Bennett attended Miramonte High School in Orinda, California, and was a three-sport standout in football, baseball, and basketball.
He was awarded a scholarship for the 1997 season and switched positions to become a wide receiver for his junior year.
He played both wide receiver and quarterback in his senior season and won the Paul I. Wellman Award for All-Around Excellence.
He graduated from UCLA with a major in Political Science, and is also a member of the Sigma Chi fraternity.
Bennett has appeared on ESPN's First Take (hosted by Jay Crawford) as recently as March 24, 2010, as an NFL analyst alongside Bobby Carpenter.