An Ottawa native, Harewood attended Ashbury College, a private school in Rockcliffe, where he was headboy.
Harewood volunteered for CKCU-FM and CHUO-FM before moving to Montreal, earning a degree from McGill University in political science and becoming a programmer and station manager for CKUT-FM.
At CKUT, he hosted a weekly program, Soul Perspective, about Black Canadian issues.
Notably, he devoted several episodes of the program to the issue of homophobia in the black community after a performance poetry night at which poet Judge Dread Mathematik performed a work which some audience members felt was homophobic.
[2] He remained in that role until September 2009, when he joined CBC News: Late Night.