Available June 9, 2026

The captivating story of San Francisco’s meteoric transformation into a global capital of technology, and how the same creative and political forces that gave rise to its boom nearly engineered its collapse.

Excerpt from Chapter 2: The Motor City of the Internet

Mark Pincus, a wiry and gregarious entrepreneur from Chicago, would have much better luck. He’d moved to San Francisco in 1995 after get-ting an MBA at Harvard and working for cable television kingpin John Malone, convinced that the city was destined to be the “Motor City” of the incipient Internet revolution. Together with another young entrepreneur, Sunil Paul, he’d built a product where customers could pick websites and topics of interest to them, and the software would download the con-tent automatically, to be read anytime.

The dot-com boom hadn’t quite started yet. “We would literally sit in coffee shops in the Mission and talk about tech and no one would under-stand what we were talking about, no one,” Pincus recalled later. “There’d just be people with weird ear piercings and tattoos. I loved it. It was such a different culture. I really believed that San Francisco was the melting pot, the germination dish, the only place in the world that we were going to connect the dots and invent this intersection of tech and creative culture.” The company rented an office in the Hamm’s building, on the edge of SoMa. “It was really important to me to be a company in San Francisco, to be a part of this shining light that was really a myth in my head.”

His timing was excellent: he and Paul sold the company, called Free-loader, after just seven months to a dot-com that had already gone public, and Pincus had his first fortune—$5 million. He rented the most expensive apartment he could find, a $3,500-a-month town house on Geary Street, and shortly thereafter bought a house in Cole Valley, near the Haight, for about $300,000. Prices were starting to rise, but the city still wasn’t terribly expensive.

The 1997 pause in enthusiasm for all things Internet turned out to be very brief. eBay, the online auction company founded by another General Magic alumni, Pierre Omidyar, was starting to show the unique power of what would come to be called Internet platforms. eBay didn’t sell anything, but instead provided infrastructure for others to use for their merchandising, and tried to make it fun. The site would first catch on among people obsessed with obscure collectibles—the company’s official founding story, though not entirely true, was about Pez dispensers—and it wasn’t taken very seriously in its early days. For one thing, it relied on trust among strangers, which might be fine for low-stakes hobbyists, but seemed questionable for mainstream commerce. Would the person on the other end really deliver the vintage jacket, or rare book, or crate of kitchen-ware you’d paid for?

Yes, it turned out, much more reliably than one might have expected. The approach could be used for many things, and venture capitalists soon noticed its promise as large numbers of people began building businesses and followings on eBay. Even in the context of buying and selling, there was something to this idea of an online community rooted in trust among people who didn’t know each other. eBay showed it could be a big business. A young programmer from New Jersey named Craig Newmark would show that it could be something different: a mostly free public service operated for the benefit of its users.

Newmark was already steeped in the Internet by the time he moved to San Francisco in 1993 for a job at Charles Schwab, and he found him-self spending a lot of his time there trying to convince his colleagues in the computer department that the Web was the future. He was on The WELL, and though he was shy and socially awkward, he wanted to meet people, partly because folks on The WELL had been very helpful in giving him tips about moving to San Francisco. He attended some of the virtual community’s real-world parties at the funky and low-brow Sausalito Yacht Club, where he got connected to a group exploring virtual reality that met regularly at the Exploratorium science museum. He was tipped to an AnonSalon event that featured a photo exhibit of a fledgling happen-invited to Joe’s Digital Diner, another upstart on the new media circuit, which featured inventive multimedia storytelling and a spaghetti meal. The virtual reality pioneers clustered around Anon Salon were particularly inspiring: “They were about twenty-five years ahead of their time,” Newmark said later.

Newmark was grateful to be part of the action, and he wanted to chip in somehow. “I started telling people about stuff I heard about, either arts or technology or a combination. Then I started a mailing list on my WELL account, I would just email people and ask if they’d heard of something. I started with maybe ten to twelve people, and then more wanted to join.” By the middle of 1995, with tech and culture events happening all over town, the list had outgrown The WELL, and Newmark needed proper software and telecom connections to send it as an email. He also needed to give it a name. He’d been planning to call it San Francisco Events, but then he learned that the people who were receiving it had already decided on an even simpler moniker.

They just called it Craig’s List.

Information about social gatherings and technology happenings was always in demand, but Newmark said later that it was the challenges of San Francisco’s rental apartment market that led to Craigslist’s surge in popu-larity toward the end of 1995. “We started to see an apartment shortage here, and I told people that if they see any for-rent signs, they should send them to me,” he recounted. Signs on buildings were the primary means of advertising San Francisco apartments in those days, so looking for a place meant walking or biking or driving the streets. It was so much handier to get the information in an email. By the next year, there’d be a website too, kindly supported by a friend who had a high-speed line.

