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Born and raised in Dayton, Ohio, Schilling was raised by a single mother alongside two other siblings. A troublesome child, Schilling was expelled from four different schools and took up Muay Thai at 15 years old, hoping that it would give him direction and focus. After being kicked out of the family home at 17, he worked odd jobs and began his fighting career in local Toughman Contests while living in a small property that his grandmother owned with his brother Kevin. After his grandmother died, Schilling moved to Los Angeles, California where he found work as a personal trainer at a YMCA. He met his future trainer and business partner Mark Komuro while training at the LA Boxing Club, in downtown Los Angeles. When that gym shut down, the pair moved to a spartan gym situated in a dilapidated structure that had formerly housed the Lincoln Heights city jail, with Schilling being announced at fights as fighting out of "The Jail." In keeping with that theme, when Schilling and Komuro decided to open their own gym, they were inspired to name it after the exercise area in prison, and in 2007 they opened The Yard, a Muay Thai gym located in Lincoln Heights.

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