In 1923, Weiss became the manager of a barbershop at the Grunewald Hotel in New Orleans. In 1924, he became the assistant hotel manager, and in 1928, he was promoted to hotel manager. First built in 1893, and known as the "Grunewald" (for its original owner, Louis Grunewald), the Grunewald opened what has been called the first nightclub in the United States, a basement room decorated with fake stalactites called "The Cave", where one could watch dancing chorus girls and listen to Dixieland jazz that would easily drown out the soothing indoor waterfalls. In 1923, a consortium of local investors purchased the hotel and renamed it "The Roosevelt" in honor of President Theodore Roosevelt, who had died four years earlier.