A CEO who got his job on Craigslist

Jim Buckmaster, the programmer-turned-CEO of online classified-ad site Craigslist answers your questions and a few of our own.

By Matthew Boyle, Fortune writer

(Fortune Magazine) -- With 450 sites in 50 countries, Craigslist is the undisputed leader in online classifieds, despite a stubbornly anticapitalist culture. Fortune's Matthew Boyle took your questions to Buckmaster, 44, to learn what's happening at the Web site that's rocked the ad world and transformed the way we clean our garage.

When and what was your first transaction on Craigslist? --Elma Kim, Los Angeles

Buckmaster posted his resume on the site eight years ago. Now he's CEO.
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Previous Q&As

A friend told me about Craigslist. In late 1999, I put my rsum up on it, and founder Craig Newmark saw it and invited me in for an interview. I was hired as lead programmer.

What advice would you give to a budding web entrepreneur? --Vish Ravishankhar, Chandler, Ariz.

Web ventures are best run by techies. Keep things simple. Be patient. Focus on user feedback. Don't take outside money if you can do without it.

How have you overcome any adversities that have been thrown at you during your career? --Jason Hopkins, Newark, Ohio

I kept quitting in the face of adversity until I found something I loved doing, after which point all obstacles became surmountable. I quit medical school and a few jobs. If you're in a job you don't like, almost anything can seem insurmountable. Conversely, if you are in a job you like, obstacles start to look small. At Craigslist it feels like we're doing something positive for society.

If you didn't work at Craigslist, what else would you be doing careerwise? --Joe Talarico, Lewiston, N.Y.

I would be building a platform for user-generated governance (UGG) as a replacement for our flailing "dot-gov" sector. It's utterly divorced from serving the public. Or maybe I'd take a year off and go backpacking.

At some point, doesn't Craigslist have to be more aggressive about scaling revenues? I understand you're small, nimble and profitable, but your business is pretty easily duplicated. Or do you think you can sustain your business based on user loyalty? --Aaron Letscher, New York City

Financial metrics aren't something we focus on; they're a pleasant side effect if we manage to do a good job by our users. We track page views to measure the usage of the site. We also look at the number of thank-you notes from users who have found their entire lives on our site - from spouse to house, job, furnishings, cat, dog, friends and a social life.

Do you plan to make Craigslist a public company? --Nixon Correia, Newton, Mass.

No. It seems like a lot more trouble than it's worth. We're having too much fun to exit, but we will go quietly when the nanobots are ready to assume control.

What is your attitude toward the seedier side of Craigslist - the often explicit personal ads seeking casual sex? Do you see this as an integral part of the business, or as an embarrassment? --Andrew Clark, New York City

Craigslist users are pretty sophisticated and don't tend to view sexual relations between consenting adults as seedy, at least compared to what goes on in the White House and Congress or the boardrooms of many large corporations.

Are there any plans to expand the real estate section of Craigslist and target the broker listings now on Multiple Listing Systems (MLS)? --Matthew Shields, Scottsdale

We don't go out of our way to target new businesses; our hands are full right now handling user requests. We'll add more cities soon, as there are lots of requests coming in. We are also working on creating local language pages. And although our hope is to always remain a small company, we are actively looking for more good techies.

How do you generate excitement and awareness about Craigslist in a city like Stockholm, where most people don't know about it? --Jacqueline Fabius, Stockholm

We've relied exclusively on word of mouth. I hear, though, that Stockholm is very nice; perhaps I should go and drum up interest personally.

What part of Craigslist gets the highest traffic? Does it change depending on the city? --Yury Pishchik, Boston

Our "for sale" section has the highest traffic, followed by housing, jobs and personals. Our busiest cities are San Francisco, New York, L.A. and Seattle. Our New Orleans site took off after Katrina. Usage went up by 10,000 percent overnight. Initially the site was used to find missing persons. Then ride sharing. And later thousands of offers of employment came in from all over the U.S. to help the victims.

Where do you see Craigslist in five or ten years? --Nishi Viswanathan, Austin

I would expect lots more of the same, plus incremental improvements based on user requests. In ten years we may be approaching the Singularity [a state when machines become smarter than humans], in which case all bets are off.

Fortune's Matthew Boyle Asks

After focusing its online classified efforts outside the U.S. for the past few years, eBay just launched a U.S. version of its Kijiji service, which is very much like Craigslist. How will you handle this new competition?

We operate with a public-service mentality such that we don't think in terms of competition. That really saves me a lot of grief. During the dot-com boom, we were derided for our noncompetitive approach, but of the hundreds of Web companies founded between 1995 and 2000, we're one of only a handful that survived and prospered.

Doesn't eBay's 25 percent equity stake in Craigslist pose a potential conflict?

Those issues are obviously a concern, but our first instinct is to trust eBay (Charts, Fortune 500) to take the high road.

What are the most bizarre objects or services sold on the site?

That depends on what you find bizarre, but husband-for-hire - the person meant everything but the sex - pet astrology and spare parts for a time machine struck me as odd. There are lots of funny ones in our best-of section on the Web site.

What other Silicon Valley startups interest you, and why?

Tesla Motors. Electric cars seem like a great way to address our energy woes, since we have so much excess overnight generating capacity.

Have you bought or sold anything on Craigslist lately?

I recently bought a BlackBerry 7280, which is a discontinued model that has the lowest SAR [specific absorption rate, the rate at which radio-frequency energy is absorbed by the body] of any cell phone.

What interests or hobbies do you have outside work?

Each year [my companion] Susan and I spend a week out of cell phone coverage with friends and an ostrich named Huey on an organic farm called Emandal on the Eel River in Mendocino County.

On deck: Shelly Lazarus, CEO of ad giant Ogilvy & Mather, answers your questions.  Top of page