Episode 41

Sibby’s Cupcakery

August 6, 2020

Sometimes it’s the small things in life that make all the difference. For Judy, it’s Sibby’s Cupcakery.

Episode Audio:


I’m Judy Gordon, and this is San Mateo Focus. As long-term residents who have raised six kids here, we thought it was high time someone shined a light on the good things in San Mateo to enrich the lives of those living here and the businesses that serve them. If you want to know the best places to eat and play, the events not to miss, and want to know how San Mateo became the crown jewel of the peninsula, tune in every Thursday and please be sure to click the ‘subscribe’ button on your favorite podcast app. Now, onto this week’s episode.    

Sibby Thomsen, of Sibby’s Cupcakery, has strong ties to San Mateo. She owns a business and lives here. I have a few personal stories that show how her actions support the local small business community. She moved her baking business onto Railroad Avenue in 2006. And frequently in her first few years of business she would show up out of the blue at the startup where I worked with a box of cupcakes for the staff to share. When we heard the message that “We’ve got Sibby’s here” the cupcakes would be devoured. She also helped our CEO hatch a plan to hand deliver her cupcakes to a potential partner in Seattle. Later, when I worked again downtown at the DSMA, I emailed Sibby and asked if she would spend some time answering questions that a future downtown business owner had about setting up a business in San Mateo. Sibby didn’t hesitate to say of course she would help. In fact, throughout our conversation last week the word community popped up several times. Sibby ‘gets’ how word of mouth works, and the San Mateo community benefits from the way she runs her business. 

Sibby started her career after college in advertising, in Chicago, at Leo Burnett. She loved advertising and continued working on different brands like Levis and SFMoma when she moved to San Francisco. But her real passion was baking cakes and cupcakes and she would stay up at night baking for clients and coworkers. She thought about opening up her own cupcake business for five years before she finally quit her job and started baking out of her home. Her early big break came when a popular website called Daily Candy featured her cupcakes. That got her an audience and she was ready to move into her own space. She landed on Railroad Avenue surrounded by auto body shops and has been there ever since. It’s funny to think of Railroad Avenue as rural but Sibby says that when she first moved her business there it felt like her native Kansas—more rural than the rest of downtown. She said that her view was of trains, telephone poles, and tumbleweeds. She loved it and says that her neighbors all care about each other and they have strong neighborhood bonds. The neighborhood has changed since she started. There is more foot traffic in the area and because of that same day sales are now a growth area for the Cupcakery. Sibby’s has always had a delivery model but her delivery area has changed since the early days when they were busy with weddings from Carmel to Healdsburg. Now she says her customer base is from Sunnyvale to San Francisco. 



Sibby’s was one of the first cupcake-only bakeries around and she’s pretty sure she was the first “Cupcakery”—she has survived many cupcake businesses that have come and gone. They celebrated their Sweet Sixteenth anniversary this year. To Sibby, cupcakes are not a fad, they are a part of the American fabric and culture. Practical and portion controlled, they remind you of your childhood and bake sales. Cupcakes will always be loved. I asked Sibby about the Sibby’s difference, and she says at their core they have stuck to her mission and vision: to bring joy and happiness to their customers and community through delicious old-fashioned cupcakes, and exceptional customer service. As a woman-owned small business, they pride themselves on their craft. They bake the old-fashioned way, baking small batches from scratch using the finest ingredients they can find—and using only ingredients you would use at home: fresh lemons for zest, real butter. They specialize in custom decorations and it’s a simple unique style, artful and fun. Her Instagram account is a mouth-watering way to appreciate all the different designs and recipes that they create. They are also a peanut and nut-free facility and have been so from the beginning. Sibby says that the business longevity and success are due to her talented and inspiring staff and loyal customers who support the business.

Sibby intentionally created a small independent business and feels that small businesses are the soul of a city. It’s what she loves about San Mateo. There are so many unique businesses and unlike other towns that have moved more to chain stores, the San Mateo community has supported the downtown shops. Many businesses have been here a long time. Sibby acknowledges that small businesses in local communities have been hit really hard. It’s a good time to remind people that they are still out there. Sibby and her family take that seriously and choose to shop and dine locally whenever they can. She wants to make sure that their favorite businesses are still here when we emerge from this time. If it feels sometimes like an indulgence it is an indulgence that feels really good because you’re supporting a local business.

As for starting up a small business, Sibby says it’s rewarding to pursue your passion. She encourages people to go in with their eyes wide open, not to be naive. Talk to as many people as you can before you go into it. A realistic vision for the owner is to see the whole picture. Finally, make space in your week to do the things that brought you into the business. Sibby loves still to bake and decorate cupcakes and makes time for that even when the endless paperwork that is required to run her business is overwhelming. There is always more to do when running your own business. Self-care is important.  

Sibby wants to make one more point, so Here’s the Deal: While you’re still encouraged to order your cupcakes a few days ahead, if you place a call you can purchase same day sample box items. Please have patience with the phone lines and leave a message. Someone will get back to you, usually within an hour. 

Okay, that’s all the time we have for this episode. Have a great week. Don’t forget to subscribe to San Mateo Focus on your favorite Podcast app. As always, if you’d like more information about the topics in today’s episode or any of our sponsors, visit sanmateofocus.com.


@sibbyscupcakery #downtownsanmateo #sanmateofocus @judygord @pradsliff #judygordon #peterradsliff @sanmateo @sanmateocounty