Shea Serrano Quit His Teaching Job, Now He Has Two Best Sellers and Two TV Shows
"It is funny to just walk in and just be a Mexican, because I’m usually the only one there"
As the 1 p.m. time slot for my phone conversation with Shea Serrano drew near, I began to realize that for all my supposed knowledge about the former teacher and current author who’s put out two New York Times bestsellers since 2015, I had absolutely no idea what to expect. It was comforting to discover that despite Serrano’s sharp and seemingly calculated ascent through the long-form content world over the last few years, neither does he.
The one thing I did expect was brutal honesty. And that’s what I got for most of an hour, as he recounted what it was like to leave a steady teaching job for a gig that evaporated three months later, as he discussed the nuances of career changes when you have a wife and kids, as he described meeting with publishers who wanted him to replicate the type of success that he wasn’t sure could ever happen again.
In 2017, Serrano not only released his book Basketball (and Other Things), he also took steps into new mediums with the possibility for an even bigger audience. It was announced that The Roots will executive produce a documentary series on AMC based on his collection, The Rap Yearbook, and that he’s teaming with veteran sitcom creator Mike Schur (The Good Place, Parks and Recreation) to make a show for ABC about Serrano’s life growing up with five uncles. He also inspired his dedicated Twitter fanbase, the Fuck Outta Here Army (FOH), to raise an incredible amount of money after Hurricane Harvey devastated his hometown of Houston.
There are two types of influencers, the type that sets out specifically to create influence, and the the type for whom influence is a byproduct of passion. The latter is the type we end up talking about for years to come. And that’s the kind of influencer that Shea Serrano is, whether he intends to be or not.
Have you had the time to sit back and really reflect on what the last couple of years have been like for you?
I think about it every day. How can you not? A thing that ends up happening is people will think that because I’ve been freelancing for so long that I’ve been writing for that long. But I didn’t start writing full-time until two years ago. Before then teaching was my main job, so that was where all my main energy went. I think about it a bunch. Especially, like right now. I just picked the kids up from school. I think about like, “Oh crap, I should be in a classroom right now” or whatever.
Do you ever get anxiety about that? It’s been a while and you’ve had a lot of success, but do you ever lay awake at night and wonder, “Am I sure?”
Yeah, I feel like that a bunch, but mostly when I’m doing money stuff. Since I’m a dad and husband, and my main job at home is that I’m supposed to pay for all of that stuff. The first time it really, really hit me was when I signed a full-time contract in July of 2015. In spring of 2015 I was still teaching full-time and it was not 100 percent sure if I was going into writing full-time. I talked to my wife a little bit, and it was like, “If all the numbers work out, we’ll go for it.”
I left the classroom June 1, 2015. In July of 2015, I signed a contract to go full-time, and it was like, ‘”There’s no more teaching money, I only make money writing now.” October 2015—three months later—I got fired. Everybody, where we worked, got fired at the same time when Grantland shut down.
Luckily I’m at the point now where I’ve been a little successful, we’ve had the two books come out that were bestsellers, I have a little name recognition in the book space. I’ve been at The Ringer for 70 weeks or something like that.
Is the GIF out yet? I haven’t seen it
No, I forgot to do it today.
But, yeah, there’s a level of permanence there. And that’s sort of the thing that you plot for when you’re a parent: “Okay, if everything fell apart today, how long could we survive on nothing else coming in?” And the further out you can build that window, the less nervous you get.
Is there anything about teaching that you miss at all? You strike me as someone who’s really engaged with the human element of things, and the classroom seems like a place that tailors to who you are as a person. Correct me if I’m wrong.
No, that’s exactly right. Interacting with kids is the best part of teaching. It’s the hardest part, as well, but the best part. I miss it a bunch, especially because being a writer is a lonely job. It’s a thing where the results only affect you to a certain extent. So, yeah, it’s the total opposite of teaching. And, teaching every day, I was in a classroom with 25 kids all looking at me, expecting something from me. With writing I sit at a desk and just stare at a computer. I miss it a bunch.
Do you see yourself getting back into it?
Yeah, I’ll eventually go back for sure.
The Rap Yearbook, in my opinion, changed the content landscape, especially for younger generations in hip hop. During a time when short-form content appeared to be king, here’s this thing that’s both long and not on the computer, two things that were supposed to be deterrents. Was that a concerted effort or just the logical byproduct of brainstorming?
