Holiday is a media strategist and author, most famous for his work as director of marketing for American Apparel, where he witnessed the very public downfall of former CEO Dov Charney. His experiences at the clothing retailer inform some of his theories on the dangers of ego.
Holiday is also a college dropout and spent several years advising major music stars at a Los Angeles-based talent agency where he witnessed firsthand the dangers of inflated self-worth. He admits to succumbing to his own ego-driven tendencies and writes to encourage others to reflect critically on the voice in their own head if it urges them to rest on their laurels.