Ah, don't kick yourself too much, inev.
Money knows no logic, money is completely arbitrary, there's no reason to it.
You can work your ass off your whole life and have nothing. Or you can be the laziest most worthless son of the bitch in the world and if you were born into it or if you won the lottery, you can be completely fuckin' rolling in it.
It's a system rigged from the start to only allow a few people to have a whole lotta money.
It's okay. It's not failing to not have money or, at least, it's as much a failure as it is to never be hit by lightning. Dumb luck.
Dumb luck or theft, the only paths to money.
A logic about finding the right lady can apply to money, too, though:
The key to is to get yourself into a place where you are happy with yourself with or without it.
Only then could it find you and find you in a positive way.