I don't think it's the CEO's job to be a test pilot. I think that's pretty crazy actually.
I know someone who is a test pilot. He's trained a long time to do it. You want someone in the craft that is an expert at both piloting spacecraft and the engineering of the craft. Musk is certainly no pilot and the job of CEO does not require you to have those skills.
It could be argued that since these systems are fully automated that you don't need anyone with special skills there. But being a programmer I don't trust software for every situation. So I sure think if you are going to put a person on it, they should be able to intervene if needed. There should be a purpose to their risk.
[1] https://thumbs.dreamstime.com/b/postage-stamp-mongolia-circa...
To be honest I don't think the current "pleb" generations dream about space conquest anymore (I'm part of that "pleb", of course), people have gotten accustomed to the idea that everything relatively close up there is either very dark of very cold or both, so why all the fuss about some piece of rock located in those dark and cold places?
Unless we discover some new laws of physics and the accompanying new technology I think we should put firmly in our heads that's no way for us as a species to get passed our solar system, so maybe we could better use the "space exploration" resources for something closer to home.