Esther Dyson, Chairman, EDventure Holdings

Few are the IT veterans who don't know Esther Dyson. For nearly 30 years, the daughter of famed physicist Freeman J. Dyson has written about, spoken on, and invested in information technology and the Internet.

Born in 1951, Dyson worked for a variety of companies, including Forbes, after graduating with an economics degree from Harvard. In 1983 she started her own investment firm, EDventure Holdings, based in New York City. For the next 20 years, she worked as a journalist and commentator on technology, frequently analyzing ways to organize and deal with information in her newsletter, Release 1.0.

When the Internet Corporation for Assigned Names and Numbers -- ICANN -- formed in 1998, Dyson became its founding chairman, a post she held for two years.

In 2004, she sold EDventure Holdings to CNET, retaining the company name. Through the present iteration of the firm, Dyson invests in and helps to manage a variety of startups and projects in the fields of IT and the Internet; personal space travel; healthcare and IT; emerging international markets; and nonprofit groups. Past investments include Flickr and del.icio.us, Meetup, Boxbe, and Voxiva, among many others. She is also a director of 23andMe, an online source of personal genetic information.

Internet Evolution caught up with Dyson recently in the New York offices of Meetup, where she appears to set up shop occasionally in a cubicle near the window. Settled in a tiny but comfortable conference room nearby, we got down to brass tacks. Here's an edited version of that conversation.

Internet Evolution: You’ve had a front-row seat for the commercialization, regulation, and funding of the Internet. What’s been the biggest surprise for you about how the Internet has evolved? And what’s been your biggest disappointment?

Esther Dyson: Well, surprise and disappointment are the same… There are two big things: First, I was a much bigger fan of anonymity then than I am now. I thought it was cool. And it is, but it turns out anonymity really encourages bad behavior. I’m not in favor of the government tracking everybody and so forth, [but] at least persistent pseudonyms and communities and stuff like that makes everything a nicer place.

It’s like a lot of things. I’m pro choice, but I think abortion is an unfortunate thing. I think the same thing about anonymity: Everybody should have the right to it, but it’s not something one wants to encourage. And that’s not weasel words, that’s the reality of it.

[Anonymity] should be allowed. People should be able to make that choice, and there are many reasons to make that choice. If you live in an oppressive regime, you may well want people to be able to remain anonymous or have secret communications. But at the same time, it should not be encouraged, and it should be acknowledged that it’s a response to a bad situation.

IE: What do you think about the president-elect appointing a CTO, as he’s said he plans to do? Whom would you like to see in that position?

Dyson: First of all, I think what we really need is more a CIO than a CTO. Broadband is not a technology issue, it’s really a financial issue. How should it be funded? Should it be subsidized? I tend to think not. Broadband is a miraculous technology, and it ought to be able to pay its own way. We need competition; we also need attractive enough propositions [in which] companies will invest.

Every time you create, for example, an HR department or a CIO, you’re sort of saying the other people don’t need to worry about it, and in a sense, you need to be careful that you don’t start segregating what are some important economic and governance issues and just say, "Oh well, that’s the CIO’s problem -- we don’t need to deal with that here in our agency or in government."

The truth is, I’d like a clearer definition of what the job is supposed to do, honestly. Is it supposed to be an administrative job, a policy-setting job, kind of a strategist for how information is used, or a strategy for how government becomes more transparent and accountable? I’m not sure. All those things are desirable.

So that said, I’d love to see Larry Lessig in the job.

IE: More than 10 years ago, you discussed a model whereby people would pay for content…

Dyson: No, I didn’t say that. I said they would pay for services.

IE: OK, well, more recently, you said there was going to be a new model other than the old ad-per-eyeball approach, so that people would actually make their private information available and then be approached by different vendors with offers of what to buy instead of ads popping up. Are we getting any closer to that?

Dyson: Sure, that’s the basic notion behind, for example, Facebook or the Dopplr travel site, which I’m an investor in.

IE: You don’t see a resistance to it? Do you see a dwindling of the old ad model?

Dyson: Not yet, I think ultimately it will, because people will tune out. Some people don’t like it and some people do; I think that it’s up to the vendors to figure out who those people are and to deal with them appropriately. I mean, if you can categorize me by whether I’m my age, you also ought to be able to categorize me by whether I want [unsolicited] offers or not.

Next Page: Premium Content & Social Sites