Cliff Brady earned his undergraduate degree from Loyola University Chicago in 1981. He then earned his master’s degree at the Illinois Institute of Technology.

After completing his education, Cliff worked with Gary Fencik and Leslie Frazier of the Chicago Bears ‘85 Super Bowl team, who suggested he start a program for second career planning. In 1987 he was certified through the NFLPA and he began his life’s work of representing NFL athletes and helping them to leverage their time in the NFL to spring board them into a second career after their playing days in the NFL.