Let's say his aging mother died and he continued to cash her Social Security checks for a year, to continue to pursue his dream, would you consider it unethical? The federal government certainly has the money, and he is tenaciously pursuing his dream.
I agree with you that there are situations in which it's ethical to steal from someone who can afford it, but what parent said was that the latter condition doesn't guarantee it to be automatically ethical, implying that grandparent's assertion that the theft was ethical because AOL could afford it was fallacious.
On the other hand, an obviously talented young developer who is starving in Silicon Valley may need to take an internship that pays $80K+ per year.
I'm not seeing the parallels.
Anyway, it is more complicated than the arguments I have been witnessing here today and I just regret that I am not in good shape to give adequate voice to the idea that society needs to come up with a more enlightened means to address ..the whole kit and kaboodle.