Info/Law

I have been obsessing a little over the recent sale of the New York Observer to Jared Kushner, the 25-year-old real estate scion who is also a rising 3L at my alma mater, NYU Law.

There are a couple of personal reasons for my obsession (beyond the predictable envy of a 25-year-old law student buying a newspaper and the angle the MSM is emphasizing, that Kushner’s mogul father is a convicted felon who was often the target of Observer exposes). For one, I have subscribed to and enjoyed the Observer for more than a decade, during most of which I was a displaced and sometimes homesick New Yorker. More important, [disclosure here] my brother Tom is the paper’s managing editor.

The Observer is a unique weekly newspaper, with a mission of muckraking and sometimes snarky coverage of New York’s power elite — politics, media, high-flying nightlife, and of course real estate. The wider public likely knows it for just two reasons: (1) its peculiar salmon-pink color and retro font and layout and (2) its role as the birthplace of Sex and the City (long before Sarah Jessica Parker ever met Carrie Bradshaw, the series actually had its genesis as a weekly Observer column, complete with Mr. Big).

In media circles the Observer is much better known. Its scoops are constantly highlighted in Gawker, for example. The paper is well-regarded for its aggressive coverage of city politics and its intense scrutiny of both the content and the backroom office politics at the New York Times — as Observer editor Peter Kaplan (Tom’s boss) recently told New York Magazine, “[S]o much of why the Observer is here is to tell New Yorkers that the benign dominance of the Times is a sort of tyranny. It’s as important to us as covering the State Department is to them.”

What does any of this have to do with Info/Law? I’m getting there. One of Tom’s tasks — and now Mr. Kushner’s too — is figuring out the online future of a scrappy and admired niche publication like the Observer. In a Long Tail world this should be easy, right? And the Observer seems so well-suited to it. At least that’s what lots of people are saying. As that same New York piece noted:

[P]aradoxically, the paper’s smart-alecky tone and approach are, if you will, a throwback to the future: Typographically, the paper may recall what Pulitzer did in the twenties, but in its opinionated reporting and nonstop attitudinizing the Observer is also modern and bloggy, like the Huffington Post or Slate.

Likewise, Jack Shafer has the following unsolicited advice for Kushner in Slate today:

About the Web: If you were starting the Observer today, you’d start it on the Web, not in print. But you’re not starting the Observer today, so don’t feel compelled to ax the print edition right this minute for migration to the Internet. I believe that newspapers are dying a slow and profitable death and most will eventually segue to the Web. [snip] As a newspaper publisher, you’re in the manufacturing and distribution business, but as a Manhattan newspaper publisher you’re the beneficiary of compact and reachable readership. Milk the print product for all you can, and create a Web adjunct to drive traffic back to it.

Easy, right? The problem, of course, is that the Observer is doing just about this already, and reportedly losing two million dollars a year. The paper’s web site now allows free access to its blogs and current content, but charges for archives access and uses the site to promote print subscriptions. Just what Shafer suggests. This is quite a common model but, as more readers get comfortable substituting screen for printed page, giving the newspaper away becomes a less sustainable business model. Indeed, Shafer’s own Slate is a great but money-losing all-free all-web publication.

There are other options. The Wall Street Journal site famously puts nearly everything behind a paywall (except for its “Free Today” page). Salon makes you sit through an ad before you can read. The New York Times created “Times Select” which puts columnists and certain other supposedly premium content behind a paywall. And of course many bloggers born on the web have no print adjunct, but they are still brainstorming how to make money too.

Like many things on the internet, online newspapers are an ongoing experiment conducted in many thousands of labs all over the world. Lots of exciting stuff is happening, particularly where profit is not a (major) goal. But Jared Kushner, and Tom, and everyone who cares about information has a big task in front of them (us) figuring this out. Eventually it will all work out. If it were easy, though, there would be a lot more blog millionaires out there.

Filed under: Digital Media, Internet & Society, Media