Ms. Srinivasan, who grew up in Kansas, was an undergraduate attending a tech-focused Stanford program in Kyoto, Japan, when she got to know two fellow students over shared meals — Jerry Yang and David Filo. After graduation, she was working on the Cyc Project, an early effort to create artificial intelligence, when the pair asked her to help them turn their directory into a real company.
“Jerry and David knew that I alphabetized my CDs,” Ms. Srinivasan, 44, said in an interview in her Palo Alto, Calif., home. “My sock drawer is quite beautiful.”
When she joined, her business card read Ontological Yahoo, a term reflecting her philosophical approach to the job. “This is not a perfunctory file-keeping exercise. This is defining the nature of being,” she said. “Categories and classifications are the basis for each of our worldviews. ”
Faced with the vastness of the web, Yahoo surfers hoped to identify the most complete, relevant or interesting sites on a given subject. To choose which topics to focus on, the surfers relied in part on a daily log of visitors’ top queries.
Once in a while, surfers made mistakes. For instance, they initially categorized Messianic Judaism as a Jewish sect, failing to notice that its adherents, who follow many Jewish traditions, believe that Jesus Christ was the Messiah, a defining trait of Christians. “We had faxes coming in nonstop from rabbis,” Ms. Srinivasan said.
Yahoo also offered automated search tools by teaming up with various companies, including AltaVista and Google. Eventually, though, Yahoo realized that it had to develop its own version of the technology.
Human judgment — what Mr. Yang referred to as “the voice of Yahoo” — remained a core value of the company. When the Grateful Dead musician Jerry Garcia died in August 1995, Yahoo searches on him spiked immediately. The surfers put a Garcia link on the home page. “That was the birth of Yahoo News,” Ms. Srinivasan said. Today, it remains one of the most popular online news portals.
The surfers’ role as corporate conscience expanded with the company. They worked on a child-safe version of Yahoo, called Yahooligans. They selected the news headlines worthy of home-page display. Over time, Ms. Srinivasan and her team even fielded questions like how much cleavage to allow on home-page ads.
Despite its efforts, Yahoo kept losing ground to Google in search. Microsoft made an unsuccessful hostile bid to buy the weakened company in 2008. Ms. Srinivasan left two years later, soon after Mr. Yang stepped down as chief executive. “In Japan, they have a saying: Leave when the cherry blossoms are full,” she said.
Ms. Srinivasan now splits her time between Palo Alto and Brooklyn, where she is working on a music start-up, Loove. The company is trying to revamp how the music industry works and help audiences understand the full story behind what they listen to, much as the farm-to-table movement did for food.
She also sits on the board of trustees of her alma mater, Stanford, a school that has churned out several generations of Silicon Valley moguls. But unlike many former technology executives, Ms. Srinivasan focuses her attention there on the arts and humanities.
“Tech is sexy. It’s employable. Parents love it,” she said. “All of that isn’t worth a hill of beans unless we know why, to what end. We call it the humanities for a reason.”
Yahoo, like the early web itself, was largely focused on American content. But it had global ambitions. Seana Meek, an Alberta native and a single mother, was working for Futurekids, which taught children computer basics, when Yahoo hired her to organize the Canadian sites in its directory.
For Ms. Meek personally, it kicked off a 20-year career odyssey through modern Silicon Valley and some of the tech industry’s most significant trends: e-commerce, virtual reality, fraud-fighting — even a mobile haircut app.
When she started, Yahoo was fumbling in Canada. Technically, it had a separate Canada site, but it relied on the American directory for its searches.
Employees asked her why the most popular search term among Canadian users was the word Canada. “That’s not a mystery,” Ms. Meek, 41, recalled saying. “In Canada, you do ‘government’ and you get American results. So you do ‘government Canada.’ You do anything and then you add ‘Canada’ to it.”
After the dot-com bubble burst in 2000, Yahoo’s dysfunctions began to surface. In 2002, the company transferred Ms. Meek’s job to Toronto. Less than 90 days later, it closed that office and sent her and two engineers back to the American headquarters.
She got a promotion from the mess: Yahoo put her in charge of the content, ads and business deals for Yahoo Canada. She was nicknamed Captain Canada and had a ringside seat to one of the company’s biggest decisions — dumping Google as a search partner and switching to technology from its Inktomi acquisition instead. “They were scared to do it. So they did it in Canada first,” she said.
In 2008, she left the company, embarking on a journey through Silicon Valley’s laboratory of business ideas, big and small. First she joined a tiny start-up, Picateers, that was trying to reinvent the school portrait business. It folded a year later.
