And the truth is if the 'Bill Gates' had to deal with this frustration himself (most likely let's say he doesn't he has people who deal with it for him when he needs something from another company or his own) he'd implement changes to keep users happier. Noting of course that you are always going to have a segment of people that will both get angry and have edge problems.

Did or does 'Bill Gates' ever actually try to be a regular user of Microsoft support actually waiting in the call queue on hold for 10 minutes to an hour and even getting disconnected?

Does anyone at the company (in a position to order improvements) ever do this?

(This applies to many companies obviously 'bill gates' and 'microsoft' are just placeholders.)

I think it's underestimated the amount of psychological pain that some of the software (of Microsoft and other companies) has caused people over the years.