I’ve been selling a lot of stuff on craigslist.org recently, and while I absolutely love the site for the ability to turn my boxes of junk into quick cash, the more I use it the more I feel like it’s long overdue for an upgrade. In this interview a year ago, the eponymous Craig Newmark of Craigslist mentions that the site is written mostly in Perl. The function and design haven’t changed much in nearly 10 years. And while the rest of the internet has grown around new asynchronous technologies and social networking, a site that’s a perfect fit for both seems to have been left behind.

But that isn’t what baffles me. Craigslist on its own is doing just fine. They’re still the go-to site for online classifieds. What I can’t figure out is why, without any innovation or improvement in 10 years, that’s still the case. Where is the disruptive newcomer to unseat the mighty Craigslist? Doing a little searching for alternatives yields a lot of options without a lot of good results. The sites are either poor clones (Backpage), poorly designed and cluttered (vFlyer), or gimmicky and just poorly put together (RealPeopleRealStuff). Even the big players are starting to jump into this arena: Google offers Google Base and eBay has opened their international classifieds site Kijiji to the States, but both are still lacking killer features that might net them real market share.

Businessman and Dallas Mavericks owner Mark Cuban recently wrote in a blog post:

There will always be a company that replaces you. At some point your BlackSwan competitor will appear and they will kick your ass. Their product will be better or more interesting or just better marketed than yours, and it also will be free. They will be Facebook to your Myspace, or Myspace to your Friendster or Google to your Yahoo. You get the point. Someone out there with a better idea will raise a bunch of money, give it away for free, build scale and charge less to reach the audience. Or will be differentiated enough, and important enough to the audience to maybe even charge more. Who knows. But they will kick your ass and you will be in trouble.

So what’s it going to take to kick Craigslist’s ass? Here’s my list of features I’d like to see in a new classifieds site (or hell, I’d be just as happy if Craigslist would implement them). Give me these with a simple interface and good design and I’ll jump over in a heartbeat:

• Video and higher-quality pictures

  C’mon guys, this is the age of YouTube, of the Flip Mino and the iPhone 3GS. Why do people still go to garage sales? Because they want to SEE the things they’re buying, from all angles, they want to feel them and judge their size and look for imperfections. If I’m selling a DVD player, I don’t want to invite a stranger into my house just to show them it works. Pretty please let me upload video to my ads. RealPeopleRealStuff does this already, how hard can it be? And while you’re at it, 4 low-quality jpegs is not sufficient to display my wares. Storage is cheap. Amazon, Google, etc. are happy to provide server farms at your disposal. Let’s use em.

• Location awareness

  Newer browsers (Firefox 3.5, Google Chrome) are building location awareness right into your laptop. Web-enabled smartphones with GPS can pinpoint you in seconds and are already providing location-based services to help you find restaurants, gas stations, etc. But even web behemoth Ebay’s classified site Kijiji still relies on subdomain-specific listings like detroit.kijiji.com. How about giving me the option to set a radius from my location (5-500 miles) and show me all posts within that range?

• Real anonymity

  I want to sell something on Craigslist, but I don’t want to freely give out my phone number or email address. But oh, lucky me, Craigslist will post an anonymous email address on my listing and forward me the replies. How sweet of them. Except, now that I’ve got some replies in my inbox, my only option is to expose my real email or phone #. I’d prefer an account to log in to with an inbox, threaded replies, and the ability to respond to would-be buyers without giving out real contact information. Anyone can do this every day on Facebook, Twitter, MySpace, etc. Why not on Craigslist?

• Make it extensible

  If the new web services have taught us anything, it’s that providing an API and a way to expand your presence to other parts of the web is vital, nay, essential if you want to survive, and with good reason (which I won’t get into here). When I post a classified online, I want to be able to broadcast that information quickly and easily across my social networks. Give me widgets, give me RSS feeds, and even better give me a way to track this stuff. I want link tracking, visitor trending, I want to tie my posts into Google Analytics. Classifieds by nature get a spike of traffic when they’re listed which steadily falls off as they age. I want to see that traffic curve so I know if it’s time to relist my item, or if I just need to settle for a lower price because people are looking but not biting. And if nothing else, give me a simple way to put my listing on Craigslist as well (vFlyer already does this, to an extent (warning: this link goes to an INCREDIBLY boring video tutorial)). If you’re going to unseat the king, you’ve got to do it in his own castle.

This isn’t a question of if, but of when. It’s true that for any new classifieds site to get any market share, it will need to generate and eventually take traffic away from Craigslist, but if you give people compelling enough features with great function and design, it’s only a matter of time. A service with the attributes I described above is not out of reach for a new tech startup, and making it a viable business would be simple – I know I’d gladly pay a few bucks a month for a premium account that lets me post video, track link stats, etc. I personally can’t believe we’re approaching the second decade of this new millennium while Craigslist is still partying like it’s 1999. I want my Craigslist 2.0. So, who’s going to step up?