Maybe it's An American Thing, but as I grew up and participated in school sports, our coaches often told us to "hustle" -- I don't think they intended for us to defraud or swindle anyone, or to break any laws.

The full phrase is "always be hustlin". That does have a certain context. Not necessarily fraud, but certainly cutting corners, winning at any cost, etc.

See Glengarry Glen Ross for something very similar.

So did I, but outside the context of sports it still mostly means scamming people and/or generally earning money illegally to me. Or maybe a dance.

I don't think I ever saw/heard it used in its startup culture sense until I was in my late 20s or so, probably on this very site (and no, I didn't grow up in a place where "hustling" in the sense of scamming/dealing was common) so the scamming/defrauding/dealing/etc. meaning is what sticks with me. Definitely colors my perception when I see it used for other things.

It's just A Word Meaning Different Things Thing; hustle can mean 'hurry' or something similar to 'sprint,' but it can also mean a side gig that gets you a bit of extra income. The typical connotation is with under-the-table stuff and contraband-y stuff in prisons, though, so you might not expect to hear someone talk about their 'new hustle delivering newspapers.'

Uber is currently running ads on Pandora advertising driving for Uber as "the ultimate side hustle".

When I was a kid in the 80s, it was totally normal for our gym teachers to tell us to "hustle" when we were running, lining up or doing some drill. I'm not sure about the dependable part, but working hard and moving quickly are absolutely what the word has meant to me since I first started hearing it.

Yah, same thing struck me as incongruent.

Hustling in workplace would more likely mean "thinking out of the box and wearing multiple hats". On the street it typically means "doing anything for a buck, including ripping people off".

I think hustle/hustling has some context:

Street hustler is one thing.

Hustler the mag was another.

Hustle to get ahead is yet another.

So same word or root word in different syntactical contexts can have somewhat different meanings.

For those of you arguing about the defintion, here's relevant definitions from Webster:

https://www.merriam-webster.com/dictionary/hustle

": hasten, hurry; you'd better hustle if you want to catch the bus"

"b : to sell something to or obtain something from (someone) by energetic and especially underhanded activity : swindle; hustling the suckers / an elaborate scam to hustle the elderly"

I grew up in Houston where hustling is a word that is heavily used in various contexts. In my experience it has a dual meaning of working really hard and also doing anything for a buck. I've heard it used either way and both.

In America, using the word "hustling" in this context means to work diligently and to do what is needed to complete a project. Similarly, a "hustler" is someone who works very hard and constantly at something.

Certainly not in the part of America I currently live in, where "hustling" means ripping off or defrauding someone.

I actually literally heard it a few hours ago while watching The Wire, where someone is playing pool, his partner walks in and asks him "yo, you hustlin'?".

I was a bit taken aback when I came across that verb in the article.

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!

Yes - of course hustling in the context of pool takes on that meaning.

You can cleave things apart, yet you can cleave things together. Words have different meanings depending on context.

Look at the actual definition of the word Hustle in M&W. The way hustle was used in the article was a more common usage of the word than as a con.

transitive verb

1 a : to crowd or push roughly : jostle, shove had been hustled into a jail cell with the other protesters

  b :  to convey forcibly or hurriedly grabbed him by the arm and hustled him out the door — John Dos Passos

  c :  to urge forward precipitately hustling tourists from one museum to the next

2 a : to obtain by energetic activity —usually used with up hustle up new customers try to hustle up some tickets to tonight's game hustling up some grub

  b :  to sell something to or obtain something from (someone) by energetic and especially underhanded activity :  swindle hustling the suckers an elaborate scam to hustle the elderly

  c :  to sell or promote energetically and aggressively hustling a new product

  d :  to lure less skillful players into competing against oneself at (a gambling game) hustle pool

intransitive verb

1: shove, press

2: hasten, hurry you'd better hustle if you want to catch the bus

3 a : to make strenuous efforts to obtain especially money or business our quartet was out hustling … and we knew we stood good to take in a lot of change before the night was over — Louis Armstrong

  b :  to obtain money by fraud or deception

  c :  to engage in prostitution

4: to play a game or sport in an alert aggressive manner She's not the most talented player on the team, but she always hustles.

My experience has been that it almost always has that meaning, unless the context is 1) a sports coach talking to players, or 2) HN and related startup culture. I'm not sure why startup people latched so strongly onto a word that's got very negative connotations for lots of people, especially when attached to making money.