Frank Jacobs' biography of William M. Gaines, founder of MAD magazine, explores Gaines's eccentric personality, business acumen, and tumultuous relationships with colleagues and family.

The podcast details Gaines's unusual office, his extravagant lifestyle, and his numerous legal battles. It also recounts various anecdotes illustrating Gaines's quirky habits and confrontations, showcasing his unique approach to both business and life.

The biography further examines the history of MAD magazine, including its evolution and the personalities involved in its creation and success.

Finally, it also covers Gaines's controversial dealings with censorship and his eventual sale of the company.