He had an ideal build for a jockey and became an apprentice at the stables of John Tesseyman at Moor Monkton near his home aged only 12. According to some sources he would ride his first race four years later. In others his first race is said to be on a horse called Dusty Miller in an "ever-to-be-remembered race" between Pacolet and Partington in 1784.
Having established his reputation as a jockey, he was hired to ride the horses of Richard Savile, the future Earl of Scarbrough, and later to train them as well, at stables at Langton Wold in Malton.
He would also ride for the Reverend Mr Goodriche. After several years in Malton, he moved south to Newmarket to ride and train for Lord Foley, for which he was paid an annual retainer of £200.
lieutenant was for Foley that he would have his single success in the Derby, on Paris in 1806, winning by a head from a field of twelve. A further move would see him ride for Sir M M Sykes.
He would also ride for Henry Peirse and Sir Frank Standish.
Other horses on which he made his name included Cammillus, Magistrate, Prime Minister, Sir Malagigi, Rosetta, Rosanne, Reveller, Lisette, Scancalaldi, Epperston, Cambyses and Consul. His specialism was four mile heats, and he was regarded as the best of his generation at judging pace in these races. His skill was such that it dispelled the prejudice normally shown by the Newmarket establishment to jockeys from the north.
Indeed, with other Yorkshire jockeys John Mangle and John Jackson, it is said he "shone".
He was also regarded as an honest and dependable jockey. In his later years, in the late 1830s, Shepherd ran a public in Malton.
He received a pension from the Bentinck Benevolent Fund (the first person to do so) as a result of the years spent in the employ of the Earl of Scarbrough. Despite this, he died in 1848 in poverty, with a large family having swallowed up his savings.
He was a pioneering Northern jockey, one of the few of his time to move south to Newmarket, the home of British horse racing and gain a reputation there.