After graduating from Lakehead, Rapino moved to Toronto and began his career as a sales representative for Labatt Breweries. He remained at the company for 10 years in different marketing and entertainment roles. In the late 1990s Rapino founded Core Audience Entertainment, a concert promotion company that operated in Canada. Core Audience Entertainment was acquired by SFX Entertainment in 1999, which was in turn acquired by Clear Channel Communications in 2000. Rapino held several roles at Clear Channel Entertainment. He was later named CEO of Live Nation when it was spun off from Clear Channel in 2005.