Born in southwest Washington on January 30, 1835, Shepherd dropped out of school at 13 and took a job as a plumber's assistant. Eventually, he worked his way up to becoming the owner of the plumbing firm. He then invested the profits from that firm in real estate development, which made him a wealthy socialite and influential citizen of the city. (One of his luxurious properties was Shepherd's Row, a set of rowhouses on Connecticut Avenue designed by Adolf Cluss; Cluss would later be the star witness at Shepherd's congressional investigation hearings.)