This conversation with the brilliant David Roberts kept circling back to insecurity, not the dramatic kind, and not financial, but the quieter feeling of being a little outside things. Of not quite knowing how to perform confidence, how to bluff, how to talk the talk. David reflects on how that lack of ease stayed with him even as his career advanced, and how, in hindsight, it may have saved him. Rather than hardening into certainty or ego, that self-doubt tempered him. It kept him oriented toward home, toward family, toward listening and learning. He has a philosopher’s mind, always turning ideas over, always curious, more interested in learning than arriving. What emerges is a portrait of a different kind of hero: someone shaped by vulnerability, softened at the edges, and oriented toward connection rather than conquest. In a world that rewards certainty and performance, this felt like exactly the kind of voice we need.

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