Dillard was born in the 187th Street projects of Carol City, Florida. As a teenager, Dillard 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 Swing, a member of the band Jodeci. However, he was rejected by several of the major labels, so he sought many other jobs outside of music. After graduating from high school in 1998, he studied international business management at the University of Nevada, Las Vegas for two years and attended Barry University for two months. He returned to Florida to continue pursuing his music career after receiving a phone call from a representative of the independent label Poe Boy Entertainment. Dillard signed with Poe Boy in 2006, and as Flo Rida he began affiliating with other Florida rappers, such as Rick Ross, Trina, T-Pain, and Trick Daddy. A promotional street single entitled "Birthday", featuring Rick Ross, was his first significant release. He made his mainstream debut with the song "Bitch I'm from Dade County" on DJ Khaled's album We the Best, which featured Trick Daddy, Trina, Rick Ross, Brisco, C-Ride, and Dre. Flo Rida received worldwide acclaim and popularity with the chart-topping success of his first single, "Low", featuring T-Pain. It was his first official single from his debut album Mail On Sunday and the soundtrack to the movie Step Up 2 The Streets. "Low" reached #1 on the Billboard Hot 100 chart.[4] "Elevator", featuring Timbaland, "In the Ayer" featuring will.i.am, and "Roll" featuring Sean Kingston followed and all charted on the Hot 100 and other charts. After the success of Mail on Sunday, Flo Rida made guest performances on other R&B, rap, and pop singles, including "Move Shake Drop" by DJ Laz, "We Break the Dawn" by Michelle Williams, the remix of "4 Minutes" by Madonna, "Running Back" by Australian R&B singer Jessica Mauboy, "Feel It" by DJ Felli Fel, and the remix of "Speedin'" by Rick Ross. During the summer of 2008, he did live performances on the Fox dance competition program So You Think You Can Dance in the US and 2008 MuchMusic Video Awards in Canada. He appeared on the albums We Global by DJ Khaled, Gutta by Ace Hood, and The Fame by Lady Gaga, among others. According to ,Billboard magazine, Flo Rida began recording his sophomore nine months after Mail On Sunday. The album is titled R.O.O.T.S. (Route of Overcoming the Struggle) and was released on March 31, 2009. Producers include JRock, Dr. Luke and DJ Montay. On February 18, 2009 Flo Rida got his second US number-one hit, "Right Round", the first single from the album. "Right Round" jumped from number 58 to the top spot in one week. In The States the song broke a record for the most digital one week sales, with 636,000, beating the previous record he had set himself with "Low". The second official single was "Sugar", which featured R&B singer Wynter Gordon. The song reached at #5 on the Billboard Hot 100. The second single from R.O.O.T.S. is "Sugar (feat. Wynter)." "That record has the heavy 808s in it. We used an Eiffel 65 sample. It definitely is gonna get the clubs rockin'. The girls are gonna love this record. Wynter, a new artist off of Atlantic Records, sings the hook and she's saying her lips are like sugar." The title track is as equally melodic as it is different in subject matter. On "R.O.O.T.S.," Flo Rida describes overcoming the poverty and danger he faced as a youth to follow his dreams. "I can't hate where I'm from/'cause where I'm from made me," he triumphantly harmonizes on the track. "I came from the bottom of the slums/But now I got me."