Jimmy Caldwell

My insurance career began in 1994 when I was first licensed as a property & casualty agent in the state of Florida. As a second generation insurance professional, you could say that insurance is in my blood. from 2007 until 2022, I was an Exclusive Agent for Allstate Insurance. Being a captive agent meant that I couldn’t always offer my customers the same choices that an independent agent might be able to offer. So when I sold my agency in 2022, I decided to start putting together an independent agency that would allow me to offer the broadest possible spectrum of insurance options.

I am a 1999 graduate of Randolph-Macon College in Ashland, VA, with a BA in Economics. I have been married to my beautiful wife since 2002. Together we have three children and two dachshunds. When not working or chauffeuring kids around town, we love spending time at the beach, visiting theme parks, or just simply enjoying the outdoors.