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.

Currently, Wiles serves on the Boards of the Country Music Association and the Academy of Country Music Lifting Lives. He is a former board member of Nashville's WPLN as well as Leadership Music, and a member of CMA, ACM, NARAS, TSCPA and AICPA. He is also co-owner (along with Marghie Evans) of Do Write Music, a publishing administration company. He is a Certified Public Accountant and earned his MBA from the University of Dayton.

Outside of work, Wiles is an avid cyclist and has ridden his bike on six continents in countries as far flung as Chile, Bhutan and Madagascar. He met his wife, Diana (a 30 year veteran of the Country Music Foundation), at the Bluebird Café on his first night in Nashville, and they have two daughters, one who is in law school and another who works in the music industry in New York.