1. Niceness - a coworker decided to just randomly not show up for work (not WFH, just disappear occasionally). I took it to management, and was told we don’t want to hurt his feelings.
2. Bureaucracy - I left yahoo to go to Facebook. At Facebook, if you needed a server, you would go to an internal tool, slide a slider and click a button. At Yahoo, you had to take a proposal to a committee led by a cofounder, and then be repeatedly shot down until you finally persevered.
I remember chatting with the Meebo founders about some of this. They didn't really have an answer to why AIM, YIM, and MSN Messenger wouldn't block them beyond it being bad for their networks. On how they'd make money, I don't remember hearing any interesting answers. They never really figured out the money thing and ended up getting acquihired by Google.
The did have a crazy-impressive web UI for the mid-2000s; for a while, that know-how was probably their most valuable asset. The need and the market still (and have always) kinda exited, but the players changed a lot in the last 15 years. One of their business ideas was to pivot into a commercial support chat app. People use them today, so maybe they were before their time, or maybe B2B was never in their DNA.