If you have been scratching your head, wondering how to sell photographs, the nightclub gig is one of my favourites. It's ideal if you want to start making money fast, because you don't need much preparation work, and it is easy to do. You do need a camera that takes decent pictures in low light, but most modern cameras can handle this easily. Experiment to ensure your camera takes satisfactory photographs in venues like nightclubs, bars and similar.
To carry out the plan you will need a small portable printer and preferably a friend, to carry it in a backpack. Other than some change in your pocket and a USB cable this is all you need. Don't worry about the idea of having someone carrying a printer all night, as portable printers are tiny and run off batteries. There are models available weighing as little as 3lbs.
Head out to nightclubs, bars etc., but don't start taking pictures until you have spoken to the owner of the establishment. Go up to them and say you want to take photographs of punters with their girlfriends and will be charging around $10/$20 a time. Say you will give them 10% and you may find that many say yes. If not, no worries - head off to the next venue until you do get a yes. Remember to dress smartly - first impressions count in this game.
Once you have permission, approach couples that appear to be having a good time, and ask them if they would like a photograph taken and printed out for $10/$20 and if they say yes, do it. Now you basically go round the venue with your friend in tow taking pictures and collecting cash...and then you go to the next venue and start again. I recommend putting your email address on the back of the photographs, as this may well create some other photographic leads for you.
While this can seem a somewhat crude business model, if you are serious about wanting to know how to sell photographs, this can be pleasingly lucrative, even more so on a Friday and Saturday. Also as this is evening work, it doesn't interfere with your day job. Be prepared for some rejections along the way - you will find that the more you do this, the easier it gets to approach complete strangers and ask politely if they want your service.
After a few weeks you may find you become somewhat of a tourist attraction, and people actually start coming to the venues that you will be at, just to get their pictures taken. This can become a growing business, and once this happens you may be able to raise your prices. Whether you charge $10 or $20 per picture will depend on you, but I recommend you base this decision on the clientele that frequent the establishment you are targeting.
Some guys can have a hard job saying they don't want a picture with their girlfriend, and subsequently this is why this method works well. Additionally, it can be quite amusing to start recognising different couples, especially when they turn up with different partners you saw them with before. This is only one of several ways of how to sell photographs - but it's certainly one of the most fun.