I think what makes so much of his material stand the test of time, is that he was focusing on things that had already prevailed over time back then, for better or worse.
And he was focusing on things actually intended to help his readers get the best of what was likely to matter most to them.
2024 (157 points, 101 comments) https://news.ycombinator.com/item?id=39555598
2020 (128 points, 83 comments) https://news.ycombinator.com/item?id=23725867
2013 (174 points, 154 comments) https://news.ycombinator.com/item?id=6327021
2012 (81 points, 42 comments) https://news.ycombinator.com/item?id=3624830
2009 (50 points, 40 comments) https://news.ycombinator.com/item?id=608431
And he was focusing on things actually intended to help his readers get the best of what was likely to matter most to them.
So a lot of it matters a lot still.