Getting There: A Book of Mentors (2015)
My high school years had some pain attached to them. I was the cliché of a nerd. I was into computer technology, wore thick black glasses that were taped together, used plastic pocket protectors, and had the social skills that go with the stereotype. I didn’t listen or articulate my ideas very well. I missed what other people found obvious. I just didn’t get it—whatever it was.
I went to Case Western Reserve University where I got both my bachelor’s and master’s in computer science. During a communications class, I had an epiphany: It couldn’t be everybody else who had a communication problem; it had to be me. This realization started me working on my communication skills. I still am.
After graduation, I had no real ambitions other than getting a job that was fun. Programming was fun, so I went with that. I worked at IBM for seventeen years. After IBM, I became an independent contractor, moved to California, and began developing web-oriented software for other companies. I worked for GM, Bank of America, and Charles Schwab. Unfortunately, most of the projects I worked on didn’t pan out.
But one of the big advantages of Silicon Valley is that failure isn’t stigmatized. It’s assumed that most ventures will fail, so actually doing so is not that discouraging. The important thing is to keep trying. I’ve talked to a lot of people on the East Coast and in the UK and learned that in those places failure is stigmatized. I think that’s why their business cultures have not been effective in some ways. Fear of failure can stop people from trying new things.
While I was writing software for companies, luck came along, and I stumbled on a new business while just trying to give people a hand. I noticed a lot of people using the Internet to help one another out. Growing up as a nerd, I knew what it felt like to be left out. But rather than being bitter about that, I figured I should do something inclusive. So in early 1995 I started e-mailing all my friends about cool events going on in the Bay Area that usually involved arts and technology. The news of my e-mails spread and friends of friends wanted to be added to my list.
It wasn’t long before people started suggesting that I branch out from just events. They asked me to post about jobs, stuff they had to sell, and apartment rentals. I listened to people’s ideas and implemented the ones that made sense.
By the middle of 1995, my list had hit 240 addresses, too many to be sent by one e-mail. As a result, I decided to post it on a list server, which required a name. I wanted to call my list S-F Events, but friends suggested naming it Craig’s List. They explained that this is what they all called it and that I should hold on to my brand. I didn’t know what a brand was, but I adopted the name anyway. But with a lowercase c: craigslist.
Having no design skills, I kept the site very simple. I also figured that most people like things that quickly get to the point. I still believe that.
Being a nerd, I’m pretty literal. If I say I am going to do something, I follow through. So I kept running craigslist as a hobby for a few years. By the end of 1997, I was getting about a million page views a month. It became a lot for me to deal with on my own, so I brought on some volunteers to help out. Unfortunately, that wasn’t too successful. In 1999 I realized that I needed to get serious. I decided to devote myself to craigslist full time, hire some really smart people, and incorporate it into a company.
I think it’s important to know when to get out of your own way. I suck as a manager. Luckily, I was aware enough to hire and promote a guy named Jim Buckmaster in time for craigslist to become what it is. I’m the chairman and founder, but Jim runs the company. Thanks to his presence, I’ve had time to launch craigconnects.org to help connect the world for the common good. I’m also active outside of my online comfort zone, working on issues for veterans and military families and others in need and also serving as a board member or advisor to a number of nonprofits.
Despite the fact that craigslist has become a serious business, it’s also remained a serious community service. We’re a simple platform where people can help one another with everyday needs. I believe we’ve endured because we’ve remained loyal to our roots. Our motto is “Give people a break.” We treat our users the way we would like to be treated and have worked hard to form a culture of trust. For me, this translates into a strong focus on customer service, which led to craigconnects and my other activities outside of craigslist. However, even today I continue to engage in craigslist customer service every day to stay connected with our community. We’ve continued to listen to suggestions from our users and act on them. Whenever we make decisions, we think about what’s good for the community. Although somewhat unusual in the business world, this way of operating feels right to us and has worked.
Every now and then, people come along and want to convince us to change the focus on community service that has led to our success and focus instead on short-term profits. I believe that this would be a mistake because our success as a company has been driven by our attention to what the community wants and needs. We are committed to this principle as our North Star to guide our way in the future.
People have sometimes asked me why (unlike many other founders of successful companies) I’m not interested in doing the usual Silicon Valley thing and becoming wildly wealthy. My answer is that once you’ve been able to make a comfortable living and prepare for your future, what’s the point in making more and more? I know some of the richest people in Silicon Valley and all that money doesn’t make them happier.
Brevity is the soul of wit. If you’ve got something to say, say it and stop talking. If you don’t have anything to say, you’re doing yourself and others a favor by keeping quiet. If you can’t make a contribution, don’t slow down the people who can. Most of my life I’ve probably been unaware of when to stop talking. I try to adhere to these rules, but not with complete success.