Cunningham attended Howard University, where he earned a Bachelors degree in Economics and graduated caum laude. He continued his academic career at the University of Chicago – The Booth School of Business, at which he earned his M.B.A. in Finance. Post graduate school, Cunningham gained valuable experience as an investment analyst for Connecticut Mutual Life and account executive at Merrill Lynch, Co. He eventually went on to manage social purpose investing for Evangelical Lutheran Church in America (ELCA). In addition to his educational and work history, Cunningham had all the credentials and experience to then found Creative Investment Research, Inc., creating a new community development investment vehicle and implementing corporate governance policy initiatives. Cunningham currently writes a commentary column on small business for the Washington POst’s Capitol Business.