Filmmaker Dennis Williams II On Exploring Stories of Black Entrepreneurship

Dennis Williams II is a storyteller. With his upcoming series, Payroll, a primetime, half-hour serious comedy about a group of three young, black men from New York City, who quit everything to start the largest music and tech festival that the culture has ever seen. He's looking to expand the notions of black entrepreneurship and solidify the importance of committing to your dreams. Below we discussed his earlier films, his very first day on the Payroll set, and his responsibilities as a storyteller.

Growing up were there any factors that influenced or helped you on the path that you’re on now?

Growing up in the early beginnings of the digital era really helped me unquestionably. I honestly think millennials have the biggest advantage just because as we mature, technology matures. It’s not like we were boomers and we were kind of set in our ways when tech became a big part of everyday life. So you’ve got to think about it as our generation having early access — which is a gift and a curse at times.

I remember having Limewire and being able to download my first Christopher Nolan movie at 13. Platforms such as MySpace allowed you to engage with people all over the world. I believe technology really opened those doors for me as a storyteller. As I started to learn more, I would just dig deeper into the Internet. I bought my first computer with my snow shoveling money and that opened the road of discovery for me. At 15 I got my hands on this really new age camera at the time, called the Digital Blue, and I remember making basketball workout videos with my best friend, Ben. I was really fascinated about how one could go record something and cut it up and make it look super cool. In hindsight, growing up I was ambitious and curious about what the world had to offer,  which pushed me to explore different avenues towards becoming a creator myself.

Earlier you were talking about storytelling and how you started venturing into video with the Digital Blue Camera. From further research on you, the term “storyteller” is associated heavily with your name. What do you believe are the responsibilities of storytellers in our generation?

I think the most important responsibility is to write what you know. And not just write, but create what you know, because there are so many people out here trying to create other stories. And if you bring your true authentic story to the world, whatever that may be, however that manifests, I think that’s what pushes the culture forward.

Everyone needs to come to the table with their true authentic self and to put that to paper, on screen, or onto a canvas as an artist. It wasn’t until I understood this that things started clicking.

Did you have an “aha” moment in a sense when you realized your authentic self?

I think it was a very long journey after many, many no’s and doors slammed in my face. I hate the theory of the 10,000 hour rule but I think the “aha” moment comes after those constant hours and hours and hours. Having that gut feeling that something you did years ago is going to pay off one day. Some ideas that you dream about super early on are going to shock you and get you out of your seat to scream, “this is the one,” but some of them you just believe in and though there may be so many odds against it, if you’re able to pull it off the rewards are bountiful.

My first short film Note To Self was that idea. It was a story that was really down to earth, told through people of color by people of color. With filmmaking, you may think that the script is done when you export the pdf or hand the script to the actors, but that’s not the case. We had to make so many split-second decisions on set. The last scene that we shot for Note to Self was, in a lot of ways, improvised, but the actors understood what their narrative was. With the crew being 15 hours into heavy production, it was unexpected, but I knew what we shot was what we needed. In every way, that’s an “aha” moment in itself.

Did you have a prior background in filmmaking or were you self-taught?

I actually studied screenwriting for three years in college. My minor in college was theater and we read a lot of Shakespeare plays backwards to learn triggers and heaps, the building of a character, the building of a environment, etc. In all of that I found my love for storytelling. My theater teacher was a playwright who told me getting into filmmaking definitely takes a lot. I wanted to win at it and I really fell in love with the notion of story.

I think that’s just kind of what pushed me that way. I went to the University of Dayton for a two and a half years and then I graduated from UMBC in Maryland. UMBC had this camera program where you could use your library card and rent a DSLR for days at a time. In my mind I’m like, wow, this is ridiculous! So, I began renting the camera every two days, dropping it off for a couple of hours, and getting it back same day. I did that for months and months and that’s when I learned what I really wanted to do as a filmmaker.

“… if you bring your true authentic story to the world, whatever that may be, however that manifests, I think that’s what pushes the culture forward.”

What stories are you looking to tell or projects that you’re interested in exploring?

I’m looking to tell the stories of black entrepreneurship. Exploring the notion of really building your own, obtaining success in a professional and creative way. I know it’s a story that’s not out there right now. So, that’s what I’m looking to do, hence, why we have Payroll. All of my previous stories definitely delve into how the media has played on communities and things like that. It’s important for me to tell stories that are impactful to me and stories that are going to matter in the grand scheme of things.

What were the early foundations of Payroll?

