The Cape is going Cuckoo for Cupcakes!

Cupcake Charlie's is an award winning Cupcake bakery, with two locations on Cape Cod- and more scattered around New England. One located in the heart of Mashpee Commons, and the second being in Falmouth. To us Cape natives, a visit to Cupcake Charlie's not only brought us so much excitement, but it also allowed us to make so many fun and sweetly filled memories. To those of you who are traveling to the Cape on a vacation, this has to be one of the most important destinations that you absolutely MUST visit. From Cupcakes, to Frosting Shots, to Trifles, there is bound to be something your sweet tooth will dance for joy about. 

​This week, I had the privilege of speaking with Penny Lessa, the woman that makes all the magic happen. Penny takes Pride in her bakeries, and no two items are ever alike. The quality of her work is extremely important to her, especially when it comes to pleasing her loyal customers.

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​1.) Prior to Cupcake Charlie's what type of industry were you involved in?

​"Prior to Cupcake Charlie's I was in the Real Estate business. I was a licensed agent and was living 10 months out of each year in Florida, in the Disney area. I specialized in the sale of vacation homes, and investment properties. The market, at the time was very strong, and I met with great success.
I was also licensed in MA - getting my start from another wonderful female entrepreneur here on the Cape, who has been a successful agent for years!  Before all that, I was working as a Sales and Marketing Director at a wonderful Assisted Living Community here on the Cape"

2.) Did you undergo certain education or training to have knowledge in the culinary (or baking?) field?

​"I have no formal training or background in the baking industry. I am completely self taught, (with the help of my Mom and some old neighbors) and have had a love of baking since I was a kid. My Mom used to make stunning cakes out of our home when I was growing up - and I remember hoping she would have left over frosting so we could eat it on crackers when she was done. (you should try it sometime - it's DELISH!)  It took almost a year to perfect all the recipes for Cupcakes Charlie's, and then learning how to actually operate the business, was one day at a time, once we opened the first shop."

3.) What sparked your interest in opening up your own business, let alone, a dessert business!

​"I am definitely an entrepreneur at heart. I had tried my had at a few business in the past - but none lasted long term. You know that question . . . "If you can do any type of work, what would it be?" Well my heart always said own a bakery - but not being formally trained made the thought of that overwhelming.  But, once the real estate market crashed, and I had to decide what was next for me - I decided cupcakes!! (with a bit of encouragement from some special family members!) My husband looked up cupcakes online and saw that a few shops actually already existed in CA, NY and Las Vegas  - so immediately I felt it was a risk worth taking!"

4.) How long have you been in this business? 

​"We just recently celebrated 10 years in business! Boy how time flies. I feel so blessed to have made it this long. In those 10 years the business has grown to 5 shops. There are 2 on the Cape (Mashpee Commons and downtown Falmouth), one in Plymouth, down on the waterfront, one in Patriot Place in Foxboro (home to the New England Patriots) and one in Newport, RI.  We have evolved over these 10 years from just cupcakes - to now offering custom cakes, whoopie pies, butter bars, cake pops, frosting shots, trifles, cookies, Gluten free and Vegan products, amazing soft-serve ice cream, and more. We even offer Nationwide shipping, which is a great option for the tourists that live far away to get their cupcake fix. I love baking - so often, when I am in the shops, I love to experiment - so you never know what I might whip up and put in the bakery case . . . most recently, mini key lime pies - YUM!"

5.) Why Cape Cod? Have you lived here your entire life? Or were you just looking to relocate.

​"The location was a hard decision. We were still living 10 months in FL, and 2 months here on the Cape. But in the end, I really felt the support of family was needed (and all my family is in MA). We live on the Cape, so a location here certainly made sense. I felt like foot traffic was going to be important to the success of the business - so that is what drew us to the Mashpee Commons - and it has turned out to be a great decision."

6.) What do you prioritize most when it comes to creating the actual products in store?

​"Flavor is of the utmost importance. I definitely consider myself a Foodie, and feel like I know what tastes good. So I won't stop until I think a product tastes absolutely as good as it can. That is so important to the success of keeping long term customers. They can recognize good quality and good flavor, and they appreciate it! After flavor is the design. It has to look good too, to catch a persons eye - If it doesn't look appealing, or fun or creative, then people just won't buy it."

7.) What would you say is your biggest success thus far?

​"My biggest personal success thus far has been choosing the right husband. Having a good man that builds you up, encourages you and helps you follow your dreams is really one of the keys to a happy life - I am Blessed to have found a wonderful man! After that is Cupcake Charlie's of course. I am so proud of how it has grown and am always amazed when I meet a person for the first time, near or far and they actually know about Cupcake Charlie's. It is an amazing feeling! We were on the beach in FL one time and got to chatting with some people - and they actually knew of us - its crazy sometimes."

8.) What would you say is your biggest weakness?

​"My biggest weakness is being a perfectionist - the worry of not being perfect, or failing at something new, can sometimes hold me back - or take me 3 times as long to do, because I want total perfection."

9.) Could you ever expand past the Cape and Plymouth (south shore) area? Would you want to if so?

​"We could certainly expand. I have a shop in Newport, RI - that is a little over an hour away. But the further you get, the harder it is to manage. And I never want to lose the quality of product or the original vision. I really don't want to disappoint any customers."

10.) What's your favorite part about the business? Do you have a "favorite" product?

​"Choosing a favorite product is tough. I am a sweet-a-holic - so I pretty much enjoy it all. If I had to choose a favorite cupcake - I would say either our hostess with the mostess or our Cream Puff - both soooooo good!! My favorite part of the business is getting to be creative. I love coming up with new products or new flavors - it is so fun to experiment!! And if it makes it into the case - I LOVE when it makes a customer happy - so satisfying!"

11.) What goes into the planning and creating of new flavors, ideas or styles? Are they produced often? 

​"A lot of times, creating something new just comes on a whim. The mood for experimenting strikes, and off we go . . . Other times, it is based around a holiday of some sort. For example, August is National Peach Month - so I have spent a couple of weeks trying to perfect a NEW Peach Crisp cupcake. This new flavor will be released in shops on Aug 22nd, which is Nation Eat a Peach day."

12.) Do you have any advice for future entrepreneurs in hopes of starting their own businesses?

"I would say that if you are looking to venture out and open your own business - be sure to choose something you love to do and are passionate about - as it will become a huge part of your life, so you are going to want to enjoy it! And be sure to do whatever it is - the best it can possibly be done. You want to be the front-runner. Treat your staff with respect, and let them know you appreciate them. Build them up and mentor them - And treat your customers like gold! You have to know and always remember, that without customers, you will have no business -"

​Already visited? Tell us YOUR favorite Cupcake in the comments below!

As Always,
Alayna Anderson
​Editorial Contributor and Marketing Specialist 

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