Jim O'Shaughnessy

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!"

Author

Jim O'Shaughnessy

Category

Technology

Podcast website

infiniteloopspodcast.com

Latest episode

Jul 9, 2026

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Episodes

Luca Dellanna — How to Play (and Win) Long Term Games (EP.228) 08.08.2024

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 You...

Ateet Ahluwalia — The Many Bosses of a Venture Capitalist (EP.227) 01.08.2024

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...

Audrey Wisch — How to Cultivate Curious Kids (EP.226) 25.07.2024

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 abou...

Matthew Ball — Into The Metaverse (EP.225) 18.07.2024

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. T...

Nat Eliason — Crazy, Crypto, Confidential (EP.224) 11.07.2024

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 financia...

Noor Siddiqui — A Thiel Fellow's Guide to Having Healthy Babies (EP.223) 04.07.2024

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...

The Fourth Way - Mastering The Self (EP.222) 27.06.2024

The Fourth Way is a pseudonymously run Youtube channel and Twitter page dedicated to the path of psychological and spiritual growth and self-improvement. Built around the philosophy of two thinkers - George Gurdjieff and Peter Ouspensky - the ultimate aim of the Fourth Way is "to assist individuals in achieving a higher state of consciousness and self-awareness which can lead to a more fulfilling...

Mona Sobhani — A Neuroscientist's Journey From Materialism to Beyond (EP.221) 20.06.2024

Mona Sobhani, Ph. D. is a cognitive neuroscientist, researcher, and author. In 2022 she published her first book, Proof of Spiritual Phenomena: A Neuroscientist's Discovery of the Ineffable Mysteries of the Universe, which documents her " transformation from diehard materialist to open-minded spiritual seeker." Mona joins the show to discuss blowing open the box of materialism, why anecdotes are s...

Ellen Fishbein — Make Art, Not Noise (EP. 220) 13.06.2024

Described by David Perell as " like Rick Rubin for writing, " Ellen Fishbein is an author and writing coach and the founder of Altamira Studio, an independent publisher specializing in short-form books. She joins the show to discuss how traditional publishing disrespects intelligent readers, her advice for aspiring authors, what she's learned from Shakespeare's sonnets, and MUCH more! Important Li...

John A. Paulos — Avoiding Innumeracy (EP. 219) 06.06.2024

Professor, Mathematician and Writer John A. Paulos joins the show to discuss math education, the power of puzzles, cognitive biases, and MUCH more! Important Links: John's Website John's Twitter Show Notes: Why Do People Hate Math? The Power of Posing Problems with Counterintuitive or Shocking Results Using Everyday Examples to Understand Math Concepts Systems Designed to Take Advantage of Innumer...

Chris Wilcha — Flipside (EP.218) 30.05.2024

Chris Wilcha is an award-winning documentary filmmaker and commercial director. His latest film, Flipside, which is co-executive produced by Jim and presented in association with Infinite Films (among others), opens in select US theaters tomorrow (May 31st, 2024). An ode to creative failure, abandoned projects, and rekindled passion, Flipside premiered at the 2023 Toronto International Film Festiv...

Bridget Phetasy — Comedy is Dead, Long Live Comedy (EP.217) 23.05.2024

"PHETASY IS a movement disguised as a company. We just want to make you laugh while the world burns." Bridget Phetasy is an entrepreneur, writer, podcast host, political commentator, burgeoning media mogul, and standup comedian. Over the past few years, her media company - Phetasy - has become an outlet for 100s of hours of social commentary filtered through her sharp and spiky worldview. She join...

Porter Braswell — Building the Future of Leadership (EP.216) 16.05.2024

  Porter Braswell is the Founder and CEO of 2045 Studio, an exclusive network for accomplished professionals of color. Porter is also the Co-founder and Executive Chairman of the career advancement platform Jopwell, the host of the Harvard Business Review podcast Race at Work , and the author of two books, including 2019's Let Them See You . Porter joins the show to discuss how 2045 Studio is harn...

Grant Mitchell — The Potential of AI Drug Repurposing 09.05.2024

Grant Mitchell is a seasoned entrepreneur, operator, and investor in the areas of health, technology, and machine learning. He is currently the co-founder and CEO of Every Cure, where he uses AI to research rare diseases and conduct drug repurposing. Grant joins the show to discuss the use of AI in rare drug research, the role of translational scientists, neglected knowledge, and MUCH MORE! Import...

Jimmy Soni — The Courage of Creative Risk (EP.214) 02.05.2024

Author and friend-of-the-show Jimmy Soni returns to discuss the future of publishing, the changing world of book marketing, the courage of creative risk, and MUCH more! Important Links: Jimmy's website Jimmy's Twitter The Great Reshuffle Show Notes: Why Traditional Publishing is in Stasis A Case of Broken Incentives The Changing World of Book Marketing & the Case for Patience Talent Spotting & Cre...

