 In 1919, his father Morris Milstein, an immigrant from Russia and who started out as a floor scraper, founded the Circle Floor Company, Inc., a wood flooring company, and later, the Mastic Tile Company, a vinyl flooring company.Milstein attended DeWitt Clinton High School and New York University for two years before joining the U.S. Army during World War II where he served in the Army Signal Corps in Missouri.After the war, he returned to the family business eventually become president of the wood flooring side of the company while his brother Seymour Milstein served as president of the vinyl flooring side of the business.