Stay ConnectedEvery 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!”
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.
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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.
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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:
… 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.
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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.
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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.
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"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.
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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.
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"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!
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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.
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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!
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