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John Cain has a diverse work experience in various roles and industries. John started their career as a Radio Host at KCPR from 1988 to 1993 and continued as a Radio Host at KCBX from 1989 to 1996, managing playlists and fundraising. John then worked as a Radio Host at KBEAR from 1995 to 1996, where they hosted a highly ranked blues radio show and managed playlists and advertising. John then transitioned to the music industry, working at Rounder Records from 1996 to 2007. There, they held various positions, including Radio Promotions Assistant, Bullseye Blues & Jazz Label Manager, and Product Manager. In 2007, they joined Luther Burbank Center for the Arts as the Associate Director of Marketing & Patron Services. Additionally, in 2008, John served as a Park and Recreation Commissioner for the Town of Windsor.

John Cain's education history includes a Bachelor of Science (BS) degree in Political Science from California Polytechnic State University- San Luis Obispo, which they obtained between 1987 and 1993. In 2000, they attended the Cambridge Center for Adult Education, where they studied Marketing. In 2010, they also attended Santa Rosa Junior College, specializing in HTML & CSS 1 & 2.