Let’s say you are a young Midwestern couple who decides to move to Santa Barbara, after a few Chicago polar vortexes too many, to raise your family and put down some roots. What are the odds that you will also create and produce a new brand of wine?

Ninety percent of all American wine is produced in California. About one-third of those wineries are family-owned. The state has a population of 38.9 million and 2,843 registered wineries. Those are unlikely odds, yet for Carolyn and Andrew Fitzgerald, both Barrington High School and Northwestern University graduates, this is the exciting new chapter in their lives.

A Future Partnership

In Santa Barbara, Carolyn says they found a very welcoming community and an outdoor paradise—where a mountain hike and dip in the ocean could be on the same day. The former marketing and advertising executive puts her skills to work with the family business, nonprofit development roles, and supporting her children’s schools, in addition to being mom to Jay and Nora. “We make sure, though, to return to Barrington to see family and keep our Midwestern values strong,” Carolyn said.

Andrew, who holds a bachelor’s degree from Northwestern, also completed his JD and MBA degrees there. He still works full time for an investment banking firm. His curiosity fuels a passion for literature and art. “He is a beautiful artist with many paintings in our home,” Carolyn said. “He loves photography and was always taking photos in high school and when traveling. Now, some of his fascinating photos become our wine labels.”

Andrew Fitzgerald and Hayden Felice, the founders of Trippers & Askers, met through their wives, Carolyn and Lucy (Firestone) who became friends through their children’s schools. Hayden hails from the East Coast and holds a degree in English Literature from Amherst College. His career includes having worked in the restaurant world out East, with an expertise in management and wine, then ending up in Los Angeles a few years ago. The pandemic caused him to rethink his future as his work hours were late, and then his restaurant closed for the time. He also had young children. “We connected through our kids, and a mutual love of wine and music,” Carolyn said of the two couples.

Hayden, who is friends with a local vintner in downtown Santa Barbara, Dave Potter of Potek Winery, learned that he had some extra production capacity. Thinking about buying some grapes to make wine, he approached Andrew with the idea of working together. “Hayden and I bonded over enjoying the same style of wine,” Andrew said. “We both prefer lower alcohol, leaner, lighter, and more delicate wines—so we talked about making our own brand of wine.”

Poetic License

The collaboration between friends invoked a playful approach to the entire project of naming the business, choosing the business model, and landing on an artful approach to presentation. The two future vintners read poetry for a full year before listing hundreds of possible names for the business, using phrases from poems and literature.

“They found ‘Trippers & Askers,’ which is a phrase from a Walt Whitman poem, and tested it with friends,” Carolyn said. “About half the people liked it, and the other half, not so much.” With that, she said, they might be on to something memorable. The name is appropriate as Trippers encapsulates the journey that would unfold for Andrew and Hayden. Askers denotes a person who is seeking answers and opinions about truth and culture. “Hayden and I started out without ever having made wine, so it’s a new journey with an incredibly steep learning curve, and we have to ask a lot of questions,” Andrew said.