Is There a Place for Idealism in Silicon Valley? A Tale of Early Yahoo

I worked at Yahoo for just four years, but they were the glory years --  1996-2000, before Google ate its lunch -- and its breakfast and dinner, too.

Back then, as companies were discovering just how much marketing could be done on the Web, and teens concluded you weren’t anyone until you put up your own Sailor Moon fan page (see here, '90s fans), we intrepid band of early Yahoo employees engaged in a most quixotic quest: organizing and interpreting the online world so the public could make the best use of it.

We know the rest of the story, which essentially has now ended.(Here’s a piece called “Yahoo’s 12 Biggest mistakes.” That you have to click through a dozen separate photos to view all 12 says a lot about what’s gone wrong on the Web since 1996.)

But I want to talk about that early team of employees and what happened to them as Yahoo transitioned from promising startup to global media giant, because I think it says something about the natural evolution from idealism to not-so-much in Silicon Valley.

The department I worked in was called Surfing (that’s what it said on my business card), a reference to one of the earliest metaphors for losing oneself on the web. When I joined, this group made up more than a third of the company. Mostly, we were in charge of creating Yahoo’s now-defunct directory of websites, the main “product” Yahoo offered in this pre-Google epoch, when Internet search was primitive.

The vast majority of these early web workers were not hardcore techies. They’d been recruited to categorize the tsunami of website submissions with which Yahoo was exponentially inundated, and they came from the ranks of library school students, bookstore clerks, and other professions fated to result in the semi-penury of liberal arts life. Remember the movie "Slacker," about eccentric 20-somethings wandering desultorily through Austin? Give those characters a steady salary, health insurance and a chance to indulge their various monomanias, and that was the Surfing department.

While each surfer had his or her own particular specialty -- music, movies, sports, religion -- the organization of the directory was a decidedly community affair, with email debates lasting days on end about the creation of a new category or the renaming of another. While some of these discussions were arcane and no doubt resulted in tens of thousands of dollars in opportunity costs, they could also be freighted with political implications. For example, should the category of  websites opposed to abortion be called “anti-choice,” “pro-life,” or “anti-abortion”? Do we call it “Myanmar” or “Burma?" 

At the time, Yahoo was the only game in town when it came to putting the web into some coherent state, so the surfers felt a deep responsibility to consider all sides and get it right. What was at stake, they felt, was nothing less than how people view the world.

The ethos of early-Yahoo was also one of radical free speech and inclusion: Any website was eligible for placement on any topic, with two notable exceptions: bomb-making and child pornography. Multiple websites about the truth behind JFK's assassination? Create a category. Submissions devoted to wearing diapers as a sexual fetish? Create a category. Websites dedicated to slamming a particular corporation? Category.

These precepts, as much as the exclamation point at the end of its name and the garish colors it favored in its design, were intrinsic to Yahoo's brand. The public really liked Yahoo because it was so blatantly egalitarian, such an earnest and enthusiastic steward of every byte of information that came its way. All the news that's fit to print, Yahoo seemed to say, was now everything. And that included your interests, too.

But as Yahoo grew, and its stock price soared to levels beyond all reason, the pressure to justify such lofty valuations increased. While the surfer-created directory remained the centerpiece of the Yahoo home page for quite some time, the business and product people whom Yahoo was hiring in droves had bigger fish to fry than arguing over whether it was legitimate to cross-reference the William Shakespeare category into the LGBT section. (Note: Real debate.)

I myself became embroiled in internal controversies connected to this rapidly changing culture. I edited a section devoted to aggregating and curating websites around particular news topics, and had many run-ins with the product people in charge of creating partnerships for Yahoo’s own news offerings, which at the time consisted mostly of articles from Reuters and AP. All of these employees were well-meaning, talented and smart, but the conflict arose because our jobs were fundamentally contradictory. While my task was to present a comprehensive picture of, say, the Israeli-Palestinian conflict, by presenting articles from both Israeli and Arab newspapers, theirs was to keep people within the bounds of Yahoo’s proprietary content for as long as possible, so the company could sell more ads.

(There was some hypocrisy involved on my part: I wanted to remain editorially pure but was nonetheless delighted to cash in my ever-more valuable stock options, which kept increasing because someone was keeping their eye on the bottom line.)

Eventually, the surfing department dwindled until it was completely marginal to Yahoo's business. Google's advanced search technology had rendered the surfers obsolete, and the surfing department slowly died. Some, having made a lot of money in the dotcom boom, left of their own accord, others were swept away through layoffs. But it wasn't just a bunch of liberal arts flakes the company was losing -- the ideals they had embodied were lost, as well, attenuating until they only existed as boilerplate language on company press releases. Near the end of my tenure, I sat in on a brainstorming session in which someone kept mentioning the names of media companies we could form partnerships with, without once ever mentioning the actual product such a partnership would create. In frustration, a manager, from the old days, interjected: “Stop talking about partnerships and start talking about what would be useful to our users.” A few years later, during a contracting stint, I noted that so-called editorial meetings revolved entirely around which piece of content would entice users to click on it and why; nary a moment was squandered on its actual editorial worth.

So, how is this history relevant today? Well, recently I interviewed B.J. Fogg, who runs the Stanford Persuasive Tech Lab, dedicated to teaching tech folks -- including at one time the co-founder of Instagram -- how to attract and keep users on websites and apps. I was writing about a topic that's been getting a lot of play-- the claim by some tech insiders that Facebook and other companies are using designs that trigger compulsivity.

Fogg said he got to know some of the early Facebook employees, and found them genuinely motivated by a desire to do good.

“The individual people at Facebook," he recalled, "the people that I met, really wanted to make the world more harmonious, bring people together, create empathy and so on."

But, he continued, “Often [Facebook’s] business goals can be at odds with the human-centered approach to design. There’s a conflict there between what they need to do as an advertising company and what’s going to be really good for people.”

Idealistic goals are frequently espoused by bluetooth-wearing tech CEOs at conferences and TED Talks. (Take a look at Elizabeth Holmes of Theranos, placing her company squarely in the realm of “patient empowerment," for an ironic example of the genre.) But once the IPO launches, is there really any room for idealism?

I think it says something that the web project with the ethos closest to that of early Yahoo is Wikipedia, a nonprofit created almost entirely by unpaid volunteers.

What made Yahoo so cool at its start is that it literally was doing well by doing good. But in retrospect, I think that was the case because at the dawn of the commercial web those ideals happened to intersect with a good business model.

When a better one -- or the perception of a better one -- came along, that idealism went 404.