothesis and the power of weirdness
• Probabilistic thinking & the perils of optimization
• Context collapse, pernicious convenience & coordination at scale
• How organisations learn
• Michael as World Emperor
• MORE!

Books, Articles & Podcasts Mentioned:

• The Nature of Technology: What It Is and How It Evolves; by W. Brian Arthur
• Pharmako-AI; by K Allado-McDowell
• The Global Brain: The Evolution of Mass Mind from the Big Bang to the 21st Century; by Howard Bloom
• The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom
• One Summer: America, 1927; by Bill Bryson
• Through the Looking-Glass, and What Alice Found There; by Lewis Carroll
• The Beginning of Infinity: Explanations That Transform the World; by David Deutsch
• Scale Theory: A Nondisciplinary Inquiry; by Joshua DiCaglio
• Revenge of the Tipping Point: Overstories, Superspreaders and the Rise of Social Engineering; by Malcolm Gladwell
• The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich
• Do Conversation: There's No Such Thing as Small Talk; by Robert Poynton
• Reality Hunger: A Manifesto; by David Shields
• The Time Falling Bodies Take to Light: Mythology, Sexuality and the Origins of Culture; by William Irwin Thompson
• The New Inquisition: Irrational Rationalism and the Citadel of Science; by Robert Anton Wilson
• Designing Neural Media; by K Allado-McDowell
• Pace Layering: How Complex Systems Learn and Keep Learning; by Steward Brand
• Losing Humanity: The Case against Killer Robots; by Bonnie Docherty
• What happens with digital rights management in the real world?; by Cory Doctorow
• The Evolution of Surveillance Part 1: Burgess Shale to Google Glass; by Michael Garfield
• An Introduction to Extitutional Theory; by Jessy Kate Schingler
• 175 - C. Thi Nguyen on The Seductions of Clarity, Weaponized Games, and Agency as Art; Future Fossils with Michael Garfield
• 🎶⚔️👏🏼 205 - Greg Thomas & Stephanie Lepp on Jazz Leadership & Antagonistic Cooperation; Future Fossils with Michael Garfield
• 🌏🚜🫀212 - Manfred Laubichler & Geoffrey West on Life In The Anthropocene & Living Inside The Technosphere; Future Fossils with Michael Garfield

My guest today is Max Meyer, the proprietor of Arena Magazine, a new quarterly publication exploring technology, capitalism and civilization.

Arena’s aim? To “make it okay to dream in public again.”

Max and I discuss why he launched a print magazine in 2024, WTF happened to legacy media, the wisdom of Ratatouille 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:

• Max’s Twitter
• Arena Magazine
• The New Needs Friends
• The Earthly Miracle of the Grocery Store
• Robert F. Kennedy announces the death of Martin Luther King, Jr.

Show Notes:

• What is going on with legacy media?
• Print advertising and the race to the bottom
• The collapse of trust in the media
• TikTok brain, news consumption & social media as a steam valve
• Bailouts & the appeal of the “zero interest fairyland”
• The wisdom of Ratatouille
• The decline of Presidential oratory
• American progress & the population bomb that didn’t go off
• Failure is a ladder
• The one rule of capitalism
• Long haul flights: Where’s our roast turkey?
• Why is Arena a physical magazine?
• Max as Emperor of the world
• MORE!

Books & Articles Mentioned:

• The Beginning of Infinity: Explanations That Transform the World; by David Deutsch
• The Ultimate Resource; by Julian L. Simon
• The Population Bomb; by Dr Paul R. Ehrlich
• The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom
• How United Became an Airline; by Andy Kessler (WSJ)
• This is Water; by David Foster Wallace line.

Parmita Mishra is a computational biologist and the founder & CEO of Precigenetics, a company aiming to become a rocket to precision medicine.

Parmita is deeply knowledgeable about cutting-edge biology, particularly epigenetics — how behavior and environment can affect gene function without altering genetic code. Her passion for advancing our understanding of diseases is inspiring (and contagious: OSV is an investor in Parmita’s company!)

In our conversation, Parmita and I discuss everything from the curious case of male baldness to how her parents have saved 50,000 lives. 

