How I Became an HBO Executive Producer by Age 30
“It felt like a massive leap to go from being an assistant to being a producer, but at the same time, I felt like the work I had already been doing for Mark had prepared me for it.”
When Sydney Fleischmann isn’t in quarantine baking banana bread and focaccia, she’s busy executive producing the hit anthology series Room 104, created by The Duplass Brothers, Mark and Jay Duplass. Fleischmann’s parents pinpoint dressing as Steven Spielberg with a face paint beard, baseball hat, and giant video camera slung over her shoulder for her third grade book project as the moment she knew she wanted to be a producer. After studying Film and Television at Boston University, Fleischmann spent a summer in Cape Cod working at a candy store and working on a small indie movie before moving to Los Angeles to pursue a full-time career in entertainment.
Flash forward eight years: 30-year-old Fleischmann is getting ready for the fourth and final season of Room 104, which kicked off July 24. Below, Fleischmann shares her Hollywood journey and how she managed to become an Executive Producer on an HBO series at a young age.
When I moved out to L.A., my first job was as an assistant at a talent management company. It was a great experience and all the people were awesome, but I realized pretty quickly that management wasn’t the right fit for me. I took this wild, wild risk where I said to them, “I want to work in production. Do you know anybody?” I don’t consider myself a really ballsy person, but as a 20-something-year-old, I feel like it was a really ballsy thing to say, “This isn’t right for me.” I thought I was going to offend them, but I felt like I needed to do it, and they were so gracious and willing to help put me on my right path. I should give my younger self more credit!
They said, “Well, who do you like?” I said, “I love the Duplass Brothers. I think the stuff they’re doing is really cool.” They knew the Duplass Brothers and Mark happened to be looking for an assistant right at that moment. So they reached out on my behalf and Mark and I met up for a cup of coffee. I don’t think he would ever call it an interview, it was more of a casual hang. I vividly remember him taking out his laptop and showing me a massive spreadsheet of all of the projects and ideas they had floating around. Even in that first meeting, Mark talked about wanting an assistant who he could mentor and teach how to produce and budget for the smaller movies they were doing.
I worked on Togetherness as Mark’s assistant while also producing a couple of projects during that time. Being his assistant was a very eye-opening experience — it wasn’t just about grabbing coffee. I quickly learned that being an assistant in television is essentially working as a producer for your boss. I learned so much about balancing tasks, time management, all sorts of logistics, and how to create and nurture relationships. Because that’s all any of this is: how you communicate with other people.
I remember sitting at my desk in the Togetherness post production office one afternoon when Mark came up to me and asked, “Do you want to produce this TV show?” It was Room 104, an idea he and Jay had been discussing for years, but had never found the right time to dive into. It finally seemed like the right time, and apparently Mark felt I was ready to take on a bigger producing role. It felt like a massive leap to go from being an assistant to being a producer, but at the same time, I felt like the work I had already been doing for Mark had prepared me for it.
Mark and Jay practice the “available material” school of filmmaking. For The Puffy Chair, they had a van because Mark was in a band. They had these two identical armchairs. And they created a story around what they had available to them. Working within those confines, anything can happen, anything goes. The idea was to apply those same principles to Room 104, treating each episode as a short film set entirely in one motel room. This allowed us to bring in new people for each episode that we’d been wanting to work with as guest stars, writers, and directors. It was a concept that could have been so limiting, but was actually incredibly freeing.
Producing Room 104 has given me an opportunity to play with different genres and develop stories in different ways, because we don’t want any two episodes to feel the same. In order to do that, we have to be constantly pushing our boundaries. We have to bring new people in and encourage them to push their boundaries. I have learned so much from the spirit of experimentation this created on set, especially on the development side. Creating these standalone stories taught me invaluable lessons about how to tell stories.
As I grew and evolved as a person, my role did too. While I started out as a creative producer, I was also managing a lot of the logistical production in the early days of the show. Over the course of the series, my creative responsibilities have continued to grow, and I see myself more as a creative producer and partner to the writers and directors in a way I didn’t fully understand I could be in the beginning. That’s been a really big lesson for me: to learn how to support the other creative people, how to support the crew and how to create an environment where creativity flourishes.
I also learned how to delegate tasks in a way that wasn’t possible as an assistant. So much of the job of an assistant is just doing whatever needs to be done, whatever it is. It took me at least a season on Room 104 to realize that I could simultaneously free up my own bandwidth to focus on the creative and give someone else the chance to be involved and hone their production skills. Between seasons 1 and 2, I really transitioned from being in the office a lot of the time to being at video village with directors most of the time.
Trying on different things taught me how to be the best creative producer. From my experience and from what I’ve seen, it’s a unique show in that it has a showrunner, but also kind of doesn’t. Mark and I really share a lot of that, the creative center of the show. Showrunning is managing the different stories and making sure that it all feels cohesive and, because they’re all so different, how do we find that balance?
In the role that I have played, I’ve gotten to be that showrunner, but also be the creative producer trying to solve those creative and logistical problems. Being on set all day every day, instead of being in a writers’ room where a lot of showrunners end up being, I got to be the eyes on the ground for the whole process and I feel so fortunate to have that experience, to be in the thick of it the whole time.
I started working on the show when I was so young. I know I’m still young now and I still have a lot of room to grow. But in the beginning, everything was so new and, as I’ve evolved, I’ve been able to see the show in a different light. It’s been my entire world for the last four years. It’s just so connected to how I’ve grown as a person, how I’ve changed, the new things I’ve learned and the new people I’ve met. Seeing that parallel is very special for me.
For so long I let my youth be such a big part of my identity and I felt simultaneously self-conscious and proud of being a young producer. I think I’m now reaching a point where my age does not dictate who I am and what I’m capable of, and working on the show has definitely taught me that. People say age is just a number and it sounds so cliche. But it really does feel like anything can happen at any age.
