His debut album When This Is Over (2005) was self-made, financed with the $17,500 he won from 91.5 The Beat’s Rhythm of the Future talent competition during his time as an undergraduate student at Wilfrid Laurier University. The album is recognized for lyrics deprecating the typical rap scene and focusing on social causes—for example, the track “I’ll Never Understand” examines the Rwandan genocide and includes poetry written by his mother, Bernadette Kabango.
In 2007, he was signed by Black Box Recordings and released his second album, The Old Prince. In 2008, The Old Prince received a Juno Award nomination for Rap Recording of the Year, and was nominated for the 2008 Polaris Music Prize.
Music critics have compared his style to that of K-os and of Common, and also to a “London (England) sound circa 1990″.