Let's think of the other extreme as well: exactly the same excellent VPN service, is run by an almost-the-best-person-in-the-world who has just one small quirk that makes them not 100% perfect for you (they pat kittens not as often as you'd like them to do). Obviously there is a border between your extreme and mine, which border defines "use" and "no use" cases for you. And now: wherever this border is - should it be the same for everyone?
However the original statement:
> The CEO’s extracurricular activities are none of my business.
Basically says that no border should exist, and it makes no difference at all who provided the service as long as the service itself is excellent.
That is a fundamentally different argument that I very much disagree with.
I don't understand the point of this thought experiment. Are you trying to disqualify the idea of boundaries because they're imperfect (which is a very flawed argument) or are you going somewhere else I can't figure out at all?