Bob began acting while living in Columbus, GA when he was twelve and continued when he moved back to his hometown before his sophomore year in high school. As a freshman, Bob attended Wright State University in Ohio in their BFA acting program then transferred back to New York and graduated from SUNY college at Buffalo with a BA in theatre. After college, Bob spent 5 years in Chicago doing lot's of theatre and after getting his SAG card he moved to Los Angeles in 2000. In 2004, Bob produced his first play under the name "SkyPilot Theatre Company" and in 2006 made SkyPilot a non-profit corporation in which he is the former artistic director.

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