The beauty is the simplicity. On vacation with some friends? Spin up a new groupme for the week. I can't see it remaining this easy if skype starts taking advantage of "integration points".
And based on some announced usage numbers from GroupMe a few months ago I imagine Twilio was/is making good money from them alone…
My guess is that Microsoft had no involvement in this purchase and is basically winding up with GroupMe as a party favor. Pretty nifty party favor, if you ask me.
Yet I feel we have way bigger ambitions... I wonder sometimes if raising investment sooner was better