That's still a questionable situation. If a subordinate asks out a superior, how does the superior know if they're actually interested, or are just hoping for preferential treatment? And even beyond that, peers of the subordinate, once they find out about the relationship (and of course, they will find out), may be uncomfortable with a peer of theirs having the ability -- whether real or perceived -- to bend the boss' ear to that degree.
If this entrepreneur who got hit on had propositioned McClure instead, I don't think people would have minded that.