He studied piano while growing up and briefly attended California State University at Northridge before dropping out to form an instrumental jazz trio with his brothers called the Dragons. The group released the single "Elephant Stomp"/"Troll" on Capitol Records in 1964, but its style was out of step with labelmates the Beatles, who dominated popular music at the time.
In 1967, Dragon became a touring backup musician for the Beach Boys. He was dubbed "Captain Keyboard" by lead singer Mike Love because he always appeared on-stage in a yachting cap. In addition to touring with the Beach Boys, Dragon appeared on their albums of the period, including Sunflower and Holland, and he was billed as Rumbo on a British single released in 1970, "Sound of Free"/"Lady," credited to the Beach Boys' Dennis Wilson & Rumbo.
