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From the valley to the alley

DoubleClick's ad could be seen near the Flatiron building.

The Flatiron building is one of the most instantly recognizable buildings in New York City. Built at the beginning of the 20th century, its unique triangular design sets it apart from other high-rises and skyscrapers. Its architecture is a blend of pragmatic design and deliberate distinctiveness. Throughout the years, the Flatiron building has stood as the site of many social and artistic scenes in New York City.

For a brief time, it was the spiritual center of New York’s web-driven tech scene. If you stood in the shadow of the Flatiron building at any point between 1998 and 2002 and looked straight up, you’d see a large and garish billboard one block up that read “DoubleClick Welcomes You to Silicon Alley.”

DoubleClick's ad could be seen near the Flatiron building.

Silicon Alley had the familiar markings of the commercialization boom of its west coast counterparts, but its proximity to Wall Street and the media industry gave it a different contour and shape. Most Silicon Alley companies were either content-driven editorial websites or webzines—FEED,, Nerve, gURL, Psuedo—or digital agencies thriving in the information age—Razorfish,, Organic Online. “The closest thing Silicon Alley has to an indigenous population, the Early True Believer,” one reporter noted at the time, “aren’t exactly businesspeople or programming geeks – they’re brainy math-and-music types with impressive liberal-arts educations, mostly upper-crust backgrounds, and birthdays in or around 1966.”

Some members of the scene had started out as college roommates, a close-knit circle of friends of friends of friends that powered a wave of new sites on the web. They were bound together by their wild ambition and belief in the promise of the web. “I think this definitely is not a fad, what’s occurring right now,” Razorfish co-founder Jeff Dachis remarked at the time. The web wasn’t simply a new digital space. “This is absolutely real; this is a revolution; we’re packing rifles; and this is going to be something that’s going to change the course of the way the world is functioning.”

The founders of DoubleClick, though an integral part of the Alley, cut against the mold. The company was created by Kevin O’Connor and Dwight Merriman, who had already spent the previous decade in the microcomputing business. That made them a bit older and more experienced than the average Silicon Alley upstart founder plucked straight from graduating college. Their business model—acting as the middleman for ads between publishers and advertisers—was also a bit more straightforward and pragmatic than the usual dot-com. But DoubleClick did more than almost any other New York based dot-com to change the face of commercialization on the web.

It all started with cookies, which Merriman had been experimenting since they were first added to Netscape. Cookies store small bits of data in a package that can be stored and then retrieved across pages, even when the browser reloads. For shopping carts and personalized experiences necessary on the web, they gave developers a chance to keep track of a user’s order or preferences from anywhere on their site. However, for security reasons, cookies are scoped to a single domain. One website can’t access the cookies of another.

Working out of a basement after-hours at their day job at a Cincinnati based microcomputing firm, Merriman and O’Conner discovered that it was possible to keep cookies stored on a common external domain and then follow its trail of data from one site to the next. By shifting the source of the cookies to a single domain under their control, in this case the DoubleClick servers, data between sites could be aggregated and distributed, as long as each site agreed to install a snippet of code that gave DoubleClick partial access to their data. Merriman used this workaround to create a network of ads that could added, and then tracked, across websites, providing greater leverage and value to the ad buyer and far more probing insight to the ad seller.

By the time they reached New York—and brought on former media executive Kevin Ryan as their CFO—that technology was able to operate all on its own. Companies could buy and sell ads through online auctions conducted by the platform which served them across sites in real time, often without the publishers of the ads even fully understanding what might appear on their sites.

DoubleClick gave Silicon Alley, and the network of startups across the country and world, a suddenly relevant business model. The experiments of early content sites like Hotwired and Word selling individual packages of ads to established partners could only go so far. DoubleClick scaffolded up an advertising command center, where ads could be bought and sold programmatically and at a massive scale. Before long if you stopped a dot-com founder on the street and asked them their business model, they’d reply, simply, “advertising.”

It also spawned an open secret common in all Internet companies, but especially true in New York. Companies were flush with cash from wave after wave of seed investment. So naturally, they had plenty of money to buy ads, usually in other Internet companies. Startups bought ads and published them on the sites of other startups. Doing so infalted everyon’es value.

Most startups used advertising to pass money around between startups rather than out into the larger world. Doing so inflated everyone’s value. As one former member of the scene put it, “every company that was built in Silicon Alley depends on some other company that was built in Silicon Alley.”

Underneath it all was DoubleClick’s technology. “KO [Kevin O’Connor] would get up in these meetings and he was so aggressive,” a former VP of DoubleClick would later recall, “He said, ‘We are the company that is changing advertising and media. We won’t stop until we have world domination.‘ It wasn’t a job, it was a cult – a feel-good cult.”

A feel good cult is an apt summary of the spirit of DoubleClick, and of Silicon Alley, and of many of the dot-coms of the late 90’s. They were for true believers. Skeptics need not apply.

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