After his military stint, Winn returned to Memphis where he joined Kevin Davidson & The Voices of Binghamton choir where he first met Sheri Jones Moffett.
At the same time, Winn began to sing with Richard Smallwood's Vision choir in 2000 as Moffett sang with Donald Lawrence & The Tri-City Singers.
Winn was living in Atlanta and attending Morehouse College when he and Moffett landed a contract with Kirk Franklin's former radio promoter Neily Dickerson's Church House Records label in 1999.
They recruited well-known production assists from gospel heavyweights Tonex, Myron Butler and Donald Lawrence.
The song that received the most radio attention was the duo's reprise of Roberta Flack and Donny Hathaway's "Come Ye Disconsolate."
Aside from the track "Moving Forward," Winn wrote all of the material and brought in guest artists such as Vanessa Bell Armstrong, DeWayne Woods, Jonathan Nelson and Myron Butler for the ensuing "Balance" CD.
In December 2012, Winn performed a new song "You Are the Reason" on BET's "Bobby Jones Gospel" program and announced that he was working on a sophomore CD entitled, "Perspective," due for release in late 2013.