Chester has worked as a professional radio announcer, producer, and disc jockey in the Los Angeles market. He holds memberships in the National Broadcasters Association and the Community Broadcasters Association. Starting in Southern California, his live name reading services have now expanded nationwide, with him and his team providing these professional services for university-wide commencement ceremonies as well as smaller department convocations and celebrations.

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In addition to his work in media, Chester spent several years as a university professor and secondary school teacher before earning his doctorate in education from Pepperdine University. In his free time, he enjoys traveling and playing recreational ping pong.