Originally from Edmonton, Miles earned a BA majoring in Psychology at the University of Alberta. After graduating, he started with Future Shop and rapidly worked his way up to Regional Marketing Manager, overseeing stores across western Canada.

Following the sale of Future Shop to Best Buy, Miles joined an automobile windshield repair company in Edmonton. He quickly saw an opportunity for a new entrant to compete in the industry by providing a better customer experience. In 2001, he moved to Calgary to start Glassmasters with his business partner.

In 17 years Miles led Glassmasters to being one of the dominant windshield replacement companies in Alberta installing over 90,000 windshields a year. In late 2016 Miles sold the company to Western Investments and is actively working with them to open new stores and grow the company.