Few people know the middle Georgia billboard market as well as John Leslie. By the time Leslie Outdoor joined Trailhead Media in 2020, John had already spent more than two decades building — and selling — outdoor advertising companies across the state.
Three Companies, One Career
John Leslie’s first venture in outdoor advertising grew into a 248-face billboard plant, which he sold to TriState in 1998. He then formed a second company focused on interstate billboards, which he sold again in 2003. Rather than step away from the industry, John saw an opportunity in the shift toward digital displays and started fresh.
Building Leslie Outdoor
Leslie Outdoor was formed in 2012, built by John and his wife, Faye, around the growing opportunity in digital billboards. The company’s signs stood in Milledgeville, Sandersville, Dublin, and East Dublin, Georgia, and the Leslies also secured a permit for a double-sided digital board in Conyers, Georgia, along Interstate 20 — one of the busiest commuter corridors in the state.
The Leslies later sold select I-20 digital billboards near Atlanta to Outfront Media, a move that let Leslie Outdoor sharpen its focus on its core middle Georgia market rather than compete in the crowded Atlanta metro.
Joining Trailhead Media
In July 2020, Leslie Outdoor’s remaining digital and static billboards became part of Trailhead Media’s founding acquisitions — one of three deals, alongside Cox Media and Spartan Outdoor, that launched the company. For John and Faye, the timing lined up with a new chapter: more time with their grandchildren.
Leslie Outdoor’s structures remain part of Trailhead Media’s Georgia billboard network today, continuing to serve the middle Georgia communities John Leslie spent three decades building relationships in.
Leslie Outdoor’s structures remain part of Trailhead Media’s broader Georgia billboard network today.
Read more about our history on the About page.
Sources: Billboard Insider, Billboard Insider: Company of the Day
