While religion is on the decline in the US, Christianity is still the dominants religion, and it's a famous parable. And this is an American, English-language website; it's not crazy to think that much of the population has heard the saying.

HN is also a cyber-entrepreneur website, and if there is anyone willing to disregard that saying extra hard they're here too...

According to Wikipedia, there's no actual evidence for such a gate, so this seems like apocrypha meant to soften the message.

But given that we're talking about the man who preached "give up everything you have and follow me" and "let the dead bury their own dead" I'd favor the more radical interpretation being the most likely.

edit: Oh yeah, parable of the talents, too.