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How To Break Into Hollywood By David DeGrow Shotwell


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May 27, 2014 0 comments
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We started writing another post before this on how to break into Hollywood, and go from aspiring writer to paid screenwriter, but then thought “Why not ask screenwriter David DeGrow Shotwell?

Former professional poker player, David, co-wrote the great indie-comedy “Love & Air Sex”The movie centers on two couples, recently broken up, who navigate the question of whether to be single or get back together over the course of one weekend in Austin.

In this interview, David reveals how he learned to write and how he went from newbie writer to the co-writer of a Hollywood movie in just 6 years. Plus much more inspiring stuff for the aspiring screenwriter. Enjoy! 

So, how long were you writing before “Love & Air Sex?” and what inspired you to start? 

I have been writing for six years. In early 2008, I had no formal writing training, and no writing samples, save for a spec script of The Office. 

I lived in Las Vegas, where I had been a professional poker player for the previous five years. The money was great… but I found the work soul-crushing. I longed for more. 

And it was actually a blog that inspired me. Jenna Fischer had written a blog on MySpace regarding what it took to be an actress, and I basically substituted the word “writer” for “actress” and off I went. 

I packed up a U-Haul, found a roommate and got a place in LA. It was the most important step I took on my journey to actually becoming a writer. I didn’t just talk about it, or dream about it or work on samples… I just did it.

Did you always write comedy, or another genre?

Up to that point I had always been a bit of a comedy guy. In the sitcom of life I was the wacky neighbor. I used to wonder if I could be funny on a world stage, but I also knew I was too introverted to do it in front of the camera. 

Did you have a game plan on how to break into Hollywood once you got to LA? 

I began to think about my favorite television comedies, as well as my least favorite ones. I noticed how many different writers there were in the credits of the episodes. Each episode seemed to have a different writer, yet the voices of the characters remained the same. I wondered about that.  

So I did research. I went on the Internet. Watched videos. Learned about writer’s rooms. I was fascinated. So I thought about how I could get in those rooms, and the basic advice I found was to write a spec TV script.  My favorite show at the time was The Office, so I wrote one. 

With no training and minimal information on formatting, I simply bought Final Draft and let the voices in my head do the rest. I submitted it to the Austin Film Festival, where it was immediately rejected and decided I had to do better if I wanted to learn how to break into Hollywood. 

And how did you actually learn how to write?

Obviously, funny wasn’t going to cut it. I had to learn more. As I bought books, read blogs, etc. I learned that what I lacked was structure. As a perfectionist, I kept that rejection letter from AFF and used it as a motivational tool.

All in all, I suppose I learned to write in the same way I learned to play poker:  Reading, interaction with those who do it regularly, and simply playing/writing as much as I could.  

In neither case did I have a mentor. I suppose my mentor was a perfectionist’s drive. For example, the first game of poker I ever played was in college with my six roommates after watching Rounders.  

My roommates laughed at me. They literally laughed at how bad I was. I don’t like feeling like that.  I like feeling like I can master anything. It gives me personal pride.  

That night I was online researching poker tips and bought a few books. By the end of the semester I had won a couple of online tournaments, bought ten more books and was a regular in the (admittedly low-stakes) highest stakes game at the local casino.  

The next year, I quit working. After I graduated, I rolled up my stake and took it to Vegas, a la Mike McD in Rounders. I suppose it’s fitting that I used the protagonist’s story from a film to inspire my own.  

From there, I learned to make a good amount of money for a single guy in his mid-twenties, but by then the allure was gone. I didn’t have to work, but I had no passion. No focus in life. Was this all there was? It was then that I started my cycle over and decided to become a writer.  

How did you actually go about making that break into Hollywood? 

Once I got to LA I was fortunate enough to use my poker money to live for about four months while I got settled. Most people don’t have that luxury.  And I used this advantage to the fullest.  

I applied all over town to be an unpaid Intern and only one company called me back, (it turns out “poker player” doesn’t exactly fill out a resume) The Montecito Picture Company.  

I came in and was interviewed, mostly out of the morbid curiosity of the assistants who wanted to see what my deal was. We talked movies in the interview and they brought me in one day a week as a Script Reader, where I wrote coverage on submitted screenplays.  

