No, I really think you're mistaking this. Some of the easiest ways to become wealthy - or let's say "financially independent", because it's a more clear-cut term - are doing useful and well-compensated work, that is definitely not "great work" in the essay's sense. Think dentists and most doctors and lawyers, and also lots of different kinds of "businesspeople", including software engineers at big successful companies. Think about the people you see on a private golf course that they have a house next to; those people are all wealthy, some of them inherited it, sure, but many of them just plugged away at lucrative jobs and saved and invested well. That's not what the essay is talking about. It is a much easier way to achieve financial success than attempting to do "great work" in the essay's sense.
Personally I have had a tendency to waffle back and forth between the ambition to "great work" and the ambition (and at times, necessity) to do lucrative work. And for me, thus far, the two things have been almost entirely negatively correlated; I have given up the lucrative path to seek something I hope will be "great", or given up the "great work" path to seek something I know will be lucrative.
To bring this back into the lens of the article, I do think that for people who are not already financially independent, this can / should / is just one more constraint in the search through this space of "what should I work on". Some "great work" is lucrative while a lot is not. Financially independent people have the privilege to choose freely among the two kinds, while the rest of us have to focus on the lucrative kind to at least some degree.
If anything, I view that as a slight deficiency and bias of the essay's sense. Here's how I'd phrase it based on what's worked for me, which is "Learn to fall in love with expensive, poorly-solved problems." Not all expensive poorly-solved problems are poorly-solved, but for the ones that are, focusing your curiosity on them -- why they are expensive, why they are poorly-solved, what state of the art looks like, how it could be improved -- that is a surefire way, in my view, towards doing great work.
Now, that may not be considered great work by the essay. But I might read the essay with my assumption around its editorialization -- which is that it's to some degree an attempt to describe "here's what I'd like to invest in." I'll bet you today (and especially in the future) that if I tested the author's revealed preference about investing in "my" thesis of great work, while our stated preferences might differ, our revealed preferences would align.
Caveat that this is this is all conjecture given that I've never directly interacted with YC's investment thesis.
Yeah we're sort of just debating the implied definition of something left purposefully vague, but I don't read this particular essay as an investment thesis thing at all. His motivating examples are pretty much all musicians and theoreticians there's no investing in those things. To some extent those examples are metaphorical of course, and I'm certain he is thinking of at least some entrepreneurs as having done "great work". But I still take the essay more at face value that it isn't primarily focused on the kind of wildly lucrative "great work" that makes a good investment.
Personally I have had a tendency to waffle back and forth between the ambition to "great work" and the ambition (and at times, necessity) to do lucrative work. And for me, thus far, the two things have been almost entirely negatively correlated; I have given up the lucrative path to seek something I hope will be "great", or given up the "great work" path to seek something I know will be lucrative.
To bring this back into the lens of the article, I do think that for people who are not already financially independent, this can / should / is just one more constraint in the search through this space of "what should I work on". Some "great work" is lucrative while a lot is not. Financially independent people have the privilege to choose freely among the two kinds, while the rest of us have to focus on the lucrative kind to at least some degree.