If you’re looking for an easy and rewarding “in” to buying and selling online, there is no better option than Craigslist. Far easier than eBay, Craigslist has an enormous potential and is only getting better as more and more people continue to use it every day. As a student with an uncompromising taste in good (and often expensive) design, Craigslist was one of the few venues available to me for furnishing my apartment. Through much trial and error, I’ve developed a keen sense of how to buy and sell through Craigslist. I’ll share my secrets that will help everyone from the first-time amateur to the seasoned vet make better listings and find better items all in time to help you save and earn money for the holidays.

Buying:

The Search
— The first point to make regarding buying on Craigslist is realizing what is and isn’t available. Although Craigslist is very democratic in its presentation of various classified categories, the markets has quickly shifted to favor specific items. For instance, Craigslist is excellent for furniture, materials, and technology, less so for decorative items, and even less so for things like books and clothing. If you’re looking for the latter it would probably be better to search on eBay, Etsy, or Amazon.

— Depending on your location, stock can change very quickly — the core structure of Craigslist being similar to the blog model where the most recent classified posts are at the top and get pushed to the bottom. Checking often can yield great results as the chance for getting the best deals are often soon after they are posted, rather than finding them hours or even days later. If you’re looking to do some heavy buying (or are searching for a very specific piece), I recommend setting up a daily routine at least 3 times a day (morning, noon, night) to check all the new listings. Patience is a virtue.

— To prevent aimlessly meandering about the countless results, it’s best to switch on the “show images” option in the top right-hand corner. This will display a tiny thumbnail preview of the images within the post. Also, keyword searching is your friend. Search often, with a wide array of search terms which could be applicable. For instance, remember that you could search “filing cabinet” or “file cabinet” and return separate results depending on the wordage used in the auction. This is something you should keep in mind when selling as well.

— The “free” section is a mixed bag. Some people swear by it, others refuse to bother. Many will post items available on the corner and will not hold them for you since they understandably don’t want to be bothered with reservations and just want the things out of their house. Incredible deals can be had, however, if you are quick to the draw and are lucky enough to live nearby house or have a car. Many free things given away are often good enough to be turned for a profit.

— If the item that you’re looking for is very common (IKEA Malm bedframe) or very broad (Mid Century coffee table), you’ll have some choosing to do. Don’t assume that the first item you see is the only one available. This will give you a better opportunity of finding the least used, least expensive, most convenient, etc… product available. If I come across the same item multiple times, I created a simple Excel document listing the item, where it is located, how much it is, and any distinct qualities about it or the seller itself. This way I am able to compare all qualities side by side rather than try and remember them as I went around searching. This step may seem trivial for a $10 side table but will certainly pay off when you’re looking for a high ticket item.

— Another thing I like to do is keep a bookmark folder of posts I’m “watching.” If you see something you like but don’t have the money available or don’t wish to pay the asking price, wait it out. I scored my white Victoria Ghost chair this way. Someone posted it once, it got lost in the monotony of Craigslist, and I emailed them a month later with a much lower price and they accepted.

The Purchase
— Once you select the item you want to purchase, you’ll want to initiate contact with the seller. This is potentially the most crucial moment of the entire sale as first impressions are everything. Remember, a seller is not bound by any rule stating who they must sell to. Even though you’re the first person to reply that doesn’t mean the deal is sealed. Respond in a calm and collected way. Believe me, I realize this can be very hard if your holy grail comes up out of nowhere for a fair price. Explain yourself and your intentions as completely, yet briefly as possible. Many sellers are busy people and don’t wish to dedicate much time to this deal. If they see that you’ve written a novel, they might be more likely to disregard your email. So be eloquent and to the point. Say who you are, state your interest in the item, confirm how much you’ll pay, and when you’re available to pick up. If the post asks for a phone number, provide if. If not, ask if they’d like one. Many people choose to deal over the phone as it is quicker than playing email tag.

— If you’ve come across a fairly common item, you could use this as an opportunity to bargain. This is one of the best qualities of Craigslist — there is rarely a fixed price. Bargain early if the price is higher than comparable posts, or late if the item hasn’t sold (particularly if the seller keeps reposting it to bring its position back to the top of the first page — I’ll talk more about this later.) Of course you want to be considerate when bargaining so as to not offend your seller.

