This dissertation study is a constructivist grounded theory analysis of the lived experiences and expertise of DJs who oversee genre-specific radio shows at a local yet internationally renowned radio station in the Pacific Northwest. The mission of this chosen station revolves around musical discovery wherein the DJs oversee musically diverse programs based on their own expertise as well as the interest of their diverse listeners. The DJs’ life experiences will then be juxtaposed with their programming choices to understand connections between their musical pasts and current profession. Considering the history of radio as a mechanism for education, and the need to provide tools for educators to incorporate diverse music listening experiences for students in their classrooms, DJs can function as a model of professionals who are experts in the specific task of curating diverse music for diverse listeners. This study will culminate in the development of a theory which can illustrate the relationship between musical discover and the development of music listening and programming expertise.