Conversations #68: Craigslist Founder Craig Newmark – Disruption & The Early Web

Women Who Code Conversations 68     |     Spotify – iTunes – Google – YouTube – Text
Tara Hernandez, Vice President of Developer Productivity Engineering at MongoDB and Board Member for Women Who Code, interviews Craig Newmark, Founder of Craigslist and board member and advisor for dozens of organizations. They discuss Craigslist’s beginning and continued simplicity from a technical perspective and Craig’s shift from manager to customer service and then into philanthropy.

You were one of the first internet disruptors, if not the first. Craigslist is to classified ads as Uber is to taxis. Tell us a little bit about how that got started. Was the original email done like Listserv?

In early ’95, I left Charles Schwab. I observed that many people in San Francisco had helped me out. I figured it was time to give back. I was starting to work on the early web. I was using email like Pine character mode. I would send it out when somebody told me about an event that usually combined arts and technology. It grew by word of mouth. First, it was a copy list, a CC list, using Pine. I moved to a list server in the middle of ’95, and the deal was that when you use a Listserv, you have to give the thing a name. As a nerd, I’m very literal. I wanted to call it San Francisco Events, but people around me told me they were already calling it Craigslist. I had inadvertently created a brand.

They explained to me what a brand is. Seriously, I didn’t know. People around me named it, and I put it all onto a major-domo and just kept plugging it away. In ’96, I realized that I was a programmer. I could write code and pipe what happens within Pine into Perl scripts. I had instant web publishing essentially for free. Back then, I paid no more than 35 bucks a month for web hosting, and that was a bargain, and it was all still pretty low volume. The World Wide Web was still very much in its infancy. The internet has been around for decades. This new internet was very nascent, so many email lists like Craigslist, the original version, Bulletin Board systems, or BBSs, were starting to wander over to this newfangled HTML thing. The neat thing about Craigslist was that it was not only early into the World Wide Web but also built using a lot of open-source technology. Open source itself was an evolving community of technologies.

Craigslist was written in Perl. People forget about Perl, but it was pretty cool back then regarding what you could do with it. Tell me a little about how you engage with the open source, selection, and tool selection. Other things were coming out. Were you playing with things, trying stuff out, or copying from others? 

In a way, what I was doing was all of the above. In its early years, the site was hosted variously on Solaris or Linux systems. Something about the spirit of open source appealed to me, which may have been the influence of The WELL since I was a very early WELL user. I was greatly influenced by the spirit of open source and community. I did use Bulletin Boards a little, I was on Prodigy, not very long and not very seriously, possibly CompuServe, but The WELL was the big one for me, the most influential. I still maintain a nominal presence there.

I made several painful decisions during Craigslist. One of which was to step down from management entirely. I had already given up coding, and I realized that as a manager, I suck. I turned it over to Jim Buckmaster, and I just went into full-time customer service. So I haven’t coded for a long time. I miss it, but it would be a distraction for me right now. I continue to do customer service, but I’ll only do that as long as I live.

You were almost 20 years at IBM if I recall correctly. You were at Bank of America and, as you said, at Charles Schwab right before Craigslist. I’m curious, what was your experience with the presence of women in programming and systems engineering? 

It was very surreal and disappointing, starting in the early ’70s. In the early ’70s, I was caught up in that wave of feminism. There were several women in graduate school at Case Tech, and it seemed like the number was increasing. I thought I saw an increase from there at IBM in Boca Raton, but something was happening, and I wasn’t quite conscious of it. The number of women in the field started decreasing. There was a problem with harassment, lack of advancement, etc.

It has only been in the last 10 or 20 years that people clued me in, and now I have the resources to do something about it. Particularly in cybersecurity, where the opportunities are great for everyone. I’m supporting major inclusivity efforts, including several groups starting with K-12 education, like Girls Who Code and, for that matter, the Girl Scouts. Then going beyond that, like the Drop the Mic effort and Women in Cybersecurity. I’m trying to support coding efforts, but I see an imperative need in cybersecurity, if for no other reason than to defend the country. We need everyone who can help to participate. It’s kind of like World War II. If you had the skills and the time, you were expected to play a role.

