>Why do these otherwise very smart people always seem to draw these kind of shortsighted conclusions?

The obvious conclusion is they aren't very smart. Consider that Cluely guy: the best returns on lying are to be the only one lying while everyone else tells the truth, so why does he want to promote lying? Partly dumb ragebait marketing (this isn't going to attract talent... and while it has given them millions in startup funding, how long are the sharks giving him the money going to do that?) and partly he just isn't very smart.