Friedman began his career as an infantry officer in the U.S. Army's 101st Airborne Division. In March 2002, he led a rifle platoon into Afghanistan's Shah-e-Kot Valley to engage Taliban and al Qaeda fighters as part of Operation Anaconda—a battle later written about by journalist Sean Naylor in "Not a Good Day to Die". A year later, Friedman commanded a platoon during the invasion of Iraq. He led troops during combat and counterinsurgency operations in Hillah, Baghdad, and Tal Afar. Friedman left active duty in 2004 after spending the latter portion of his Iraq tour as a rifle company executive officer. He was awarded two Bronze Stars for his service in Afghanistan and Iraq.