We Chat With: Brendan Bolger of Chicago Cupcake's Not-So-Average Cupcake Truck

We Chat With

Interviews with local chefs and restauranteurs.


[Photographs: Carol Hilker]

In a city that is over-saturated with cupcakes, during a time when the craze almost seems to have ceased, I couldn't help but think, "Why in the hell would anyone decide to launch a cupcake truck?" For this very reason, on a day that was almost 100 degrees at 1:00pm, I trekked to Chicago Cupcake's red truck to taste them for myself.

On the way there, my boyfriend kept whining, "What kind of idiot sells cupcakes on a hot day? Isn't there an ice cream truck driver you can interview?" But then we met the owner of Chicago Cupcake, Brendan Bolger, and we realized he was no idiot, in fact, he is pretty clever.

When you first meet him, you will quickly notice that he doesn't necessarily strike you as being a cupcake baker (I picture 30-something mom bloggers and older ladies), but the Naperville-native, former Montana resident and lifelong outdoorsman is a guys-guy who is one part businessman, and one part pastry chef. Bolger, who left behind a career in real estate development to pursue baking, says that baking has been his passion for more than 15 years. I believed it when I bit into one of his blueberry cupcakes and realized that these sweets are not like your average dry, dense cake with buttercream so thick and high that it hurts your jaw to eat; these cupcakes are the exact opposite.


The Plain Jane

To clarify, this cupcake isn't really cake. There is absolutely no cake anywhere. The "cake" part is more of a cheescake or mousse. And it has a crust—a crunchy, buttery, melt-in-your-mouth crust that the cheesecake/mousse-like base sits proudly on top of. Atop the "cake," Bolger layers a thick swirl of mild, soft buttercream frosting that is topped with sprinkles and other garnishes. Although the cupcake is rich, it's absolutely dreamy. (And for the record, it is a wonderful treat for a hot day. )

Earlier this week, I spoke with Bolger about the Chicago Cupcake food truck, his favorite flavors, and what is takes to reinvent the cupcake.

What is the first memory you have of eating a cupcake? My first cupcake memory is sitting on a picnic bench in the backyard eating one of my mom's homemade cupcakes. Some kind of Duncan Hines chocolate cake and frosting.


What's Up Peanut Butter Cup

What are the most popular flavors on Chicago Cupcake's menu? Red Velvet, S'mores, Plain Jane, and Banana Fosters. My personal favorites are the Motherload (pretzel crust, peanut butter, chocolate cake, caramel buttercream) and What's Up Peanut Butter Cup (chocolate cake on a graham cracker crust, peanut butter, peanut butter buttercream). I love peanut butter.

Who comes up with the flavor combinations? Are there any flavors you won't put on the menu? Flavor conception has come from a few people: myself, friends, family, costumers of Chicago Cupcake. Our flavor of the month [last month] was Lavender Jane. I may have to go back to the drawing board with that one. Other than that, we've been pretty happy with our flavor creations. I have many more waiting in the wings.

In a city that is saturated with cupcakes, what sets Chicago Cupcakes apart? There are a couple things that set us apart. First is the crust, our foundation. Secondly, our cakes are more moist and flavorful than most traditional cupcakes. You'll just have to try one to see.

How does a crust and a cupcake work? Why is this a good thing for the cupcake? The crust gives the cupcake an added and pleasing texture that you otherwise don't find in a cupcake.



Given your experience so far with the food truck scene here in Chicago, what advice would you give anyone thinking of taking a catering business to the streets? Make sure you get air conditioning in your truck! In all seriousness, [the food truck] is a great way to get your product out to the masses, and it enables us to go to the people.

Do you have any thoughts on the ordinance recently presented? I think it is great that they will allow for vendors to cook on the truck, but Chicago Cupcake will continue to pre-package in our commissary. I also think it is great that we know we will have designated times at certain high traffic areas. That way we will know on certain days and times where we will be. My concern is that there will be 10 stands with room for two trucks—20 total. There are currently about 58 trucks on the streets. As long as we are free to continue using the city streets like we do now, I think it will be a great opportunity for our businesses to thrive. There is some question as to the other pieces of the ordinance, so we will have to see how they shake out.



Besides the food truck, what other events do you do? We have a delivery business that services the corporate world. We have a couple events coming up where we will deliver and help to handout 500 and 600 cupcakes. We also participate in weddings, showers, and birthday celebrations.

What are your other favorite restaurants and food in Chicago and/or suburbs? I love a good steak. David Burke's is my favorite steakhouse in Chicago. It was the best steak I've ever had (55 day, dry-aged).

Chicago Cupcake

The best way to find Chicago Cupcake's food truck is to follow them on Twitter and Facebook or to check out its website. Twitter: @Chicago_Cupcake Facebook: Chicag-Cupcake/Facebook