A particular type of essay that HN is an absolute sucker for — an awesome type of person that you're supposed to identify with. Paint Drip Person. T-Shaped Person. Paul Graham has also written a bunch of these, so maybe it's just in the DNA of the site. I guess the classical example of this is the renaissance man, but that at least required different fields like art and science and not different kinds of programming.
It's a certain kind of content. I might invoke Godin's Law (not Godwin, Godin): the evocation of an idea feels better and more significant if you leave it extremely vague, and draw no useful conclusions from it :) Put any of this stuff into practice and you run into practical issues, and it's way less interesting. I'm definitely a paint drip dude and it's not at all useful. In the absence of a team of cultists to do…
Both spent about two decades living in near poverty and only recently experienced financial success.
I don’t believe telling either of them to switch strategies would have been helpful.
We could infer from these two cases that “don’t give up” is the unifying factor, and that that’s helpful advice. I think history is littered with counter examples. Giving up may not be psychologically healthy (or advisable), but advising somebody “don’t give up” can still be cruel and unhelpful. Resisting the urge to give advice may be kindest.
I suspect most advice broadcast on the internet does more to inflate the author’s reputation than to help the audience. Even if this is true, it doesn’t rule out the possibility of a small quantity of exceptional advice having an outsized positive impact that outweighs the over abundance of reputation inflating advice.