Galloway’s earliest employment was walking a neighbor’s dog and ended in dismissal after issues with punctuality. He babysat himself after school, worked as an usher and box boy during his teens, and continued bagging groceries in college. Galloway recounts lying to a coworker, claiming he never noticed a visible injury to her jaw, and her relief taught him an early lesson about the value of deliberate kindness. He worked selling gold coins, which made him feel dirty. Four days a week, he donated sperm until his mother pointed out the risk of his offspring unknowingly meeting one another. In business school, he and a friend named Lee launched a video rental delivery service called Stressbuster, buying discounted films to rent, until State Farm purchased the business for $2,500.

He argues that service and low-wage jobs build empathy, resilience, and a concrete understanding that success must be earned. He observed this pattern most clearly while working as a dishwasher alongside immigrant coworkers who earned minimum wage and sent nearly every dollar home to their families, leading him to recognize how much of his own eventual success stems from the circumstances of his birth.

His Morgan Stanley analyst job was horrible, with a culture inside the firm that was brutal, racist, and sexist, with a VP who once threw a chair at Galloway. The work required frequent all-night working hours, and Galloway distinguished himself by working more all-nighters than his peers. After two years, he woke up with an irregular heartbeat and was hospitalized for ventricular tachycardia, prompting him to leave investment banking.

After graduating from Berkeley’s Haas School of Business, he turned down several job offers to start his own firm. Inspired by a brand strategy course taught by Professor David Aaker, widely considered the founder of modern branding, he launched a brand consultancy called Prophet. With no experience, he cold-called and pitched to Yamaha Motor, which hired him. Upon receiving Yamaha’s first payment, Galloway wondered whether he had committed fraud. Yamaha remained a client for years, and Aaker eventually joined Prophet as vice chairman.

Prophet’s success led to a series of additional ventures. He co-founded a pet supplies e-commerce company called Aardvark with a business school classmate named Ian. They sold the company to a publicly traded firm, and Ian’s insistence on receiving half the payment in cash rather than stock saved them when the buyer’s company collapsed soon after. He launched a gift company called 911 Gifts. At a wedding, watching a bride’s visible hurt when she realized her gift was a last-minute purchase from his platform, he rebranded the company as RedEnvelope. He clashed with the company’s CEO, was removed from the board, spent half a million dollars of his own money on a failed proxy fight to regain control, and eventually returned to take back the company and install a new CEO. However, the new CEO miscalculated margins, a longshoremen’s strike trapped inventory on a cargo ship, Wells Fargo cut the company’s credit, and a software glitch shipped 12,000 gifts to the wrong addresses. RedEnvelope collapsed into bankruptcy, which Galloway calls his greatest professional failure. Galloway recommends quitting early in risky ventures, since spending 10 years leading up to RedEnvelope’s bankruptcy was more devastating than similar failures that took less than 24 months.

He acknowledges how he has benefited from being a white, heterosexual male who came of age in California at a time when he could capitalize on the developments of technology. He notes that his success is partially a product of timing, luck, and identity. Galloway argues that people should try to succeed in fields where they already show potential, rather than pursuing careers in fields about which they are passionate. 

When his mother’s cancer returned for a third time, Galloway was 38-years-old and financially secure enough to help her. He moved her from Los Angeles to a retirement community in a Las Vegas suburb, furnished her new apartment through a Williams-Sonoma client discount, and moved in to serve as her caregiver. He helped her fulfill two final wishes: a farewell visit to her family in London, made possible by his half-sister Asheley, who worked for an airline and secured an upgrade, and dying at home. He structured his days around her care while preserving his professional life with regular weekend trips to New York and Miami. During one such trip, he met the woman who would later become his wife. He returned from a trip to find that his mother had passed away two hours before he arrived. He does not regret the absence, believing he was more emotionally available because he maintained his regular life. His mother died at home, comfortable, surrounded by people who loved her, and he notes that she is one of the reasons he works so hard.

Galloway notes how nearly 60% of American children failed the1950s Kraus-Weber fitness tests, prompting President Eisenhower to establish the Presidential Fitness Test (PFT). Now that the PFT has ended, Galloway claims American culture has normalized obesity to a degree that compromises both individual health and national security, with a growing percentage of military recruits disqualified for physical reasons.

He credits his own lifelong exercise habit, exercising four days a week for 40 years, to his father, who introduced him to a Royal Navy fitness manual when he was 11-years-old. Galloway continues this tradition by doing a 10-minute version of the same workout on Zoom with his eldest son, Alec. Exercise, he argues, is a reliable antidepressant. When he skips workouts, he becomes irritable and “dark.” He describes his personal mental health regimen through the acronym SCAFA: Sweat, Clean eating, Abstinence (from alcohol and cannabis), Family, and Affection. When these five elements fall into place, his mood stabilizes.

When he first moved to New York, he took boxing and yoga classes. A trainer convinced him to enter a quarterly boxing tournament, which ended with his facial nerve temporarily impaired and a nose that still veers right. Yoga provided an avenue to meet women, and Galloway dated two yoga instructors.

Galloway notes that he went 16 years without feeling strong emotions and has never seen a therapist. He nonetheless recommends that men develop a practice of naming and sharing their feelings with people they trust.

Galloway discusses addiction among young men, characterizing the technology, food, pharmaceutical, and gambling industries as forces deliberately engineered to generate dopamine dependence, and adolescent boys are their most vulnerable demographic. Social media use of more than three hours a day, he notes, doubles the likelihood of anxiety and depression in teenagers, and the rate of deaths by suicide among adolescents has risen 56% over the last decade. He urges young men to recognize these forces as adversaries rather than entertainment, and to redirect the time captured by screens toward fitness, work, and human connection.