He was the youngest person to be appointed as the Executive Director of Detroit’s NAACP branch at 24 years old. Madison worked in public relations for General Motors Corporation and as a statistician for the St. Louis Cardinals of the NFL. He began his radio career in 1980 in Detroit at WXYZ-AM before moving to WWRC-AM and then WOL-AM and XM/Sirius Satellite Radio. In 2015 he talked for 52 hours straight setting a Guinness World Record.