His song "16's With Me", whose beat sampled that of "Imperial March" from the film Star Wars, was his first big hit. In 2005, Ya Boy released his first solo mixtape Future of the Franchise, followed by his debut album Rookie of the Year on Quinn's label Done Deal Entertainment. His album features E-40, Turf Talk, Clyde Carson of The Team, San Quinn and more. The first single off the album, "Step Ya Game Up", was produced by Rick Rock.

Bay Area rap was more club-oriented with the hyphy sound, Ya Boy chose to maintain a "gangsta rap" sound, so in 2006 he began an affiliation with Black Wall Street, the label owned by Compton, California rapper The Game. On Kevin Federline's 2006 rap album Playing with Fire, Ya Boy appeared on the track "Dance with a Pimp". The Source magazine featured Ya Boy in its "Unsigned Hype" column.[3]

In 2008, he released the single "Holla at Ya Boy" produced by Cool & Dre for the album of the same name and a mixtape called Chapter 1: The Rise produced by DJ Skee. Ya Boy stated in an interview that year with Dubcnn.com that he signed himself to his own label Precise Music Group. In that interview, he also stated that in one his songs lyrics "No Replacement" of his mixtape, the chorus lyrics were often misinterpreted. Ya Boy explained, "It's funny, everyone is wondering if I'm rapping, 'You must not no who I be' I really thought I was clear when I said, 'You must not know Y.B.' frankly thats my name, guess it wasn't that obvious". In the same interview he said that he moved to Malibu, California and planned to release his music solely through iTunes