Caldwell is a veteran of the United States Marine Corps and the Iraq War. Following boot camp and initial training, Caldwell was assigned to the Marine Corps Presidential Support Program, where he served as a member of the security force at the presidential retreat at Camp David. Following his service at Camp David, Caldwell deployed to Iraq with 2nd Battalion, 1st Marines in support of Operation Iraqi Freedom and conducted operations in Al Anbar and Ninawa provinces. Following his service in the Marines, Caldwell worked for Rep. David Schweikert from 2011 to 2013, focusing on veterans and defense issues. Caldwell graduated cum laude from Arizona State in 2011 with degrees in Asian History and Political Science.