An Excerpt from I Hate People!: ‘The Secret of Craig’s List’

Today’s story comes from the authors of I Hate People!, Jonathan Littman and Marc Hershon. In addition to their book, they’ve been blogging about the people who make work painful — the Ten Least Wanted — and how to rise above the masses they call Sheeple to become a Soloist, someone who works well with a group but excels when they have the freedom to apply themselves as an individual.  They got a chance to have an extended conversation with Craigslist.org founder, Craig Newmark:

The Secret of Craig’s List

By Jonathan Littman and Marc Hershon

“As a Manager I kind of suck” – Craig Newmark

Unemployed. Stuck in a crappy job. Reduced to auctioning off your possessions on Craig’s List. Here’s the good news. Today’s despair may fuel your success. You may never win a popularity contest, but the freedom and happiness of a Soloist is within your grasp.

Consider the remarkable tale of Craig Newmark, founder of Craig’s List (www.craigslist.org), the world’s largest Internet classified pages, where you can find everything from a new bicycle to a girlfriend and an apartment to house them.  

Instant Internet success, right? Wrong.

Craig kicked off his programming career with IBM in their Boca Raton office, then nearly ten years in Detroit and the last couple in Pittsburgh.  Craig considered many of his years as a programmer pretty good. By the end it wasn’t so good. He was stuck in a marketing branch office. For a technical man such as Craig, it was a bad fit. “I lived la Vida Dilbert,” he confessed to us. “Sometimes I would alienate people. It didn’t matter if I was right. I was clumsy.”

Fortune struck. By 1993, IBM had hit a rough spot. As Craig put it, “the company was kind panicky. That wasn’t pleasant.” Like a lot of folks Craig believed in the giant multinational corporation that had been his lifeblood for nearly two decades. Why would he do anything else in his life? He was a skilled programmer. A full-on nerd, but IBM had thousands who fit that category. “I kept hanging on thinking things would be better. That someone as technical as me would find an opportunity.  I was wrong.”

How easily that might have been the short, sad tale of another unfilled corporate cog.

It was an age when the marketing wonks at IBM resented the geeks. Craig realized he wasn’t going to be happy. He sought out new opportunities in California. He boldly lined up interviews and landed a meeting at Charles Schwab. He got the job and excelled at the giant financial firm but found new problems. “The atmosphere was very political,” he recalls. “Infighting was more important than getting things done.” Craig noticed how the company seldom gave credit to the guys who actually did the work.

It was one of the things that bugged Craig about big companies.

Not sharing.

Then Craig got lucky. “Schwab had a bit of an implosion, and I decided to take a buyout and try freelancing.” Surprisingly, fellow workers at Schwab had told Craig he’d earn more and find better opportunities by striking out on his on. Craig says he made a misstep or two along the way, but then won some plum contract jobs, among them, helping Bank America develop its Home Banking. Oh and like a lot of geeks he thought that Internet thing was cool. He dug the giving part of it. “I though I should give back a little myself. I listened more and decided to start a simple cc list.”

He can only guess at his official launch — around March of 1995. Craig began Craig’s List, a crude list of people wanting to sell stuff — furniture, bikes, apartments, not to mention that other feature of the newspaper classified, men looking for women, women looking for men, men looking for women and men… He had no intention to build a business. “It was just something I did. It felt good. I was connecting with people.”

Unlike some new ventures, Craig’s List was not an instant failure — or hit. “It was very slow. Gradual.” Still within a few months, someone told Craig he had accidentally built a brand. Two years after Craig began his hobby, he hit some milestones. First, about a million pageviews a month. Then Microsoft wanted him to run their banner ads. Craig thought it over. “I felt I was already paid more than I needed as a contract programmer,” he recalls. “I do regard banner ads as frequently annoying.”

And so, Craig Newmark, bless his heart, said no to Microsoft.

By 1998, Craig reached that make or break point for the successful Soloist. Though he was running the operation out of his modest San Francisco home, Craig’s list was growing so fast he needed lots of help. He tried turning over his hobby to volunteers. “Someone needed to assert leadership,” he says frankly. “I didn’t. As a manager I kind of suck.”

Craig admits it wasn’t easy but he was finally talked into turning his hobby into a real company — incorporating, hiring a manager and staff. Today, it’s still nearly run like a non-profit. Most listings are free, except for job listings and real estate. Experts estimate 2008 earnings at $80 million, with an eye popping 10 billion pageviews a month. Henry Blodget ranks Craig’s List as one of the world’s top 25 most valuable startups, and postulates that if Craig ever wanted to sell the darn thing and actually bothered to charge for all the job adds on the site, “we’re conservatively looking at a business worth $5 billion.”

This from a hobby. From a geek who could have easily remained an anonymous programmer the rest of his life. Craig exhibits no visible profit motive. The notion, as he says, “that we’ve helped out millions, maybe tens of millions of people,” appears to give him the most pleasure. “It is a service.”

If not for IBM hitting a rocky spot in the early 90′s, Craig might never have discovered his Soloist gene. “I’d say people need to listen to their instincts,” he says. “If they’re not happy, they need to look elsewhere.” Craig said he was in denial for a long time at IBM, and probably should have gotten out six years before he did.

Like a lot of Soloists who have written their own ticket, Craig can do his own thing now. He remains an unapologetic nerd. Unlike some entrepreneurs, he shows no compulsion to start a second or third new company.  He comes across as a character out of a Dilbert cartoon who figured out how to play the game despite or, perhaps, because of himself.

Excerpt from I Hate People! / ©2009 Little, Brown & Co.