Shea Serrano

Hey, You’re Cool! Author Shea Serrano

Becoming a bestselling author wasn’t always the dream for Shea Serrano. In fact, there was a time when he didn’t even know it was a possibility. “That’s not what they tell Mexican kids in San Antonio,” he explains, “that you can fuckin’ make jokes on the internet or write about Lil Wayne and get paid for it.” But as an underpaid teacher with a family of five, that’s exactly what he started doing to make money on the side.

What began as a part-time hustle has turned into so much more. No longer in the classroom, Shea has two well-received books to his name: Bun B’s Rap Coloring and Activity Book, and the New York Times bestseller The Rap Year Book: The Most Important Rap Song From Every Year Since 1979, Discussed, Debated, and Deconstructed. AMC is converting the latter into a six-episode docuseries executive produced by The Roots and set to air next year. Now, Shea’s got another book on the way with Basketball (and Other Things): A Collection of Questions Asked, Answered, Illustrated, which is due Oct. 10.

Before his latest book hits the shelves, Serrano breaks his career down with MASS APPEAL, chopping it up about finding his voice and learning valuable lessons along the way. He also explains how he galvanized a huge fan base with the FOH Army, how he’s using all of that power for good, and what inspired his next sure-shot paperback hit. Meet the cool teacher-turned-world renowned writer, Shea Serrano.

You were a teacher and a hip hop journalist at first, which is similar to my path. What drove you to pursue such different career paths?

Well, originally, I wanted to be only a teacher. My dream was to work at a school for like 30 years or whatever, and teach three different generations in the area. That was the goal and the writing stuff just sort of happened because it needed to. I was trying to make some extra money, because you can’t really raise a family of four or five on a teacher’s salary. That’s how writing started. Writing was never like a passion of mine. I didn’t grow up wanting to do it or even knowing that was a job you could do. That’s not what they tell Mexican kids in San Antonio, that you can fuckin’ make jokes on the internet or write about Lil Wayne, and get paid for it. So, I was just doing it on the side. Over the course of a few years, it just kept getting bigger and bigger, until eventually, it got to the point where it was like, “Oh shit! We’re making more money freelancing than I am working full-time as a teacher, so let’s see what happens if I take some time off of teaching and only do writing.”

What did you notice at that point, when you took that leap?

Well, one, I noticed that I was way less tired because I was teaching full-time and then I was also coaching basketball, football, and track, and then also writing a book, and then also freelancing. By the time I just started writing full-time, it was like we got rid of three of those things. There was no more book because that was done. There was no more teaching, there was no more coaching. Now, it was just straight-up writing. You just have more time to dedicate to a thing, so of course, you’re going to get a little bit better at it and that’s probably the main thing that happened there. Once I started focusing my time and energy on it, cool stuff started to happen.

Bun B’s Rap Coloring Book was cool because it allowed you to show off another side of your creativity. What did you learn from that experience with Bun, that allowed you to transition into the next phase of your career?

There were definitely a couple of things I learned there. If we’re talking about just smaller stuff, I learned how to use Adobe Illustrator. I know how to draw, like if you give me a pen and a paper, that’s fine, but I had never done it on a computer before. So I had to learn how to do that. Once I knew how to use Adobe Illustrator for that, I was able to enrich other assignments. Whenever I was pitching a thing, it made me feel like I was more marketable. I could say, “Here’s the idea for the article. Here’s the idea for a supplemental piece of art or a chart that will go with it.” There was a market for that, which I had no idea. I did some art stuff for MTV, ESPN, XXL. People were coming to me just for that all of a sudden, so that was cool. So, if we’re talking about specific skill things, that was something I learned there. But the main thing, the bigger thing I learned was, when I started doing all that stuff, I didn’t have any idea how the book world worked. I didn’t know how to get a deal. I just had to sort of figure it out. It was the same thing with writing. I didn’t have any experience, I didn’t know anybody who had done it, I just knew I was going to figure it out because, if somebody else figures it out, then I can probably figure it out too. So, when I did it again with the book stuff, that was a moment for me where I was like, “Oh shit! Maybe I’m good at figuring stuff out. Maybe I’m not the best writer in the country, maybe I’m not the smartest person in the country, but I’m pretty good at just solving a problem and making a thing happen.” So, to just go from nothing to a book deal, that was a big thing for me, a big confidence boost. Then, I just sort of carried that forward. It didn’t matter what someone was asking me to do or try, I was like, “Sure, I can do it.” And then I would just figure that shit out.

You figured it out and then you released The Rap Year Book. Not only did you release it, but you galvanized an audience in a unique way. Fans still buy multiple copies and you even have a group of supporters in the “FOH Army.” Why do you think people responded to that book and the campaign the way they did?

I would guess that a part of it is just because I had not done it before and people weren’t really doing it that way yet. But mostly it was because I had been on Twitter for a while and if you’re there enough, you sort of build up equity, right? So, I think when The Rap Year Book was coming out, I had maybe 40,000 followers or something and they had been following me for a good little bit. So, I was like, “I have this book coming out. Buy it if you wanna buy it.” It was those same people who were the ones who went and bought it because they had known me, at least from the internet, for a good little while now, like two or three years or something like that. So, it’s the same as like, if you’ve got a book coming out and my neighbor has a book coming out, who I never talk to, I would buy yours because I know you and I feel like I would be at least a little invested in your success because you’re my buddy and I want to see you do well. I think it was the same way with The Rap Year Book. People were like, “We can get behind this and if we do, then this guy is gonna have a successful little thing going on.” And there you go. That’s probably it. There was just some equity there. Then, going forward after that, it was like, “Oh cool, I have this resource. Let me make sure I’m using it to do good and not just in a very selfish way.” So, I was never really just trying to make money off of it, I was never trying to do anything other than shine a light on other people who were doing some cool shit. Then, I guess people just recognized that or appreciated that and it’s very organic and very pure. So, if I ask for a thing, it usually happens.

