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After LaFace Records, Calloway began working with then, start-up production company, Noontime Music. As vice-president of A&R, he was responsible for managing the production company and studio facilities, as well as soliciting placements for the material that was created at Noontime. At Noontime, he learned the dynamics of crafting music and honed his skills at working the creative side of the industry. During Billy's tenure at Noontime, the production company went from being a relatively unknown start-up, to being one of the most sought after production houses in Atlanta, completing songs with superstars like: Toni Braxton, Aaliyah, Puff Daddy, Jay Z, Ginuwine and Jagged Edge. Within the two years that Calloway was a part of the company, Noontime played an instrumental role in achieving more than 20 Million album sales combined from these artists and were awarded two 2001 Soul Train Music Awards for Jagged Edge's J.E. Heartbreak Album.

Billy's next position took him to Family Tree Entertainment, where he learned the ins and outs of managing artists and producers and sharpened his hands-on approach. Heading up their South office, Calloway worked with their roster of artists including, Outkast, Donell Jones, Youngbloodz, P.A., Nicole Wray, producers Eddie F and Darren Lighty, and was integral in the company celebrating their biggest accolades to date: winning an American Music Award for Best New Artist in 2000 for Donell Jones, a #1 single by Eddie F & Darren Lighty with Ruff Endz, "No More," and the recording of the now 3x Platinum Album, STANKONIA by Outkast.

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