This was huge for me as a writer, because I was able to read what comedy specs were going out from represented writers. I remember being aghast at the lack of actual humor in the scripts. After about three weeks, the company liked my coverage enough to hire me on full-time to write coverage for them.  

And after about six months of that, I found a job as a Director’s Assistant.  That was my film school. Twelve hour days doing everything from Creative Executive duties all the way down to making him salads, I learned all the ins and outs of the industry.  

I made a lot of my contacts and worked on a TV pilot with him… where I discovered I wanted to focus my attention on film, giving me a new path.

What was your first paid writing assignment? 

My first paid writing gig was for a script called “Some Girls”. It was the first project I was paid to write, rather than being paid after it “sold.” This only happened last year, and I am attached to co-direct it with the lead actress.  We just shot a sizzle reel for it in Austin, TX and are now completing a director’s vision book before going to cast.

How many scripts have you written? 

Let’s see… well I have only written two scripts on my own. The first was called “Destination Suicide” and it was used as a sample when I got the job to write “Some Girls.”  

Before that, everything I wrote was done with my former writing partner.  He was one of my first friends in LA, is an immensely talented actor and writer and we remain close, albeit from across the country.  

How did you get involved in “Love & Air Sex”?  

So around 2009, while I was a Director’s Assistant, Steve Walters sent me a script he had written. I honestly don’t recall the name right now. “Forever Is Over,” maybe? Anyway, I loved it and gave him my thoughts. Then we met up a few times to discuss it. Then we discussed some of my goals and ideas. 

Up to that point, I still wanted to focus on television, so I talked about that.  Eventually, we decided it might be nice to be TV writing partners, as we had similar sensibilities. So we set off together. We wrote a comedy pilot called “Cincinnati International” that we loved. Oddly enough, the only meeting we had on it was at Jennifer Love Hewitt’s production company, where they suggested it be a cartoon.  

So, that was interesting… We followed that up with an hour-long drama pilot called “Guardians.” This was a huge mistake because we were attempting to identify ourselves in the market place and we basically followed a “Brooklyn Nine Nine”—like script with one that read like a Tarantino film.  

We crammed too much into those sixty pages rather than letting the concept breathe. It had a few fans, but it was simply the wrong choice for TV. You can do that kind of thing in Independent film, but TV likes a “brand.” 

At this point, we were looking for representation together, but wanted a third sample. Over the previous year I had given Steve extensive notes on what eventually became “Love & Air Sex” and he suggested just adding my name to it and using it as our last sample, but this made me uncomfortable.  

I asked for permission to do a pass on it, with the understanding that it was his baby and if he didn’t like it, we’d just scrap the changes and move on.  He agreed. I did a pass that wasn’t too extensive and he was happy. He gave me some notes on my changes and made some more of his own.

After that, a friend got us a meeting at a pretty big agency. One of the agents loved the script. She wanted to take it out to select production companies and see if she could get anyone to pair with us. I believe at this point we had changed the title of the script to “The Rebound.”  

We met with three companies who all pitched us on why we should attach them, however, one of the production companies offered to match up to ten million dollars from a studio. HOLY FUCKING SHIT. We had done it. We had ten million dollars on the hook!!!  

We went out and pitched with them. We went to small studios, who all either passed or had terrible notes, causing our production company to pass. We were down to our last studio… but it was the big one. And the one who was most interested.  

We went to this studio and met with the Vice President of Production, the very same one who I had tried to schedule a meeting with my boss — the director — the year before and had been turned down.  

I have never been so happy/excited/nervous. By the end of the meeting, the gist was this… he loved that script.  Wanted to work with us, but thought this was more of an Indie, and let us down with the old, “It’s not you, it’s me.”  

He said that his studio would ruin a script with great heart by making it a soul-crushing wedding movie or the like. We were devastated, but we all put on brave faces as Steve and I hugged the Production Company executives goodbye in the lobby.  

They told us we’d set up more meetings soon. We never heard from them again. And the VP who wanted to work with us? Same thing. Welcome to Hollywood.

So, that was it? The project died? 

