Cupcake Charlie's/VisitingNewEngland small business partnership - Local Small Business Stories
The Sweet Story of Cupcake Charlie's
How this local small business started from scratch to
quickly become the best cupcakes destination in Massachusetts and Rhode
Island
Chocolate Raspberry Surprise cupcake from Cupcake Charlie's in Falmouth.
Article and photos, unless otherwise noted, by Eric Hurwitz.
Article
updated on 7/25/2018.
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On a hot mid-June day in Falmouth, Mass., tourists start to gather in
crowds on Main St. as a preview to the Cape Cod summer vacation season.
The big storefront windows at one of New England's nicest Main Streets
reveal a healthy number of restaurant customers and retail shoppers
inside, but none as busy, at the moment, as Cupcake Charlie's.
The small shop with the happy Cupcake Charlie's cartoon mascot store
sign, pink, white and blue awning, sweet aromas, old-fashioned
tiles floors, pink chairs, retro hanging lights, colorful cupcake
display case and sunny, open kitchen looks like something out of a
happy 1940s movie scene portraying the classic small town American Main
Street USA mom and pop business.
Lining up for cupcakes and other baked goods at Cupcake
Charlie's in Falmouth.
It's a place where little kids eyes'
automatically widen at the sight of yummy sweets and
mouths get covered with frosting. Adults go against the "No dessert
unless you eat your dinner" warning and instead take on the "When in
Rome..." mantra by unhesitatingly following the eating habits of their
children.
Enjoying a Fourth of July cupcake at Cupcake Charlie's. Photo
credit; Cupcake Charlie's.
Beyond the counter, a sign that states "Life is Short...Eat a Cupcake"
appears to
reflect real life, as customers order these tasty
small cakes as if there was no tomorrow. The thing is, there was
supposed to be "no tomorrow" a few years back as the cupcake craze
found the icing coming off the cake with many businesses closing --
similar to the once popular frozen yogurt trend. The cupcake, dating
back to 1796,
and given a new life courtesy of Carrie and Miranda devouring vanilla
cupcakes with pink frosting outside Magnolia's Bakery in New York City
on the classic Sex and The City
episode, somehow lost its way in the business world. Part of the
problem: Business owners took on a one-note mission to sell just
cupcakes in locations that couldn't support such stores in small
downtowns and cities with high rents exceeding the cost of operations.
Fortunately, someone forgot to send Cupcake Charlie's the "cupcake
craze is over" memo. Penny and Dan Lessa, husband and wife and owners
of Cupcake Charlie's,
got off to a spectacular small business start not too long after first
opening their business. The Food Network's Cupcake Wars
recruited Cupcake Charlie's in 2010 to team up against other cupcake
shops across the country. Penny and nephew Mike Centamore (who runs the
Plymouth Cupcake Charlie's) appeared on the show. Although they didn't
win,
Cupcake Charlie's made it to the end of the competition with, along the
way, celebrity
host Duff Goodman "bowled over by Charlie's Samoa Chocolate Cupcake
with caramel and coconut."
Reality check: Cupcakes never really went away. They just returned to
mom, grandma and auntie's kitchen, at elementary school birthday
parties and family outings. Penny and Dan, however, knew that they
could make a go at their new found passion in the form of a business by
making high quality cupcakes in a warm and inviting place that cupcake
lovers could call
a second home. The Lessas, Stoughton, Mass., natives with backgrounds
in Florida real estate, intuitively realized the value of "location,
location, location," and expanded beyond the success of its first shop
that started in 2008 at the Mashpee Commons in Mashpee (Cape Cod).
Within a few
years, Cupcake Charlie's also opened by the Plymouth waterfront in
Plymouth, Mass., in the heart of famous Newport, R.I., known for its
mansions and ocean, at the world-class Patriot Place dining, shopping
and entertainment complex at Gillette Stadium in Foxborough, Mass.
(home
to the New England Patriots), and popular Main Street in Falmouth.
Interesting side note: Rob Ninkovich, the former New England Patriots
outside linebacker star, is a big Cupcake Charlie's fan -- the
Lessas created a "Twixovich" cupcake (with Twix candy) for him and
customers. The Lessas even made a "TB12" cupcake for Tom Brady
with avocado, zucchini and spices, knowing his healthful ways (for the
record, it is not known whether Mr. Brady tried the cupcake).
Out front at Cupcake Charlie's in Falmouth.
"We are trying to evolve without losing the main interest in cupcakes,"
said Penny. "Cupcakes are not the 'thing' right now, so it is important
to figure out how to stay in business. We have done well. The cupcake
is just one product. We needed to do more. We needed to be where people
are. If you rely just on a residential area, it is often not going to
work. Look at how many stores like that had to close."
Initially, the then-troubled real estate market forced the Lessas to
rethink
careers, but they had no fear delving into an unfamiliar career field.
The couple found out, fortunately, that locals couldn't get
enough of the cupcake recipes they created, so they took that formerly
untapped talent to opening the Mashpee location. Dan, who also
possesses a
background in art and laying out floors, designed the colorful, well
laid-out upbeat stores that are as welcoming as the presence of
cupcakes.
