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Re:Ask HN: Books/podcasts/blogs discussing Microsoft's cultu... by stevenwliao on Monday October 08, 2018 @07:51PM (#18172285)
Try Stratechery, written from a tech strategy perspective.

https://stratechery.com/company/microsoft/

This article is a great starting point: https://stratechery.com/2018/the-end-of-windows/

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