Building a graffiti business, letter by letter

Philadelphia favorite son and Grammy Award-winner Questlove has published “Creative Quest,” a collection of inspirational stories and lessons about living one’s best creative life. In this spirit, Speak Easy has asked Philadelphia artists to share stories of their own creative quests.

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I’ve been drawing for as long as I can remember. I was very interested in graffiti and graffiti culture in high school, and that’s definitely when lettering became my focus. I would draw graffiti and mess around with traditional wildstyle lettering, all in a sketchbook, never trying to paint it.

At Rutgers University, I studied marine science and ecology, but I was pulled toward graffiti in a stronger way. I saw it everywhere. A few friends were painting, so we all formed a crew. I was painting graffiti weekly and working a full-time job pertaining to my major. That was right around 2006.

After graduating from college, I searched desperately for a cool job that fit my degree. I worked a handful of steppingstone jobs, hoping to land a career in a marine research field or with Fish & Wildlife.

These were my busiest graffiti years. My friends and I had a pretty strict routine of painting freights three times a week, and we stuck to that up until recently. These are definitely the years that built my foundation and my reputation for being a “straight letter” guy in the national freight graffiti community. For me and my friends, it was more of an excuse to meet up a few times a week, catch up on things, vent about our jobs, enjoy some bar food, and get some work done.

After painting for years, it just becomes a routine, less of an adrenaline rush and more of an escape from stress. Even during these years, I had a checklist of techniques I wanted to use (cracked, slimy, ripped, upside-down, bevel, chrome), probably a bit of foreshadowing things to come.

While I was working a crappy job and painting graffiti a handful of nights a week, I was also juggling occasional mural jobs. In 2008, while painting a legal wall in Camden, I was asked by a roller rink owner to paint the entire rink floor in a Las Vegas theme. I had never done any murals before. I had no idea how to price it out, what supplies I needed, or how long it would take. This definitely planted the seed for my future business. I realized I could quickly make a week’s pay in only a few hours.

By that time, I was already using Glossblack as a business name, originally with the intention of selling handmade fonts, but that quickly faded away as mural business took over. I promoted myself on Craigslist routinely, and mostly I directed my skills toward day cares and other cartoony jobs.

Fast forward to 2015. A client gave me full artistic freedom on an empty corner lot. I painted a large ‘PHILLY’ in an illustrative chrome effect, as well as a vibrant letter-based fence surrounding it, right in the heart of Fishtown. After that, things really started to snowball, and I was painting murals almost weekly, as well as picking up some major corporate clients.

In 2016, everything fell into place. My wife and I were newlyweds, expecting our first child. I emptied my savings account and bought a home. I bought my wife a much-needed new car. And with all of these new financial burdens, I decided to quit my job. It was one of the best decisions I’ve ever made.

For the longest time, I had wanted to be able to support myself and my family with my art, but I never really imagined how it was possible. I think I always relied on the idea that I would work for someone, maybe painting a movie set or learning faux finish. Looking back, I feel like it was smacking me in the face for years: Spray painting large-scale work was my specific strength. My lettering, and the way I approach structure and texture, is unique to me. That’s the avenue I should be pursuing; that’s what will become my trademark.

Today, I feel so fortunate to be where I am. Some days I say to my wife, “I’m glad I’m not cleaning a fish tank right now” or “I’m glad I’m not sitting in traffic right now” — which are both things I was doing daily only two years ago. It still feels a little weird to have this new freedom, and I want to make the most of it.

As much fun as it is to work on my own art, I actually enjoy the pressure and challenges of working with a client and their brand. It’s a great honor to be trusted to that degree, that a major company is willing to collaborate or put its image in my hands. It’s also a great reminder that I’m doing something right.

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Raised in the Philadelphia area, Jimmy “Glossblack” is a nationally recognized American graffiti writer.