I hated the days when you constantly had to switch web browsers to get pages to render. I'm glad it's rare now, because we didn't give up on the hope of open systems.
Mark might have lost the battle to have HTTP/2 encrypted by default, but at least when Let's Encrypt came out, it still worked in all browsers.
Would we have been better to just give up and have lots of walled gardens instead? I don't think so. I'm glad we have WWW.
Personally I don't think XMPP failed because being open made it slow to adapt. I think we're mostly stuck because ICQ, AOL & MSN just got there first.
I don't envy being in Moxie & OWS's position of figuring out how to make this work. I'll add opinion and some of it harsh, though I'll reserve criticism until I've built something as awesomely globally deployed as Signal.