[3] He graduated from Yale University and the University of Virginia School of Law where he graduated Omicron Delta Kappa, and clerked for then-chief judge of the 9th Circuit J. Clifford Wallace and then-Supreme Court Chief Justice William Rehnquist.

Prior to accepting the UVA presidency, Ryan lived in Lincoln, Massachusetts with his wife, four children, and various animals including two cats, two dogs, and nine chickens.

[4] He also served as Matheson and Morgenthau distinguished professor of law and Weber research professor of civil liberties and human rights at the University of Virginia School of Law,[2] before taking the role of dean of the Harvard Graduate School of Education.

[5] Upon being inaugurated president of the University of Virginia on October 19, 2018, his first act was to announce that in-state undergraduates from families making less than $30,000 per year would receive scholarships covering tuition, room, and board, while those from families making less than $80,000 per year would receive full-tuition scholarships.

: And Life's Other Essential Questions[7][8] and Five Miles Away, A World Apart: One City, Two Schools, and the Story of Educational Opportunity in Modern America.