Why didn't MSN become what WhatsApp is today? I always wondered how they could screw this up. Smartphones are perfect for chat apps, that's basically what they are supposed to be used for, and MSN / ICQ already covered a gigantic portion of the instant messaging market. Did they just assume people would stay on desktop for chatting forever?

Good question. I remember Microsoft had an app around 2010, but it just failed to gain critical momentum, maybe because people were already moving en masse to Facebook and WhatsApp itself.

The app was only ok-ish. There were some alternative apps in the AppStore. But people just preferred talking trough WhatsApp and Facebook Messenger (which was already two years old at this point). I guess people gravitated to WhatsApp because it was less cluttered and snappier, and to Facebook because it also had a proper social network in it, but I have no idea. Two years later Microsoft would kill MSN and integrate it with Skype.

Yeah Microsoft was too dysfunctional before, but they’ve improved a lot recently and are killing it in many areas

Yep. They ware the dominant instant messenger here. They would have had a massive user base from day one.

Or AOL, but maybe it died out too soon?