Chapter 21
JIM BUCKMASTER
CEO of Craigslist
Architect of Craigslist home page design
Dropped out of the University of Michigan Medical School
 
 
 
 
 
Jim Buckmaster responded to an ad on Craigslist looking for a programmer. The job was at Craigslist itself. Not only did he get the job, but 11 months later he was running Craigslist. That just might be the Internet equivalent of working your way up the corporate ladder by starting in the mailroom.
Of course, to call Craigslist “corporate” would be a stretch. Sure, the web site gets an estimated 50 million unique visits a month in the United States alone, and an estimated 20 billion page views worldwide, ranking it in the top 10 in the United States and top 22 globally [wiki per Compete.com on April 7, 2009]. But it is run by a mere couple dozen or so employees who cling to their goal of serving their clients’ needs, not Wall Street’s or Silicon Valley’s expectations. Buckmaster says:
A lot of people over the years see our approach as being weird or unorthodox, but that doesn’t mean that we’ve felt the pressure to conform to the way everyone else approaches running an Internet enterprise.
What is weird or unorthodox? Certainly not the concept. Described simply, Craigslist is a web site where classified ads are posted. But it is more than that. It’s an online community with an attitude. The site touts its “relatively non-commercial nature, public service mission, and non-corporate culture.”
Visiting the Craigslist site at www.craigslist.org is like taking a trip back to the early days of Internet site development. If anything in the Internet world could be called old-school, this is it. The simple design, the absence of banner ads and other eye-catching images reminds you of a day in the mid-1990s when hooking up to the Internet involved a telephone modem and a fuzzy sound followed by a beep to indicate you’re online and ready to go.
None of that is by coincidence. Buckmaster has had a hand in keeping the approach straightforward. Classified ads are simple, and that’s what Craigslist tries to be. It lists more classified ads than any other medium in the world, an estimated 40 million new ones each month. It also lists more than a million job ads each month, making it a player in that arena as well. But you shouldn’t be fooled by the simplicity of the site into thinking that this isn’t a major business. It is, and newspapers across the country can tell you that Internet sites like Craigslist have played a significant role in the newspapers’ collective financial demise.
By now a lot of people know the story. The site was launched in 1995 by its founder, Craig Newmark, who wanted to send his friends a list of events in the San Francisco area. The early postings—“Craigslist”—sent to e-mail addresses included many social events of interest to software and Internee developers. The number of postings and subscribers grew quickly, and the users found the new “Craigslist” a great way to communicate with a lot of people in an inexpensive way.
Postings began to include jobs, and later, housing, items for sale, services, discussion forums, and eventually a personals section. (Craigslist received some criticism for allowing “erotic services” listings, but in 2009 replaced them with an “adult services” section, which requires a fee and is policed by employees to prevent ads for prostitution.)
It creates revenue (as of January 2010) by charging for job ads in select cities: San Francisco, New York, Los Angeles, San Diego, Boston, Chicago, Washington, D.C., and Portland, Oregon. One of the benefits of charging for job ads is the upgrading of their quality, with the virtual elimination of get-rich-quick ads.
The multicity architecture now includes more than 500 cities worldwide. It was implemented by Buckmaster when he came to the company, situated in Newmark’s San Francisco apartment, in January 2000. As lead programmer, he designed the home page and helped round out the online community with a search engine, discussion forums, a self-posting process, and a flagging system. In November of the same year, he became Craigslist’s CEO.
Despite the enormous success of the Craigslist brand, Buckmaster and Newmark have resisted outside pressure to monetize the company’s value by doing things like charging for all of its ads—most are still free—and going public in order to bring in millions of dollars to help fund the company’s expansion and create an enormous payoff for its owners. But Buckmaster and Newmark, as the primary owners (eBay owns roughly 25 percent, bought from a former employee), have shown no inclination to turn the perceived Craigslist value into gigantic bank accounts.
Yet Buckmaster’s own bio on Craigslist proudly touts arrows that have come his way: “Possibly the only CEO ever described as anti-establishment, a communist, and a socialistic anarchist....” The latter charge was lodged by Martin Sorrell—that’s Sir Martin Sorrell—the chief executive at WPP Group, one of the largest advertising companies in the world.
The Craigslist web site links to Sorrell’s 2006 quote (FinancialTimes.com, June 20, 200G):
“How do you deal with socialistic anarchists?” he [Sorrell] asked, referring to Craigslist, the popular, free classified advertising site that has been threatening revenues at U.S. city newspapers.
“The Internet is the most socialistic force you’ve ever seen,” he added, noting that the response from some media groups had been to offer their content for free in traditional and digital form.
“They have decided—‘if I don’t eat my children, somebody else will,’” he told executives from UK regional newspapers attending an industry conference, adding that he disapproved of giving away content for free. “You should charge for it if the consumer values the content,” he said.
But change in the newspaper business model was inevitable when the dot-com era arrived. The traditional model included selling classified ads and display ads, and charging subscribers for purchasing the publication. The reason that a reader could buy a paper for just a quarter at the vending machine was that the primary profit generator was the ads. But the Internet has destroyed that profit-making model.
As Buckmaster says, “There’s been a sea change in underlying technologies and a lot of newspapers have had trouble adapting to that sea change.”
Warren Buffett may have put it best in an interview on CNBC on May 4, 2009. He argued that if the Internet had existed before newspapers, newspapers would never have made it. “[If] I came along one day and said I have got this wonderful idea: We are going to chop down some trees up in Canada and ship them to a paper mill, which will cost us a fortune to run through and deliver newsprint, and then we’ll ship that down to some newspaper, and we’ll have a whole bunch of people staying up all night writing up things, and then we’ll send a bunch of kids out the next day all over town delivering this thing, and we are going to really wipe out the Internet with this, it ain’t going to happen.”
And certainly the multitude of outlets for keeping up on the news hasn’t helped newspapers. People just don’t read them like they used to. And that demand for news is what gave newspapers their raison d’etre. With the decline of that demand, as Buffett says, “The old virtuous circle, where big readership draws a lot of ads, which in turn draw more readers, has broken down.”
Buckmaster touts Craigslist’s strength over newspapers. “The online medium has stupendous advantages compared to print for classifieds,” he says. “We’ve tried to take advantage of those to provide something that users would really love, and users are certainly enjoying the online classified medium.”
But that’s not to say that Craigslist is a nonprofit organization, which some loyalists may believe. Buckmaster set the record straight in an interview with Telegraph.co.uk in London. “We are not so much anti-capitalist.... We’re fortunate enough to have built a very healthy business, even though we haven’t attempted to. All we have done is stop short of trying to become insanely wealthy. We have met billionaires, and it sounds funny but it’s not necessarily a bed of roses to have that kind of money.
“People with that kind of wealth have to walk around with bodyguards. Their friends and extended families look at them in a way they wouldn’t necessarily choose. Their life becomes about figuring out how to employ all that money either by philanthropy or other means. So we don’t consider it that revolutionary to have stopped short of that.”