You started to move into philanthropy as your full-time job. You had a foundation, and then you ended the foundation. Now you’ve gone into more of this advisory and funding sort of other organization models. What has your path been through that? Is it part of finding your strengths, like the difference between being a manager versus a customer service person? Did that come into play? 

In the last 10 or 20 years, even at Craigslist, nonprofits have come to me not so much for contributions but for community building online. That evolved over the years, but then I started realizing, what I’m interested in, what could have beneficial effects, not only for the country but on a civilizational basis. I started learning what could be valuable. I started contributing somewhat more heavily in that direction. I started something called Craig and X, which was my clumsy and doomed effort to do something really good on a philanthropic basis that became Craig Newmark Philanthropies. That’s my way of doing a little umbrella work, including a foundation and a donor-advised fund. The deal is that the way tax rules are structured, it was easiest if I had both. That way, I could give away more money. The deal is, I’ve just kept on, kept keeping on, which in a way, is the entire history of my philanthropy. It does evolve in terms of focus areas. Pigeon Rescue is one of them. That’s because I love birds and have a sense of humor.

You could still run Craigslist on a 20-year-old computer without a problem. I think there’s a certain sustainability to that that I really appreciate.

People sometimes need a hand getting through the day. Sometimes you have to find a way to put food on the table. Sometimes you have to buy a table, and sometimes you have to find a roof under which to put that table. You want something fast and simple. You want something obvious to use. Obviousness is a good design principle.

You’re associated with so many different organizations. Do you see people stepping up, particularly women, in these roles, expanding that idea of community, of common interest, maybe a wider community that could be your next gift to the worldwide web? 

Please don’t give me too much credit. In all these efforts, I’m winging it, which may be working. I have the advantage in philanthropy of not knowing what I’m doing but talking with a lot of people and then finding people who are good at stuff to follow through with these things. As far as I could tell, roughly two-thirds or so, maybe more, are women. I should conduct a census among the mailing list I run for my grantees. I call it Craig’s New List because I don’t have any imagination, but I have a sense of humor. The people helping me make real things out of the focus areas I support, for the most part, if not completely, are women. I’m supporting something called Reporters Mutual about affordable lawsuit insurance in the media.

Can you speak a little bit about what that org does? 

They’re trying to figure out counter-harassment methods, focusing first on women journalists as they get it badly. But also people in journalism, freelancers, and small news organizations. They’re always in danger of getting hit by frivolous lawsuits, which can put them out of business.

Women Who Code partnered with VMware called TAARA in India. The initiative was about creating better opportunities for women to participate in the workforce, despite being moms and the challenges around coming back from maternity leave or maybe longer-term child care. What do you think the importance of those types of things is from what you’ve seen? 

Treating people like you want to be treated, we need certain resources to make things happen for the workforce. For example, affordable, trustworthy childcare that’s a big component of the Marshall Plan for Moms. My deal is that I find people who are good at things and then provide them with resources to move ahead. The resources generally combine money, influence, and communication—childcare for everyone that’s a big part of the Marshall Plan.

Any last thoughts that you would like to share?

I’m probably best known as the founder of Craigslist. I believe in the mission of Women Who Code because the deal is that we need to be fair to everyone. We need to empower diverse women in their quests for technical mastery. Whether it leads to a career or whatever people choose for themselves. Right now, women only make up about 26% of technology jobs, meaning we’re missing out on a huge portion of the population that can contribute. That contribution can involve unique perspectives, new ways of thinking, and innovations because that’s one way to build a future. If you want to build a future, sometimes the best way is to invent it yourself. That’s why on GivingTuesday, I’ll be matching contributions to support Women Who Code up to $75000. Please join me in supporting this important cause. We want to build an inclusive technology and representative of everyone.

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Guest: Craig Newmark, Founder of Craigslist and board member and advisor for dozens of organizations
Host: Tara Hernandez, Vice President of Developer Productivity Engineering at MongoDB and Board Member for Women Who Code
Producer: Kimberly Jacobs, Senior Communications Manager, Women Who Code
Producer: JL Lewitin, Senior Producer, Press and Digital Content, Women Who Code