I think it goes back a lot further than Twitter.

As someone who hung out on IRC way back in the 1990s (and internet-knew Limor from Adafruit back before her handle was Ladyada) I associate this writing style with the culture of a lot of the hacker-related IRC channels I used to hang out in back then.

Some of the same people from that era did in fact turn out to be tech founders and maybe that's how it got carried over into the Twitter-verse, but it predates that.

Explanation: https://calteches.library.caltech.edu/51/2/CargoCult.htm

You’re right. Sam Altman does this and others repeat it like people used to wear black turtlenecks.

Not just tech founders. Jeffrey Epstein writing is just atrocious. Like how does anyone habitually use a commas ,, like this?

I've heard it referred to as a "flex," basically doing something stupid to rub it in that you can get away with it.