Reinventions: Taylor Rosenbauer Fingerboards Into Agency Ownership

What were you before? 

I got my start as a fingerboarder. For the uninitiated, fingerboarding is the art of simulating skateboarding tricks using your fingers and a mini skateboard. I got into it while I was sidelined from competitive skateboarding after I broke my arm as a kid. I loved how rewarding it was to work on tricks over and over, seeing how I could push the limit of what was possible.

Around the same time, YouTube was just starting out. One day I grabbed my family’s camcorder and made a video of my fingerboarding tricks. That video went “viral,” and things took off from there. I created a studio in the basement and was making regular videos for my YouTube channel, which gained more than 30,000 followers. Before I knew it, I was traveling the world, had my fingerboarding featured in a music video, and sold a show called “FingerTips” to Disney before even graduating from high school. 

I’m no longer active, but I’m still pretty well-known in the fingerboarding community as the guy who raised the bar in video production quality.

What triggered your reinvention(s)?

By nature of creating fingerboarding videos, I became obsessed with filmmaking. I taught myself cinematography and how to edit, animate and build a following on YouTube. The feedback I’d get from the community kept me going, always trying to make better content to one-up myself. 

Although I majored in philosophy and political science in college—with the intentions of going to law school—I ended up following my creative passion. My first job out of school was as a video producer and motion designer at a social media agency. It was a dream gig: I was a one-person department and had a whole studio to myself, where I spent every day creating video content for the agency’s clients. I was given a lot of creative license and loved every minute, so much that I would go into the office on weekends just to explore new ideas.

It was a job I never wanted to leave … until I took a chance on something new. I met a former hedge fund manager who was starting a fintech company and needed a creative specialist. It was a huge risk—many people in my life advised against it—but I saw this as an opportunity to once again push myself and expand my skill set. 

I wasn’t making a bet on the startup’s success; I was betting on myself. And it paid off. I grew as a creative, was responsible for all graphic design and video content, and eventually led digital product design. That experience gave me the confidence to run my own design business and was ultimately the genesis for RocketAir. 

What did the first steps look like?

Ironically, I have social media to thank for that, too. A friend of mine passed along a LinkedIn post from an education company that was looking for a developer to design wireframes for their new platform. As a product designer, it was a red flag. I approached the edtech company and convinced them of the value of taking a design-first approach to launching their product. That was my first new business pitch, and they became RocketAir’s first client. 

From there, I needed to make our first hire to help execute on the project. That was Brian Hoff, a former Apple designer who had been running his own design firm for 11 years. We connected on Dribbble, got along really well, and decided to team up. He’s still our creative director five years later. 

What was one hard obstacle to overcome?

As someone who’s not a fan of learning in traditional settings, I’m mostly self-taught. When RocketAir was starting out, I remember having to overcome a sense of insecurity around that. I was running a business not having attended business school. I was leading a design team never having officially studied design. But every insecurity has a flipside, and looking back, my background in being self-taught has helped me become the type of leader I needed to be. 

I have a habit of being curious and open to new ideas, perspectives and ways of doing things— something I hope I’ve instilled in the company culture at RocketAir. I don’t assume I have the right answer (or that there even is a “right answer”). Because I’m often learning on the job, I also find myself digging in and paying attention to the details. The degree to which a leader truly cares about a matter at hand is, I think, critical to their team’s success. 

What was easier than you thought?

I wouldn’t say this is necessarily easy, but the growth of the business over the years has been pretty organic. Our first client referred us to others, then those clients referred us too. People I’d crossed paths with earlier in my career got in touch. Past clients came back around. We did good work, and more work came our way. 

It’s “easy” in the sense that it’s not overly complicated: Treat people well. Don’t burn bridges. Uphold high standards of quality.

What’s something you learned along the way that other people, hoping to do something similar, should know?

It’s true what they say: As a business founder/owner, you have to work on the business, not in the business. RocketAir is now in its fifth year, and to get to this point I’ve had to learn how to take a step back from the client work and day-to-day operations in order to scale the company.

I love being in the work, but my involvement isn’t sustainable. You have to hire the right people and trust them to do what they do best so that you can focus your energy on things like the long-term vision of the company, the team culture and business development. One of the best decisions I’ve made at RocketAir is promoting our former executive producer, Danielle Solis, to managing director. She does an incredible job running the day-to-day of the agency.

Did anyone or anything inspire you along the way?

Ueno founder Haraldur Thorleifsson. He’s been a big advocate for accessibility. I look up to him not just for his talent as a designer and the way he built his agency, but also his social impact. 

What has fundamentally changed for you?

Everything honestly, but the biggest shift is probably the enormous responsibility I feel now. I’m not just thinking about my own career, I’m thinking about the growth and development of our team members. I’m not only focused on the success of my business, but our clients’ businesses. The weight of every project outcome, every aspect of the team member experience, every client relationship is on my shoulders, and I don’t take any of that lightly.

Do you think you could go back/do you want to?

My fingerboarding videos are still on YouTube and Disney.com and there are many people in the community who ask if I’ll go back to creating. But the truth is, the obsession I had for mastering fingerboarding tricks has turned into an obsession with mastering how to run an agency. Once I conquer something, I move onto the next challenge, so it’s unlikely I’ll go back. I still have so much love for the community, though, and I always keep a fingerboard on my desk.

Tell us your reinvention song.

I don’t think I can pick just one song, but the soundtrack for my reinvention is Tycho. His music feels endless and distracts the part of my brain that’s always on, allowing me to focus. 

How would you define yourself now?

Founder and CEO of design and strategy company RocketAir. If I had to sum it up, my role is focused on two things: helping world-class talent do the best work of their lives and helping brand and product leaders win by design.

A big part of that is fostering a workplace culture that enables everyone to give their best every day. That sometimes means testing new things, like our recent four-day workweek pilot—it ended up benefiting both our team and our clients, so we’ve made it permanent. 

Running RocketAir is miles away from the days of being a “fingerboarding celebrity,” but I’m still spending the majority of my time pushing myself to get better and better.