Craig From Craigslist’s Second Act

Craig Newmark has been really into birding lately. The habit began a few years ago, by accident, much like his famous “list.” When he wasn’t answering customer service emails from Craigslist users — something the 64-year-old tech icon still does to this day — he’d flip through TV channels until he hit a nature special. Eventually he built up enough bird knowledge that he could identify different species from his Cole Valley, San Francisco, patio, where he and his wife, Eileen, have seen more than 50 types, as evidenced by his bird-heavy Instagram and Facebook pages. His favorites, by the way, are hummingbirds and California towhees, “which sing great,” and robins — he gets a lot of robins.

Occasionally San Francisco’s storied flock of cherry-headed conures will pay a visit, and the other day Newmark was pleasantly surprised to see a band-tailed pigeon (what he excitedly describes as “a pigeon with a necklace”). In the West Village, where Newmark recently bought an apartment, he eyed a cardinal carrying around nesting material. Newmark considered putting out food to encourage it to stay and build its nest. But he knows that interfering with a natural habitat can have consequences.

“If you put out food to attract birds, it also attracts rodents,” he said.

You could say that Newmark learned a thing or two about messing with ecosystems as an early internet pioneer. When the former IBM programmer first started sending out a list of tech events and opportunities to a dozen or so friends in 1995, he was only hoping to cultivate a bit of community. But after the list’s subscribers multiplied, Newmark turned it into a site for online classifieds. At first it was just a well-intentioned tool meant to help people find couches or jobs or the cute person they made eye contact with on the subway. But as the site grew, it also became a vehicle for scammers to scam, for killers to kill, for sex traffickers to traffic, and for many more depraved things people do when they think no one is looking. On top of all that, Craigslist was accused of killing newspapers. As its free online listings became a go-to resource for most major cities, local print publications everywhere saw a cut from their own classifieds revenue. A 2005 American Society of Newspaper (now “News”) Editors convention presentation included Newmark’s image — that of a smiling, stout bald man in a Kangol newsboy cap — in a presentation examining the industry’s crisis. A year later, New York magazine dubbed him the “Exploder of Journalism.” A business columnist for the San Francisco Chronicle at the time called upon Newmark to do more for the landscape he ravaged: “You shouldn’t take the money and run,” he wrote. “[You] need to give something back to society other than cheap apartment ads and funny, dirty personals.”

Newmark didn’t run. The man who was once universally billed as a newspaper killer has now positioned himself as a fierce advocate of trustworthy journalism, donating millions to mainstay journalism centers like Poynter and ProPublica, and partnering with companies like Facebook to address the issue of fake news. “I’m a nerd in the old-school sense,” he said. “I’m pretty literal. And it’s hard for me on an emotional basis to know why anyone would say anything other than the truth.” You could bill that as a typical Silicon Valley futurist move: disrupt an industry, then pepper your profits on its decaying remains. But Newmark’s interest in preventing fake news from spreading online has spanned for a much longer time than the media has cared to cover it. In fact, his sustained interest in the cause was inspired by a personal experience: In 2010, his company was under fire for a CNN investigation that showed the site’s “adult services” section was being used for underage sex trafficking. Craigslist eventually shut down the section, but he says that at the time it was working with the FBI to track criminals though the site. Because Newmark wasn’t able to offer details of his collaboration with the government to reporters, he says the media speculated to fill in the gaps.

“The company had mounted a massive law enforcement program, and the company really couldn’t talk about it,” he said. “And that provided an opportunity for a false narrative that proved to be pretty unfortunate.”

Newmark is still not authorized to share the details of Craigslist’s collaboration with the FBI, but in 2015 he says the company received an award for its help in combating human trafficking.

“Basically, tech people who start their own companies, we don’t really expect to be blamed when we do the right thing,” he said. “That always catches us off guard, and usually it takes a long time for us to learn about it.”

