Shepherd attended West Hill Collegiate Institute and Don Valley Junior High School in Toronto.

Following the season, Shepherd signed with German second-tier team Giro-Live Ballers Osnabrück.

[5] On July 22, 2011, Shepherd signed for Zorg en Zekerheid Leiden in the Dutch Basketball League (DBL).

He first played with a Canadian squad at the 2005 and 2007 World University Games, helping the team to a surprise bronze medal in the latter competition.

On November 23, 2020, Shepherd signed as general manager of the Ottawa BlackJacks of the Canadian Elite Basketball League (CEBL).