It's much easier when 'upper management' is 3 individuals you can have a normal conversation with, than a hierarchical hivemind above you that does inexplicable things for random reasons.

People are also usually suddenly much more reasonable and cooperative when you're discussing something face to face with them and not through third parties :).

Even with a company of size=1, you have to worry about customers.

but those are hopefully much closer aligned to endusers than your upper management. Unless you make some ad spyware

Or anything for corporate use where the customer is a beancounter and the user is an employee, stereotypically.

Or education, where it's possibly a politician or a government beancounter and a student.