Hustler can mean a lot of things. For many people, it’s a pejorative term.
In the 1993 rap hit, “Juicy”, Biggie Smalls talks about how he was forced to hustle on the streets in order to support his baby daughter. So for some, a hustler is a criminal.
When I was in third grade playing soccer, my coach used to scream at me to show more hustle during practice because I was so lazy. This is my personal negative association with the term, of being forced to hustle at soccer practice when I could have been at home playing video games on Saturdays (I had different problems than Biggie).
But today I love the word hustler. In fact, it is one of the greatest compliments I can give to someone. In the startup world, a hustler is someone who doesn’t let fear get in her way. Even when she’s in over her head, lacking a certain skill or network, she puts her head down, learns what she needs to learn, and succeeds no matter what. This is a resourceful character trait that I look for in all people I want to do business with.