Taylor Gillespie was born in Canon City, Colorado, into an agriculturally based family and horses have always been a part of his life. He competed in reining and reined cow horse as a youth and was exposed to some of the best in the industry. During his senior year of high school, he felt a calling to serve and do something bigger than him. This led Taylor to pursuing an Army ROTC scholarship. Taylor graduated from the University of Saint Mary in Leavenworth, KS in 2007 and was commissioned as a 2nd Lieutenant in the US Army shortly thereafter, assigned as an Armor Officer. After completing Basic Officer Leadership Course (BOLC) 3 and some specialty cavalry scout schools at Fort Knox, KY, Taylor was assigned to 3rd Battalion, 61st Cavalry Regiment (3/61) at Fort Carson, CO. Upon arrival, Taylor learned from the Squadron Commander that the unit had too many Lieutenants which led Taylor to being assigned to 2nd Battalion, 12th Infantry Regiment (2/12), where he was immediately deployed to Afghanistan where he served as a platoon leader in Dagger Company (heavy weapons). Taylor and his platoon were based out of Fob Blessing in the Pech River Valley of the Kunar Province.

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Upon his return to the US in May 2010, Taylor knew that he had to get back to riding horses. He also met his future wife, Jennifer, at his welcome home ceremony. He was immediately promoted to Captain after arrival and began the process of exiting the Army. In May 2011, Taylor left the Army and spent the next several years working as an assistant for some of the best trainers in the industry. In April 2014, Taylor and Jen were married and later that year moved back to Colorado and established Gillespie Performance Horses LLC. They quickly went to work building a customer base that consisted of young cow horses, non-pros and lessons. In 2018, they relocated their operation to North Texas to be in a more competitive environment. Taylor was competitive in the “lion's den” of the cow horse world and enjoyed the environment. In the fall of 2022, Taylor was approached by WH to come visit the WH facility and help with a group. Taylor accepted the invitation and also brought a peer of his to see what the program was all about; he immediately fell in love with War Horses and continued to come up several times a year and assist with groups as well as helping to train the competitors for the War Horse Challenge. In November of 2024, Taylor was approached by Jacob about the possibility of moving his business to the War Horse facility in Stilwell. Initially, he declined but with prayer and further conversation with the staff and board members, Taylor and Jen knew that the Lord was leading them to War Horses. In June 2025, Taylor and Jen (along with their two sons, Kaden and Ryder-and one along the way) made the move to KS. They found a good fitting home just south of the barn and moved his customers horses into the barn. Taylor will still continue to train cow horses for the public, compete and judge but will put a larger emphasis of his time helping fellow veterans and WH staff.