Infinite Loops

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

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 Substack. Important Links: Sajith’s website Sajith’s Twitter Sajith’s Substack Blume VC’s Indus Valley Annual Report 2024 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: The Fortune at the Bottom of the Pyramid; by C. K. Prahalad Supercommunicators; by Charles Duhigg Career Advice; by Scott Adams The Indus Valley Report 2024; by Blume VC

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 Substack. Important Links: Shtetl-Optimized (Scott’s blog) My Reading Burden On blankfaces 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

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 Substack. Important Links: Danny's Twitter Danny's LinkedIn Danny's Personal Website Lux Securities Newsletter The Riskgaming Initiative 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

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 Substack. Important Links: LinkedIn Substack Twitter Charter Website Charter Twitter 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

“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 favourite essays 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 - “What comes next?” 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 Infinite Loops Emperor 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 Substack. Important Links: Dan’s Twitter Dan’s writing on Every Dan’s personal website 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: Admitting What Is Obvious; by Dan Shipper *The Global Brain: The Evolution of Mass Mind from the Big Bang to the 21st Century; by* Howard Bloom Against Explanations; by Dan Shipper The Trial of Socrates; by I. F. Stone The WEIRDest People in the World; by ****Joseph Heinrich The Three Musketeers; by Alexandre Dumas

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 Substack, 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 Website Building the Builders (Gena’s Substack) Gena’s Twitter 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

“Most people don’t want to acknowledge the uncomfortable truth that distraction is always an unhealthy escape from reality.” My latest guest, Nir Eyal, writes, consults, and teaches about the intersection of psychology, technology, and business. Nir previously taught as a Lecturer in Marketing 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, Indistractable: How to Control Your Attention and Choose Your Life (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 Substack, 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: Nir’s personal blog Nir’s LinkedIn Nir’s Twitter Nir’s YouTube channel Nir’s Habit Tracking Tool Nir’s Schedule Maker Tool Show Notes: What 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: Indistractable; by Nir Eyal (+ bonus content) Nir’s articles on Timeboxing, Values, FOMO and Wage slavery 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

As the saying goes, only three things in life are certain: death, taxes & Alex Danco. Armed with sizzling hot takes on the sad death of Twitter likes and a new secret weapon in the form of his catchphrase-turned-episode theme (“Without mystery, there is no margin”), Alex returns for his eighth episode. Despite our intentional lack of preparation, somehow this ended up as one our most cohesive conversations yet. As usual, we’ve included links and an episode transcript over on our Substack, where we’ve also made the foolhardy attempt to distil one overriding theme from eight episodes of fiercely unstructured, defiantly unplanned, proudly meandering conversation. Important Links: Twitter: https://twitter.com/Alex_Danco Website: https://alexdanco.com/ Previous episode: https://www.infiniteloopspodcast.com/alex-danco-on-self-delusion-sancho-panza-safe-words-seinfeld-ep156/ Show Notes: What the fuck is going on? & the sad death of Twitter likes Where are the journalists? Without mystery, there is no margin Why aesthetics are underrated Friction is good, actually Make things to gain agency Empowering small firms to access the mysterious margin Everything is positioning How to learn effectively Alex as emperor of the world MORE! Books Mentioned: The Fifth Science; by Exurb1a What Works on Wall Street: A Guide to the Best-Performing Investment Strategies of All Time; by Jim O’Shaughnessy The Gervais Principle, Or The Office According to “The Office”; by Venkatesh Rao The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom

Mike Maples, Jr., co-founding partner of the VC firm Floodgate, is the veteran seed investor behind some of the 21st-century’s great success stories, including Twitter, Twitch, and Applied Intuition. His book, Pattern Breakers (co-authored with Peter Ziebelman), articulates a new model of foundership, one built on the simple premise that transformative startups upend rather than improve current practices. My company, OSV, is built around my belief that the collapse of the old models presents enormous opportunities to those savvy enough to seize them, so I had a blast quizzing Mike on the nuts and bolts of pattern-breaking foundership, from finding true believers to waging asymmetric war on the status quo. If Mike’s theory sounds as interesting to you as it did to me, check out our Substack, where we’ve distilled some pattern-breaking insights and shared the episode transcript. I also encourage you to buy Mike’s excellent book. In the meantime, I hope you enjoy our conversation as much as I did! Important Links: Pattern Breakers: Why Some Start-Ups Change the Future; by Mike Maples, Jr & Peter Ziebelman Twitter Substack (Starting Greatness) Floodgate LinkedIn Show Notes: Seagull mode: an unexpected founder paradigm How to wage asymmetric war on the present Evading the comparison trap Finding your people: how to build a movement Why we should continually seek the truth The customer isn’t always right, but the ones living in the future are Why disagreeableness is undervalued How to fix a pitch Franckendeck Don’t use jargon as a substitute for clear thinking How to find the true believers How to live in the future How founders are like trainspotters Why wanting to be a founder is a bad reason to start a company Reading habits of a pattern-breaker The unreliability of memory Mike as emperor of the world MORE! Books Mentioned: Jonathan Livingston Seagull: A story; by Richard Bach The Genius of the Beast: A Radical Re-Vision of Capitalism; by Howard Bloom The Beginning of Infinity: Explanations that Transform The World; by David Deutsch What Works in Wall Street; by Jim O’Shaughnessy Poor Charlie’s Almanac: The Essential Wit and Wisdom of Charles T. Munger; by Charles T. Munger

