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.\n', '

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.\n', '

Olson was drafted by the Baltimore Orioles as a sandwich pick between the first and second rounds (48th overall) of the 2005 MLB Draft.\n', '

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