But.
I'm not sure what the bigger point is, here. Should we be okay with piracy as long as the pirate is using it for self-betterment? Do games count for that? What about pirating Game of Thrones episodes? (Or, to take a wild leap: Is it cool for a kid to steal a car if he learns how to be a mechanic from it?)
Today, I do feel there are some motions towards providing better access to software and hardware in poorer parts of the world. Which is great. And, to be frank, the quality of both cheap hardware and open source software is insane relative to twenty years ago. So, again, I'm not sure what Vlad's bigger point is.
If the point is to justify piracy, I think he only does it in the very narrowest of ways: Considering the state of technology in the 1990s, piracy enabled people in poorer parts of the world (and kids in wealthier parts of the world) access to the growing information technology industry. I'm not sure that argument exactly holds in the same way today.
Finally, Microsoft can survive a fair amount of piracy. But not every software company can. What happens when this "it's cool because I'm using it to educate myself" stance kills software companies? Or game companies? Or media companies? Is that better for everyone?
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EDIT: I'm not equating the act of stealing a car with the act of pirating Windows. I am merely wondering about the general nature of morally justifying a crime based on it being done for self-improvement. If we say it's okay in a case of software piracy, are we okay with it in other contexts?