William Henry Gates the Third had a trust fund before he was born. His downside risks for anything he chose to do in life were completely nonexistent. Same with Zuck. Same with Spiegel. Same with 99% of the entrepreneurs HN idolizes.
Here's some light reading:
http://qz.com/455109/entrepreneurs-dont-have-a-special-gene-...
http://philip.greenspun.com/bg/
EDIT: Removed potentially inflammatory line, which went as follows: "Just a bunch of rich kids trying to prove a point to their parents".
This is definitely a personal opinion, but one that has merit if you examine the evolutionary psychology of parent-child relationships. The conversation is a bit in depth, but please understand that I was not trying to simply fire off an ad hominem. I was instead trying to hint at the incentives which drive an already rich child to strive for more wealth. For the vast majority of us who have to work for a living, such behaviors seem confusing. Only upon deeper analysis do the pyschological incentives for such individuals begin to make sense.