Spotlight on Federal Hill Businesses | Upper Chesapeake Insurance Agency

Upper Chesapeake Insurance Agency

Owners: Kathleen & David Carr

Kathleen: “Dave and I met in college and moved to Baltimore shortly after. He’s been building this business for over 25 years. When Dave initially started the agency, he started as a scratch agent, meaning he didn’t have one single customer. Literally, his first customers were probably his parents or friends.

David: “But after being in the neighborhood, you can’t help but get connected while living and working in Federal Hill. Everyone has opportunities to meet one another while we’re out and about. There are ample opportunities to connect from a business standpoint due to the flow of business that naturally takes place within the community.”

Kathleen: “In this neighborhood, people like doing business where we live. We become entranced because we quickly figure out the small web of connections within everyone's lives here. Dave’s nickname around here is, “The Insurance Guy.’ That has been a huge bonus for us.

We eventually had conversations about me joining the business and working with Dave at the office. We’ve been married a long time, but there was this question of how we would manage working side by side. I eventually joined him.”

David: “There are a lot of opportunities to understand one another’s perspectives when you’re married and working together. Our business requires many decisions. Thankfully, I trust her decisions completely.”

Kathleen: “We’ve been here a long time. Watching changes in the neighborhood has been interesting. Now, a lot of younger millennials are living here. We’re now insuring the children of some of our original customers that Dave insured back in 1997. So it’s either a sign that we’re getting old, or oh my gosh, we’re moving into a second generation.”