Jim Buckmaster’s Best Mistake, in His Own Words

My best mistake was choosing to drop out of medical school about halfway through. This was at the University of Michigan Medical School. I got about halfway through and I had the feeling that this wasn’t for me.
This, despite the fact that I had so much invested in the process, both financially and in time and energy. And it certainly felt like a mistake at the time, and I had a lot of people telling me it was a mistake. And I felt like it was a mistake for years and years afterward. But ultimately I thank my lucky stars I made that mistake.
And my grades were good. I had mostly As. I was near the top of the class. Number one, I just did not enjoy the process. Increasingly I found that I wasn’t enjoying the study of medicine. I found it kind of dull and boring. And the practical experiences I was having—I just had a hunch this isn’t what I wanted to do with my life.
And it’s such an all-consuming profession, and I felt that with these kinds of persistent doubts I needed step away from it, at least temporarily. So the shape of my initial decision was to take a year off.
And then I took another year off, and another year off.... And I just ended up never going back.
 
Q. How long had you been in med school?
I had completed almost two years [of four] and I had racked up large student loans.
I didn’t really see a way I was going to pay those loans off in a timely fashion. That’s at least partly why it seemed like a mistake at the time. I didn’t really have a plan B.
If you continue, the loans are not a problem, because certainly that’s one of the better-paying professions. And at that point I had no inkling that there was something waiting for me that would eventually pass what was possible in the medical profession.
 
