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Crazy Wisdom

Jul 7, 2021

James O'Shaughnessy is the founder, chairman, and co-chief investment officer at OSAM (O'Shaughnessy Asset Management). In this episode, we discuss the changes that have come about in the world post-COVID, mainstream media, politics, navigating the future as a society, the law of attraction, and much more. 

You can catch Jim’s podcast, Infinite Loops, at



1:58 - How covid accelerated the evolution of work meetings

6:47 - What is quantitative analysis? And how is it different from hedging bets?

13:36 - The world, especially after covid, has changed with respect to investing and decision-making, what do these changes look like? What will they result in?

19:08 - The crazy thing about Silicon Valley

21:24 - A rule of thumb for filtering who to have political discussions with

22:07 - How mainstream media in America is committing suicide

31:12 - How to deal with self-deception and how it is easier for intelligent people to fall prey to self-deception.

36:47 - How do you navigate the differences between eastern and western philosophy?

48:04 - The dangers of premature certainty

48:43 - The truth behind the law of attraction

54:01 - What is negative compounding and why should you be wary of it?

1:00:50 - Why free societies do better than unfree societies.

1:12:31 - Why you should see life as a “choose-your-own-adventure” game

1:20:44 - Why the atomization of society, the destruction of geographical boundaries by the internet, and addiction to social media outrage all work to serve a healthy purpose.

1:31:20 - Why marketing is the bedrock of all of humanity’s greatest institutions.