"People thought we were crazy wanting to open a cupcake shop, but we
ran with it from the beginning," said Penny. "It is more than a mom and
pop shop. We have the Cupcake Charlie character that made us more
identifiable. We have great customer service and amazing products. That
combination is not always common."
Display case with Vanilla luvs Chocolate and Lemon Drop cupcakes.
They hired well. The Lessas have painstakingly found top performing
employees at each store who believe in the Cupcake Charlie's concept
and can work consistently at a highly efficient level. Centamore
and his wife Katie moved from South Carolina to manage the Plymouth
location. At the Falmouth store, Molly Henderson -- a 2017 Upper Cape
Cod Vocational Tech School graduate -- serves as the assistant
manager. She works at a professional level well beyond her years
exhibiting superb customer relations skills, the ability to take on
multiple tasks at the same time and carry on a pleasant, happy
personality through the busier times. When customers walk into the
store, Molly instantly and sincerely greets them in a way that makes
them want to stay.
"Penny and I went out to eat one night at a restaurant and Molly was
working there," said Dan. "We were thinking 'She needs to work for us.'
We were so impressed with the way she was working. We are really glad
to have her working for us instead!"
Added Molly, "I love working at a place that makes people happy. I love
it here. Everyone comes in here happy. It is very uplifting."
Molly Henderson makes a shake at Cupcake Charlie's.
While the Lessas have made shrewd real estate location decisions, used
clever
marketing campaigns (like the memorable mascot and impressive social
media outreach) and benefitted from the Cupcake Wars exposure, the bottom
line remains that they
couldn't have succeeded without quality products and the vision to
expand beyond just cupcakes (more on that shortly). Penny said
that while all locations
enjoy seeing many customers, the Falmouth location allows her a "little
bit more time" to envision, create and produce cupcakes clearly made
with love. Penny can be seen in the kitchen intensely making
cupcakes, yet she finds the time to authentically mingle with the
regular and new customers.
Penny Lessa creates cupcakes at Cupcake Charlie's.
"We bake fresh every morning at all locations," said Penny. "The bigger
bakeries, they
just make things and then freeze. We make things in small batches. I
think the customers appreciate the fresh products and the consistency."
Chocolate mint madness cupcake from Cupcake Charlie's.
More than 100 different flavors can be found, at any time of the year,
at Cupcake Charlie's (many seasonal flavors), but you'll always see 16
fresh-baked, handmade
cupcake flavors in the
display case on a daily basis. These "dailies" include Grammy's Carrot
Cup, Chocolate luvs Vanilla, Lemon Drop, Hostess with the Mostess
(Cupcake Charlie's delicious version of the Hostress Cupcake), Vanilla
luvs Chocolate, Oreo Delight, Rockin' Red Velvet, Peanut Butter
Pleasure, Orange Dreamsicle, Chocolate Overload, Funfetti, Vanilla luvs
Vanilla, Charlie's Chocolate Chip, Chocolate Mint Madness and Chocolate
Raspberry Surprise.
Hostess with the Mostess cupcakes from Cupcake Charlie's.
The sweet fun doesn't end there, however. Cookies, trifle cups, push
and cake pops, cake cups and jars, cookies, whoopie pies, shakes and
soft serve ice cream (including "Cupcake Whirlies" that combine a
cupcake flavor with the ice cream) and more baked goods and frozen
treats create more tempting options that make
it more difficult to choose amongst the many masterpieces.
Whirlies soft serve ice cream with red velvet cupcake pieces
from Cupcake Charlies. Photo credit: Cupcake Charlie's.
Homemade whoopie pies from Cupcake Charlie's.
Cupcake Charlie's also makes full-sized cakes -- perfect for weddings
and other special events and ceremonies -- as well as gluten free items
that Penny said taste like the "real thing."
Gluten free carrot cake from Cupcake Charlie's.
"We are definitely foodies," said Penny. "We appreciate anything that
tastes good. We just don't want to make cupcakes. We make them until we
can't make them any better. It's all about the flavor combinations and
the thought that is put into making each cupcake."
Web site for Cupcake Charlie's: http://www.cupcakecharlies.com
Facebook fan page: http://www.facebook.com/CupcakeCharlies
Twitter page: http://www.twitter.com/cupcakecharlies
Cupcake Charlie's Locations
FALMOUTH, MA
Historic Downtown Falmouth
153 Main Street
Falmouth, MA 02540
Phone: 508-540-2253
Sunday 11:00am - 9:00pm
Monday 11:00am - 9:00pm
Friday & Saturday 11:00am -
10:00pm
PLYMOUTH, MA
6 Town Wharf, Plymouth Waterfront
Plymouth, MA 02360
Phone: 508-747-9225
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm
MASHPEE, MA
10 Central Square, Mashpee Commons
Mashpee, MA 02649
Phone: 508-477-2253
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm
FOXBOROUGH, MA
262 Patriot Place
Foxborough, MA 02035
Phone: 508-698-2253
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm
NEWPORT, RI
Located on Thames Street in the Brick Market Place
135 Swinburne Row, Brick Market Place
Newport, RI 02840
Phone: 401-848-2253
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm
Cupcake Charlie's sign in Falmouth.
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