From there she went to Linden Lab, the creator of Second Life, the tech industry’s first big foray into virtual reality. Players interacted with one another online in a 3-D simulated world, where they could buy and sell things, make friends, or just gawk at the scenery.
Second Life was an extraordinary experiment in human behavior, she said. An employee could change something in the virtual world, then just watch what happened. “You are literally a god,” she said.
Next for her was Eventbrite, an online event-planning and ticketing company. There she worked to protect against credit card fraud.
In 2013, she abandoned the corporate life to make a movie, a still-unreleased indie thriller, called “Veracruz.” Now she runs her own one-person firm, Snare Labs, which helps small merchants detect suspicious transactions. She is also working with her nephew on an app, Sharpcut, to summon barbers on demand.
And she says, she is casting about for the next challenge. “It’s a funny time in my life where there is definitely no script,” she said.
Matthew Mustapick and Amey Mathews
YOGA AND ACOUSTIC GUITARS
Working long hours in close quarters, it was inevitable that some surfers would find romance.
For Matthew Mustapick and Amey Mathews, working at Yahoo didn’t just lead to love. The lessons they learned — and the money they made from the stock they received as early employees — allowed them to achieve a different kind of Silicon Valley dream: dropping out of tech to do their own thing.
Ms. Mathews, who had a fine arts degree from Stanford, joined in 1998 after responding to an ad looking for a speaker of Scandinavian languages. “I told them I didn’t speak any Scandinavian languages — but I speak Italian and you should have someone who speaks Italian,” she recalled during an interview at the couple’s home in Soquel, Calif.
Yahoo had an Italian speaker already, but she got a job anyway. Mr. Mustapick sat in a nearby cubicle, and they eventually became a couple.
Surfers were free to reflect their personal interests in the directory. Ms. Mathews loved animals and indexed all the dogs, cattle, even miniature donkeys, she could find. Mr. Mustapick was fond of cataloging oddities like prosthetic testicles for pets that had been neutered.
Mr. Mustapick left Yahoo in early 2002. Ms. Mathews followed later that year.
Ms. Mathews, who became a yoga teacher while at Yahoo, started teaching full time when she left. Yahoo, in fact, became one of her first clients. The Yahoo stock provided a vital cushion.
“I could afford to lose money for a whole year when no one came to my class,” she said.
Mr. Mustapick turned toward music. “I always wanted to learn how to play electric guitar like Scott Henderson,” he said, referring to the jazz and blues guitarist. That interest led him in an unexpected direction — he began building acoustic guitars with an eye toward selling them.
Having looked at hundreds of thousands of websites while at Yahoo, he had a good sense of how to market online, well before the era of Twitter and self-promotion as a national pastime. He built a website and posted photos of guitars he was building so customers could watch the progress.
And he consciously befriended the right people. “They just put the word out for me,” he said. “That was the sort of thing I learned at Yahoo that you could do.”
He ended up making about 100 guitars, selling them for $3,000 to $10,000 apiece, before closing the business a few years ago. Mr. Mustapick, 47, is now studying jazz piano.
Still, she remembers Yahoo fondly. “I loved being around that many smart, interesting, engaged people,” she said. “I actively miss that in my daily life — not enough to go get a job and give up what I’m doing, but I do miss it.”
BACK FOR ROUND 3
Nine years ago, Gordon Hurd quit Yahoo for the second time. In June, he began working for the company again — Round 3 — this time as a freelance writer.
In the intervening years, Mr. Hurd toured the struggling new-media landscape — first, the Yahoo archrival AOL; then, Interactive One, a network of black news and culture sites; later, First Look Media, created by the eBay founder Pierre M. Omidyar; and most recently, a men’s fashion site, Man’s Life. There was even a brief stint at McKinsey & Company, the consulting firm and “the most corporate place you could go,” he said.
He is one of many surfers who left, then came back through the revolving door, sometimes unexpectedly. One group of ex-surfers jumped to Polyvore, a social shopping start-up founded by three Yahoo engineers in 2007, only to wind up back at Yahoo last year when it bought the company.
Mr. Hurd’s first run with Yahoo started in 1998 when he was hired to organize the business and finance parts of the directory. The starting pay was only $35,000 a year, he recalled. But there were stock options.
“I didn’t make millions by any means,” said Mr. Hurd, 45, in a phone interview from Brooklyn, where he lives. But he bought a house.
A restless soul, he left Yahoo in 2002 to become an investigative reporter for a local magazine. Less than a year later, with a second child on the way, Mr. Hurd returned to Yahoo, eventually helping run the influential home page.
