Diverse got his start in the Chicago hip-hop scene while being employed at a post office. He has worked or associated with Chicago hip-hop mainstays such as J.U.I.C.E., Copperpot and Iomos Marad. His debut EP, Move, featuring the track "Time", appeared in 2001.
He has professional relationships with RJD2 and Prefuse 73. He contributed to Prefuse 73's album One Word Extinguisher, rhyming on the track "Plastic". Prefuse 73 also produced the original beat for "Wylin' Out", a track which paired Diverse with the beloved New York rapper Mos Def. After "Wylin' Out" was well-received, Definitive Jux's RJD2 was tapped to remix the song. The remix was selected for inclusion on the 2002 Urban Renewal Program compilation.