Arguably, Nokia is a good example of "money and connections won't save you if you persistently go astray".

I liked Nokias, I even programmed for Symbian OS, but boy, that was one convoluted system. The UI was pure hell, badly documented, error-prone and had to be tailored to every device out there (of which Nokia churned out a lot), unless you wanted to risk bad artifacts.

They also LOVED to introduce major compatibility breaks.