Sergeant Major Flesher was born on 18 February 1984 in Libby Montana. He enlisted in the Marine Corps on 22 March 2004. He attended Recruit Training at Marine Corps recruit Depot, San Diego, California. After Graduation recruit training he attended Marine Combat Training (MCT) at Camp Pendleton California. Following Completion of MCT he Attended MOS School at Fort Knox, Kentucky for Marine Armor Crewmen course (1812).
In December of 2004, he received orders to Marine Corps Air Ground Combat Center 1st Tank Battalion Twentynine Palms, California, where he served as a driver on an M1A1 Main Battle Tank.
In July of 2005 Sergeant Major Flesher was promoted to the rank of Lance Corporal. In November 2005 he deployed with the 11th Marine Expeditionary Unit (MEU) in support of Iraqi freedom 5-7 where he was promoted to a loader on an M1A1 Main Battle Tank.
In July 2006 Sergeant Major Flesher was promoted to Corporal and shortly after his arrival from the MEU he requested to deploy with Bravo Company 1st Tank Battalion, where he was promoted to a Gunner on an M1A1 Main Battle Tank.
In April 2007 he deployed with 1st Tank Battalion Bravo Company 1st Platoon as a gunner on the Platoon Sergeants Tank to Al Assad Air base.
In November 2007 Sergeant Major Flesher was promoted to the rank of Sergeant, where he served as the battalion Safety officer for 1st Tank Battalion. In September of 2009 he was hand selected to deploy as a tank commander on the 11th MEU as the 3-tank commander of 1st Platoon Delta Company where he assumed the duties as a section leader for the Tank platoon in support of 2nd Battalion 4th Marines.
In June 2010 he received orders to Marine Corps Detachment Fort Knox, Kentucky, where he served as a Marine Armor Crewman Course (MACC) Instructor. Shortly after the BRAC Move of the Armor unit of Fort Benning Georgia, Sergeant Major Flesher was awarded Tanker of the year for 2011.
In February of 2012 he attended Marine Corps Martial arts Instructors’ course at the school of infantry Training Company, Camp Lejeune, North Carolina where he earned the additional MOS, Marine Corps Martial Arts Instructor (0916).
In October of 2012 he attended Drill Instructor School, MCRD San Diego, California where he earned the additional MOS, Marine Corps Drill Instructor (0911).
In November of 2013 Sergeant Major Flesher was promoted to the rank of Staff Sergeant, where he served as a Drill Instructor, Senior Drill Instructor, and Chief Drill Instructor for Golf Company 2d Battalion. In December of 2014 he was selected to represent his Battalion as the Battalion Drill Master for the remainder of his time on MCRD San Diego, California.
In February of 2016 he received orders to 1st Tank Battalion Bravo Company 3rd platoon, where he is assigned as a Platoon Sergeant/Tank Commander.
In February of 2017 Sergeant Major Flesher was promoted to the rank Gunnery Sergeant and was hand selected to serve as the Company Gunnery Sergeant of 1st Tank Battalion H&S Company.
In September of 2018 he received orders to Rensselaer Polytechnic Institute to serve as the Assistant Marine Officer Instructor (AMOI) where he supported OCS as a Sergeant instructor for two summers and for the third summer supporting OCS for two cycles as India Company First Sergeant.
In September of 2021 Sergeant Major Flesher received orders to his current duty station to Marine Wing Support Squadron 273 where he serves as the Senior Enlisted Leader of Airfield Operations Company, Headquarters and Service Company, and Engineer Company.
Sergeant Major Flesher was frocked to his current rank in November 2024, and currently serving as the Support Battalion Sergeant Major, MCRD Parris Island, South Carolina.
His personal awards include the Navy and Marine Corps Commendation medal in lieu of 2 gold stars, and a Navy & Marine Corps Achievement Medal.