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As we all know, the key to making money on Craigslist in your copy. Sure, a great offer is important. A nice landing page will increase conversions. A free giveaway will build your list. All very true and valuable to work on. But without exception, when I go back and look at my most profitable CL campaigns, I can ALWAYS track them back to good headlines on the main page. No more, no less. A terrible offer with a kick ass headline is FAR better than a kick ass offer that no one is reading. The bad news is if you are posting frequently, and in multiple cities and categories, you have to write lots of headlines. The good news is, there are a few simple tweaks that I have found to raise CTR pretty much across the board, regardless of city, category or type of underlying offer. And if you are tracking your CL links and redirects – ( which if you are not – you are operating totally blind and most likely getting your red rear end slapped by those of us who are) you can simply measure which ad approach works best for your offers. Lets take a quick look at some easy ways to tweak your campaigns – and some live examples of my own.
1) Use Unique and Cool Keyboard Characters:
One of the very first major improvements I started to see in my CTR was using the wide variety of keyboard functions to create a more visually engaging ad. Want to know the truth? I saw other people doing it, and had NO IDEA how to get it to work. I am not proud to say I probably spent an hour trying to figure out how these folks were getting musical notes in their ad copy, and after wasting 60 minutes of my already way too wasted brainspace – simply found a nice grandmotherly figure online who was selling all 14 gazillion key combinations for 99 cents in one fat pdf. I can now say "your credit sucks" in Japanese keyboard characters, can print out much of the I Ching in small sun symbols as well. While neither of these signs you have mastered far east linguistics will help your ad copy, they will make you feel like a much more cultured craigslister - and make your headline stand out far easier than it would without them. And if you post on CL often in competitive categories, you understand this more than half the battle.
2) Indent. And use ALL CAPS. I know, I know. No one likes people who use all caps just about anywhere else…but on CL, it simply works. It's that simple. It might not next week, or next month – but right now, EVERY one of my ads that has caps and runs wider to the right side of the screen ( indented) simply does better. And visually, you can see why. Even if the copy ain't great, the eye is going to track something that stands out when surfing a sea of sameness in an otherwise crowded space.
4) Rhyme. Use words creatively. Entertain people with your headlines. Irritate them. Simply Stand out. Do NOT blend in. If you want to blend in, you aren't going to do well on Craigslist, or really anywhere else in the marketing arena. I like to rhyme, mostly because it comes very quickly and naturally to me. I'm Similar to Jay Z, just with better taste in shoes and a more liberal view on gun control. Here are some of mine:

Ho, Ho, Ho! Your Credit Score is Low! ( was going to go with "blows" but didn't want to push my luck..:-)
No More Chubby Tummy for MY Hubby!
Jingle Bells, Your Credit Score Smells – Your FICO laid an EGG! ( not my favorite – but worked!)
5) Use Alarm. Panic. Urgency.
STOP! Do NOT BUY THESE DIET PILLS, OR –
WAIT! BEFORE YOU…..
HOLD UP! I NEED TO…
Again – this works well for me, and can help with some quick copy creation when your ordinary creative juices stop flowing…You can interchange these easily, they appear "unique" for CL spam filters, and are pretty much equally effective in getting people to take a quick peek at what is so DAMN important that you had to startle them to get their attention.
5a) Shock and Confrontation.
Let's face it. You are FAT!
Be honest. Bad credit has RUINED your LIFE!

Very simply – you are going to get responses from this approach. Call it tough love, confrontational selling or simply being an asshole, you will get a visceral reaction from your intended audience ( in CL parlance this also means you will be "flagged" more often even if the ad is fine otherwise) but people DO respond to this. Think of ways YOU can incorporate and integrate this into your marketing mix and your bottom line WILL thank you for it. Remember – if you are helping people in need – occasionally rocking the boat a little bit to get them to see they would benefit from your help isn't necessarily a bad thing.
And of course, track everything. If you are using a program like gotrythis for your links, simply integrate subcampaigns on the fly to identify what kind of ad you are running for that module – ie abc.com/credit-ho , or abc.com/diet-donot, etc.
Remember, at the end of the day, 95% plus of this applies to ALL of your copywriting and magical marketing maneuvers….These are not strategies indigenous or unique to Craigslist, I do the same thing for articles, press releases ( where appropriate) , blog comments, link bait is perfect for this, and so on.
Good luck, and as always, ask questions if anything was unclear. 
Comment by Ton van Creij
20 February 2008
I tried several ads on Craigslist and in he review shows as active but none appears on the list. I think they don´accept intangible products or sites, but there are some on the list. What is the trick?
Tks,
Ton
Comment by Robert
6 March 2008
Ian. Great Post Boss!
I recently discovered this goldmine called "craigslist" about a week ago but I've been struggling to get posts up. I bought a $200 software which doesn't work at all. And then I tried posting manually but ads got ghosted even though they were all unique. I'm thinking about hiring a posting company… I think I'm ok w/ the sales copy and all that good stuff but the mechanics of physically getting the Ads Up is killing me smalls. Any tips would be much appreciated. Do you have a software you recomend? Thanks buddy
Comment by ian
7 March 2008
Hi Robert -
Thanks for your comments..;-)
I think if you take a look at some of the different posts on ghosting here, you should be able to circumvent that fairly quickly. I haven't had a ton of time to play on CL lately, but ran a whole series of ads the other day ( 50 ) that ALL stayed live - simply using notepad, a hosted image, one CL account and a live link as well. I have used several ad posting programs, and think they all have the same inherent limitations and flaws - so I'm hesitant to recommend one…although if I HAD to pick, I'd recommend ezadposter as there is a good and active forum of smart people - and the product is also good in my own experience. Good luck!