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From the Business Section of the Washington Post – December 1997

All my life, I had been “that kid who can draw,” the one classmates would come to for party flyers, T-shirt designs and illustrations to use as a template to get their jeans painted. I never had a formal art class beyond the 6th grade, so my designs were usually based on cars, comic books, or the latest movie (“Star Wars” was a big influence). My sophomore year in college, I applied for a position as the graphic artist for one of the student centers on campus. I had worked with the previous artist who held that position, who taught me about paste-up, and using Letraset letters and rubylith for my design work (anyone remember those?) instead of doing everything free-hand. I didn’t get the job, and when I found out I was so angry that I went back to my dorm room and drew what had been my best work to date, and which started me on a new path.

I had a college friend who had graduated a couple of years before me. He was in his second year of medical school when he realized that he didn’t want to be a doctor. His parents, as you can imagine, weren’t happy, and he had come back to campus to visit some of us younger guys and explore some career options using the university’s resources. While he was there, I showed him my design and some others I had done. During our conversation, he had an idea: we should go into business selling T-shirts with my designs on them! Neither one of us knew anything about starting a business or selling, but we had a great idea and thought we could make some money. He went and drew up a contract (he decided he wanted to be a lawyer), which was primitive by today’s standards, and came up with a name: Masai Enterprise (no ‘s’). It was November 1986.

Our first product was a towel, with the design I created as the result of my rejection. The production process was a disaster (they printed it too small, on terrycloth, and all the detail was lost). Despite the imperfection, we were stuck with them. Our plan was to sell them at an event in New York City on New Year’s Day. We went without enough money to get in. We were selling them at a ridiculously low price ($5.00), but we were able to to sell enough outside to buy tickets. To this day, I consider that first “cold” sale to be my good luck charm.

We sold almost everything we had that day. For the next year, we used the money we made to buy more shirts, get them printed, travel to events and sell them. We created designs that were original and resonated with the people we knew and the culture we were a part of. And we had a lot of fun! It wasn’t until years later that I realized there was a word for this – entrepreneurship.

That fall, my partner enrolled in law school (he eventually got his JD/MBA and became an investment banker) and I finally got serious about graduating and focused on my studies. Masai Enterprise was put on the shelf, but it had sparked something that would never be extinguished. The rest, as they say, is history…

So often, we’re so focused on today that we don’t tell our story. How did you get started?