Strickland grew up in the Manchester neighborhood of Pittsburgh, Pennsylvania, and graduated from Oliver High School.

[2] He then attended the University of Pittsburgh, where as an undergraduate he founded the Manchester Craftsmen's Guild as an after-school program to teach children pottery skill in his old neighborhood.

[4] Following graduation he continued to build the Manchester Guild into an innovative nonprofit agency that uses the arts to inspire and mentor inner-city teenagers.

[6] He has served on the boards of the National Endowment for the Arts, Mellon Financial Corporation, and the University of Pittsburgh.

[4] In June 2018, Strickland announced that he would be stepping down from his role as president and CEO of Manchester Bidwell Corp., but that he would remain on as executive chairman.