Taleb's writing sits in this weird space between practical philosophy and applied skepticism, and it can be a bit polarizing. If you're coming from a more traditional philosophy background, 'The Black Swan' is probably the most essential. It tackles epistemology and the limits of prediction in a way that feels like a direct challenge to Plato's forms or Kant's categories. He argues we live in a world dominated by the highly improbable, and his whole concept of the 'ludic fallacy' – mistaking the sanitized randomness of games for the messy randomness of life – is a philosophical idea you can chew on for ages. It's less about formal logic and more about the philosophy of how we know what we think we know.
That said, 'Antifragile' might be the book with the most actionable philosophical core. The idea that some things benefit from disorder, stress, and volatility, rather than just resisting them (robustness) or breaking from them (fragility), is a powerful lens. You can apply it to systems, economies, personal health, even moral character. It reads like a series of connected philosophical essays or meditations, jumping from Seneca to modern finance. It's messier and more personal than 'The Black Swan,' and his rants against certain academics can be grating, but the central metaphor is incredibly sticky. For someone who wants philosophy that feels grounded in real-world chaos rather than abstract thought experiments, it's a compelling, if uneven, entry point.
I'd steer clear of 'Fooled by Randomness' as a first book for a philosophy-minded reader. It's more focused on behavioral finance and the psychological errors we make. The philosophical underpinnings are there, but they're not as developed. 'Skin in the Game' is another one that's heavy on philosophy—specifically ethics, symmetry in human relations, and responsibility. His rule that 'you should not harm others with words if you aren't willing to harm them with swords' is a brutal, ancient-kind of ethical principle. It’s a good follow-up if you've already bought into his style and want to see him apply it to social and political theory.