Infinite Loops
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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Tommy Potter — Building the CIA for Entrepreneurs (EP.264)
04/17/2025
Tommy Potter — Building the CIA for Entrepreneurs (EP.264)
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 . Important Links: 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
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Alex Danco — On Strollers, Slop & Citizen Kane (EP.263)
04/10/2025
Alex Danco — On Strollers, Slop & Citizen Kane (EP.263)
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 . Important Links: Twitter: Substack: Website: Previous episode: 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 ; by Venkatesh Rao ; 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)
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Vizi Andrei — The Way of the Tinkerer (EP.262)
04/03/2025
Vizi Andrei — The Way of the Tinkerer (EP.262)
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
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Barry Ritholtz — Make Fewer Errors, Make More Money (EP.261)
03/27/2025
Barry Ritholtz — Make Fewer Errors, Make More Money (EP.261)
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 . 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
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Jason Carman — Filmmaking at the Frontier (EP.260)
03/20/2025
Jason Carman — Filmmaking at the Frontier (EP.260)
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 . 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: (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)
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Anne-Laure Le Cunff — Experiment Your Way to a Better Life (EP.259)
03/13/2025
Anne-Laure Le Cunff — Experiment Your Way to a Better Life (EP.259)
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 . 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
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Gabriel Kennedy — The Life and Thought Crimes of Robert Anton Wilson (EP.258)
03/06/2025
Gabriel Kennedy — The Life and Thought Crimes of Robert Anton Wilson (EP.258)
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 . Important Links: ; by Gabriel Kennedy ; by Jim O’Shaughnessy 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: ; 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
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The Art of Retirement — Christine Benz (EP.257)
02/27/2025
The Art of Retirement — Christine Benz (EP.257)
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: 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
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Luke Fehily — Ireland's Innovation Playbook (EP.256)
02/20/2025
Luke Fehily — Ireland's Innovation Playbook (EP.256)
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 . Important Links: 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
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Rudy Havenstein — How to Fix America’s Accountability Crisis (EP.255)
02/13/2025
Rudy Havenstein — How to Fix America’s Accountability Crisis (EP.255)
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: 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
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Mark Daniel — How to Find a Kaleidoscopic Alien (EP.254)
02/06/2025
Mark Daniel — How to Find a Kaleidoscopic Alien (EP.254)
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 . Important Links: 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: ; by Jim O’Shaughnessy How to Win Friends and Influence People; by Dale Carnegie
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John Kennedy — The Hidden Crisis in American Education (EP.253)
01/30/2025
John Kennedy — The Hidden Crisis in American Education (EP.253)
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 . Important Links: 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
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Michael Strong — Let’s Get Socratical (EP.252)
01/23/2025
Michael Strong — Let’s Get Socratical (EP.252)
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 . Important Links: 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: (Infinite Loops Substack) (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 ; 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 ; by Paul Graham
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Sahil Bloom — A Multitude of Wealth (EP.251)
01/16/2025
Sahil Bloom — A Multitude of Wealth (EP.251)
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 . Important Links: 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
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Seth Stephens-Davidowitz — Who Makes the NBA? (EP.250)
01/09/2025
Seth Stephens-Davidowitz — Who Makes the NBA? (EP.250)
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 . Important Links: 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
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Julian Gough — The Egg and The Rock (EP.249)
01/02/2025
Julian Gough — The Egg and The Rock (EP.249)
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 . Important Links: 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 ; by Lee Smolin ; by Robin Hanson
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Ben Reinhardt — Speculative Technologies (EP.248)
12/26/2024
Ben Reinhardt — Speculative Technologies (EP.248)
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 . 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 . Important Links: 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 ; by Robert G. Kirby
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Jay Reno — Making A Point (EP.247)
12/19/2024
Jay Reno — Making A Point (EP.247)
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 . Important Links: 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: ; by Nikola Tesla ; by Jim O’Shaughnessy
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Michael Garfield — Play the (Mind) Jazz (EP.246)
12/12/2024
Michael Garfield — Play the (Mind) Jazz (EP.246)
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 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 . Important Links: 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 ; by K Allado-McDowell ; by Steward Brand ; by Bonnie Docherty ; by Cory Doctorow ; by Michael Garfield ; by Jessy Kate Schingler ; Future Fossils with Michael Garfield ; Future Fossils with Michael Garfield ; Future Fossils with Michael Garfield
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Max Meyer Launched a Print Magazine in 2024. Here’s Why. (EP.245)
12/05/2024
Max Meyer Launched a Print Magazine in 2024. Here’s Why. (EP.245)
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 . Important Links: 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 ; by Andy Kessler (WSJ) ; by David Foster Wallace line.
