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When eaters realize that the apron-clad woman standing beside cups of vegan jambalaya, shrimp gumbo, and mixed berry cobblers is the Sandra Dailey of Sandi’s Cobbler Cups, they go a little crazy. “I felt like a celebrity,” she said of one recent corporate catering event in Silicon Valley. “Everyone wanted pictures with me in front of the food. That’s what keeps me doing what I’m doing.”

Sandra Dailey isn’t in the catering business to make mounds of money. She’s in to make people happy. So she attends practically every event she caters.

She caters for politicians, for massive jazz festivals, and at Levi’s stadium in Santa Clara, where the San Francisco 49ers play. Every Friday, she delivers meals to 45 homebound seniors, too. And, of course, Sandi’s Cobbler Cups does corporate events, too.

“You know what I love most of all?” Dailey said. “Instant gratification. I love seeing people taste my food. I know that my flavors are beyond something they’ve ever had before. That’s the joy of catering—it’s to watch people eat.”

Sandra Dailey and Sandi’s Cobbler Cups catering.

She learned how to cook large volumes of Southern and Cajun dishes from her grandmother, cooking together for their large family and up to 75 people every Sunday. In adulthood, Dailey catered as a hobby, learning through a food-handling class how to transport and best keep food at temperature. But retiring from thirty years in biotech sales—where her team ordered catering to entice potential clients—led her to the idea that would become Sandi’s Cobbler Cups.

Her friend had an apricot tree overloaded with fruit. Dailey knew that if she were to create a catering product around the apricots, it would need to be portable. Because event attendees—whether at a festival or office event—need to easily socialize. She wanted a niche product she could produce for a reasonable cost. One that would catch on in popularity and help her grow in the long-term—the catering scene in San Francisco was already saturated with talent, and she had to stand out. “I had an epiphany,” she said. “Apricot cobbler! Then, cobbler in a cup!”

Sandra Dailey and Sandi’s Cobbler Cups catering.

Sandra Dailey founded Sandi’s Cobbler Cups in 2012. “I think it’s very important that you talk to people—I am a very social person,” she said of then positioning herself at community events outside of the catering world. She tapped into her church community, non-profit events, her biotech sales contacts, festivals, and local boards she served on, like those involved in the upcoming vote for the San Marino stadium.

Actively engaging in her community came first. Feeding that community, second. “The first few years I wasn’t into making money. It was about meeting people, starting with a niche product, and watching them enjoy it,” she said of the many free tastings she did to market her product.

It worked. As her event calendar filled, she started adding more cobbler flavors to her menu. She added savory dishes to tastings. When something took off—like her recent macaroni and cheese in a cup—it would go on her permanent catering menu.

Sandra Dailey and Sandi’s Cobbler Cups catering.

“It’s not about the money,” Dailey said. In fact, she turns down large events for over two-hundred people, to keep her team small. She doesn’t lose money, either. She knows her food costs down to salt quantities and knows what she can and cannot cook for custom menus. “It’s about the ability to say ‘yes’ or ‘no.’ To control my growth. And to be creative,” she said about keeping her business ambitions in line with long-term ambition.

That’s the advice she gives to younger entrepreneurs. Because, yes—Sandra Dailey has seen tremendous growth: this year, the Silicon Valley Voice reports she’ll have her own Sandi’s Cobbler Cups stand at the San Marino stadium and will be one of many prestigious chefs in an upcoming event with the nonprofit Hunger at Home. But those came because of long-term investment in her community, being social, and standing beside those trays of cobbler-in-a-cup.

“Do you know what it’s like to look at a person’s face when they taste that food? Ah! That’s it, for me,” she said.

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Jacqueline Raposo

Written by:

Jacqueline Raposo

Jacqueline Raposo is an expert interviewer. Her over 400 articles, essays, and podcast episodes feature Missy Robbins, Daniel Boulud, Alex Guarnaschelli, Marcus Samuelsson, and other such award-winning chefs, restaurateurs, sommeliers, managers, and hospitality personnel. Find her at www.jacquelineraposo.com or as @wordsfoodart.

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Tagged with: American, Caterer Network, Job Success, Management, Marketing, San Francisco, Southern, Treats