Flagg works for Young America's Foundation, helping high school and college students nationwide defend their right to hear from military recruiters and to participate in JROTC/ROTC on campus.
While at Yale in the mid-nineties, Flagg worked with Young America's Foundation, members of Congress, and other Yale students and alumni to combat ROTC's second-class. Flagg's frustration with the 70-mile drive to the University of Connecticut in order to participate in ROTC culminated in the passage of the Pombo and Solomon amendments. The Foundation recognized Flagg with its National Campus Leadership Award in 1996 for his efforts on behalf of ROTC. Flagg also found time to run a successful direct-mail business while an undergraduate, in addition to being an active member of the Yale Political Union and his college fraternity.
Flagg graduated from Yale in 1997 and was commissioned in the United States Army as an officer in the Field Artillery; he served on active duty through the summer of 2000, both in Fort Sill, Oklahoma, and Fort Carson, Colorado, with the 3rd Armored Calvary Regiment. Flagg then transferred to the California Army National Guard and went to work in finance management for McMaster-Carr Supply Company in Los Angeles. Flagg spent 2003 and 2004 deployed as part of Operation Enduring Freedom, commanding a 110-man security/law enforcement detail at Travis Air Force Base. Flagg received the Meritorious Service Medal for his leadership.
Flagg hails from Nashville, Tennessee.