Speaking as somebody who's been there, I'm really concerned with this "poor changes your mind" thing I'm seeing. Buddhists manage to live and be happy not having much at all. For the vast majority of history, great men lived in conditions much worse than the average poor person in the western world does.
I agree that many rich people do not understand poor people. Likewise, many poor people do not understand rich people. But when people say things like "So your startup doesn't work out, why don't you just go live with family", they are not simply showing that they don't understand your situation. They're trying to point out: what's the worse that could happen? I've been homeless, I've lost everything I've owned. You go through a lot of crap an either you sit in the corner feeling sorry for yourself or you start thinking "So I could lose the house? It's not the end of the world." Doesn't mean I'd do it lightly, but I am in control and I have the power to make that decision.
I really don't care who has a private jet or has never worried about food or shelter. Moreso, I find worrying about those things is a good sign my head is in the wrong place for actually making me a better person.