How Tech Became Cool Again

Dan: I think it’s funny that people complain there’s not enough money in New York for entrepreneurs to start businesses, and it’s so clearly, to me, the opposite. There’s too much money! Great ideas with great entrepreneurs will always creatively find money.


Who among the big media executives do you think understands technology and your world?

Ben: I’m scared of all those guys. I’m not saying anything

Dan: Tim Armstrong at AOL. He understands what it takes to build a big business, and he has a physical deck of cards that he has taken over.


You’re bullish on AOL?

Dan: I’m bullish on Tim Armstrong. He’s completely transforming the business.


Anyone else?

Ben: I think that everyone [in the big media companies] theoretically is headed in the right direction. I think everyone’s woken up and realized that it’s important, but I don’t think a ton of progress has been made anywhere that I can put my finger on. I mean, AOL is in a pretty good position because they don’t have any of these old media assets that they have to deal with. Everything they’re doing is already digital. I feel the same about IAC.


Who is hopelessly headed in the wrong direction? Do you see The New York Times turning itself around?

Dan: Gosh, I hope so. I really don’t have enough familiarity with what’s going on there, but it’s a really, really tough one to turn. But they’ve done a better job online than anyone.



Dan: They just have! Everybody reads The New York Times online.

Ben: But nobody pays for it

Dan: But they’ve made it something that everyone does. At least people are consuming the content online. Other companies can’t even get people to use the digital properties that they have.

Dan: The most ridiculous question in big media companies that people are trying to solve is how to get people to pay for content.

We did a story last week on how Newsday only got 35 subscribers after they put up a paywall.

Alexa: Are you serious? That’s terrible!

Ben: Did they tell people that? It’s not a great PR move.

The question is still, how do you get people to pay for content? A lot of the different models, one of which is for magazines, is that a bunch of magazines have tried to get together and start their own standard. It’s hard to imagine how the magazine industry is going to get together.

Dan: It’s hard to imagine Condé Nast or Time Warner solving the problem on their own. I helped launch Fandango, the movie ticketing site, and it was an interesting example of how the theater industry never could solve that problem on their own. We brought the industry together and proposed a solution where a tech company basically built a solution for them, went into partnership with them. That’s the model for the newspaper or magazine industry.


What do you think about the iPad?

Dan: I think it’s gonna be awesome! [laughing] I mean, you can see all the bad buzz, ‘Oh, my iPhone tortures me, drops my call,’ etc., etc., but then I buy [the iPad] the day it comes out and use it every day for the rest of my life.


What media do you consume? What do you look forward to reading?

Alexa: I almost exclusively do all my reading from links on Twitter


Do you read anything hard copy? Magazines? Newspapers?

Ben: People read The New Yorker. That’s the only thing I see people holding on airplanes.


Anything else? Help me out here.

Dan: The Economist


You read that hard copy?

Dan: I just grab 25 newspapers and 45 magazines at the beginning of the day


You get 45 magazines?

Dan: Yeah, I get 45 magazines, so I’m helping the industry. I don’t know if that will continue with the iPad.


What do you think of the Daily Beast and the Huffington Post? Is there any online media that you guys are excited about, that does it right?

Ben: I mean, I’m a realist. I love the Huffington Post; I have that political slant, so it’s for me. But I think what you find that is the people who are finding success are the ones who aren’t trying to go so mainstream. They have a specific angle or approach. Online, it costs so much less to be a publisher, so you can write about a very specific type of business and be profitable and build something there. Whereas in print, it’s a lot harder to do that.

Dan: I think in our kind of world, it’s all about voice. That’s the only way you can distinguish yourself. You guys are a good example.

Alexa: One of the great things now with distributing content is that you can really be more niche. So figuring out how to get people to care about the niche is what’s important. I would find in The Observer what I would not find in The Times or CNN. And I would like to read it. What matters to me is the city I live in.

Dan: I think if the content is unique, people will be glad to pay for it

Alexa: You were talking about brand issues. I believe in an aesthetically superior experience. I think you can expect in these few years to have technology move more towards you. Like the iPad, it will be really useful in making things look more interesting, in graphics, in not losing anything. So when that happens, you won’t have any problems just being text on a page. Consumers would love a glossy New Yorker or New York Times in a machine, so I wouldn’t fret about that. Just as long as it’s all centralized.

How Tech Became Cool Again