Arjun Khemani — The Hunt for Better Problems (EP. 213) 25.04.2024

Arjun Khemani is a 17-year-old writer and podcaster who dropped out of high school to help lead support at Airchat, the social network co-founded by Naval Ravikant. As the host of the Arjun Khemani podcast, Arjun has spoken to a wide range of guests including David Deutsch, David Perell and Naval Ravikant. His Substack, Progress Good, " serves as a defense against the anti-Enlightenment tradition,...

Eddy Elfenbein — On Crossing Wall Street (EP. 212) 18.04.2024

Eddy Elfenbein is an OG finance blogger, ETF manager, and FinTwit legend, with over 25 years of experience working in and around Wall Street. Eddy joins the show to discuss the story behind his longtime blog -  Crossing Wall Street  (CWS), the origins of his famous Buy List, his ETF journey, his philosophy as an investor, and much more! Important Links: Eddy's Twitter Eddy's Blog (Crossing Wall St...

Anna Gát — We Digress (EP. 211) 10.04.2024

Friend-of-the-show Anna Gát returns to discuss… well… pretty much everything! On April 13th,  O'Shaughnessy Ventures  and  Interintellect  are co-hosting a Future of Publishing event at the beautiful Pratt Mansion in NYC. We're bringing together established publishers, online writers, new publishing houses, journalists, technologists, authors and more to rethink and reimagine how ideas are spread...

Visakan Veerasamy — Expanding Our Possibility-Space (EP. 210) 04.04.2024

The inimitable Visakan Veerasamy returns for a characteristically wide-ranging discussion… Important Links: Visa's Website Visa's Twitter   Visa's Youtube Visa's Previous Episode Visa's Post-Episode Thread Show Notes: Life as a Dad A Conversation With David Deutsch Change, Courage, Curiosity & Creativity Possibility Space & the Problem of Wretchedness A Good Blog Post Can Change the World The Outd...

Brendan McCord — AI and the Philosophy of Technology 28.03.2024

Brendan McCord is the founder of Cosmos Institute — a non-profit dedicated to exploring the intersection of AI and philosophy. Brendan joins the show to discuss Cosmos' origins, the pursuit of philosophy as a technologist, the different schools of thought in AI, complex adaptive systems and MUCH more! Important Links: Brendan McCord's Reading List Cosmos Institute Substack Brendan's Twitter Show N...

Alex Komoroske — Complex Adaptivity All The Way Down (EP. 208) 21.03.2024

Alex Komoroske has spent his career studying, writing about, and working in complex adaptive systems. He has published multiple essays on topics like Schelling points in organizations, why debate should be collaborative, and how to ensure resilient growth in harsh environments. Alex has also worked as a product manager and in corporate strategy at Google and Stripe. Alex joins the show to discuss...

Cedric Chin — Accelerating Business Expertise (EP. 207) 14.03.2024

Cedric Chin is a writer, researcher and operator whose Commoncog newsletter is dedicated to finding useful, practical ways to accelerate business expertise. He joins us to discuss some of the most potentially transformative concepts he's uncovered, from the business expertise triad to naturalistic decision making. Important Links: Cedric's Website (Commoncog) Are You Ready for the Great Reshuffle?...

Devon Eriksen — Theft of Fire (EP. 206) 07.03.2024

Devon Eriksen always wanted to be a writer. As a child, he was persuaded to abandon his aspirations in favor of a career in software engineering. Two decades later, he retired to finally fulfil his ambition to write imaginative hard-science fiction in the vein of authors like Asimov, Heinlein and Niven. He self-published his first novel,  Theft of Fire , last year to an excellent reception. Devon...

Jacqueline Novogratz - Manifesto for a Moral Revolution 29.02.2024

Jacqueline Novogratz is the founder of Acumen, a nonprofit impact investment fund "changing the way the world tackles poverty by investing in companies, leaders and ideas." As well as founding Acumen in 2001, Jacqueline is a public speaker and best-selling author. She also sits on multiple philanthropic boards. Her latest book Manifesto for a Moral Revolution , " reveals 12 leadership practices fo...

Rupert Sheldrake — On Scientism, Morphic Resonance and the Extended Mind (EP. 204) 22.02.2024

Rupert Sheldrake is a biologist and author of 9 books and over 100 scientific papers. A critic of what he sees as the scientific establishment's dogmatic dedication to materialism, he is perhaps best known for his theory of "morphic resonance," via which information and activity can be transferred across space and time. Rupert joins the show to discuss being branded a heretic, how to test for tele...

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