Q&A with The Ringer’s Shea Serrano

A successful author just scratches the surface of what Shea Serrano brings to the table, dive deeper and you’ll find a passion for writing, something even he didn’t think would take him to where he is now. Amassing an unbelievable following, including the success of not only his daily work, Serrano has two successful books and a third on the way in October.

Ulrey: How did you get to where you are right now?

Serrano: When I first started freelancing, I was teaching at the time, and this was maybe eight, nine, years ago. I needed another job. My wife couldn’t work anymore because she had some complications with a pregnancy, so she was on bedrest, and we needed to make up that money that we lost when we’re not working. Nobody would hire me because I already had a full-time job. So I thought I could try to do something from home.

I decided I was gonna be a writer. I just started calling up newspapers that were in Houston, and emailing everybody telling them I was the new writer in town and I was trying to find work. That’s how I got on, started at this tiny literal neighborhood newspaper this woman was printing up in her garage. She’d pay me like $15 to write an article about the Houston Astros or something like that. I took those and turned it into what was at the time the Houston Press, which was the big all-weekly paper in Houston. Working there’s really where I figured out, oh you can make a living from this. I just started writing as much as I could, grabbing all the assignments I could.

This was over the course of four years. I started reaching to other papers and places, trying to find all the work that I could. You do that long enough and your name starts to ring out. I was writing the weekly column at LA weekly, and a woman named Molly Lambert, a staff writer at Grantland, saw it and passed it and they hit me up and asked if I wanted to freelance for them.

They offered me a position so I went to work there, and then Grantland got shut down. The next year, Bill Simmons started The Ringer so that’s where I am now. Boom.

Ulrey: What was it like making that transition from doing freelance to joining Grantland and The Ringer?

Serrano: It was really tricky when I first started. When I got the first contract at Grantland, I was teaching still, this was all while I was teaching. I didn’t want to leave teaching, so we worked out a part-time agreement where I could stay teaching but all my writing would go to them. That was really when I figured out that I liked to write and that I wanted to give it a shot, writing full time. They wanted me to try full time, so I transitioned in July of 2015. That was tricky because I was going from being a teacher, which is like all of your whole day is planned out, to now I’m a writer living in a city where the place where I work doesn’t have an office so it’s sort of me by myself.

So it was hard at the beginning. I felt insecure about my place in the writing world, didn’t know too much. It was hard. It took several months before I started to get comfortable, and when I did get comfortable is when they shut Grantland down so I had some time after that to work on the book. It was not an easy transition but I had all the support I needed behind me.


Ulrey: How did “The Rap Year Book” come about?

Serrano: The Rap Year Book wasn’t an idea that I had. It was an idea that my editor, the woman who approached me about doing the coloring book (Bun B’s Coloring Book) together. The coloring book came out and it sold a decent amount of copies, and she wanted to do another rap book.

She had the idea about the most important song of every year. When she approached me the first time, I didn’t want to do it. I thought it was a super boring idea and I was picturing a simple textbook type thing. A couple months after that, when my wife and I decided to move into a house, I went back to her.

She let me build it out with all the illustrations, made it more fun to work on. I finished the book in April of 15, before Grantland shut down. It helped me with the Basketball book because we were working on that idea at that point.

It was neat watching all the stuff happen with it. It got on the best-seller list for a few months. It was a lot of fun after the fact, working on a book is terrible. Four or five rounds of editing. When you’re done and have the book you feel good, especially when you sell a bunch of copies.


Ulrey: You’re finishing up your new book (Basketball and Other Things) that comes out in October. What’s it been like having all these followers of yours blind pre-order it?

Serrano: That makes me feel good because of course if they’re ordering it now, it’s not because they saw a part of it they liked. The only reason that anybody would order that book right now is to be like “we’re rooting for you”. There was no cover, no description, only a link. It’s been cool to watch that happen, people do that and it makes you feel good, it makes me feel good. There’s no information out there but we’ve already pre-sold a few thousand copies, so it’s cool man, there’s really no other way to say it.

Ulrey: What advice would you give someone trying to freelance and how should they go about getting their name out there?

Serrano: Let’s say you’ve already got some assignments and you’re going in that direction. You can’t be that person who turns stuff in late, misses deadlines, doesn’t respond to emails. That’s a killer man. I think a lot of editors would rather work with a writer who was a pretty good writer who never missed a deadline than work with an exceptional writer who you can’t depend on them. It’s just disrespectful, no one deserves that.

Really work hard at coming up with new ideas, writing about things in new ways, if you want your name to ring out. You can’t just do what others do, because you’re not gonna win that battle. For example, if I’m writing about a basketball game and Zach Lowe is writing about a basketball game, why would anybody choose mine over his if we write the exact same thing, knowing that he knows way more about basketball than I do. I’ve gotta figure out another way to write about this game, that’s gonna force readers to read what I wrote. I think a lot of young writers see the same twenty ideas and if you end up doing those things you’re not gonna get ahead. Just come up with new shit.

Ulrey: Do you think your social media presence is something you wanted to have, or how has that come about?

Serrano: That was not a thing that I planned on happening, it just sort of happened. I didn’t realize how powerful it was until The Rap Year Book came out, we sold basically all the copies through Twitter, built up all the buzz through there anyway. When the coloring book came out, my main plan was to just get as much press coverage as we can. I wanted to get the coloring book in Rolling Stone, the Los Angeles Times or whatever. I thought if I did that it would drive that up and I was able to get it in all those places, but it didn’t sell as many copies as I wanted to.

With The Rap Year Book, we did the opposite. At that point maybe I had 40,000 people following me. If I can even get 5 percent of the people following me to buy a book, that’s 2,000 people, that’s a really good first week. We sold way more copies than that just going through twitter. It wasn’t until then I realized how powerful it was. It’s a good thing to have, especially if you’re trying to get a job somewhere, having that support system built in. It’s not absolutely vital but it’s a thing people look at now, so it’s helpful if you’re a new writer or new anything really. It’s never a bad idea to have 100,000 people that you can update immediately.