Ventura is the daughter of a Filipino father and an African-American/West Indian/Mexican mother. While attending The Williams School, a preparatory school on the Connecticut College campus, Ventura began her career as a model at the age of fourteen, appearing in ads for Delia's, Adidas, Abercrombie & Fitch, and Seventeen. When she completed high school in 2004, she announced that she was going to pursue her career in modeling and music, foregoing college.[1] [2]

In New York - where Ventura was modeling for Abercrombie and Fitch - she took classes at the Broadway Dance Center. Producer Ryan Leslie began spotting her at clubs and parties in late 2004, later saying he was charmed by her personality. She was finally introduced to him by Sean "Diddy" Combs' make-up artist, who had worked with Ventura on one of her modeling assignments.[2]

Shortly after being introduced to music producer Ryan Leslie, Ventura's mother supposedly asked Cassie to record a song for her as a birthday gift. Cassie approached Leslie, who wrote a duet for them called "Kiss Me". Leslie played the track for Tommy Mottola, who offered Ventura a management deal. Ventura inked a deal with Leslie's NextSelection label. Leslie also co-wrote and produced Cassie's first single, "Me & U", in 2005. By March 2006, Ventura had signed with Diddy's record label, Bad Boy Records.[2]

On its release, "Me & U" proved to be a massive hit - particularily in the US. It took the charts by storm, reaching number three on the Billboard Hot 100, number four on the Billboard Pop 100, and number one on Billboard's Hot R&B/Hip-Hop Songs chart.[2] Follow-up single "Long Way 2 Go" was far less successful in comparison, peaking at ninety-seven on the Billboard Hot 100.