The Sweet Smell of Success

First off, an apology. My day job has been keeping me uber busy the last two weeks, so I have not been able to carve out time to devote to the blog the way I usually can. This caused a lot of guilt on my part. Especially when I was asked (online and off) about my absence. Thanks for all of you who were concerned. I am just fine, just a little overextended.  Enough about my pesky day job, let’s get to the good stuff!

In the second installment of my “Foodie Fable” series I focus on two trends very hot in Boston right now: food trucks and cupcakes. While food tucks were only legalized by the City of Boston in 2011, the cupcake craze dates back to 2000. By my calculations, that trend hit its tipping point when Carrie and Miranda sat in front of Magnolia Bakery in New York’s West Village scarfing down cupcakes with a heaping dose of Pepto-Bismol pink frosting on top during the third season of “Sex and the City.” That scene made cake’s little brother cool for adults to eat and not just at kids’ birthday parties.

While it was not my initial goal to kill both of these trendy culinary birds with the same stone, this twofer came in the form of Diana DeMarco, the owner of The Cupcakory, a charming little food truck, perfect for the old fashioned look and taste of her products.

The Cupcakory's rotating menu includes cookies & cream, red velvet, slated caramel and a Samoa, a tribute to the Girl Scout Cookie

The Cupcakory’s rotating menu includes cookies & cream, red velvet, slated caramel and a Samoa, a tribute to the Girl Scout Cookie

Diane jumped on the food truck bandwagon after a twenty-year career in publishing came to an end when the economy hit the skids four years ago. She had always loved baking, and at that point neither the food truck craze nor the cupcake trend had hit Boston yet. Actually food trucks were not even allowed on the streets of Boston. So after a year of testing recipes and retro-fitted a truck she found on Craigslist, Diane took to the streets of Brookline selling her cupcakes.


Zoe about to make another customer very happy

“I just wanted to do something that would make people smile,” Diane told me as we chatted in the relatively close quarters of The Cupcakory truck, which is smaller than your standard food truck, and has a retro-vibe to it. “No one can walk up to this truck and not smile at something.” Her menu is a cut-out in the side of the truck where her daily offerings are listed and showed off, so you know exactly what you are getting. In the summer she frequently has potted plants outside, and a little awning to provide momentary shade for customers as they order.


The adorable Cupcakory truck

Today Diane and Cupcakory can be found rotating between  Jamaica Plain, Roslindale and yes, still in Brookline. That’s where I caught up with her on a recent Sunday afternoon. She was on hand selling cupcakes at Brookline Day in Larz Anderson Park. As she does every night before she heads out in her truck, she determined her menu for the next day and she baked all the cupcakes she estimated that she would need. She tries to use as many organic and locally sourced ingredients as possible. She also prepares the corresponding frostings for her cupcakes, but the magic really happens inside the truck when Diane and her wing woman Zoë ice the cupcakes (and in some cases cover them in sprinkles, coconut, cookie crumbs or caramel) when they are ordered.

Many customers, accustomed to the instant gratification of today’s food service industry had to wait a few minutes while their cakes were frosted before their eyes. Inevitably this delay left a smile on their faces as they watched their tasty treat get topped. I heard a lot of “Oh, you frost them right here?” Yes, they do. And while I may not have found my next passion in life in the back of a food truck, I certainly got a good sense of what goes on in there. My attempts to frost cupcakes started out rough. I found that its a real skill to be able to squeeze out frosting in a way that produces an appetizing, non-phallic, dollop of icing. Chilled frosting can be a little stiff, making it difficult  to squeeze out of the frosting bag in a smooth, elegant way, but with some practice I hit my confectionary stride. I don’t mean to brag, but while frosting may not be a strength of mine, sprinkling sprinkles certainly is. I mean I was really good.

icing the cupcake

While I may not be good at frosting, I am a fantastic sprinkler

While there are things I have wondered about food trucks (such as can they wash their hands? Yes!), there are some aspects of being the proprietor of a food truck that never occurred to me. One of these is the idea of competition. When a brick and mortar restaurant opens it knows what its neighbors (i.e. competition) are. If you were opening a cupcake shop, you would likely not lease a space next to two other desert shops. But in the world of food trucks your competition changes each day and if your cupcake truck is parked with an ice cream truck on one side and a cookie truck on the other, you may have a less than busy day. This is the risk that Diane, and every other food truck operator, runs every day. Bad weather is another detriment to business. It never really occurred to me all the small variables that can impact business when said business has a set of wheels.

Diane says that even now, Cupcakory is still a work in progress. Originally, she thought by this point she would have a traditional brick and mortar shop, not just a food truck. “This whole thing didn’t happen exactly the way I thought it would,” Diane mused to me. “But I’m enjoying the ride.”


Diane (left) and Zoe, the ladies of The Cupcakory

I can certainly say the same thing about myself, and maybe you can as well. We’re all works in progress, aren’t we? But being able to enjoy our own individual rides on this strange, exhilarating, sometimes frustrating, always fascinating road we call life is a recipe for happiness. So I’m going to stop relying so heavily on my preconceived GPS (pardon me while I push this metaphor to its limits), and just enjoy the trip.

Many thanks to Diane DeMarco and Zoe for letting me climb inside their food truck for the day. You can check out their schedule and find them here. I was not compensated for this post in any way.


3 thoughts on “The Sweet Smell of Success

  1. Pingback: The Cupcakory » Ever wonder what it’s like owning and working on a cupcake truck?

  2. Good stuff… did you have Byrnes at all in mind while scribing this? 😉

    Al Spector director, database processing w 617.226.9778 mu//en

    “It’s not whether you get knocked down, it’s whether you get up.”

    Vince Lombardi

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