Iconoclasts with strongly held beliefs and a willingness to buck orthodoxy, Apple's Steve Jobs and the Chicago Bulls' Phil Jackson shared similarities in character, leadership style, and life experience that extended beyond the extraordinary successes they achieved in their chosen fields. Both came of age in the United States of the mid-20th century, a time and place characterized by Americans' growing interest in philosophical traditions outside of the Western mainstream. In their teens and twenties, both men became interested in Eastern religious practices. As young men, Jobs (who would as a teenager travel to India to study Buddhism) and Jackson (whose interest in Eastern practices earned him the nickname "The Zen Master") developed a particular affinity for the Zen tradition of Buddhism, which had a lasting influence on each man's worldview. Although Jackson and Jobs were very different leaders operating in remarkably different industries, both men's rise to the top of intensively competitive fields were influenced by their commitment to three Zen principles: nondualism, practical wisdom, and inherent enlightenment. This note gives a brief overview of the history of Zen and the philosophical framework that underpins it, then describes the potential that these three tenets hold for unlocking strategic insights.