Most don't though.
Most come from upper middle class families.
They live 'Grad School Life' until they are successful.
Meaning: ok, nothing phat or fancy, but they don't have any real trouble or risk.
Of course - many do struggle for a long while.
I think they should buy what they want ... but they shouldn't be showy about it.
Don't drive your Ferrari into work when there's a layoff :). Or ever maybe.
EDIT: there's quite a lot of data to validate that richer kids are more likely to be successful founders [1]. I'm not indicating that this is always the case of course, but it's pretty common.
I worked for a while at a Fortune 50 and the kids we saw coming in as interns were really well prepared - I also noticed a pattern - their parents were Doctors, CEOs, high level government officials. I'm not saying they didn't earn the positions, but there's no doubt that their status helped, moreover, they already knew how to behave properly in a corporate/professional setting. I had no idea, that's not something my parents could teach me.
Two of my 'rich kid' interns went on to found major companies, one of which there's 100% chance you've heard of and probably 80% chance you've used - the other just raised $50M.
Coming from a remote Wyoming ranching childhood, I will claim that signalling can be learned, and that most if not all customers, VCs and bankers I might talk to are shocked to learn that I was not brought up just like them.
It's no different than lawyers or doctors, though. Every group has tribal signaling to help them identify if a person is in or out of their group. Learn to speak the language. Heck, even poor people (like me!) can do that.
I think the problem is that they are still working for the investors, having sold them the dream. Because they are also acting as CEO, they are still on duty to the investors to create an exit.
They haven’t “made it” yet, unless you consider raising investment as the goal. But it isn’t. Until you’ve made your investors a great return, the point of the article is to show some modesty.