Ashton, a native of Alexandria, Virginia, was born to an Army father and a nursing student mother. After his parents' divorce, Tampa Bay became the place Ashton called home. Growing up in what he describes as a "broken home," he sought escape and adventure as a means of coping. Humor became his guiding light, helping him navigate through tough times, including the loss of his father at the age of 14.

By the end of high school, Ashton unexpectedly found himself in Nashville, Tennessee. Clueless about life and undecided on a college major, he stumbled into the world of radio. From 1999 to the present day, Ashton has graced the airwaves at 15 different radio stations across five states. In December 2023, he celebrated his 14-year anniversary with Air1.