This interview originally appeared in the SPRING 2017 issue of The District.

Craig Newmark is the founder of craigslist and the Craig Newmark Foundation. He graduated from Morristown High School in 1971.

Craig Newmark is a self-described nerd, Web pioneer, speaker, philanthropist, and advocate of technology for the public good.  In 2012 he was inducted into the Internet Hall of Fame. In 2013 he was named “Nerd-in-Residence” by the Department of Veterans Affairs’ Center for Innovation in recognition of his volunteer work with the department to enhance services to veterans. In 2016 he created the Craig Newmark Foundation.

Craig is the founder of craigslist, the almost completely free online classified advertising site that has seen more than 5 billion ads posted. While no longer part of management, Craig continues to work with craigslist in customer service.

Craig uses his craigconnects platform to promote philanthropy and civic engagement, supporting effective organizations working for veterans and military families, trustworthy journalism, voting rights, peer-to-peer giving, women in tech, and other areas. 

Craig serves on the board of directors of the Poynter Foundation, Center for Public Integrity, Sunlight Foundation, Consumers Union/Consumer Reports, Blue Star Families, VetsInTech, Firls Who Code and Iraq and Afghanistan Veterans of America.  He also serves on the Board of Overseers of the Columbia Journalism Review and as an advisor to nearly twenty other renowned non-profit organizations (see the full list at craigconnects.org/organizations). 

Born in Morristown, New Jersey in 1952, Craig received his bachelor and master’s degrees in computer science from Case Western Reserve University.  He lives in San Francisco and enjoys bird-watching, squirrel-watching, science fiction, and TV.

Craig communicates regularly through his own blog on craigconnects.org and through the Huffington Post, Facebook, LinkedIn, Medium, and Twitter.  He also travels the country speaking about issues, appearing on behalf of organizations he supports and delivering his craigconnects message to audiences nationwide. 

MEF: Tell us a little bit about your journey since high school?

I left high school pretty much the stereotypical nerd, completely lacking in social skills, socially isolated, though I'd abandoned the plastic pocket protector and thick black glasses (taped together.)

College, unfortunately, was not much of a learning experience, socially, and I was mostly still socially isolated, barely growing in that regards.

In the work world, forty years ago, I was in a situation where I had to play well with others, and slowly began to do so. Maybe working at IBM forced that on me, particularly when I got a field position. I had to work with other IBMers and with many customers and had to acquire the skills to do so. It helped, in the field, that I had to dress a lot better, and that matters.

Somehow, slowly over those twenty years, I started acquiring the ability to, at least, simulate social skills.

I've been doing craigslist for the last twenty years or so, doing customer service all that time.  It was pretty high intensity for most of those years, though I've relaxed recently. Customer service, if you take it seriously, involves communications and empathy, and that'll teach anyone social skills, or at least their simulation. That's where I am now.

FYI I maintain a very understated, dry sense of humor, and might state matters in such a manner as to amuse myself.

MEF: How did craigslist come to be?

I started craiglist as a hobby, just some emails about interesting things going on in San Francisco. The first were mostly about two events: Joe's Digital Diner, where people would show the use of emerging multimedia technology. About a dozen of us would have a dinner of spaghetti and meatballs around a big table. There was also a party called the Anon Salon, which was very theatrical but also technology focused.

Those first emails only went to a few folks -- 10 or 12. Then other people started emailing me, asking for their addresses to be added to the cc list, and eventually to the listserv. As tasks started getting onerous, I would write some code to automate them.

At first, the email was just arts and technology events. But I listened to people – they started asking if I could pass on a post about a job or something for sale. I could sense an apartment shortage growing, so I asked people to send apartment notices, too.

By the end of 1997 I realized craigslist was becoming a thing. It was still just me doing it, and at the end of that year I hit about a million page views per month, which was pretty big then. Microsoft Sidewalk [at the time a network of online city guides] wanted to run banner ads. But I said no, I was thinking people were already paying too much for less-effective ads, so we could provide a simple platform where the ads would be more effective and yet people would pay less. That made sense at the time and has worked out pretty well.

I was getting increasingly serious about the site and had gotten some volunteer help, but at the end of 1998, some people who had been using the site for years told me that using volunteers wasn’t working. They said I had to get real and make the site into something reliable.

I had been in denial, but I could see things were starting to not work. Postings didn't get done in a timely way; the database didn't get pruned of old listings in a consistent way. Trying to run a business collecting fees for job postings--I couldn't make it work on a volunteer basis. Maybe someone with better leadership skills could have, but I couldn't. So I had to get real and go full time. I had to commit. I left what I was doing--programming for a company called Continuity Solutions--and I made craigslist into a company in early '99.

I was talking to a lot of bankers and VCs, and they were beginning to fantasize about what the internet could be. They were telling me to do the expected Silicon Valley thing and monetize everything. They were saying craigslist could be a billion-dollar company. But I had already made the decision to not highly monetize when I turned down the banner ads.

About that time people helped me understand that, as a manager, I kind of sucked. I had trouble making tough decisions. I was not any good at the job interview process, and I found it very difficult to fire anyone. I didn't make major decisions that required some boldness, like adding new cities. I knew we needed to expand in that way, but I guess I didn't have the guts to do it. I was trying stuff that didn’t work, like running some ads for job postings in an HR magazine. But that wasn’t the right way to go -- word of mouth is what really worked.

I made one really good hiring decision, which was choosing our current CEO, Jim Buckmaster. I saw his résumé at the end of '99 and hired him around then, as our lead tech guy. I figured he could run things better than I could, and I was right. Craigslist is now in 700 cities in 70-some countries, and it’s kind of a household name, even if I’m not.

MEF: What are you most proud of?

I'm very proud of craigslist as a means of helping people in the here and now, and introducing the Internet to large numbers of people as a useful tool for anyone to use.  It's a great form of civic engagement.

Also, I'm proud that I've stuck with values learned in Sunday School in Morristown, that ...

- I should treat people like I want to be treated

- I should know when enough is enough

Knowing this helped me avoid temptation, and to turn down huge cash when I made craigslist into a real company.

MEF: What was your favorite memory of Morristown High School?

There was high school choir, a lot of fun since I was a true bass, and had a decent sense of pitch.

I also really enjoyed the use of the first computer there, an IBM 1620, and also being on the debate team.  Downside was that both reinforced the illusion that logic and reason matter much in human affairs.

Important memory: learning in history the role of the Bill of Rights, and that "a trustworthy press is the immune system of democracy."

MEF: What of your success would you attribute to your experiences at the high school?

In high school I got a really good education, including areas that I neglected in college, particularly humanities.

Aside from the obvious value of a good education, I think high school formed attitudes which are useful that I can't quite articulate right now.

MEF: What advice would you give a MHS student?

Take your educational opportunity seriously; if you screw it up, won't really be much of a second chance.

MEF: If you had known then what you know now, would you have done anything differently in high school?  If so, what?

I would have asked for help and learned social skills.