The Interview: Craig Beyond the List

By Janet Reilly

The Craigslist founder is focused on an entirely new kind of venture: Philanthropy. (Cody Pickens)

We recently caught up with Craig Newmark, who shares the extraordinary story of Craigslist, his commitment to philanthropy — and his passion for photographing birds.

There’s unassuming and then there’s Craig Newmark — of Craigslist fame — unassuming. Newmark, one of the original tech billionaires, doesn’t own a car, doesn’t have a personal assistant, and, until recently, provided customer service for the online classified advertising site he founded in the late ’90s. What began in 1995 as an email distribution list to friends quickly turned into a juggernaut company now valued at $3 billion by Forbes. And although the company bears his name, Newmark realized early on that sitting in the C-suite just wasn’t for him, handing over the CEO reins to Jim Buckmaster in 2000.

These days, Newmark spends the bulk of his time on philanthropy, with a major focus on funding trustworthy journalism (in just the last five years he has donated nearly $200 million to the cause), voter protection, women in tech, and veterans and their families.

In a recent wide-ranging Zoom interview, we discussed social skills, tech and his well-known love for birds. Meet Craig Newmark.

I’m going to take you way back. You grew up in Morristown, New Jersey. What was a young Craig Newmark like? Well, back then I had no social skills whatsoever. Even now, I’m only faking social skills. I even wore a plastic pocket protector. I wore thick black glasses taped together, and I was really good in science and engineering. Read a lot of science fiction, and would often drown my sorrows with cheap chocolate chip cookies and milk. Seriously.

As we all did! But you lost your dad at a young age, and I’m sure that had a profound effect on you. How do you think that helped to shape the person you became? It probably contributed to my social isolation. I had no good role model. My mother didn’t fill that role, and I had to do my own thing, which led me into a fair amount of social dysfunction. It was only when I was doing Craigslist customer service that I seriously grew out of that, but it was fairly bad.

After you left school, you went on to work for IBM and had a 17-year career there. Then on to Charles Schwab. What’s the single biggest takeaway from your corporate experience? If you get a good manager, they will fight for you. They will give you good career advice. If you get an OK manager, they may not achieve any of that. In either case, you’re responsible for your own career. You’re responsible for your own internal branding and image and even a good manager needs a lot of help from you regarding that.

Well, you must have done that very well. You must have advocated for yourself to have that lengthy career. No. I completely sucked at it. However, I was really good at my job being a systems engineer, so much so that people would make allowances for me when I was a jerk.

That’s always helpful. The only thing that’s really helped me grow was doing customer service online; that
evens out the rough edges, or at least most of them.

So, are you still doing customer service for Craigslist today? I am not doing customer service for Craigslist, but I’m busier than I’ve ever been with my philanthropic work, and I do customer service there. Between yesterday and today I’ve provided the most intense customer service I’ve ever done helping people fill out our grant request forms.

Craig Newmark. (Cody Pickens)

Why is it so important for you to be involved at this level? Well, partially because that’s my emotional
investment; I’m an engineer, and I do things hands on. Part of it is that I just can’t see myself using a personal assistant.

Let’s go back to the origins of Craigslist. It really is an extraordinary story.
Well, the origins are fairly simple, at least in terms of my role. Just after I left Schwab, I started a simple cc [email] list for people I knew, and I was talking about arts and technology events like the Anon Salon for Climate Theater
and also Joe’s Digital Diner. Three or four months in, the cc list I was using blew up and then I had to use a mailing Listserv and give it a name. I was going to call it “San Francisco Events” since it was still mostly that, but people around me told me they already called it Craigslist — I had created a brand inadvertently. They explained to me what a brand was because I needed help.

That made sense to me and so I kept plugging away. It kept growing, and when the site needed more of my time, I just wrote some software to automate some tasks. I tried volunteers in ’98 — that didn’t work. And at the end of ’98, people told me that either I had to make it into a real company or it was going to fail.

Did you ever think about taking Craigslist public? What would be the point? I don’t like fast cars and I don’t even own a car. I don’t need big houses. I already made enough money doing programming to live well and help my family and friends out. I do have indulgences. I buy all the books I want and I buy — not all the gadgets I
want, but at least half.

In 2016, you started Craig Newmark Philanthropies. And under that you fund many, many initiatives. In particular, you’ve given millions of dollars away to support journalism and protect press freedom. Why is this such an important issue to you and what do you hope to achieve? The principles are from high school history and civics taught by Mr. Schulzki in 1970. He said, “A trustworthy press is the immune system of democracy.” And yet in 2016, we were attacked by a hostile foreign power using information warfare techniques to place an asset in high office. It’s incumbent upon patriotic Americans to fight back, to work together, and to take the battle to the enemy.