As a former quant with six grandkids, my spidey-senses started tingling as soon as I heard about Ben Orlin’s mission to make math fun. A native of St.Paul, Ben is a math educator and popularizer who is known for his “Math With Bad Drawing” blog and book series. Today’s conversation revolves around his excellent, original new book Math for English Majors: A Human Take on the Universal Language, which reframes math as a language, complete with nouns, verbs and grammar. Like any mathematician worth his salt, Ben loves games, which he sees as ‘puzzle engines’. No wonder then that our conversation meandered and unfolded like a satisfying puzzle, touching upon rich concepts. We discussed making sense of sampling through fantasy towns where 70% of inhabitants are lawyers (not a town I’d like to be in), threw in a bit of Lewis Carroll to discuss the assumptions built into propositional logic (sometimes it really is turtles all the way down) and pitied the Welsh kids learning how to count (keep listening to know what that means). I hope you enjoy our conversation as much as I did! For more thoughts on the episode, the full transcript, and bucketloads of other stuff designed to make you go; “Hmm, that’s interesting!” check out our Substack. Important Links: Ben’s Blog Ben’s Twitter Ben’s LinkedIn Show Notes: A Mathematician’s Obsession The Language of Algebra What the Tortoise Said to Achilles The Concrete and the Abstract Games As Puzzle Engines We’re not Built to Understand Base Rates Why We Always Think About Samples Incorrectly Randomness and Wikipedia Rabbit-holing Counting in Different Languages The Concept of Zero Negatives as the Mathematical Language of Opposites Mathematical Escape Rooms Why Is the World Comprehensible? Discussing Infinity on Infinite Loops The Deep Mathematics of Music Ben As Emperor of the World Books Mentioned: Math for English Majors: A Human Take on the Universal Language; by Ben Orlin Math with Bad Drawings: Illuminating the Ideas That Shape Our Reality; by Ben Orlin Zero: The Biography of a Dangerous Idea; by Charles Seife Gödel, Escher, Bach: An Eternal Golden Braid; by Douglas Hofstadter Musicophilia: Tales of Music and the Brain; by Oliver Sacks

“We have created for ourselves a world that we didn't evolve for.” Gurwinder Bhogal is, for my money, one of the most independent, original and insightful thinkers you’ll find in our corner of the internet. He returns to discuss how willpower and good old-fashioned human agency can help us reclaim our mental sovereignty and escape the “constant avalanche of concerns that are being vomited over us through our laptop screens, our phones, our TV screens, and in conversations.” For the full transcript, episode takeaways, and bucketloads of other stuff designed to make you go, “Hmm, that’s interesting!” check out our Substack. Important Links: Gurwinder's Substack  Gurwinder's Twitter Gurwinder’s previous Infinite Loops appearance Show Notes: “We have created for ourselves a world we didn’t evolve for” The dogged persistence of our stubborn beliefs Gamification; generational differences in agency The societal impact of the education system’s changing priorities How to zombify a population Skin in the game: Gurwinder’s guide to reclaiming agency LLMs, bullshit, and the atomization of culture How to play better games Willpower is the bottleneck Gurwinder as emperor of the world MORE! Books Mentioned: Why Everything is Becoming a Game; by Gurwinder Bhogal Think Again: The Power of Knowing What You Don't Know; by Adam Grant The Status Game: On Human Life and How to Play It; by Will Storr The True Believer: Thoughts on the Nature of Mass Movements; by Eric Hoffer Why the Mental Health of Liberal Girls Sank First and Fastest; by Jonathan Haidt (After Babel) America’s Colleges Are Reaping What They Sowed; by Tyler Austin Harper (The Atlantic) Joe Biden and the Common Knowledge Game; by Ben Hunt (Epsilon Theory) The Emperor’s New Clothes; by Hans Christian Andersen Futarchy Details; by Robin Hanson (Overcoming Bias) The Enlightenment Trilogy; by Jed McKenna The Weirdest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich

