On the importance of doing your research

What’s the most important thing you ever wrote?

I have an article that has to go up on next Tuesday. That’s the most important thing. Whatever the next thing is, is always the most important one for me, because that’s the one people are going to look at. So I gotta make sure that one is good.

When you were a teacher, how old were your students usually?

I taught 8th grade. My kids were like 14, 15.

That’s a difficult age to teach, I’m told.

I’m sure every age has its difficulties. I taught 7th grade for one year and thought it was harder than 8th grade, mostly because the kids just didn’t know anything yet. It’s better when they’re a tiny bit more mature. Sometimes it was hard, mostly it wasn’t that difficult. They’re just kids, you know.

I was wondering how much “teacher” is still in your writing. It has all these modes of argumentation, of debate, using graphs to make a point…

Yeah, that’s the trick. Every article has some sort of point I’m trying to make. It’s just a matter of writing towards that point. Sometimes, the point is a silly or ridiculous thing. Either way you want to make sure you’re writing towards the thing that you’re trying to accomplish.

You went from a job that parents tend to be proud of–rightfully so–to a job that might be hard for them to understand. Do your folks get what you do for a living?

I don’t think they understand it, really. They never get to see any of it, you know? When you tell somebody you’re a teacher, then your parents go “I understand, I know exactly what this is.” When you tell them you’re a writer, that doesn’t mean anything, because they never have any experience in that world, so they don’t know what it is, or how big it can be to some people. It wasn’t until I made a decent amount of money that my Dad was like, “Okay, I get it now.” That’s the thing people can understand. If you say, “I make more now than I did teaching,” they can go “Oh, this is a real thing.” Prior to this they’re like, “This is a hobby.” [laughs]

You’re best known for The Rap Year Book and Basketball (And Other Things). For the longest time, the main divide for both rap and basketball has been between East vs. West. How important was it for you to grow up on neither of those coasts but in Texas?

Here’s a thing I realized later–and this was after I had fully gotten all the way into writing. When you’re in the South, or when rappers specifically are in the South, it’s not one of the target markets for all of the big record labels. It was hard for rappers to get the attention of somebody in New York or LA when you’re down in Texas. So what they did, rather than trying to work that out, they said, “Screw it, we’ll do our own thing.” They figured out ways and built up systems so that they could survive on their own. We don’t need to be nationwide famous if we’re Houston famous. Houston is enough to support us.

That was a thing I’ve picked up on when I started writing. You don’t need to get a giant, big deal with a place, you can just build up your little area. This is probably an easy way to understand that: you can get your own book deal, and every book you sell you’re going to get a dollar off of the book, and you might sell a 100,000 copies that way. Or, if you just do it yourself, you’re going to make $10 every copy, and you only need 10% of what you would’ve sold otherwise, because more of it is coming to you. You just build up your own little market. That’s a thing that to me was very helpful as far as growing up in Texas.

Transitioning from teacher to writer, there was a sense of necessity more than vocation for you. I imagine there was a lot of cold pitching at that time.

Yes, I pitched everybody whose email I could find. It didn’t even matter what the place was. Every single place I could find an email or figure out an email for, I just pitched them. Hundreds and hundreds and hundreds of pitches in the beginning. And sure, most of them were either ignored or rejected. That’s the way that the game works, the way that it’s built. That’s, of course, not a unique story about writing—I still pitch stuff and it gets rejected. But yes, in the beginning there were a lot of cold emails, cold pitches and it was super-sucky [laughs].

Sometimes when a pitch gets accepted, that can be a scary moment, too—all of a sudden you have to deliver on the thing you randomly offered. Where did you get the confidence from at the time?

More than anything, it was less about confidence and more about ignorance. I didn’t know any better. I didn’t know that I was supposed to be nervous or scared. And I had a couple of people from early on–there was a guy called Henry Abbott, he was a big writer and editor at ESPN, and he said some nice things to me over an email one day. Little things like that can help you pump up your chest a bit. But more than anything, I didn’t know any better. All I knew was if I wanna get paid for a thing, I need to do this part, so I’ll do this part.

You once wrote how hearing The Fresh Prince & Jazzy Jeff’s “Nightmare on Elm Street” was the first time that “pop culture had been folded over onto itself” for you. This folding of pop culture seems crucial to how you work.

Yeah, that’s definitely accurate. I think that was another trick I learned when I was teaching. If I’m trying to explain something to a kid and the kid doesn’t understand what I’m saying, I always try to make some sort of analogy. Like, “Look this is similar to this” and they go “Oh, okay now I understand why the periodic table is set up this way, because the left side of the periodic table is one rapper and the right side is another rapper and they don’t get along.” It’s the same thing with writing. If I’m trying to tell somebody a thing about basketball, but they don’t know a lot about it but a lot about movies or music, then I can go “It’s like the scene in that movie.” It just makes things easier to understand and also it’s just a lot of fun.

Your writing style is very conversational. Do you think that you’re hard to edit for anybody but yourself?

You would have to ask the editors but I’m sure it kinda sucks sometimes [laughs]. Usually there is a feeling out process. The editor I have now is this guy called Donny Kwak, and the first eight pieces or so I was figuring out the things he’ll let through in a story, what he likes or doesn’t like. He’s figuring out the stuff I wanted to do and we meet up in the middle. But yes, I imagine it’s a little tricky to edit.

Is it generally easy for you to accept second opinions about your writing?

Yeah, if he goes “You did this part wrong,” then I’m like “Cool, I get it.” Donnie never adds stuff in or tries to change stuff, he just makes it a little tighter. I can’t think of a time in the last year or two that we’ve been working together where he made a change and I said this is not gonna work for me. No editor is trying to make your article worse. I just roll with whatever he feels and then I just try to add in my little notes, like “Can we not do this, can we not do that.”

