Melissa Zimmerman created a clever concept to bake a cookie inside each cupcake when she founded It's A Cuppie. She also happens to have been my old babysitter who lived just down the street.

With many flavors to choose from, I was intrigued and needed to get my hands on some of the Cuppies. I reached out and interviewed Zimmerman to get the inside scoop on her cupcake business.

Photo courtesy of Dirty Sugar

Spoon: Tell me about yourself. 

MZ: I grew up on Long Island and went to Northwestern University where I studied musical theater. After I graduated, I moved straight to the city—Brooklyn Heights, where I still live today—and started auditioning.

I babysat for a bit, and then got into the world of Bar/Bat Mitzvah tutoring, which I still do to this day. I also worked for Weight Watchers for four years. I loved telling people that I worked for Weight Watchers and also had a cupcake business. That was fun!

Spoon: How did start your business? 

MZ: Baking was always a hobby of mine. My parents used to bake all the time when I was growing up. Licking the bowl was always my favorite part.

Once I was in high school, I started baking on my own. Fast forward a few years, and my sister was in grad school for vocal jazz and had her final concert. I decided to “cater” the event, baking out of my small NYC apartment. My sister’s boyfriend at the time’s sister was there, and approached me to bake for her wedding. She loved everything I baked and said she would pay me to bake something for her wedding. I couldn’t believe my luck—I would be paid to do something I loved.

At the wedding, I got tons of positive feedback. And as someone without a full-time job, I’m always looking for ways to make extra money. So I decided that if one person would pay me to bake, other people would pay me to bake too, and I should just go for it and start a cuppie business.

Photo courtesy of Wes Tarca

Spoon: How did you get your idea to combine cookies and cupcakes? 

MZ: I decided to take this opportunity to do something creative and inventive, especially because cupcakes were trendy and overdone (and still are to this day).

Around that time, I was reading a book called The Art of Eating In, by Cathy Erway. In one of the chapters, she wrote about how she was bringing cupcakes to a party, and instead of using traditional frosting, she put cookie dough on top of the cupcakes. That sounded delicious to me, and got me thinking… what if instead of putting cookie dough on top of the cupcakes, I put it inside? What would happen? And thus the idea of the cuppie was born.

While the original flavor started as cookie dough inside of a cupcake, the majority of my flavors are cookies inside of cupcakes and not cookie dough. I found that I like the textural contrast of a baked cookie inside of cake. 

Photo courtesy of Wes Tarca

Spoon: What do you like best about running It’s A Cuppie? 

MZ: I love making people happy. When I sell cuppies at fairs, I love that I get to see people’s reactions as they take their first bite. The pure joy they experience—that’s what I love most.

I also really enjoy making new flavors. I love the creativity. And I also love running my own business. I get to make the decisions, I get to bake when it’s convenient for me to bake, and I answer to no one.

Photo courtesy of Wes Tarca

Spoon: What is your most memorable order? 

MZ: I got a catering order for ZocDoc: 400 cuppies. I had never baked that many—not even close. I made only one flavor, SnickerPumpkin, to make things slightly easier for myself, and baked nonstop for three days straight. It was just too much.

I don’t have an official maximum number for orders, but 400 is definitely beyond that number now! You live, you learn.

Photo courtesy of Wes Tarca

Spoon: What is your favorite Cuppie to bake? 

MZ: I don’t have a favorite cuppie to bake—but my favorites to eat,that’s a hard question. I think I have a few that are at the top of my list. Strawberry Shortcake, Brooklyn Brunch, King of Fluff SnickerPumpkin and Chocolate Velvet might be my favorites? I love them all though. They’re all my babies.

Photo courtesy of Wes Tarca

Spoon: Which Cuppies are the most popular? 

MZ: Chocolate Chip Cookie Dough is definitely the most popular. Death By Cuppie and Sprinklicious are probably next in line. 
Photo courtesy of Wes Tarca

Spoon: What are some new flavors for this fall? 

MZ: Southern Decadence is the perfect fall flavor. Gingerbread cupcake with corn cookie inside topped with molasses buttercream. I created it for my future brother-in-law, who is a chef in New Orleans and requested this unique flavor combo. I had been wanting to do something with gingerbread for a while and was thrilled to work on this one.

The other new flavor I just announced is Cinnamon Pretzel: vanilla cupcake with snickerdoodle inside topped with pretzel buttercream. If you are a fan of sweet and salty, this flavor is for you. buttercream, cupcake, chocolate, cream
Photo courtesy of Wes Tarca

Spoon: How do you come up with your recipes? 

MZ: I start with recipes I find online or in cookbooks, and then I tweak them. Every flavor goes through a rigorous taste testing process and usually takes many tries. I need all three components to be perfect on their own—cookie, cupcake and frosting. That’s what makes cuppies so good.

Often, when you get a regular cupcake somewhere, you might think the cake is great but the frosting is meh, or the frosting is delicious but the cake is dry. This is why most cupcakes fail, in my opinion. With cuppies, the cookies are amazing on their own, as are the cake and frosting. That’s really important to me.

Photo courtesy of Dirty Sugar

Spoon: What are your future goals/plans? 

MZ: The constant struggle for me is wanting to grow It’s A Cuppie while also wanting to perform. Being an actor in NYC is running my own business, and it’s hard to run two of my own businesses! They both take a lot of time and energy. I have a chart of flavors I want to create.

I already have 25 flavors (and I also allow people to create their own flavor when they order, by choosing any cupcake, cookie and frosting combo) but there are SO many more ideas I have. I’d love for as many people as possible to know about cuppies. I wish there were more hours in the day! candy, pastry, sweet, goody, cream, cookie, cake, chocolate
Photo courtesy of Wes Tarca

 Spoon: Do you have gluten-free or vegan options? 

MZ: I have one gluten-free cuppie, which comes in chocolate chip cookie dough. The peanut butter cookie also happens to be naturally gluten-free, and all of the frostings are gluten-free, so you can choose the vanilla gluten-free cupcake and customize to your heart’s content! I do not offer any vegan options at this time. I like butter too much. 

Photo courtesy of Wes Tarca

Visit my website to check out the flavors, and then either send an e-mail to itsacuppie@gmail.com or call 917-524-8025. I deliver in NYC, but I also ship frost-your-own cuppies outside of NYC. I put the frosting in a separate container.

Recently, I got my hands on those puppies. Oh, I mean Cuppies. I enjoyed the sweet surprise of a cookie that was hidden inside the cupcake. My favorite was King of Fluff because you could taste the fresh banana and real peanut butter topped with a light and fluffy marshmallow frosting. It was a sweet surprise.