Thinking Out Loud: Rupert Murdoch and Chris DeWolfe

Continuing my series on folks I’ll be interviewing at Web 2 this year, next up is Rupert Murdoch and Chris DeWolfe, who will be our dinner guests on the first night. As previously noted (thanks for all your input), we start the day with Mark Zuckerberg, and it has a certain balance to end day one with Murdoch and DeWolfe, whose MySpace ruled the social networking roost uncontested until Facebook’s rapid acension. Regardless, the purchase of MySpace still ranks as one of the smartest moves ever made by an “old media” company.

Now, MySpace is still much bigger than Facebook, but as many are quick to point out, Facebook is growing much faster (more here). Clearly one topic of conversation will be how MySpace will respond to its new competitor – will it open up to the extent Facebook has, for example? It’s already well down the path of making money – in fact, it recently introduced a new self service ad platform based on six months of research into leveraging personal profile information.

This brings MySpace squarely into the same privacy conversation as Google, Facebook, Yahoo, AOL, and the rest of the ad-driven world. So we’ll clearly address that issue, and tons of other MySpace related questions – the future of the service, thoughts on being part of the Newscorp empire, those interesting contract conversations, its relationship with Google.

But with Murdoch in the room, there is a lot more to discuss.

As Time put it, Murdoch is one of the last true individual media tycoons, running an empire that stretches around the world with nearly every flavor of packaged goods media you might imagine, not to mention FIM, the arm that owns MySpace and various other interactive businesses like IGN and Scout. He’s also very controversial, eliciting alarmist articles like this one at a rate of at least one or two a day. In fact, if we were to compare Murdoch to anyone, it might be Bill Gates at the height of his power in the mid 1990s. At least, that’s a fair comparison in terms of Murdoch’s reputation in the mainstream media world – it compares to Gates’ reputation in the mainstream IT world ten years ago. I wonder how he feels about that? And how does Chris feel about working for him?

Then there’s the impending launch of the Fox Business News Channel. The battle for Dow Jones, the case for making its properties free, among other issues. Murdoch and DeWolfe’s view on the China problem/opportunity. The question of who might run the company when he is gone, and what he wants his legacy to be.

Murdoch is not without a sense of humor and a clear sense of what many think of him. Great quotes from the Time article: “When you’re a catalyst for change, you make enemies — and I’m proud of the ones I’ve got.” And this one, on changes he might make at the WSJ: “When the Journal gets its Page 3 girls,” (Murdoch) jokes late one night, “we’ll make sure they have M.B.A.s.”

I’d love to play the word association game with both of them – asking for a one word or one phrase response to a number of topics and/or companies – Google, Facebook, net neutrality, Microsoft, Comcast…

In fact, the more I think about this interview, the more I realize I need your help. We’ll have plenty of time to talk – dinner interviews are longer than the mainstage plenaries, but there are so many possible angles to take, your input will help me focus.

So what do you guys want to hear about from DeWolfe and Murdoch?