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Gregg was born in Philadelphia, Pennsylvania, and spent most of his early childhood in Omaha, Nebraska, before moving to Arizona at age 11. Throughout his school years, he was involved in many theatrical productions, including Man of La Mancha and Our Town. Gregg is a licensed broadcaster who has worked in many areas, from radio to television and film. As a student at the Zaki Gordon Institute in Sedona, Arizona, Gregg directed the short film '15 Minutes of Fame (2006)'. He has since gone on to direct many other projects, including 'GumptionFest (2010)', a film about art and poetry.