This roundtable explores my podcast interview with Will Young, a financial adviser who blends Stoic philosophy, behavioural psychology and surfing insights into his approach to wealth management (and to his life in general). Topics discussed include: Will's technique of loosening his clients’ epistemic rigidity and emotion-based investing beliefs by exploring their reasoning process rather than attacking their conclusions; cognitive biases like the availability heuristic, the illusory truth effect and reactance; Philip Tetlock's super forecasting techniques based on probabilistic thinking; How Will (who is on the autistic-spectrum) translates abstract concepts like Stoicism, epistemic humility and Bayesian updating into concrete financial advice; and Will's habit of listening to a book first and only reading it if it resonates enough to warrant deeper internalization. The discussion reiterated themes of intellectual humility, resisting tribal/emotional reasoning and the idea that probabilistic, unemotional thinking, whether applied to markets, surfing, or everyday life, produces resilience and better long-term outcomes. The conversation closes with Young's book (The Enough Equation: Wealth Wisdom, Virtue and the Pursuit of Less) as a Stoic parable about discovering one already has abundance.