Riley began his bootblack journey in 2005 as an apprentice to Leslie Anderson and Suka Malone, IMsBB 1999 and 2005 respectively. He held the title of Great Lakes Bootblack 2007 prior to taking on his position as Great Lakes Bootblack contest coordinator in 2008.  He is excited about now being the Great Lakes Bootblack Director.

Riley recently ended his tenure as Director of LRA Chicago, taking time to focus on graduate school. Riley continues to lead the ongoing effort to build and curate the organization's library. Riley was honored to serve as a judge for Mr. Ohio Leather, Cellblock Leatherman, Bluegrass Leather, Bootblack Toronto, Illinois Leather and Fetish Pride, and most recently, International Ms Bootblack in 2012.

Professionally, he is an educator and consultant, focusing on ways to make health and social service environments more accessible to members of queer and trans communities. When not busy in other endeavors, Riley enjoys the finer things - smoking new and unique cigars, leatherworking, and acquiring rare publications relative to the leather subculture.