Career Alternatives, Food

From Contract Attorney to Captain Cupcake

I have come to the conclusion that most Americans really enjoy three things:

  1. Freedom
  2. Earning money, and
  3. Buying food out of a truck.

Think about it. Remember as a kid when you would hear the music from your local ice cream truck making its way down your street? Remember running towards it as if your life hung in the balance, all the while thinking, MUST-GET-ICE CREAM-NOW!? And it didn’t matter whether you had 14 gallons of every conceivable flavor of ice cream at home; you just had to have your King Cone or Chocolate Chip Cookie Sandwich. Those were good times.

Well, roughly a year ago, George Washington University Law alum Sam Whitfield was reviewing documents for discovery as contract lawyer in Washington, DC, when he and his colleagues began craving cupcakes. The problem was no one wanted to venture across town to a local hot spot, Georgetown Cupcake,to pick them up. That’s when Sam had his first rendezvous with cupcake destiny.

“I thought, what if we could get cupcakes delivered to us?” he said. “I come up with three or four crazy ideas like this every day.”

Soon thereafter he found himself investing in a truck, a baker, and cake mix (lots of cake mix). In a very short time, Curbside Cupcakes was born, but would DC find his idea as delicious as he did?

[Disclaimer: No cupcakes were harmed in the writing of this post. Honestly, I’m not really that even into sweets. However, if they were to consider creating a Bacardi-infused cupcake anytime soon, I could change my mind. But that’s another post altogether.]

Lawyers seem to be at the forefront of the cupcake/sweet craze that’s currently gripping the nation. A little over a year ago, Elie made mention of NYLS grad Lev Ekster, the creator of  the Cupcake Stop, which is pretty much the New York City version of Curbside. Another NYLS alum, Mia Bauer, founded the popular bake shop Crumbs in Upper Manhattan. Ironically, DC has its own law school bakery bizarro world as well. Whitefield is not the only GW Law Alum to make his way into the cake business. Fellow grad Warren Brown started the highly successful Cake Love. Seriously, what is it with these two schools when it comes to baked goods?

As the economy cratered toward the latter part of 2008, Whitfield, who has contracted at such firms as WilmerHale, Clifford Chance, and Hogan & Hartson, decided to focus exclusively on his cupcake delivery service idea and dove right into the business.

“I literally stopped contracting on October 31st of last year, and began selling cupcakes full time on November 2nd,” he said.

And in terms of Curbside’s success, to quote Brad Pitt from Inglorious Besterds, “Business is booming!”  Operating for just over eight months, Whitfield sells 700-1000 cupcakes a day. With his cupcakes going for three bucks a pop, you can do the math on what he ballparks in gross. (NOTE: The cupcakes are cheaper by the dozen.)

Sam did not enter this cupcake venture alone. His business partner is also his fianceé, Kristi Cunningham. The two expect to tie the knot this November.

“I see her every day, all the time. It has its benefits, and, well, that’s all I’m going to say about that.”

See, he’s already speaking like a successful businessman, and husband.

Curbside has also amassed quite a following in social media. They have over 10,000 fans on their Facebook page and over 4000 followers on Twitter. Their early success also landed them a spot on CNN, as well as other video spots here and here. Plus, their trademark pink truck has become all the rage in DC.

“It’s been amazing,” he said. “When we first started, we would see one or two people waiting for us when we were making a stop. Now there are usually lines of people waiting for us, some actually stand in parking spaces to reserve us a spot.”

Starting with the classic vanilla, chcocolate, and red velvet cupcakes—“In DC, you have to have red velvet,” says Whitfield—they have expanded to 14 different varieties including Almond Joy, key lime, and lemon.

“Lemon came as a suggestion from our Facebook page,” says Whitfield. “We are currently working on strawberry.”

So, how has the change from lawyer to cupcake king been treating him? Is Curbside already turning a profit?

“I am able to pay my mortgage, but I would not say I’m ready to go out and purchase a Bentley.”

Yet, there are intangible benefits for Whitfield as well.

“The work is harder, and I do get more tired, but I am a lot happier.”

Gabe Acevedo is an attorney in Washington, D.C. and the owner of the e-discovery blog, He also writes on legal technology and discovery issues for Above The Law. He can be reached at

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