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