Glass was raised in the Bensonhurst neighborhood of Brooklyn, New York. He grew up in an Orthodox Jewish household. In 1977, while engaged in pre-med studies at Brooklyn College, he began a stint as an R&B/dance disc jockey at the college's radio station WBCR. Still a student, he was subsequently hired as the first DJ for the influential discotheque, Regine's.
Glass joined the influential indie dance label SAM Records as vice president working with Gary's Gang, John Davis and the Monster Orchestra and the Evasions. He began focusing on developing artists’ careers, rather than just trying to pick hit records. Significantly, Glass promoted street bands when other more conservative and larger labels had not.
Glass joined Chrysalis Records in 1983 as Director of New Music Marketing and was later appointed Senior Vice President. During his six years with Chrysalis, he helped guide the careers of such stars as Pat Benatar, Huey Lewis and the News, Billy Idol, Spandau Ballet, Jethro Tull, Icehouse, The Divinyls, Sinéad O'Connor and Was (Not Was), among others. He also developed a strong college and intern program, which cultivated a number of talented young executives who later went on to high-level positions throughout the entertainment industry.

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