Brotopia Read online

  Jobs certainly deserves credit for helping bring women into the computer marketplace as buyers. The first computer in my childhood home was an Apple II, and my mom, a schoolteacher with no technical background, used it with pride. Inside the industry, Jobs could have become an example of all that the tech industry could gain by bringing in a more diverse workforce. His vision and understanding of the consumer marketplace demonstrated what could be changed when different voices were added to the product development cycle. Unfortunately, the industry took the wrong lesson from Jobs’s achievement and only succeeded in creating a new stereotype, one that—once again—favored men over women.

  Looking at the hypercool Steve Jobs, investors noted his supreme self-confidence and fearlessness of risk and decided that those were keys to entrepreneurial achievement. Investors stopped gravitating to awkward, antisocial nerds and started looking for founders with über-confidence, a penchant for grandiosity, and a ravenous appetite for risk. The ideal candidates married the best of Wozniak and Jobs: technical skill plus daring and determination, simultaneously geeky and cool. Jobs became a new stereotype—the model for a new generation of young men aspiring to become the rock stars of the computer revolution.

  HOW TRILOGY WROTE THE BRO CODE

  Silicon Valley has mostly forgotten the tale of Trilogy, a start-up that glittered brightly in the mid-1990s before burning out. But the company is important here because it exemplifies several distinct cultural shifts that worsened the working environment for women. Led by a charismatic young Stanford dropout, Joe Liemandt, Trilogy pioneered new recruiting strategies in the tech industry, selected a different type of computer programmer, and encouraged an insane amount of risk—all while helping to trademark the work-hard, party-harder brogrammer culture we’ve come to know, complete with Dom Pérignon, strippers, and high-stakes gambling. Trilogy did boast a few women among its key early employees, but the net effect of the company, and others like it in the late 1990s, was to create an even chillier climate for women in technology.

  In the mid-1990s, Trilogy was one of the most desirable places to work in the industry, as hot as Microsoft in its heyday, and also a lot cooler. “In the ’90s, if you majored in computer science, you were a nerd. You were definitely socially backward,” says Jocelyn Goldfein, who worked at Trilogy and went on to become director of engineering at Facebook. Trilogy promised to change that. As Goldfein puts it, “Going to Trilogy was a little bit like Revenge of the Nerds. It was this feeling of ‘Oh, we can be cool too but in our own nerdy way.’ That’s what made it feel glamorous.”

  Liemandt started the company in 1989, the same year Steve Jobs lectured on Stanford’s campus as part of the university’s long-running “View from the Top” interview series. Liemandt had interviewed for a job at Microsoft but believed that he, like Jobs, was destined for something greater. As he told students at Harvard nearly a decade later, he and his co-founders “wanted their work to matter,” and because they were the only people who thought they were “good enough,” they had to start their own company. After countless hours spent poring over the top fifty software companies and brainstorming various products, Liemandt came up with what he believed was the right opportunity: his company would vastly improve the efficiency of the selling process by creating software to give salespeople working on complex deals quicker access to data and other information.

  Liemandt, who was independently wealthy, still maxed out dozens of credit cards bootstrapping his fledgling company. He majored in economics because he thought it was “easy,” which allowed him to spend as much time as he wanted working on his start-up while taking computer science and engineering classes on the side, though he ultimately dropped out of Stanford during his senior year.

  He boasted to anyone who would listen that he had a $500 million idea. In another era, investors would have steered clear of a college dropout making such an outrageous claim. But in the 1990s, this sort of over-the-top bravado was exactly what people expected from young tech geniuses. When Steve Jobs used his charisma to overcome or hide inconvenient facts, people called it his reality distortion field. As Liemandt demonstrated, Jobs was far from the only entrepreneur adept at distorting reality.

