The most radical thing you can do in Silicon Valley is know when enough is enough. Craig Newmark chose human dignity over extraction, and built a thirty-year proof that surveillance capitalism was always a choice, not an inevitability.
The most radical thing you can do in Silicon Valley is know when enough is enough. Craig Newmark did exactly that, and in the process built one of the internet’s most enduring monuments to human dignity—a platform that proved you could serve millions, make money, and never once treat people like products to be mined.
I’ve spent 32 years deep in the trenches of what we used to call the “information superhighway”—back when that term meant something real, not corporate sanitized. From phone phreaking and running multi-line BBS systems in the #2600 days, through the payment systems wars processing millions for ClickBank’s high-risk merchants, to building fraud detection alongside hackers and former NSA folks in the shadowy corners where security research happens. I’ve been in places most people wouldn’t touch, worked with people most companies won’t name, and witnessed firsthand how the web evolved from a community of people helping each other into a surveillance machine designed to extract every drop of value from human attention.
That’s why Craig and Craigslist hit different. Because I know exactly how rare and precious what they built actually is.
In 1999, venture capitalists and bankers lined up to tell Craig Newmark he should “do the usual thing” and “monetize everything.” They promised billions. Recent estimates suggest he walked away from roughly $11 billion in potential wealth. His response? “I don’t need $11 billion, but I do want to make some money.”
Craig’s moral compass was set by Mr. and Mrs. Levin, Holocaust survivors who taught his Sunday school. Their lessons were simple: treat people like you want to be treated, and know when enough is enough. Most people hear those lessons. Craig actually lived them, encoding them into every line of Craigslist’s DNA.
“I’m a nerd. I’m a rule follower,” Craig explained decades later. “That was pretty much made part of my core moral compass. And without thinking about it, I just followed through.”
While the rest of Silicon Valley was discovering that surveillance capitalism could turn users into the most profitable product ever invented, Craig was doing customer service. Not as a temporary startup phase, but as his permanent job. The founder of one of the web’s most-visited sites spent his days responding to flagged posts and scam reports because it kept him “in touch with what’s real.”
Here’s what Craigslist never did—and this list reads like an indictment of everything the modern web became:
No tracking. No cookies, no beacons, no behavioral profiling, no data sharing. Their privacy policy is so clean it shocked Digital Trends: “easily the best privacy policy we’ve seen.”
No algorithms. Posts appear chronologically. No machine learning to maximize engagement. No recommendation engines to keep you scrolling. No attempt to manipulate what you see based on what you clicked yesterday.
No advertising. Craig called banner ads “kind of dumb” because “they slow the site down.” So he just… didn’t run them. In 1997, when Microsoft Sidewalk wanted to pay market rates that would cover all his expenses, he said no. “I’m an overpaid programmer, I don’t need the money.”
No growth hacking. The site never marketed itself. Zero ad spend. Pure word-of-mouth. When they tried a couple ads around 2000, Craig decided it “didn’t feel right” and stopped.
No feature creep. The interface looks essentially identical to 1996. Not because they’re lazy—because users consistently told them “they didn’t want fancy stuff; they wanted something simple, straightforward, and fast.”
No maximizing time-on-site. The entire design philosophy is the opposite: help people find what they need and get out. “We’re finding that pretty much everyone out there shares, more or less, the same moral compass as we do,” Craig observed. “People are good.”
No exploitation of “enough.” When you’ve got 50 billion monthly page views and one of the web’s most loyal user bases, conventional Silicon Valley wisdom screams to monetize everything. Craigslist charges $25-75 for job postings (newspapers charged $150+), small fees for apartments in high-demand cities, and leaves everything else free. Total team size: 40-50 people. Estimated profit margins: 75-85%.
The platform that venture capitalists said would be “unbundled” by specialized competitors watched those competitors become the most enshittified companies on the internet—surge pricing, algorithmic manipulation, declining service quality. “But enshittification never came for Craigslist,” as one analysis noted, “because it chose never to allow itself to reach beyond its original goals.”
I remember the early web. I was there before the web existed, running multi-line BBS systems where community was built through text and trust, not surveillance and engagement metrics. The #2600 culture—phone phreaks sharing knowledge, building tools, helping each other navigate systems—that was the DNA of the early internet. Craig came from that same world. He understood what we all knew then: the whole point was connection and utility, not extraction and exploitation.
