Jim O'Shaughnessy on Creativity, Crisis, and Trust as The Fabric of Society

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Mar 29, 2025

Jim O'Shaughnessy, a renowned investor and founder of O'Shaughnessy Ventures, dives into creativity and trust in today’s complex world. He shares personal anecdotes about overcoming challenges and how childhood experiences shaped his financial passions. The conversation touches on the 'crisis personality' and the resilience that emerges from tumultuous times. Jim also examines the impact of technology on human agency and social interactions, questioning how trust evolves in our rapidly changing society. His insights inspire curiosity, collaboration, and reflection.

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ANECDOTE

Sister's Passing and Crisis Personality

At age 10, O'Shaughnessy's older sister passed away, profoundly impacting him.
This event contributed to the development of his "crisis personality," characterized by calmness in challenging situations.

ANECDOTE

Grandfather's Philanthropy

Jim O'Shaughnessy's grandfather, a successful oilman, instilled in him the value of philanthropy.
He gave away most of his fortune, believing that wealth should be spread like fertilizer.

ANECDOTE

Early Interest in Investing

O'Shaughnessy developed an early interest in Wall Street and investing.
He questioned his father and uncle's investment approach, suggesting a focus on underlying business factors.

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Gödel, Escher, Bach

An Eternal Golden Braid

Douglas Hofstadter

This book by Douglas Hofstadter is a comprehensive and interdisciplinary work that explores the interrelated ideas of Kurt Gödel, M.C. Escher, and Johann Sebastian Bach. It delves into concepts such as self-reference, recursion, and the limits of formal systems, particularly through Gödel's Incompleteness Theorem. The book uses dialogues between fictional characters, including Achilles and the Tortoise, to intuitively present complex ideas before they are formally explained. It covers a wide range of topics including cognitive science, artificial intelligence, number theory, and the philosophy of mind, aiming to understand how consciousness and intelligence emerge from formal systems[2][4][5].

One Summer

America, 1927

Bill Bryson

In 'One Summer: America, 1927', Bill Bryson chronicles the significant events of the summer of 1927 in the United States. The book covers a range of topics including Charles Lindbergh's nonstop transatlantic flight, the Great Mississippi Flood, Babe Ruth's record-breaking baseball season, the transition from the Ford Model T to the Model A, the execution of Sacco and Vanzetti, and the advent of talking pictures with 'The Jazz Singer'. Bryson also explores the contrast between the Roaring Twenties and the looming Great Depression, providing a vivid and humorous narrative of daily life and popular culture during that pivotal summer.

Invest Like the Best

How the Best Investors Approach the Market

Patrick O'Shaughnessy

Patrick O'Shaughnessy's "Invest Like the Best" is a compilation of interviews with some of the world's most successful investors. The book explores a wide range of investment philosophies and strategies, offering insights into the decision-making processes of these experts. O'Shaughnessy delves into various topics, including value investing, growth investing, and behavioral finance. The book provides a diverse perspective on the investment world, highlighting the importance of adaptability and continuous learning. It's a valuable resource for investors seeking to expand their knowledge and refine their investment approach.

What works on Wall Street

The Classic Guide to the Best-Performing Investment Strategies of All Time

James P. O'Shaughnessy

In 'What Works on Wall Street', James P. O'Shaughnessy provides an in-depth analysis of over 90 years of stock market data to identify the most effective investment strategies. The book examines various factors such as price-to-earnings ratios, price-to-sales, price-to-book value, dividend yields, and more. It challenges conventional wisdom and offers multifactor strategies that have historically generated the best returns. The book is designed to help investors of all levels, from conservative to aggressive, in selecting the best strategies for their investment objectives.

The Status Game

Will Storr

Tao te ching

Laozi

The Tao Te Ching is a central text in Taoist philosophy and religion. It consists of 81 brief chapters or sections that discuss the nature of the Tao, which is described as the source and ideal of all existence. The text emphasizes living in harmony with nature, the importance of simplicity, humility, and the interconnectedness of all things. It critiques unnatural actions and social activism based on abstract moralism, advocating for a life of 'nonaction' (wu wei) and spontaneity. The text has been highly influential in Chinese philosophy and has been translated numerous times, making it one of the most translated texts in world literature[2][3][4].

Finite and infinite games

James P. Carse

In this book, James P. Carse distinguishes between finite and infinite games. Finite games are instrumental activities with clear rules, boundaries, and winners, such as sports, politics, and wars. Infinite games, on the other hand, are authentic interactions that aim to continue the play, changing rules and boundaries as needed. Carse explores how these concepts apply to various aspects of life, including culture, religion, sexuality, and self-discovery. He argues that finite games offer wealth, status, and power, while infinite games provide something more subtle and grander, such as true freedom and endless possibility. The book offers insights into how approaching life as either a finite or infinite game affects one's choices, satisfaction, and success[2][4][5].

The master and his emissary

The Divided Brain and the Making of the Western World

Iain McGilchrist

This book argues that the division of the brain into two hemispheres is essential to human existence, allowing for two incompatible versions of the world. The left hemisphere is detail-oriented, prefers mechanisms to living things, and is inclined to self-interest, while the right hemisphere has greater breadth, flexibility, and generosity. McGilchrist takes the reader on a journey through the history of Western culture, illustrating the tension between these two worlds as revealed in the thought and belief of thinkers and artists from ancient to modern times. He argues that the increasing dominance of the left hemisphere in today’s world has potentially disastrous consequences.

