> I cringe at past-Jacob’s naiveté. It’s been incredibly demoralizing to discover....

I don't think he's reached the end of his road to cynacism; maintaining the moral high of looking for a utopia requires not spending any time assessing the evidence presented by reality. If he has complaints about the tech industry, stocked full of utopianists, he's in for a rude shock in the rest of the world if he keeps thinking about work in moral terms. The economy is a material system that optimises material results. The best outcome is making people you like materially better off (which can be easily done in tech, FWIW), but there are always going to be side effects because the world is messy and competitive.

A fun challenge is to come up with a set of moral principles where most people aren't enabling evil. There is a reason that sociopaths tend to rise to the top, principled people don't get much support and are going to struggle with the actual impacts of what they do.