Derek Pfister of County on Life, Lessons & Legacy

We recently had the chance to connect with Derek Pfister and have shared our conversation below.

Hi Derek, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: Who are you learning from right now?
As a creative, I’m constantly learning. Every project and every person I work with teaches me something new. Filmmaking is one of those crafts where you can never truly know it all, there’s always more to explore. Whether it’s discovering a new lighting technique or experimenting with a lens on a cinema camera, there’s always an opportunity to grow and refine your approach. That’s one of the things I love most about what I do, it’s a lifelong journey of learning, and I’m proud to be a student of the art for as long as I live.

Can you briefly introduce yourself and share what makes you or your brand unique?
At my core, I’m a storyteller, a creative driven by the art of filmmaking and visual storytelling. Over the years, I’ve worked as a Cinematographer, Director, Producer, and Editor across a wide range of projects, but my true passion has always been capturing stories through the lens of a camera.

I’m the founder of Chair on Stair Films, a video production company based in the Midwest that specializes in cinematic storytelling for businesses, weddings, and creative clients. With over 20 years of professional experience, our mission is to produce high-quality, meaningful work through collaboration. We believe every project is a partnership, our clients learn from us, and we learn from them.

Right now, our team is involved in several exciting projects. We’re producing a sci-fi film created entirely by Wisconsin-based talent, as well as continuing work on our award-winning docuseries, The Next Frame, which highlights inspiring creative voices from across the Midwest. We’re also collaborating on Solstice, a feature film by Daniel J. Pico of Pico Blvd Entertainment. It’s an exciting time for us, we’re building stories that reflect the heart and creativity of our region.

Amazing, so let’s take a moment to go back in time. What breaks the bonds between people—and what restores them?
In today’s creative world, I’ve seen many productions fall apart because of a lack of confidence or motivation. Filmmaking isn’t easy and honestly, that’s what makes it great. If it were simple, everyone would do it. It’s the challenge that pushes us to grow.

I’ve worked on projects where people committed at the start but dropped out halfway through or didn’t show up when they were needed most. That can really affect a team’s trust and momentum. When you step away from a collaborative effort like that, it doesn’t just impact the project, it impacts your credibility and the relationships built around it.

What restores those bonds, in my experience, is honesty and accountability. Being upfront with your team, following through on your commitments, and not being afraid to finish what you start. That’s where real trust and collaboration are rebuilt. When people come together with genuine communication and shared purpose, that’s when creativity truly thrives.

Was there ever a time you almost gave up?
Back in 2011, I took part in my very first 48 Hour Film Project, the world’s largest timed filmmaking competition where you have just two days to create a film from start to finish. I had just finished my second year of college and knew it was time to challenge myself. To step up and show what I could do. For the first time, I hired actors, brought on a makeup artist, secured a filming location, and handled all the official paperwork. It was a crash course in real-world filmmaking, from writing the script to producing the film in a weekend.

My team and I worked tirelessly and submitted our film on time in Milwaukee. I felt on top of the world, proud of what we had accomplished and eager to see how it would perform. When it finally screened, the audience reaction was good but we didn’t place or win any categories. I was crushed. For a moment, I thought about walking away from filmmaking competitions altogether.

That’s when my best friend, Brendan Adams, looked at me and said, “Why are you giving up? We just did something incredible.” He reminded me that success isn’t always about winning awards, it’s about finishing what you start, learning, and growing from the experience. He was right. We achieved something few people ever attempt, especially on a first try.

If I had given up then, I would have missed out on so many opportunities that came later, including one of my proudest moments: having a film screen at the Cannes Film Festival in France in 2024. That experience taught me one of the most valuable lessons of my career. Never give up, say yes, and keep moving forward.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What’s a belief or project you’re committed to, no matter how long it takes?
Since 2021, I’ve been fully committed to a docuseries I created called The Next Frame. Its mission is to shine a spotlight on the incredible and often overlooked creative talent throughout the Midwest. Over the years, I’ve had the privilege of working with so many gifted individuals, and each one has taught me something new.

The Next Frame isn’t just about filmmakers; it celebrates the entire creative ecosystem. From prop makers and music composers to visual artists and performers. Every one of them deserves their moment to be seen and appreciated.

Beyond that, the series carries a bigger message: the entertainment industry needs to recognize the Midwest as a thriving hub of creativity. The talent is already here, we just need more opportunities and support to build sustainable creative careers in our region. That’s a mission I’ll keep pushing forward with, no matter how long it takes.

Okay, so before we go, let’s tackle one more area. If you knew you had 10 years left, what would you stop doing immediately?
If I knew I had ten years left, I’d stop putting things off. Life moves fast, like film frames flickering through a projector and before you know it, the moment has passed. What I’ve learned is to make the most of each day, no matter what. Don’t waste your time or your potential. Just do it.

I’ve also learned not to let others hold me back. Whether it’s because of money, doubt, or disbelief. You’re only young once, and during that time, you have the most energy and passion. Use it. Say yes to opportunities. Create. Take risks. Stop second-guessing yourself and act now, because one day, you’ll look back and be grateful that you did.

Contact Info:

Image Credits
Photographer: Elizabeth Schatz
Copyright: Chair on Stair Films

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
Highlighter Series
Was there ever a time you almost gave up?

We connected with some of the most resilient folks in the community and one of

Highlighter Series
If you could say one kind thing to your younger self, what would it be?

We asked some of the wisest people we know what they would tell their younger

Highlighter Series
What are the biggest lies your industry tells itself?

Every industry has its myths—stories insiders repeat until they sound like truth. But behind the