[1] He graduated from Riverside University High School in Milwaukee, Wisconsin, and Carroll College.

Riley has served on the boards of the Milwaukee chapters of the YMCA and the American Red Cross.

[2] Riley became part of Talossan history when on April 20, 1982, he facetiously signed the Treaty of Milwaukee as the "United States Ambassador to Talossa", "ceding" lands to Talossa and "recognising" its sovereignty.

[4] Prior to assuming his current role, Riley was Executive Director of the Wisconsin Housing and Economic Development Authority.

In November 2020, Riley was named a volunteer member of the Joe Biden presidential transition Agency Review Team to support transition efforts related to the Department of Housing and Urban Development and the Federal Housing Finance Agency.