It was probably a little more of the latter. I wasn’t sitting around going, “I need to design a book for kids who are on the internet all day long.” I just wanted to make a cool thing, and probably because I’ve been on the internet so much, it just ended up how it ended up. It’s a thing that’s all held together by one main premise for sure, and secretly it’s like a history of rap textbook, but the way that it’s built, it’s easy to consume a small piece of it. Each chapter is only like six pages, I think. They have art in there that’s fun to look at, but it wasn’t a master plan that I had. It was more just the result of maybe me being on the internet too much.
How different was the experience of going into The Rap Yearbook without a ton of notoriety to the experience of there being anticipation for
Basketball and Other Things, which had to feel like somewhat of a failsafe.
There are two things I should probably mention. The first one: It felt the opposite of having a failsafe. The Rap Yearbook had done so much by that point. It had been on the bestseller list, it had been picked by Billboard as one of the 100 best music books of all time, it had been picked up to be a documentary produced by The Roots, translated into five different languages. It felt, to me, like when you do a cool thing and everybody immediately goes, “Oh, what’s the next cool thing that you’re going to do that’s exactly this big or bigger.” That’s the conversation you have with the publisher. They’re like, “Well, we want another one of this, but bigger.” And it’s like, “Well, fucking shit, I don’t know how the first one got like that.” So I was very nervous. It’s hard to sell books. It’s hard to sell books about basketball. So yeah, more than anything, I was nervous that it would just totally flop and everyone’s gonna go like, “Oh, maybe he doesn’t know what he’s talking about. Maybe he doesn’t understand how the internet works,” or whatever.
As far as building it, the only thing that was different was the knowledge I had going into it of how much work it was going to be. The research was the same amount of research per chapter. It was the same amount of creative energy needed to come up with everything. All of those parts were exactly the same. The only difference was, this time going into it was I knew how fucking hard it was going to be. When you’re pitching a book, you put together the proposal, and the proposal has like one or two sample chapters in there. So when I was writing the proposal for the Rap Yearbook, I just picked two songs that I already knew almost everything I needed to know to write the chapter: “Dear Mama” and “Nothing But a G Thang.” Those were two songs I’d already done significant research for with other projects. When I wrote those two chapters, it didn’t take me but a day to write each one or something like that. So I thought that’s how long it would take me to write every chapter. They give you a year to write the book, I didn’t even start working on it until like, month eight or month nine. I didn’t do anything. And then I sat down to write the next chapter, which was on I think DMX’s “Ruff Ryders Anthem.” I sat down to write that one, and that one took me like a week. I started writing it and I was like, “I kinda don’t know a lot about DMX”’ I read this book and I was like, “I feel like I don’t really have a sense.” I need to read everything about DMX that came out from 1998 to 2000, watched a documentary. By the time I was done, a week passed, and I was like, “Fuck, there’s no way I’m finishing 33 more of these chapters in the next two months.” So I was six months late turning the book in.
With the basketball book, I knew ahead of time how much work was going to be needed for each chapter. It’s like a veteran thing. You know how hard the playoffs are only because you’ve been through the playoffs.
You mentioned that potential backlash being, ‘He might not know how the internet works.’ Does anybody really know?
Yeah, a bunch of people do. Every person that’s famous on the internet knows how the internet works. They know exactly how it works. Kim Kardashian understands the internet more than anybody in the history of internet. That’s why she’s worth whatever she’s worth. Kids understand it intuitively now. Like when Vine came out and all of a sudden we had these kids who you saw them on Vine one day, and two weeks later they were on MTV or in movies. They just understood how it works. People definitely understand how the internet works. Probably I don’t, probably you don’t. We’re maybe too old. But my kids do. The 10-year-olds do.
I think I was following you for a year-and-a-half before I discovered what you look like. So, when you take these meetings and you go and meet these publishers, have you encountered a situation where someone was visibly struck by the fact that you’re a Mexican man?
You know what, that happened very early in my writing career, when I was at the Houston Press, before anyone knew anything about me. I would take these meetings with rappers and I’d walk in and they’d be like, “Oh shit, I thought you were a woman.” But now, not that much. It is funny to just walk in and just be a Mexican, because I’m usually the only one there, but that’s a different thing.
What’s the one thing you aim to do every time you sit down to write something about basketball? I think one of my favorite tweets of yours is when you called Kyrie Irving a demon-slaying dragon. And it’s like, “Wow, that’s accurate,” but how do you get that out of a guy wearing a tank top?
