Raised in Chetek, Wisconsin, Bob Olson lettered four years in wrestling and had a career record of 71-17 at Chetek High School. After finishing fourth at the state tournament as a junior, he returned as a senior and went 27-1 with his only loss was in the state finals. He also lettered three years in football, serving as team captain as a senior, and two years in baseball.

Olson was a two-time Wisconsin State University champion, a three-time NAIA national tournament qualifier and an All-American for the the University of Wisconsin-Stout. He enlisted in the United State Marine Corps and wrestled two years in the service.

After fulfilling his military obligation, Olson coached one year at Stout before getting his first high school coaching job at Baldwin-Woodville in 1972. During his tenure, Stout was competing in an open tournament that included their wrestler, Dale Evans, and his brother Steve Evans, who wrestled for the University of Wisconsin. Olson informed the committee that if the siblings both reached the finals that they would not wrestle each other. The brothers did reach the finals and did not compete against each other. Dale and Steve both received the Lifetime Service to Wrestling award from the Wisconsin Chapter of the National Wrestling Hall of Fame in 2009.

After coaching two state qualifiers at Baldwin-Woodville, Olson became the head coach at Cameron High School in 1975. He coached three state champions and 34 state qualifiers and led his team to six Lakeland Conference championships and nine team titles. He was named Wisconsin Coach of the Year in 1995 after his team placed second at the state individual tournament.

Olson retired in 2004 after teaching and coaching for 31 years at Cameron to coach at his home high school in Chetek. Olson was the head coach at Chetek and then Chetek-Weyerhaeuser for 17 years. Additionally, the wrestling program began co-oping with Prairie Farm. His teams won the Heart of the North Conference team championship four times.

During his coaching time at Baldwin-Woodville, Cameron, and Chetek he had 70 state qualifiers and seven state individual champions. He celebrated 50 years of coaching in 2015 while coaching at Chetek. Olson officially retired from coaching in 2022.