I watched the evolution from Finger protocols and .plan files through Gopher and IRC to the modern web, and I saw the exact moment when the paradigm shifted.
Pre-2000s: The internet was people helping people. Information sharing. Community building. The whole point was connection and utility.
Post-2004: Google’s IPO proved that “behavioral surplus”—data collected ostensibly for service improvement—could be repurposed into the most lucrative advertising targeting system ever built. Their revenue increased 3,590% through what Shoshana Zuboff would later call “surveillance capitalism.”
Craig was there for both eras. He started Craigslist in 1995 as an email list to give back to the San Francisco community that had helped him as a newcomer. When friends told him they were calling it “Craig’s List,” he didn’t even know what a brand was. “They explained what a brand was,” he recalls with characteristic nerd literalness.
The crucial decision came in 1999. That’s when Craig “decided to keep the site almost all free and to walk away from the money bankers and VCs told me was on the table.” He describes this not as altruism but as practical application of Sunday school lessons: “You should treat people like you want to be treated. You should know when enough is enough.”
What Craig understood—what I learned in my years building payment systems that processed millions daily, catching fraud, protecting merchants and customers in the wild west of online commerce—is that there’s a fundamental choice in how you build systems: serve users or extract from them. The surveillance capitalism model chose extraction. Craig chose service.
As he put it bluntly: “Since we’re not advertising supported, we have no need to artificially create engagement… Often, the algorithms on some social media sites, they are focused on driving engagement even if they’re engaging with people who are lying to them, if they’re trying to radicalize them.”
Scholar Jessa Lingel called Craigslist “the internet ungentrified” in her book An Internet for the People. It’s a perfect description. Craigslist represents Web 1.0 values—technological simplicity, collectivism, locality, anonymity, serendipity, and democracy—that refused to die when the rest of the web gentrified into corporate surveillance platforms.
The contrast is stark. Facebook’s Marketplace has 800 million users versus Craigslist’s 55 million. But that 800 million comes at the cost of:
Craigslist’s 55 million users get:
“We have a really good culture of trust on the site—of goodwill,” Craig explained. “This is kind of democracy in real life. Everyone wins, except for the bad guys.”
I’ve worked places you’ve never heard of, processing transactions for industries people don’t talk about in polite company. I’ve built fraud detection systems that became $640 million acquisitions. I’ve created hardware with military-grade encryption and patents for payment security—like PayThatWay, a universal Bluetooth payment system I built in 2009-2011 that worked with any phone, no apps required. Years before Square made mobile payments mainstream, I had working hardware. But I was focused on solving the technical problem elegantly rather than optimizing for maximum market extraction.
Sound familiar?
I’ve been shoulder-deep in the actual infrastructure that makes the modern web work—not the sanitized startup story version, but the real systems where money moves, bad actors attack, and security either holds or breaks. I’ve processed millions for high-risk merchants, seen every scam, every exploit, every dark pattern. I know exactly what’s possible when you prioritize extraction over service.
From that perspective, Craig’s accomplishment is even more remarkable. It would have been trivially easy to rationalize adding “just a little” tracking. Just some basic user profiling. Just some engagement optimization. Every other platform did. The money was astronomical. The pressure was constant.
Craig said no. For thirty years. Through the dot-com boom, the Web 2.0 explosion, the mobile revolution, the AI transformation. The answer stayed the same: treat people like you want to be treated, know when enough is enough.
This isn’t naivete. Craig worked in customer service, dealing directly with scams, fraud, and the worst of human behavior online. He knew exactly what the platform enabled, good and bad. But his response wasn’t to build surveillance infrastructure—it was to empower community self-policing and trust users to be basically decent.
“What surprises me, in a way, is how almost universally people are trustworthy and good,” Craig reflected. “There are some bad guys out there, but they are a very tiny minority.”
I created dignity.ink because I believe the same thing Craig proved: we can build better technology that serves human dignity instead of extracting value from every interaction. When Google’s platform dependency left my entire house unusable because they decided I “didn’t exist,” when I watched my Gmail dependency become a single point of catastrophic failure, when I traced how every photo uploaded trains AI systems we have zero control over—I realized we’re at the same crossroads Craig faced in 1999.
