If you’ve heard me speak for more than five minutes you’ve probably caught me dropping a Robert Anton Wilson reference (or several). Wilson is one of the most interesting (and underappreciated) writers I’ve ever come across — a Nostradamus for modern times. I was delighted to sit down with Gabriel Kennedy, author of the excellent biography Chapel Perilous: The Life and Thought Crimes of Robert Anton Wilson . I could talk about this stuff for days, and we had a blast discussing Wilson’s ideas, in...
Mar 06, 2025•1 hr 27 min•Ep 258•Transcript available on Metacast Christine Benz is the Director of Personal Finance and Retirement Planning at Morningstar, where she has spent over three decades helping investors navigate the complexities of financial planning. She is also the author of "How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement" and serves as the president of the John C. Bogle Center for Financial Literacy. Before focusing on retirement planning, Christine worked as a fund analyst, bringing a unique perspective that combines d...
Feb 27, 2025•1 hr 13 min•Ep 257•Transcript available on Metacast Luke Fehily is the Director of Innovation Policy at Progress Ireland — an independent think tank backed by the likes of the Collison brothers — that’s on a mission to connect Ireland to proven policy solutions from around the world. Before joining Progress Ireland, Luke cut his teeth in both public and private sectors, developing a unique perspective on how to navigate bureaucratic challenges while maintaining ambitious visions for change. His current work spans housing, infrastructure, and inno...
Feb 20, 2025•1 hr 11 min•Ep 256•Transcript available on Metacast Rudy Havenstein is a writer and satirist known for his sharp critiques of America’s sprawling institutions and the elites who run them. He joins the show to discuss the accountability crisis in America — how it manifests across political life and, most importantly, what we can do to fix it. Important Links: Rudy’s Twitter Rudy’s Substack Show Notes: Why we should fear hyperinflation “The Fed is Congress’ drug dealer” The Great Financial Crash & America’s accountability crisis How to disagree agr...
Feb 13, 2025•2 hr 40 min•Ep 255•Transcript available on Metacast Mark Daniel is the co-founder and managing partner of the investment firm Digital, whose portfolio extends across accelerated computing, gaming, crypto, social networking, AI, extended reality, cybersecurity, creator tools, spatial computing, and immersive learning. Back in 2013, he was also one of the very first recipients of a Thiel Fellowship. This was a fun one. Mark joins the show to discuss why podcasts are dangerous (😬), why content creators should have a 10 post limit, how he identifies...
Feb 06, 2025•1 hr 27 min•Ep 254•Transcript available on Metacast John Kennedy, a director at the Corsi-Rosenthal Foundation, is tackling an overlooked crisis in American education: air quality. With the ingenious use of a simple $60 box fan, he's on a mission to revolutionize the health and learning environments of students nationwide. It's mind-boggling how much low-hanging fruit there is here. The difference that clean air makes to health and brain capacity is enormous, and it's a surprisingly cheap problem to fix. In fact, as you'll hear about halfway thro...
Jan 30, 2025•1 hr 11 min•Ep 253•Transcript available on Metacast Michael Strong has spent decades quietly revolutionizing education by designing innovative schools and programs built around agency, critical thinking, entrepreneurship and creativity. He is the founder and CEO of The Socratic Experience, a virtual school that equips students for lifelong happiness and success through Socratic dialogue. Alongside his work in the US, he has educational consulting experience in multiple developing nations. And… he’s a fellow Minnesotan! Michael joins the show to d...
Jan 23, 2025•2 hr 32 min•Ep 252•Transcript available on Metacast Sahil Bloom, a prolific creator, founder and investor, has mastered the art of translating complex ideas about wealth and success into wisdom that resonates with millions. His newsletter, The Curiosity Chronicle, grew from just 100 readers to over 800,000 subscribers in three years - a testament to his ability to cut through the noise with clarity and insight. His upcoming book, "The 5 Types of Wealth," challenges our conventional understanding of what it means to be truly wealthy, arguing that ...
Jan 16, 2025•1 hr 9 min•Ep 251•Transcript available on Metacast Seth Stephens-Davidowitz, a data scientist and bestselling author, is known for his brilliant use of data to upend conventional wisdom - often with humorous, surprising, and occasionally shocking results. His latest book, Who Makes the NBA, uses data to interrogate some of basketball’s biggest questions, consistently yielding unexpected insights. Here’s the kicker - he wrote the entire book in just 30 days after discovering Code Interpreter. Unsurprisingly for a former quant, I had a blast chatt...
Jan 09, 2025•1 hr 25 min•Ep 250•Transcript available on Metacast Julian Gough sums up his career as follows: “ I just sit in my room and write.” Well, I think being an acclaimed children’s author, novelist, stage playwright, poet and top-ten Irish musician is a little more impressive than he’s letting on… Oh, and I didn’t even mention that he wrote the ending to the computer game Minecraft! His current project, The Egg and The Rock, puts all of this to shame. This book, which Julian is writing in public on Substack, seeks to do no less than redescribe the uni...
Jan 02, 2025•2 hr 42 min•Ep 249•Transcript available on Metacast Ben Reinhardt is the founder of Speculative Technologies “ a nonprofit industrial research lab that’s working to unlock a wonderful, abundant future through technologies that don’t have a home in other institutions.” He has previously worked at NASA and Bay Area startups/VC firms, founded a startup building robotics for eldercare, and helped entrepreneurs start companies in Singapore. Oh, and he has a Ph.D. in space robotics from Cornell University and is one of the few people with a B.Sc . in h...
Dec 26, 2024•1 hr 20 min•Ep 248•Transcript available on Metacast 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...
Dec 19, 2024•1 hr 15 min•Ep 247•Transcript available on Metacast 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 l...
Dec 12, 2024•1 hr 20 min•Ep 246•Transcript available on Metacast 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...
Dec 05, 2024•1 hr 15 min•Ep 245•Transcript available on Metacast 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 fr...
Nov 28, 2024•2 hr 31 min•Ep 244•Transcript available on Metacast 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 S...
Nov 21, 2024•1 hr 25 min•Ep 243•Transcript available on Metacast 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 i...
Nov 14, 2024•1 hr 10 min•Ep 242•Transcript available on Metacast 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 k...
Nov 07, 2024•1 hr 28 min•Ep 241•Transcript available on Metacast 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 r...
Oct 31, 2024•1 hr 12 min•Ep 240•Transcript available on Metacast 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 – includ...
Oct 24, 2024•1 hr 24 min•Ep 239•Transcript available on Metacast 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 th...
Oct 17, 2024•1 hr 28 min•Ep 238•Transcript available on Metacast “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 l...
Oct 10, 2024•1 hr 26 min•Ep 237•Transcript available on Metacast 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 com...
Oct 03, 2024•2 hr 44 min•Ep 236•Transcript available on Metacast “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 reach...
Sep 26, 2024•1 hr 10 min•Ep 235•Transcript available on Metacast 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 , whe...
Sep 19, 2024•1 hr 28 min•Ep 234•Transcript available on Metacast 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 eno...
Sep 12, 2024•2 hr 33 min•Ep 233•Transcript available on Metacast 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 wort...
Sep 05, 2024•2 hr 31 min•Ep 232•Transcript available on Metacast “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 transcr...
Aug 29, 2024•2 hr 40 min•Ep 231•Transcript available on Metacast 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 in...
Aug 22, 2024•1 hr 25 min•Ep 230•Transcript available on Metacast 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 sh...
Aug 15, 2024•2 hr 40 min•Ep 229•Transcript available on Metacast 