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Parmita Mishra — How to Think About Biology (EP.244)
11/28/2024
Parmita Mishra — How to Think About Biology (EP.244)
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 . Important Links: 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 ; 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
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Luis Seco — On Mathematical Beethovens, Decentralized Education & the Voyage to the Human Brain (EP.243)
11/21/2024
Luis Seco — On Mathematical Beethovens, Decentralized Education & the Voyage to the Human Brain (EP.243)
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 . Important Links: 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 ; by Edward F. Mcquarrie
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Anthony Pompliano — How to Live an Extraordinary Life (EP.242)
11/14/2024
Anthony Pompliano — How to Live an Extraordinary Life (EP.242)
Anthony Pompliano — investor, entrepreneur, and media powerhouse — returns four years and 228 episodes later to discuss his new book, , 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 . Important Links: 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 ; by Polina Pompliano ; by Morgan Housel ; by Jim O’Shaughnessy
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Sajith Pai — Exploring Indus Valley (Ep.241)
11/07/2024
Sajith Pai — Exploring Indus Valley (Ep.241)
There’s a quote I heard a long time ago that goes something like this - “India has consistently disappointed both the optimists and the pessimists”. It is equal parts pithy and profound, and does a somewhat passable job of summarising the multitudes contained in 21st century India. It’s a quote that was brought to life for me numerous times in my conversation with this week’s guest on Infinite Loops - Sajith Pai. Sajith is a GP at Blume Ventures, one of India’s largest homegrown VC firms. He's known for his prolific writing and sharp frameworks that have become part of Indian startup canon over the past decade. In 2018, he swapped a long-time career as a media executive for one as a venture capitalist. This changing of lanes, relatively late in his professional life, has given him a refreshingly nuanced perspective on the Indian startup ecosystem (which he’s bestowed with the moniker of ‘Indus Valley’, as a nod to both Silicon Valley as well as the Indus Valley Civilisation, one of the cradles of the ancient world and the ancestral civilisation of the Indian people). His most compelling insight? That India isn't the monolithic 1.5-billion-person market that many Westerners believe. Instead, it's three distinct "countries" hiding in plain sight. There's India One: 120 million affluent, English-speaking urbanites (think the population of Germany) who love their iPhones and Starbucks. Then comes India Two: 300 million aspiring middle-class citizens who inhabit the digital economy but not yet the consumption economy. Finally, there's India Three: a massive population with a similar demographic profile to Sub-Saharan Africa, that’s still waiting for its invitation to join India’s bright future. ‘India 1-2-3’ is one amongst many pearls of wisdom that Sajith gifted me over our conversation, that also touched on India as a "digital welfare state", India as a ‘low trust society’; the emergence of a new class of ‘Indo-Anglians’; how cultural nuances in India shape everything from app design to payment systems; and much, much more. Whether you're an investor, founder, or just curious about where the next decade of innovation might come from, this conversation is your crash course to understanding India in the 21st century. Sajith likes to say that ‘India is not for beginners’. Well, if you are a beginner on India, this week you’re in luck. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our . Important Links: Show Notes: The Three Indias Navigating India in the 21st century India as a ‘low trust’ society Touring ‘India 2’ The States and the Union Caste and Class in Modern India Governance and the Government Brain Drain The English Tax The Rise of the Indo-Anglians I, Writer On Media and Markets India as a Digital Welfare State The Virtues of Leapfrogging Sajith, The Emperor of the World Books and Articles Mentioned: ; by C. K. Prahalad ; by Charles Duhigg ; by Scott Adams ; by Blume VC
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Scott Aaronson — Quantumania (EP.240)
10/31/2024
Scott Aaronson — Quantumania (EP.240)
My guest today is Scott Aaronson, a theoretical computer scientist, OG blogger, and quantum computing maestro. Scott has so many achievements and credentials that listing them here would take longer than recording the episode. Here's a select few: Self-taught programmer at age 11, Cornell computer science student at 15, PhD recipient by 22! Schlumberger Centennial Chair of Computer Science at The University of Texas at Austin. Director of UT Austin's Quantum Information Center. Former visiting researcher on OpenAI's alignment team (2022-2024). Awarded the ACM prize in computing in 2020 and the Tomassoni-Chisesi Prize in Physics (under 40 category) in 2018. … you get the point. Scott and I dig into the misunderstood world of quantum computing — the hopes, the hindrances, and the hucksters — to unpack what a quantum-empowered