Before he was a best-selling author, a staff writer at The Ringer, and one of the rare souls still using Twitter for good, Shea Serrano was a guy Googling “work from home jobs.” He was a teacher at the time and needed to make some money after his wife, Larami, also a teacher, was put on bed rest after complications when she was pregnant with their twins.
“‘Writer was on the list, and they had a little section: ‘What do you need to be a writer? You need a computer and you need the internet,’” he says. “Well, I have those two things. So I guess I'll try to do that. I didn't have any journalism experience. I didn't know anybody. All I had was the computer and the internet and I figured that shit out.”
Figured that shit out indeed.
Starting out at a small neighborhood newspaper called The Near Northwest Benner, Serrano pitched, hustled, and wrote his way to freelance jobs at the Houston Press and LA Weekly, before catching the eye of Bill Simmons, then at ESPN’s Grantland. Since, he has gone on to land three of the four books he has written on The New York Times bestseller list (the one that missed it was his first, a coloring and activity book he did with the rapper Bun B.), and rode that same voice all the way to becoming one of culture’s must-follow voices on Twitter, particularly if you’re interested in basketball, movies, or feeling good about humanity. (Serrano famously leverages his extremely engaged following, just shy of 330,000 followers, for good, raising awareness and money for wildly diverse causes: $3000 for a parking lot attendant who helped him find his car, a scholarship for Latinx people in journalism, $134,000 for Hurricane Harvey victims in one night.)
So when we were looking for voices on confidence for season two of GQ’s Airplane Mode podcast, we thought: who better than a former teacher with a computer, the Internet, and a whole bunch of lessons to teach on how to ride your own wave all the way to the top?
Since you seem to be a universally liked guy, it makes me wonder: who was your first hater?
My first hater, professionally, was probably this guy that I went to school with. I think he wanted to be a writer as well, so when I started popping up in the Houston circles doing writer things, he followed right behind me to comment on the first few articles I was writing. He would just always say something not nice.
What about as a kid?
Do you count a bully as a hater?
Oh yeah. Then a bunch. There's a guy I've mentioned in interviews before. His name is Albert, and I went to middle school with him. He stayed picking on me. And I never forgot him. And also this other kid named Jose, who I eventually ended up getting in a fistfight with.
How’d that go?
It was one of the few fistfights that I've gotten into that I actually won. But I only won it because I cheated. He started picking on me in seventh grade, or something like that. In 10th grade, I'm walking in the cafeteria, and, from behind, I feel a big shove. I was holding a little basket of fried shrimp and french fries, and a Barq's root beer. I stumbled forward, I dropped my french fries and shrimp. I turned around and I saw him, and I was just so filled with rage, from three years of being picked on, that I just chucked the Barq's root beer at his head as hard as I could. It hit him in the face. He stumbled back, and I just jumped on him. I'm in tears at this point. If you remember A Christmas Story, when Ralphie finally beats up that one kid? It was like a Mexican version of that.
That sounds like a shameful waste of a Barq's root beer.
[laughs] Barq's had a tagline at the time: "Barq's has bite," or something like that. And I wish I would have thrown the soda at him, beaten him up, and then stood up and been like, "Barq's really does have bite." Some fucking action movie shit.
I know on Twitter you talk about the love of being petty, and just wanting to do something because somebody has said that you maybe weren't able to do it. How much of that sort of grudge mentality has actually driven you?
Most of it. I think the only two reasons I really ever tried to do anything—I wish I was more mature, I wish I was in pursuit of self-actualization or something like that—has always been because I was trying to impress somebody, like Larami, my wife, who I started dating in college, or I was trying to fucking shove it in somebody's face that they said I wasn't going to be able to do a thing.
How'd you get up the confidence to pass Larami a note? I read that you originally met her by passing her a note in sociology class.
That sounds about right. So this is in college, and Larami is a very attractive woman. I'm like, "I would like to talk to this woman, I'd like to get to know her a little bit better." But I knew because she was an attractive woman, that she was probably getting hit on multiple times a day every single day since she arrived at school. I didn't want to be another one of those people.
So I tried to think of a clever way to do it. And I didn't have her email—I didn't want to send her an email even if I could find it. I learned on Cruel Intentions that that is not a romantic thing to do. You don't just email somebody.
So I was like, "Oh, I'll just hand write a note and pass it to her, like we're in middle school again,” or whatever. It said something along the lines of, “This is who I am. I'd like to get to know you a little bit better. Here's my number if you want to talk some time.” And then I fucking booked it out of the class as soon as I sent it to her. I was like, "Ah, this isn't probably going to work out that great for me, so I'm just going to get ahead of it." And then two days later or something, she called.
