Is Gabe really that irreplaceable? The way he runs the company (flat-hierarchy), it’s mostly self-governing – the truly defining characteristic of his leadership is his willingness to be as hands-off as possible. A like-minded successor or even governing council could probably quite effectively handle things in Gabe’s absence.

Well… regardless of that: nothing lasts forever, but that’s no reason to assume that things will change for the worse. Gabe seems to put a lot of deliberate thought into his actions, so I wouldn’t be surprised at all if he has already taken care of preparing for a smooth and faithful transition away from his leadership when the time comes. Who knows, maybe they’ll even do a better job than Gabe could?