Meet Matt Pittroff | Director & Working Stiff Films Production Company Founder

We had the good fortune of connecting with Matt Pittroff and we’ve shared our conversation below.

Hi Matt, what was your thought process behind starting your own business?

Ignorance was bliss, and in some ways still is. I am not a business person. I am a filmmaker, who happens to own a business. I started my first company by default. I knew I wanted to use film as a storytelling medium and understood no one would hire me without a reel. I also knew I needed a furnace to fuel the fire. The furnace being the business (I enjoy random nonsensical metaphors). I launched a client-direct model production company, which is a euphemism for saying I was a barback and I went to my then-boss and convinced him to invest his media money differently, allowing me to make him a TV commercial instead of running ads in the paper. That led to a customer at said bar wanting a commercial for his contracting company, which naturally led to a campaign for the Red Cross, and so the journey began. With lots of personal and professional support, I was able to generate quite a bit of heat in that aforementioned furnace, carving out a nice comedic niche for myself. Content was not king at the time, so there was no real-long term strategic plan, and I never pictured myself being able to do what I love for 20+ years. Remember, I am not a businessman. But business, like life, often comes full circle and while I am far from diapers and a soft food diet, I have had the opportunity to dive back into the client-direct line of work after many years of agency interfacing, and I gotta say, I LOVE it! The client-direct work requires mutual all-inness, and I love the creativity and communication it yields. More of this, please. And more Agency work, please. It’s chilly this time of year, we need to crank up that furnace!

Let’s talk shop. Tell us more about your career, what can you share with our community? Do you have a budget? How do you think about your personal finances and how do you make lifestyle and spending decisions?

Business budgets and personal finances are always a bit of a moving target. Seems like the constant in-fluxness may be the only thing we can all agree on these days, be it recession or pandemic-based. There’s a need for flexibility. I flex by being personally frugal, keeping the ebbs top of mind, even when flowing. I don’t need or want much, which makes for a pretty simple lifestyle (sans my two very expensive offspring). As for non-personal spending, it will always be my business model to maintain the tools we need as a production company. And a tool of utmost importance to me are the folks I surround myself with. I hire locally, regardless of where we shoot. These crew members are the smallest of small businesses. I love supporting their entrepreneurship, and take a great deal of pride in being part of local economies. There are talented artists and technicians everywhere. Sometimes you just have to work a little harder to find them. This may not entirely answer the question, and appear as an oversimplification, but math has never been not my strong suit. Doing the right thing guides my decisions, spending or otherwise.

Risk taking: how do you think about risk, what role has taking risks played in your life/career?

Risk is a reciprocal requirement to my line of work. Every new opportunity is a result of the hard work of my team proving to clients that I am the best candidate for the job. I recognize that if someone is willing to take a risk on me, I need to both avoid risks on their behalf, while remaining open to taking risks – a real conundrum, best served by a heavy dose of preparedness. If you are prepared to jump off the cliff, you have a far better chance of not busting your ass on the rocks below. See where I’m going with this non-risk-averseness? I am willing to take the jump, by pushing creative limits and that requires highly strategic decision making, which doesn’t seem synonymous with the word risk BUT every decision throughout the production process has the ability to either water down a spot (make it “safer” and arguably often less effective) or to spice up the story. I think the industry’s grown fearful of risk. Everything has to be quantified. And I think that hints at a bit of brokenness I hope to rectify, one risk at a time. Directors should have the ability to make complex decisions, quickly. We’ve often been hired for our instincts and advanced problem solving. Why not let us get back to the risky business?

Where are you from and how did your background and upbringing impact who you are today?

I am from Charm City, The City That Reads, Small-timore, The Land Of Pleasant Living, The Greatest City in America…The City with a Million Nicknames apparently. It’s got an honest, blue collar vibe and great artistic community, a bedrock of music, art, film and food. And while I work all over the country, Baltimore afforded me a comfortable lifestyle and environment to raise my kids. My dad barely finished high school, and after serving in the Navy, became a paint salesman. He worked his way up from the bottom, as did my mother in real estate. That kind of work ethic was instilled in my brother and me from a young age. They were both incredibly creative in the way they approached their jobs and taught me the value of building relationships and maximizing the effort of colleagues by empowering them to make their own decisions. Luckily this translates well to the film community at large. Honestly, I feel at home anywhere I shoot, because of the instant camaraderie and shared values of my fellow filmmaking entrepreneurs.

What is the most important factor behind your success / the success of your brand?

The single most important factor is having a sense of humor. Life and business are too scary without humor. But hard work, the desire to evolve, timing, and a little luck play into the “success” of the brand. There are a ton of really talented people in the world, so you can’t rely on that alone. Buyers want new and fresh so client retention can be somewhat inconsistent. I pride myself on not only delivering fresh creative solutioning, but a seamless experience for my clients, too, because one is no good without the other. The seamless process portion comes from years of doing it. But the fresh creative solutions require a delicate balance between tapping into the seasoned-self and the student-for-life self. It’s a full time job on top of a full time job + running a business; requiring serious perseverance, which now that I’m thinking about it, summarizes all those factors. So like I said, perseverance is the most important factor behind the success of Working Stiff Films / Matt Pittroff…and humor.

What value or principle matters most to you? Why?

I’ve got a few of them. Let’s keep them and their why brief: 

Work Hard. Give every situation your full potential, especially as a listener.

Be Kind. Nothing is worth doing if you can’t do it kindly.

Laugh. You’ll live longer…if you’re into that.

Work life balance: how has your balance changed over time? How do you think about the balance?

If you were to assess my “work-life balance,” my results would be trash. But my “work-life harmony” analytics would be an off the charts success. This is sorta another metaphor for how data can ill-inform creativity. I’m focused on work, it’s what I love and I am able to weave it into the rest of my life. My family may disagree, but LA jobs mean brunches with my son. Baltimore shoots mean my partner steals the Pre-Pro dinner show. If this isn’t what you intended with the question, here’s an alternative consideration: time and experience have minimized the gravity of each and every decision, so by proxy I am more balanced and I’ll take that.

What’s the end goal? Where do you want to be professionally by the end of your career?

I love making ads. I love the pace, the energy, the variety, and so on. My career goal is to be able to keep making ads until I am ready to hang it up. After that, I’d love to mentor and inspire the next generation to wave their independent entrepreneurial freak flags. There are so many opportunities in the film and advertising business to be creatively expressive while making a living. As a person who absolutely needs creative outlets, having a career as a commercial artist continues to be a godsend. I get to make a living doing what feels good to my soul. And speaking of what feels good to my soul/career ends: Baja fish tacos. Running a super-chill surfside food truck is definitely in my future’s future.

Website: https://www.workingstifffilms.com/

Instagram: https://www.instagram.com/workingstiff_films/

Linkedin: https://www.linkedin.com/in/matt-pittroff-3a34874/

Facebook: https://www.facebook.com/workingstifffilms