Ironically Neumann's latest startup is funded by a16z.

As mentioned in the article, it's a spectrum, not a dichotomy. What you're describing seems to be on the very extreme end of ask culture.

The “trick” is that there are only three bananas in the last bunch and four in the others. Likewise there is a single coconut in the last equation. It appears this could be interpreted as 1 + 10 + 3.

That's actually half a coconut. The smaller one is ambiguous. Is it supposed to be another half or a quarter?

Ohhh. I even looked for stuff like that and didn't notice it. Brains are weird, man.

Appears to be referencing this piece from Paul Graham:

https://paulgraham.com/submarine.html