While an undergraduate student at Wilfrid Laurier University, Shad won $17,500 from 91.5 The Beat's Rhythm of the Future talent competition.

The album was recognized for Shad's honest lyrics[9] and focus on social causes—for example, the track "I'll Never Understand" examines the Rwandan genocide and includes poetry written by his mother Bernadette Kabango.

[11] The album was supported by four singles, most prominently "The Old Prince Still Lives at Home", with its accompanying viral music video.

[12] In 2008, The Old Prince received a Juno Award nomination for Rap Recording of the Year and was a short-list nominee for the 2008 Polaris Music Prize.

[20] This album was nominated for the Juno Award for Rap Recording of the Year in 2014, and was a short-list nominee for the 2014 Polaris Music Prize.

"[24] Musically, the album was inspired by Michael Penn, Terence Trent D'arby, The Cure, Bryan Adams, and Janet Jackson.

[25] In the same year, Shad collaborated with Tanya Tagaq on "Centre", a track from her album Retribution, and also recorded for Homeboy Sandman, Skratch Bastid, and A Tribe Called Red (on We Are the Halluci Nation).

In July 2018, Shad released the lead single, "The Fool Pt 1 (Get It Got It Good)" from his new album, A Short Story About a War.

[26] The album was released in October 2018 on Secret City Records and included collaborations with Lido Pimienta, Kaytranada, Ian Kamau, Eternia, and Yukon Blonde.

[29] He also was featured on Tobi's "24 (Toronto Remix)" and its corresponding music video, along with Haviah Mighty, Jazz Cartier, and Ejji Smith.

[42] Shad has stated that he was influenced by the artists that he listened to in high school, such as Common, Lauryn Hill, Eminem, The Roots, Notorious B.I.G., and Outkast.