R. Adam Smith welcomes Octavian Pilati, an investor, strategist, and founder of The Anti-Fragile Family consultancy. Born into an Austrian aristocratic family with a millennium of heritage, Octavian shares his unique journey into family enterprise leadership following a crisis. The conversation explores critical aspects of family financial planning in multigenerational contexts, including next-gen leadership preparation, the merit versus entitlement approach, and communication strategies that build trust. Octavian offers valuable insights on family wealth office dynamics, resilience building, and the importance of balancing internal family knowledge with external expertise when navigating transitions and succession planning.