Sibby Thomsen – Maker of Cupcake Magic

June 7, 2023
Sibby Thompsen of Sibby's Cupcakes

Author’s Note:

I live in San Mateo, California, a couple of miles away from Sibby’s Cupcakery. Whenever I am at an event, or even when I host my own special gatherings, I know that Sibby’s will be part of the event. This is such a special place, and everyone around the city agrees. We have our own local batch of heaven. So, one of the people I have wanted to interview for a long time is the owner of Sibby’s. I had met her years ago when I happened to come in for an order. I had the chance to gush in person. When I got to interview her, it was one of the most fascinating experiences. Her story was one I was really vested in. And I am so happy to share it here with you. Meet Sibby Thomsen.

Passion Finds the Way

If you start thinking of the world as your cheerleader, not your challenger, fate will bless your path.

Sibby Thomsen models this perspective, and creating Sibby’s Cupcakery has required an optimistic outlook. Building a business from scratch is tough – especially a niche bakery. This may be why many women look to Sibby’s story as an inspiration to follow their dreams. Nearly 20 years since it opened, and now with 30 people on her team creating cupcakes for weddings, birthday parties, corporate events, and everything in between, her business is a must-visit for cupcake lovers in the Bay Area.

“I knew my purpose in life was to do something that makes people happy. And I always had a passion for baking. I loved the creativity and craft of baking – making something tangible and delicious, and the joy that came from sharing it with others.”

Sibby’s Entrepreneurial Roots

The first person who inspired Sibby to bake was her mother. She remembers flavors bursting from her mom’s blueberry-peach, apple, and chocolate pies, as well as the beautifully browned, flakey crusts.

Sibby grew up in Topeka, Kansas, in a close-knit community along with her two sisters. She helped her mother bake all kinds of delightful treats like caramel brownies, birthday cakes, lemon bars and Hello Dollies. She would add her own creative flair to the desserts as well.

At home, “following one’s bliss” was encouraged. Her dad, a businessman, regularly traveled for work and sometimes brought the family along. He never stopped Sibby from visiting bakeries during these trips.

“The first thing I would want to do on our family trips was find the local bakery. I loved getting cupcakes from those bakeries because they would have cute plastic decorations on top with cartoon characters. But at that young age, I never thought about owning a bakery.”

Education and Work Prior to the Cupcakery

After high school, Sibby attended Northwestern University, where she majored in American Culture. Her studies focused on Art History and the Civil Rights Movement, and her thesis was on the art of the Black Panther Party. For research, she tracked down and interviewed Emory Douglas, the former Minister of Culture and primary graphic artist of the Black Panther Party.

One summer during college, Sibby worked as an intern for an advertising agency in Kansas City. She enjoyed her experience, and after graduating, began a career in advertising at Leo Burnett in Chicago. A co-worker at Leo Burnett first introduced her to technical cake decorating.

“I worked with a woman named Katie, whose grandmother had taught her how to decorate cakes, the old-fashioned way, with a piped border around the top and bottom of the cake, and with clowns made from buttercream on the top. She was the first person who taught me how to use proper piping bags and decorating tips.”

Sibby had loved taking art classes and making paintings as a child and this opened a new avenue for expressing her creativity.

In search of better weather, Sibby took her advertising career to San Francisco, where she worked as a Vice President of Account Management. But after almost 10 years in the industry, she began to notice how much joy she got from baking cakes and cupcakes for her colleagues and clients. She came to the realization that her true passion was baking – and she decided to explore doing it professionally. 

Finding Her First Bakery Job Meant Founding Her Own Bakery

Sibby’s demanding job in advertising left little free time for entrepreneurialism. So, to nourish her passion for baking, she shifted to a 3-day workweek, thanks to an understanding and supportive manager. 

“I wanted to work in a bakery one or two of those days, and no one would hire me because I had no experience. Finally, I realized that if I was going to do this, I needed to dive in headfirst and start a business.”

Sibby has been a part of a monthly women’s group for over 20 years. Members of the group support each other in their personal and professional lives. After learning about Sibby’s bakery aspirations, one of her friends in the group provided the spark she needed to get started. Her friend knew the hosts of a popular shopping event in San Francisco called Appel & Frank. Unbeknownst to Sibby, she informed the hosts that Sibby would like to have a booth at the event. At the time, Sibby did not have business cards or a business name, but she had recipes that she had spent months perfecting. The pressure to get ready for the event forced her to get the basics together, and her cupcakes were an instant hit! She sold hundreds of cupcakes for attendees to sample and booked her first wedding and several events that night. 

In 2004, she had the only business focused solely on cupcakes in the Bay Area, so word traveled fast, and Sibby’s Cupcakery began getting recognition. Even Sibby, who describes herself as risk-averse, was ready to leave her advertising job.

“My husband was in grad school. We moved from the city to Palo Alto, and our parents were like, ‘What are you doing? You just quit your job when your husband’s in grad school?’ But after years of dreaming about making a change, I was ready to take the leap towards my passion.”

Enthusiastic Learner = Enthusiastic Baker

The evolution and growth of Sibby’s Cupcakery is a result of Sibby’s enthusiasm for learning and experimenting. Early inspiration came from reading cookbooks, tasting unique flavor combinations at ice cream and chocolate shops, restaurants, and farmers markets, or attending industry trade shows like the Fancy Food Show.

“Baking is an amalgam of art and science, but I learned the science component—like the basics of how a cake rises—by trial and error. I would read books explaining the impact of baking soda versus baking powder, but I rarely fully grasped the concept until I tried it out and failed on my own.”

