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Born in 1976 in New York City, Rubin came of age as a gay Jewish man in an environment often characterized by both diversity and progressive politics. He pursued a degree in political science, which would lay the groundwork for his eventual foray into the world of comedy and media. Beginning his career as a stand-up comedian, Rubin quickly made a name for himself, performing at venues like the Comedy Cellar and co-founding several comedy clubs. His early projects included podcasts aimed at blending humor with political commentary, most notably "Hot Gay Comics" and "The Six-Pack."