 Rosenberg attended Norristown High School in Norristown, Pennsylvania, where he was awarded the English award in his senior year.He graduated in June 1953, along with his future wife Patricia Fry.From the early mid-1950s until sometime in 1960, Rosenberg worked in various automobile dealerships (starting at a Ford dealership where he was trained by Lee Iacocca, then Lincoln Mercury, and finally Chevrolet), with a stint managing a nearly defunct medium-duty industrial equipment firm, which became successful under his management.