We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten.
Still some of his pessimism has been spot on. Linux is Unix and RISC-V is, well, the fifth RISC from Berkeley which was even then only codifying some principles Seymour Cray laid down (now with Cray vector instructions!).
But LLVM is more pliable and experimental (and slower) than GCC. Didn't see that coming. No one even remembers Netscape but Chrome and Firefox are not simply Netscape.
He's dead right on the over emphasis on measuring. I never even read the measurements section in papers. I'm only interested in the ideas. That said, recent conferences attach a badge to a paper which submits a verification artifact. That's useful, especially if I really want to dig into the paper.