 Stein then suggested that he get some experience on a working farm, so he learned the ropes on the Thoroughbred farm of Tony Matos.He then went on and broke and galloped horses for Johnny Longden and Longden's son, Eric Longden before starting his career as a jockey.He graduated from jockey school in Castaic, California, and won his first race, a dead heat, in Caliente, Mexico in 1988 aboard Blue King.