William Henry Gates III made his best decision on October 28, 1955, the night he was born. He chose J.W. Maxwell as his great-grandfather. Maxwell founded Seattle's National City Bank in 1906. His son, James Willard Maxwell was also a banker and established a million-dollar trust fund for William (Bill) Henry Gates III.[1]
However:
Several writers claim that Maxwell set up a million-dollar trust fund for Gates. A 1993 biographer who interviewed both Gates and his parents (among other sources) found no evidence of this and dismissed it as one of the "fictions" surrounding Gates's fortune. Gates denied the trust fund story in a 1994 interview and indirectly in his 1995 book The Road Ahead.[2]
So I'm inclined to think it's not true, although it does seem a fairly wide-spread story.
But at the same time, Bill Gates did come from a rich family, so he wasn't going to starve if Microsoft didn't work out.
Is the existence of a trust fund actually relevant for the story? Whether there was one or not, as you already said, Gates didn't have to fear failure. I doubt the family would have let him live in poverty on the street if he had failed. I don't think it changes the narrative. But it's bad that - if you are right - the wrong story is out there because it gives a convenient escape to get sidetracked and be able to ignore the actual message.
No single guy with no family to support has to fear failure though. It only becomes a fear once you have a wife and children to support - but that's why it's generally accepted that you first get financial stability before starting a family. Some people choose differently as people are always free to make terrible life choices - but they need to face the consequences then.
Even someone with a $1mil trust fund can make terrible enough choices to end up homeless.
He discussed the whole plan with his family, and they agreed on it. Secondly, he studied in Harvard, so his family had at least decent amount of money by default.
And then, the thing is that family who was struggling the whole time, won't agree on dropping the best university with wonderful perspectives for some kind of crazy (at the moment it was very "crazy").
People are not "just risky" by default, they are influenced heavily by their life, and as someone mentioned here already, a lot of rich guys came from pretty decent living families, who can afford to fallback if something. For instance, a lot of world travellers, who try to live differently, actually have some passive income, property of just loads of cash, just in case something will go wrong.
Do you happen to have a source? I'd not heard this and was curious as to the amount.