Medina started his career with the group Apollo, who released their self titled debut on Gordy/Motown in 1979. Medina was the lead singer, other members included Kerry Gordy (keyboards), Cliff Liles (bass), Lenny Greene (drums) and Larry Robinson (guitar). Medina co-wrote three of the seven tracks, including “Astro Disco,” for which they are best known. The album was produced by Ray Singleton, former wife of Motown founder Berry Gordy.
At age 24, Medina became the head of A&R for Motown, working as a protégé to Berry Gordy. Medina then moved on to Warner Bros. Records, where executive Mo Ostin tasked him to build and cultivate the careers of the company’s urban artists as VP/GM of the Urban Music Division.
After leaving Warner Bros., Medina and longtime friend Jeff Pollack formed Medina/Pollack Entertainment. They participated to varying degress in a variety of projects, including “The Fresh Prince of Bel Air,” "Booty Call," "Above the Rim" and “Maid in Manhattan."
Medina managed Sean “P Diddy” Combs and aided in the launch of the Sean John apparel and fragrance empire. He also served as the manager of Jennifer Lopez, although she parted company with him in 2003. He later managed the career of supermodel Tyra Banks and recording artists Mariah Carey and Usher.
Medina’s stable of talent also includes comedian/writer/actor Chris Rock and entrepreneur/philanthropist Nicole Richie.