The problem is that CF operates in a highly dynamic environment and you can't really do that if the minds of those hundreds of developers relied for the major decision making on a key individual.

This is the key individual paradox: they can be a massive asset and make the impossible happen but if and when they leave you've got a real problem unless you can find another individual that is just as capable. Now, I do trust JGC to have created an organization that is as mature as it could be, but at the same time it is next to impossible to quantify your own effect on the whole because you lack objectivity and your underlings may not always tell you the cold hard truth for reasons all their own.

And in this case the problem is even larger: the experience collected by the previous guru does not transfer cleanly to the new one, simply because the new one lacks the experience of seeing the company go from being a tiny player to being a behemoth, and that's something you can do only once.

I've always been of the opinion that without JGC Cloudflare did not stand a chance, irrespective of those hundreds of developers. And that's before we get into things like goodwill.

And of those hundreds of developers you have to wonder how many see the writing on the wall and are thinking of jumping ship. The best ones always leave first.

I would not be surprised at all if this whole saga ends with Google, Microsoft or Amazon absorbing CF at a fraction of its current value.