As a teenager, he worked with local rap group 2 Live Crew and formed his own amateur group with some friends called the Groundhoggz. His work with 2 Live Crew member Fresh Kid Ice attracted attention of DeVante, a member of the band Jodeci. However, he was rejected by several of the major labels, so he sought several other jobs outside of music and briefly attended the University of Las Vegas and Barry University. He returned to his home state of Florida to continue pursuing his music career after receiving a phone call from a representative of the independent label Poe Boy Entertainment.
Flo Rida made his mainstream debut in the song "Bitch I'm from Dade County" on DJ Khaled's album We the Best. His first EP Florida Streets was released on November 25, 2003. He started appearing in mixtapes in 2006. Flo Rida signed with Poe Boy Entertainment in 2007, and began affiliating himself with other Florida rappers such as Rick Ross, Trina, and Trick Daddy. In his earlier days, he has been known to shout out his phone number. Before We the Best, released a promotional street single entitled "Birthday", featuring Rick Ross. He then released a club based single entitled "Low" featuring T-Pain which hit 1 as the most downloaded song on iTunes in November 2007, as well as reaching 1 on the Billboard Hot 100. On November 4, 2007, the Low EP was released as a digital download and included "Low", "Birthday", and "Radio". In early February 2008, Flo Rida's second official single "Elevator" received early airplay from pop, rhythmic & urban radio stations and on February 12, 2008 it was released as a digital single. He has a tattoo of Jimi Hendrix on his left arm. He also has a tattoo of Florida on his Right wrist.