Pop culture and sports writing mostly comes from a strong point of view, very much in favor or strongly against something. In that regard, there’s almost a kinship between the critic and the fan. You play with that in the “Overreactions” columns, for example.

I’m not sure if it has to be that way, but I’m sure it’s helpful! The “Overreactions” articles are fun to write, because it’s making fun of the way people respond to sports. The point of that article is to poke fun at people who react a certain way. But yes, if you’re writing something you definitely have to have a viewpoint or data set that you’re trying to get across, because otherwise what’s the point of doing it? Why are you writing the thing if you’re just gonna go “I don’t know about this…” It’s hard to write about music or movies or whatever if you’re not a fan of the thing you’re writing about. And if you are, you probably care a bunch about it, so hopefully that comes off in the writing.

Do you write a lot of negative reviews?

No, I don’t do any of those. The closest I’ve come is explaining why I don’t like a certain rapper. But beyond that, no. It’s just not fun to me. The whole point of writing for me usually is that I want to celebrate something, or cheer something on. I don’t want to write an article about an album I didn’t like, because that means I gotta listen to that album for 10 hours and research about it for another 10, and that’s just not fun. I rather wait until I find something I like and write about that.

Naturally, in your books there are parts about things that happened in your lifetime, but also some speculative things and some that happened before you were around. How do you maintain the same level of interest and accuracy for all those passages?

That’s because the same amount of research goes into all of these chapters. It doesn’t matter if you’re writing about a thing that you have a personal connection to, or a thing that happened before you were paying attention. You still have to spend 35 hours or so reading about it, learning about the things that were happening at the same time, learning about the aftershocks of it, and so on. There is a certain number of hours you need to spend with each subject before you write about it, especially in the case of a book chapter. You’re going to spend two weeks of your life researching a thing before you write it. That’s the way I write, anyway, I don’t start until I have done all the research. Once I’ve done that, it’s easier for me to feel connected to it. Even the stuff that you think you know about: when you try to write about it with any authority, you come to realize, that you don’t really know anything at all.

An easy example for me: my favorite team is the San Antonio Spurs. My favorite version of the Spurs that I ever watched in my whole life was the 2014 San Antonio Spurs. That’s my number one favorite team in the history of all the sports. That specific team I love more than any other team, I care about them a great deal. That said, I couldn’t tell you right now what their win-loss record was for that season. I couldn’t tell you exactly how many playoff games they lost. I don’t know that stuff off hand, even though they are my favorite of all time. So I’m gonna have to spend a bunch of time researching it. That’s just the way it works. When you’re researching a thing, you learn about it and you feel connected to it. When you watch a behind-the-scenes documentary about an artist that you never cared about, you may learn their whole story and feel like “this is meaningful to me, I care about this person now.” That’s what happens when you’re writing.

Can you talk a little about the importance of footnotes in your writing?

This goes back to what I mentioned earlier. When I’m writing a book chapter, there’s a point in the chapter that I’m trying to get. If it’s for the Rap Year Book, then I’m trying to explain why this is the most important rap song of this specific year. When I’m writing a chapter, the only stuff that I want to include in the body of the chapter are things that help me prove my point. The footnotes allow me to add in other stuff that I learned, or I found interesting while I was researching, that doesn’t necessarily fit in with the point of the chapter. Sometimes I come across a piece of information that doesn’t have to do with why this song is the most important. But it’s still interesting to me and that’s where footnotes come into play. Otherwise the writing would feel a little dry or a little one-dimensional to me. I want everything to be as rounded and thorough as possible. Plus, when you’re talking to somebody about anything, it’s never a straight-line conversation. Not for me anyway. There are always little tangents and branches that stick out along the way. So I want to include those in the book as well. It just feels more natural to me.

What’s your collaboration with Arturo Torres, the illustrator of your books, like?

Let’s say we’re working on a book. There’s a chapter that I’m writing about and I need some art for it—I will give him a general feeling I’m going for, and then he comes back with an idea. One example: In one of the chapters in the basketball book I was writing about disrespectful dunks. I knew I was going to write a long thing about Scottie Pippen because he has this very disrespectful dunk against Patrick Ewing. So when I talked to Arturo about this chapter, I told him the feeling of this chapter is kind of aggressive and kind of cool. I need some Scottie Pippen artwork where he looks aggressive and cool. Arturo suggested, “Let’s draw him in front of an explosion walking away from that.” He’s very good at that part of it, so I just try to stay out of his way as much as possible. I just want to give him a tone that we want to hit, because if I say “Draw this person doing this,” it’s going to be all I’m going to get back from him. If I just let him go wild, he usually comes up with something more interesting than what I have.

Is it necessary for him to be as well-versed about the subject matter as you are?

A lot of the stuff he doesn’t know so much about. He’s definitely not researching as much as I am. This is not just off-hand knowledge that I happen to have. I think people get confused a lot about that, they tend to think I just happen to know everything about rap or basketball. That’s not the case at all. With Arturo, he will draw whatever he wants to draw and then go nuts. With rap he had a general idea, but with basketball he didn’t spend a lot of time watching it, so he didn’t know much of anything.

We’re living in the era of the co-sign, it seems. Whether from esteemed colleagues or Barack Obama, your work has earned shout outs from influential names. How important is that to you?

That means a lot to me, it’s a big part of what I’m trying to do. Simply because that’s how I got in the game, if you want to call it that. That’s how I got into writing, somebody said “Try this guy out” to another person. I wanna make sure that, now that I’m in the spotlight, I’m doing this as well. It’s better that way, it makes everything more enjoyable. On social media, too—just as I don’t want to write an article about something that I don’t like, I don’t spend a lot of time on Twitter talking about a thing I don’t like. It doesn’t feel good, so I don’t wanna do it.