During the 1990s, Rich Cooley first joined the Live Oak Skateboards team along with Donovan Dresti and Jackson Taylor. Cooley hails from Los Gatos, California and has joined several skate competitions.

In 1999, he competed in the Tampa Am Fest where he placed tenth at the Vert category. The year 2002 saw him joining several major skateboarding competitions. He participated in the EXPN Invitational held in Gwinnett County, Georgia landing at 25th place both in the preliminary and final Park skate competitions. During the EXPN Invitational at Grand Prairie, Texas he landed at 14th place in the preliminaries and finals of the Park category. It was also during this year that he joined the Mobile Skatepark Series where he competed in the Street category. At this competition, he landed on 10th place.

In 2002 as well, Rich Cooley competed at the Vans Triple Crown of Skateboarding held in Cleveland, Ohio. In this contest he ranked 25th.

According to his friend, fellow skater Jamie Smith, Cooley likes listening to hiphop, rap as well as dance music. Smith says Cooley also enjoys the party scene. The two spent time together during the 2000 World Cup of Skateboarding European tour. They got to know each other as they were the only Americans on the team.

Rich Cooley is sponsored by the following companies:

Grind King Trucks. A skateboard truck company founded in 1988 and based in Venice, California. Vision Streetwear. A footwear company also making skateboards. Terminator Skateboards. Sells skateboard decks. SoBe. A tea, fruit and energy drink company.