I’m working with people in journalism, cybersecurity, studying disinformation and voter suppression. I’m working to try to protect the country because we are at war. My dad had World War II where he fought in the Pacific; I figure I have what Marshall McLuhan called “World War III,” a guerrilla information war fought without distinction between civilian and military participants. That’s the only thing he said that I ever understood.

With your knowledge of the internet and technology, did the 2016 interference in the election on social media platforms surprise you? Or were you one who said, “This is just sort of inevitable”? You know,I’ve read it in history and science fiction that it was going to happen butI had some naivete that it wouldn’t happen, or that the platforms and newspapers would deal with it. They didn’t in 2016. Now, some of the plat-forms and newspapers are starting to fight back. It is not too late.

Though Newmark claims he “doesn’t do fun,” he appears amused by obsequious displays of attention at his bar mitzvah in 1965.

Are the social media giants doing enough to rid their sites of disinformation? And even if they have the best intentions, is it possible? They’re starting to. The journalists and reporters, and people who work in the social media companies like programmers and marketing people, they all want to do the right thing and fight back. It’s harder to get highest-level management to do that because that threatens the profit of those companies. And it threatens the safety of the people in charge. Remember the bad actors — whether they’re foreign adversaries or their domestic allies — they fight dirty. It takes a lot of moral courage to fight back. I should be fair here. I don’t know if I have the courage. I’ve already been attacked in unpleasant ways, but I’m still fighting back. But I don’t know when my courage will fail.

You’ve been attacked because of your work on cybersecurity? I’ll be very vague because of work with law enforcement, but if you support the good guys fighting the actual fight, you will be noted as a target and it does get ugly.

I interviewed Kara Swisher in late 2018. Of course, we had a lot of discussion about this, and she said these companies should have seen these problems coming, and they did see them coming a mile away, whether it be privacy issues, cybersecurity issues, misinformation. Do you have a strong feeling about that? I know how hard it is from a technological point of view to do this. I don’t focus on what people missed versus what could be done now, because a lot of this work requires machine learning technology which doesn’t exist yet. But sometimes you find chronic abusers with large influence and you can do stuff to down-rank them, and some of those things are easy. It just takes courage.

Let’s go back to your philanthropy. You don’t just give money away; you really engage in conversations with people about these issues. Like you’re doing with me today, you do it on social media a lot. You do it in symposiums. You give talks. Are you just a hands-on guy? Have you always been an activist at heart? Yeah. You should practice what you preach. The deal is, I’m also an engineer and I prefer to do things. Right now I’m busier and feel better about what I do than ever. It’s like I was born to do this.

Would you describe yourself as a facilitator of change? That’s accurate. One approach in philanthropy is to share power. My variation of that is that I give away power rather than accumulating it because I have no interest in accumulating power and I could be way more effective by giving it away. That’s power as expressed in dollars and influence.

What kind of vetting process do you go through when choosing whom to give money to? These days I cheat. I did a lot of research and I found people who really know a specific area, like disinformation or cybersecurity, and then I get help from them. The only area where I need that kind of coordinated help is women in tech because I’m now supporting a whole bunch of women in tech efforts, like the Girl Scouts and Girls Who Code, and I need to find someone who I can probably fund to give me expertise. For veterans and their families, I get help from the Bob Woodruff Foundation.

Newmark (shown in a 1971 graduation photo) cites civics lessons from his days at New Jersey’s Morristown High School.

What do you do for fun? I don’t do fun.

Come on. I read a lot. I watch TV. I spend time with Mrs. Newmark. We do watch birds.

Yes. I enjoy your bird photography on your Facebook page. Where did your interest in bird watching come from? I have no idea. And yet it’s been happening longer than I thought because I saw some photos I took in the mid-’80s when I lived in the Detroit area and I actually had a bird feeder and we got a lot of birds.

You seem to be very grounded and centered. What keeps your feet on the ground? Well, I grew up hovering somewhere between poverty and middle class, which helps. Doing customer service keeps you real and I’ve done it for a total of 37 years, between IBM and Craigslist and philanthropies.

So, what’s next for Craig Newmark? More of the same. I have to become a lot more effective in helping other people bring the battle to the enemy. For example, there’s the Election Integrity Partnership anchored
by the Stanford Internet Observatory, which I funded. Yesterday, I funded another component of the overall
effort not announced yet. I just learned by accident recently that my father was some kind of combat engineer in World War II. I am a combat engineer.

Janet Reilly is theGazette’s co-owner and monthly columnist. She is also the former executive producer and on-air television host of The Mix With Janet Reilly.

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