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Taleb literally did say that you should never board a plane on which the pilot isn't onboard (such as a drone plane). Unless this was intended to never make you board an unethical plane, he does believe in some sort of insurance related to "skin in the game".

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I would never get on a plane with the pilot anywhere but on the plane either.

But, the point of skin in the game isn't that it reduces the risk, it's a moral issue of who bears the risk. Skin in the game means you don't get the upside without the downside risk. That's it. It's not some magical pixie dust that makes people act rational, or follow safety protocols.

The pilot is more often than not the cause of the accident. Without a pilot airplane would have to be designed to a much higher standard. Right now the pilot is an unreliable fallback

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