#086 Jim O’Shaughnessy: Learning to Learn, AI Disruption, and the Future of Publishing

Listen to the full episode now: https://kite.link/smartfriends86t

Happy to announce that we have the one and only Jim O’Shaughnessy on the show! Jim is the legendary investor behind O’Shaughnessy Asset Management and now OSV. Jim is also the author of several bestsellers including What Works on Wall Street.

Jim and I have a fun, light conversation about the power of learning, curiosity, innovation, and technology-driven societal transformation. We also cover topics such as the publishing industry’s future, mental models, the role of AI, and the concept of Universal Basic Income.

Quotes from Jim:

1. "The smartest thing I ever did was stop being smart. Intellectual humility is super, super important."
2. "How to learn is not regurgitation. It is the opposite of regurgitation. It is challenging the things that are presented to you."
3. "Circumstances have changed. The environment changes around you. And it may be that you were correct up until 20 years ago, but a lot has changed."
4. "The future of publishing is going to be incredibly better for authors... AI gets rid of all the boring, laborious, repetitive stuff."
5. "Good taste is about to be a very profitable thing to have."
6. "When companies reach a certain number of employees or departments, bullshit starts taking over... 40% of senior executives’ time was spent in check-ins and meetings about meetings."
7. "There will exist a group of people who, through no fault of their own, will simply not be able to grok this new world."
8. "I fully understand most of the attempts at UBI are going to fail. That’s okay."
9. "There is just so much that can be done... AI will create a tsunami of slop, and people will increasingly pay for curation platforms that get them."
10. "I started taking arguments that I disagree with and asking the model to steelman it for me. It changed my mind on a couple of things."

Here’s what we explored in the episode:

• "The most important thing I learned was how to learn and unlearn... most people are never taught it. It is something that, almost by definition, you have to do yourself."
• It’s important for leaders to admit when they are uncertain, and lead a culture of open-mindedness.
• It’s important to adapt to new environments, not cling to outdated practices.
• There’s an upcoming shift toward AI-driven, author-friendly publishing models that reduce inefficiencies and empower writers.
• Jim predicts AI will allow a “tsunami of slop” content and open huge opportunities in curation.
• In a world of abundant content, good taste and effective curation will be very profitable.
• Jim shares his evolving views on Universal Basic Income (UBI), arguing for experimentation to address societal shifts caused by technological advancements.
• Understanding opposing viewpoints to refine one's perspectives helps make better decisions. Jim uses AI to force him to debate and understand his own opinions better.
• Jim credits his success to a lifelong commitment to curiosity, whether through broad reading or questioning established norms.
• "Curiosity is a shit starter. It ignited my curiosity to the point where I just voraciously read everything."

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Enjoy the episode, and share your thoughts and questions with me on X: @EricJorgenson