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I think the success of Azure is really impressive give how technically poor it is.

There are stated costs, and real world costs. It wouldn't be hard for Azure to be far better than AWS on some metric, say better free support, or I guess better paid support too.

Is this the driver?

My guess is the impact of the poor tech is quite low if your scale is small and you are not all that technical yourself. A good option for smaller less Eng focused customers.

Steve Ballmer stepped down in 2014. If we're giving credit to CEOs for things that happened while they were CEO (which isn't really valid), Azure was launched in 2010 and Office 365 was launched in 2011, both during Ballmer's tenure.

Bingo.

Microsoft as IBM is a horribly outdated take.

Because of MS, they helped me love desktop apps again: VSCode, Outlook, Edge, and the ever so controversial Teams.