In 2007, he hopped to McKinsey and then quickly to AOL, where he ran Asylum.com, a lifestyle site aimed at men age 18 to 34. The business model was to create vast amounts of content in the hope that visitors would click on ads.
That didn’t happen. “What it underlined is how much of a commodity content was,” Mr. Hurd said. Asylum was shut down.
Mr. Hurd moved on to Interactive One, the digital arm of Radio One, the largest black-owned radio broadcaster in the United States, which struggled to crack the content code, too. Volume trumped quality. “You know people will click on a subway-fight video, but you want to talk about what it’s like to be a millennial of color,” Mr. Hurd said.
Which is how, today, Mr. Hurd is back at Yahoo, writing articles for its style site while he ponders his next move.
More than ever, he thinks there is a need for the type of work that Yahoo’s surfers did 20 years ago. “The web has gotten so big that you need people to curate it,” he said.
However, he sees that curation coming from subject experts, not mass-audience sites like Yahoo. Niche sites with a devoted following could work with select sponsors hoping to reach a particular audience, he said.
“If you’re a person who’s really dedicated to the art of handmade knives, and you set out to categorize the sites of handmade knives, only you can do that. Google can never do that,” Mr. Hurd said.
A GRAND ADVENTURE
When Becky Uline graduated from Bowling Green State University in Ohio in 1996, she didn’t really know what she wanted to do with her life. A friend was raving that he had discovered paradise — living in Northern California and working for a company few people had ever heard of, Yahoo.
She and another Bowling Green graduate, Michelle Heimburger, thought it would be a grand adventure. They both got hired as surfers and rented an apartment together.
The building was so empty at first that surfers would zip through it on in-line skates. “We would sleep under our desks,” Ms. Uline, 42, recalled during an interview at her current home in Oakland, Calif.
Her roommate, Ms. Heimburger, made headlines a few years later when she spent $350,000 — part of her Yahoo stock windfall — to buy the century-old Franklin Castle in her hometown, Cleveland. To celebrate, she threw a huge housewarming party, inviting all of Yahoo and the Cleveland Indians baseball team to the festivities.
In 2001, Ms. Uline gave her notice. She wanted to travel the world, financed in part by her Yahoo nest egg.
Paris became a favorite haunt. “I would sublet my apartment out for a few months and just go and work from wherever,” she said. She freelanced for Yahoo and also tapped the vast network of surfer alumni, landing work at the visual-search start-up SearchMe and elsewhere.
Six years ago, she stopped wandering and decided to focus on her music. The year 2013 was big: her band, the Northerlies, released its debut album; she married the guitar player, Brian Anderson, who had worked at Excite, another early search site; and their son, Neil, was born.
Yahoo’s decline is sad, Ms. Uline said, but she still feels a connection. Her closest friends are former Yahoos, including Ms. Heimburger, who married yet another surfer and lives in London.
A few months ago, Ms. Uline, said, she dropped Yahoo as her home page, but she missed it and changed it back. “I still use Yahoo search. I want them to get the revenue,” she said.
SURFING BY ANOTHER NAME
When Yahoo set out to hire surfers, it invented a new job category. The closest match may have been bookstore clerk — and Kepler’s Books in nearby Menlo Park turned into a recruitment hotbed. About a dozen surfers were hired away from the shop, including ConnieAlice Hungate.
Ms. Hungate, 46, is still at Yahoo more than 18 years later, supervising what remains of the surfer team. She said the group, renamed content analysis and management, is still vital to the company’s ambitions to remain a player in web search.
Search ads bring in nearly half of Yahoo’s revenue. Under a 2010 deal with Microsoft, Yahoo uses Microsoft’s Bing search engine for most basic queries and ads.
Ms. Mayer, Yahoo’s chief executive, has devoted vast resources to search technology — particularly on mobile devices — in an attempt to leapfrog Google, though the company has little to show for it so far.
Ms. Hungate said her team helped train Yahoo’s search algorithms to provide more relevant results. The mobile search app, for example, now automatically pulls up suggestions for nearby places to eat when lunchtime rolls around.
The surfers also worked on the recent release of Yahoo’s Radar travel app, which uses a messaging-style interface to recommend restaurants and activities based on data from TripAdvisor and Yelp. “We’re doing all kinds of experiments every day,” Ms. Hungate said.
The Elvis sculpture, a 1998 gift from a Yahoo user, still watches over the department, and the turnip-carving contest is held every Halloween — with results posted on Flickr, the photo-sharing service owned by Yahoo.
Ms. Hungate said she was not worried about what would happen to the surfers if the company was sold. “Information management is a core need in technology,” she said. “We’ll adapt.”