Cronauer attended the University of Pittsburgh where he led a group that founded the school's first student radio station, now WPTS-FM. His subsequent media work included being the classical morning host in Roanoke, Virginia at WVWR, now Virginia Tech's WVTF.
He earned a master's degree in Media Studies from the New School for Social Research in New York City and a Juris Doctor degree from the University of Pennsylvania. Cronauer's law practice concentrated in information and communications law. Cronauer consented to disbarment in the District of Columbia in October 2014 for reportedly misleading consumers through misrepresentations and deceptive and fraudulent loan modification and foreclosure prevention practices. Later, he worked as a special assistant to the Director of the Defense Prisoner of War/Missing Personnel Office.