I hope you enjoy this conversation as much as I did. For the full transcript, highlights, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• LinkedIn
• Twitter
• Website
• Precigenetics Twitter
• Preciginetics launch post

Show Notes:

• Explaining epigenetics to a golden retriever
• The curious case of male pattern baldness
• How to think about biology: start from first principles & beware binary thinking
• The lens you look through determines what you see
• The problem of data collection in biology
• Why the FDA needs to change its approach
• Why we still don’t understand the human brain
• Garry Tan’s advice: “Get an idea. Get a co-founder.”
• What’s been surprising about foundership?
• Failure is a ladder
• Obsession & how Parmita’s parents have saved 50,000 lives
• The most surprising things about America
• Parmita as World Empress

Books Mentioned:

• What is Life?; by Erwin Schrodinger
• I should have loved biology; by James Somers
• Gödel, Escher, Bach: An Eternal Golden Braid; by Douglas Hofstadter
• The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; by John D. Gartner

Professor Luis Seco is a mathematician, educator, and investor.

Among many other titles and achievements, he is the Professor of Mathematics at the University of Toronto, Director of the quant research hub Risklab, Chair of the Centre for Sustainable Development at the Fields Institute, and co-founder of the asset management firm Sigma Analysis & Management Ltd.

Got all that?!

This one was really fun, and not just because Luis is a fellow quant. We discuss how maths resembles Beethoven’s Fifth Symphony, the future of the ‘metaversity’, the most important lesson Luis gives his students, why investing isn't what it used to be, 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
• YouTube

Show Notes:

• What Luis learned from the Beethoven of mathematics
• “Mathematics is the language computers speak”
• The role of community in an increasingly confusing world
• Lifelong education & the voyage to the human brain
• Why to teach is to be human
• Timebinding & social media as a steam valve
• What matters more - content or communication?
• Math as a social science: quantifying risk in a nonlinear world
• From paper, to numbers, to images: The changing nature of data
• Why the future of education lies in decentralization
• Swarm solutions & why we’re in the century of collaboration
• Metaversities & the case for bringing your kids to work
• Why managing money is now based on words, not numbers
• Luis as Emperor of the World
• MORE!

Books Mentioned:

• The Hitchhiker's Guide to the Galaxy; by Douglas Adams
• The Two Cultures; by C.P. Snow
• Zen and the Art of Motorcycle Maintenance; by Robert M. Pirsig
• Manhood of Humanity; by Alfred Korzybski
• How to Win Friends and Influence People; by Dale Carnegie
• The Myth of 1926: How Much Do We Know About Long-Term Returns on U.S. Stocks?; by Edward F. Mcquarrie

Anthony Pompliano — investor, entrepreneur, and media powerhouse — returns four years and 228 episodes later to discuss his new book, How To Live an Extraordinary Life, a collection of 65 heartfelt letters to his two children.

At just 36, Anthony has already invested in circa 200 companies, served in Iraq with the U.S. Army, built and sold multiple businesses, and created one of the world’s largest independent media platforms. You don’t accomplish all that without learning a thing or two, and in this episode we dig into his hard-earned insights — from the uniting traits of the world’s smartest people, to the luxury of pessimism, to why luck isn’t real.

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:

• How To Live an Extraordinary Life
• Website
• Twitter
• The Pomp Letter
• Anthony’s Previous Episode

Show Notes:

• The hidden power of “I don’t know”
• Why Anthony started writing letters to his children
• Today is practice for tomorrow
• Carve your ethics in stone, but your opinions in sand
• How bad positioning poisons decision-making
• Are there any parts of the book Anthony no longer believes in?
• What unites the smartest people in the world
• Why luck isn’t real
• The luxury of pessimism
• Power laws everywhere!
• Anthony as Emperor of the World
• MORE!

Books, Articles & Podcasts Mentioned:

• Adventures of a Bystander; by Peter F. Drucker
• The Art of Learning: An Inner Journey to Optimal Performance; by Josh Waitzkin
• How Will You Measure Your Life?: A thought-provoking approach to measuring life's success; by Clayton M. Christensen, James Allworth and Karren Dillon
• Rules for a Knight; by Ethan Hawke
• The Rise and Fall of American Growth: The U.S. Standard of Living since the Civil War; by Robert J. Gordon
• Why Writing Letters to Your Kids Is the Best Gift You Can Give Them as Adults; by Polina Pompliano
• Shane Parrish on the Clear Thinking podcast
• Lucky vs, Repeatable; by Morgan Housel
• What Kind of Lucky Are You?; by Jim O’Shaughnessy