He left Lancing College after taking his GCSEs, and became apprenticed to trainer Charlie Hills in Lambourn.
[1][2] In 2020, Shepherd moved from Lambourn to Newmarket, Suffolk, having been retained by owners the Gredley family.
[1] He had his first opportunity to ride in a Group 1 race and a British Classic in the 2021 Oaks on Save A Forest, a 40/1 outsider owned by the Gredley family and trained by Roger Varian.
[5] The same month, he won the Lingfield Derby Trial on Ambiente Friendly for trainer James Fanshawe and was looking forward to a first ride in the Derby on the same horse but was disappointed when the Gredley owners opted for the more experienced Robert Havlin.
Shepherd secured his first Royal Ascot success in 2024, when he partnered Isle of Jura to victory in the Group 2 Hardwicke Stakes.