20-Something Endeavors: Cap’n Cookie & The Milk Man


What were you doing at four years old? Were you spending your time determined to perfect your chocolate chip cookie recipe? Did this desire follow you even when you went to UNC Chapel Hill to study English and Chinese — promising prospects ahead in a nice corporate job — you still felt a strong desire to share your love for baked goods with others?

Okay so maybe you didn’t follow that path specifically, but that is the experience of Kirk Francis a.k.a. Captain Cookie. He’s now serving the District of Columbia with fresh-made cookies and ice cream sandwiches, and the District is very happy about that. Captain Cookie and the Milk Man, has become a popular staple in D.C.’s thriving food truck scene and was recently voted top 3 Best Food Trucks in D.C. in Washington Post’s 2013 Best of Express Poll.

Francis’ passion for cookies led him to take a path of his own. As the “20 Something Endeavors” series attempts to find an answer to the inevitable question of what it takes to find work we love, this installment suggests it takes a longtime passion for dessert foods, lots of hard work, and a good attitude in the face of many obstacles.

This is the story of how Captain Cookie turned his perfected cookie dough into a sustainable life as an entrepreneur.

To The Chats

Chai & Chats: Can you tell us about your background? What were you doing before you started the food truck?

Kirk Francis: I’m from Tulsa, OK. After graduating from college in 2008 — right into the recession — I moved to D.C. because this is where the jobs were. I got a job as a government contractor for the Department of Homeland Security. I worked there for four years.

Did you enjoy that job?

I liked my co workers – very smart people. They are good people to look up to and young bright people that were cool to hang out with. But the work was frustrating. Gov’t bureaucracy made it hard to accomplish things. One aspect of my job was to write guides — it took 2 years to get one guide approved.

It felt like I wasn’t accomplishing anything. I wanted more out of a career. I thought I could be happy doing a lot of things — as long as they were challenging, rewarding, and useful to the world.

So when did you start thinking about your dream of baking cookies? 

Cookies had been a long standing obsession of mine. I had worked at a bakery part time in college. I always thought that I might open a bakery of my own one day.

When I moved up to D.C. I made some connections to local coffee shops. I used to make cookies and bring them into work. My coworkers introduced me to this coffee shop, Sidamo Coffee & Tea on H St. N.E., and suggested I start selling them there. I started a part time amateur catering gig by baking cookies and putting up a jar in this shop.

I really like cookies. That’s it. I just like cookies a lot.

So you managed this part time cookie catering on top of your full time job?

Yes — it was really hard to keep it up at the time. I had to make a lot of sacrifices. Friday night I had to make dough and sleep less. I’d bake cookies from 2 A.M. to 5 A.M., deliver them at 6 A.M., and then leave at 7 A.M. from N.E. D.C. to get to my job in Fairfax at 8 A.M.

It was difficult, but worth it. I didn’t make a lot of money from it, but it was worth it because I was starting to realize my goals that I did want to start a bakery. It got me practicing to make cookie dough in large packages and I met so many people in the food industry. I met the guy from whom I was able to rent a commercial kitchen, which is needed by law to have a food truck. I also met the guy who invited me into Restaurant Depot, which is basically Costco on steroids and a life saver.

If I had started the food truck without knowing this it would’ve really been rough. I would’ve spent so much more money and would’ve had a lot harder of a time getting started. I was greatly helped by having this experience on a small scale first.

When did you feel ready to make the jump into full time cookie making?

I spent 4 years catering part time. Over this time, I worked to get everything prepared. It took me 1 year to build a truck. I bought a 1988 truck that was a delivery van for Washington Post. I had to drive it back over the bay bridge and because it’s a big empty box, I was getting blown over into other lanes (chuckles).

Then, I saved up about $50 grand from the cookie business over the past 3 years. I made 30-40 craigs list trips to buy a generator, sink, oven, used refrigerator, the works. I built the truck on my off time. Finally, my uncle helped me paint it in the drive way. When it was finally done, I had to fill out the (massive amounts of) paperwork necessary to file a food truck.

Did you get a lot of support from people about making the jump?

A lot of friends and bosses were skeptical. I didn’t tell my dad until after I quit my job.

Wow, that sounds kind of tough. How did you know you were making the right decision? Did a gut feeling drive you during this time? 

Gut feeling is good, but market research is also good.

Sometimes, people overestimate emotions, feelings, and the butterfly aspect of starting your own business — and that’s what leads a lot of businesses to fail.

