"Again, I don’t really have any insightful takeaways here. I’ve just been noticing myself slowly realizing that the best don’t always rise to the top, and these are the examples that have been sticking out to me."
The lack of insight is key here, because really this isn't a hard problem at the surface. You need a compelling story, or product, that resonates with people. The more people it resonates with, the larger your audience.
Also, it never occurred to the author that DHH or Massimo don't *want" a big audience. They might want to explain their work to true fans and die hards, and not have to make it broadly accessible to the point where it could get 1M+ views. It's not about talent. It could be a choice.