After finishing college he worked for the Chicago Housing Authority, leaving in the late 1950s to go into the club business. Seeing folk star Bob Gibson perform at the Off Beat Room in 1956 prompted Grossman's idea of a 'listening room' to showcase Gibson and other talent, as the American folk-music revival movement grew. The result was the Gate of Horn in the basement of the Rice Hotel, where Jim (later Roger) McGuinn began his career as a 12-string guitarist. Grossman moved into managing some of the acts who appeared at his club — including an eighteen-year-old Joan Baez, who got her first major break with him — and in 1959 he joined forces with George Wein, who had founded the Newport Jazz Festival, to start up the Newport Folk Festival. At the first Newport Folk Festival, Grossman told "The New York Times" critic Robert Shelton: "The American public is like Sleeping Beauty, waiting to be kissed awake by the prince of folk music."