Craig Newmark is a man of quiet contradiction. Wrapped in a sweater the color of hot chocolate, the 66-year-old founder of Craigslist is painfully self-effacing, yet he started a wildly successful online marketplace emblazoned with his name. He deemphasizes his personal wealth, yet knows exactly how much he donated to his philanthropies last year (over $100 million). He speaks in vague terms about political "bad actors," yet specifically insists that a trustworthy press is "a matter of national security."
"I'm a dull and uninteresting kind of guy," Newmark says from the wood-toned living room of his San Francisco home. He is anything but.
You might expect Newmark to thump his chest about building the world's largest site for online classified ads from thin air. Or let slip his net worth, once estimated to be at least $1.3 billion. The privately owned Craigslist, is, after all, thought to earn $1 billion per year. Newmark would not reveal the percentage of his stake.
He would rather photograph a California scrub jay bobbing its blue-and-white head into the bird feeder on his back deck than boast about his achievements. Newmark keeps a Nikon Coolpix P900 in the kitchen for that very ornithological purpose.
"I'm not a birder," he says. "The contract that we've made is that I will put out food and water for the birds. And then they come over to be watched...How I got into it, I'll never know."
Accidental birder. Accidental billionaire. Deliberate activist.
For a man whose temperament begs to shirk from the spotlight, Newmark's extraordinary success thrust him unwittingly onto the national stage when he created Craigslist in the mid-1990s. It's brought in over 600 million visitors since June 2018, according to Comscore.
Now Newmark is welcoming the limelight, or at least the interviews and speaking opportunities that shine attention on his passion projects, which include helping women win technology jobs and promoting journalism, voting rights and veterans.
Newmark's dedication to journalism is another one of his seeming contradictions. He's credited by some with single-handedly taking down the newspaper classifieds industry and strangling local papers of revenue. In February, he gave $15 million to projects that support journalism ethics at a time of deep political divide over where and how we get our information, and how trustworthy those sources may be. Newmark never uttered the term "fake news," but he wants to fight it.
"I think it's wonderful," says Jerry Ceppos about Newmark's financial support. Ceppos teaches journalism at Louisiana State University and is a 50-year newspaper veteran who was executive editor of the San Jose Mercury News when Craigslist launched 24 years ago.
"I worry about...news deserts, areas where newspapers have gone out of business, or areas where news staff is so reduced that they can't do the kind of quality, time-consuming journalism that the Miami Herald did [on the Jeffrey Epstein child sex trafficking story]," Ceppos says.
Newmark worries about this, too. But to understand how we got from founding a company to his focus on the intersection of technology and trust and a new effort to train 100 women to become cybersecurity professionals in 100 days, we have to travel back to the beginning.
Newmark never intended to be a big shot when Craigslist first came online in 1995. Unlike Jeff Bezos, who founded Amazon.com the same year with grand ambitions — Amazon was dubbed "Earth's Biggest Book Store" at launch — the Craigslist story is one of unintended consequence that stemmed from Newmark's life as a nerd.
Like so many Silicon Valley startups of lore, Craigslist.org began at home. Specifically, in the living room of 1010 Cole Avenue, where Newmark's modest apartment — he's since moved — was one of three sharing a stairwell in San Francisco's charming Cole Valley neighborhood.
"The internet wasn't that much of a surprise to me in terms of what it was doing, what it could do and all that. Because, science fiction. Because, nerd," Newmark says, using one of his trademark phrases to refer to himself. "I've been reading, for almost 60 years, explorations of possible new technologies."
Born and raised in Morristown, New Jersey, with his younger brother, Jeff, Newmark first wanted to be a paleontologist, with a box full of "really cheesy" plastic dinosaurs to prove it. In his 'tween years, wearing stereotypical thick black glasses taped together, his attention shifted to physics. And then, during his freshman year at Case Western Reserve University in Cleveland, Ohio, to computers.
After 17 years at his first post-college job, helping IBM customers with technical support, Newmark moved to San Francisco in 1993 to join Charles Schwab to help set the company's future system architecture. In early 1995, he put together a social mailing list showcasing nearby art and technology events as a way to give back to his new community.
