Ryan spent his childhood in Wilmette, Illinois, the son of Helen Marie (Bruns) and Donald Robert Ryan, a managing partner at a trade and clearing house. One of six siblings, he attended New Trier High School. He graduated from high school in 1977 and went on to Dartmouth College, where he graduated summa cum laude and Phi Beta Kappa. He earned his MBA from Harvard Business School and his JD from Harvard Law School, with honors. After this, he worked at Casa Juan Diego, a refugee camp for Latinos fleeing the Central American civil wars. He worked for Goldman Sachs as an investment banker and eventual partner, first in New York City, and then in the Chicago branch.