When we think CEO we need to think “shareholders.” Including potential shareholders as in Reddit’s case. I think sometimes we are so focused on our feelings about a “big boss” that we forget the CEO is merely an avatar for the investor point of view in a business. They answer to the board of directors who represent or are even made up of shareholders, and they are usually paid in such a way to motivate shareholder benefits, like with stock instead of a high salary.

And when we think “shareholders” we need to think “loan money.” That’s how you get to be a shareholder. You plunk down some cash to float the business.

Therefore, to really be CEO-proof, an entity needs to be fiscally independent and never need an advance of cash to keep going. It must be entirely bootstrapped, paid-as-you-go, with no one standing to gain a whole bunch or lose a whole bunch by its failure or sale. That’s kind of a lot of needles to thread when you’re building something big. It can be done but we have to know what game we’re actually playing and not get distracted by “fuck The Man” sentiments. This is about cash.