- Entered the Army Reserves in August of 1981.
- Basic training at Ft. Knox, KY.
- Trained as a Combat Medic at Ft. Sam Houston TX.
- In 1985 due to Divisional Reorganization then Sgt. Siler reclassified as a 19D, Cavalry Scout.
- Promoted to SSG in 1986.
- Attended and graduated Drill Sergeant School in 1989 and was promoted to SFC.
- Mobilized for Operation Desert Storm in 1991, where he worked as a Drill Sergeant with 5/15 Cavalry at Ft. Knox.
- In 1998 was appointed Training NCO for D/1/302. Held this position until 1999 when he was promoted to MSG and appointed First Sergeant of C Troop, 2/397 Cavalry.
- In 2003 accepted the position at then Cumberland College as Senior Military Instructor. In his tenure he has increased the size of the program by 500%.
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