How Shea Serrano Finds Ideas (and Other Things)

You need to be reading Shea Serrano.

He's the best-selling author of The Rap Year Book and regularly collaborates with illustrator Arturo Torres, both on that book and others. He's a writer for The Ringer and ringleader of the FOH Army, a group of kind-hearted troublemakers, present company included, who have done things like swarm an indie bookstore with online orders and raise $134,000 in Hurricane Harvey relief.

His next book, Basketball (and Other Things): A Collection of Questions Asked, Answered, Illustrated, is due out October 10th and examines questions ranging from "Who is the greatest dunker of all time?" to "What would happen if Karl Malone switched places with a grizzly bear for an entire season?"

He's perfected a smart, off-the-wall, occasionally irreverent writing style that reads like a conversation among friends, and he's never short on new ideas. I chatted with him to learn a little more about his process.

Pop culture is at the heart of everything you do, but you blend your influences together better than anyone to create something that always feels fresh. Do you feel like you have to push yourself to take things one step further than most people would?

Well, I definitely do feel like I want to do things that not everyone else is already doing. I spend a lot of time trying to figure out ways to do that. Sometimes it works out well, sometimes it's a train wreck. But, you know, that's just part of the game.

What's it look like when you pitch a new idea to your editor?

If you're talking about a book idea or whatever, then the way that works is you come up with the idea, then you write a sample chapter, then you layout what the rest of the chapters in the book might be or look like (as well as a general overarching theme), then you send that to the editor (or possibly an agent who sends it to the editor or multiple editors). They decide if they want to make it, and if they do then they make an offer on it. If you're lucky, multiple editors will want it, at which point you'll be able to drive the price up a bit.

If you're talking about stuff for The Ringer, the way that works is every Friday I send my editors an email that has a few things that I'm interested in writing for the upcoming week. I spend that whole day at my desk digging through news sites and whatnot looking for something that I can turn into an interesting or entertaining story. But so I'll send those ideas in, and one or more of the editors will respond and say something is approved or something is turned down or they'll come up with a way to make a weak idea strong. There are other ways that stories happen for me (for example, one of my favorite ways is one of my editors emails me and says, "Here is an excellent idea for you," and it's an excellent idea for me), but that's the general way things go down for me.

Since The Rap Year Book, you've worked closely with Arturo Torres on a lot of projects - how has collaborating with the same artist across projects impacted your work?

I would say that the main benefit of working with him over multiple projects is I know who he is and what he's going to do and how he's going to respond to certain situations. Arturo is, in the clearest and most direct way, one of the best illustrators in the country right now. It's just a matter of knowing how to handle his idiosyncrasies, which is something that anyone who works with anyone creative knows a great deal about.

You've had incredible creative freedom under Bill Simmons, first at Grantland and now at The Ringer, and with editors like Hannah Giorgis. What has working in that space allowed you to do that otherwise wouldn't have been possible?

Mostly, I think it's just let me grow into myself at an accelerated rate. They've created this amazing work environment where the only thing they care about is that you're trying to make cool, interesting things. That's it. That's all. I've been working with Bill and Sean and Chris and Juliet and Mallory, in either a freelance capacity or full-time capacity, for a couple of years now, and never once has anyone ever said anything to me about website traffic or hitting numbers or whatever. The only things they've done are (a) pushed and stretched and pulled me toward being a better version of myself, and (b) assured me, time and time again, that the only thing I ever need to worry about while working for them is that I'm aiming my forehead toward good things.

As your work gets more attention, how have your changed your approach, if at all?

It hasn't changed much. All I really try to do is write things that I'm interested in or that I think are smart or funny. If you do that in as honest a way as possible, then you're doing it the right way.

Your voice, I think, is one of the keys to your success - it's always conversational yet instantly recognizable. What's something that helped you develop your voice?

I could give you some answer about how that's a thing that comes with just practice and persistence, because, despite the fact that that's a vague response, it's definitely true. But I'll give you something a little more practical that I figured out pretty early on that was very helpful. One thing I do basically every single time I write something is, before I actually sit down and start writing, I will talk the article through with someone. Doing so has two big benefits. First, it helps give the article a very natural feel and pace, because what ends up happening is you almost instinctively write the article in a way that mirrors the flow of the conversation. And second, it also helps you have a more rounded piece, because the person you're talking to will almost always say something or make a point that you'd not thought of or considered.

If you go back through and read anything I've written while thinking about that, you can see the bones of a talk I had with someone beforehand.

You've set a goal of 33,644 pre-orders for Basketball (and Other Things) - topping Kobe Bryant's career points scored in the NBA (33,643) - which could also put you at or near the top of the New York Times Best Sellers list. If and when you meet that goal - Disney World or Wingstop?

Wingstop. No question.

Basketball (and Other Things), featuring illustrations from the talented Arturo Torres and a foreword by Reggie Miller, is available October 10th. You can read more of Shea's writing at The Ringer and follow him on Twitter.