In the early 1990s, Jonathan Glick, a programmer and news enthusiast, approached The New York Times about taking the paper digital. That path took him to AOL, iVillage, and finally—when the paper was ready to have an independent Web presence—The New York Times Online.

At a time when the term “news business” seems increasingly like an oxymoron, Jonathan Glick shared with CJR’s Diana Dellamere his straightforward business perspective on about what works, what doesn’t, and what we just don’t yet know about doing business and news on the Web.

Diana Dellamere: Coming from a software/technical background, how did you get involved in the news business?

Jonathan Glick: The Web had just happened, and I was thinking, “Where does this matter?” The answer was “I’m not sure, but probably with people who have content.” The New York Times wasn’t yet on the Web but they were on AOL and I wrote to them and said “I’m just a programmer but I would love to help you guys with this any way I can.”

DD: Do you still think that the Web and newspapers are a natural fit?

JG: I think nothing about the Web is that good for traditional news businesses. Because the Web creates so much competition for them and they are so slow to react to that.

DD: What are newspapers doing wrong on the Web? And what did they do wrong in the past?

JG: For the most part, what drives what people read are their strong interests. So, if I love the Vancouver Canucks, I want to read stories about the Vancouver Canucks every day. So, unless The New York Times finds a way to cover the Canucks, or whatever my interests are, I’m just not going to go there all the time. And what news businesses would have had to do to be competitive would be to occupy more space in the total interest lists of more readers. And they didn’t, because they felt, (a) that wasn’t relevant to the news and, (b) they couldn’t figure out a corporate model that would enable them to write about those things without sacrificing what they saw as quality.

DD: So, is all lost? Or is there a way to be successful on the Web today?

JG: To be successful on the Web today, you need to create millions and millions of pages. You need to be relevant to everybody’s shared interests. The truth is that we share some things, like you and I may be both interested in what’s going on in Washington today, but chances are your next twenty interests and my next twenty interests don’t overlap that much. So, to be a major player on the Web—where people control what they read rather than the publisher controlling what they read—you need to satisfy that next twenty interests for everybody.

Doing that means a completely different sense of what quality means. Because, if you only publish things of very high quality, you are obviously not going to be able to develop an organizational model to do that; you are just not going to be able to hire enough people. So you need some type of model that results in a lot more content. Google has a model: they mine the Web and create links. has a model: they’ve created a network of guides. Huffington Post has a model: they’ve got a small number of professional writers sitting on top of a huge number of amateur enthusiasts. The Daily Kos has a model: they have a volunteer activist organization that creates diaries.

There are all sorts of models. But what’s clear is that the traditional sort of model that the newspaper and magazine world has—where a small number of people producing a small number of articles—has a smaller and smaller footprint every day on the Web.

There seem to be two models for commercial success on the Web right now. One is creating vertical content—a lot of it—in subjects where people are looking to buy stuff. And then being essentially a way that advertisers can buy leads. So, you build a vertical parenting site where you can search for baby strollers, for example. And then you take that interest, that intent, and you sell it to merchants looking for people to buy baby strollers. That seems to be a decent model that’s likely to work long term. People always want advice on what to buy.

Even in that world, you need lots and lots and lots of content—how-to content, a little bit of news—and it’s very unlikely that a model of hiring a staff can produce enough original content.

Diana Dellamere is a former CJR staff writer.