The life and times—and values and principles—of Ken Chenault, former CEO of American Express, one of the first African Americans to head a Fortune 500 company Ken Chenault’s life confounds stereotypical presumptions about and expectations for a Black American man. Born in Mineola, New York, to a dentist and a hygienist as the civil rights movement began to gather steam, much of his childhood and early adult years unfolded in a modest middle-class setting during the political and social tumult of the 1960s—the Vietnam War, the struggle for racial equality, the fight for women’s rights, the rise of the counterculture. Though he was partly informed by these inescapable influences, even then, Chenault displayed an independence of thought. Although he was athletically gifted, he chose to become a student of history, rather than pursue sports, in an effort to conquer his lack of discipline. As a student at Bowdoin and Harvard Law, and early in his career at Bain & Company, he was constantly on the lookout for educational and professional opportunities that were rare for Blacks. Intending to use his talents to champion civil rights, he found himself fighting to demolish the seemingly intractable racial barriers in the worlds of finance and business. So began his storied career at American Express, where he became known for his innovations and zealous adherence to company-building values and principles: the promotion of empathy to enlarge our understanding of one another; the willingness to accept complexity and uncertainty in crafting solutions, while refusing to yield to despair; and encouragement of unfettered but responsible creativity.