I think OP was using "politically incorrect" in its original definition - i.e., speaking in a way counter to what's politically popular/accepted by the elite.
Which in Startup L. Jackson's case was definitely true - he called out a lot of the Valley's cultural myopia, excesses, and failures in a way that he would have been unable to do without the pseudonymity or pretense of satire.
Unfortunately the word has also been co-opted by some to mean "liberal" or "progressive", which is a shame.
Wikipedia: In the early-to-mid 20th century, the phrase "politically correct" was associated with the dogmatic application of Stalinist doctrine [...] In the 1970s, the New Left began using the term "politically correct."
Thereafter, the term was often used as self-critical satire. Debra L. Shultz said that "throughout the 1970s and 1980s, the New Left, feminists, and progressives... used their term 'politically correct' ironically, as a guard against their own orthodoxy in social change efforts."
Err, not really, the "boomers now in power" are the ones complaining about an excess of political correctness. See Donald Trump and his supporters, Fox News, UKIP or Tony Abbott in Australia.
> speaking in a way counter to what's politically popular/accepted by the elite
> Unfortunately the word has also been co-opted by some to mean "liberal" or "progressive"
Because what is tolerated by the elite and what is called "liberal" or "progressive" are two completely separate things, in particular with respect to academic elites, right.
Which in Startup L. Jackson's case was definitely true - he called out a lot of the Valley's cultural myopia, excesses, and failures in a way that he would have been unable to do without the pseudonymity or pretense of satire.
Unfortunately the word has also been co-opted by some to mean "liberal" or "progressive", which is a shame.