I was once having a very good day in NYC and an art-student-looking guy outside Cooper Union tried to sell me one of his hand-drawn "life maps" - he was holding a basket of little paper scrolls tied with shiny ribbons, with colorful lines drawn inside the paper scrolls - for a couple dollars, and it actually worked on me (well, I'd stopped and asked about them because I thought they were free, but he still convinced me to pay for one). People like pretty handmade things with some sort of emotional resonance (note also that I'm a girl socialized to like pretty things). It was a good hustle.

There are also people who go to farmer's markets and sell poems written on the spot on typewriters - http://www.flickr.com/search/?q=poem%20store - similarly whimsical, handmade, and suitable for impulse purchases for people out on dates or whatever. You could multivariate-test the sign.

Also check out the licensing requirements for street vendors if you haven't yet: http://www.nyc.gov/html/dca/html/licenses/094.shtml (to help make sure you know what you're getting into, and also because it has exceptions for artwork and written matter).

Thanks for the link to the licensing requirements. To comply with the law, I think we will call whatever we are selling artwork, so we do not need to get a permit. I like the poem store idea.

It doesn't matter what you sell. What matters is how you sell it.

Case in point, Joe Ades with his vegetable peelers: http://www.youtube.com/watch?v=HCUct4NlxE0

Thanks for sharing the video. That guy is an amazing salesman. It reminds about the mantra: It's not about the idea, it's the execution that matters.

Sell experiences.

I'm not sure if you've heard of Joe Ades. He used to sell potato peelers in NY and has been mentioned on HN a few times:

http://en.wikipedia.org/wiki/Joe_Ades

http://www.nytimes.com/2009/02/03/nyregion/03ades.html

http://www.youtube.com/watch?v=HCUct4NlxE0

I don't think it really matters what you sell, especially in this case where you just want to improve your sales technique. The main thing is that you sell an experience, not a product.

This reminds me of stories of kids setting up lemonade stands in Times Square, and even making a lot of money before getting shut down by the cops.

I can't find the exact news article, but this one is close ($200 profit/half day!):

http://www.dnainfo.com/20110628/midtown/kids-set-up-lemonade...

I think that you could get a lot of mileage by selling unique trinkets. Imagine taking a Escher style moebius ring and creating an actual ring or a necklace out of it (imagine doing it with flat links to form the necklace, and they all have connections to one another at a varying gradient, so that you can create that moebius strip) [ interesting link to set you up http://www.cs.technion.ac.il/~gershon/EscherForReal/ ]

If you think about it then there are tons of amazing geometrical shapes out there that would make amazing trinkets, and why limit yourself to pure mathematics? Imagine creating a trinket that represents plasma captured in a magnetic bottle. That would be beautiful if you can get it just right.

This will be challenging, artistically, to pull it off (perhaps you can use a 3D printer), but if you do I want one. (yes, I have weakness for such trinkets)

I'm starting a clothing company/website called http://beerfarmer.com and could send you some socks. I'm in montana and selling these primarily to mountain bikers and active lifestyles but would love to get some feedback from Times Square. Still working on product shots but...

https://beerfarmer.3dcartstores.com/Adventure-Socks-_p_13.ht... contact me through the site if your interested.

Last year I was in NY doing some accounting and spent some time walking about.. One good con I fell for was some guys passing out demo CDs of thie mixtapes - sure I'll grab one as a souvinier! The guy offers to sign it and add your name - haha ok sounds fun. Turns out his fee for signing is $5! An it has your name on it too now. turned out a better souvinier than I expected. (just an anecdote, not a suggestion you learn how to street hustle)

I got hustled with that today haha!

They hand you a CD and tell you they're trying to get their music out there, etc. Then ask for donations. I felt like a sucker but the lesson was worth it I suppose.

FYI, a guy running this CD hustle (according to police)--in Times Square, as it happens--got himself killed in a gun battle with a police detective in 2009 (in brief, the guy ran after the detective asked to check his paperwork and then started shooting).

Lots more details:

http://www.huffingtonpost.com/2009/12/11/raymond-martinez-ti...

I am curious: What was an the CD? Was it empty?

Music I assume, haven't actually checked it out

Extremely bland hip hop

I am sorry that you got conned, and I hope that did not ruin your NYC experience. We aim to be white hat street hustlers.

Not at all! I enjoyed it - coming from Tokyo New York was a great refresher on human interaction outside of Japan for me.

Turn it into a competition with your friend. And don't be afraid to embarrass yourselves (remember it's a game/competition) in terms of advertising a little louder than normal. What helps also: Ask your potential customers about the pitch afterwards (what they thought about it, whether they liked it) - nice side effect: you get to meet awesome people who'd like to help you.

Theres a guy here in Tokyo who does dramatic readings of manga for people... He's amazing and has been doing it for years but I imagine it would work just as well with older cheesy marvel / dc / Archie comics. The key is he gives it 100% and then some.. You could probably get the comic books for dirt cheap

Food/snacks (health laws?) Plastic rain coats / umbrellas local knowledge?

We took food/snacks off the table because it requires health permits. Plastic rain coats / umbrellas are weather dependent, but a good idea.

I understand that experience is experience, but wouldn't you say that there are better places and alternatives to spending time trying to sell things in a 'tourist' environment?

I agree. We spend a lot of time working on developing products. We just want a productive outlet when we decided to take a break.

There may be more "productive" things to do, but it sounds like their trying to actually have some fun too. It sounds like a great combo to me.

@murtza They do things like this in the Apprentice all the time. There's probably some good ideas there.

Thanks for the tip. I will read some episode summaries of the show to see what they sold.

run around with an ipad and offer them to "get a real NY friend" on fb for just 5$. if you can sell that, you can sell anything.

I'd be slightly concerned that somebody would snatch the iPad out of their hands and run. :p (It reminds me of this: http://www.dnainfo.com/20110531/downtown/iphone-thefts-on-su... - "Thieves are snatching the popular devices right out of straphangers' hands, especially in lower Manhattan's subways.")

Some other ideas I brainstormed: 1)Roses, 2)Guy Fawkes Masks, 3)Create and sell a guide. Maybe a "Guide to NYC Public Restrooms"

well, its still warm in the sun, while at the same time heading towards winter. So maybe chestnut flavored ice-cream? Food vendor license may be too much trouble compared to hand made tourist kitsch.

Water, umbrellas, maps, photos.. oxygen

Oxygen... What an idea. At Six Flags Magic Mountain, they sold oxygen with a sign that read: "BENEFITS OF OXYGEN". They must have sold out of ice cubes in Alaska.