I was working in San Francisco at the time for tech company and my film Note to Self was in the midst of its festival run and I really wanted to work on a TV show. The majority of the stories in Payroll are parts of my journey, whether it be professionally or personally. There were a lot of ways that this was going to roll out and it wasn’t going to be Payroll at first.  I can’t tell you that from the beginning it was about three friends from Brooklyn who put on a music and tech festival. There were so many ways it could have manifested, but I knew the narrative I wanted to tell, which is about building your own dream with people that you struggled with; that was the most important factor to me.

It took me a month to write the first draft of Payroll and another 8 months for my team to assemble the cast and crew to shoot the pilot. Currently we’re now past post-production and really shopping the pilot into the market. Being super ambitious, I wanted to shoot it as a full hour. As a new creator I’m thinking I can pull this off. I knew I wanted to shoot it and for it to go directly to the network. In August, Note To Self wrapped up its festival run at the HollyShorts Film festival in LA and I was having a lot of conversations around what projects I had in the works. We had Payroll, but no actors committed, no nothing. All we had was a script that I thought was worthy. However, we knew that every potential actor would have to have a following of their own for us to pull this off.

Payroll is a primetime, half-hour serious comedy about a group of three young, black men from New York City, who quit everything to start the largest music and tech festival that the culture has ever seen. But they quickly learn a harsh reality: Business isn’t done by the book, and any wrong move can cost them the future they’ve bet everything on.

My two producers, Jesse Martin and Jared Adkins, who are also my partners in Campsight Studios, held auditions in New York City for the next two months. What we found was that all of our supporting characters had very strong resumes but we didn’t have lead actors that we thought could perform at the level we wanted to reach. We were pretty ambitious (lol). My goal was for Payroll to be on Starz or Netflix in that arena and for us to partner with someone that would allow us creative control. The stakes were high so I knew we had to do it right up front. Still, on the search for lead actors, we leveraged the power of social media and went to Instagram.

The first actor we reached out to was J Mallory Mcree – he has been on the shows in the likes of Homeland, Quantico, and Marvel’s Luke Cage. We flew out to LA to have a meeting with him and he really wanted to produce on this, as well, and to help the show reach his network rooted in LA. He’s represented by Untitled, which is a pretty reputable management firm, and he was the first actor to come on board.He auditioned for the role of Dom, but he was the perfect fit for Cam, without a question in my mind. In the show, Cam is the first generation true African American male, who’s getting his master’s in school and comes from a very prestigious family that is very structured in their ways, and he takes this leap to join Dom (who’s much more of the risk taker) in his journey of putting on BandoFest.

So, J Mallory really fit Cam. We tell J we would love to have him on board. On our trip back from California we get a response from another DM that we sent out. Jared had reached out to Trav Que, who plays Jaxon in the show. Jaxon is the inner city New Yorker who is torn between the notions of separating himself from his past way of life and/or committing to their future.

Trav Que auditioned for us twice. The first day that he came in, he auditioned without a script, which spoke to how seriously he approached his craft. We were blown away by his audition; he was a perfect fit for Jaxon. As the filming kept getting pushed back, he was still down for it. I think that spoke a lot to his commitment and Trav Que is an excellent actor.

Ironically, the lead character was the one that came last and originally he wasn’t Brandon Wellington. Just a few weeks before we were about to film, Ser’Darius Blain – playing our lead character, Dom – he had to be pulled out due to his intense schedule with the Jumanji reboot. Instead he asked us to consider his best friend, Brandon Wellington, who is an Emmy Award-winning spoken word artist. He has really, really worked his ass off when it comes to acting on screen and he was a perfect fit for Dom. In Payroll, Dom is the in-between of Cam and Jaxon. He comes from humble beginnings, now wasting away in corporate America until he finally decides to take a risk on himself and build something of his own.

Artist, TravQue as Jaxon, Actor, Branden Wellington as Dom, and Actor, J Mallory as Cam.

Could you describe the moment when you’re walking onto set the very first day, you have all three lead actors, your full crew & cast, and you’re like, okay, it’s time for us to do it. How were you feeling?

Well, I hadn’t slept much the week before the shoot date so you would think we are running on fumes. Stefon Bristol (my co-director) and I were scouting locations a few weeks before our planned shoot date, I’m editing the script to make sure that we’re really covering all our bases, etc. The biggest thing I learned really early on is that there’s a story that you write, a story that you shoot, and then the story that you cut in post production. Your job is to make it as close to what you had written and imagined in the beginning. We had a few difficult moments when it came to shooting and I was just trying to make sure that we got everything that we came for, given our 10 months of hard work. On the ride to the warehouse scene, our first set of the production, I had my Beats on, focused, and I vividly remember going over the camera plot list and checking my bases in detail.

