Somehow, seconds blur into hours as your dream home is reduced to smoldering embers. Your mind races. How could this fire have started? Everyone — including your tiny Yorkies and your daughter’s recently rescued kitten — is accounted for. You look around at your family huddled beneath thin metallic blankets, shivering. You are grateful that your children knew to meet at the mailbox in case of an emergency, such as this one. Your hair reeks of smoke, and your nightgown is smudged with black soot. Someone emerges from behind the fire truck’s swirling red and blue flashing lights. Could that be your insurance agent, Dennis Young?
Your cellphone rings. It’s your teenage daughter. You clutch the phone to your ear. “Hey, honey. How is your day going?” Her voice is shaking. Alarm washes over you. “Mom, someone pulled out in front of me. My car is totaled.” Grabbing your purse and keys from the kitchen counter, you bolt down the back steps toward your SUV. “Are you hurt? As soon as I get there, we’ll call Dennis Young.”
You never expected to be a widow at 60. Two decades ago, when your late husband took out the life insurance policy with Dennis Young, both of you were hopeful it would never be needed. Now, each time you make another mortgage payment or go online to pay your monthly utility bill to Shelbyville Power, you breathe a sigh of relief.
“It’s a real blessing to show up with a check from their insurance company and to be able to offer a prayer during a crisis in their personal life,” Dennis Young Sr. said. In fact, Young has been serving the Shelbyville community for nearly 40 years, and his son, Dennis Jr., has worked alongside him for nearly half of that time.
Young grew up in Columbia and attended Middle Tennessee State University (MTSU). While working at Kroger bagging groceries, he met his wife, Kay. The couple celebrated their 45th anniversary on May 24, 2026. They were blessed with two children, Dennis Young Jr. and Regan Young Rooks.
Young began working for Farm Bureau in 1988. When Cotton States Insurance Company, based in Atlanta, Georgia, began recruiting agents from Tennessee in 1997, he was the first from the Volunteer State to join the company. Ten years later, he decided he could better serve his customers as an independent broker who scours the market for competitive rates and maximum coverage, rather than being tied to just one insurance provider.
“I reached a point where I realized I needed to seek God first before anything else would work out,” Young said. “I followed the Lord’s plan with persistence, and I knew that if I formed the right partnerships, this agency would continue to be a bright light in our community and beyond.”
The very same week he opened Dennis Young Insurance, his son, Dennis Jr., who had been working toward a journalism degree at MTSU, joined him.
“Not many dads get to say they have worked alongside one of their children for almost 20 years. Together, along with our dedicated agents, including Brian Riddle, who recently retired, and our wonderful customer service representatives, throughout the years we have served our community and built a growing business,” Young said.
Dennis Jr. said, “That summer, I became licensed in property, casualty, and life insurance, and I began working at the front desk. ‘Pops’ had just left Cotton States to become an independent broker. Brian Riddle worked alongside him. The three of us worked hard and had a lot of fun together, but those were pretty lean years. In 2010, I traveled to Columbus, Ohio, where I earned my Certified Professional Insurance Agent designation. By the early 2020s, I became the office manager and co-principal agent.”
Now that Pops is semi-retired, Dennis Jr. has taken the lead in the office. He said, “As the manager, it’s my job to train and oversee the systems and procedures Pops developed and refined during his many years in the industry. I want to do my best to nurture a positive and fulfilling work environment. The ladies on my team are exceptional, and I thank God for them. Jessica Osborne-Calahan, Connie Wiens, Leeann Leversen, and Elisabeth Pinkston are all licensed agents and are the backbone of our office. Shawn Rueff is a rock star agent who constantly represents us at events around the Midstate. I can’t imagine working alongside a better team.”
According to Cornell SC Johnson College of Business, only 12% of small businesses continue into the third generation, but Dennis Jr. remains hopeful. “I hope we are among that number,” he said. “Aside from my two teenage sons, my sister had two daughters and a son. As they grow into adults, I would be thrilled if one of them approached me one day to discuss a potential career in insurance. I hope to carry on our position of God first, family second, and business third.”
Young said, “The Dennis Young who laid the foundation of the insurance company is now being taken over by Dennis Young Jr., who will continue down the same road that our customers have known and trusted for the last four decades.”
His son said, “I always stress the importance of paying attention to detail, asking the proper questions, and carrying oneself as an advisor instead of a salesman. When it comes to our customers, it’s important for us to show up and follow through. If we say we are going to do something, then we should do it, or we shouldn’t say we will in the first place. At Dennis Young Insurance, we believe it is important to be honest and to always remain humble.” GN
