Ryan Holiday: Timeless Lessons From History

My guest today is Ryan Holiday.

He’s a writer, media strategist, and the author of ten books. He dropped out of college at 19 years old to apprentice under Ryan Greene, author of Mastery and The 48 Laws of Power. He worked at American Apparel and founded an agency called Brass Check.

We begin this episode talking about two stories from Ryan’s book, Stillness is the Key. One is about Michael Jordan and the other is about Winston Churchill. Then we transition into new topics. We talk about the philosophy of stoicism, the benefits and drawbacks of anger, and what Ryan has learned from Peter Thiel.

Please enjoy my conversation with Ryan Holiday.

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1:32 Winston Churchill – the busiest man in the 20th century: saw the last British Calvary charge, writes 10 million words, holds office for 65 years, elected Prime Minister twice, painted 500 paintings etc. 7:06 Can a change of location effect your relationship to time?   12:37 Writing as zero-to-one and the importance of getting something down in order to gain momentum. 17:02 Michael Jordan’s Hall-of-Fame Speech where we learned how importance anger as fuel and making a career of hanging onto slights was to him. Could Michael Jordan have been Michael Jordan without these characteristics? 20:30 How widespread is anger as fuel to success? Is it the best method and how much correlation is there to someone’s success? 27:20 Anger as a “purity” in our current political landscape. 29:08 Taking a look at the history of change and how the News may not be the best way to stay informed. Is the current understanding of “being informed” is a vice rather than a virtue?   36:20 To be “informed” need to have basis of understanding before interacting with News sources in order to contextualize and not come at news with hubris. Problem of the twitter approach to news: a profession, reporting, that was once about thoughtfulness, nuance, and the long-form has been boiled down to 280 characters.   41:19 Stillness is the Key as part of a trilogy involving Ego is the Key and The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph. This trilogy was what Ryan had always intended to write but had to go through his other books to get where he is now. 46:35 Truly integrating stoicism into his everyday life.   53:18 Peter Thiel’s brain is in a perpetual Mexican standoff where two competing ideas are constantly in opposition. Thiel seems to have a great ability to frame subjects correctly. Eric Weinstein's idea that Thiel is the world's wealthiest applied philosopher. 58:00 Extending Thiel’s First Principles Movement by simply reading different things than what everyone else is reading, gathering different materials. 1:00:02 Is there a danger where reading history becomes the same thing as watching the news? Ryan’s interest in reading personalized experiences of history wherein you can learn through other people’s unique experiences, and more importantly, mistakes.   1:02:25 Ryan’s writing success is owed to him taking the words of smarter people them him, re-arraigning them and repackaging them into a unique system. Does writing always have to be original?    1:05:19 What is it about daily things that is so important to Ryan?   1:10:42 The idea of looking at data that shows what artists believe is their best work and what others believe to be their best work.   1:16:11 How do you know when something is interesting?    1:20:32 How is Ryan such a prolific writer?