Wylie Insurance Agency: Rooted in History, Focused on the Future
Wylie, Texas, has always been a town where the past intersects with progress, and nowhere is that truer than at Wylie’s oldest business, Wylie Insurance Agency. Established in 1898, the agency began serving residents during a time when Wylie was a thriving railroad hub and a key player in the Texas agriculture industry. More than 125 years later, Wylie Insurance Agency continues to be a trusted resource for the local residents. With deep local roots, the agency is led by John Yeager and his daughter, Kylie Reising, who continue its legacy of service and community connection.
A Community Staple Since 1898
Originally from the small town of Nevada, Texas, Yeager moved to Houston after college to pursue a career in insurance. He worked at a large insurance company for a decade, learning the industry inside and out. In 1973, an opportunity arose to purchase Wylie Insurance Agency (WIA) from then-owners, Rita and Truett Smith. The Smiths, a cornerstone family in Wylie, wanted to ensure their business went to someone who would continue their legacy.
Yeager, who wanted to move back to the area, heard about the opportunity and worked out a deal with the Smith family. In the beginning, Yeager and the Smith family operated as a 50/50 partnership, and eventually Yeager took full control of the business in 1983. In the 50+ years Yeager has owned the business, he has watched it grow into a family legacy that serves not just the city of Wylie, but people all over the state of Texas. Wylie Insurance Agency’s long-standing presence speaks volumes about its commitment to service and the people who live here.
Growing with Wylie
In the early years, Wylie Insurance Agency operated out of a hardware store. Later, it moved downtown, until it finally found its current home at 201 Calloway Street in 1985. As the city grew from a rural farm town into a booming suburb, the agency expanded to meet the needs of a changing community.
That growth included both staff and services, with the agency employing a team of six in 2025. WIA now offers auto, homeowners, life, health, and business insurance—and serves clients not just in Wylie, but across the entire state of Texas. That broad service area, however, hasn’t changed the agency’s customer-first philosophy, and Yeager says his favorite thing about the job has been getting to know the local residents and business owners of Wylie.
Yeager says, “We have grown as the city has, allowing us to serve a much larger customer base of personal and business clients.” He is quick to point out that, despite its growth, Wylie maintains its small-town feel. “It is still small enough that we know most of our clients on a personal basis,” he says.
A Legacy of Local Service
Beyond providing insurance, John Yeager and his family have played a significant role in shaping Wylie’s economic and civic development. Yeager was one of the founding members of the Wylie Economic Development Corporation (WEDC) and served on its board for over three decades, earning him the distinct honor of being the longest-serving EDC board member in all of Texas when he wrapped up his service in 2021.
Yeager calls the WEDC “the best-kept secret in Wylie,” going on to say, “I was a founding member of the board and served for 32 years. I served as President, Vice President, and Treasurer.” His civic service doesn’t stop there, though. “We try to be active in the community,” he says, noting his involvement on the boards of the Lions Club and Wylie Christian Care Center, recognition from the Rotary Club, and his 1989 Citizen of the Year award from the Wylie Chamber of Commerce.
The spirit of service runs deep in the family. Yeager’s daughter, Kylie Reising, has also served on the Wylie Chamber of Commerce board and continues to contribute through her long-term role on the Wylie ISD Board of Trustees.
Planning for the Next Generation
Looking ahead, Wylie Insurance Agency is firmly positioned for the future. “We have a perpetuation plan in place to continue to serve the community for many years,” says Yeager. He notes that Kylie has long been involved with the agency and will continue to do so in her role as Vice President. Yeager’s grandson, Bryson, is also destined for the family business. He plans to join Wylie Insurance Agency after college.
As the agency looks to the future, its commitment to exceptional service remains unchanged. When asked what sets WIA apart, Yeager explains, “We don’t represent just a single company like some agents. We represent several companies, giving our customers access to a wide range of options with their insurance.”
