If you tie up your self-esteem to money you're screwed if your bank account dries out. If you tie up your self-esteem on something internal, like knowing you can make things happen you become independent from the external world for happiness.
A woman who doesn't care unless you're loaded is a shallow, selfish and spoiled gold digger who WILL disrespect you. Don't you want a woman who likes YOU and not your bank account? Come on man, raise your standards.
You can have money and easily be regarded as a scumbag, money does not guarantee status. Status is gained by socializing and showing personal strengths, not financial strength.
@devilkingx2 That's a risk. Better just let the past be past about that, it might work and there's a great chance it might backfire.