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Timeless Wisdom from the Stoics
A podcast conversation with #1 New York Times best-selling author Ryan Holiday
Ryan Holiday sits at the helm of a modern-day philosophy empire.
The titles of his books alone provide microdoses of wisdom: The Obstacle is the Way, Ego is the Enemy, Discipline is Destiny - and the list goes on.
His Daily Stoic podcast and social media channels serve up bite-sized stoic insights to hundreds of thousands of people daily.
But you’d never expect him to end up here from where he started.
He was the first marketing director for American Apparel, a brand known for its salacious and controversial style of marketing.
Fresh off several eyebrow-raising campaigns, he wrote the book on the dark arts of digital marketing - Trust Me, I’m Lying – a fun romp of a read which amounts to a playbook of manipulative techniques that has been used by many a savvy politician and marketer since.
Not that this was ever his intention. In our interview, he recounts:
“It's heavy shit (…). I wanted to expose how media manipulation work, hopefully, to make it less effective, right? And then to watch, not just political operatives inside the United States, but you could also argue a lot of the disinformation and misinformation tactics of sort of foreign actors, whether you're talking about Russia or China, relies on some of the same stuff that I was talking about in the book. And so for that book to continue to be relevant is not exactly my definition of success. I would like to, it to have been proven wrong or to have done its job, which is that, you know, people put up some relatively obvious defences against these sorts of loopholes.”
Was a moral awakening at the root of the transformation that would follow?
A path emerged via an apprenticeship with Robert Greene (the man he affectionately hails as the “GOAT” of nonfiction writing), and he decided to dedicate his life to reviving the ancient and powerful philosophy of Stoicism.
Since then, he’s rattled off no less than twelve best-selling books - and he’s not even close to 40 yet. Have I mentioned he also co-produced a Grammy-award winning Jazz album along the way?
In this interview, Ryan adeptly displays his mastery at interweaving the core insights of Stoicism into the key challenges of modern life.
I hope you enjoy learning from Ryan as much as I did in this one. You can check out the full interview on YouTube here. In the meantime, you can start with Ryan’s advice on avoiding what he calls “the boring tax” in the clip below.
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