Infinite Loops

Jim O'Shaughnessy
  • 4.6 (164)
  • TECHNOLOGY
  • UPDATED WEEKLY
Infinite Loops Podcast

In a rapidly changing world, it's too easy to get trapped by the existing models. New problems are met with old solutions, leading to infinite loops of inaction. We're here to change that. By exploring ideas ranging from the Tao Te Ching to cutting-edge advances in AI, we will arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Infinite Loops is part of Jim’s new company, O'Shaughnessy Ventures. For in-depth syntheses of our guests' ideas, as well as for additional ideas that make you go Hmm that’s interesting!, subscribe to our Substack at https://infiniteloops.substack.com. Powered by O’Shaughnessy Ventures.

  1. 6 DAYS AGO

    Mike Maples, Jr. — How To Become a Pattern-Breaking Founder (EP.233)

    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

    1h 33m

  2. SEP 5

    Ben Orlin — Math As Universal Language (EP.232)

    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

    1h 31m

  3. AUG 29

    Gurwinder Bhogal's Guide to Modern Survival (EP.231)

    “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

    1h 40m

  4. AUG 22

    Julia Sonnevend — Charming! (EP.230)

    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

    1h 25m

  5. AUG 15

    Bilawal Sidhu — How to Unite Reality With Imagination (EP.229)

    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

    1h 40m

  6. AUG 8

    Luca Dellanna — How to Play (and Win) Long Term Games (EP.228)

    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

    1h 26m

  7. AUG 1

    Ateet Ahluwalia — The Many Bosses of a Venture Capitalist (EP.227)

    Let me introduce you to the four horsemen of the investment apocalypse: Fear. Greed. Hope. Ignorance. Notice anything? Three of four are emotions. I’ve long argued that effective investing is far more about emotional control than technical know-how (although the latter certainly helps!) By hook or by crook, the best investors can find a way to tame their pesky emotional impulses and overcome that primal urge to respond impulsively to panic, passion, or pride. My guest, the razor-sharp Ateet Ahluwalia, is a veteran trader and investor who has spent well over 15 years at the coalface, from trading at Goldman at the dawn of the financial crisis to his current role as founder and managing director of the venture capital firm Island Green Capital Management. As you’ll hear from our conversation, Ateet has built an insanely deep understanding of the emotional constitution required to succeed in finance and venture capital, which informs his approach to risk management, hiring, investing, due diligence, and everything in between. I hope you enjoy our wide-ranging conversation, whose implications extend well beyond investing. For episode takeaways, a full transcript, and various other goodies, check out our Substack. Important Links: The Thinker and The Prover; by Jim O’Shaughnessy Ateet’s LinkedIn Island Green Capital Management Show Notes: Why Venture Capitalists Should Shun the Glory “In a changing world, playing it safe is one of the riskiest things you can do." Risk: Why Size Matters The Emotional Constraints of Investing How to Find Out What Someone Really Wants The Purifying Power of Mistakes Pick up the Phone! Being Humbled by the Market Public vs Private Investing Why Hit Rates Matter Assessing the Macro Position Bullshitting, Question-Dodging, and Other Red Flags The Many Bosses of the Venture Capitalist Be a Painkiller Ateet as Emperor of the World MORE! Books Mentioned: The Enlightenment Trilogy; by Jed McKenna Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist; by Brad Feld & Jason Mendelson Financial Intelligence: A Manager’s Guide to Knowing What the Numbers Really Mean; by Karen Berman, Joe Knight & John Case Adventures of a Bystander; by Peter F. Drucker

    1h 21m

  8. JUL 25

    Audrey Wisch — How to Cultivate Curious Kids (EP.226)

    I’ve always tried to encourage curiosity in my three children and now six (!) grandchildren. My kids often reminisce about my default response to their childhood questions: pointing to the bookshelf that flanked our sofa and saying, “look it up in there!” Luckily, natural curiosity was never lacking in our household. Over the years, however, I have become increasingly frustrated when I hear about the stultifying, rote, curiosity-killing nature of our education system. It was a pleasure, therefore, to speak to Audrey Wisch, an impressive young founder who, after witnessing first-hand how kids’ curiosity was being crushed, decided to do something about it. She left Stanford University to build Curious Cardinals, a personalized service that matches children with university mentors. What started as a pandemic project has grown into something much bigger - Audrey and her co-founder were named to the 2022 Forbes 30 Under 30 List in education, and Curious Cardinals has now delivered over 20,000 hours of mentorship to over 2,000 kids. As you’ll hear in our conversation, Audrey’s approach to education is a breath of fresh air, focusing on agency and empowerment, meeting kids where their interests lie, and harnessing the benefits of technology. I hope you enjoy our conversation! For the full transcript alongside bucketloads of other stuff designed to make you go; “Hmm, that’s interesting!” check out our Substack. Important Links: Curious Cardinals LinkedIn Twitter Show Notes: The Classroom: Disengaging, Uninspiring and Regurgitating The Chicken Nugget Strategy: Learning Through Interests Are Attention Spans Shortening? Why Mentors Matter Rose, Bud, Thorn: How to Design an Effective Mentorship Session The Perks of Proximity The RBG Approach to Disruption Against a One-Size-Fits-All Approach Curiosity, Lifelong Learning & Openness to Change Shakespeare on Snapchat The Changing Role of Memory Prompting via Socratic Iteration; Tapping into the Why How Audrey Became Interested in AI Why the College System Restrains K-12 Progress Hiring for the Output vs Hiring for the Input Audrey as Empress of the World MUCH more! Books Mentioned: The Anxious Generation: How the Great Rewiring of Childhood is Causing an Epidemic of Mental Illness; by Jonathan Haidt Paper Belt on Fire: How Renegade Investors Sparked a Revolt Against the University; by Michael Gibson

    1h 14m
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4.6
out of 5
164 Ratings

About

In a rapidly changing world, it's too easy to get trapped by the existing models. New problems are met with old solutions, leading to infinite loops of inaction. We're here to change that. By exploring ideas ranging from the Tao Te Ching to cutting-edge advances in AI, we will arm you with the tools & fresh perspectives required to upgrade your HumanOS and thrive in our messy, probabilistic world. Infinite Loops is part of Jim’s new company, O'Shaughnessy Ventures. For in-depth syntheses of our guests' ideas, as well as for additional ideas that make you go Hmm that’s interesting!, subscribe to our Substack at https://infiniteloops.substack.com. Powered by O’Shaughnessy Ventures.

Information

  • Creator
    Jim O'Shaughnessy
  • Years Active
    2019 - 2024
  • Episodes
    234
  • Rating
    Explicit
  • Show Website
    Infinite Loops

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