The cupcakery bakes 20 regular flavors (including a gluten-free assortment) and a rotating selection of flavors of the month daily. They’ve sold 150 flavors over the years – all nut-free and many developed over long periods of trial and error. Sibby and her staff continue to relentlessly test, improve and invent new flavors – like Midnight Magic, Tuxedo Butter Cup, and Java Chip, all popular recent additions. At the peak of the unicorn craze, Sibby’s team created a Magical Unicorn Cake made with the top-secret ingredient “unicorn milk.”

Running a Bakery is a Team Sport

When she first got started, Sibby was doing all the baking, decorating, customer service and delivering on her own. Some early good press led to fast growth, and the phone began to ring off the hook. The Daily Candy – a popular email newsletter providing readers with tips on hot new businesses – featured Sibby’s Cupcakery in their Best of the Year issue. “That really kicked things up another notch, and then I knew I had to get a commercial space,” Sibby recalls.

It took almost a year to find and remodel a space for her bakery (the same downtown San Mateo, Calif., space she’s in today). She soon realized she needed help and hired her first employees. Sibby is grateful to her “bakery family,” the team of talented bakers, decorators, customer service associates, bakery assistants, delivery drivers, and facility managers who work hard every day to serve customers. 

“Without my amazing team, there would be no Sibby’s Cupcakery. Every person on our team is critical to our success. We work hard to build a community where people can have fun while doing great work. A happy team is just as important as keeping our customers happy.”

Sibby’s Cupcakery employs both culinary school graduates and artists without cake decorating experience. They also hire self-taught bakers with no prior professional experience. Sibby says the diverse and unique learning styles and skill sets elevate the team overall.

“While we have a signature style, all our decorations are hand-piped, so by nature, no two orders are identical. For our Signature and Classic designs, our goal is to maintain consistency, but for custom decoration requests, we have more creative freedom. We always leave room for creativity and new ideas, growth, and improvement. Maintaining excellence and accuracy is key.”

Motivation for Business Growth Comes from the Heart

The mission of Sibby’s Cupcakery is to create joy and happiness for its customers and community through delicious and beautiful old-fashioned cupcakes and exceptional customer service. But Sibby does not believe that growth is the primary ingredient to fulfilling the mission. Instead, her approach to how she makes decisions for her business is more aligned with the Japanese philosophy, ikigai, which emphasizes creating a purposeful life by combining your passions, talents, and profession with what your community needs. She strives to do this while enjoying the present moment and staying true to her vision for the bakery. 

“I don’t like the question, ‘Where do you see yourself in five or ten years?’ I think growth is important, but growth isn’t always the most important thing. The pandemic reminded us of that – during COVID, we were forced to be rooted in the present. Every day we’d be thrown a new curveball. There was no thinking about the future back then, just figuring out how to answer the question: ‘How will we survive today?’ We had to rethink our operations and staffing needs so that we could respond effectively to the new challenges.”

Sibby isn’t motivated to open multiple locations or franchise her business. Instead, she remains committed to her original vision – to create a unique “mom-and-pop” shop like the one-of-a-kind spots that have inspired her throughout her life. She remains motivated by her team and the bakery culture and community they’ve created. 

“I love being in the bakery. What’s not to love about bringing joy to people while being creative and listening to great music, and laughing? I always look forward to coming to the bakery, even if that means waking up at the crack of dawn.”

Handling Business Stresses

Like any small business, Sibby’s Cupcakery has experienced challenging times, especially during the pandemic. Wearing masks posed unique challenges to customers. It became harder to convey friendliness, and communication was difficult. 

Ongoing supply issues meant that sometimes the bakery couldn’t get certain ingredients or their preferred brands, which forced them to get creative and improvise. For example, an accidental delivery of 40 pounds of oranges – instead of lemons – led to an unexpected new flavor, Chocolate Orange Blast! 

“When inevitable challenges arise, I try to find the silver lining. Of course, it’s easier said than done, but I strive to see setbacks as invitations to learn, grow and improve.” 

The pandemic also meant that most weddings and corporate orders were canceled. Sibby’s adapted by getting creative and keeping their customers engaged. They created seasonal decorating kits for holidays such as Valentine’s Day, Easter, Halloween, and Christmas, plus a popular Magical Unicorn decorating kit. They also developed fun-themed samplers that each introduced six new flavors. The “Box of Chocolates” Sampler in February is an annual favorite. The Ice Cream Sampler included cupcakes inspired by ice cream flavors like Cookies & Cream, Mint Chocolate Chip, and That’s-That (modeled after the San Francisco ice cream treat, It’s-It). The Cookie Sampler featured a Circus Animal cupcake (with house-made animal cookies on top), Raspberry Thumbprint and Biscoff, among others. And to further stay connected with customers, they started doing a monthly Sibby’s Sampler giveaway to followers on social media.

To the Future Bakers and Future Entrepreneurs

Sibby has a few pieces of advice for future bakers and entrepreneurs:

“Do your homework. And trust your gut. Be realistic about the grit and hard work that’s necessary to start a business. Go in with your eyes wide open. There will be aspects of any job – including the one you create – that you won’t necessarily like. That’s OK. Focus on the positive—the parts that you love—and sink into that.”

“Working in the business is the fun part, but working on the business is what sustains it. Make time for maintenance. Filing, archiving, labeling/organizing digital files, whatever maintenance means for your business. It’s never urgent, but when you urgently need to find something, you will be grateful. Just like you’ve got to water a plant regularly to keep it healthy, you’ve got to tend to your business to do the same.”

“Don’t let data snuff out your intuition. Try things, experiment, and collaborate with your team. Be open to ideas and change. Take calculated risks and go for it. Set an intention and visualize it. Have a plan and a timeline – nothing gets done without both. Be clear about your goals and mission, and stay focused on your vision.”

“Follow your bliss. You will still work your butt off, but there is a sense of satisfaction that comes from doing what you love and what you feel you’re meant to do. It will feel scary, but following your passion is so worth it!”