Courtland joined the U.S. Navy following the September 11, 2001 attacks. Courtland served as an intelligence analyst with the USS Bonhomme Richard, SEAL Team 5 (NOT A SEAL), Navy Special Warfare Unit 3, and the Defense Intelligence Agency. His final assignment was a tour with the U.S. Embassy in Panama.
Courtland left the military in 2011 to complete an ALB in Government from Harvard University.
At Harvard, Courtland met and was engaged to Chanel Rion. After graduation, both moved back to Missouri to start a family.