It's easy to confuse the two groups and think a distinction doesn't exist.
It's not at all complicated to get smart idealistic people who fuck up whether in Wall St or SV, to doubt themselves, get defensive and then cynical. There are lots of idealists who have turned cynical over their careers. And it's very beneficial for all kinds of parties, to strip that idealism away and just harvest the smarts using guilt and shame, fear and doubt.
And it works very well on those who aren't clear about their Values and Needs, or those who don't have experience with failure.
Yet even after all that, you will find two different groups. Why? Because there will always be idealists who don't turn cynics, even after fucking up.
There is nothing straight forward about recovering from fuckups. For some it takes time to see their mistakes. Some are able to openly process or talk about their mistakes (which society loves to then exploit or pass judgement on). And others get highly defensive and come across or get painted as oblivious to their mistakes. These different routes add to the impression of hypocrisy (that everyone likes to take a dig at and laugh about).