Paul Graham is overrated. I believe almost every developer goes through a phase where they are enamoured by his writings, and thanfully, they grow through them when they get into the real world. Perhaps your time will come soon too.
I am honestly curious whether you think PG's opinions on Python 12 years ago also "make no sense whatsoever" and are "Purely subjective speculation at best". Speculation about my professional growth is irrelevant.
The total market cap of companies coming out of YCombinator is a pretty staggering number.
I don't say that as proof Paul Graham's writings are all true and should be accepted as gospel without question. But it's not credible to suggest Paul Graham doesn't understand "the real world" of software business.