STANDING at the crowded bar in New York’s Soho House, Johnny Boston looks very uncomfortable. The 5ft 9in president of New York film production company Raw Films Inc has his head tipped back at an angle more usually associated with the victims of car accidents as he chats with 6ft 7in Jim Buckmaster.

Buckmaster, chief executive of Craigslist, is in New York for a question and answer session to a select audience of the new wave of digital entrepreneurs and media types. “I wish I was that tall,” says Boston. “Be careful what you wish for,” says Buckmaster. It is his theme for the evening.

Buckmaster was invited to talk by the Glasshouse, a talking shop for the digerati started in London during the last dotcom boom back in 1998.

Eight years on, most of the first wave of web businesses have gone to the wall. But not Craigslist, the world’s most used classified ad service. The site started in 1995 and now attracts more than 7 million new ads each month, operating in 190 cities and 35 countries. It’s the seventh most visited website on the planet and attracts 3 billion page views per month. The majority of the ads are free — the company makes its money charging for job postings in big cities such as San Francisco and New York. Its been profitable since 1998 and employs just 19 people.

The crowd know all this. What they want to know more about is money. Unlike nearly all of its successful contemporaries, craigslist has eschewed cashing in with an IPO or sale despite a flood of offers. “So why haven’t you sold out?” asks the Glasshouse’s Judith Clegg.

“We do hear that a lot,” says Buckmaster. “We make a good living and we are not interested in selling. (Gasps from the crowd). You should be careful what you wish for. Do you really want to have to walk around with bodyguards?” There are cries of “Yes, yes” and “I do” from the back.

Ebay founder Pierre Omidyar sits on Craigslist’s board. According to Forbes, Omidyar is the 35th richest man in the world with a fortune of $9.9 billion.

“The problem with insane wealth is that not all of it is good,” says Buckmaster. Someone in the audience laughs insanely.

Buckmaster argues that the secret of the site’s success has been that it has not had to chase for extra dollars. Craigslist has no banner ads, no pop-ups: “Customers never ask for them,” he drawls.

The website doesn’t even have to think about what the competition is doing: “We just work on our project list. We don’t have the staff even if we wanted to mount some great response.”

And what about the future, asks one guest. “Aaah. I don’t really have a grand vision,” says Buckmaster.

Sitting at the front of the room, Buckmaster seems almost normal height. Most of his length appears to be leg. He has that casual, laid-back West Coast vibe off pat. Buckmaster’s voice is low and slow and he has the quiet confidence of someone who knows he has little to prove. His microphone keeps cutting out. He doesn’t seem too fussed. He likes New York, likes seeing celebrities on the street. Samuel L Jackson was in his hotel. He’s a rock star, but not the front man.

Think Dave Grohl in Nirvana.

But for this crowd, all natural-born sellouts, Buckmaster’s tune is a little hard to hear.

“What would you do if Arthur Sulzberger (New York Times publisher) offered you $1 billion for Craigslist? Tomorrow!” asks someone who sounds like she’s describing a daydream she has had many times.

“Well it hasn’t happened as often recently,” says Buckmaster. “But we’re not interested.”

“Jesus,” sighs a woman at the back.