Creating Opportunity Free Enterprise Staff  | January 11, 2016

Becoming the Boss: With Great Cookies Comes Great Responsibility

This story originally appeared on Above the Fold, the U.S. Chamber of Commerce’s digital platform featuring analysis, commentary, and real stories about the intersection of government and business.

Welcome to Becoming the Boss, our series celebrating small business owners who have made the transition from solo-entrepreneur to employer. Check back periodically for new installments.

Kirk Francis – now known around the nation’s capital as “Captain Cookie” – says it all started when he was a 4-year-old kid in Oklahoma.

“I’ve always been obsessed with cookies,” Francis, who owns and operates the increasingly popular Captain Cookie and the Milkman food trucks in Washington, D.C., said in an interview. “I’ve been working on my chocolate chip cookie recipe for about 25 years now.”

Francis moved to D.C. after college, where he worked as a consultant for the Department of Homeland Security. He continued to bake and tinker with his favorite chocolate chip cookies on the side, and eventually, he decided to try to turn his passion into a career.

Captain Cookie’s food trucks can now be spotted all around the Washington area, and they operate out of a commercial kitchen facility on Pennsylvania Avenue, where Francis recently opened his first brick-and-mortar cookie store. It’s here that all the ice cream and ingredients for the made-from-scratch cookies are housed, and it’s where he and his team experiment with new concoctions such as pumpkin muffaroons and pecan sandies.

Today, Captain Cookie has three trucks on the road, and Francis is looking to bring a fourth to the campus of his alma mater, the University of North Carolina at Chapel Hill. In the interview, he discussed those expansion plans, his company’s most delicious perk, his most memorable recipe experiment flop (lime zest, anyone?), and the scariest part about becoming the boss.

When did you start selling cookies?

I always had brought cookies to school or work, and one day, one of my co-workers approached me about selling to local cafes. I started selling to Sidamo Coffee and Tea along with a few other places back in 2009.  During that time, I worked about 20-30 hours a week on top of my full time job. I saved up for three years and then bought an old Washington Post newspaper delivery truck and started transforming it into the Captain Cookie truck.

How did you become “Captain Cookie?”

Well my wife actually came up with the name. There were a few different other options: “Sugar Saloon and Cookie Bark,” for example, which would have had a saloon theme, and “Kirk’s Cookie Cure all,” which would have a medicine wagon theme.

Ultimately, I sent a survey to 50 of my friends and Captain Cookie was the winner. In February 2012, I quit my job, drove the truck into D.C. for the first time, and started selling cookies.

When did you hire your first employees?

I hired my first employee, Andrew, when I rolled the first truck out in 2012. He was my former roommate, a great baker, and at the time unemployed. Actually, all of my first few employees were unemployed friends who just needed some cash in between jobs. It wasn’t until I rolled out my second truck that I hired my first full-time employee, Sam.

What does it mean to you to be an entrepreneur and to be creating a job not only for yourself but for other people, too?

It’s a cool feeling. I was really nervous at first, because I had been doing my own thing and making it up as I went along and now I was directly responsible for someone else’s livelihood. If I went out of business in the next few months, it would impact more than me. I also now had to figure out vacation policies and all of that. Now I employ about 40 people, both full- and part- time, and they get to eat all the cookies they want.

Why did you decide to add a brick-and-mortar store?

It was basically serendipity. I was walking to meet the truck at George Washington University and I saw a for lease sign in one of the windows. The realtor said the space I was calling about would be too big but that a local ice cream place was going to go out of business in two months.  They put my name on the list with about 20 other businesses.

Then it got tricky. My business was new, so they didn’t trust me much. I had to pay a half year’s rent up front, submit a lot of forms and value everything that we had. That dragged on for four or five months, and I didn’t count on it happening until we printed and signed the lease. I kept thinking this won’t work out and tried not to get attached.

What’s your favorite part about being Captain Cookie?

Seeing people enjoy the cookies.  They really are good and people really enjoy them.  That’s immensely gratifying, and it’s part of the reason I wanted to do more than sell wholesale.  I’m now able to see how much people like the cookies, just like when I brought them to work, but that’s not the case when you’re selling to stores. I knew the cookies were selling, but I wasn’t able to interact with a customer and hear them say, “Wow, those are really good.”

Clearly, your cookies have been a hit. But did you ever try a recipe that just didn’t work out?

The one I most remember were Lemon-Lime Pinwheels. I zested and juiced about 120 limes and lemons, and we used them to make a lemon sugar cookie dough and a lime sugar cookie dough. It was a lot of work, and although I thought they were awesome, our customers were completely uninterested. The conversation would go something like: “What’s that? A lemon-lime pinwheel? That sounds interesting. I’ll have two chocolate chip, thanks.”

Needless to say I ended up eating a lot of lemon-lime pinwheel cookies.