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The Rap Yearbook author Shea Serrano on building a tiny utopia on Twitter

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Shea Serrano — New York Times best-selling author, newly-minted The Ringer staff writer, beloved Grantland alum, former high school teacher, and father to a YG backup trio he calls only Boy A, Boy B, and The Baby — is the easiest person in the world to get in touch with. For his nearly 90,000 Twitter followers, office hours are almost always open. He holds court daily on matters ranging from basketball to Taco Bell to Young Thug to parenting to the injustices of unpaid content creation.

It was mainly on the back of this enormous following (one of his most enthusiastic adherents is Hamilton creator Lin-Manuel Miranda) that he turned The Rap Yearbook, an anthology of the best rap songs of each year from 1979 to 2014, into a bestseller. Some of his fans have bought his book multiple times — not as gifts, just to have more than one copy. On Father's Day, Serrano egged on book sales by telling his corner of the Twittersphere that leaving a copy of the book on a porch overnight would summon any absentee father into the kitchen, coffee in hand.

"today's the day you prove those bitches wrong."

But it's not a "buy this book" spam account: people who tweet pictures of themselves in bookstores with copies of TRYB, bemoaning the fact that they're short on cash are encouraged to steal it. Periodically, Serrano will tweet out his email address so that anyone can ask him for advice on making it as a writer. He tweets daily encouragements like "today's the day you prove those bitches wrong," and "it's lovely to see people I like happy but it's way better to see people I don't like unhappy shoutout being petty forever."

Turns out, you can be wildly successful just by making everyone love you. So I asked Serrano how to make that happen for me (or you).

This interview has been edited for clarity and length.

Kaitlyn Tiffany: So, just to give everyone some context, how did you start writing?

Shea Serrano: I started writing probably seven, eight, or nine years ago, something like that. I was working as a teacher, and I just needed to make some extra money to pay bills. I couldn't get a part-time job since I already had a full-time job — I was applying at Target or to be a waiter, but nobody would hire me. I was literally Googling "at-home jobs" and writer was one of them. So I was like "fuck it, I'm a writer now."

I started calling the newspapers in town. There's a bunch of smaller papers in Houston, and I was hitting these guys up trying to wiggle my way into a spot. Once I got started in Houston, I moved up to the big weekly paper here, The Houston Press. And then I used that to flip it into other jobs at other places, I was just trying to move up to whatever the next biggest spot was. I was freelancing at a bunch of different places and Molly Lambert, who was a staff writer at Grantland, saw a thing I wrote for LA Weekly. She hit me up and asked if I wanted to pitch to them. So I started freelancing for them — I did that for like a year — and they offered me a job. There you go, there's Grantland.

KT: I read this interview you did with GQ where you said that you would write until 2AM and then get up at 6AM to teach. Is that serious? That sounds horrifying.

SS: Yeah, that was when I had already been doing it for awhile and I was getting a lot of work. My days are super scheduled out — I know exactly what I should be doing at what time. A tight schedule was the only way that I was able to keep everything organized. It wasn't every night that I had to stay up until two, but there were some nights when I would stay up later than that or just not go to sleep at all until the next day after work. It's tricky when you have a full-time job and then you get to a spot where you're writing basically full-time hours as well. It's not an easy thing to do, you have to really commit.

KT: Obviously you have this huge, very passionate fan base on Twitter. How long have these people been with you?

SS: I would guess it was around the time I started at Grantland. That was when the readership started to grow the fastest. In the beginning I wasn't on Twitter that much and I was just using it to get people's contact information. Once I noticed more and more people were using it more and more regularly I was like, well let me try to be in on this thing and figure out how it works. Grantland was helpful because once you land at a place like that, it's validation. You don't have to explain yourself anymore. It's like "okay, well you work at Grantland so you must know what you're talking about." And, it just fills itself in after that.

KT: So, who are these people who are following you? Are they kids, are they dads?

SS: I couldn't say. There are a lot of them now, maybe 80,000 or 90,000, so I don't get to interact with every one of them. But I do this thing maybe like once a month where I put my email address out there and say "okay if anyone has any questions about anything I've got some time, let me try to answer them right now." So, I'll always get 100 emails or so before I take it down. It's a big group: the emails come from kids in high school all the way up to other dads who are in their thirties and trying to be writers.

KT: The adventures of Boy A and Boy B are the only parenting tweets on the whole Twittersphere that are actually funny, and not gross. Do you think you'll keep tweeting about them once they're of Twitter age?

SS: Probably. I imagine so. It will just be a little weird in the beginning. They're a big part of who I am as a person now. That's mainly my whole existence: trying to make sure that they don't die.

KT: When did you first realize that you could make stuff happen with a tweet? Does that feel like a superpower?

SS: No, it doesn't feel like a superpower. You never know that something is going to work out. I remember when I first started using Twitter I was working at the Press and I was doing this thing every week where I was asking one specific question to a bunch of different rappers. And it became impossible to try to get these guys on the phone and it also became impossible to get them to return an email or a text. But for some reason if I asked them on Twitter then they would respond back in a few seconds. All of a sudden this guy who I could never get on the phone ever, he's just available 24 hours a day. So that was around the time that I realized you can really use Twitter to get some things accomplished.

KT: Your presence on Twitter is almost exclusively positive. You're not involved in the drudgery of media Twitter at all. How do you stay completely separate from that?

SS: What's media Twitter?

KT: Like, everybody in media subtweeting each other's articles or complaining about Facebook algorithms or whatever.

