Drew grew up in Lantana, Florida. Drew graduated from the United States Naval Academy in 2004 with a Bachelor of Science in Chemistry, and a Language Minor in French. He is a P-3 pilot by trade, deploying to the Middle East, Europe, Central America, Africa, and Asia. He also served tours as a Flag Aide and as a Shooter. He is currently a member of the MBA Class of 2016 at the University of Chicago Booth School of Business.