Word got out. People asked to join the cc list, and then asked for more categories. Newmark obliged. The barely budding venture didn't even have a name. He considered calling it "SF Events" or "San Francisco Events," but around him a new name was already coalescing: Craig's List.
Newmark embraced the suggestion, spelling his variation with a lowercase "c" to downplay his role — "craigslist." A personal brand, but only just.
Programming came naturally to Newmark, and as the internet began to unfurl, he whipped up an instant web publishing tool to convert the emails into a website. It cost him nothing. With that, the Craigslist we know was born.
"I really didn't know what I was creating," Newmark says. It just kind of happened.
Craigslist doesn't announce traffic numbers or revenue, but a fact sheet that was posted on the site said that more than 60 million people in the US visited the site each month and earned 50 billion total pageviews from around the world. It has since been taken down. Craigslist translates into 15 languages and has listings for every continent, barring Antarctica. In 2013, Mashable reported that the site reached over 70 countries worldwide.
All of that is driven by Craigslist's famously stripped-down interface highlighting categories for everything from job listings and housing rentals to a marketplace for used goods. Craigslist is still free to use, with companies and dealers (like housing or antiques brokers) paying a modest fee for certain posts. For example, it costs $75 to publicize a job in San Francisco and $35 in cities outside the hyper-expensive Bay Area.
The site focused on the San Francisco Bay Area for years, only expanding to other regions in 2000. That was also the year Newmark handed over the reins to Jim Buckmaster, Craigslist's current CEO. Why? Though he'd created Craigslist from scratch, it dawned on Newmark that he didn't have the chops to lead a business himself.
"I realized that as a manager, I kind of suck. And it only took me a few months for it to sink in, which, as founder's syndrome goes, isn't bad," he says.
Patience wasn't Newmark's forte. He recalls being a jerk, especially in his IBM days. Arrogant. Insensitive. He corrected others for mild inaccuracies just because he could. But working with people who relied on his efforts to make a living during his years at IBM and Craigslist, helped alter Newmark's perspective over the decades.
"Hopefully I haven't been a real jerk in a long time," he says.
Craigslist changed Newmark just as his internet venture changed the world around him, but what hasn't changed much in more than two decades is Craigslist itself. It retains the same bulletin board look of hyperlinked text used by other Web 1.0 brands of its day, like AltaVista, a Google precursor that indexed the web. Craiglist's home page has barely a capitalized letter in sight. And that's exactly how the founder likes it.
Retaining the early Web spirit isn't just important to Newmark. It's also important to Buckmaster, who famously said in 2006 that he doesn't care about milking profits for all they're worth. Buckmaster and other Craigslist.org employees didn't respond to a request for comment.
The role Craigslist plays hasn't changed either. The online classified listings for jobs, furniture, housing rentals and more will still, as Newmark says, "help you put food on the table. It'll help you get a table. It'll help you get a roof under which to put the table."
Putting food on the table and a roof overhead is one of Newmark's favorite sayings. He has a bushel of them. These mottos are, to him, as warm and familiar as an old sweatshirt: "Because, nerd. Put your money where your mouth is. Know when enough is enough." You can almost feel the creases in his voice when he says them, they're that well worn.
But to step into Newmark's world is to understand that these sayings aren't mere platitudes he shrugs on every day for the sake of catchy headlines. They seem to truly form the fabric of his belief.
After a few minutes, it's clear that the entrepreneur's San Francisco home is a sanctuary from his hectic life of appearances and inquiries. Newmark and his wife, the effortlessly serene Eileen (or Mrs. Newmark, as Craig referred to her), split their time between here and a home in New York, where they're closer to both of their families.
Warm woods and practical, comfortable furniture ease you into open, inviting spaces. A staircase leads down to the couple's private quarters built into a verdant hillside. It's the kind of place that makes a stranger feel immediately at ease. Once again I'm struck by how un-brotastic Newmark is, how Web 1.0 his mentality.
Far from the wild soirees and excess of startup culture painted in exposes and in TV shows like Silicon Valley, you can imagine Newmark padding around in Dearfoam slippers reading the Sunday paper with a steaming cup of regular-people supermarket tea warming his hands.
