As a son of one of the founders of the Hanover Shoe Farm, named after the businessmen’s shoe company, he assumed farm management in 1922. In one of the most important transactions in harness history, in 1926 Sheppard purchased a 69-horse dispersal from the Estate of A. B. Coxe – a group of horses which came to be the base of Hanover’s equines, such as Hanover’s Bertha, the first 2:00 trotter in a race. The quality list of horses produced and acquired (including one person) during Sheppard’s time at the Hanover helm (he retired from farm management in 1964) established Hanover as the world’s leading standardbred nursery – the person was his handpicked successor, John Simpson Sr . Sheppard was also the President of the U.S. Trotting Association (1950-1958) and the first Chairman of the Pennsylvania Harness Racing Commission, starting in 1959 and resigning in 1963 after establishing the base upon which pari-mutuel harness racing in the state rests to this day.