When Debbie Gale started the Milwaukee Cupcake Company toward the end of 2008 she began it as a hobby — something that she did “for fun.” Fast-forward three years and the company has blossomed 
into a full-blown business, keeping Gale on her toes, amidst flour, sugar and butter 
cream delights.

With a strong business background and a business degree in hand, Gale served in a corporate role for 17 years but eventually experienced the “burnout” syndrome many face and wanted to try her hand at something new.

“I was a partner in an executive search firm for 17 years, and it was extremely lucrative,” Gale says. “But I did not enjoy it, and toward the end, I hated it and felt empty. I also suffered a terrible head injury in 2004 during a taekwondo class that I was lucky to survive, and this really made me take pause to examine my life for the next four years after it happened. I slowly came to the conclusion that I did not want to waste any more time on this earth doing something I hated. I loved baking, so I started to bake.”

The Milwaukee Cupcake Company was the brainchild of Gale and a couple of friends who had teaching jobs. But when it came down to it, they were not ready to leave their teaching jobs and invest in this full time, so Gale went it alone. “I have always enjoyed baking, and have always dreamed of opening my own café and I had always visualized it being a morning place or a place for great baked goods,” she says.

So why cupcakes? As frequent travelers, Gale and her husband noticed a common theme throughout the U.S. cities they visited.

“I saw the cupcake trend emerging in cities all over the country and I started thinking that Milwaukee could really use a cupcake shop,” Gale says. “We were so behind the other cities. So I started this as a catering business, baking cupcakes for family and friends. I don’t have formal baking training. I have a business degree from UW-La Crosse.

Gale admits that one of the scariest aspects of starting the Milwaukee Cupcake Company was letting go of the cushion of a well-paid job. “I knew a startup meant no paycheck initially and this is why I did a business plan, to see if my idea was even viable,” she says. “My husband was on board immediately and encouraged me to give it a go. Once the business plan numbers showed it appeared to be feasible, I felt that I just had to try. You only have one life, right? I would have regretted forever, not trying.”

In doing the business plan Gale did a lot of demographic research with regards to the neighborhoods she was considering for her store, and she had very specific ideas about who her target audiences were.

“The Third Ward has always been in the front of my mind for this, and I was really set on trying to find a place there, especially after doing the demographic research — most of which is all available from the various business improvement districts within the city of Milwaukee. They have great statistics and reports readily available to the public,” she says.

After Gale determined her focus area, she did some forecasting based on her catering sales, and, using some modeling software she received from a consulting firm, she did some projections and the idea seemed viable.

“Once we found our home on Milwaukee Street, the next steps involved attending auctions and sales to purchase the kitchen equipment I needed, building out a retail sales spot in our space, hiring staff, finalizing the initial menus, ramping up the recipes to large batch measurements, establishing marketing plans, selecting bulk/wholesale vendors, getting IT/back office operations in order, and most importantly, securing all necessary business, city and health licenses.

“All of this was done while still managing the business as a catering business and it took up all of my free time, which I knew would happen,” Gale says. “I pretty much knew the first year was going to be the hardest I’d ever have to work, and that my life would be the shop. We were the first cupcake shop to open in the city of Milwaukee. That was my first goal, and we reached it.”

ONE STEP AT A TIME

Gale has a lot to celebrate. The business’ first year numbers have completely blown past the models and forecasting that she did for the business plan. “We are so pleased to be so profitable after just one year of being officially open as a retail establishment,” she says. “We have been received so well by the city of Milwaukee and all of our customers. It helped that I ran it as a catering business for a couple of years before opening the shop. I had many, many clients already so word travels fast.”

In the beginning, Gale offered a lot of product sampling and did a lot of cold calling. “I called on many wedding venues in the Third Ward to let them know we were moving in, as we make cupcakes for weddings almost every weekend,” she says. “I offered free delivery before the opening of my shop which really helped me build my customer base. I called all the corporate contacts I knew and discussed our catering abilities for meetings, parties and events. And I hit the bridal circuit, purchasing some targeted advertising for this audience too.”

In fact, Gale worked hard to determine her key audience segments. They include consumers — who either through foot traffic to the store or via catering purchased cupcakes for pleasure, dinners, gifts, etc., and corporate customers who order cupcakes regularly for meetings and events. They also have their wedding clientele and even a few wholesale agreements.

"We are on the catering menu for Bartolotta Catering at all of their catering venues, as well as at the Hyatt Hotel downtown; we have also made an agreement with The Lowlands Group in Milwaukee (the owners of Trocadero, Café Centraal and the Café Hollanders). They are opening a new restaurant right around the corner from us in the Third Ward; our cupcakes will be featured on their menu when they open this summer,” Gale says.

EMBRACING THE BRAND

Gale recognizes the importance of establishing a strong company brand and she strives to make her products truly shine.

“Our company and brand is all about Milwaukee,” she says. “From the beginning, I did not have aspirations to make this some cutesy, chain type place. I wanted this to become the hub in Milwaukee for cupcakes. We name our cupcakes after neighborhoods, cities, streets, landmarks and icons of Milwaukee. We source and partner from local companies, and co-brand the flavor names with them, to lift up their brands as well as my own.” Examples include the Rishi Match Green Tea cupcake made with Rishi Tea; the Stone Creek Kahlua cupcake made with Stone Creek Espresso; the Lavender Absinthe Rouge Cupcake made with Great Lakes Distillery Absinthe Rouge, etc.

“We make cupcakes in honor of Milwaukee events, special holidays, or things being celebrated in Milwaukee,” Gale says. “We also create special flavors in honor of every festival that takes place at the Summerfest grounds each summer. We are the go-to place for cupcakes in Milwaukee. Not only for leisure, but for more serious and larger events like corporate meetings and weddings.”

Gale also bakes everything in the shop from scratch, using the freshest ingredients, sourced locally whenever possible. “Baking from scratch is incredibly more time consuming, but so worth the effort,” she says. “I would not do it any other way. My bakers have established a very strong routine in the kitchen and have streamlined the batter and butter cream production as much as possible. But we will always bake from scratch; I will never let that go. It’s what makes our product great; and it’s so rare these days. It’s really important to me.”

LESSONS LEARNED

For those interested in embracing their entrepreneurial spirit and starting their own business, Gale stresses that you must do a business plan to prepare, and you must be willing to put aside a lot of your personal life the first year.

“Also I think giving back and community service is huge. Why else are we here really?  Yes, to be successful and survive ourselves, but also to give back to this great city that we live in, to the people who need it,” Gale says. As a result of this mindset, Gale and her team get involved in community efforts such as donating leftover cupcakes to a shelter, food pantry and a soup kitchen; sponsoring charity events; donating cupcakes or gift certificates to charity events; donating portions of their cupcakes sales to causes (like Susan G. Komen); and adopting a soldier in Afghanistan. “There are so many ways to give back and get involved,” she says. “Do not be afraid to try. You will regret not trying, and nobody here knows how long we will each be on this beautiful earth. Try it now, but do it smart.”

So what does the future hold for the Milwaukee Cupcake Company? Gale says there are still customers both in the city and in the suburbs who have not heard of the company or tried its sweet treats.

“I’d really like to reach as many people as we can, and continue to make people happy with our product,” Gale says. “Seeing their faces light up when they open their boxes, or see their wedding display all set up. That’s the best!” 

Photos by Corey Hengen

By Maura Keller

Maura Keller is a freelance writer originally from Wisconsin.