  Liemandt himself admitted to the Stanford Daily newspaper that the initial product “sucked,” but once they finally got it to work, Trilogy sold a major software deal to Hewlett-Packard. Silicon Graphics, a large technology firm that had pulled out of a deal with Trilogy, came back to the table asking to renegotiate. Liemandt responded, “We will, but the price has tripled.” Silicon Graphics gave in and was followed by major clients such as IBM, Alcatel, and Boeing. Thanks to Trilogy, businesses could create giant custom catalogs (imagine all the options that might come with a plane, for example) that salespeople could use to drive deals. Trilogy was off on one of the greatest runs for a software company in tech history.

  With Trilogy still in start-up mode, and Microsoft ratcheting up the competition for talent, Liemandt made a decision about hiring that might have been the single biggest bet of his entire career. He wagered that talented, overachieving students with zero real-world experience—that is, people like him—would be the key to Trilogy’s success. As a result of this decision, the vast majority of Trilogy’s hires were new graduates, and more experienced adults became a rare breed. Jocelyn Goldfein says the ethos of the company was “We’re elite talent. It’s potential and talent, not experience, that has merit.” With Liemandt’s believing passionately that success could only flow from a meritocratic hiring process, “only the best” became the shorthand with which Trilogians described themselves and the candidates they were looking for. If this philosophy now sounds familiar, that’s because Liemandt’s bet would affect the recruiting process for tech companies for decades to come.

  Trilogy “turned college recruiting into an art form,” writes one Austin reporter. The company targeted top schools such as Princeton and Stanford, plying students with gifts ranging from CDs of Austin bands to computers and even cars. One female recruiter, a non-techie who was one of Trilogy’s top recruiters, passed out laptops to students at Berkeley and hosted lavish dinners at top restaurants in San Francisco and Palo Alto. “You name it. There was no limit in terms of where we’d take people,” she says. “There was no accountability or structure. It was just ‘Here’s a credit card; go figure it out and find some engineers.’” The Trilogians of the future were made to feel more special than they’d ever felt in their lives.

  Former Trilogy director John Lilly, who went on to run the Mozilla browser and become a venture capitalist at Greylock Partners, one of the industry’s top firms, recalls a red convertible Mustang waiting for him at the airport. Most important, the recruiters were mainly women who were “all twenty-two and hot,” as one former employee put it. Trilogians had fun speculating about which recruiters were former strippers (there’s no evidence that any of them were) and which might be hooking up with the boss. “Joe was a total bro,” one former Trilogian told me. “The ‘bro thing’ started way earlier than people think.” His idea, quite clearly, was to hire good-looking women who, in other circumstances, might never give an engineer the time of day. Of course, the unstated premise of this hiring practice is that the target candidates, the students who’d be flattered and excited at the attentions of these sexy recruiters, would be men, not women.

  THE CULTURE-FIT CHALLENGE

  One of the assessment measures Trilogy helped pioneer, which became widely used in the industry, was to have candidates demonstrate how well they could think on their feet by conducting a quick succession of brainteasers. Gary Chou, who was taking postgraduate computer science classes at Princeton before being hired by Trilogy as a product manager in 1998, likened the interview process to an American Idol competition. “You would go through round after round of brainteasers on campus,” Chou recalls. These tests included questions like “How much would you charge to wash all the windows in San Francisco?” An
d “How many piano tuners are there in the world?”

  What did these brainteasers actually test for? There is little to suggest that they had anything to do with being a good coder or engineer. More likely, they helped Trilogy hire people who were a cultural fit. The company was looking for people with extreme confidence—those who would happily riff on a problem about which they had no actual expertise.

