Ryan Holiday talks about his early career working with authors like Tucker Max and how he landed mentors. He shares what actually works when you're trying to get someone established to take you seriously.
I think the most interesting thing that I want to dive into today is some of the career decisions you've made.
Sure.
So let's first start off. Tell us a little bit about yourself in terms of your early work. When you were 19 years old, you worked with best selling authors. You worked with people like Robert Greene and Tucker Max. Okay, how did that happen?
I mean, it was a very weird time just for me personally and sort of the industry. It was a time when people were getting book deals from the Internet. And I was a big fan of one of those authors, which was Tucker Max. And I was in college at the time and I was writing, I had a column in college newspaper which basically anyone could do. But I thought, I'm gonna use this column. I'm just gonna reach out to anyone that I like. And so I reviewed his website.
Okay, got it. So first of all, everyone loves to be reviewed or interviewed, especially in the early stages of their career.
Yeah, he wasn't getting written about all the time. And most of the people who wrote about him were about him in a very dismissive way. And he and I are very different people. His stories are about drinking and hooking up. And at that time, that's not like I've had the same girlfriend for seven years now. I don't drink. So we're very different people. But I saw something in his work that I really liked and I think he appreciated that I wrote about it in a deep appreciative, but not a fawning kind of way. And that he, not the New York Times had written about him, but they didn't write about him that way. And that's where that connection came from.
Got it. So you go to him, you write a review about his website and he sees something in you and he starts engaging with you on like a free internship level.
Yeah.
So what are you doing at this point?
I would, and at first I would just look for like any excuse to email him that wasn't like bothersome. So I'd be like, hey, like I read this article, like maybe you would like it. What do you think? Just sort of creating a rapport. I think a lot of people think that sort of like internships or mentorships are these very official things. I get emails from people now. They're like, I would like you to mentor me.
Yes, I'd like you to be my mentor. And what are you supposed to do with that email?
Right. It doesn't make any sense and it sounds very intimidating and difficult. It's like, I don't wanna sign up for that. It seems like a lot of responsibility, so. No. But this was a very unofficial, gradual thing that sort of evolved over time, which is how I think they work best. And so I would ask questions, I would find things that I thought he wanted. And then I think one day, he lived in New York at the time, and I was going to be in New York for some reason, and I said, like, hey, I'm gonna be here. Will you sign. We've been talking for a year. Will you sign my. A copy of the book. Of your book, and I wanna ask you some questions. And then we sat down. I think we got coffee or lunch or something. And I was like. Like, I noticed this thing on your website. I think he, like, he had a bunch of unsold advertising inventory, if I remember correctly. And I had some idea for what he could do with it. And I was like, will you. I'm not asking you to pay me. I'm not asking for, like, a handout or I'm not asking you to take me under your wing. Just let me try this, and if it works, like, awesome, and if not. And I don't think it ended up working out. But the point was I took some initiative. I had a real tangible suggestion that that was basically all upside for him. And I worked hard and I was reliable. And the next time he had something that he actually needed someone to do, I was the person that he asked.
