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Embracing Entrepreneurship As a Screenwriter Part I: Taking Initiative

October 28, 2020
4 min read time

I believe that being an effective entrepreneur is hugely beneficial when it comes to being a successful screenwriter. First and foremost, it improves your overall chances and opportunities. Secondly, it reduces the number of people you need to rely on for something to “happen” (as Mark Duplass famously said during his inspiring speech at SXSW, “the cavalry isn’t coming”). And lastly, it enables you to do the one thing that the majority of us all came out to Hollywood to do: make something!

Now, please don’t get me wrong. My body shrivels with PTSD when I talk about anything having to do with “business”, as my career began in finance and accounting where my creative soul was rapidly dying (I know, that’s a little dramatic, but when you're an artist at heart and are locked away in a closet-of-a-room all day and night staring at numbers and spreadsheets, it leaves quite a lasting impression on you). But, there are a lot of useful tools that you learn in business that can be highly beneficial for creatives navigating the  Hollywood landscape.

Beginning with: taking initiative! A wonderful trait any successful entrepreneur needs to flex. This is exactly what I needed to do in order to make my first feature film, Poor Greg Drowning, which began as a short film, then evolved into a web series before it ultimately hatched into its fully realized self as a feature. And my inspiration to take that initiative was Mark’s aforementioned speech at SXSW.

When I first moved to Los Angeles, I spent the majority of my initial days networking, writing and learning how to develop my own projects (while simultaneously embracing any freelance gig I could find). Then, the universe tested me. On the exact same day, I was offered a high paying director of finance position at a new film company back in New York City, as well as a director’s assistant position on a fantastic indie feature — but for much less pay. Despite my rational brain’s incessant screaming for the financial security of the former, I quelled my creative heart’s fears and chose the latter. It was the best (and scariest) decision I ever made. Facing fear, following your heart, and embracing short term sacrifice for long term goals are all necessary steps in the life of an entrepreneur. As is buying a flask with a syringe. Just kidding.

So that’s when I began assisting three extremely talented and successful comedy writer-directors who I had been huge fans of for a long time. First, I assisted Victor Levin on his feature 5 to 7, then Luke Greenfield on Let’s Be Cops, and finally, I worked for John Hamburg for a couple of years and assisted him on his feature, Why Him?

During the first year of working with John, I watched Mark Duplass’ speech online and was immediately struck by his message; that there is no excuse not to make films on the weekends with your friends. I paused for a beat, then said to myself (most likely out loud, which most likely caused John to shake his head at me once again), “Damn it Mark, you're right!”. I had spent three years writing while assisting these amazing directors, but it had been three years since I had directed anything of my own.

So that night, I wrote a five minute short film called Glimpses of Greg. When I came up with the character, I immediately envisioned my good friend and über talented actor, Graham Sibley, in the role. I sent it his way and he was totally game. That weekend, we shot the five minute short film in two hours for $25 (the cost of a pizza for everyone). The short film was accepted into several great festivals and we were very proud of it.

But, I knew there was so much more of Greg’s story to tell. I loved the character and his potential for an engaging and hilarious emotional journey. So, over the course of a long weekend, I sat down and wrote the first draft of the feature version of Poor Greg Drowning (I don’t necessarily recommend writing that quickly, but this specific script literally just poured out of me… Embracing the whole water theme, there). The short film ultimately served as the first scene in the feature film years later (we even used the same footage that we had already shot). Now that I had a feature script, it was time to take initiative again. 

The only obstacle was (and is the same for a lot of writers), I was working full time and we didn't have money to shoot an entire feature. We forged ahead anyway, deciding to shoot the script piecemeal on the weekends whenever we could, with the initial thought of maybe just putting out episodes as a comedy web series. But how do you attract great crew and talent to work practically for free? Again, lucky we had that short film completed, which we were able to show potential collaborates as a sizzle trailer to get them excited to be a part of the project.

Then, we embarked on the filmmaking journey and over the course of a year, we shot 44 pages of the 100 page script (for very very little money). We were about to put the first episode out (which was the short film that we had shot a year prior) when I stopped and thought, how cheap could we shoot the remainder of the script for and finish it as a full feature film?

I brought on two producers who I had worked with on Why Him?, and they did a production budget and came up with an ultra low budget number to finish the movie properly. Then, using the footage we had already shot as a sample, I sent it to two potential investors. We were incredibly blessed and fortunate to have them come on board as two wonderful EPs that I am eternally grateful for. We assembled the final crew and cast, and shot the remaining 56 pages of the script over the course of six shooting days (insane… I know).  

Finally, roughly fifteen months after I saw Mark’s speech and we shot the short film, we had the feature film in the can. That was September 2016. The movie didn’t come out until August 2020. Little did I know just how much entrepreneurial spirit I was going to have to summon over the next four years to actually put a film out there.

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