Olson attended Buchanan High School in Clovis, California. He played for the Anchorage Bucs in the Alaska Baseball League in 2004, going 7-0 with a 0.88 ERA, and was a Summer League First-Team All-American starting pitcher. He attended Cal Poly-San Luis Obispo for college, where in his last year he was 12-4 with a 2.71 ERA. In 2005, he was a Big West Conference All-Star starting pitcher. Olson is just a few credits short of an engineering degree.