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?
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.