Scott is an entrepreneur and marketing professor at New York University’s Stern School of Business. Growing up in a lower-middle-class household in California after his parents' divorce, he relies heavily on his mother's unwavering support. He frames his personal history, moving from an unremarkable student to a successful businessman, as a foundation for his guidance on modern masculinity and personal responsibility.

Sylvia is Scott’s mother, a resilient woman who raises him as a single parent in Tarzana, California, after a divorce drops them into the lower-middle class. She enforces strict standards of hygiene and presentation while providing a fierce, unwavering love that Scott credits as the primary reason for his survival and eventual success.

Tommy is Scott’s father, a handsome salesman whose charisma makes him successful in business but unreliable at home. After divorcing Sylvia, he provides very little financial support for his son. His emotional distance and extreme frugality leave a lasting impact on Scott's views regarding generosity and fatherhood.

Adam is Scott’s best friend of fifty years. The two bond early over childhood mischief, establishing a lifelong connection. Adam consistently demonstrates open affection, social inclusion, and steadfast loyalty, serving as a prime example of the vital importance of male friendship that Scott advocates for.

Beata is Scott's second wife and the mother of his two sons. Their relationship develops slowly but deepens into a long-term partnership that Scott credits with pulling him out of a decade of dangerous social isolation.

Margaret is Scott's first wife, whom he dates from his early twenties into his mid-thirties. She provides essential relational boundaries and encouragement, notably urging him to apply to business school. Their marriage dissolves as Scott becomes consumed by his professional and social ambitions in New York.

Alec is Scott's older son, whose birth initially brings Scott feelings of nausea and panic rather than immediate joy. As he grows into adolescence, he exhibits typical teenage independence, occasionally rolling his eyes at his parents while attending boarding school.

Nolan is Scott's younger son. He maintains flashes of pure childhood connection with his father, such as enthusiastically pointing him out at a soccer camp. His occasional illnesses instantly strip away Scott's daily anxieties, leaving only paternal concern.

Brett is a devout Mormon teenager with strong academic habits who becomes Scott's closest friend during adolescence. Because Brett avoids alcohol and drugs, he provides a protective social influence that keeps Scott out of serious trouble during his vulnerable teenage years.

Drew is a popular and athletic peer at Emerson junior high. When a minor neck injury jeopardizes his football career just as college scouts are visiting, his sudden loss of opportunity teaches Scott a clear lesson about relative privilege and the precarious paths available to young men of color.

Pat is a gifted young man from a farm in Visalia. He bonds with Scott over their shared financial struggles during college. As a gay man in the 1980s, Pat faces severe social exclusion, a reality that deeply affects Scott's understanding of systemic privilege.

Terry is a generous, entrepreneurial man who acts as a stabilizing male role model for Scott when his own father is absent. He provides much-needed guidance in the household, though he keeps certain realities about his own personal life hidden.

Paul is a dedicated family man who steps into the role of father for Adam. Later in life, he serves as the full-time caregiver for his wife, Dvorah, who has late-stage dementia. Scott views him as an exemplar of true masculinity based on service and sacrifice.

David Aaker is a prominent marketing theorist known as the founder of modern branding. After inspiring Scott in the classroom, he later joins Scott’s brand consultancy firm, Prophet, as vice chairman, lending crucial credibility and expertise to the young venture.

Karsen is a glamorous woman who faces severe personal hardship after her husband's business struggles. Despite battling a dependency on pain medication following back surgery, she demonstrates intense loyalty by driving unannounced from San Diego to Las Vegas to support Sylvia during an illness.

Asheley is the daughter of Tommy and his third wife, Linda. She helps fulfill Sylvia's wish to visit family in London by securing an airline upgrade. She and Scott grow close later in life, often discussing the complicated legacy left by their father.