Today we’d like to introduce you to Sam Cross.
Hi Sam, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I found film production while I was procrastinating studying for my Electrical Engineering degree at UT. I knew that EE wasn’t what I wanted to do, but I never felt a spark for work like the first time I opted to make a video essay instead of a traditional one for my British Literature class. Ever since then, I was hooked.
I wanted to drop out and go full send on a film career, but I had 3 years of student loans accumulated by that time. So I pivoted. I changed my major to one I believed would give me the salary to pay off my loans, and the flexibility to see if this film thing would work. I graduated two years later with my degree in Secondary Education, and went to work.
I spent every second of free time learning, experimenting, and trying to get on every set possible as a P.A. I was usually a little older than other Production Assistants, but that also came with a maturity, work ethic, and perspective that was uncommon. I lived off my teaching salary and used my freelance money to pay off those pesky student loans, as well as acquiring my own production equipment. Five years later, I quit my teaching career to pursue video production as my full time job.
It was a winding road, but It’s been over two years now, and I wouldn’t trade my experience for anything. I learned a lot in college, in the classroom, and on film sets, which has resulted in a pretty well-rounded set of skills. I started my own company, Owlbear Media, LLC, and am finally able to hire a lot of the people I used to PA alongside when I was working two jobs. Now I get to do what I love, with people I like (and make decent money doing it).
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Sacrificing my weekends and breaks while teaching was difficult. Working 24/7, never taking a real vacation. Late nights trying to finish a video edit, followed by lesson planning. Having a summer production asking me to follow them to New York, but having to turn them down because I had to go back to work was particularly heartbreaking.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I run Owlbear Media, a video production company that specializes in cinematic, story-driven content for brands, organizations, and causes that actually matter. I direct and shoot everything from commercial spots and branded docs to educational series and nonprofit campaigns—typically with a small, efficient crew and high-end equipment. What sets me apart is my ability to make even low-footprint shoots feel polished and emotionally grounded.
Most of my work sits at the intersection of real people and real impact. I’ve filmed everything from coalition carnivals that help keep kids off drugs to national ad campaigns for Fortune 500 brands. But the projects I’m most proud of are the ones where I can see the ripple effect—where the video helps shift perception, open conversations, or unlock funding for something important. I have multiple projects in the works right now to help coalitions and hospitals generate funding for things that truly matter.
How do you think about luck?
I don’t really believe in luck. I believe in randomness and preparation. Opportunities come and go all the time, often at random, but if you’ve been putting in the work, learning, practicing, building relationships, you’re ready when they show up. That’s not luck; that’s being prepared.
There have definitely been moments that might look like luck from the outside—landing a big client, meeting the right person at the right time—but I was only able to take advantage of those moments because I’d been doing the work long before they appeared.
Contact Info:
- Website: https://www.owlbearmedia.com/
- LinkedIn: https://www.linkedin.com/company/owlbear-media-llc/
