Delicious was for a time at the cultural nerve center of the web, and I think had the potential to be something like a twitter or a reddit if stewarded correctly. I like to think there was an alternate reality where Yahoo didn't run itself into the ground, and took its properties: delicious, flickr, tumblr, its massive userbase across fantasy sports, groups, news, messenger, geocities and answers, its email service,…
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.