[moopark]

I know that languages evolve naturally, and words get repurposed all the time, but hustler? Really?.

hustler

  n 1: a prostitute who attracts customers by walking the streets
    2: a shrewd or __unscrupulous__ person who knows how to circumvent difficulties

It also happens to be the title of a porn magazine that would make Hugh Hefner blush, while you won't often hear the term 'hustler' used in reference to a female prostitute, you will find it heavily used among gay men to refer to male prostitutes.

Perhaps repurposing 'hustler' without negative connotations will work, but this is a word with a lot of ugly baggage, and the first thing I thought of when I saw it used in reference to startups: dishonest businessmen.

[Addendum] For completeness, a dip into the modern lexicon:

http://en.wikipedia.org/wiki/Hustler_(disambiguation)

  Hustler is a monthly pornographic men's magazine
  and general brand of Larry Flynt Publications.

  Hustler or hustlers also commonly refers to:
    - A practitioner of confidence tricks
    - Someone who deceives others by hustling, usually in sports
    - An American hip hop slang word for a pimp,
      drug dealer or male prostitute

[alexyim]

You're missing one definition:

  an aggressively enterprising person; a go-getter

I think it depends on audience, but I hear this quite often in these circles.

[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.