He won two medals at the 2009 FIBT World Championships in Lake Placid, New York, with a gold in the four-man and a bronze in the mixed team events.

Olsen won a gold medal at the 2010 Vancouver Olympics in the four-man bobsled with driver Steve Holcomb.

[1] He is a native of San Antonio, Texas,[2] and a graduate of Sandra Day O'Connor High School.

Following a groin injury in June 2013 which left Olsen out of training for two months, he was later replaced on his original four-man bobsled team for the 2013–2014 season.

[3] His new team, composed of him, Nick Cunningham, Johnny Quinn, and Dallas Robinson, finished twelfth at the 2014 Winter Olympics.