Ryan Holiday: How Stoicism Transforms Leadership and Decision-Making in Business | Leadership | E347

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Who is Ryan Holiday and what is his career background?

Hala Taha 1:39
Yap gang, we are about to go super deep on the podcast today. We're getting philosophical with today's guest, and I can't wait. Ryan Holiday is joining us. He's a philosopher, an entrepreneur, a marketer, and an author who has transformed ancient Stoic principles into actionable insights that we can use as modern entrepreneurs today. He's the host of the very popular Daily Stoic podcast, and his latest book is called Right Thing Right Now. Now for today's conversation, I really want to spend some time on his come up story. He was an apprentice for Robert Greene. He was a marketing director for American Apparel at just 21 years old. He wrote a book about media manipulation. I want to talk about that.
Hala Taha 2:18
And we're going to get into stoicism and his new book about justice. We've never covered stoicism on the podcast, at least as deeply as we do in this conversation. So there's so much to unpack. Let's dive right in. Here's my conversation with Ryan Holiday. Ryan, welcome to Young and Profiting Podcast.
Ryan Holiday 2:36
Yeah, it's good to be here.
Hala Taha 2:37
I'm so excited for this conversation. And when I was researching for today's episode, I found out that you started your career when you were 19. You ended up dropping out of college at 19, which is the same thing that I did. I actually interned for Angie Martinez, who was like the biggest radio personality in the world at the time when I was in college for three years.
Ryan Holiday 2:58
From The Breakfast Club, right?
Hala Taha 2:59
at 105.1 now, but she was at Hot 97. And so apprenticeships are so important. You did it under Robert Greene. I had him on the show, one of my favorite episodes of all time. And so I want to start there. I want my listeners to get a really good understanding of your career journey because it's the first time on the show. So what did you learn? How did it impact your future career?
Ryan Holiday 3:19
Well, I'd say two things about it. So one, these things become clear after the fact. They start as a job. Somebody gives you a shot. Somebody gives you something to work on. It only becomes a mentorship or an apprenticeship afterwards. After a long time has passed, you can come to understand that's what it was. What really happened is I got a job as a research assistant for this writer that I really liked. And in a world before AI, I transcribed interviews he was doing for a book that he was writing. And so it was just this kind of mundane task that I did well enough that it led to another one and another one and another one. And all the while I was learning from him, I was able to ask questions, was able to work on other projects. And it sort of developed into this relationship that continues to this day. But through it, I learned the art of writing, the art of researching, how to manage a brand, how to put out a book. I learned all the things that I do in my actual job now.

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