I've been on HN for a similar amount of time, and I've seen the same shift in opinion on pg, but my conclusion about why is different.

From the mid '00s through early '10s, pg was a much more grounded, down-to-earth person. Sure, he'd sold Viaweb and was doing quite well financially, but he was still working hard and was very close to the startups he was advising and was funding. I attended Startup School back in 2006 and thoroughly enjoyed it and thought it was a genuinely useful experience, even though I never went on to start a startup.

Fast forward to today: pg's net worth has gone up a ton, and he's moved on to bigger and different things than his old roles at YC. He's not the same person he was 20 years ago (who is!), and his writing reflects that over time.

Much of his old work still resonates with me (I go back and re-read my favorites from time to time), even though I'm a bit more cynical (or perhaps just more realistic) about startups these days, but most of the new stuff he writes feels out of touch. Plus he sometimes tries to write about things well outside his wheelhouse, and gets much of it trivially wrong, which tends to turn me off.

The thing that really made me shake my head at this particular essay was that he used Facebook and Airbnb as examples in an article about how it's possible to make heaps of money without cheating. Just... wow.