After graduating high school in 1990, Richardson was torn between entering the Air Force to join the Air Force band, or following the lure of performing by attending the New York American Music and Dramatic Academy in Manhattan. With encouragement from his father, Richardson flew to Orlando, Florida with his best friend Jimmy, where he earned a living as a model, writing music, performing in dinner clubs, taught ballroom dancing as a certified Latin and ballroom dance instructor and was an extra for the film My Girl. In Florida, he got a job as a cast member and performer at Walt Disney World. He played various characters including Aladdin, one of the Teenage Mutant Ninja Turtles, Prince Eric, Tigger, and Sebastian the Crab in the Little Mermaid show. He was also a backstage tour guide. At nights, he did dinner theater, playing an Italian gangster in a musical review performing various songs from the musical "Chicago," "Guys and Dolls" and "Cabaret."