Matthew Headley attended Creighton University's College of Business and School of Law under the "3-3 Program". He graduated with a B.A. in Business in 2001 and a J.D. in 2003. He then worked at Milner, Neuhaus, and Judds in Grand Island starting in 2003 and moved to Norfolk in 2005 to work at the Wentling Law Office. In 2007 he started work at the Madison Country Public Defender Office. He opened his own business, Headley Law Office (whatever the link is now), in 2011, and his office currently serves as the Public Defender for the Winnebago Tribe.