That seems to me to be the same radical authenticity that you bring to Twitter. "This is me. If you like it, here I am."
I don't know if it's the best way for me to be, but it's certainly the easiest. Because if you start trying to just build up a thing that you aren't already naturally, then this means you have to remember a bunch of shit. I don't have to remember lies that I've told.
How did you get into writing originally?
The short version of the story is Larami and I were both teaching at the time. We were getting married, she was pregnant with twins, and a few months into the pregnancy she had some pregnancy complications. They did this emergency surgery and were like, "Hey, you can't work anymore. You have to be on bed rest for the next few months. If you get up, the babies are going to come out and if they come out, you're going to die, and they're going to die. So good luck."
All of a sudden we're going from living off of two teacher salaries—which you can do if it's two people living in Houston—to preparing for a family of four, making $45,000 a year. The numbers weren't in our favor.
I needed a way to make extra money. I was applying at Target, Pappadeaux, grocery stores, whatever, but nobody would hire me because I already had a full-time job. And so I was Googling “work from home jobs” and writing was one of them. Writer was on the list and they had a little section: “What do you need to be a writer? You need a computer and you need the internet.” Well, I have those two things. So I guess I'll try to do that. I didn't have any journalism experience. I didn't know anybody. All I had was the computer and the internet and I figured that shit out.
When you first started, were you like, "Oh I can do this," or were you kind of like, "Let's throw some shit at the wall and see what happens?"
It was more of the second thing. To get us through each month, I needed $500 extra. I'm reading stuff on the internet that’s like, “Here's how you make six figures as a freelancer." And I was like, "These writers are getting paid”—I didn't know until later on that that's really not how it works for most everybody—”if people are making $12,000, $15,000, $20,000 a month writing, I should be able to find $500. So, I'm just going to pitch everybody.”
Did you keep yourself on a strict pitching schedule?
Oh yeah, dude, I was pitching so much shit all of the time. Because I read in my little books that I bought about freelancing that you're going to have a very low success rate, especially in the beginning. You might pitch 25 things and maybe you hear back about one. So I was like, "Okay, I got to do that. I got to pitch 25 things every week.” I was hitting every editor's email I could find, even if it didn't make sense. In the beginning, all you're looking for is somebody to email you back. Even if it's a no, you’re like, alright, cool, I'm getting somewhere."
How much did self-doubt plague you when you were sending those pitches?
Well, it's always there. Even now. Even after whatever little amount of success I've been able to put together. I have already pitched like three or four things this week that all got turned down. And every time a thing gets turned down, it feels less like they're turning the idea down and more like they're turning you down.
There's no way to make it any easier or make it sting a little bit less. You can read whatever advice you want, I can tell you whatever I want, but this is like me trying to explain to you what it's going to feel like to get punched in the face. Eventually you just have to get punched in the face. None of the words I say are going to make it hurt any less.
But also, I know, especially at that point, that I have this much money every single month that I am responsible for. And if I don't do the work, then I don't get the money. If I don't get the money then I don't pay the bills. And if I don't pay the bills then everything in my life will start to fall apart. So either you're going to do the thing or you're not going to do the thing.
I'm curious where and when you came to that realization.
I know exactly where the genesis of that was. And it didn't have anything to do with writing.
I started playing pool—like a lot—right before I left for college. I was playing ever or every other day after school. When I got to college, they had a pool hall on campus and I started playing there every day— six, seven, eight hours a day—and I was getting good at it. I started playing pool for money. Not a lot of money. But if you're in college and you make $30 in a day, you feel like you're the king of the world.
I was in the middle of a game, playing with this guy named Randy—it's one of the first or second times that I've ever played for like $10 or $20 and I'm real, real nervous—and a buddy of mine, Damon, in my ear, he's like, "I can see how nervous you are. Listen, one of you two is going to win. Why not you?" And for whatever reason that just stuck in my head. Somebody's going to win here, so it might as well be me.
I just try to carry that forward with any of the stuff that I want to do. It's going to get done eventually. Why can't it be me who's the one who does it?
Now you’ve written three New York Times bestsellers. I’m wondering how that informs your confidence now.
It’s not so much that I feel like, "Oh, I've reached a level of talent or ability. I'm up here with the top level people." What it feels like is, "Oh shit, I was able to do this thing that this other person was able to do. Maybe we're all idiots." I'm like, oh, if I was able to do this thing, maybe the people who—if we're talking about movies—maybe the people who make movies, maybe they're not a million times smarter than me as well. Maybe the people who built a building aren't a million times smarter. Maybe they just put the work in and that's why they were able to do it. It just made me feel like maybe there's no magic trick here. Maybe you go through the process, you understand what it takes, and you're like, “Maybe if I just do this with everything, I have a decent shot at it."
