Ten questions with an agent: Eli Gillespie, Gillespie Insurance Services

In our “Ten questions with an agent” series, we feature ClientCircle users from around the United States, highlighting their businesses, communities and perspectives on the insurance industry.

This time we’re in Redlands, California, home to Gillespie Insurance Services. The agency has been part of the community since 1986 and remains family-owned today. Known for its agricultural roots, Gillespie Insurance has grown to serve a wide range of clients, from local businesses to families throughout the Inland Empire.

Redlands is just outside of San Bernadino—nestled about halfway between Los Angeles and Palm Springs. The city is celebrated for its lush citrus groves, charming historic districts and vivid red adobe soil that gave Redlands its name. Often called the “Jewel of the Inland Empire,” Redlands blends old-town Victorian elegance with breathtaking mountain backdrops.

Now let’s hear from Eli Gillespie, owner and general manager, about his journey in the insurance industry and what drives him to lead Gillespie Insurance Services forward.

Learn more about Gillespie Insurance Services here.

Gillespie Insurance has been family-owned since 1986. What’s it like carrying on that legacy today?

I may use “family-owned” as a marketing tactic here and there, but truthfully, I want Gillespie Insurance Services (GIS) to be a professionally run business that wins because of its excellence and expertise and is able to thrive whether or not anyone from my family is involved. When my dad retired, he had already let me take over almost every aspect of the business so that no one noticed when he was gone, and I want it to be the same way for me. I want GIS to be self-managed and operating so that no one ever needs to talk to me to get the help they need. As of today, I feel really good about our progress.

Your agency has deep roots in agriculture. How has that shaped the way you serve your clients?

Farmers are very cool people. They’re highly entrepreneurial in their own way—a unique mix of traditional and experimental at the same time. They’re bold, they ask lots of questions, have strong opinions and they’re good with numbers because their business requires it much more than you might think. Talking to them in the early days shaped my approach for sure. They’re loyal clients, fantastic to work with, and I only wish there were more of them in our region where the ag industry has been shrinking.

What inspired you personally to get into the insurance business?

I was substitute teaching at the time and knew I didn’t want to do it long term, so over the summer I decided to try something new. I really just wanted to learn about business but had no experience, so I asked my dad for a job. Lucky for me, he hired me and asked me to stick with it for a year. I didn’t plan on doing it long term, but the more I got involved, the more I realized I really enjoyed it. So I stuck with it.

Beyond agriculture, what types of businesses or clients do you especially enjoy working with?

We also focus on restaurants and contractors. We’re also writing a lot more lessors risk and habitational lately as the property market has hardened. We want to expand more into manufacturers as well. We enjoy working with all people regardless of the type of business they own if they’re good people. We only niche down so we can be effective.

Redlands is such a unique community. What do you love most about serving people here?

We like serving people in the Inland Empire because we’re all aware we’re the Southern Californians everyone looks down on (using self-deprecating humor right now). Everyone knows about LA, Orange County and San Diego, but no one knows about us. It’s probably a lot like how New Yorkers feel about New Jersey.

What’s one hidden gem in Redlands you think more people should know about?

There are a lot of historical buildings and old Victorian-like neighborhoods you wouldn’t expect to see here in this area. Redlands is a standout in the Inland Empire.

How does your team celebrate milestones or wins together?

Probably not enough. We have birthday lunches and a Christmas party. We do shout-outs in our Monday meetings. Truthfully, I’m terrible at taking the time to plan fun things. I need a CFO—a chief fun officer.

What’s your go-to morning drink to get the day started?

Coffee, black, two and a half cups.

What’s the most unusual or memorable thing you’ve come across in your insurance career?

The most unusual thing I can think of is the time I visited the location of a client who raised bulls for rodeos. Seeing those beasts up close was something else.

The most memorable thing would be all the trips I made to various businesses for prospecting in the first decade of my career. Before finding information online was a thing, you would almost always need to visit the prospect’s location to gather information. So many times I would get a “hot lead” and drive 80–100 miles in any direction to go measure a building, take pictures, meet the owner, take a tour, ask questions and then drive home feeling excited about the possibility of winning the account.

If your agency had a theme song, what would it be?

No Easy Way Out by Robert Tepper from the Rocky IV soundtrack.