It can mean both, it's entirely down to context. To me it means someone who simply works harder and incessantly compared to others when used in a work context.

It can mean both, it's entirely down to context. To me it means someone who simply works harder and incessantly compared to others when used in a work context. The guy who puts in the extra time/hours/learning/whatever to out "hustle" their peers. In small business circles in Minnesota where I grew up it was pretty universal - those that that were known to "hustle" were revered. Example would be two lawn care companies where the owner of one would be working dawn to dusk and then spending 2 more hours distributing fliers, where the other guy knocked off at 4pm every day. The former would be known as someone who has some hustle, and you'd want to work for that guy over the latter. Of course it also has the swindler meaning as well - street hustler, etc. Plenty of folks in my life describe themselves as having a "side hustle" and they certainly are not doing anything illegal or immoral. Just instead of going home to veg out watching TV or whatnot, they are pursuing more productive activities and that is how they describe it. So to me - if someone came up to me and described themselves as a hustler I would default imagine someone who is more motivated than most, and is always looking for opportunity no matter where that may come from. It's an interesting word, it seems!