Growing up with his father in the Air Force, Stewart played multiple sports in a number of different locations.

[1] In the mid 1990s, Stewart began working as a coach with the Lakeside Lightning and Athletes in Action Australia.

[2] In 2000, Stewart became the inaugural head coach of the Lakeside Lightning in the State Basketball League (SBL), guiding them to a grand final berth in their first season.

[2] In his first season, he guided the Lynx to the grand final series and subsequently earned WNBL Coach of the Year honours.

[2] He also served as Lakeside Recreation Centre Manager, earning the 2003 WA Male Administrator of the Year at the Basketball Australia Junior Awards Presentations.