Many business leaders craft successful companies but only a few elevate that to the level of a masterpiece. What is it about some companies and leaders that allows them to achieve this status? How does the vision of ‘the good life’ differ across corporations, large and small? Charles Spinosa is a management consultant and the author of several books. His latest book is called Leadership as Masterpiece Creation: What Business Leaders Can Learn from the Humanities about Moral Risk-Taking. Greg and Charles discuss Charles’s vision of business leaders as artists and creators who shape organizations into masterpieces, rooted deeply in humanities and philosophy. The conversation covers various business leaders, including Jeff Bezos, and how their leadership styles create distinctive moral orders within their companies. Charles connects principles from Shakespeare, Nietzsche, and Machiavelli to modern business practices and explains how leaders can cultivate courage and virtue within their organizations. They also explore the differences between founders and inheritors of businesses, the role of leaders in shaping corporate culture, and the implications for leadership education. *unSILOed Podcast is produced by University FM.*