Figurines of The Simpsons cartoon characters dot the bookshelves, alongside a family menorah that crossed the Atlantic and books like L.A. Confidential and a sci-fi series by Neil Asher. On the wall, there's a portrait of Newmark communing with birds.
And Newmark himself? His musings are relatively tame, his eye contact shaky. ("I've learned to simulate social skills. I'm faking them even now," he says, not unsettlingly.)
From a simple armchair in his living room, he tells me that nobody really needs billions of dollars of personal wealth. What we need is to neutralize "bad actors" and make the world a better place. That's where his philosophy and philanthropy meet. It's like what his Sunday school teachers, Mr. and Mrs. Levin, taught young Craig all those years ago: Know when enough is enough.
"So far, I've given over $90 million for this combined effort of trustworthy journalism, cybersecurity, countering information warfare," Newmark says. "I've contributed a lot to other areas, like voter protection in the low millions, to teachers' education in the [pause] about 4 million — that's Donors Choose — and also contributed to vets in the higher single-digit millions."
"The deal is that, well, know when enough is enough. And stand up and do the right thing for people. Oh, and of course, put your money where your mouth is."
Craig's philosophy has earned him fans. "He's incredibly generous, very humble, funny. Peaceful. He's also a bridge-builder and fancies himself that, for good reason," says Jeff Jarvis, who teaches at the Craig Newmark Graduate School of Journalism, at CUNY, a beneficiary of Newmark's donations. Jarvis says he considers Newmark a friend.
But not all Newmark's ventures have panned out or been received so warmly. For example, his $20 million investment into The Markup, a data-driven platform for reporting on Big Tech and its effect on society, was to launch this year. Instead, it went up in smoke after its founding editor-in-chief, Julia Angwin, was fired in April before the site went live. (Angwin is now reportedly in talks to return. She declined to comment for this story.)
Despite the hiccup, Newmark's Donorpalooza is still going strong. In June, he gifted $6 million to Consumer Reports for a new lab to delve into data privacy and security issues. One of his more modest grants, $162,000, completely funded a Sacramento, California, program that kicked off in July to train 100 women to become cybersecurity professionals in 100 days. Cyber security will have 3.5 million open positions by 2021, of which women currently account for around 20%.
"[Craig's] doing such amazing work and I'm so deeply grateful. Without him, we wouldn't be having this program," says Carmen Marsh, CEO and managing partner of Inteligenca, her cybersecurity agency servicing small businesses in the Sacramento area.
An entrepreneur like Newmark, Marsh reached out to the founder through LinkedIn to ask for advice on running a successful Indiegogo crowdfunding campaign to self-finance the 100 Days program. Newmark immediately responded, and wound up financing it himself through a grant from Craig Newmark Philanthropies.
"It's a vote of confidence that this program is something very important," Marsh says. It's something that's going to enable women to upgrade their careers to something that's well paid. Marsh hopes that she can eventually expand the program to other cities, using Newmark's seed donation to generate momentum.
While his widespread philanthropic interests range from women in tech to voting to veteran support, nowhere is Newmark's contribution more visible than in the world of reporting. For Newmark, a robust and accurate press is nothing short of an expression of democracy.
"It's a patriotic act, to contribute towards stronger, more vigorous, trustworthy journalism," he says. "It is a national security matter. We need, as a people, to know what's going on with our government, with the world."
To date, Newmark has given the City University of New York a $20 million endowment. Students can now study there at the Craig Newmark Graduate School of Journalism. A $1 million donation to Poynter, a nonprofit research institution and journalism school, is another high-profile donation. Others include separate $1 million and $500,000 gifts to Wikipedia.
Becoming a champion of journalism is a choice that Newmark's newspaper critics — some still reeling from Craigslist's role in the decline of advertising dollars — won't ignore. They're quick to point out the irony. Craigslists' online classified ads devoured newspapers' main source of revenue, forcing national and local newspapers to downsize their staff or even fold because they didn't have enough money to keep up.
Researchers in 2013 calculated that Craigslist cost the newspaper industry $5 billion in revenue in seven years. Classified advertising revenues hit $19.6 billion in 2000, according to MinnPost, before nosediving 77% by 2012. Similarly, a Pew Research study found that the number of adults using online classified ads doubled between 2005 and 2009, naming Craigslist specifically as one of those sites.