  On its face, an offer from Trilogy was the opportunity of a lifetime. Kids, right out of college, were trained as quickly as possible and given the chance to run major parts of the business immediately, so they could have instant effect. At the same time, early Trilogy executives compared building the company to building a cult. “The first thing you have to do in a cult is isolate,” Trilogy’s former VP John Price remembered two decades later. To achieve that, Liemandt had moved the company from Palo Alto to Austin, Texas, in 1992, which at that time wasn’t the tech hot spot it is today. “The reason Joe put it in Austin was so you didn’t have anything else to do,” says John Lilly. “If we’re in Silicon Valley, we’ll go out and screw around, but in Austin there’s nothing else to do except go out and drink . . . The company was oriented towards drinking and working very hard. Everything was very intense.” Hired at age twenty-four, Lilly would have been just another cog in the wheel at a big tech firm, but his first job as a Trilogian was as a director on Liemandt’s staff.

  New hires immediately spent twelve weeks bonding and training at a company boot camp called Trilogy University. The idea was to “push new recruits to their limits” with an unrelenting series of technical and emotional challenges while simultaneously indoctrinating them with Trilogy’s core vision and values. Price said they wanted to “create cohesion and bonding at the level military guys have in a fox hole when they have bullets flying overhead,” then added, “If you ever study cults, this is how they do it.” Recruits, encouraged to display their youthful bravado, emerged with extreme confidence and a near-patriotic devotion to Trilogy.

  After graduating from TU, new hires plunged into the company culture of hard work and hard play. “I worked nonstop,” says Christy Jones, Trilogy’s sole female co-founder. “I didn’t go on vacation. We called holidays competitive advantage days because no one else was working. It was a chance to get ahead. I would drive home at 11:30 at night.”

  By the end of the workweek, everyone was ready to let loose. Aside from “only the best,” another Trilogy motto was “money, recruiters, beer, repeat,” according to early employees. “Friday at 5:00 p.m., party on the patio,” says Lilly. At 9:00 p.m., the team might grab dinner at a Mexican restaurant, then spontaneously hop on a plane to Vegas, often led by Liemandt himself. Inevitably, they’d stay up all night, crashing in suites at the MGM Grand through the weekend. Liemandt was notorious at the tables and in strip clubs, becoming known as Hundred-Dollar Joe. He would expect his team members to bet all or nothing at the tables, not just hundreds but thousands (and sometimes even tens of thousands) of dollars at a time.

  This sort of boorish behavior was talked up as a part of the Trilogy ethos, important because it cultivated people’s willingness to play for the highest stakes and taught lessons about risk and reward. The Trilogians would catch a flight back to Austin on Sunday, hydrate, and go to work on Monday, even more devoted to Hundred-Dollar Joe. “Challenging male behavior has been in companies forever. This was one of the first tech companies that really spiked it,” Lilly told me. “They did hire some excellent women, but also did a lot of things that were problematic for women.”

  Insane work hours, drinking, gambling, Vegas, strip clubs—throw in the prizing of youthful brilliance over experience, and this was the company culture that new and prospective employees knew they needed to fit. “When you have a culture that is so male dominated, where drinking is a huge part of the culture, where you’re talking about doing deals in the millions of dollars, every aspect of that is going to kind of reek of a certain mentality,” says Gary Chou. “It’s completely hostile for women.” Trilogy was among the first in a long line of tech start-ups that required assimilating into a culture of masculine arrogance that many people, women especially, might not want to sign up for.

  Not every man is happy and productive in a bro culture, but women, as a group, are especially unlikely to feel comfortable. Much peer-reviewed social science suggests that men—whether due to nature or nurture—are more given to the particular type of grandiose self-assessment displayed by the many tech wunderkinder dating all the way back to Jobs himself. In a paper that consolidated thirty-one years of research on narcissism and involved nearly half a million participants, Emily Grijalva of SUNY at Buffalo found that men consistently score higher than women when it comes to narcissistic traits such as exhibitionism, feelings of entitlement, and the willingness to employ unethical or exploitative behavior to get ahead.

