Words by Kate Lucky
We’ve all been to this wedding: The one with the towering cake, covered in buttercream and fondant decorations. How could something so impressive not be delectable? But one disappointing bite tells the truth: That cake is dry.
Appearances deceive the other way, too. A lemon bundt that sticks to the pan, a lumpy cookie with a too-browned bottom. Visual disappointments, yes. Tasty? Also yes.
It’s a special bakery that manages both aesthetic delight and mouthwatering flavor. Sibby’s Cupcakery, a tiny, pink shop with a flower-filled window box located along the San Mateo railroad tracks, is one of them. Owner Sibby Ross Thomson runs her shop collaboratively, working with her staff to continually create new flavors, decorations and themes. “Good ideas can come from anywhere,” she declares. Her staff experiments with guava and strawberries, chocolate and cereal, sharing feedback in monthly taste tests. The cupcakes (mini, regular and jumbo, all nut-free) are moist and flavorful, with a just-right ratio of frosting to cake.
And they’re lovely: cinnamon-spiced carrot cake with tiny orange frosting veggies, yellow lemon-drops garnished with a jelly bean, airy chocolate flecked with skinny sprinkles. The special orders are whimsical: mummies for Halloween, flip-flops for summer, waffles and starfish, lavender sprigs and crayons. Tiny chickens for a family naming the members of their new coop. Even 666-themed cupcakes, covered in flames and devil horns, for a family with triplets: All boys. All turning six. “Our decorators are artists,” Sibby says proudly. “You have someone who might be an expert in roses, and someone else who loves doing characters.”
Sometimes, decorations are conceived in tandem with new flavors. Take the shop’s County Fair box: caramel corn popcorn, funnel cake, blueberry pie, cotton candy, churro and strawberry lemonade. Or its Ice Cream selection: orange creamsicle, strawberry shortcake bars. The That’s That, a play on the San Francisco classic It’s-It, combines oatmeal cake with vanilla buttercream frosting dipped in ganache. Yum.
It’s no surprise to learn that Sibby has a creative background. She started baking as a child in Kansas, helping her mom make blackberry, peach and apple pies. At college in Chicago, she studied art history and the civil rights movement; it was a thesis on the art of the Black Panther Party that brought her to Berkeley for research. “I loved it out here,” she reminisces. And so, after a couple of years of advertising work in Chicago, she uprooted for San Francisco. After marrying her husband, a Palo Altan she’d met in school, Sibby knew she was here to stay in the Bay. Continuing in advertising, she contributed to the creative process for brands for a decade—but longed to make something all her own.
“During that time, I was still baking. I would pull all-nighters, baking cakes and cupcakes for my clients and team,” Sibby recounts. Baking “was really my passion,” she realized, and fitting it around a corporate job was unsustainable. There was only one thing to do: Quit her full-time job, and start her own shop.
Cupcakes seemed manageable. She’d only need one pan size. Sibby baked from home, until glowing press and word-of-mouth crowded her kitchen with orders. The San Mateo storefront was the solution to the bakery’s popularity. “When I first moved into this space, it felt even more off the beaten path,” she says. “There were literal tumbleweeds… I felt like I was in Kansas.” She relied on delivery in an era when “you could really only get pizza and flowers delivered.”
Now, almost 20 years later, a yoga studio and a ramen restaurant have moved in down the street, and the shop gets plenty of walk-in customers. After her start as a baking, decorating and delivering solo act, Sibby’s staff has grown to 30 and her shop has been touted as “the cupcake center of the universe” by press. For a few years, the bakery served as the designated cupcake provider for the 49ers. They’ve baked for Google, Yahoo and Twitter.
Times have changed since those early days of mixing batter and answering phones from home. But Sibby’s inspiration remains the same. “It really is a privilege to be part of people’s celebrations,” she reflects. “We might be doing 12 baby showers that day, but everyone understands how important each specific event is.” She laughs, “We’re not in this business, in any capacity, to make money… We’re in it because we have a passion for making people happy.”
On this sunny weekday, a few employees cheerfully pack orders in pink boxes adorned with bows. Sitting in the bakery’s small kitchen, Sibby speaks not just about the community she tries to build among her employees and customers, but in the region at large. For 20 years, she’s been involved with Baker’s Dozen, a San Francisco collective of professional and home bakers who swap ideas about everything from collapsing angel food cakes to gluten-free techniques. Some are technically “competitors,” but the group is generous with their time and tips. “That feels like the Bay Area to me. I’ve never been part of a group like that,” Sibby notes.
Sibby’s Cupcakery doesn’t advertise; instead, they give back, and know that their neighbors will notice. They partner with Sol Mateo, a mental health nonprofit, and donate to school auctions. At the end of the day, they give leftover cupcakes to organizations like LifeMoves, Samaritan House and Peninsula Food Runners. And sometimes, Sibby’s bakes something new for a cause. After the death of George Floyd, the bakery released the Midnight Magic, layers of chocolate cake with chocolate mousse filling and fudgy frosting, dipped in ganache and sprinkled with homemade Oreo cookie crumble. All proceeds went to organizations like the Equal Justice Initiative.
Sibby’s generosity extends to individuals, too. A friend’s dad, suffering from Alzheimer’s, couldn’t remember much. But he could remember that Midnight Magic cupcake. “So we’d make it for him. He’d be sick and our bakers would say, ‘100%! We’re making it.’”
Delectable to eat, delightful to look at: a rare combination. Even rarer: baking a difference along the way.