In 1935, Byrd, nicknamed “Young Harry”, left the University of Virginia in Charlottesville to shore up his father's newspaper, "The Winchester Star". He also gave up an opportunity to join a global business in Paris. The "Star" had been without a full-time editor since his father left to represent Virginia in the United States Senate in 1933, as the Great Depression intensified. Upon joining the paper, his father warned him, "If you make too many mistakes, you're gone." However, the father also arranged for his son to learn the publishing business under the tutelage of John Crown at the "Harrisonburg Daily News Record". Within a year of assuming the helm of the "Winchester Star", Byrd became its editor and publisher, although his father retained financial control and advised him on editorials.