A good hustler must consider that–if he has nothing to lose by asking–it might be because his self worth is nothing.
That's quite a harsh judgment - I think the hustler is generally aware that they are on the losing end of the power dynamic, and that is what requires the hustle (partly to prove their eagerness/enthusiasm), but their self worth is definitely not zero as this would cause them to just shut up and not bother. I see hustle as an attempt flex muscle by the weaker person in the negotiation.