Exploring AI-Enhanced Self-Reflection and the Value of Experimentation

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 documentFull 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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