future could really look like. We also discuss what makes humans special in the age of AI, the stubbornly persistent errors of the seat-to-keyboard interface, and MUCH more. I hope you enjoy the conversation as much as I did. For the full transcript, some highlights from Scott’s blog, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!” check out our . Important Links: (Scott’s blog) Show Notes: So much reading. So little time. The problem of human specialness in the age of AI It’s always the same quantum weirdness Why it’s easy to be a quantum huckster Quantum progress, quantum hopes, and quantum limits Encryption in a quantum empowered world Wielding the hammer of interference Scientific discovery in a quantum empowered world Bureaucracy and blank faces Scott as Emperor of the World MORE! Books Mentioned: The Fifth Science; by ****Exurb1a The Hitchhiker’s Guide to the Galaxy; by Douglas Adams
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Danny Crichton — Player of Games (EP.239)
10/24/2024
Danny Crichton — Player of Games (EP.239)
Danny Crichton is a man of many talents. He’s got a background in computer science, has worked in the worlds of foreign policy, was a managing editor at Techcrunch, and now serves as Head of Editorial at Lux Capital. As Lux’s de-facto games master, Danny also devises their Riskgames: strategic simulations that immerse players in complex scenarios reflecting real-world challenges and dynamics. These games – whose players include senators, major generals, congressmen and, think-tank CEOs – include scenarios like ‘Hamptons at the Cross-Roads’ (that deals with climate change and maritime security) and ‘Powering Up’ (that deals with China’s global EV dominance). Danny and I discuss the origins of Riskgaming and the lessons he’s learned in high-stakes games with tech founders and government officials. Plus, we riff on our shared Minnesotan roots, and discuss ways to combat the uncertain fog of war in our careers. I hope you enjoy this insightful 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 . Important Links: Show Notes: Origins of Riskgaming The Different Play Styles between Technologists and Policymakers One-off games vs. Iterative games The Game Theoretic Foundations of Riskgaming It’s All About Tough Decisions Parable of the First Mover Disadvantage The Importance of Incentives Why Insurance Companies are Obsessed with Truth in the Market How AIs Can Cut Through Bureaucratic Slog How Danny Builds Scenarios Why Riskgaming Teaches Better Decision Making Danny’s Thoughts on Intellectual Humility Danny and Jim’s Minnesotan Heritage Danny’s experience launching TechCrunch+ Facing the Fog of War The Importance of Agility Danny as Emperor of the World Books Mentioned: Gödel, Escher, Bach: An Eternal Golden Braid; by Douglas Hofstadter Left Behind: A New Economics for Neglected Places; by Paul Collier
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Yuk Chi Chan — On Rockets, Dog Years & Robotic Space-Snakes (EP.238)
10/17/2024
Yuk Chi Chan — On Rockets, Dog Years & Robotic Space-Snakes (EP.238)
My guest today is the human Swiss Army Knife, Yuk Chi Chan, who has packed more into the last decade than many people do in a lifetime. Yuk Chi is the founder of Charter Space, the first British space company to graduate from the Techstars Space Accelerator. Before that, he served as an officer in the Singapore army (hmm, so maybe I should have described him as a Singaporean Army Knife) and practiced as a space lawyer (it’s funny how much cooler being a lawyer becomes when you preface it with the word “space”). Suffice to say, Yuk Chi knows a lot about space. We had a blast discussing how ‘ownership’ of territory really works, why the sector impacts our daily lives FAR more than we think, and the mind-boggling mission of an intrepid robotic space snake. I hope you enjoy the 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 . Important Links: Show Notes: Yuk Chi Chan: The human Swiss Army Knife The strangely antiquated tools of the space industry Military training, problem-solving, and reframing the challenge The single most important trait in a co-founder Unlearning, cyclical culture, and robotic space snakes The labyrinthine world of space insurance Who owns space? The angry man on Yuk Chi’s shoulder Why Yuk Chi measures his life in dog years Space insurance as Zeno’s Paradox Why the space industry is WAY more ubiquitous than you think Yuk Chi as emperor of the world MORE! Books Mentioned: Flow My Tears, the Policeman Said; by Philip K. Dick Ubik; by Philip K. Dick
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Dan Shipper — I, Writer (EP.237)
10/10/2024
Dan Shipper — I, Writer (EP.237)
