"I guess I see what’s supposed to be funny here, Rob, but I don’t think everyone will. As the man behind an awfully high-profile startup, I don’t think this is likely to attract any beneficial attention to you, and may very well attract some negative attention. Even if this is meant in good fun, I’m not sure it’s in your best interests."
Jokes are funny when they punch up [at people with more power/status]; they're asinine when you punch down. This is an excellent satire, which should have become obvious when the robot shows up...
He's neither punching up nor down, but in: the optimal direction to punch.
This post, however, does seem almost too good, as if it's the greatest PR coup of all time.
He's pretty much parodying himself here, which is what makes this so effective.