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