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.
This magisterial history, written by Edward Gibbon, covers the peak of the Roman Empire, the history of early Christianity, the fall of the Western Roman Empire, and the rise and fall of various other empires and civilizations up to the fall of Byzantium in 1453. Gibbon's work is renowned for its thorough scholarship, diverse sources, and engaging prose. He argues that the Roman Empire succumbed to barbarian invasions partly due to the gradual loss of civic virtue among its citizens and critiques the role of Christianity in the empire's decline. The work was published in six volumes between 1776 and 1789 and has remained a seminal work in historical literature despite some criticisms from modern scholars[2][4][5].
Topics:
(00:00:00) - Intro
(00:03:30) - What’s the most important thing you’ve ever learned?
(00:07:23) - Learning to Learn
(00:11:20) - How learning changes as you age
(00:18:51) - How do you think about your circle of competence?
(00:22:21) - The future of book publishing and how authors adapt
(00:35:29) - AI disruption in book publishing
(00:47:56) - Jim’s inaugural book: Two Thoughts
(00:56:46) - LLMs for authors, and UBI
Links:
Jim on X
Infinite Loops Podcast
Infinite Books
O’Shaughnessy Ventures
Margins: Book Tracker
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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- It’s important to adapt to new environments, not cling to outdated practices.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."
Important Quotes from the podcast on Business and Entrepreneurship
There is no skill called “business.” Avoid business magazines and business classes. - Naval Ravikant
You have to work up to the point where you can own equity in a business. You could own equity as a small shareholder where you bought stock. You could also own it as an owner where you started the company. Ownership is really important.
Everybody who really makes money at some point owns a piece of a product, a business, or some IP. That can be through stock options if you work at a tech company. That’s a fine way to start.
Smart Friends 
