Maynard's father, Jan, was a two-time Ohio high school state wrestling champion. He also has a sister named Misty. Maynard attended Bonanza High School and Durango High School (Las Vegas), and transferred to St. Edward High School, Lakewood, Ohio, for two years, where he wrestled for coach Greg Urbas, and excelled in its wrestling program.
In 1997, he placed second in the Ohio High School Athletic Association (OHSAA) state tournament in the 140 lb weight class for Division I. In 1998, he was the state champion at the 152 lb weight class. His high school record was an impressive 135–16, including being undefeated in his sophomore and senior years. His nickname of "Bully" came from his dog, Hank, a bull terrier he rescued. Maynard wrestled alongside former UFC light heavyweight champion Rashad Evans at Michigan State University. They were also roommates. He was redshirted in his freshman year. In 2001, he placed eighth at the NCAA Division I Collegiate Wrestling Championship at 157 lb weight class. In 2002 and 2003, he placed seventh. The performance earned the MSU co-captain All-American honors for the third time in his collegiate career.
Upon graduation, Maynard ranked 11th all-time in MSU history with 106 career wins and seventh with 26 falls. After not making the 2004 US Olympic wrestling team, Maynard considered retirement from the sport. He was then recruited to be a sparring partner for mixed martial arts fighter and former Lightweight UFC champion B.J. Penn. With his exposure to the new sport, Maynard sought to compete in it. With his wrestling connections, he eventually became a student and training partner of UFC Hall of Famer Randy Couture.

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