The AI era makes these questions survival-critical. Without digital sovereignty, you’re up creek without a paddle in an AI world. Every day your data trains systems you can’t control. Every platform dependency creates catastrophic failure points. Every surveillance-based business model teaches AI to optimize for extraction, not service.
But with sovereignty? You’re not just surviving—you’re thriving with AI that serves you.
The climate crisis didn’t make us give up electricity. We innovated to solar, wind, and batteries. The AI crisis needs the same energy: don’t abandon technology, build BETTER technology. The best solutions emerge from pressure. AI forces us to finally solve problems we’ve been avoiding for decades—surveillance capitalism, data ownership, platform dependency.
Craig showed it’s possible. Craigslist proves alternative economics work. Massive scale without surveillance. Profitability without exploitation. User-centric design that succeeds. “Enough” as a viable business strategy. Values that persist despite competitive pressure.
Craig’s philosophy comes down to a few interlocking principles:
Treating people with dignity and respect. Not as engagement metrics or behavioral data points or attention inventory to be sold. As people trying to accomplish basic human tasks—finding housing, getting jobs, buying furniture, connecting with their communities.
Knowing when enough is enough. Once you can live comfortably and help friends and family, it feels a lot better to make a difference than to maximize wealth. “Nobody needs a billion dollars.”
Trust in human goodness. “People are good. There are some bad guys out there, but they are a very tiny minority and our community is self-policing.”
Simplicity and functionality over fancy design. “I didn’t know how to do fancy… People consistently told us they didn’t want fancy stuff; they wanted something simple, straightforward, and fast.”
Community service over profit maximization. “Craigslist helped and helps the average citizen get food on his table, get a table, and find a roof to put the table under. That’s not philanthropy, it’s public service.”
Staying connected to users. Doing customer service “as long as I live” because “engaging with the people you’re serving tends to rejuvenate that compass.”
I’ve spent over three decades working with the same people—Dax since 2003 (the guy who casually mentioned that encryption algorithm I needed was “just prime numbers” he’d been working on since middle school), Paul Unger for 24 years building sustainable businesses, mentors and collaborators who understood that long-term relationships matter more than transactional wins. That’s not common in tech. But it’s common with people who share Craig’s values.
Craig’s approach wasn’t ignorance or innocence. It was deliberate, disciplined resistance to the easier, more profitable path. It was choosing to encode values into systems architecture. It was proving that the shift from Web 1.0 openness to Web 2.0 exploitation wasn’t an inevitable technical evolution—it was a choice.
That choice is in front of us again with AI. We can build systems that extract and manipulate, or we can build systems that serve and empower. We can optimize for maximum monetization, or we can decide when enough is enough. We can treat users as products, or we can treat them like we want to be treated.
Craig chose service over extraction. Enough over everything. People over products. Community over surveillance.
Thirty years later, Craigslist still stands—unchanged, principled, profitable, and human.
That’s not just a business success story. That’s proof that another way was always possible. That moral compasses can guide technical decisions. That knowing when enough is enough is the most disruptive innovation of all.
In a world racing toward AI-everything, platform-everything, surveillance-everything, Craig Newmark showed us the most radical path: treat people like human beings, build tools that serve them, and refuse to compromise when everyone tells you that’s leaving money on the table.
I’m building dignity.ink in that spirit. To prove it’s still possible. To show that AI can serve humans instead of extracting from them. To demonstrate that digital sovereignty isn’t paranoid—it’s about having choices.
Craig didn’t just build a classified ads site. He built a thirty-year proof of concept that the entire modern web architecture is a choice, not an inevitability.
For someone who’s been deep in the technical underground since before the web existed, who’s built systems in the shadows that most people never see, who understands exactly how rare it is to maintain principles under that kind of pressure—Craig Newmark is exactly the kind of hero we need to remember.
Not because he was perfect. Craigslist has problems, struggles with fraud, contributed to newspaper industry decline. But because he showed that treating people with dignity and respect isn’t just moral—it’s sustainable, profitable, and technically superior to the surveillance capitalism model that consumed everything else.
When I learned those Sunday school lessons from Mr. and Mrs. Levin through Craig’s example, I didn’t just learn about classifieds. I learned that the most important technical decision is ethical, not architectural.
Know when enough is enough. Treat people like you want to be treated. Build systems that serve.
The rest is just implementation details.
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