Honestly, having used both extensively at different points for years I can say that I understand his approach for smaller projects, but Typescript coupled with coding standards, makes working with large teams and large code bases 1000x better. Being able to immediately know what data is being passed where at a glance is invaluable.
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I hope I never have to work with this person. What a shit take.
There's likely a lot of reasons one wouldn't want to work with DHH. It's unfortunate because he is clearly really brilliant but seemingly fails to realize that a huge amount of software engineering involves working together with other people, many of whom aren't that brilliant.
I think the best take on this is from Rich Harris at Svelte. They are dropping it for internal Dev because they get the same feature set from JSDoc and have no build step, but they keep it for Svelte users who want TS.
Cool, Typescript is basically useless.
That's ~~bait~~ undefined.