Joe Massaro was born into a working-class Italian family from Westchester County, New York. Growing up, he struggled with school but later learned of his talents in the sheet metal industry after working for his uncle Vincent. He saw his career take off from apprentice to owner of the Elmsford Sheet Metal Works, the largest privately owned sheet metal company in the six counties north of New York City. He now spends his time in Mahopac, NY, at the Frank Lloyd Wright home on Petra Island and his beachfront property in Florida.