“Ignoring what is obvious incurs a huge cost. It requires you to go about your day numbing yourself to the reality of who you are and what you want—which is a waste of time for you and everyone around you. By contrast, admitting what is obvious is freeing and motivating. But it’s terrifying to do it. Sometimes the most obvious truths about ourselves are hard to see because the consequences of those truths seem so dire.” Those are the opening lines of one of my I’ve read in the last year, written by this week’s guest on Infinite Loops - Dan Shipper. Dan is the Co-founder and CEO of Every, a media company that wants to be an intellectual lighthouse amidst the tempest that is the Age of AI. Every began life in 2020 as a bundle of digital newsletters (almost like a centralised version of Substack with more of an editorial flourish). These days, it’s blossomed into an ecosystem of colourful newsletters, podcasts, courses, and software products, all oriented around the unpacking of a single question - Every is already one of my go-to destinations for all things interesting. It’s less brain food than brain buffet (the kind of buffet that serves fresh blueberry pancakes with real maple syrup). In our conversation, Dan shares his thoughts on everything from AI companions; his approach to erecting the Every ‘Pyramid’; his playbook for building new media companies; the idea of LLMs as mirrors for humanity; and using content to ‘find your people’. What I love about him is how candidly and thoughtfully he talks about his journey to discover his own truth. His realisation that he didn’t need to hang up his boots as a writer in order to become a founder is something that particularly hit home for me. Dan Shipper is also my underdog pick to eventually wrest the title of from reigning clubhouse leader Alex Danco. By which I mean to say, this is most certainly not the last time Dan joins us on the show, so you may as well get to know him better. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our . Important Links: Show Notes: Dan’s Superhero Origin Story Writers as Founders What Would You Pay To Do? The Every Pyramid The New Media Playbook How To Find Your People Our AI Mirrors From Explanation Problems to Engineering Problems On Intuition From The Knowledge Economy To The Allocation Economy The Reluctance To AI Adoption AI Companions Dan, The Emperor of The World Books and Articles Mentioned: ; by Dan Shipper ; by* Howard Bloom ; by Dan Shipper ; by I. F. Stone ; by ****Joseph Heinrich ; by Alexandre Dumas
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Dr. Gena Gorlin — How to Build a Builder (EP.236)
10/03/2024
Dr. Gena Gorlin — How to Build a Builder (EP.236)
My guest today is Dr. Gena Gorlin, a psychologist specializing in the unique needs of the ultra-ambitious. Unlike many in her field. Gena doesn’t aim to simply lift the floor of her clients’ ambitions — she wants to raise the ceiling. In this episode, she breaks down the “Builder Mindset” - a way of thinking that empowers people to live to healthier, happier, and more fulfilled lives. Over on our , we dig deeper into Gena’s ideas, exploring the perils of perfectionism, the allure of complacency, and why psychological perfection might be more achievable than you think. Important Links: (Gena’s Substack) Show Notes: The Unique Needs of the Ultra Ambitious Death is the Default The Rigid Authoritarianism of Your Inner Drill Sergeant The Sweet, Stagnant Embrace of the Zen Master Agency & the Enlightenment Historical Ignorance as a Bottleneck Human Beings as the Base Unit of Action Fight, Flight or Freeze How to Build a Builder Perfectionism is not Perfect What to Do When Surrounded by C Players Persistence, Passion & Personality Reframing FTW Gena as Empress of the World MORE! Books Mentioned: The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; by John D. Gartner
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Nir Eyal — How To Become An Indistractable Force (EP.235)
09/26/2024
Nir Eyal — How To Become An Indistractable Force (EP.235)
“Most people don’t want to acknowledge the uncomfortable truth that distraction is always an unhealthy escape from reality.” My latest guest, , writes, consults, and teaches about the intersection of , technology, and business. Nir previously taught as a at the Stanford Graduate School of Business and the Hasso Plattner Institute of Design at Stanford. In our conversation, Nir gives it to us straight. Distraction is killing us, and stopping us from reaching our full potential. In a world that is constantly conspiring to keep us distracted, Nir provides an alternative: we can take back control. We can regain our agency. All of these ideas are presented in his book, (co-authored with Julie Li). This book is a clear guide to understanding the psychology behind our impulses and is chock-full of great anecdotes and peer-reviewed studies to help you better manage your time, and your life. Nir’s framework is not only interesting, it is practical, so I suggest you check out our , where you’ll find the episode transcript and some actionable takeaways. I also encourage you to buy Nir’s excellent book and start applying his strategies to your own life. I hope you enjoy our conversation as much as I did! Important Links: Show Notes: What Being Indistractable Is All About Etymology of the Word Distraction The Strong Pull of Internal Triggers The Tyranny of the To-Do List The Difference Between High Performers and Low Performers The Dangers of Labelling Ourselves Using the Psychology of Identity Using Self-Determination Theory to Diagnose Distraction The Perils of Snowplow Parenting Believe the Good Science Nir as Emperor of the World Books / Articles Mentioned: ; by Nir Eyal (+ ) Nir’s articles on , , and Free to Learn: Why Unleashing the Instinct to Play Will Make Our Children Happier, More Self-Reliant, and Better Students for Life; by Peter Gray
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