How to Be a Hustler
To be a hustler, or someone who finds creative ways to make money off of others, think of something cheap you can buy and then sell for more to those in your community. For example, you can buy candy in bulk and then sell them at school for a buck each. Instead of pushing a product, you can also provide a service that people need like washing windows or cleaning gutters. If you can get paid beforehand, then you can put in as much effort and time into the job as you want. Since the main part of a hustle is making someone feel confident that they're getting a good deal, make sure you look reliable and friendly and that your product or service looks legit. That way, you'll be more likely to get business from other people.
Think about your talents. The classic hustle, depicted in movies like "The Hustler" and "The Color of Money," is definitely billiards, but it's possible to develop a convincing and effective hustle operation with almost anything competitive or sales-related. Take your hobbies or talents and think of ways to turn them into a full-time job. If you're a great card player, table-top gamer, or a master of online shoot-em-ups, there might be a way to make money by convincing people you know you can beat to bet on a game with you. Play lots of pool. Don't try to hustle anyone at a game or sport you're only good at. If you're going to try to hustle, first spend time developing that skill and making sure that you can easily beat almost anybody you play. Buy something cheap and sell it for more. If you've got the gift of gab, consider developing your interpersonal talking skills into a convincing sales operation on the side. Find something you can buy for cheap and sell it on eBay, craigslist, or in person on the corner —just keep in mind that, legally, you may be required to have a permit to do so. Think of something the people in your community are constantly in need of and sell it at a profit. The classic grade school hustle is to buy candy in bulk and sell the items for a profit. A buck a bar isn't a bad deal for Snickers if you're stuck in school all day, and you can get it for a lot cheaper at the store. Take specialty orders from your customers and build your reputation as the Candyman. Hand towels, cigarettes, plain white t-shirts, ear-bud headphones, ice scrapers, and pre-paid cellphones are items available for low prices that you can sell for much more. Selling concert or sporting event tickets on the day of the event, also known as "scalping," can be a good hustle. Get on the pre-order sights and pay the lowest possible price for the early tickets and then sell them closer to the event when the demand is higher. If you're good at making a unique specialty item from cheap materials, like fake leather gauntlets or artisanal beef jerky, make it your thing and hawk it. Be your own boss, investing most of your time and effort into making it look stylish, hip, and upscale. Market it well without necessarily bothering to make it exceptionally well. Consider moving to "Portland." Consider more elaborate sales like car parts, stereos, and furniture from outlet stores or yard sales. Many furniture stores and clothes boutiques will purchase new items from outlet malls and then sell the items at a regular or inflated price at their own store or online. Do the same thing yourself, underselling the boutiques but still priced to make a profit. Provide a service people didn't know they needed. Shoveling snow, shining shoes, washing windows, or cleaning gutters can be quick money-making gestures with almost no overhead but your time and effort. Volunteer to take down Christmas lights in expensive neighborhoods and recycle them for a cause that you make up. Instead of recycling them, sell them in another neighborhood next year. Hang out in the restroom of an upscale restaurant, offering cologne samples, condoms, or other sundries that you provide. Contact the restaurant first and offer to split the profits, or don't. Hustle tip: get around your customer's hesitation by starting in on the task while you're still selling them on it. If you're halfway through shining someone's shoes by the time they get a chance to say no, they'll be compelled to pay for it. Photography hustles can work similarly. If you have a good, professional camera, take it to public events and take pictures of couples and try to sell them on the prints. If they resist by saying, "We didn't ask for a picture," you can say, "I thought he gave me the signal! I have to pay for this film myself and my boss is going to kill me!" They'll assume you're part of the event, even if you're not. Hustle online. All you need is computer access and the Internet to start hustling online. Owning a sponsored Facebook or Twitter page dedicated to a particular meme or cause is a good way to generate revenue without necessarily doing anything. Likewise, there are lots of opportunities to take on editing, writing, and graphic design work if you've got an aptitude for writing or computer programming. Register with an essay-writing website marketed to college kids and volunteer to do homework for pay. Make subtle changes to your old papers and assignments from college and pawn them off to people willing to pay. Start blogging on a particular subject and dedicate lots of time to crafting your voice, page, and fanbase. Always build confidence. Hustles are based on confidence and are sometimes even called "confidence schemes." Even if you're working on a swindle of epic proportions, the person buying needs to feel confident that he's getting the better end of the deal. If you're working a card or pool hustle, you need to look bad. Constantly ask to be reminded of the rules to the game you're playing before betting. try to get the person you're hoping to scheme to suggest playing for money. Lose the first game to get a sense of their skills before going double-or-nothing and bringing out your full bag of tricks. If you're going to work a sales hustle, you and your product need to look great. No one will buy your ice scrapers or pay you to rake their leaves if you look like a hustler. They'll pay you if you look like a reliable, friendly, and enterprising sales person. Even if the tires you're trying to sell back to the truck driver you just recovered them from are going to deflate any second, they'll need to look like they're ready to go. Build your operation. If you've got a lead on a bunch of cheap imitation ear-bud headphones and need to get rid of them by selling door-to-door, consider bringing in some cheap labor. Get some kids from the neighborhood to do the selling for you and pay them back with candy or other kid-friendly currency, as long as you live in a state that does not have strict minimum wage and underage work permit regulations. If you're running a pool scheme, it helps to have a partner to play with initially and make you look bad. The two (or more) of you can develop more complicated schemes. Consider hiring free labor. It may be less than moral, but if you've gotten paid ahead of time to do some yard work for a business or residence, you could hire out the work and promise the workers payment afterward, or after the next job. If you tell them this job is like an interview, you can pull a Tom Sawyer and disappear conveniently, keeping the money without doing of the work. Advertise your hustle. If you're "the guy with the leaf blower," consider making business cards or flyers in the autumn when the leaves start falling. Don't let people forget that you're there to do the service or provide the product that they want. Even if you're a card shark or a pool hustler, eventually--if you're good enough--it will help to get your name out as "someone to beat." The challengers will be knocking at your door. Alternatively, it might be a good idea to keep your hustle on the down-low. If you're selling low quality items under the premise of quality, you might not have many return customers. Being difficult to find would be a good thing in this case. Work in a team. Anytime you're considering parting someone with their money in what could be a less-than-honest way, it's a good idea to have back-up. Work with at least one other person if you're selling things on the street to help keep the money, merchandise, and your person safe from other hustlers eager to exploit. Never hustle your teammates. Even if you're in the habit of pulling a fast one on people, make sure you're honest with the people you bring into your schemes. Know the laws. Is what you're selling legal to sell in the place that you're trying to sell it? Is gambling allowed at the particular pool hall you're trying to work a scheme in? Questions like this need to be explored before you're waist deep in a hustle. Even if you plan to continue hustling anyway despite the laws of the land, it's important to know the rules so you know how secretive to be about your schemes. Decide if the punishment is worth the potential benefit. Also be aware of the potential tax problems you may run into. You may end up making a lot of money beating people at Halo 2, but how are you going to declare those winnings? Decide before the IRS comes knocking. Keep moving. Working a hustle one too many times in the same place is a recipe for trouble. Get your show on the road and keep moving to friendlier locations full of new suckers for you to hustle. This will help keep your hustle lucrative and safe. 
Think about your talents. Buy something cheap and sell it for more. Provide a service people didn't know they needed. Hustle online. Always build confidence. Build your operation. Advertise your hustle. Work in a team. Know the laws. Keep moving. 