An equivalent but probably equally not-the-real-explanation argument would be that we've gone from an era of opportunity into an era of oligopoly as the internet titans have emerged and so the "coolest kids" who everyone cargocults have gone from being fast-growing startups to members of the big-5 elite. Kind of the same as his argument just with detail on who his "people" are and why, but it changes the implications.
I think it's more as he touches on that the two are converging. I think eventually some sort of pluggable typing will win (the "proofs" on your system won't be a single compilation pass but maybe different typing for different parts of the system, and specific proofs run between compile and runtime as the two blur), which will look more like gradual typing.