I thought that "skin in the game" just means that you feel the consequences of your actions, and are (maybe) forced to learn as a result. I think that doesn't work well for single catastrophic events as you describe because single mistakes are deadly/ruinous/etc. IIRC Taleb is focused more on the field of managing risk for shared-decision-making and aligning incentives, but none of that rules out total failure etc, it just means that everyone bears the consequences.