This is what I believe in from my experience in starting businesses. Much of the "stomach" to take risks and taking them multiple times depends on how "lucky" you were to begin with. People around you will see risk if you don't have money or opportunity if you do, so expect their support accordingly.
The danger is ignoring the tendency of egocentric bias in these articles[2]. Successful people assume that their values and ethics are what led them to success, when that may not be true. Though that then bears the question: who do we listen to for advice on success? Rich people? Scientific studies [3]?
A thread I read on a previous hackernews post (coincidentally about Paul Graham, another founder of ycombinator) perhaps puts these ideas in better words than I [4]
[1]: https://journals.sagepub.com/doi/abs/10.3102/003465430750034...
[2]: https://www.youtube.com/watch?v=3LopI4YeC4I
[3]: https://journals.sagepub.com/doi/full/10.1177/23328584198577...
Yes, it is. I see it all the time. Scott Adams wrote a book about it entitled "Loser Think".
BTW, everybody is born with disadvantages. But everyone also has advantages. Like being born in the US (instead of, say, Venezuela) is a big advantage.
I have a family relative, one of the most lazy people in the world, that some day found herself rich. How? Hard work? Business value? Education? No, she discovered she had a grandaunt and that she would be the heiress of three 300000EUR houses, plus half a million euro. The scene seemed out of a 90s love comedy, if only it weren't tragic.
So, if you start with money, you end up like WeWork. You may renew your money but nobody likes you.