Caballero began skating in 1976 at the age of 12 and started his career at age 14. His first sponsor was Campbell Skate Park. In 1979, Caballero entered a national skate contest in Escondido. After finishing fifth place, he was approached by Stacy Peralta who offered him sponsorship with Powell Peralta. He turned pro in 1980 during the Gold Cup series at the Oasis Skatepark, Southern California. By this time, Caballero had invented the 'Caballerial' (also known as 'Cab'), a skateboarding trick also known as the fakie 360 aerial. Caballero is also credited with inventing the frontsideboardslide.