— Try and appeal to the seller if you think you have a particular trait worth mentioning that would help you stand out from the others. As an example, out of total desperation I’ve responded to more than one ad featuring a modern design classic, totally out of my price range, such as the Aeron chair. I explained that I was a design student with a meager budget, was in love with the chair and could offer x amount. Sure enough, the owner was an architect who, despite receiving numerous emails about it, sold it to me for a lower asking price because I was a student of design and he knew I would probably appreciate it more than anyone else. So be truthful and be yourself. There are a ton of kind people in the world who might be lenient with the price if you just explain your story honestly.

— Before planning to pick up an item especially if you must drive there, always double-check the address and time and never go without a phone number. I’ve heard horror stories of people planning to meet someone somewhere, with no phone number, and the seller just never shows up. Communication is key. Never get in your car without a phone number and guarantee that the seller will be where they say they are.

— Being professional and truthful is a huge aspect to this entire process. The Craigslist community has been known to oust poor buyers/sellers within the classifieds section in order to warn others of potentially detrimental transactions.

— Lastly, and I hate having to say this, but it is always good to exercise caution when visiting a stranger’s house (or vice versa.) If you feel safer having someone tag along, by all means do that. The majority of buyers who have come to my apartment have brought a friend just as a precaution and I think that is a very smart idea.

Selling
The Ad
— Deciding what to sell is the obvious first step. As I mentioned before, some items do better than others on Craigslist. I always choose to sell my tech and my furniture on Craigslist but make more money on clothes and books through eBay. Craigslist is an excellent way to sell off a dumpster-find or even turn a profit on an item you bought there. Many times you can find things in very poor shape. After a decent cleaning, the item will look much better and often commands a higher price on the listings. I’ve made literally hundreds of dollars by fixing up trashed furniture or low price items and reselling them days later. One of my favorite stories was finding a mid-century task chair out on the sidewalk as trash. I picked it up on my arm and biked it home — I must have looked completely crazy. I cleaned it up, made a beautiful listing out of it, and sold it for $75. These kinds of opportunities come up on Craigslist on a daily basis. Keep your eyes peeled for these potential moneymakers as you search.

— Your ad can be distilled into two main components: the description and the photos. I cannot stress enough how crucial good photography is to the success of your ad. I’d argue it is even more important than the description itself. Including good photographs is an easy way of making your product stand out among the competitors. I recommend shooting your items with a DSLR camera. If you don’t have one, try borrowing one from a friend. If you don’t know how to use it, you can find very simple step-by-step tutorials online. Unfortunately that is out of the scope of this post. If you can’t secure a DSLR for taking your photos, at the very least try to take them in daylight. Natural lighting in your photographs will make your item look more true, clear, and inviting. Another helpful tip is to “stage” your items. Just as you would stage your home to sell, staging your belongings in your house can make them that much more attractive to potential buyers. Don’t be afraid to gussy it up with items you wouldn’t normally decorate with. Look at catalogs or websites for staging tips such as CB2, West Elm, or Design Within Reach. Remember to get multiple angles as well as any unique features (or flaws — remember, it pays to be truthful) on your item. Combine all of these photography tips and your posts will jump off the page to potential buyers. It also has a secondary effect that tells the buyer that you care about your items and aren’t liable to screw up the sale. These little things work wonders when trying to sway a buyer between your item and someone else’s.

— The second component is the description. Before you dive into the items you’re selling, get all of the boring information out of the way first. Say where you’re located, when you’d be available for pickup, whether or not you’ll accept best offer, if you’re open to trades, types of payment you’ll accept (typically only cash), if delivery is an option, etc… never include your phone number inside the ad itself.

—When you describe your items you’re going to want to break it down two ways: bullet-point comments up top and explanatory text in sentence form down below. For instance:
// Eames Rocker
// White
// Fiberglass
// Dimensions
// Price (compared to retail if you’d like)
Then describe why you’re selling it, unique features (or flaws) in the design, how you got it, etc… This is your opportunity to really sell the item in words. Remember that Craigslist’s search feature will not only search the title but the description as well so throw in as many keywords as you can (within reason) which would return your page to a relevant search request.

— Adding the option for delivery is very helpful. If you can deliver, it will increase your buyer pool dramatically (especially if it is a large item.) Don’t be afraid to charge a fair fee for your time/gas. I’m an avid cyclist and offer free delivery on my bike if the contents fit in my bag and the buyer is within a certain distance of my house. Include the delivery option in the title itself.