Yet others have come to Craigslist's defense.
"[The critics] were completely wrong," says Jarvis, the CUNY professor, of Craigslist's then-detractors. "It wasn't about Craigslist, it was about the internet itself — getting rid of the middle man. And we were the middle man."
Craigslist let users post for free most of the same listings that newspapers of the day charged to print, Jarvis says.
"The cost of trying to sell a couch in a newspaper was prohibitive. The cost of an obituary was prohibitive — hundreds of dollars," he says. A 43-year veteran reporter, book author and podcaster whose biography includes writing for The Chicago Tribune and creating Entertainment Weekly, Jarvis worked at NJ.com when Craigslist began.
The New Jersey news site owned by Advance Publications had itself come online the year before, in some senses more a contemporary to Craigslist than a direct competitor.
Ceppos, the San Jose Mercury News' former executive editor and Knight Ridder News vice president, doesn't blame Newmark for the decline of print classifieds either.
"Classified was a huge proportion of the revenue, in terms of help wanted. Tech companies [were] trying to steal people from other tech companies," Ceppos says. "We were in the middle of Silicon Valley and it was just very clear that the internet was going to change our lives. We didn't know how much it was going to change our lives, but we could see that it would happen."
Newmark acknowledges that Craigslist played a role in whittling down newspaper revenue, but says that it's the television news and social media platforms that have most significantly transformed the media landscape. Today, quality news outlets are struggling, and that's a problem for Newmark.
To him, democracy is the linchpin of the country's continued civic freedoms. Exposing wrongdoing holds people accountable, which in turn defends democracy. And accurately reporting misdeeds can empower citizens to vote for change.
In Newmark's eyes, protecting freedom of the press is also tantamount to protecting the country. Classified ads don't keep him up at night. Thinking about corrupt reporting practices does.
Here's what else gnaws away at him: hybrid outlets. As Newmark describes them, these new sources have a legitimate reporting arm as well as — in Newmark's words — a "disinformation operation." He doesn't name the offending outlets. When asked, he says his news reading spans the spectrum of viewpoints, as long as the sources are known for rigorous fact-checking.
Newmark doesn't discuss his political affiliation. In fact, he outright avoids coming down on a side in today's sharp political divides. However, he has donated modest sums to Democratic causes and candidates, including California senator and presidential candidate Kamala Harris ($3,000 since March), freshman New York congresswoman Alexandria Ocasio-Cortez and recurring contributions to ActBlue, a nonprofit that helps Democratic candidates raise funds for elections.
"I work with a lot of veterans groups. And, you know, they tell me that previous wars were not my fight. Because, nerd. But they tell me now that countering disinformation, information warfare, that's my fight. Because, nerd," Newmark says. To him, amplifying a lie by repeating it is one of the worst things an organization can do.
"A trustworthy press is the immune system of democracy," Newmark says, not for the first time. "Our country only survives with a trustworthy and vigorous press."
It's been 19 years since Craigslist's founder steered the ship, but the site remains Newmark's biggest accomplishment to date.
The company retains its anti-corporate mission that deprioritizes profits, a considerable feat given today's laser focus on maximizing revenue from online advertisers or sales. Early websites heralded the information age. Today, the internet is a profit engine for many big businesses.
Craigslist made Newmark a wealthy man, but it's his post-Craigslist legacy that's near and dear to his heart. By turning his riches into endowments, Newmark hopes to change the world.
His personal mottos and even the subject of his Twitter feed are all carefully curated to focus attention back to the projects he cares about most. Newmark rarely puts forth his own statements, preferring to share stories to his more than 80,000 Twitter followers about organizations helped by Craig Newmark Philanthropies, from school donations and veterans to stories that whiff at his political leanings.
Newmark is looking ahead.
"I guess in the future, I'd like to be known for doing some things well that helped people do a lot of great things for the entire species, the entire planet," Newmark says. "Craigslist helps you get through the day. But some of the work that I'm doing philanthropically helps the entire country, and possibly helps the entire species, move forward. That matters."
Mr. and Mrs. Levin, Newmark's childhood Sunday school teachers, would be proud.