A graduate of Highland Park High School, Milford's first passion was writing, which he developed as a pre-journalism major at the writer-renowned University of Iowa. He later completed his bachelor's degree in English Literature at DePaul University, taking night classes while working in the volatile trading pits of the Chicago Board of Trade. Upon leaving the futures industry, Michael picked up a second degree - an associates in Multimedia - and he began working as a web and graphic designer.
