A native of Painesville, Ohio, Wiles got his first taste of the business when he was responsible for booking performers to play his alma mater Ohio Wesleyan University and hosting a time slot on his college radio station. Following college, instead of enrolling in law school, much to the disappointment of his lawyer-father, he landed a job as road manager for Atlantic Records band McGuffey Lane and later became their co-manager, witnessing up close the financial ups and downs of working musicians.
Wiles relocated to Nashville in 1987, serving as a personal manager for several artist clients before switching to business management. He started his own firm in 1992 and joined with the late Gary Smith in 1995 to form Smith, Wiles & Co., PC. In 2016, the company rebranded itself as Wiles + Taylor & Co., PC to reflect the ascent of Rob Taylor to a partner role.