[moopark]

I agree that it depends on your dictionary.

If a locally repurposed word like hustler has a very strong meaning outside your circles, chances are good that when you start talking about hustling in relation to business, a fair number of people are going to think swindler or worse.

It seems that a number of people like to use it as a self-description because it does have negative, edgy traits -- in the same sense of 'ninja'. Unlike 'ninja', however, 'hustler' can easily lie a bit too close to the truth.