Judge Stuart is a graduate of Stanford University, Harvard University School of Education, and Georgetown University Law Center. He began his legal career as an associate at Brownstein, Hyatt, and Farber, P.C., where he practiced civil litigation. He then served as a deputy district attorney in Jefferson and Gilpin counties. In 2010, Judge Stuart was hired as a district court magistrate in the First Judicial District. He was then appointed as a Jefferson County Court judge by Governor John Hickenlooper in 2012. In 2018, Governor Hickenlooper appointed him as a district court judge in the 18th Judicial District. Judge Stuart has also been an adjunct instructor at Red Rocks Community College and co-founded an expeditionary learning charter school.