Ben Cory Jones is currently a writer on the hugely successful HBO comedy series Insecure. He chatted with Shadow and Act on the heels of his appearance at HBO’s popular POV presentation at the most recent American Black Film Festival where he gave a behind-the-scenes look at being a television writer and writing for Insecure in particular. He does the same here for Shadow and Act readers!

The Morehouse grad left school with degrees in both finance and literature and went straight to Wall Street to become an analyst. During his off-time, he worked on a passion project. “I was like you know what,” he said, “I have this one idea for a screenplay. I’m just gonna do that because I just have this one story that I want to tell. I went out and bought books and started the process of learning how to be a screenwriter. Little did I know I was unlocking a whole new career for myself. At the time I was like, oh, I’ll just write my one little story.”

Not unlike many who go into the finance field, Jones quickly found it wasn’t satisfying. He soon left his spreadsheets behind and joined the communications department where he wrote speeches for executives, promoted important business deals and created decks, among other things. “That was part of my getting out of corporate America and into writing, but it was still business writing.” Jones knew he wanted to write full time but continued with the same routine until fate stepped in and forced his hand.

The crashing stock market pushed the Memphis born and raised Jones to fine-tune his life even more. He recalled slight panic. “I was like, what’s happening? I just started taking screenwriting classes and writing classes while I was in New York.” Jones then headed to the West Coast. “I went to Los Angeles to try to be a writer–to write for television. I specifically wanted to do TV.” His proverbial “big break” took not only laser focus, but huge persistence. “I was trying to get into some of the diversity writing programs that are here in LA for TV writers, but ABC TV writing programs are very competitive to get into. It took me four years in a row of applying every year before I finally got into the program. And then from there, I got my job writing on my first TV show for ABC Family.”

In addition to taking a host of classes, Jones also made sure he spent significant time establishing professional relationships. One of the people he met was a young woman with the unlikely name Issa, who had a web series, Awkward Black Girl. “I was working as an assistant writer, and I think it was her first season of Awkward Black Girl. We would commiserate a lot about things like how hard it was in Hollywood.”

Between seasons one and two of working with Rae on Insecure, he wrote for other prestige series such as WGN’s Underground. Produced by John Legend and run by Misha Green, the action-packed historical drama depicted the lives of enslaved people in the American South. “I still consider myself a hardcore drama writer. That’s sort of how I taught myself how to write. It was important for me to do Underground,” Jones said. Being on the writing team for Underground also required a lot of homework. “We did a lot of research. I was reading slave narratives every night when I got home to prepare for the next day. In season two we did a lot about the Gullah, Geechee plantations and stuff. Those were rice plantations, so I had to learn a lot about how to plant and harvest rice. If anybody wants to know anything about that, ask me because we had to do with a ton of research!”

As much as Jones admired Issa Rae as they started out as young dreamers working to succeed in Hollywood, his admiration and respect for her has only increased now that he works with her regularly. Jones’ awe toward her work ethic is unabashed. “The writers spend about five to six months in a writers room,” he said. “We’re pretty much done unless there are rewrites. Issa’s job never stops, and her work ethic is incredible. I just really admire her. When you’re a producer of a show and you’re creating the show, the tone is set from the top down. And she set a wonderful, amazing, family-oriented tone for Insecure, so it’s no surprise that the show resonates with people because we all have a great time!”

These great times include rap battles in the writing room, something that is ironically unsurprising to hear. They are sometimes occasioned by one of Issa’s trademark “Mirror B***h” scenes. “Yeah, she pretty much writes them,” Jones said. “It depends on how she’s feeling in the moment or what the scene calls for. But, we do have rap battles in the writers room. Issa will judge them, and it’s the funniest thing because she really acts like she’s like Kid Cudi or somebody trying to judge our raps, and we’re just like, ‘Relax bro.’”

Jones is proud of the level of diversity in the Insecure writers room where they are encouraged to bring their personal experiences to bear in the script at times. “I believe it was nine or ten writers for season three, and we have a diversity of gender, diversity of race, diversity of sexual orientation. And it’s an extremely collaborative. I always say it’s like being at a dinner party for seven months. You sit around, and you talk about ideas. You pick, as your writers, people who have interesting lives. I mean definitely my time in New York City working on Wall Street, being from the South, you know, being gay. I mean these things are all things that I can use to pitch stories and to talk about.”

For people who aspire to write for television, Jones emphasizes that unlike other types of writing, even writing for film, writing for TV is a collaborative process. He said, “I just want to encourage people, don’t be in your apartment or your office by yourself. Get a team of writers to look at your script or get a person that you trust to read your work and give you feedback. You’re only as great as your collaborators. No one’s going to steal your idea. Even if they do, you should have plenty more. If you want to be a TV writer, you have to know how to work well with other people because it’s a brain trust on a TV show.”

o provide even greater access for those curious about the behind the scenes process of putting an HBO show together, recently Jones began participating in the HBO POV initiative and gave his first presentation at the American Black Filmmaker Festival in Miami this past June. HBO POV opens a window into the world of HBO through the lens of its talent working behind-the-scenes – focusing first and foremost on their expertise and the crucial role their craftsmanship plays on the quality of the network’s programming.  The master class series features intimate conversations that not only address the creative thoughtfulness required to do their jobs, but also the business and marketing practices that have led them to where they are today.

It’s also great having a team of writers to help you exercise discipline. Jones admits there are times when a writer will become attached to a specific character, or have a preference for the story moving in a direction that doesn’t work ultimately. Having other people in the room helps them to let go of the good and reach for the best. “We sometimes get into heated discussions about the direction we think Issa should go, or Molly should go, but that’s what creates great television. People behind the scenes feel very passionate about the choices that the characters are making. If the choices don’t feel true to the character based on what we know about her so far, then sad as it may be, it’s just what it is. We do the thing that not upsets everybody, but gets people really interested. We like to do the unexpected. That’s what we’re always trying to do.”

Speaking of directions characters are going in, Jones was understandably not able to spill too many beans about what happens to Issa and Molly in the upcoming season, but he did indicate that there will be a deepening of their sisterhood. “Issa and Molly have known each other for forever, and so it’s not a whole lot of conflict between them. They really support each other a lot more this season in my opinion. I would say they lean on each other a lot more, which I think audiences will find is a breath of fresh air. Issa will lean a lot more on Molly, and they’re really comfortably secure in their friendship I would say.”

Insecure returns Sunday, August 12, on HBO.