  Trilogy kicked off an era in which lofty self-confidence seemed to be a critical qualification for both tech entrepreneurs and the engineers they hired. Recall those brainteasers that Trilogy and other major tech companies used throughout the 1990s and into the next two decades. There has never been any evidence that they were useful in measuring who would be a good programmer. Yet it took until 2013 for Google to finally stop using them. “Brainteasers are a complete waste of time,” Google’s longtime former head of HR Laszlo Bock admitted to the New York Times in 2013. “They don’t predict anything.”

  Well, maybe not anything useful, but they might have been good predictors of the sort of hyper self-confidence men are more prone to. When an employer asked something like “How many golf balls can fit into a double-decker bus,” he or she was basically saying this to prospective candidates: “We are going to ask you a question that has no relation to your job and one you’ve had no training in how to answer. Do you have the chutzpah to pretend that you can?”

  Men are far likelier than women to take risks like these and to feel comfortable doing so. Geoff Trickey, managing director of Psychological Consultancy Limited, a group of business psychologists, studied risk-taking behavior in over seventy-five hundred people and found that risk takers who are both impulsive and fearless were twice as likely to be men as women. On the flip side, female risk takers were roughly twice as likely to be more wary and judicious than men.

  Additional compelling research suggests that high-achieving women suffer from “imposter syndrome,” a term coined in 1978 by two psychologists, Pauline Rose Clance and Suzanne Imes, to summarize how women often feel undeserving of their success. Despite their concrete achievements, these researchers said, women often believe they are not that smart and will eventually be exposed as frauds. Other researchers have found that women won’t apply for jobs unless they meet 100 percent of the qualifications, while men will apply as long as they have 60 percent of the boxes checked. Imposter syndrome has been found in all kinds of industries as well as in professions such as law and medicine, where the metrics for success and achievement are widely understood and agreed upon. How well, then, could women be expected to fare, on average, in the dot-com world of the 1990s, when success almost required a willingness to be an imposter? Companies were worth what investors believed they were worth, and investors based their assessments on the founders’ claims, often wild and fanciful, and their aplomb.

  Liemandt’s recipe for success turned out to be a recipe for disaster. Though investors clamored to buy shares in a Trilogy IPO, Liemandt kept Trilogy private, allowing the company—and employees—to experiment with new businesses. pcOrder.com, which involved preloading entire computer systems with Trilogy software and selling them over the internet, became Trilogy’s first spin-off. In 1999, at the height of the dot-com bubble, pcOrder.com went public, raising $46.2 million—big bucks back then—on its first day of trading.

  Trilogy chased the hype, building multiple other online businesses, selling everything from cars and appliances to insurance online, powered by the company’s original sales so
ftware. As the dot-com boom hit fever pitch, Trilogy and its subsidiaries commanded stratospheric valuations but had little to show for it. “None of them were very good,” Lilly says of the various businesses. (He ultimately left Trilogy after sixteen months for a job at Apple, because he didn’t share Liemandt’s values.) Even the company’s core product was mediocre. “The ugly truth was that the sales configurator was a piece of crap software,” a former employee told me. “It was super complicated, hard to use, and required tons of professional services fees. The model was hype up crappy software to sell expensive consulting hours.” On top of this, some of the new businesses started to overlap, and Trilogy began competing with itself. pcOrder’s stock plunged, but not before early Trilogians made bank.

  Jocelyn Goldfein, who worked at pcOrder, says, “Everyone got rich off a company that was basically nothing. Trilogy was full of hubris, the hubris of the era except theirs predated the era.” The company was the early 1990s model for a type of bluster and risk taking that would come to characterize Silicon Valley over the next decade.

  For Trilogy’s tenth anniversary, in 1999, Liemandt flew hundreds of employees to the Bahamas, where they stayed at the Atlantis Resort, and gifted employees crystal vases from Tiffany and bottles of Dom Pérignon. When the first tech bubble burst, Liemandt’s net worth plummeted, and in 2001 hundreds of Trilogy employees were laid off. Today, Liemandt is quietly running a downsized Trilogy and keeping a low profile in Austin. He did not respond to multiple requests for comment.