As a teenager growing up in Colorado, Bobby was introduced to many outdoor sports. Bobby’s father, Bob Sr. began competing in triathlons, and took young Bobby on bike rides with him. He encouraged Bobby to take up triathlons as well, but Bobby wasn’t as excited about running and swimming. After seeing Greg LeMond in the Tour de France on television, Bobby decided cycling was the sport for him. In 1985, at age 14, Bobby decided to enter the Red Zinger Mini Classic, a stage race in Boulder for junior riders. He quickly revealed his talent by winning his age category.

Bobby went on to win many more races as a junior, including the Junior National Road Race Championship in 1987, and was named as a member of the US Junior National Team. He won the Tour de L’Abitibi, a prestigious junior stage race in Canada in 1988 and 1989, and also competed in the Junior World Championships in Moscow. Bobby graduated from Glenwood Springs High School in 1990, but not before winning the Junior National Cyclo-cross Championship that same year.