I think one of the reasons that you connect with people so well is that you have a distinct voice. How were you able to find your voice?

I think that’s just a matter of getting your reps in, really. If you do a thing enough times, you settle into what the best version of it is. A couple of years ago, I tried to learn how to ride a skateboard. I didn’t know how to do it and the beginning parts were really, really bad, but after a few weeks, I was like, “Okay, I can stay on it.” After a couple of more weeks, it was like, “Oh shit. I can go up and down a ramp now.” It’s the same way with writing. You just keep doing it and keep doing it and, if you’re paying attention at least, you will see what works and also what doesn’t work. You’ll also be able to tell yourself, “What did I feel good about when I finished writing it? What did I feel bad about?” You’re just taking all of these little bits of information and you’re seeing stuff that other people are doing. Like, I might read something that you write. Whenever I would read your stuff, it was always like, every time I read your articles, by the time I got to the end of it, I had all of the information I needed. If there was nothing else in there, I knew that if I clicked on a news story that Andres wrote, by the end I wouldn’t need to read any other versions of that news story. You know what I’m saying? So now, I’m telling myself, “When I’m writing a thing, I want to try to do this. I want to try to do a version of what Andres is doing. I want to have all of the information here, so that they don’t need to go anywhere else to get it.” It was just picking up little pieces like that, that other people are doing, and just trying to make it feel as natural as possible.

Thank you. Another thing that’s interesting about your work is that you’ve taken your voice into different realms. You started within hip hop, but transitioned into movies and television with recaps and analysis, and then now, obviously, it’s sports. So, let’s talk about your forthcoming book, Basketball and Other Things. Following The Rap Year Book’s success, what motivated you to take your writing into another world entirely?

After The Rap Year Book took off, it was like, “Okay, cool. I will have the chance to do another book.” I didn’t want to do another rap book because I had just spent two years or whatever researching all of rap and learning about it. I was like, “Let me take a break from that.” Basketball was the other thing that I liked the most. Whenever you’re working on a book, it’s very labor-intensive. It’s very research-intensive and you’re going to spend a lot of time within a subject. It’s just way more helpful and enjoyable if you’re at least doing a thing that you’re interested in, or care about. All of the stuff you know in your head about a specific subject right now, it’s not near enough what you need to know in order to write a book. There’s a lot of time spent reading articles, reading books, watching interviews, watching games, it’s just a fuckin’ lot of work. So, I wanted to do a thing that I was at least gonna be interested in so I was like, “I would much rather watch Shawn Kemp dunk videos as part of research than whatever so I’ll just do a basketball book.” And there you go, that’s why we settled on basketball. Also, money was important. I know if you write a book, they give you a check, so I was interested in that, as well.

Did you have to remodel your kitchen again?

Yeah, basically.

shea serrano

What did you take away from Basketball and Other Things that you didn’t know before?

Well, you learn fuckin’ everything, really. Like, the NBA has different periods. For example, the birth of the modern NBA was like 1979-1980, which is when [Earvin “Magic” Johnson Jr.] and Larry Bird were drafted. You start building up your stars through that era, which is really the golden era, and then you get to Michael Jordan. When you get to Michael Jordan, you’re like, “Okay, now we have one central figure who will sort of dominate everything.” That became the theme of the NBA for a few years. Then, you get to Shaq era. When you’re reading through all this stuff and researching all this stuff, you can sort of pick up these six themes that were happening and the way the game was changing. Like, now we’re moving up the 3-point line, or we’re getting rid of hand-checking rules, which will affect basketball in this way or whatever. You just take all of that stuff and then you’re like, “Oh, now it makes more sense to me why the 2004 [Detroit] Pistons were able to beat the 2004 super [Los Angeles] Lakers.” All of the stuff you see the front of, it now makes sense because you know what the backend looks like.

Now that you’ve had so much success, where do you take this next? Film? TV? What is next for you?

It’s always weird for me to be like, “I’m a successful writer” or whatever, because in my head, I will just always associate successful with being rich and like, I wanna be rich, so I don’t know. I think I just need to figure out, how do I get to the money? That’s my main thing. I want to buy a brand new house or whatever, so when I’m trying to figure out what comes next, I don’t know. We’ll probably do another book, I’m sure, eventually. I’ll take some time off and then we’ll do another book after that, but in the meantime, I work at The Ringer and that’s a job I like a whole, whole bunch. Now that I don’t have a book or anything else in the way, I’m able to do more stuff there, so I’m sure I will sort of lean in to that. If I were to pick an area where I want to do more, it would definitely be that. I want to like, make my name at that spot, because I feel like there are people who are better than me there so I want to try and beat them.

I know you’re probably going to get a variation of this question every year for the rest of your life, but what is 2017’s most important rap song thus far?

That’s tricky because my gut is telling me [Cardi B’s “Bodak Yellow (Money Moves),”] just because it’s been in the news and everywhere and it’s the first time in almost two decades a woman has a No. 1 song or whatever, but I don’t know if that’s the right answer yet. I would say that one, but I’m not all-the-way certain yet. Again, I haven’t sat down and really combed through everything. I’m sure there’s an argument to be made in there for maybe a Chance the Rapper song or something that’s a level or two below that, that will leak out and influence all of the stuff above it eventually, like what we saw with Fetty Wap and Young Thug and all those guys. So, I’m not 100 percent certain, but maybe “Bodak.” That’s probably the safest pick at the moment just because it’s everywhere.

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