I saw this same screen and thought it was for mobile people on laptops who had limited Internet connection times. It has nothing to do with MSFT corporate culture in my view.
When your installed base is measured in the hundreds of millions things work a little differently from when you're a startup with 200 users.
It just shows that Microsoft has been around for quite a long time. I don't see what is so funny about that. I am not a Microsoft fan, but I think they were successful in a time when not everything was as easy as it is today. So laughing about them - I don't know how many people really have the achievements under their belt to be in a position to do so.
When your installed base is measured in the hundreds of millions things work a little differently from when you're a startup with 200 users.