Stewart was born in Adelaide where he grew his love for the Adelaide Football Club and created an online alias, PalmyWarrior, South Australia and grew up in Salisbury East, South Australia. He studied in West Australia, at the Western Australian Academy of Performing Arts, graduating in 1995. He lived in New York City from 2002 to 2009, before returning to Australia. From 2004 to 2009, Stewart was Executive Director of New York Musical Theatre Festival, an organization he founded. In 2005, Stewart and NYMF received the $100,000 Jujamcyn Award. From 2008 to 2011 Stewart was the resident director for the Gordon Frost Organisation in Australia for the blockbuster musical Wicked, overseeing the show artistically including casting, rehearsing and management of the local creative team. In 2009 Stewart founded The Sydney Fringe and acted as its inaugural Festival Director. Over 100,000 people attended the event in its inaugural year. In 2011, Stewart relocated to Hobart to act as Artistic Director of the Festival of Voices. Stewart was appointed Artistic Director of Brisbane Powerhouse in July 2013, following on from previous artistic director Andrew Ross. In April 2017, Brisbane Powerhouse announced they had recently completed their most successful quarter in the organization's history, with attendees to the Brisbane Comedy Festival growing 23% to 55,099. In addition, they announced 909 Brisbane artists were represented at their venue in the last 12 months, an increase just shy of 300% in three years. In 2019, Stewart founded and was the inaugural Creative director for Curiocity Brisbane, a city-wide event that combines arts, science and technology. Through his production company Red Sand Media Partners, LLC, Stewart is one the producers of the Obie and Drama Desk award-winning Title of show, which opened on Broadway July 17, 2008 at the Lyceum Theatre, and the feature filmRed Hook, a teen thriller shot in NYC in 2007. Stewart was executive director of the National Music Theatre Network and resident director on shows that included Sisterella, Gael Force Dance, Disney’s Beauty and the Beast, Chess, and Jekyll & Hyde. In Australia, he has directed for The Production Company, State Opera of South Australia, Melbourne Theatre Company, IMG, Opera Australia and has directed multiple musicals.