Stewart was born and raised in Tyler, Texas by his parents with his 3 siblings (2 brothers and a sister).
Stewart was on the John Tyler Lions high school team that went 16–0 and won the 1994 class 5A Division II state championship of Texas, a season that included a memorable regional semifinal against Plano East Senior High School.
In 2008–2009, Stewart was working as a biology teacher in Spring Woods High School in Houston, Texas.
As of 2014 he was on the coaching staff of the McCallum High School Knights football team.
In January 2020, he started his role as head coach for the Sam Houston Hurricanes in San Antonio, Texas.