Ask HN: Do you know similar essays to Paul Graham's?

Gwern has some very interesting writing on various subjects: https://www.gwern.net/index

Although his site is probably best known because of this longform article on Silk Road: https://www.gwern.net/Silk-Road

I found Aaron Swartz's weblog fantastic; at times exceeding Gram by more than a bit.

I'd second this. To use a fairly bad baseball analogy, PG hits triples most of the time, Aaron has a number of home runs and the rest are doubles.

And Aaron just has so much more. If I'm remembering correctly, he wrote an essay every day for a year at one point.

Feld Thoughts is probably closest in tenor. TechStars and YC probably started around the same time circa 2007

PG is unique, but at times I have similar feelings when reading https://www.stilldrinking.org.

To me Paul Graham is completely unique. He is really a master of words, and at times also a beautiful writer.

Another one which is close to it is this: https://sivers.org/