— A very important step when making your descriptions is to include the photographs you took inside the description itself. This makes your post stand out much more than others' and lets the readers really have a chance to enjoy/examine the items you have for sale. Now, how do you do this?
You’re going to need to host your images on a free image server. For those of you who don’t know how to already to this, imagehost.org is a favorite of mine. Upload your images and copy their direct HTML link. In the description box, you’re going to want to use the HTML tag: <*img src="url link here”> (without the '*') to place your image. This will actually insert your pictures into your description. Remember, also include one image in the Craigslist image uploader. This will allow Craigslist to display your photo as a thumbnail when buyers are browsing with the "show image" option enabled.

— A second tip worth mentioning is good if you plan on listing multiple items as a kind of virtual garage sale. These posts work very well by the way. You can draw a reader in for one item and as they read your post, will discover others they otherwise wouldn’t have found! Try utilizing a Google Docs Spreadsheet as a way of keeping an updated list of what is and isn’t available or any other applicable information that you’d like potential buyers to see. If you haven’t used it before, it is free for any Gmail user and works/looks very similarly to Excel. You can make it available for public viewing and share the URL in your description. I’ve seen people use this method when they were selling off their entire apartment before they moved. It was a very helpful way to centralize all the data together.

— Choosing a title is equally important. I always like to use correct grammatical capitalization for titles and describe my item as directly as possible. For instance: “White Eames Rocker — Authentic Mid Century Design.” Be mindful of the location field. I like to put the neighborhood within the city in which I’m living. It helps buyers get a better sense of exactly where you are rather than the incredibly broad city name.

— Once you believe you’ve crafted a successful post, go ahead and submit it. Craigslist usually takes a little while before the post itself goes live. Typically, weekend posts tend to do better than weekday posts and I always like to post mine around late-afternoon, when people would be home from errands but before they head out to dinner. People tend to repost their ads on a daily basis. This is technically against the rules. I might re-post mine about twice a week (once on a weekday and once on the weekend). Many sellers simply rely on search terms and you should too.

The Sale
— Now you can sit back and get ready for the emails to come in. It is very important to check your email regularly. I recommend using an automatic mail updating service like Microsoft Outlook or Mac’s Mail application. This will let you know nearly instantly when you have a potential buyer emailing with a question or an intention to buy. Respond as quickly as you can to all emails. People hate waiting especially if it is an item they want badly and can get it from someone else. Expect some bargaining and lowball offers. If your item is popular and you have multiple emails, explain to the lower bidders that you’ll only accept full price due to interest. You’d be surprised how many lowball offers shoot up to asking when they realize they’re in competition with another buyer.

— One other point worth making about Craigslist buyers is that some are outright crazy. If you get a frantic email, poorly written in all caps, demanding to pick it up within the hour, I’d probably ignore it or simply explain that it has already sold. Use your best judgment as to who you’d like to deal with. Spam is also a problem with Craigslist. If you list a high price item, you’re almost guaranteed to receive spam. It is often easy to distinguish spam from the real thing as they are all very generic and broad (never referring specifically the item in question.) To alleviate this concern, you can request that potential buyers submit a telephone number in their email or make mention of the item specifically.

— When you decide on a buyer and make arrangements to meet, be very sure you adhere to those arrangements. If an emergency comes up, let the buyer know as soon as possible. I always like to confirm the day-of when a buyer is coming to pick something up or I’m going to drop something off. If you’re dealing with furniture like IKEA, it is good to have the tools present to dismantle it (if the buyer is coming to you) or to assemble it (for an additional charge) (if you’re going to the buyer) just incase they don’t have their own. Little things like this can help prevent an easy sale turning into a nightmare later. Of course be courteous and help load/unload items. If someone is paying in large bills, don’t be afraid to double-check their legitimacy against a light or invest in one of those bill markers to authenticate them. If you’re dealing with a very high priced item, I would even recommend going through Paypal. If the buyer is coming to you, they could pay before they leave, through their mobile phone, or could use your computer. And if you go to them, you could simply have them pay from their home computer. This insures that all the money is absolutely there before you trade off the goods.

Here are some more helpful tips for using Craigslist from the Unplggd Archives:

• How to Sell Your Junk on Craigslist Through Photos
  
• Craigslist Buy v. Best Buy
  
• Craigsphone: Craigslist at Your Fingertips
  
• The Secret to Getting More Money for Selling Your Old Tech

If you have any specific questions I would be happy to address them in the comment section.

[2nd image: Flickr user Alcomm, 3rd image: Flickr user Stewf, 4th image: Flickr user orphan girl, 5th image: Flickr userStewf licensed under Creative Commons]