Born and raised in Ann Arbor, MI, Toby graduated from Pioneer High School in 1996. In 1999 Toby then earned a BA from Western Michigan University in Political Science – Public Law with Cum Laude Honors. Following graduation he became a police officer for the Portage, MI police department. Toby left the department to pursue a position as a bar manager with the Sunset Tavern in Miami, FL. Toby then returned to Kalamazoo, MI where he became, and still is, an insurance fraud investigator.