There's definitely a class of people who are just innately more talented than everybody else. Just born to do a thing. If we're talking about writing, for example, I might read a column by Wesley Morris or Sean Fennessey or Jia Tolentino or Doreen St. Felix and go like, "Oh shit. I can never write in this way. I can never think in this way."
But for the most part—everybody else, the other 97% of us—we're all operating with the same basic tools, and it's just a matter of who's going to outwork the other people. You're either going to have a great connection, you're going to be born into a thing, or you're going to have to fucking outwork all the other people who are trying to do the thing. I didn't have the first one so I guess I'll try the second one.
Has the success changed your expectations for yourself? How do you keep it from creeping into your writing process?
It's easy to keep it out of the process because I'm not seeking out any of the comments. I just put it out there and then I don't worry about it anymore. I don't want to read the Amazon reviews because certainly somebody in there is saying something not nice. In my head, when I'm writing this stuff, I'm trying to write it for me or for the people I know are going to like the thing that I'm talking about. The success doesn't affect that too much.
Where I do feel it, though, is that there are expectations now that come with whenever I put a thing out. When The Rap Year Book came out, nobody thought it was going to do anything. They thought maybe it’d sell 15,000 copies in two years, so 500 copies a month. That's not a ton. Then it came out and it sold 8,000 copies the first week or something like that. We all got to be surprised. They paid me like $25,000 before any of the agent fees or illustrator fees or taxes. It took two years to do. There was no real expectations there.
But it comes out and it does really well and they're like, "Oh, let's do another book." And we do Basketball (and Other Things) and now I'm starting to feel it a little bit because they're like, "Oh, if the last one did 8,000, what could the new one do?" Then that one comes out and that one’s number one on the bestseller list. And the publishers are like, "If that one did this, what do you think this new one could do?" And you start to feel that. You feel the pressure of those expectations. You start to sort of internalize it, and that's when it gets scary and intimidating.
Prior to Movies (and Other Things) coming out, I was super stressed out. I was having nightmares consistently: something is chasing me and it's going to catch me. I could just feel that pressure on me. And again, this is self-imposed. Nobody at the publisher was like, "It needs to sell this many copies." It doesn't work like that. They just pay the money and you write the book and you sort of cross your fingers and hope.
You are able to inject a lot of goodwill into the universe at a time and in a place—specifically speaking of Twitter—where that seems to be increasingly rare. Where does that positivity come from?
I have been lucky enough to have several people in my life who I know care about me a great deal. It probably starts there.
All of the philanthropy stuff that we do on Twitter, I think that's residue of being a teacher. I was a middle school teacher for nine years. When you're in that position, there's a chance every single day for you to do something that's going to be meaningful in somebody's life. You can see it happen after you've been teaching for a while. You see it in a kid's face—like, oh, that was important to that kid. You had that chance literally every day you went to work. That was always there and it was always something I was trying to chase.
And writing has been really, really good for my ego. Because nobody asked me to come be on podcasts when I was a teacher. Nobody wanted my advice about anything when I was teaching. They ask for it now because I'm a writer. But teaching was better for my heart, because it allowed for those opportunities.
On Twitter, I'm like, "What's a way for me to like replicate that feeling?" And it turns out giving money to people makes them real happy—which is not some profound statement. But if a person has a medical bill or they need to pay for a thing or we're just making a donation to a nonprofit and you show up with $25,000 to give to them, everybody feels good about it. You feel good, they feel good, the people who contributed feel good. It's like replicating that teacher feeling all over again, in a quick dose.
Of all the times you've bet on yourself, I'm curious what you would consider the biggest shot you ever took?
Just from all of the things that followed afterward, it would definitely be sending that note to Larami. In the background of every single story that we've talked about, of every single idea or thought, Larami has been propping me up, telling me in my ear, "You can do it, you can take care of a family, you can be a husband, you can be a father, you can be a writer.” Larami has always, always been there. And I mean very much in practical ways. When I first started writing, she was editing my stuff. So in those sorts of ways. But also in this big ideological, philosophical way. I think if I don't send that note, if I never work up the courage to write this thing on a paper and pass it to her, I think everything looks much darker and much bleaker and you and I are not having this conversation right now.
This interview has been edited and condensed.
Originally Appeared on GQ