Well, then he's just an asshole. I always buy my software when I can afford it. Sometimes, though, I just don't have the means, and the reality of the situation is, you have to have the right tools in order to produce the right result, and that can then raise your out of the financial squaler that you are in...which in turn, if you aren't a selfish SOB, you will support the developers of the software and buy what you used. It's a simple case of wether the person is self centered or actually thinks of others.
I pirate at times because I have no choice but to. Given that my production style is of a specialized nature, I don't tend to go for the big money pop jobs and commercial rock records (been offered, but can't stomach that shit). It's essential to be able to create the required piece, and somteimes it does require that $4,000 orchestral library in order to get a professional result that doesn't sound like it came from a casio keyboard recorded into a child's novelty kareoke cassette player/recorder.
The long and the short. If someone is an asshole, they believe the world owes them everything for free and will pirate even if they are well off. Shame on them, for screwing over the software industry when they really could afford to support it. You wouldn't have to look far to see other places in their life were they believe the world owes them everything, and I bet, allong with all the other selfish shitheads on the planet have made a great deal of lives harder or more hectic with their self centered persuit of everything for themselves and fuck the rest.
On the other hand, there are some people who do pirate, who have an ethic that whenever they have the money to buy the software, they sure as hell will. I have plenty of legitamite software that I have purchased in times of pleanty, and some that I haven't had a chance to afford legitimately, yet. Also, I often use the pirated versions to deside whether it's a piece of software that just has lots of sexy features and an impressive feature list, or actually something I'd use frequently. Time and time again, I've been suprised by the software that I end up using in a lot of my music, it's usually the ones that I don't think much of from their web site descriptions. It's not so possible to tell from using a short demo, or listening to samples of it, whether it's just gimickey ear candy or actually useful for creating unique music.
It all comes down to the fact that there are all kinds of people. Some, no matter what their station in life will be scoundrels. Look up some of the cases of millionaires who took to stealing from people and murdering people just because they wanted to enjoy the experience.... There are plenty of people who aren't of that persuasion. You're boss is just a dick for being able to afford it and still expecting it for nothing....I bet he doesn't tip his waiter when he goes to the hip resturaunt on the yuppy side of town.