Scale Theory

A Nondisciplinary Inquiry

Joshua DiCaglio

In 'Scale Theory', Joshua DiCaglio presents a nondisciplinary approach to understanding scale, which challenges traditional nonscalar interpretations. The book uses six thought experiments to clarify and redefine scale, discussing how it transforms objects, subjects, and relations. It integrates various disciplines from nanoscience to ecology and humanities, including philosophy and rhetoric. DiCaglio examines the transformative power of scale, its cognitive dimensions, and its implications on our worldview, also exploring the connection between scale and mysticism. The book addresses the complexities of scale in communication, rhetoric, and representation, drawing on both Western and non-Western concepts.

From Nowhere

Artists, Writers, and the Precognitive Imagination

Eric Wargo

Power and Influence

Beyond Formal Authority

John P. Kotter

This week Jim O’Shaughnessy (Website | X) joins Humans On The Loop to carry our first on-record conversation on Infinite Loops into bold new terrains! Jim is one of the most renowned investors and asset managers of all the time and the author of several hugely best-selling and influential books on investing, including What Works on Wall Street, Invest Like The Best, and Predicting The Markets of Tomorrow. He also founded the first online investment advisor and holds the patent for “ the origination and fulfillment of stock investment portfolios over a worldwide computer network.” (You heard right!)

After decades of success in wealth management, he left his company in the care of his son Patrick and launched O’Shaughnessy Ventures — a firm that combines “Jim’s deeply rooted interest in all things art, science, investing and tech with his long-held desire to establish positive sum scenarios designed to help promising creators and their inspiring ideas succeed, regardless of age, location, job history or level of education.”

Last fall when I was on his show, we played a game of mind-jazz about “how we can live curious, collaborative and fulfilling lives in our deeply weird, complex, probabilistic world.” For this discussion, I wanted to rotate the axis of our exploration and learn how Jim’s personal experiences have contributed to the frame through which he engages life. Sweeping across scales from candid autobiography to team inquiry into some of the wickedest problems — like how we foster meaningful relationships and balance achievement with humility — we covered a lot of new ground.

I hope you enjoy this conversation as much as I did and benefit from a fresh take on the mind — and heart — of one of the most exemplary mavericks I know.

If you find value in this conversation, please like and subscribe (YouTube | Apple Podcasts | Spotify), leave a comment, and consider supporting my mission to help us cultivate wisdom in an age of magical technologies. Humans On The Loop is fiscally-supported by my friends at HAPPI (Helping Awesome People Prosper Intentionally), so you can become a member here or make tax-deductible contributions at every.org/humansontheloop. Recurring donors get the same community perks, including the book club and online course recordings.

Project Links

Contact me if you have questions or propositionsProject pitch & planning document Full episode and essay archivesJoin the Future Fossils Discord Server for both public and members-only threadsMeet collaborators on the open online commons Wisdom x Technology Discord server

Chapters

0:00:00 - Teaser0:01:16 - Intro0:06:23 - Jim’s Backstory0:31:43 - Crisis Personalities + Creativity vs. Risk Mitigation0:46:28 - Networks of Trust + Bootstrapped Credentials0:53:37 - Incenting Trust: Mass Customization + Consensus Reality Collapse1:06:14 - The Iterated Prisoner’s Dilemma + Trust-Building in Social Networks1:13:25 - How Do We Design for Flourishing at Scale (or Can We)?1:21:22 - Markets as Complex Systems1:29:10- Using (Especially Local) AI to Accelerate Realizing Your Mistakes1:37:23 - Outro

Mentioned Reading, Listening, & People

From Nowhere: Artists, Writers, and The Precognitive Imagination by Eric WargoThe Master and His Emissary by Iain McGilchristFinite and Infinite Games by James P. CarseThe Status Game by Will StorrThe Tao Te Ching by Lao Tzu (John Minford, translator)Power and Influence: Beyond Formal Authority by John P. KotterOne Summer: America 1927 by Bill BrysonGödel, Escher, Bach by Douglas HofstadterThe End of Trust - McSweeney’s Issue 54

Bilawal Sidhu — How to Unite Reality with Imagination - Infinite Loops PodcastWill Storr — The Status Game - Infinite Loops PodcastBrendan McCord — AI and The Philosophy of Technology - Infinite Loops PodcastAdam Aronovich on A Cultural Anthropology for The Psychedelic Internet - Future Fossils PodcastReimagining the PhD - Nadia AsparouhovaThe TPOT PhD - Priya RoseSo many music festivals have been canceled this year. What’s going on? - Greg Rosalsky for NPR

Cory DoctorowDoug RushkoffAlfred North WhiteheadJosiah WarrenJed McKennaJosh WolfeSocrates

Upcoming Events

* My new single and music video “The Big Machine” goes live on April 1st! Pre-save to Spotify or pre-order on Bandcamp here.

* I’m co-facilitating a session on “Right Relations with AI” for the School of Wise Innovation’s Spring Cultivator alongside a superb faculty. Cohort starts April 3rd!

* The book club is back! Join us for a group reading and discussion of Federico Campagna’s Prophetic Culture: Recreation for Adolescents with asynchronous discussion in the Future Fossils Discord server and a live call on May 3rd.

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