An excellent dissection, but took me a minute to get through it!

I really don't know what they were thinking with trying to scare off all the little indie creatives with the pivoting to enterprise stuff, who won in that strategy? And why wasn't there room for both? They could have just left the old Vimeo in stasis for those people and created an entirely new product line that'd have been better suited, especially since they were rewriting stuff from scratch anyway.

As pointed out, if you want to win in enterprise, you have to be willing to bend over backward, which is exactly what Microsoft did/had to do to get entrenched and at least part of what locked Apple out until iOS came along.

The bit about BrightCove and the competition explains so much.