Craig Newmark made his fortune off a website, founded in 1995, that served as an early online bulletin board and looks like it hasn’t been updated in two decades.

That website, Craigslist, is still cranking along, featuring apartment listings, an active jobs board and items for sale. But the privately held company has long been surpassed in value by the likes of Airbnb, LinkedIn and Facebook Marketplace, which all face Wall Street’s demands for growth and profit.

Though Newmark’s internet company may be outdated, his concerns about where the industry is headed are most certainly not. Since the 2015 debut of Craig Newmark Philanthropies, the entrepreneur has donated many millions of dollars to various causes involving media and technology.

Most recently, his organization contributed $3 million to help fund a new artificial intelligence and education initiative from Common Sense Media, the nonprofit told CNBC this week.

“While I tried to pay some attention to what was going on, just everything caught me by surprise,” Newmark said, referring to the current boom of generative AI and all the new and intelligent chatbots.

Newmark, 70, spoke to CNBC as he was recovering from a minor heart procedure he went through in late August. The heart ablation required Newmark to lay on his back “the whole time in the wrong position” and he “woke up with a lot of back pain,” he said.

More than the surgery, Newmark wanted to talk about the hospital food.

“Hospital pudding is really good,” he said. “And since they served my lunch cold, I asked them and got more containers of pudding.”

Newmark, who ran his business out of San Francisco but now lives with his wife in New York, said the hospital stay didn’t cause him to reflect much on mortality, as he’d already addressed such existential issues when he decided to simplify his life by giving away much of his Craigslist riches.

Newmark’s foundation has principally focused on donating to organizations and causes pertaining to journalism, combating misinformation, countering online harassment, cybersecurity issues, and supporting veterans and military families.

The rapid evolution of AI and its potential hazards have recently caught Newmark’s attention, and his money.

The goal of Common Sense’s AI project is to provide an AI ratings system for parents, educators, policymakers and regulators so they can evaluate what makes certain tools like OpenAI’s ChatGPT safe or unsafe for children. Additionally, the nonprofit is offering online AI literacy courses intended to help parents and educators teach basic AI fundamentals to children.

The full scope of AI’s capabilities and potential for societal harm became more clear to Newmark by the time companies began “modifying search engines to use generative AI.”

“I realized that if a search engine was using sources that weren’t reliable, if the sources were about lying to people, that would create a big, ethical problem, and you really don’t want a news source of any sort to knowingly lie,” Newmark said.

Newmark is concerned that bad actors will use generative AI to more easily amplify and spread disinformation. At the same time, he’s worried that tech companies, particularly in social media, “aren’t even trying anymore to get rid of stuff they know is dishonest,” he said.

Tech companies like Meta, Amazon and X (formerly known as Twitter) recently laid off numerous trust and safety workers as part of major cost-cutting initiatives, but have said that the downsizing won’t affect the safety of their platforms.

Meanwhile, AI has the potential to profoundly affect society, like the internet and the printing press before it, Newmark said. That’s an area where he has notable expertise. Craigslist was both hugely disruptive to newspapers and their classified ads sections, and has been a site that’s attracted criminals and scammers.

Few people predicted the “bad uses” of the internet, which has allowed nefarious actors to “mostly lie to people in large numbers,” Newmark said.

“I guess the profits to be made in being a really good professional liar, those profits have greatly increased because the internet is a big amplifier,” Newmark said. “It’s everyone’s printing press, and you get to use it as a printing press, whether your intentions are good or bad.”

Newmark said he became interested in language-generating software like ChatGPT in the early 1970s, “when people were beginning to talk about language understanding and neural networks.” However, he says, “I didn’t really understand it.”

Now the technology is here and spreading rapidly.

Newmark said he doesn’t want to name names when it comes to the organizations he fears are creating the most societal discontent through AI, because he’s previously been scarred for getting that specific.

“In the past when I’ve pointed out major problems, I’ve learned the hard way that I’m no match for someone who lies for a living,” Newmark said. “So, I’m allowing myself to be chickens—.”

Rather, he said he relies on “people who are both braver and smarter” to call public attention to those matters.

“Protecting kids when it comes to AI is a big issue,” Newmark said, regarding his donation to Common Sense Media. “I have no idea how I would go about getting started, but I know where to put my money where my mouth is.”

Why Common Sense?

“A lot of groups and politicians talk about protecting kids,” Newmark said. “But these guys are the real deal, and so I’m helping them.”

Newmark acknowledged that the topics of misinformation, journalism and content moderation have become more polarized and politicized of late. House Judiciary Chair Jim Jordan, R-Ohio, alleged that tech companies unfairly censor conservative speech, and he’s undertaken a “censorship investigation” to probe suspected ties between the executive branch and certain technologists and researchers.

Several academics previously told CNBC that the politicized landscape has led to some organizations cutting back on funding research into combating misinformation for fear of being publicly criticized.  

“Some people are backing off, some people are getting braver. Again, I’m not very brave,” Newmark said. He highlighted the Knight Foundation and Ford Foundation as organizations that are “doing brave things.”

Within journalism, Newmark’s most high-profile endeavor is the City University of New York’s Craig Newmark Graduate School in Journalism. The program was renamed in 2018 after Newmark endowed the school with a $20 million gift, though he made prior contributions in 2016 and 2017.

He also donated $20 million in 2018 to help fund The Markup, which describes itself as a “nonprofit newsroom that investigates how powerful institutions are using technology to change our society.” That project quickly became controversial after founding Editor-in-Chief Julia Angwin said she’d been fired over email by co-founder and Executive Director Sue Gardner.

Still, Newmark says both the CUNY journalism school and The Markup have been successful, while other efforts “have not been successful, and I’m being discreet about them because I’m still trying to help before I have much sterner talks.”

He pegs his philanthropy success rate at “70% or 80%, which is good, but it’s not 100.”

In terms of where he spends his time online, Newmark said he still posts on X, primarily to promote and highlight the work of teachers. However, he said the site is losing its effectiveness as it leans toward showing people algorithmically recommended posts.

“As a social network, Twitter does seem to be gone,” Newmark said, adding that he’s trying out rivals like Bluesky, Mastodon and Meta’s Threads.

In particular, Newmark said he likes “like the spirit of Mastodon and Bluesky,” which he likened to the early days of the internet when it took a long time for websites to build devoted audiences.

“The audience development is very slow,” Newmark said. “Twitter and everything else grew slowly and the other sites are growing slowly, and yet we are impatient and we want to see network effects now.”

Cybersecurity is another area of focus for Newmark. He pointed to a recent $100 million commitment announced in March to a collection of organizations working on cyber-related issues, like combating the spread of ransomware and creating methods for tech and security companies to share threat information.

He said the total number will probably exceed $100 million, because he’s already “broken through $80 million.”

In June, Newmark’s philanthropy arm also pledged to donate $100 million to multiple organizations supporting veterans and military members, who “sometimes have to choose between decent housing or feeding their families,” Newmark said. He called the treatment of that community “a national security matter.”

“There’s nothing virtuous in that,” Newmark said about his donations, noting that he doesn’t spend his money on “yachts or fast cars.”

“It’s more satisfying to give it away,” Newmark said. “Again, that’s not pious or altruistic. It’s just what I was taught in Sunday school.”

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