After college, Drake and his wife worked for two years in ministry to high school and college kids with FOCUS in Hartford, Connecticut. In 2007, he joined Fitch Ratings in New York in mortgage backed securities and public finance. He was at Wells Fargo in Public Finance from 2010-2015. He has been a partner at Bush & Company since 2015, where he and his partner run a financial planning business with a specialty in business owners and insurance planning. He serves on several charitable boards in Boston, holds his Series 7 and 66 and the AIF and CEPA designations. Drake graduated from Trinity College (CT) with a B.S. in Economics. He and his wife Sarah live in Charlestown and have three children.