Handing Craig Newmark my money, happily

I just bought a paid ad on Craigslist for the first time — a job posting for my startup, which is looking for a VP of engineering.

This was a curious little milestone/experience for me as an Internet user and someone interested in digital business models for news. Of course, Craigslist has famously all but choked off old-school classified advertising in print, since people use the site as a substitute to newspapers. But what struck me going through the site’s ad-buying experience firsthand is how completely dissimilar it also is to anything that a legacy news organization now offers within its online product mix.

I don’t claim to be the first person to notice this. For example, E&P’s Alan Mutter has covered it in several recent blog posts, including this one from April that nicely points out the pitfalls of most news providers’ “run-of-site” ad strategy online.

That said… Damn. To see the difference in action is something else altogether.

To be specific, my ad buy on Craigslist was:

• Simple. The whole process was based on some straightforward Web forms and email, with no password or sign-in or paywall hassle at any point. You create the ad first, the Craigslist system generates a unique non-public link for verification, then it emails the link to you, then you just click through. On that page, you enter your payment info.
• Reasonably priced. It was $25 to post my ad on the New York Craiglist site, with no limit on length.
• Well-targeted. Aside from the fact that Craigslist has a subdomain dedicated to New York City, it also lets me target my ad by neighborhood. Good luck finding that feature on a newspaper website.
• Fully interactive, Craigslist generates a unique anonymized email address for people to respond to my ad directly, and I can edit my ad even after it’s been posted.

It’s also worth noting, my purchase was a logical extension of my free usage of Craigslist over the years. I bought something precisely because they let me kick the tires for free looking for other stuff previously. As a free customer, they clearly never viewed me as a “parasite,” or any of the other absurd terms that newspaper publishers have sometimes been known to use referring to their own online community members.

By the way, that free usage included an ad we did a few months back for a short-term “gig offered” looking for a contract developer for the startup. Even though that one was technically a business-to-business transaction as well, Craigslist didn’t overplay their hand, realizing that the bar would probably be higher to charge real money.

We got several dozen responses to that earlier ad, many of them viable options, so I was definitely willing to upgrade for the VP ad when the time came.