Q. Was there a moment when it struck you that you couldn’t do med school anymore?
I found the study of pharmacology stupefyingly boring. Most people liken it to attempting to memorize the phone book, just memorizing a huge number of disjointed facts.
 
Q. How soon did you know you did the right thing?
I can remember almost 10 years after I dropped out thinking, “I can’t think of a route to getting to a job that pays even $50,000 a year.” I was still in debt, and had no real career prospects at that point.
Kind of out of boredom I started learning as much as I could about the Unix operating system, and then shell programming, just because the work I was doing on data entry and data processing was quite dull.
 
Q. At what point did you finally believe you made the right decision?
As soon as I got into Web programming. I was hooked from the beginning.
I would sometimes sit in my chair working 18 hours at a time—and a short amount of sleep and that was my day. I found it so interesting, and I thought, “Oh my gosh!” Here was something coming out of the blue that was very interesting and fun to do. The higher-ups were very encouraging, so it wasn’t long before I knew I was onto something.
When the Internet and the Web rolled around, I was in the right place at the right time.
I ended up on the front end of a terabyte-scale data archive at the University of Michigan. It was a primary data archive for the political and social scientists that all major universities subscribed to. Up to that point they had been distributing data on nine-track tapes in the mail.
Researchers were able to access and download data sets through this Web interface, and ultimately doing this analysis online. In retrospect, there weren’t too many other places with the kind of level of opportunity for Web programming that existed there at the archive circa 1994-1995.
So the timing was right. There was certainly an element of good fortune there, as I think invariably there is.
I just loved Web programming from the get-go. It was strictly a self-taught thing. But the wonderful thing about Web programming is each web page you can see the source programming for it. You can teach yourself. In fact, many of our programmers at Craigslist are self-taught.
 
Q. What was guiding you?
At a gut level I wanted to do this. Yes, I have a tremendous amount of debt that I don’t know how I’m going to pay off. Yes, there was a lot of self-doubt there. Yes, I left one of the better-paying professions that a lot of people aspire to. But according to my experience and how I’m doing, med school doesn’t seem like it’s right for me.
Despite the fact that I don’t have a plan B, and I don’t know how I’m going to pay off this debt, and everyone around me is telling me this is a mistake, the inner voice, or gut feeling—that definitely was in play there.
 
Q. What lesson would you pass along to someone else?
One, trust your gut instinct.
When it comes to doing something as important as what you’re going to spend the rest of your life doing, you need to respect your gut instinct.
Another one is that it doesn’t matter what you’ve invested in something. What you’ve invested in the past is to some degree immaterial. What you’re looking at is the future and where you want to place your investments in the future.
These lessons were learned the hard way, but the story had a happy ending. Success was assured before I ended up at this particular company. Success was finding something that I loved to do.

About Jim Buckmaster

Possibly the only CEO ever described as anti-establishment, a communist, and a socialistic anarchist, since 2000 Jim has led Craigslist to be the most used classified ads in any medium, and one of world’s most popular web sites, while maintaining its public service mission, noncorporate vibe, and staff of 20 or so.
Before devolving into management, Jim contributed Craigslist’s home page design, multicity architecture, discussion forums, search engine, community moderation system, self-posting process, personals categories (including missed connections), and best-of-craigslist.
Prior to Craigslist, Jim directed Web development for Creditland (defunct) and Quantum. In 1994-1995, he built the terabyte-scale, database-driven Web interface at the Interuniversity Consortium for Political and Social Research (ICPSR) through which researchers worldwide access the primary data archive for the social sciences.
After graduating summa cum laude from Virginia Tech (biochemistry), Jim attended medical school, studied classics, and made tofu at the University of Michigan. Now, alas, it’s mostly business reads for him.
Ridiculously tall, Jim has been the subject of feature stories in the New York Times, the Wall StreetJournal, the Financial Times, Fortune magazine, BusinessWeek, the Guardian, the Daily Telegraph, the Sunday Times, and SF Chronicle, and has made dozens of television appearances, including being denounced on Fox News by the late Reverend Jerry Falwell.