 Velazquez was born in Carolina, Puerto Rico and learned to ride there, attending a jockey school for a year and a half.On January 3, 1990, he won his first race, aboard Rodas at El Nuevo Comandante racetrack in Canóvanas, Puerto Rico.That same year, he moved to New York State and obtained guidance from leading jockey Angel Cordero Jr. Richie Allen was his first agent, followed in 1992 by Ralph Theroux.