You have to be ready to not make profit for a long time. I saved a lot of money and vacation time at my day job, preparing well ahead of time before quitting. I also spent a lot of time talking to other food and dessert trucks to get a good idea of what I was getting into.

So, I’d say it’s a mixture of a great deal of research AND a “go for it” mentality. I think sometimes you can be so enthusiastic about your dream that you don’t see all the permits, all the taxes, all the W2’s and all that. You might miss all the details that make it happen.

It’s better to be cynical at the beginning then let it go belly out.

It’s better to be cynical at the beginning then let it go belly out.

Now that you have your own truck, what kind of support do you have? 

The food truck community is a great one. We’re all friends. When I first left my day job to start my own business, I was worried at first that I’d miss seeing my friends. I thought, “It’s just going to be me and lonely.” But, you make a lot of friends with other trucks. Especially the ones that are sticking it out. There’s a lot of opposition in the city.

What are the obstacles that food trucks in D.C. face?

Brick and mortars complained that food trucks are “stealing” business. This is actually a stretch, because business is business — it’s fair business. A lot of different bills were proposed to limit food trucks by D.C. council. Several would’ve effectively put us out of business.

Eventually, the city has settled on a compromise that no one is happy with so it must be a good one. There are no longer first come first serve parking spots for food trucks. Instead it’s settled by a lottery system for the 8 most popular spots each week. It went into effect in December.

Has this battle with local restaurants affected business? 

Yes. Negatively? Yes. My plan the past 2 years has been to be predictable — 4 days out of each week, I’m at the same place. The blue cookie truck (pictured above) has been as predictable as the sun rises in the East. We grew a following. Now, if you don’t get the same days and times, having a loyal following is harder. People don’t know when you’ll be there. Last week we had Union Station on Tuesday instead of our usual Thursday and people were asking, “Where were you guys?”

But we do have help fighting these laws. The D.C. Food Truck Union has been really helpful. They started a petition against the laws. Since food trucks are a new industry, it’s disruptive to the current food business and people don’t like change.

What are some of the most important lessons you’ve learned as an entrepreneur? 

Always research a lot. Really think about who your customers are going to be. If something similar has succeeded, why? Why is what you’ll do better than your competitors?

Be prepared to work hard at it. Be prepared to work on all sorts of stuff you didn’t realize was connected (i.e. paperwork, parking laws, etc.).

Also, START. 100% of businesses that have not started fail. Real statistic.

Be prepared to work hard at it.

What drives you to succeed?

I love what I do. If it’s 1 a.m. and I’m short a dozen eggs, I will go to Harris Teeter and get them. And I’ll finish at 5 a.m. instead of 4 a.m. Because the cookies must be perfect. You have to crush the negative voices in your head — or the calls for sleep. Quitting is not an option.

Do you think passion plays a role in success? 

Yes. Passion is just another differentiator for your business. It just so happens that I have a passion for cookies and have been since I was 4, so that’s how I compete with other cookie trucks.

However, I don’t think passion is as important as doing your research and really working hard. I think there’s a lot people with passion who don’t make it. They might mistake passion as something that would fix bad online marketing or bad location. And that won’t work.

Passion is a great thing. It is important but not as important as taking care of business. Make yourself a business plan. Make sure your market niche is not overcrowded and have customers lined up. People are so excited about cookies so you have to reflect that or exceed it.

I really like cookies. That’s it. I just like cookies a lot.

Passion is a great thing. It is important but not as important as taking care of business.


Thanks for sharing your career insights for 20 Something Endeavors, Kirk!

Do yourself a favor: go get some cookies today. Find where the truck is via Twitter, or drop into Thomas Foolery on P St. NW in DuPont Circle where Kirk sells ice cream cookie sandwiches.

Website: http://www.captaincookiedc.com/

Twitter: https://twitter.com/captaincookiedc

Facebook: https://www.facebook.com/CaptainCookieDC

Yelp: http://www.yelp.com/biz/captain-cookie-and-the-milk-man-washington

Thomas Foolery: http://thomasfoolerydc.com/

Seriously, you guys. Get on that cookie chase. Image via Yelp.


2 responses to “20-Something Endeavors: Cap’n Cookie & The Milk Man

    • Thanks, Cecilia!! He’s definitely got the realistic world view thing down. Also, writing this just made me want a cookie sandwich so bad. Going tomorrow!

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