The first thing we do once we arrive is our safety meeting since we’re in this huge unfinished warehouse. After we closed the safety meeting, it was time to go and everyone was running to their areas and really focused on their agenda. I stopped for a brief second and simply told myself, “Ok,” because after this moment there’s no going back! As we began to shoot more scenes, across different locations, things became easier for everyone, as it is for every quality production team.

“I know that I am getting much closer to breaking down these barriers and being able to put this content out on a large scale. You know good can be debated, but greatness cannot be denied and I think as we continue to get closer to that, that’s just igniting the agenda.”

Out of Dom, Jaxon, and Cam, Which character do you identify with the most?

Dom for sure. As I told you earlier, Dom is the character that came from a less than glorious background, that is a breadwinner in his family and fought to get into corporate America. As much as he succeeds there, it doesn’t mean anything if you can’t win with your friends. That’s truly how I feel. Dom takes the leap to go bet on themselves by bringing Bandofest to fruition. It’s not gonna be an easy journey and that’s what I found in my own journey. It’s this really interesting dynamic because a lot of those environments I’m in day to day right now are completely different than what I grew up in. So, I really found myself in Dom and he’s going to go through a lot of troubles that I went through, but he’ll have a lot more foresight and courage going through it. The question is, will they win in the end?

When you get green-lighted for your season, what topics are you looking to explore?

We’re looking to explore matters like imposter syndrome. That’s a big one for me. Mental health in the millennial community is big; mental health in the black community is just as important, too. Also, the feeling of whether you belong or not day-to day is something that I think a lot of us in this space have to explore. The effects of corporate America I plan on touching on. The role of social media and building a business in the digital age.

Lastly, camaraderie is another theme that I think is huge and you’ll see that played out in Payroll scene to scene and as these characters go up and down on their own journeys. They’re going to have to make their own decisions for the greater goal of the team.

What is going to be the tone of Payroll? In one of our previous conversations, you stated how “Atlanta on FX” and “How To Make It In America on HBO” were previous inspirations far as tone. Is Payroll going to be similar?

I think it’s fair to say that Payroll has the tone and the ensemble of Atlanta, but the environment and the depths as How To Make It In America, with those two worlds colliding in Brooklyn. By us using Payroll as a vehicle for telling the story of building your own creative space, is a lot like HTMIA. On the other side, the cinematography, the comedy in it, and the stories that are being touched upon are much closer to the urban community and I want the story to feel that way. A lot of it feels like Donald Glover’s work per se. So I think it’s a merge of those two worlds.

When it’s finally finished, and the audience’s are watching Payroll, what do you hope they take away from it?

The number one takeaway is to commit to the dream. Committing to whatever that is destined for you. If you’re giving 60%, 70%, 80%, you’re not going to be able to see the light at the end of the tunnel. Constantly staying persistent and staying resilient. The goal for me is to get us to feel like we’re going along the journey with them and we’re carrying that weight as well. There’s a lot of comedy in it but also a balanced mix of struggle as well. We’re making sure that you feel like you belong with these three characters as they try to make their festival come to life, episode to episode. The idea of committing to the dream is the primary lesson that I think audiences should to take away from this.

What is the hardest lesson that took you the longest to learn?

Definitely having patience.

What excites you about the future?

I’m excited to tell more stories and to see other stories being told. I’m excited to keep building and I’m getting better at my craft. I know that I am getting much closer to breaking down these barriers and being able to put this content out on a large scale. You know good can be debated, but greatness cannot be denied, and I think as we continue to get closer to that, that’s just igniting the agenda.

I think stories like Payroll are missing on TV right now, as I said. So, being able to see that on TV or on the big screen and being able to have those pivotal conversations about bettering yourself and pursuing a dream, particularly from a black man’s POV, will open discussions that need to be had and it represents a narrative that needs a big stage.

Lastly, what is the legacy that you hope to leave behind?

I want to leave behind a catalog of work to show that anything is possible and that you’re entitled to everything that you work for, and I want to do this through my creations. On a very large scale, I want to be one of the best filmmakers that has ever lived for the reason of telling the story of perseverance and success of the minority and the disadvantaged, in whatever way that manifests.

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