I just want to come up with some sort of way to write a thing about a person that has not been written yet. The most interesting parts of basketball for me are usually the feelings that it can elicit. It’s interesting to write about those things, because I know that everybody that’s watching basketball is feeling those same things, because that’s why you watch basketball. It’s incredible to watch LeBron James catch an alley-oop with the left hand on purpose. When you see him do it on purpose and dunk it, there was a thought process there that he had in his head. Everyone watching it has a thought process of seeing him experience it. So I want to write about it in a way where you go, “I was thinking that same thing.” Some people read it and they’re like, “What the fuck is this bullshit? It doesn’t tell me anything I wanted to know.” They don’t watch basketball the same way. But other people read it, and it touches them, not because I’m a great writer (I’m not that good of a writer), but because I’m talking about a thing that you feel, too.
I do have a specific basketball question for you. Should Gregg Popovich actually run for President of the United States? Or is that just hype?
That’s just hype. Gregg Popovich is the general of the army, and he doesn’t want to answer to anybody but himself. He’s like his own boss in the Spurs organization. There’s no checks and balances there—he’s not built for checks and balances. So, no, I don’t think he’d run for president. He’d make a great one I’m sure. Maybe. Or a terrible one. I don’t know. But I don’t think he would ever actually do it.
Does it bring you some sort of relief to be entrenched in topics like rap and basketball during a time when things are as turbulent as they are right now?
I honestly don’t think about it that heavy. It’s a cool thing to be able to do during the day for work, or whatever.
You’re making TV now and you have a series coming about The Rap Yearbook. How’s it been working with The Roots? How far along are you guys, and what major things are you learning along the way?
We start filming in January. They had to find a director, a showrunner and all these different parts and pieces. We haven’t started building it yet. We have like, a deck, where they make everything to pitch the idea to the TV stations. They didn’t even really need me for that, I just added tweaks.
I’ve had some experience working on the other show that’s coming, the sitcom, but all that’s taught me is that I don’t know anything about TV writing and phrases and schedules or anything like that. I thought it was a much more straightforward situation. You have to write a template for it, then an outline for it, and each time it’s got to go through a bunch of people, so it’s a very complicated, interesting process and it is difficult. And the only reason we’ve made it this far is because Mike Schur, the other guy attached to it, he’s been in the playoffs already. He knows all the tricks. I just do what he says.
Could you tell me exactly how much money you raised overall for hurricane efforts?
Yeah, we did $134,000 in 10 hours. And then we turned off the fundraiser. All told for this year, just fundraised through that same group of people, the FOH, is somewhat closer to, I haven’t looked through all the paperwork, but it was somewhere between $175,000 to $200,000 this year, just cash donations.
Even with the knowledge of how the internet works, that had to shock you.
Yeah, definitely. We’d done fundraisers before, and each time we did them we’d raise like $12,000 or something. Or $10,000. It was not a big amount of money. But the hurricane stuff, when that happened, it was like, “Oh fuck, we did $10,000 in the first 12 minutes,” or something crazy like that. If I would’ve left it open, we would’ve gone over $250,000, easy, no question about it. But I got nervous because it was a lot of money and I’ve never handled anything like that. I thought I was going to go to jail, so I just turned it off. I started it at night, maybe 7 p.m. one night. I went to sleep and woke up the next morning, and I saw it was in there. I was just like, “Fuck. Abort, abort.”
Then I tried to get ahold of my accountant and a buddy of mine that’s a lawyer, just didn’t know what to do there. It was scary. But then PayPal reached out, and Venmo reached out, and they walked me through everything. So I didn’t even have to put the money in my bank account, it went straight from PayPal and Venmo, we connected them with all the non-profits—there were seven of them—and they facilitated moving everything straight to them, I didn’t even have to pay. They were really helpful.
In your own words, what does it really mean to be an influencer? Whether you’re one deliberately, or by default.
I would never call myself an influencer, but if I had to define it, it’s exactly what it sounds like. You’re just a person that does a thing, and other people see it, and they say, “Oh, I could do that. I want to try that. I want to experience that thing.” I think that’s a part of the reason any of this stuff has been successful, because the whole point of me doing anything was always me just trying to tell other people, “I didn’t have any experience when I started this shit.” I barely got into college. They had me on like remedial classes. I’m not smarter than anybody. I’m more creative than other people. So if I figured this shit out, you can do it too. That’s really, to me, what an influencer is, somebody who makes other people feel like a thing is cool, and maybe they want to experience it or try it, too.