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At a cheap card table in a South Market loft, Craig Newmark sat with friend and fellow web enthusiast Anthony Batt, mulling over what to call his newest web venture. It was the 1990s in San Francisco, when rent was affordable and the internet relatively new. Newmark, a round-faced software engineer, had just launched an email list that alerted his friends to local events in the city. In keeping with his tendency to take things literally, he floated San Francisco Events as a top contender for its name.

Batt was getting impatient; the list already had an unofficial name used by its recipients. Just call it Craigslist, he told his friend. And so it was.

Nearly three decades later, the mailing list has morphed into one of the most popular classified advertisement websites in the U.S., with a presence in more than 70 countries. Despite making a killing off its success, Newmark refused to monetize the site except through a handful of minimal revenue streams. He still retains a sense of frugality unique among his fellow tech entrepreneursbesides multiple streaming service subscriptions and a modest collection of Simpsons figurines, his largest luxuries include hiring a plant sitter when hes out of town.

A self-described nerd, Newmark has the requisite thick-rimmed glasses and affinity for science fiction. But the Craigslist founder is more likely to be found discussing the ideals of democracy than toying with Perl. Hes explored a varied range of political philosophies, ethical frameworks and social codes over the years, but his passions have stayed centered on how to safeguard the U.S. and its citizens against misinformation and harassment. Since retiring from Craigslist in 2018, he has become a crusader for cybersecurity protections, trustworthy journalism and veteran support.

Now, at 70, hes preparing for his next stage in life by giving away his sizable fortune. His donations to date havent been insignificant by any means. But its time to get serious, according to Newmark. My big mission, simply stated, is to help and protect the people who help and protect our country, he told Observer.

Newmarks initial interest in philosophical concepts was shaped during his childhood in Morristown, New Jersey, where he grew up in a lower middle-class Jewish household. His mother was a housekeeper. His father, an unsuccessful salesman of both meat and later insurance, died of lung cancer shortly after Newmark turned 13. I may have had a normal childhood with friends until my fathers death, said Newmark, who only recently considered how that loss may have catalyzed subsequent social dysfunction.

He grew isolated, getting into fights with other children in middle school, and was labeled a troubled child. Sent to the school psychiatrist, Newmark endured a series of ineffective talking sessions, failed attempts to interest the sixth grader in birdwatching and chess, and a marginally successful trip to Newark Airport in his counselors VW Bug to watch jets take off.

It didnt help that he was resolutely nerdyhe wore pocket protectors unironically and was a member of the debate team. And Newmark wasnt afraid to be pedantic. He called jocks Neanderthals and once attempted to report a gym teacher for abuse after being ordered to run laps, according to Mark Hashizume, a classmate at Morristown High School. Newmarks slight intellectual arrogance during this time was likely a sort of defensive mechanism, according to his old friend.

Newmark and Hashizume became fascinated by Ayn Rand and Objectivism, joining a school group the latter jokingly called The Selfish Cluba reference to the theory of selfish rationalism. With copies of Rands pamphlets and subscriptions to the libertarian Reason magazine, we would just hang out in the classroom and talk about philosophy and exchange ideas, Hashizume told Observer. Newmark once made a pilgrimage to the city to meet Murray Rothbard, a protege and eventual opponent of Rands. But the dalliance with libertarianism didnt last too long. Contact with the real world in any form has a tendency to get rid of delusions, said Newmark.

Something that stuck with him, however, were his Sunday school lessons. To this day, Newmark refers to the teachings of Mr. and Mrs. Levin, a Lithuanian couple who survived the Holocaust, as his ethical guidepost. Their mantras of treat people like you want to be treated and know when enough is enough were reinforced by the lyrics of Leonard Cohen, who Newmark came across in 1988 when he found a recording of Various Positions. That tape is a big part of the liturgy that affects me, he said.

After graduating from Case Western Reserve University, he worked for IBM as a programmer in Boca Raton, Detroit and Pittsburgh for 17 years. Newmark was still dealing with social challenges, often told by colleagues to pick his battles more carefully. I would correct people if they made relatively minor technical mistakes, and sometimes I would correct them in front of others, he said. His favorite manager told Newmark his sense of humor was his only saving grace and that he had a lot of room to grow. He was right, said Newmark, adding that he now realizes he lacked a basic understanding of social etiquette.

In the early 90s, Newmark left IBM behind for a position with Charles Schwab in San Francisco and found himself immersed in a community connected by the early roots of the Internet. It was a relatively nascent concept and one ripe with possibilities. Craig and I were both really excited to be at this birthplace of the web, said Batt, who met Newmark on The Well, one of the earliest online message boards, where the two bonded over their excitement for the newly invented World Wide Web.