Professor Julia Sonnevend believes that charm is one of the defining political trends of our era. In her latest book, she argues that charm will do no less than “shape the future of democracy worldwide,” exploring how it is weaponized by politicians ranging from Jacinda Arden to Kim Jong Un. In our episode, you will discover why charm has emerged as a political force and how to innoculate yourself when you encounter it in the wild. Julia and I also dig into the five components of a charming interaction, a tantalizing prospect for those of you who want to dabble in the dark arts yourself… For the full transcript, episode takeaways, and bucketloads of other stuff designed to make you go, “Hmm, that’s interesting!” check out our Substack. Important Links: Charm: How Magnetic Personalities Shape Global Politics Julia’s website Julia’s Twitter Show Notes: Why social scientists are scared of charm The beer test of political leadership Can charm be manufactured? How humor affects charm The five building blocks of charm Does writing a book about charm make you immune to charm? Suspicion of seduction Is personality damaging politics? The true arbiter of authenticity How to encourage students to think critically How global iconic events are constructed Historical villains & the banality of evil Charming or not-charming: a speed-round The transitory nature of the charm offensive The benefits of taking a moment Julia as Empress of the World

As a proud owner of the exceedingly rare “two-digit” designation on CompuServe (the internet’s precursor), I’ve always been an early adopter of new tech. I was, therefore, particularly excited to speak to Bilawal Sidhu, a one-man corporation whose prolific output outpaces many creators put together. Since he was 11, Bilawal has been passionate about using cutting-edge tech to create videos that unite reality with his imagination. He made his bones as a product manager at Google, but after his short-form videos generated millions of views on social media, he decided to go all-in on his creative projects, including this video showing ‘shadow aliens’ invading Miami Mall, which racked up 11M views in 24 hours (!) on TikTok. Bilawal is also an adept rune-reader in the tech industry — his Creative Digest newsletter and YouTube channel offer insights and analysis on tech and market developments, while his TEDAI podcast broke the recent Helen Toner x OpenAI story. If you’re a creator curious about the opportunities presented by cutting-edge tech, you’re gonna love this episode. For the full transcript and bucketloads of other stuff designed to make you go, “Hmm, that’s interesting!” check out our Substack. Important Links: Bilawal’s Website (includes links to all social channels) What Does “Rat Park” Teach Us About Addiction? (Psychiatric Times) Show Notes: Aliens at the Miami Mall & the deep fake arms race How to unite reality with imagination The three waves of content democratization & the incoming content tsunami Artisan vs organic content Creation by proxy Climbing up the adoption curve Bilawal’s idea-to-execution creation process Remix culture & co-creation Competing visions of an AI-infused feature Finding an economic model that benefits indie creators Sovereign AI & being long human creativity Bilawal as Emperor of the World MORE! Books Mentioned: The Fifth Science; by Exurb1a The Hitchhiker’s Guide to the Galaxy; by Douglas Adams The God Problem: How a Godless Cosmos Creates; by Howard Bloom The Ultimate Resource; by Julian L. Simon

When Luca Dellanna speaks, I listen. Unlike many of the other management, productivity and behavioral gurus out there, Luca is ruthlessly committed to providing actionable, tangible advice that is rooted in the messy, chaotic reality of daily life. This conversation, my second with Luca, revolves around his excellent new book, Winning Long-Term Games: Reproducible Success Strategies to Achieve Your Life Goals. Why should you care? Because long-term strategies consistently deliver better results. In other words, being able to identify, play, and win long-term games is, quite literally, the secret to success. With examples ranging from NASA janitors to Stonehenge spray painters, we discuss how to successfully identify reproducible long-term strategies and how to persuade others to get on board with them. We also explore how hypotheticals can be an insanely powerful tool for ensuring our short-term actions remain consistent with our long-term goals (and yes, before you ask, my beloved premeditation makes an appearance). I hope you enjoy our conversation as much as I did! For more thoughts on the episode, the full transcript, and bucketloads of other stuff designed to make you go; “Hmm, that’s interesting!” check out our Substack. Important Links: Winning Long-Term Games: Reproducible Success Strategies to Achieve Your Life Goals Luca’s Website Luca’s Twitter Luca’s Previous Episode Five Counterintuitive Truths We Learned From Luca Dellanna Show Notes: The Tale of the Three Bricklayers Tighten Up Those Feedback Loops The Perils of Short-Term Thinking How to Signal Long-Term Intentions Reproducibility is King The Mighty Power of the Humble Hypothetical Concretizing the Abstract Goldilocks Solutions Extracting Tangible Benefits From Stratospheric Objectives Intuition & Luck in Long-Term Games Risk of Tactic vs Risk of Strategy; Flexible North Stars Build Your Own Long-Term Company Tesla’s Risky Success Luca as Emperor of the World MORE! Books Mentioned: Winning Long-Term Games: Reproducible Success Strategies to Achieve Your Life Goals; by Luca Dellanna The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich The Hitchhiker’s Guide to the Galaxy; by Douglas Adams Antifragile: Things that Gain from Disorder; by Nassim Nicholas Taleb The Infinite Game: How Great Businesses Achieve Long-Lasting Success; by Simon Sinek