Building Connections with Code

craigslist founder Craig Newmark demonstrates that tech thrives best when built on human connections

photo: Bleacher + Everard

By Anne-Frances Hutchinson

Commitment is Craig Newmark’s comfort zone, and as the founder of craigslist, it became a way of life. “My perspective is that of a software engineer and customer service rep, and that’s a rare combination. I may be the only one as far as I know.” As the visionary behind one of the most iconic platforms of the early digital age, Newmark didn’t just build craigslist into a household name; he made exceptional customer service its cornerstone. Twenty years ago, he walked out of the C-suite of the company he founded to immerse himself in customer service, where he spent 15 years directly assisting users.

What made craigslist so remarkable wasn’t just its simple, no-frills design or the fact that it became a global household name. It was the profound commitment to connecting people and providing a platform driven by user needs rather than profit. craigslist is a prime example of how a business can thrive by focusing on what truly matters: providing a reliable, trustworthy service that consistently puts its community first. Newmark’s dedication to fostering genuine human connections set craigslist apart as a unique, grassroots success story in the infancy of the internet. What’s truly impressive about craigslist is its authenticity, a tech giant built on the principle of service, where the value lies in connecting people, not in exploiting them.

This rare blend of software engineer and customer service expert is what truly sets Newmark apart, and it’s a path that has left an indelible mark on his legacy.

It’s a fair bet he’s one of the rare Internet Hall of Famers to have taken that path. As craigslist celebrates 30 years of connecting people to what they want or need, Newmark’s passion for customer service – and serving others – burns brightly as ever.

Craig Newmark in high school, 1970
Photo Credit: Peter Vidor

“I’m not only honest, but I’m an engineer, and engineers are notoriously bad at dealing with someone who lies for a living.”

“We need to see genuine commitment to customer service and need to repeat that,” he told us recently. AI is central to his vision of automated customer service that rises to the upper limits of its potential. “I assume a company is genuinely dedicated to customer service. Let’s assume that they’re not just giving lip service and not just going through the motions. That means that they already have a number of people who are good at listening to customers and then suggesting good responses.”

If the company is serious about going all in on customer experience, they can begin to train an AI large language model on high-quality help that allows customers to use the chat system to get answers out of existing written material.

“In addition, when customer service reps get contacted because the help pages or FAQs don’t answer the question, after they’re done answering they can add that Q&A to the existing help pages, et cetera, which means the large model is trained on new questions.” Because the updated Q&A is in the database in a large language model, customer service reps are always ready to answer another question from a customer who needs help on an issue that’s not yet in the large language model.

Craig Newmark in high school, 1970. Photo Credit: Peter Vidor

“But,” Newmark cautioned, “I am assuming a genuine commitment to customer service.”

What happens when a chat system is stumped? “It should call for a person.” he said. “Companies providing AI tools need to recognize that their large language models must learn when to call for human help.” Chat systems need to know when they’re over their heads so to speak and ask for help. Otherwise, the models may “hallucinate” and make up an answer out of thin air.

“That’s problematic because when you’re seeking critical help, whether for yourself or for a loved one, you want a human involved,” he stated. “If a large language model is asked about historical references, the stakes probably aren’t very high. But if it’s providing medical advice, the risks are much higher, and a human needs to intervene quickly.”

Technology may be rapidly transforming the world, but the principle of “garbage in, garbage out” remains constant. No matter how advanced the tools become, if the data fed into these systems is flawed or inaccurate, the results will inevitably reflect those deficiencies. In other words, even the most sophisticated technology is only as good as the quality of the information it processes. This enduring truth serves as a reminder that human oversight, quality control, and thoughtful input are critical to ensuring technology delivers valuable, reliable outcomes.

“You have to be aware that a badly trained large language model can mislead people in a way that contradicts the principle of treating others as you’d like to be treated,” he said. “Additionally, there may also be liability concerns, so it’s crucial that we aim for genuine customer service, which includes making a good faith effort to provide accurate and reliable responses.”

Early roots, lifetime lessons

Craig and Eileen Newmark supporting veterans and military families at Bob Woodruff Foundation’s Stand Up For Heroes event,
2018. Photo credit: Stefan Radtke

Words that are repeatedly threaded through our conversation offer a glimpse of where the pioneering 72-year-old’s head is at these days: respect, honesty, commitment – where it’s always been. “The real answer goes back to what I learned in Sunday School,” he said. His teachers, Mr. and Mrs. Levin, a pair of Holocaust survivors, were some of his earliest and most fundamental influencers. “They taught me to treat people like I wanted to be treated. That was a big part of my moral compass and includes things like knowing when enough is enough. I internalized that; it stuck with me.”

In 2015, he created Craig Newmark Philanthropies (CNP), a private non-profit foundation dedicated to keeping American democracy and cybersecurity strong. Cyber civil defense, nonpartisan journalistic integrity, women in technology, caring for military veterans and their families, and voter protection are a few of his interests. “Over the past 10 years I’ve identified some areas of focus that I know something about and can provide meaningful help that regular foundations may not be good at.”

Since 2022 CNP has invested in Black Girls Hack, Girls Who Code, the Girl Scouts, VetsinTech, the Consortium of Cyberclinics, the Ransomware Task Force, and Shadowserver. CNP also pledged $100 million to create a Cyber Civil Defense network of groups committed to preventing threats to the nation’s critical infrastructure. Citizen cyber education and literacy, cyber tool development, and cybersecurity workforce programs to boost diversity are the center of their mission.

CNP’s latest initiative is Take9, a public service campaign that urges everyone to pause for 9 seconds to think before clicking, downloading, or sharing online information. In partnering with a coalition of the nation’s top cybersecurity organizations, Take9 aims to enhance citizen cyber education, develop cutting-edge cyber tools, and advance workforce programs to safeguard our communities and nation.

“Online threats against our country need everyone to help out, everyone to play their role, like in WW2,” he wrote in a recent blog post. “This means networks of networks of people who can seriously help everyone protect themselves, their families, their jobs, and the country. You’re the networks of networks.”

CNP’s approach to guarding against cyberattacks on infrastructure includes assembling people who can help infrastructure providers who aren’t big enough or funded enough to prepare themselves. “The deal is that water control valves, electrical stations, telecom, hospitals, right now they run the infrastructure with so-called program controllers which are basically computers that can operate valves and stuff like that. Right now, a lot of the smaller providers haven’t done anything in terms of security, and they need some help.”

Despite the dangerous reality, Newmark is calm. “We want to remind everyone if they do need help, we try to provide that help in a reasonable and respectful way. We don’t want to panic people. We’re just trying to tell them that there’s a big problem and help is coming.”

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I’m an old-school nerd helping to protect the people who protect our country.

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