How can families preserve wealth and well-being across five or more generations? In this episode, I dive deep into a conversation with James E. “Jay” Hughes, Jr., legendary family wealth advisor and author of five influential books including Family Wealth. Jay shares stories from advising families for over 50 years—why flourishing, not just financial returns, is the real measure of wealth; how families like the Rothschilds and Fords illustrate both triumph and tragedy; and why choosing trustees wisely may be the single most important decision for multi-generational continuity. We explore governance, purpose, philanthropy, Aristotle’s philosophy of flourishing societies, and Jay’s own midlife realization that the true professional question is not “what do you need?” but “how can I help?”