By Matt Wells
In New York
For a man with no plan, who describes himself as just another "line worker", Craig Newmark is doing alright.
Meeting the international media in Manhattan this week, the 53-year-old stood in his uniform of black jeans and grey shirt, trying to convince sceptical reporters that his eponymous Craigslist is not out to destroy the newspaper business.
The geeky former systems engineer for IBM has come a long way in the last 11 years.
Craig Newmark refuses to be pigeon-holed
The electronic mailing list he began for like-minded friends in the San Francisco Bay area now has "well over three billion page views" per month he says, which makes it the seventh biggest presence on the internet.
He may be breathing down the necks of Google and eBay, and he believes they share the same "moral compass", but like something from the plot of Revenge of the Nerds, his almost anti-profit business employs just 19 people, and is still based in a San Francisco living room.
Everything about Craig and the company he incorporated, almost reluctantly in 1999, makes no sense in business terms. But that is its genius, and the reason why its users love it, and swear by it.
His mantras, which he articulated again from the podium of the New York Foreign Press Center, are that it is a real and reciprocal online community that is "just trying to give people a break" across the 190 cities it serves.
He admits that they are going to have to hire some more people if they are going to expand on the current simple formula of exclusively English language-based zero-graphics design.
The site's only income derives from job listings in three US cities, though discussion is under way for charging a fee for accommodation postings - mainly thanks to huge traffic on the New York property pages.
Everywhere else in the world it is free to every user, and although Craigslist still nets around $20m a year, it could be generating much more profit.
Ever since the first offer came along from Microsoft in 1997, Craig has been saying no to advertisers and buyout deals, and now "they've stopped bothering us" he said.
However, eBay did manage to buy 25% of the company in 2004, when a former employee unilaterally decided to sell his shares. Craig says the unexpected relationship has been beneficial so far.
"It may occur to you that we don't have much of a business plan, and you'd be right," he said. Few company founders could get away with that kind of pronouncement, but Craig Newmark is arguably unique.
"One of the reasons I'm not in management is because I am really really bad at hiring," he said. He introduced himself to the assembled reporters - from countries as diverse as Estonia, China, Mexico and Canada - as simply part of the five-person customer service team.
There is one clear advantage to the self-deprecation however. When it comes to questions of his own pay and hard company figures, he can be convincingly vague: "We know we're doing okay. That we continue to do okay, that works for me."
If he looks and sounds like the antithesis of every business school model, it is clear that Craig's honesty and acumen when it comes to giving people what they want is highly effective.
Craigslist nets around $20m a year
Many in the media are beginning to dub him the assassin of classified advertising - the life-blood of the newspaper business. He rejects that charge, arguing that the internet itself is the real culprit. Newsprint is simply passe.
When he reached the podium, he gleefully compared his position to that of the fictitious president's press secretary in the US political drama, The West Wing.
As his current hero seems to be the cable TV satirist Jon Stewart, it is tempting to portray Craig Newmark as a liberal subversive - or an idealistic, digital age social worker - who is using his business to undermine conventional politics and morality.
But he refuses to be pigeon-holed: "We try to be driven by the values of the people who use us," he said.
"People have made assumptions about... my politics personally, and actually no-one knows what my politics happen to be... I haven't even articulated my politics to myself."
One label that does stick, is that Craig is an indefatigable optimist. He is convinced that however large the list of cities gets, it will always be fed by a common desire for urban dwellers to help each other.
He spends much of his time these days weeding out the minority of "bad guys" who lie and scam their way through Craigslist, but the whole ethos is about self-policing and communal values.
With a portion of each site given over to dating, "erotic services" and "casual encounters", it is not hard to see for example, why only Istanbul has joined the Craigslist ranks from the Islamic world.
"The theoretical part of me thinks that the bigger we get, the less human connection people have," said Craig. "It doesn't work that way."
"People are still getting that sense of personal connection. Somehow we're maintaining that, by just trying really hard every day to do the right thing. It's a mystery."