INSIDERS #3 with producer and Hallmark movie writer Joey DePaolo

The former manager's assistant shares his Hollywood journey

I’ve been waiting to share this INSIDERS interview for a while and not just because it’s so insightful but also because I’ve known Joey for a long time, and he’s just awesome.

One of the first people I met when I moved to Los Angeles who was actually working in the business, we shared a love of the career of tennis player Andy Murray and low-budget indie movies. After all this time, it’s wonderful to see just how well he’s done navigating the choppy waters of Hollywood.

Joey’s now an in-demand screenwriter and producer, and earlier this year his movie, An American in Austen, aired on the Hallmark channel. He’s been busy but there’s much more to come from Purple Crayon Entertainment, the production company he runs alongside his wife Veronica.

And while all of this sounds like a Hollywood movie in itself, he’s had to overcome many obstacles.

There’s no straight line to success in the film business and here, he talks about the lessons he learned from working as a manager’s assistant, why landing an agent is validating but not the endgame and the merits of spending some time working outside of the industry.

Today, you need grit and determination to be able to push your projects out into the world and then a lot more of the same in order to stay the course.

Joey’s seen the industry from many angles, so settle down for an INSIDERS interview that shouldn’t be missed if you want to be managing, screenwriting or producing.

Joey, thank you so much for taking the time to answer these questions so thoughtfully. I love the fact that you’ve agreed to be grilled for The TEN.

To begin, can you tell me a little bit about your early career in entertainment, including how you ended up working on the management side of the industry?

I came out of high school in central Florida, which, for an aspiring writer, could not have felt further from relevance.

I dreamed of studying at Tisch and living in the city, so I only applied to one college: NYU. In retrospect, it was a pretty stupid move and I’m lucky they didn’t tell me to kick rocks. But I knew where I wanted to be.

With no natural network and mountains of student debt, I knew I had to hit the ground running. So I spent my time in New York and my early years in LA doing whatever I could to diversify my experience.

I interned for Conan O’Brien, worked as a stagehand for Inside the Actor’s Studio, read manuscripts for Paramount, and took on a range of other gigs from script reading to interning on film sets. The goal was to build up as many relationships and as much real-life experience as I could.

When I moved to LA, it paid off. Months after I arrived, the WGA went on strike and suddenly the entire industry ground to a halt. I felt completely stranded, then one day I got a phone call. A producer I’d read scripts for knew of an assistant position opening up.

A week later, I started my first real job as a manager’s assistant for the legendary Marion Rosenberg. Marion had repped Hollywood icons like Bette Davis and Elizabeth Taylor, and produced on films like The Deer Hunter and Revolutionary Road.

My hope in working in management was to learn what was selling and why, and that’s exactly what I learned from Marion. 

What an incredible experience! But you’re also a writer, and early in your career you found representation with a top agency. Can you tell us how that came about, and how you know if an agent is right for you?

First of all, I think it’s important to point out that representation is not a starting point or a finish line. It’s an important mile marker, but your career is about what you do, both before and after you have an agent.

For me, that took years, once my work had a little more seasoning and I had partnered with a writer who was just as unhinged as I was. We wrote with every free minute we had — through the night after our day jobs and on weekends — while still finding time to grab drinks with assistants and low-level execs.

We landed reps once we’d finally built both a network to notice us and work that was worth being noticed. It needed to be both. As soon as we finished our splashy little pilot, my partner and I used these relationships to get read by some junior agents and managers, and, as fortune would have it, we ended up signing with a couple of the biggest — CAA and Anonymous Content.

Now, being repped by a fancy agency sure is validating and gets some people to finally take you seriously, but the truth is, that only gets you so far. You’re the smallest fish in your new pond, and you’ve got to prove it all over again.

Every agent has over a dozen clients, each vying for the agent’s attention. As a “baby writer”, your new fight is to earn their outgoing phone call on your behalf, and earn their selling you first when opportunity knocks.

