When E.W. “Pete” Lilly came to Madison fifty years ago, he probably never imagined he would still be doing a job that he “loves and is proud to do,” but every day, when the key goes in the front door, Lilly Insurance is open for business. The Summers County native has seen many businesses come and go in the Madison area, along with many of the icons that made the county seat a successful community, but has stayed on Main Street, determined to make a good life for himself, his wife, four children and six grandsons. “I want a granddaughter, and maybe someday I’ll get one, who knows?”

When Lilly returned from a four-year stint in the United States Air Force, the Korean War veteran ended up in Boone County because two of his loved-ones were here already. The young insurance agent set up shop in a small office he rented from Dr. Howell. “I had a desk, a chair and a telephone. I thought I was ready for business then.”

Back in those days, there were no personal computers. “I kept all my records in files stored in a file cabinet,” Lilly said. “And I’ve still got most of those today. Yes, we are computerized, but I can still pull a file from a customer that tells me what insurance he had thirty years ago. I know there are a lot of important uses for the computers we have, but I’m old fashioned. I like a paper file to put my hands on.”

When Lilly’s original office caught fire, he moved across the street, over top of the old Ellis Department store. “We stayed there for many years until we moved back across the street into the old, original location of Kroger’s. The second floor of the building originally housed a bowling alley. “They had the pin boys who set pins back up in those days,” he said. Lilly’s greatest passion, aside from his family, in those days, was bowling. He led several teams of Little League Bowlers who included Doug Weaver and other young Madison residents who grew up to achieve greatness in other fields.

At different times Lilly was president of the Madison Rotary Club, led a team of champion square dancers and was an accomplished ballroom dancer. In order to have the time to achieve those feats, however, Lilly felt it was necessary to work exceedingly hard at his craft.

“Responsibility has always come first with me,” he said. “I had a duty to my business, my customers, my family and my employees. You have to have this kind of mindset to last in this business. In order for me to provide a good life for my family I had to work like this..”

Fifty years of selling insurance helped to provide for the education of four sons. Steve, who is the president of the Commerce National Bank, John, a medical doctor and Mark, who has been in the business for twenty-five years. His youngest son Hunter is a senior at Scott High School and an accomplished tennis player. Lilly’s oldest grandson, Chris, will soon be graduating from Virginia Military Institute as an officer in the United States Army.

Lilly declines to reveal his age, but volunteers that “I’m old enough to think about retiring.” The long-time businessman occasionally gets away from the office for a few hours to spend a little time on the links of the Riverview Country Club. “I like to play a little golf,” he said. “Its good exercise and an excuse to get some fresh air and see some of my friends.”

When asked if he’s ready to retire, Lilly is initially reluctant to answer. “My business is going well, and I trust Mark and the rest of the people here to run it in the way that has made us successful. Someday soon I’ll be turning it over to Mark to see what he can do with it.”