Robert Dyrdek was born in Kettering, Ohio and began skateboarding at the age of 11, winning his first competition 24 days later. The same year, Dyrdek became the youngest member of the G&S skateboard team. He turned professional at the age of 16, joining the Ohio-based Alien Workshop team, forgoing his senior year of high school. He reached fourth place at the 1991 World Championships, the first contest he competed in as a professional.
As a teenager, Dyrdek attracted a growing number of sponsors, appeared in skate movies and on magazine covers, signature skateboards and other merchandise. One of his best known sponsorship deals developed after he befriended the founders of the Droors Clothing line. He not only began promoting their clothing, but was given the opportunity to design a signature line of the first athletic skate shoe. The nearly 30 shoes designed by Dyrdek helped establish what became DC Shoes. This exposure to the business side of skateboarding inspired him to venture into other projects such as the world-famous skateboarding training facility in San Diego and the now defunct hip hop label, P-Jays Records.