In the end, it’s the agent, not the company, that reps you, so it’s their belief in you — that you’re a vessel for reaching their own goals — that matters. Your best asset is someone that believes you’re their meal ticket.

The last thing I’ll say about reps, as I’ve been one myself, is that they shouldn’t be responsible for your success. Not that they shouldn’t bring you opportunity. But more of it should come from you. And, if we’re being real, no one will ever be 100% motivationally aligned with you.

So if you want to get somewhere, the instincts, the networking, and ultimately, the strategy should always come from you.

In the past, you’ve had projects set up with Robert Downey, Jr. and producer Brett Ratner. Did you have to pitch to them in person?

Once our first pilot went around town, we quickly wrote another darker, more dramatic one, which gave us the chance to take meetings with a pretty wide range of studios and production companies.

We were open as to what we wanted to write, so this gave us the most opportunity to make connections as new writers. We’d sit in general meetings and discuss ideas we had, or sometimes something that the production company had tried to crack.

As new writers, we were doing all of this on spec, with the logic being that the calibre of the teams we got to work with made the investment worth it. We worked with some talented groups, and Team Downey was one of them.

That said, the dark side of development is that it takes a really long time for a project to come together, which exposes it to a bunch of variables that could sink it.

My partner and I had a number of promising projects that fell apart in a million different ways, ranging from our partners leaving the company to social movements.

My favourite was an animated TV show we developed with RatPac about ‘The Rat Pack’. We even had the blessing of the Frank Sinatra Estate to use his entire library of music, only for it to unravel when Brett Ratner was MeTooed.

That’s just how it goes sometimes. And it was a good lesson about the fragility of the work. You want to invest your time in the right places, then just as quickly, you have to be able to let it go.

How do you deal with disappointment when things have taken a sideways turn with a writing partner or a production company?

We really are crazy to pursue this stuff for a living. An old coworker used to say that we’re all playing the slot machines, praying for cherries.

You have to endure a ton of rejection to do this. You expend so much to get to a “yes,” and so for me, for my own sanity, I had to adjust my perspective.

I have so little control over a lot of business decisions that are made about my work, so I try not to fall in love with any opportunity. Now, that’s easier said than done, because in writing, your product is especially personal, and always capable of breaking your heart.

I’ve been doing this for over 20 years, and only now am I getting to a place where it lives in a healthy space for me.

While it’s not unusual for people to take breaks, why did you decide to take a hiatus from managing – and also writing – in 2020?

I’m probably not alone in saying 2020 was the most trying year of my life. But in retrospect, it offered some really unique perspective: that when the hustle and distractions are stripped away, what remains the most important thing to you?

It’s always been easy for me to get swept up in the grind, and I’ve made a lot of sacrifices for my career. But at that place in time, when I stopped and looked around, my relationship to writing wasn’t healthy. It represented way too much to me – a dream, an escape, a different life – and that’s pretty hard to sustain, and even harder to balance. Plus it wasn’t making me a happy person.

So I stepped away from writing that year and spent three years working in solar sales. For the first time, my career became a job, just a means to an end. Honestly, it was refreshing for it to only be that.

I completely let writing go. I buried it and mourned its death. And so, last year, when I had the opportunity to return to writing, I embraced it for what it was. I was no longer looking for pageantry or escape; I was looking for a job doing what I love. 

You run a production company, Purple Crayon Entertainment, with your wife Veronica, who also produces Hallmark movies. Can you describe that dynamic, and what are the challenges - and also advantages - of working so closely together?

It’s really a dream come true. Creatively, Veronica and I are lucky enough to share a story brain. We laugh at the same things, we critique the same way, we bump on the same story beats. It’s uncanny. So, in that way, we’re really lock-step in our vision of the kinds of stories we want to tell, and how we want them to feel. And that just makes everything easier. 

The process of developing with my wife is also a very funny experience for me because as a producer, she’s an absurdly straight-shooter, which gives me plenty of opportunities to get my feelings hurt over simple notes.

On the other hand, being sort of a perfectionist, our partnership means having an unlimited number of touch points with my producer, which allows us to really test the limits with everything we make.

