My core point is that there are people like DHH, like Massimo, who should be getting way more views on their videos, given the quality of the content they're producing and what they've done to promote that content. Do you disagree with that?

What do you mean by "... who should be getting way more views... ...Do you disagree with that?" (To provide context around my thoughts as I write, I'm thinking of the phrase "the purpose of a system is what it does".)

I'm thinking there's at least two meanings with at least two different ways to interpret. 

First, you could mean "I have an understanding of the system that leads me to expect a different distribution of popularity by viewcount. I have an understanding of the system. Good content -> high viewcount. It should do this. It does that. Do you disagree?" 

Second, you could mean "I have an understanding of meritocratic justice such that the distribution of popularity as judged by viewcount is unfair. Good content -> high viewcount. Life should be this way. It is that way. Do you disagree?" 

If neither of those hit the mark or if anyone has alternatives, I'd like to know.

For the first interpretation, "do you disagree" can't really be applied to your understanding of the system. You understand it the way you do. I suppose a similar question that might be more appropriate could be "How might the system differ from my expectation such that I am surprised by this behavior?" A brief response to that question would be something along the lines of YouTube's purpose having to do with money, algorithms to keep people viewing and clicking on ads, what makes something viral, etc...

For the second interpretation, that might be a long-winded philosophical topic that I expect could be summed up with "Yeah... that sucks."