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    Business

    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!”

    Advertise
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    • Google Play
    • Spotify

    Latest Episodes:
    Ben Orlin — Math As Universal Language (EP.232) Sep 05, 2024
    Show notes

    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

    Gurwinder Bhogal's Guide to Modern Survival (EP.231) Aug 29, 2024
    Show notes

    "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

    Julia Sonnevend — Charming! (EP.230) Aug 22, 2024
    Show notes

    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

    Bilawal Sidhu — How to Unite Reality With Imagination (EP.229) Aug 15, 2024
    Show notes

    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

    Luca Dellanna — How to Play (and Win) Long Term Games (EP.228) Aug 08, 2024
    Show notes

    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

    Ateet Ahluwalia — The Many Bosses of a Venture Capitalist (EP.227) Aug 01, 2024
    Show notes

    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

    Audrey Wisch — How to Cultivate Curious Kids (EP.226) Jul 25, 2024
    Show notes

    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

    Matthew Ball — Into The Metaverse (EP.225) Jul 18, 2024
    Show notes

    Matthew Ball is the CEO of Epyllion, which makes angel investments, provides advisory services, and produces television, films, and video games.

    He's also a Venture Partner at Makers Fund, Senior Advisor to KKR, Senior Advisor to McKinsey & Company, and sits on the board of numerous start-ups.

    Matthew is one of the sharpest and most original thinkers on the future of media and the Internet (i.e. The Metaverse). The fully revised and updated edition of his bestselling book "The Metaverse: Building the Spatial Internet" releases next week.

    Important Links:

    • Matthew's website
    • Matthew's Twitter

    Show Notes:

    • Into The Metaverse
    • AI and The Metaverse
    • 'AI Can Bend the Laws of Physics'
    • Human Engineering and the Human Brain
    • Screens and Education
    • The Reflexivity of AI Doomerism
    • The Salvation of the 'TV Species'
    • From Passive Media to Active Media
    • 'What's An Appropriate Simulation?'
    • 'We Don't Outlaw Fire, We Train Firemen'
    • Applying the Precautionary Principle
    • Media and the Metaverse: Three Stages of Competition
    • The Enduring Value of Taste
    • Hardware and AI: The Vergence-Accommodation Conflict
    • The Emperor of the Metaverse
    • MORE!

    Books Mentioned:

    • The Metaverse: Building the Spatial Internet; by Matthew Ball
    • The Streaming Book; by Matthew Ball
    • The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich

    Nat Eliason — Crazy, Crypto, Confidential (EP.224) Jul 11, 2024
    Show notes

    Nat Eliason is a writer with a keen interest in writing about challenging and revealing things. His debut book, Crypto Confidential: Winning and Losing Millions in the New Frontier of Finance (out July 9th, 2024), charts his personal odyssey into Crypto's Get-Rich-Quick underbelly.

    Nat joins the show to discuss the highs and lows of the cryptocurrency market, the lessons learned from his financial adventures, the psychological effects of bubbles, crypto's cutting-edge developments, and MUCH more!

    Important Links:

    • Nat's Website
    • Nat's Twitter
    • Nat's YouTube

    Show Notes:

    • Making A Lot of Money, As Fast as Possible
    • The Peer Pressure of Crypto Markets
    • The Psychological Effects of Diamond Hands
    • Signs of Peak Speculation
    • How Bitcoin Has Carried the Crypto Story
    • Ethereum's Innovations
    • The Emergence of Stablecoins
    • What Makes USD A Reserve Currency?
    • The Crazy Anonymity of Crypto Projects
    • The Two Options of Getting Into Crypto
    • Imagining the Money Pile
    • What Nat Couldn't Keep in the Book
    • Nat's Next Career as a Novelist
    • Nat as Emperor of the World
    • MORE!

    Books Mentioned:

    • Influence; by Robert Cialdini

    Noor Siddiqui — A Thiel Fellow's Guide to Having Healthy Babies (EP.223) Jul 04, 2024
    Show notes

    Noor Siddiqui is currently building Orchid, a reproductive technology company that measures genetic predisposition to disease and provides embryo screening for couples going through IVF.

    Noor joins the show to discuss the ambitious culture of the West Coast, getting into the Thiel Fellowship, her personal reasons for starting Orchid, the sacred act of reproduction and why it must be made safe, her belief in children as the future, and MUCH more!

    Important Links:

    • Noor's Personal Website
    • Noor's Twitter
    • Noor's Linkedin
    • Orchid's Website

    Show Notes:

    • The Ambitious Culture of San Francisco
    • The East Coast Aversion to Risky Ambition
    • The Intimate Origin Story of Orchid
    • What Orchid Has Built
    • The History and Controversy Around Reproductive Technology
    • Surprising Aspects of Orchid's Technology
    • Benefits of Saliva Testing
    • Making Our Own Genetic Luck
    • Noor's Predictions for the Field
    • Advances in Embryonic Freezing
    • Why Noor Values Clear Writing
    • Noor as Empress of the World
    • MORE!

    Books/Essays Mentioned:

    • What You Can't Say; by Paul Graham
    • Secrets (from Zero To One); by Peter Thiel

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