Through the company, you sold an original film script to Hallmark; can you tell us anything about it and when we might see it on our screens?

Yes, we’re in final stages right now on a high-concept Christmas project. In the well-worn turf of Hallmark Christmas, I think it actually manages to find new territory, so we’re really excited about it.

So many screenwriters I know want to write movies for Hallmark. What’s the secret sauce?

What’s amazing is that I don’t know anyone who can’t describe exactly what a Hallmark movie feels like. That’s quite an accomplishment. They’re really successful at curating a network as a feeling, and so as a writer, it’s important to honour that when developing with them.  

That said, outside of a basic act structure, there’s no colour by numbers. Hallmark has taken some pretty big conceptual swings recently, including our last project, An American in Austen (which first aired in February), which followed a woman who wishes herself into Pride & Prejudice only to destroy it from within.

The Hallmark audience knows what it wants, but they’re always excited for a new recipe. My one rule? Write a movie that happens to air on Hallmark, not your interpretation of a ‘Hallmark’ movie. 

Are you given guidelines because their movies are very specific in what they deliver.

It’s more of a mutual understanding. Hallmark is appropriately protective of that feeling it creates, so it makes for some common sense ground rules.

As a writer, that may mean making things work without certain story devices or character types. And in that way, writing for Hallmark has been the best writer’s boot camp I could’ve ever asked for.

Building a fun, engaging romcom that they haven’t already done, in 84 minutes, without the use of imagery or language that could make a viewer blush is a unique challenge. And an incredibly fun puzzle to crack. In a lot of ways, it’s made me a better writer. 

Has your experience working in management helped you with your writing career, and if so, how?

It’s definitely given me a better understanding of the marketplace. One of the more difficult things to navigate as a writer is being so disconnected from the business side.

Often, folks try to ‘protect’ you from the truth, whether it’s sugarcoating the future of your dead project or the real reason behind a pass. There’s a language to it that could be frustrating if you don’t know where it’s coming from.

Having watched the process behind these decisions over the years, I think I’ve grown to be at peace with the fact that they’re rarely personal and sometimes just unfair. And in the event that you do want someone to tell you the truth — which I recommend — you had better be able to handle it. 

What are your future plans for writing/producing, and have you found that selling an original screenplay to Hallmark has opened doors?

I’m having a lot of fun exploring the romcom space, both in and out of Hallmark. Veronica and I were raised on the classic ‘90s romcom, and are naturally believers in its renaissance, so we’re taking time to explore that world.

Everyone is squeezed for money right now. What would you say to anyone thinking of producing their own movie?

I mean, I personally wouldn’t, but that may just be the film school PTSD talking. I don’t think there’s a wrong way to pursue your business, though I’d never recommend putting your own money into a movie. 

That said, if it’s burning a hole in your pocket, I’d suggest you instead spend it on networking. Find execs and producers to connect with, and work at it until you have someone in the low-budget space that’s in a position to buy and make things. Find out what they need and develop for those needs.

Aim for viability, and by that I mean, write something where at least two different buyers you know would produce it. Time is always your most precious commodity, so put effort into things that have a real shot. 

We all know there’s no such thing as overnight success. What’s your advice to anyone looking to have a successful career as a screenwriter in today’s world?

You can say that again! This business really knows how to keep you humble, so at the end of the day, your own instincts are your most important asset. Trust them. 

My advice is pretty simple: Write as many specs as you can. There’s been a massive amount of reorg this past year, and it’s a spec market. Be smart about what you write and who you write for, but write.

And, more broadly, don’t work in a silo. Seek out development folks whose taste you trust. Build relationships with them, collaborate with them, and, most importantly, trust their notes. Be open to criticism, be open to growing your skill and your craft.

No matter what’s on your resumé, you should always be sharpening and getting better. 

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Old Hollywood: Joey’s former boss, the agent & producer Marion Rosenberg is a contributor to the HBO Documentary Liz Taylor: The Lost Tapes, which airs on November 21, on Sky Arts.