At the time, computer enthusiasts were a small community, one that was optimistic about how technology could change society, Batt told Observer. He and Newmark attended get-togethers in Victorian apartments across San Francisco, parties where people gathered around computers to look at web pages and discuss articles from the recently launched Wired magazine. Excitement over the unexplored possibilities took on an almost religious fervor. We were evangelizing the web in a way that was earnest, said Batt. People approached the emerging digital domain with an emphasis on tikkun olam, according to Newmark, referring to a Hebrew term that translates to repairing the world.

Newmark also attended the Berkeley Cybersalon, a monthly gathering started by media consultant Sylvia Paull. More than 100 people would cram into Paulls house to discuss the impact technology had on some aspect of our society, whether it was education, music, literacy, security, she told Observer. Paull described Newmark as a straightforward personality who uses humor to soothe otherwise blunt remarks. If he sees a contradiction or someone aggrandizing their accomplishments, hell undercut what they say in a witty way, she said, to make them laugh, while realizing theyre showing off or falsifying something.

Newmark initially created Craiglist to aid friends in San Francisco looking for events, places to stay or available jobs. He was adding new people to the list constantly. He was just so friggin diligent, said Batt. It grew in popularity, and the listserv became a website in 1996. By the end of the following year, the website was getting around one million page views per month.

Fans of the site urged Newmark to stop running it with volunteers and turn it into a real company. I would go to events and VCs and bankers wanted to throw billions at me if I would do the usual Silicon Valley thing and monetize heavily, said Newmark. But he decided to monetize minimally, charging for a select portion of posts like job openings and broker apartment advertisements, because making money was his second priority. The first was still making the world a better place. Craigslist onboarded Americans in the tens of millions onto the Internet. Thats a good thing.

Craigslist was officially a private for-profit company in 1999, with Newmark as CEO. But that didnt last long. By the end of the year, people helped me to understand that as a manager, I suck, said Newmark. To do a good job of this stuff, you have to have charisma, or what I understand the kids call rizzIm using that in the broad sense, not the romantic sense, he said. Whatever charisma is, Im kind of charisma negative.

Newmark often self-deprecates in this manner, occasionally with a wry smile. He is very discreet; he doesnt like public attention, said Paull of her longtime friend. She recalled visiting him during Craigslists early days in his shabby office in a house out in the Avenues of San Francisco, where he introduced her to Jim Buckmaster, the computer programmer Newmark hired as CEO in 2000. This is the person who really runs the place, not me. I just handle customer service, he told her.

It wasnt a jokeafter ceding power, Newmark did take a customer service role at Craigslist, which he held for more than a dozen years. I liked the continual sense I was getting that Craigslist mattered, that it helped people with real life, he said of the job. But I saw things that I will never unsee. Hed created one of the worlds most popular websites, where users sold everything from motorcycle parts to cactus plants. However, the site also became a platform for prostitution. In 2010, more than a dozen attorneys general wrote an open letter to the company requesting its adult services section be taken down to prevent instances of sex trafficking. Later that year, the section was permanently closed.

Despite receiving public backlash for its perceived inaction, Craigslist had actually been quietly working on related issues with law enforcement agencies. In 2015, Newmark accepted an award from the FBI for the websites collaboration in preventing human trafficking. It had been offered five years prior, according to Newmark, who said he regrets not accepting it earlier to diffuse misinformation. Lets just say there were some mental health issues. Im still suffering from some traumatic stress, he said. The stress of running something large and public that interacts with thousands of people every day was real.

Craigslist also faced accusations that it played a role in the decline of newspapers by taking away lucrative revenue from traditional classified advertisements. At a 2005 convention for the American Society of Newspaper Editors, panelists displayed a photo of Newmark while discussing the industrys crisis, and he was labeled a newspaper villain as recently as 2018. For years I was waiting for someone to look at the actual numbers, he said, pointing to findings from Danish analyst Thomas Baekdal that suggest websites like Craigslist had no measurable impact on the newspaper industry.

Newmark officially left Craigslist five years ago, but his focus on revolutionizing society has only become more spirited. Through Craig Newmark Philanthropies, he has channeled millions of dollars to organizations working to promote trustworthy journalism, strengthen cyber civil defense and raise up veterans. The company needed my help less and less, and I became progressively useless, he said. I found I could do more, and more good, for people by focusing on philanthropy.

This wasnt a surprise to old friends like Paull, who recalled Newmarks enduring interest in keeping scammers off Craigslist and his longstanding passion for upholding democratic ideals. He could have been a lawyer, hes really a constitutionalist, she said.

