Thirty-five years back, I went to work as the fourth person in a start-up (that's still in business) and loved the fast-paced environment of a start-up life. Fifteen years ago, I went to work for "BigCo", and while our group was essentially an internally funded start-up, I hated the politics, especially as we acquired other companies and tried to integrate their software products into ours.
The good news is that succeeding at three of the four start-ups left me with enough stock options to fund (my share) of my next start-up with cash. While it's looking like I may not see a return on that investment, the product was certainly something the industry needs/needed. As a small boot-strapped company, it's almost impossible to move an industry.
I'm currently working at a university and we've tailored the culture within our group to be much like you'd find in a start-up (the political machinations of a university can however be brutal). In any case, I think I have a couple more ideas that could be turned into start-ups and enough working years left to build a couple more start-ups. I can't think of anything that's more fun.
In contrast to you, I came from an upper-middle class family with a stay-at-home mom and a go-to-work dad. Things were comfortable when I was at home but I'd have never asked any of my relatives for money to create a start-up and my parents were far more risk averse than I (originally they mildly disapproved of the risks I was taking but seem to have realized I always "left myself an out" so that in the worst possible outcome, I could take care of my wife and kids).
So it might be true that most kids these days have the money to be entrepreneurs, I say it was definitely in my genes. (As an aside, in the '80s I think most of the start-ups I saw were people who were risking almost everything to get started because they had a vision - it's much easier to fail if there are no consequences).