SS: That's just not interesting to me, that's all it is. I just don't want to spend a bunch of time writing about a thing that I don't like, because it seems counterintuitive to me. I only want to talk about the things that I like and if you only talk about the things that you do like then it just becomes an easier way to be happy. It's the same thing where if an article comes out and I read it and I like it, then I'll talk about it. Like yesterday, I read this piece by Jia Tolentino from Jezebel — it was about Abigail Fisher and it was fantastic. It was just a smart, well-written thing so I talked about that a little bit because I thought it was so great. For me it just makes more sense to talk about the stuff that I like.

"i only want to talk about the things that I like."

KT: Speaking of stuff you like, did you get flack for any of the songs you picked for The Rap Yearbook? I feel like maybe naming Young Thug the best song of 2014 over Kendrick could have been controversial.

SS: No, I didn't. I think time has already proven that Young Thug was the correct choice. If you look at 2015, the biggest thing in rap last year was Fetty Wap. He was the most successful rapper last year as far as radio play and what rap was sounding like. And that was because he basically just took what Young Thug was doing and made it a little more accessible. Not too many people were upset about that.

KT: That's so great. If I ever said something like"this is the best rap song of the year," there would be dudes in my mentions for 100 years. Maybe you just have nicer readers than I do!

SS: It's so, so bad if you're a woman on the internet and you say... anything at all. For me, Twitter has mostly been a very positive experience and just nice things are happening to me all of the time on there. But I remember one day I was making some joke about basketball and Katie Nolan — who has a TV show where she talks about sports and is a very popular lady — made a joke back at me about it. The next 45 minutes were just a bunch of very aggressive and mean dudes shouting at her and I was like "what the heck?" It's awful, I don't know why anybody would want to be a part of that.

KT: The only not explicitly positive thing about your Twitter is the emphasis on being petty. Can you explain that life philosophy a little bit?

SS: It feels good. It just feels really, really good to do something out of spite or pettiness. I feel that tug all the time of wanting to do something just because somebody said I wasn't going to be able to do it. I assume everybody has that same feeling inside them. Let me embrace it. I don't want to run from it. A lot of the stuff that I've accomplished, it's all small stuff, but it was always because I was picturing the person at the end of the day that I wanted to see it. I wanted them to see it and feel bad, because there are people who I don't like and whenever anything good happens to them I just feel awful inside. So, I want them to feel that.

KT: Oh, yeah, for sure. I tweeted at my junior prom date who called me the c-word when I was at a Jake Gyllenhaal movie premiere.

SS: What movie was it?

KT: It was Demolition. It was very bad. It was a very bad movie.

SS: I'm gonna watch every Jake Gyllenhaal movie though. Every single one. No matter how bad it is, I'm gonna watch it. Did you see the one with the twin?

KT: Enemy, yeah.

SS: What did you think of the ending there, with the gigantic spider?

KT: I had no idea where the spider came from. I had no idea if the two Jake Gyllenhaals were the same Jake Gyllenhaal. I didn't know, and that movie made me furious.

SS: That was so scary, when that spider was there. That was probably one of the creepiest movie moments I've ever seen.

KT: And now that director is just making boring drug cartel movies. Tangentially related to Jake Gyllenhaal, I was re-reading a piece you wrote for Grantland in which you talk about how much you love Kevin Spacey. Have you seen the trailer for his new movie where he gets turned into a cat?

SS: That was very disappointing. I don't know how that happened.

KT: He's just embracing the next logical step of his career!

SS: No, that doesn't have to be. You can be old and cool. Clint Eastwood never did a movie like that. You know what I'm saying? And Spacey is in a cool space right now because of House of Cards. Although he probably got paid a whole $10 million or something so I guess if you have to pretend to be a cat, go for it.

KT: Yeah, I would do pretty much anything for money. I guess you're getting up to the celeb status where this becomes a question — would you do sponsored Instagram posts?

SS: I don't have Instagram but I would set one up. I don't know if you're allowed to do this, but if Wingstop hit me up and said "we're gonna pay you a thousand dollars to tweet about us," then I would just tweet "Wingstop gave me a thousand dollars to send this tweet about Wingstop" and then that's it. I think if you handled it like that then people would just go "oh, that's kind of funny." But if you're like "ooh, this delicious Wingstop, available right now" I think that's corny. Maybe the best thing to do, would be to just take that money and give it to someone else. Then you're a good guy.

KT: And then you're almost up to club appearances. That's the real money.

SS: I'm gonna do that. Show up with Pauly D and get paid.

KT: So, what's the secret? If I want to become a New York Times bestselling author, what should I do tomorrow as the first step?

SS: The first thing I would do, knowing all the stuff I know now, is make a Twitter. You have to build up your followers big enough where you basically have all of the leverage. To get on the New York Times bestsellers list you probably have to sell between 10,000 and 15,000 copies of a book in a week. And I don't know another way to reach that many people at the same time other than using social media. So if you have an Instagram account with a million people or 50,000 people, that's where you market. I remember when I did the Rap Coloring Book, which came out before The Rap Yearbook, my plan was just to get Rolling Stone to cover it or to get LA Times to cover it. I thought that would translate into sales because I thought that was how it worked. But, as we realized with the second book, it's much more effective if you're just putting it in front of people yourself.

KT: So, make some friends on the internet?

SS: Yeah, if you have a lot of friends on the internet, you can cause some trouble. You can do whatever you want.