Bootie graduated with a degree in mechanical engineering from Old Dominion University, in Norfolk, Virginia, in 1996. He first entered racing working on late models when he was a junior in college. Following graduation, Bootie moved to Charlotte. His goal was to be a crew chief by 30, which he accomplished.
In September 2021, Bootie was brought on as crew chief for the No. 23 Toyota driven by Bubba Wallace. On Monday, October 4, 2021, Bootie earned his first win as a Cup crew chief (and 23XI Racing’s first win) when Bubba Wallace won the rain-shortened YellaWood 500 at Talladega Superspeedway.