Lessons from a college dropout at 19, now best-selling author

This article is part of Tech in Asia’s partnership with The Jay Kim Show where we publish the revised transcripts from the show’s podcast interviews with top entrepreneurs. This is heavily revised from the original show transcripts. For the full interview, go here.

Ryan is an author and media strategist and the former director of marketing for American Apparel. He’s written five books now and has advised many prominent best-selling authors including Tucker Max, Neil Strauss, and Tony Robbins. Ryan’s story is particularly interesting because he dropped out of college at the age of 19 to apprentice under a famous author, Robert Greene.

Ryan’s written three best-selling books on stoicism. His latest is called Ego Is The Enemy.

I hope you enjoy this.

So, you dropped out of college. Why did you do that and how did you use that in your career?

“It was a terrifying thing, to be perfectly honest with you. It’s not as discouraged in Western culture as it is in other cultures, [but] that doesn’t mean that it’s encouraged. There’s really no map that says, ‘Hey, this is what dropping out looks like.’ Because most of the people that drop out, drop out because they’re not doing well in school. […] When Mark Zuckerberg left [college], it’s a different thing. He’s got a multi-million dollar business that’s chugging along.

“That’s not what it was for me. It was on a much smaller scale […] Instead of making millions of dollars, I was making US$30,000. I had to really do the math and think, ‘OK. The purpose of going to school is to secure some employment or advantage in this field that I’m pursuing. I’ve got that. I’m going to have to do it.’ It was terrifying and my parents were very upset. We didn’t talk for a long time. It challenges all the safety nets that we’ve built up as a middle-class society.

“I reject the idea that one’s parents can let them do anything. At 18, you’re an adult. You can make your own decisions and you have to be able to own the consequences. The consequences of my decision was that my parents were very upset. They tried to pull whatever strings they had with me, cutting various things off. They tried to use the most persuasive of all parental metrics, which is the withdrawal of affection or approval. It made a very difficult thing even harder.

“Over time, I think they began to realize their mistake. I began to realize that I’m not sure I wouldn’t have done the same thing. The role of a parent, ultimately, is to keep you safe, […] not encourage you to take risks that may or may not help you thrive as a person.”

How did you then run into the next stage of your career?

“It all happened at about the same time. I didn’t just leave [college] to go to the [talent] agency. I had also met [and worked for] Robert Greene, and he was a research assistant. […] I had these two jobs; I was cobbling together a decent living at that age; I was doing exactly what I wanted to do. I felt very lucky in that regard.

“Robert is on the board of directors for American Apparel. After some time passed working for him, he made a referral there, and this process happened again. That’s what I don’t think people realize. […] They think getting a degree is what’s going to get them ahead. That might be true in certain fields that very, very much require those degrees. Knowing a person and doing good work for that person who has the ability to make calls or decisions is ultimately going to be far better than any piece of paper.”

In Ego Is The Enemy, you talk about ego and pride. How can you define the difference between the two?

“[I define] ego as a collection of negative traits. I think pride—maybe undue pride—is probably one of those traits. Ego is not one thing. It manifests itself a little bit differently in different cultures. What I think is interesting is how often our smug pride and our egolessness is itself a form of ego and pride. […] If we think that we’re better than other people because we’re not showboating (and maybe those people actually aren’t showboating), [then] you put yourself in a position where […] you’re just judging everyone else.”

In the book, you talk about alive time and dead time 

“Yes. I mean, look, I got some very frustrating, bad news. I won’t get into it, but it crushed me in an unexpected way. I didn’t think I would care about it. […] I just got home from traveling [and thought], ‘Oh, I’m just going to lay around all day.’ That’s dead time embodied. It’s like, ‘Oh, you hurt me by doing this thing and now I’m going to respond by wasting one of the days of my life when I don’t know how many days I have on this earth.’ That’s a terrible decision. You have to catch yourself.

“What I sometimes do in situations [like these] is just throw myself into work, which is just a way of denying your feelings. I don’t think that’s productive either. I just [had to say], ‘Look, I’m going to take it easy because I’m not feeling great. I’m going to read. I’m not going to watch TV all day. I’m not going to sleep all day. I’m going to actually try to do something […]’ If I had complete freedom over my day, like if I didn’t have any responsibilities, I would probably spend a good chunk of it reading. I’m going to treat myself in that regard. That’s the alive time, dead time concept, which again is from Robert Greene; [it’s] not mine. It’s taking a situation that could be wasteful and turning it into something productive.”

You talk about stoicism a lot. If you could, in one or two sentences, describe what stoicism is, how would you put it?

What’s your one piece of advice for young entrepreneurs, whether they’re coming out of college or doing the side hustle?