[THE MAIN EVENT]
From eighth grade science teacher to journalist to show creator, the multi-hyphenate knows how to graduate to the next level. Serrano spoke with UpRising about his unlikely journey, dealing with rejection, and staying grounded
UpRising: So many writers dream of transitioning from contributing to publications like Grantland or The Ringer to books and ultimately, television. Was TV always the end goal?
Shea Serrano: No. When I was a teacher, I thought I was just gonna be a teacher for my whole life. That was the dream job that I wanted growing up. The writing stuff just kept growing. It kept doing a little more and offering a little more each time I would do a new thing. And so I'm just like, "Alright. I'll try whatever." It wasn't my idea to write a book—that came from the publishers. This woman named Samantha Weiner who was at Abrams Books emailed me; The Rap Year Book was all her idea. I was like, "Cool. I'll try that." I made the bestseller list. The basketball book did even better. Then, TV people started showing up. Both books got adapted into shows and agents were like, “Oh, you should try and just create your own show.”
Seems like things fell into place versus you wanting them.
It was never something I was trying to chase down. Just something that I was backing my way into. With Grantland, I did a part-time contract but I was still teaching. Then, I got a phone call from founder Bill Simmons and Chris Ryan, who was an editor over there. And they were basically putting a full-court press on for me to write full time. They're very charming people. So I was like, “Alright. I'll try it for a year.”
Then Grantland shut down in 2015.
I signed a contract to go to Grantland in June of 2015. I started in July and then in October, ESPN closed it down. So three months after leaving this teaching job that I loved and was very secure in, me and all my friends got fired. And it was like, oh, welcome to journalism. That was not-an-awesome-time for me.
Maybe it’s good that being in the entertainment industry wasn’t your lifelong dream. You can roll with the punches when you face failures.
Yeah. That's very accurate. Because if I got fired from teaching, that would have been a crushing blow. But when Grantland shut down, in my head, I'd be back to teaching next school year. But that same month The Rap Year Book came out [and] made the bestseller list. It was a high and then a low.
Although you’re a bestselling author, you launched your own independent publisher Halfway Books as a way to disrupt the industry.
I started Halfway Books in 2018. I had already done two books and was working on a third. I felt like I had enough experience making a book and I wanted to do it all on my own. I remember getting my royalty statement in 2017. My books had done well; I thought it was super awesome. Then I looked at the statement—at how many books were sold and what I made—and wondered: Where's the rest of the money going? What if I don't have to give somebody else 85% of the money that I may make on a book? With Halfway Books, I could sell a 10th or a 20th of the copies and still make more money because it's all going to me. Each project funds the next project and that's really great.
Do you have distribution through a major publisher?
No. It's all on my own. There's no ISBN number for the book. I'm making a PDF or hiring people and we're building a digital book. And then I just collect directly through my website. There's no physical product. You can't find it anywhere. Once you buy it and you have a PDF, you can sort of do whatever you want with it.
Being independent is very freeing but it's also great if you do want to work with the establishment, having them come to you rather than begging for acceptance.
After Halfway Books started doing okay, other publishers started reaching out. Do you want us to build it? We’ll distribute your book. And I was like, "no." I just wanna do it myself and sell only a few copies and not have to worry about any of the other parts. Putting out a book is so stressful. You gotta do the media cycle. You feel like, If I don't sell enough copies, I let everybody down. What if somebody loses that job because my book didn't do well? This other way, I'm the only one who's at risk for anything.
You've launched multiple shows rooted in your personal experience and the Hispanic experience. Was it important for you to spotlight your culture and have that representation in the stories you tell?
It wasn't intentional where I sat down and said, “I wanna make a show about four non-white friends or a family of non-white people." You write what you know. I just wrote a thing that I felt comfortable writing and that felt natural. It works better that way. Any other stuff that I enjoy, it always feels like a natural extension of the person who made it. I wasn't trying to check off a box. I wanted to make a funny TV show and that's it.
Primo wasn't picked up for the second season. You described it as a “short but beautiful run.” How do you deal when something doesn’t work out?
I think you must be sad about it for a little while. And then you go make a new thing. Nothing lasts forever. You go into it anticipating at some point it's gonna be over. What are the other options? You get kicked in the chest and lay on the ground or you get up and try again.
Failure is an integral part of being a writer.
Rejection is baked into the job. And the people who are able to make a career out of it are the people who can get hit and just keep walking forward. The show got sent away sooner than we thought. [What] made it easier to deal with was the show got wonderful reviews from everybody who watched it.
Does that make it worse? You know you had a good product but you can’t control all of these other factors?
I just tell myself that we did what we were supposed to do and it didn't work out. I am proud of the thing we made and I feel good about it. I guess it's a little bit frustrating that you could do all of the things and it doesn't work out. But that's just sort of how it goes.
What advice do you give to writers in the current content landscape?
You gotta know that your stuff's not always gonna work out how you want it to work out, and you're gonna experience way more failure and rejection than you are success. Somebody's gonna get to do the thing you wanna do. So just go in until it's you who does it. Make a thing that nobody's made before. Write a sentence that nobody's written before.
—Sowmya Krishnamurthy
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Binge Serrano's Neon on Netflix, then tap into Primo on Amazon Freevee. Drop the link to his NYT bestseller, The Rap Year Book: The Most Important Rap Song From Every Year Since 1979, Discussed, Debated, and Deconstructed, in the group chat and prepare for endless debates.
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