He next began working as a private trainer for Charles L. Taylor, who also had stables at The Reedbeds, and his first major success: Lightfoot, winner of the 1879 Great Eastern Steeplechase, and a string of other hurdle races with that horse and Jack's the Lad.
[2] He was next appointed head trainer for Gerald Buckley (c. 1855–1935), of "Narrapumelap Estate", near Wickliffe, Victoria, but the situation was not to his liking, and nine months later he was back in Adelaide.
Around 1904[4] the family moved into a nearby property at Stacy (now Stacey) Street, Norwood, which he dubbed "Corizann Lodge", named for a 1 or 2-year old bay mare he got in exchange for a pony that cost him £3,[2] and went on to win for him hundreds of pounds.
[2] Their son "Les" Sheppard continued training at the family property at Stacey Street, Norwood, which included stables, loose boxes, and hayloft.
[7] Les was noted as a "clocker", closely watching and recording the performance of his charges,[8] and wrote for The News under the byline "Lord Setay", in homage to the horse of that name, perhaps the finest his father trained.