Craigslist is heading down the long, lonely, winding road to Irrelevant Land, a sad and lonely place where Internet companies go to spend their retirement years before they ultimately die.

How it all began.

In 1995, Craig Newmark started the service that would become the scrappy, idealistic non-profit that brought local newspapers to their knees by playing Robin Hood; they ran off with the classified section and gave it away for free. What started out as a simple email list between Newmark and his friends has since grown to become one of the most valuable properties on the Internet and the leading classifieds service in any communication medium. Now Craigslist has become so massive and popular that they are no longer able to effectively manage the community that uses and abuses it. I believe this is causing its gradual demise.

Perhaps I am just resentful.  On the 5th of February, I posted one of the over one million classified jobs ads that will be posted on Craigslist this month. Last Friday night, while my wife and I were shopping at Target, my phone buzzed as I received the email that I knew would eventually reach my inbox: “flagged & removed“.  I was not surprised. Every single ad that I have ever placed on Craigslist has been removed because it was flagged. The email went on to mock me: “Approximately 98% of postings removed are in violation of craigslist posting guidelines. ” That is their official line. It is pretty hard to believe, though. Anyone can flag a post for removal on Craigslist; you do not even have to be logged in. There are three types of posts on Craigslist that should be flagged: miscategorized, prohibited, and spam/overposted. Once a post has received a certain undisclosed number of flags, the “offending” post will be removed. I am not sure why my ad was flagged for removal. They do not share that information with you, and there is no accountability for the person doing the flagging. You are just rejected like Forrest Gump looking for a seat on the school bus and left to figure it out for yourself. They are kind enough to give you a link to a forum where all of the school bus rejects gather together to try to figure it out why they did not get a seat. These people do not know any better than you why your ad was  removed or why their ad was removed, but at least you can commiserate together.

I do not place all the blame on Craigslist. I can not imagine what it is like trying to run an organization that is processing over eighty million new ads every month and has almost 50 million unique visitors on their website every month with a staff of less than 30 people. “Why doesn’t Craigslist hire more people?” you might ask. Because their only main source of revenue comes from apartment listings in New York City, job ads in a selection of cities, and ad for therapeutic services. So, because of their small size they depend on the community that uses the site to police it.

Newmark said in an interview with Wired “Just by being good guys, we’ve created a culture of trust and fairness.” Unfortunately, there is an inherent problem with that. When someone is selling their used futon they are not trying to make a profit. They are just trying to get rid of it and get a few bucks for it. If all Craigslist users were like this there would be no problem. However, when a company that is trying to make a profit uses a site, whether to sell products or to list a job opening, they are trying to make money. Many companies are not going to be fair or trustworthy. They are going to do everything that they can to sell their product and eliminate their competition. So, since the company knows that they can get away with it they will indiscriminately flag every competing ad until they are all removed from the service. Don’t believe me? That’s OK. I did not believe it either until I searched for “flag craigslist ads.” There are literally millions of sites that explain how to exploit the Craigslist flagging system to give your ad the focus of attention by making your competition disappear.

So what does that mean for the person trying to sell their used futon? It would not surprise me if they get that all too familiar email in their inbox letting them know that they need to look for another seat on the bus. They will probably feel like I did the first time one of my ads was flagged for removal; I first felt embarrassed, then I felt confused and then I got angry. I was just trying to sell my 1993 Tomos Moped. I made sure that it was in the right category. I did not post it more than once, and I certainly can not imagine why it would be prohibited. I reposted the ad because I decided I must have been in that other 2% of postings that were removed because they were wrongly flagged. I later discovered that a local motorcycle dealer was eliminating all other ads in the motorcycle category on Craigslist, giving their own ads more prominence. I imagine that a lot of people who have their ads are removed never repost them because they become frustrated and give up.

I would not bother trying to sell anything on Craigslist now. Honestly, the idea of inviting a perfect stranger to your house to sell them something always creeped me out a little.  I would much rather put the word out on Facebook and Twitter than put an ad on Craigslist, only to get a bunch of calls from wierdos and then to have it taken down two or three days later. I have not decided if I will post a job opening on Craigslist again.

How could they fix it?

If I had the ear of Craigslist CEO, Jim Buckmaster for five minutes, I would tell him, “If you want to really serve the public, then you have to innovate, adapt and grow.” Peer reviewing is a great thing, but there should be accountability. The first thing that should be changed is that no one should be allowed to flag an ad unless they are a registered user. Also, when an ad is flagged, the member should be required to include a specific reason why it was flagged, and that reason should be shared with the ad creator if it is removed. The community should be able to vote on whether the flag was legitimate or not. An ad should only be removed after a certain number of members of the community vote, and the majority decides that the ad should be removed. Everyone should only be allowed one flag per ad and one vote per flag. I would also add a reputation system so that other users know if someone is a chronic flagger or if their posts are chronically flagged. This would lengthen the flagging and removal process for legitimate ads and reduce falsely flagged ads, but it will not significantly lengthen the process for spam ads. Also, this will help ad creators to make better ads because they will find out what they are doing wrong.

The one thing they cannot do is sit on their laurels and let the community police itself without giving them guidance and implimenting restrictions. A world where no one abuses each other and everyone lives in peace and happiness is called Utopia. The road Craigslist is on does not lead to Utopia; it leads to Irrelevant Land.