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What this is really talking about is that we abandoned well engineered thought out platforms for piles of hacks, and superior clean languages for inferior but popular ones.

The problem with a lot of those beautiful systems is that they were neither free nor easy to use. The things that won were either or both of these.

For hardware the things that won, like the PC platform, had scale, and therefore won on price performance. A lot of the hardware mentioned here was priced for enterprise. Platforms that were only available in those price brackets and never fell in price either died or stayed extremely niche (s390x).

A second problem with the nice software is that a lot of it was not ported to the cheap hardware.

For software, free isn’t just about money. It’s also about virality. A free OS or language implementation can just be copied. You don’t have to ask permission.

The only non-free software that won was easy to use. Free is usually still unable to achieve that. People will pay for ease of use. The nice well engineered stuff, though, was usually still arcane.

I think “worse is better” can be explained by these things. Worse is not better for some non obvious systemic or evolutionary theoretic reason. Worse is cheaper, or free, and therefore has scale and can spread virally.

Linux was free. The web was free. C compilers were free and Java and JS were free. Windows and macOS and later phones were easy to use and still cheaper than those enterprise grade things.