In this thought-provoking and entertaining episode of The Silicon Dreams, host Preethy Padmanabhan sits down with Roshan Cariappa—former VP of Marketing at Vymo and host of The Startup Operator podcast—to explore the bold ideas from Skin in the Game by Nassim Nicholas Taleb, part of the Incerto series.

Roshan brings his signature wit and sharp insight to unpack Taleb’s core message: accountability only matters when people have something personal at stake. He shares how this principle applies to leadership, startups, and everyday decision-making—revealing how embracing uncertainty, taking meaningful risks, and aligning incentives can drive more ethical and impactful outcomes.

From making your message clear enough for your grandmother to understand to finding the genius within, this conversation is both insightful and surprisingly fun. Whether you're an entrepreneur, a builder, or just someone questioning the rules of the game, Roshan’s perspective will challenge how you think about risk, responsibility, and success.