Yes, both Keith AND BillO are extremely insecure. Both are crybabies and whiners, but I'll have to say I truly enjoy watching BillO throw fits. It's hilarious.
With Keith, I just roll my eyes and say, "Oh brother". People really don't give a damn whether or not he got fired, laid off, quit or whatever. Or that he got paid for it. The fact is, both Keith and BillO like to toot their own horns. They like to try to make themselves look as if they are all that. But let's get back to reality. Neither one of them are worth spit.
BillO is just plain insane. And Keith truly is crazy. If he wants to get up there and explain what happened 7 YEARS AGO then let him show his craziness.
As for Keith's money situation? It's not so much the money itself as it is the principle of the matter. He's been going along trying to convince people that he's this upstanding moral citizen when in fact he's just a loser.
Unfortunately he's been able to woo a lot of people that he wouldn't hesitate stabbing in the back if he thought it would make him come out smelling like roses.
When he said he doesn't have three friends? He wasn't kidding. Even though it sounded like a joke, it wasn't.
I suspect those who become his "friend" learn early on that a relationship with him would be volatile, and that their life would mean nothing unless it had something to do with him.
In other words, a friend to him means you would have to spend all your time kissing his ass and doing exactly what he wants you to do.
So yes, he is very secure in his insecurities. And he doesn't mind showing it. But he does it more subtly than BillO.