At this point, far more advanced tech companies like Twitter and Facebook have replaced his company’s role as the media industry bogeyman. And as journalism experts and Silicon Valley companies rush to examine the reaching effect of fake news in our communities and politics, Newmark has drawn from his estimated $1.3 billion net worth to bolster a handful of organizations he hopes will strengthen the reliability of the industry, alongside efforts to help women in tech as well as veterans. Last year he gave Poynter $1 million to fund a faculty chair in journalism ethics, declaring that he wanted “to stand up for trustworthy journalism” and “against deceptive and fake news.” In March his philanthropic fund gave $1 million to ProPublica. The next month, it was one of the organizations, along with Facebook and others, that started a $14 million News Integrity Initiative dedicated to creating a more news-literate public. Newmark’s decision to buy an apartment in New York and “go bicoastal,” as he put it, was largely because of his involvement in East Coast–based journalism nonprofits. He also blogs frequently about other efforts he finds commendable on his charity website, Craig Connects, and in an Atlantic article published earlier this month he argued that news organizations should do more to assess the risk of online threats directed at their reporters. “We need to start, somewhere,” he wrote. “Harassment and intimidation of reporters is a real problem, with real consequences for democracy.”

Newmark’s charitable interest in journalism didn’t start the moment that Donald Trump became president and the world began to fret about social media echo chambers. (Even though Newmark clearly has liberal views, and has donated to both Barack Obama and Hillary Clinton.) The self-proclaimed “dysfunctional nerd” has dabbled in press-related charity work since his company first came under fire for stealing away newspaper profits. In the mid-aughts, he defended his site’s effect on the media, once describing it as “a process of creative destruction, kind of like the replacement of buggy whips by car parts.” Nevertheless, he acknowledged that a “vigorous press” was “needed for the survival of any democracy.” That’s around the time he began throwing cash at efforts that piqued his interest, though he hadn’t yet settled on what cause he really wanted to dedicate himself to (at this point, he hadn’t started his foundation). In the mid- and late aughts, he donated to reputable organizations like the Berkeley Center for New Media and to a site run by CUNY professor (and well-known Twitter parody foe) Jeff Jarvis that attempted to help the media cope with its shattered online identity. For a time he also worked with a handful of organizations exploring the viability of citizen journalism — an idea that eventually fizzled out with the rise of social networks like Twitter.

Newmark readily admits that he is not an expert in the field of journalism, and he will not solve the fake news problem single-handedly. Mostly, he wants to give his money to people who know what they’re doing, and bolster a lesson that his high school history teacher taught him: that “a trustworthy press is the immune system of democracy.”

“I know reporting is really hard. I’ve never had to write to deadline five or more times a week,” he said. “But I know how tough that is, particularly with fact checking. I’m an outsider. I’m just a news consumer. I just want news I can trust.”

Even if he won’t explicitly say it, Newark’s efforts are also about his legacy as an unusually modest company founder. Rather than pushing his company to expand its services, staff, and products to eBay-level sizes in the early days, he helped build a modest and profitable site that had revenue of $694 million in 2016. (He’s still on the board, but hasn’t managed the company since 2000.) Newmark despises the attention that his celebrity has earned him, but he’s learned over time to use it to promote his charitable causes, appearing to speak at ritzy private establishments like the Core club to lend his name to Women’s Entrepreneurship Day. He chalks up his success to knowing his limits early on in the company and running with them.

“Basically I just decided on a different business model in ’99, nothing altruistic,” he said. “While Silicon Valley VCs and bankers were telling me I should become a billionaire, I decided no one needs to be a billionaire — you should know when enough is enough. So I decided on a minimal business model, and that’s worked out pretty well. This means I can give away tremendous amounts of money to the nonprofits I believe in … I wish I had charisma, hair, and a better sense of humor,” he added in a completely deadpan voice. “I think I could be far more effective.”

Though Newmark has graduated from using Craigslist to search for major life purchases, the service still plays a role in his life. He’s used it to buy and sell small electronics, and unloaded his last car there too. But lately he and his wife are trying to shed their belongings, not accumulate more. The two recently decided to live without a car, and lately his wife has been using Craigslist to give stuff away.

“We both feel we have too much stuff, and should live with as little as we can,” he said.

Being just a little more humble and a little less greedy than most modern tech founders may be Newmark’s lasting mark. Mostly, Newmark says he just hopes that future technologists follow the Sunday school rule he did: to treat people like you want to be treated.

“Ideally I would be remembered because I was really funny,” he said. “But I’m not. I guess I would just like to be known as a counterexample. Just because you can make millions of dollars, you don’t need to. I realized only in recent years that having lots of money impresses people in ways that can help your charitable efforts. But given my nerdly dysfunction, that’s pretty grating.”

This piece was updated after publication to correct the type of bird Craig Newmark saw in New York. He thought it was a Stellar’s jay, but later realized that it was a cardinal.