I'm happy for them.
I've gone so far as on-prem sometimes and its "fun" for awhile but then becomes a headache.
I really love Digital Ocean's droplets too.
Let's be honest - new waves of CTOs are guys coming with pure dev background. Managing self owned infra, even rented servers is something out of their wish/ability/knowledge, it's an territory of Unknown. From their perspective, potentially saving $1 million per year doesn't worth even trying to step on that territory (which is a good decision by my common sense).
Bit of stretch from "in theory Linux on laptop is cool, but who knows how will I deal with issues, there - I'd better stick for using Mac, which provides me clear path - buy new model or replacement and I'm golden".
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And of course they [CTO/C-level guys] better not to talk to that not-a-fellow-dev-guy, wearing beards and wearing sweaters.
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For lonely dev ("indie"/"solo" developers) companies, what DHH says is not applicable of course - their spending likely too small to have savings of that scale.
That's great news. Someone else's computer is increasingly becoming...not cheap and AWS et al are turning up the cranks on their products for lock in.