Newmark had just a few basic principles, all based on empathy for the person staring at the screen. He’d become perhaps the only Internet entrepreneur in history to build a substantial and lucrative business on the most commonplace of observations about human nature. People don’t like change. Also, free is good. And keep it simple, with minimal rules. It would work extraordinarily well for a very long time.

Cindy Cohn, a young lawyer from Michigan, had been in San Francisco for a few years, living in the Haight, when she and her roommate, who’d gotten to know a crowd of hackers, decided to throw a party. Among the guests was John Gilmore, and Cohn soon fell in with a group of libertarian techies, dating one of them and becoming good friends with Gilmore, while learning about the novel legal and political issues that were starting to churn around the Internet. A couple of years later, Gilmore would call with a request: would she be interested in working with the Electronic Frontier Foundation and representing a man named Dan Bernstein, who wanted to challenge US government rules banning the export of encryption software. “I thought my boyfriend would think I was cool if I did it, so I said yes,” she joked later. (She then fretted about whether her long-ago paramour would mind the reference. “They’re privacy people! It’s important.”)

The regulations at issue in the case essentially treated encryption tech-nology as if it were a weapon, even though scrambling information so it couldn’t be read without a special key was a common practice—the capa-bility was already embedded in many computers. Treating it like a gun or missile made little sense as a practical matter, and effectively assured that only the government, and not regular citizens, would have access to truly private communications. Bernstein’s was one of several lawsuits against the government that the EFF would take on in its early years, when exist-ing laws often didn’t apply very cleanly to the Internet and a lot of efforts to regulate cyberspace looked hopelessly, insultingly ignorant.

A critical test would come in 1996, when Congress passed a law re-vamping telecom regulations that included a provision called the Com-munications Decency Act, aimed at blocking children from accessing pornography online. The CDA would have made it a crime to enable any-one under eighteen to view “indecent” material, even though that would have amounted to a ban on words and images that were protected by the First Amendment. The young Internet industry, led by the EFF, rose up in protest, with the rallying cry of “Internet freedom” echoing around SoMa. HotWired was a leader of the “Black Thursday” protest where thousands of websites turned their background colors black as a statement against the CDA, and was a plaintiff in the lawsuit led by the EFF and the Ameri-can Civil Liberties Union. Louis Rossetto even had signs printed up for a protest in South Park as employees joined the protests against the CDA. “Hands off our Internet” fit nicely with the local Left’s critique of the capitalist power structure too, though it wasn’t a partisan issue in the conventional sense.

Most of the CDA was indeed found unconstitutional, though one important and controversial bit survived, with the strong support of EFF: Section 230, which said Internet companies were not legally responsible for what third parties post on their platforms. Without that protection, any online service that allowed others to comment or upload content—like PlanetOut, for example, or Craigslist—would face enormous and potentially lethal legal risks. Critics across the political spectrum, including Louis Rossetto, would later attack it for varied reasons, but Section 230 would be a survivor.

The EFF sat in an unusual spot amid the political cross-currents of the city.

While Gilmore, Barlow and some other EFF backers were true libertarians, Cohn notes that many others involved in the cause were not. “Mitch [Kapor] was never a libertarian,” she said later. “He was much more of a more traditional kind of liberal, but there was common cause when all these people were looking at what the government was doing about this new emerging space, and realizing that they didn’t have a clue.” Kapor, for his part, agrees that the EFF in its early years “was really driven by this libertarian impulse, which I did not have, and it was a constant sound of tension.”

The group would prove adept at riding the line, and would grow into a major force in the legal and tech policy world, with Cohn taking over as legal director in 2000, and executive director in 2015.

The liberal-libertarian tension, though, would never go away. The EFF was created in the hope that cyberspace could be free from the heavy hand of the state, an open realm of creativity with minimal rules. Yet its mission would grow even more complicated as powerful companies, rather than governments, started to become a big threat to Internet privacy and free speech. It would also have to reckon constantly with the basic dilemma of human governance: if everyone can do and say whatever they want, people get hurt.

The utopian elements of early Internet culture can be seen as efforts to transcend this tension and create new types of communities built in equal part on freedom and trust. Craigslist and community sites like Planet-Out, and even eBay, were showing how it could be done in a limited way with an online service. The adventurers at the San Francisco Cacophony Society would show how a libertarian-themed compact could operate in the physical world. SoMa’s new creative class was now conjuring a fantasy twin on a barren salt flat six hours away, one that would suffuse the culture of San Francisco and its tech community, and stand as a metaphor for the city’s wonders, and also its woes.

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