(Mis)Fortune Favors the Virtuous

A CONVERSATION WITH NICCOLÒ MACHIAVELLI

By Keith Whitaker, PhD

Few thinkers have examined power, fortune, and adversity as unsparingly as Niccolò Machiavelli. Best known for The Prince and Discourses on Livy, Machiavelli wrote not only for rulers, but for those who must think like rulers when navigating uncertainty. In this imagined interview by Keith Whitaker, Machiavelli’s ideas are applied to the modern challenges faced by wealthy families—from succession planning to preparing for adversity—revealing why foresight, self-reliance, and “virtue” remain timeless foundations of resilience.