Yep, pretty much. In the meantime, Steve moved out of state, back to his hometown and we never recovered our momentum. But we forge ahead, as Steve and I pump out two spec comedies by each writing one and then exchanging them for rewrites, etc. etc.  

We gave them to our agent. She never said she didn’t like them… but she had a lot of notes. Our groove had been impeded and we both knew it. It was then that fate intervened… 

In desperation after losing our TEN MILLION FUCKING DOLLAR INVESTMENT IN OUR TWENTY FUCKING MILLION DOLLAR MOVIE THAT WOULD MAKE US RICH AND FAMOUS I submitted our script to ScriptShadow, the script review site.  

They had an amateur week for repped screenwriters — their first one — and chose our script. They saved it for the end of the week and gave it their highest grade.

A producer reached out to Steve and I for a meeting. They wanted to make our movie for around a million bucks, a far cry from where we were, but in Hollywood — unlike the world of Romero — NOTHING comes back from the dead.  

It took three years of notes, rewrites, casting, etc. but we made the film. Bryan Poyser, who directed the film, came on as a writer with Steve and I, as he wanted to put the script in his voice.  

We changed the title one penultimate time to The Bounceback and shot the thing. It was like camp. The best experience of my life, and I never expect to have an onset experience like that again.  

We debuted at South by Southwest before starting the rest of the Indie festival circuit. At the end of the day, the film was bought by Tribeca for distribution, under the caveat it could change the title one final time… to “Love & Air Sex.” We agreed, and the film is available now On Demand, etc. Phewf. That’s it. That’s how I got involved in the longest story of (fortunate) development Hell ever told.

What’s your writing process? How many hours a day do you write etc.? 

My writing process is unique. I don’t write a certain number of hours or days a week. Instead, I tend to go through streaks. When I’m working on a project, I tend to become all encompassed by it. I find myself not wanting to do anything else, so when I’m not developing something or writing, I like to take long breaks and immerse into my life.  

Whenever I write it is at home, though. It’s usually from about two hours after I wake up, until about two hours before bed, giving me just enough time to run errands for my day and then unwind.  

As far as my actual process… I have a list of around forty two steps that I follow for each draft.  I say “around” forty two because it is ever-evolving.  One thing I firmly believe is that we should always be learning, looking to improve. So I spend a lot of my free time watching classic films, foreign films and reading books. It’s from those experiences that I change my list of steps.

What are you working on now? 

My situation now is totally and completely focused on “Some Girls.” I had a pitch a couple of weeks ago to write a Road Trip comedy, and would love to do it if they go in my direction, but right now I’m learning the ins and outs of another type of story telling: direction.  

I think it’s important as a storyteller to be as knowledgeable as possible, so that’s where my current situation lies, both creatively and monetarily.

I am not the type of person who says “Live with No Regrets,” if anything, I’m quite the opposite; I regret everything. But in terms of writing, I really have none. 

I had to learn that I didn’t want to do TV, before I learned I wanted to do Independent film rather than studio film, before I learned I wanted full control and needed to learn to direct. I had to learn to write with someone before I learned to be self-sufficient.  

The only thing I regret is not getting into film earlier. I wish I would’ve majored in film in college, gone to film school, etc. But even with that, I feel like I spent an inordinate amount of my twenties being grounded outside of film and learning who I was before I tried to express that. That’s pretty great, too.

Do you have any advice for new writers on how to break into Hollywood? 

The only advice I have to new writers on how to break into Hollywood is this… and it’s the most important advice of all: Move to Los Angeles. Now. Not later. Not once you save more money. Not New York. Not Chicago. Not after you get more samples done. Move to LA. Move to LA and be poor. 

Don’t come and take a job that pays you $1000 a week. First of all, it won’t allow you enough time to write. You should work enough to make exactly enough money to get by, that’s it. No more, no less. 

I could argue it’s even important for your artistic voice to struggle financially for a bit. It’s miserable, but you’ll get through it, either as a writer or someone who knows it’s not for them. You’ll get through it. And either way… you’ll know. You won’t have to spend your life wondering “What if?”  Move to Los Angeles. Move to Los Angeles and be poor. Your characters will thank you.

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