Newmarks philanthropic engagement with journalism was largely inspired by lessons he learned in history and civics in high school. I was taught that a trustworthy press is the immune system of democracy, he said. I could see an immune system not working, and I decided I needed to play a role. He reached out to industry leaders like Jeff Jarvis to figure out what that role could look like. Newmark was particularly interested in how to regain public trust and fend off disinformation through good journalism, according to Jarvis, a professor at the City University of New Yorks Graduate School of Journalism. Trust is the new black was one of his lines, he told Observer.

After Jarvis introduced Newmark to the schools then-dean, Sara Bartlett, the Craigslist founder gave the program a $20 million donation. In an homage to Newmarks nerdy roots, the 2018 endowment was celebrated with promotional materials like plastic pocket protectors emblazoned with the schools new name: The Craig Newmark Graduate School of Journalism. Hes since funded numerous media publications like the Markup and the Guardian, in addition to giving multi-million-dollar gifts to the journalism schools at Columbia and Howard University.

On the cybersecurity side, Newmark has kept an eye on the field since the 1970s when he became interested in natural language processing, a branch of artificial intelligence. Ive been paying intermittent attention through the decades, until the point where I finally got seriously involved, he said. In 2017, Newmark began to hear about information related warfare originating from our adversaries overseas in conversations with veterans, journalists and occasionally law enforcement. It took a while, but it finally registered that we were a country at war, and that everyone needed to play a part, maybe in proportion to their ability to help.

Newmark has funded numerous organizations combating ransomware operations and educating civilians in cybersecurity literacy. Its a big deal, because ransomware destabilizes businesses here in the U.S., which is a matter of national security, he said. And beyond that, ransomware gangs, lets say in Russia or North Korea, appear to be a part of the way they attack our country and how they financially support themselves.

Meanwhile, veterans issues have struck a chord with Newmark since high school, when he witnessed returning service members being verbally mistreated. I was completely naive back then about politics, but I could see that this was really unfair, he said. In 2013, he was named a consultant, or nerd-in-residence, at the Department of Veteran Affairs.

Its no coincidence that much of Newmarks giving has a patriotic bent. He evolves to meet the needs of the moment, but all keeping in the through line of citizen security, Vivian Schiller, director of the nonprofit Aspen Institute and Newmarks former philanthropic advisor, told Observer. Newmark, who refers to himself as an Eisenhower baby and a nerd, 1950s style, says he grew up during a time when patriotism was the norm. Now, a lot of people who use that word lets say theres room for improvement. But he still believes in the conceptmost of his philanthropy efforts focus not only on protecting people but specifically American citizens. First, we need to protect the Republic, he said.

The one outlier in Newmarks philanthropy is pigeon rescue, toward which he estimates hes donated upwards of $50,000. He fell in love with the birds back in the 1980s and today regularly places food and water out for local pigeons in the garden of his Manhattan home. A frequent visitor nicknamed Ghost Faced Killer is a regular presence on Newmarks social media profiles. Normally pigeons mate for life and are monogamous, however weve observed Ghost Faced with at least several different ladies, he said, There are a lot of pigeons visiting these days which share some of his distinctive plumage.

Ghost Faced is the favorite of both Newmark and his wife, Eileen Whelpley. The two married in 2012, putting an end to the Craigslist founders difficult, and at times literally painful, dating life. In the 1970s, after taking a ballet and jazz class to meet women, Newmark suffered a hernia, passing out when told hed need surgery.

Despite Newmark being a major philanthropist, the total sum of his fortune has long been shrouded in mystery. Hes never publicly revealed his net worth, which Bloomberg in 2020 estimated at $1.3 billion. I want to keep the focus on giving nearly all my money away to worthy causes, not how much Ive made, said Newmark. I wish everyone who has been as fortunate as I have been would do the same.

Looking at Craigslists finances doesnt offer much clarity, as the privately-owned company doesnt disclose its revenue numbers. But regardless of the exact figure, Newmarks giving makes it clear that his wealth is substantialearlier this year, he pledged $100 million each to both cybersecurity initiatives and veteran support. Theres more to come, according to Newmark, who plans to give away virtually everything hes earned during his lifetime. His next gift might be directed toward the Craig Newmark School of Journalism, which the philanthropist hopes to someday make tuition-free. The more I share power and money, the more effectively I can fulfill my mission, he said.

Reaching personal milestones has also reinvigorated his democratic ideals. Hitting 70 and facing some recent health issues reminded me that I have a limited amount of time to be effective, said Newmark, who recently underwent minor heart surgery. A nerds got to do what a nerds got to do. Normal people arent getting the job done.

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Craig Newmark Retired from Craigslist. Now He Wants to Save ... - Observer