When I asked Pratt why he had never shared his role in Lena's story, [...] He seemed nonplussed when I pressed him about the controversy that still surrounds the choice of this test photo. “I haven't paid attention to [the controversy] at all,” he said. "[...] It was just natural that we would use a good-quality image, and some of the best images were in Playboy. It was not sexist."

Besides, no one could have been offended, he told me, because there were no women in the classroom at the time.

Ten years ago, the techies who became suddenly and extravagantly wealthy were were often self-conscious about flaunting their riches. It used to be that it wasn't cool, after your IPO, to pull up to the office in a Ferrari. But staying humble and empathic to those not in your rarefied circle or zip code becomes increasingly difficult over time. It is so much easier to tell yourself that you've worked harder than others - or were simply smarter than they - and that you therefore deserve all the prizes.

"Absolutely, wealth can change people," one former Google executive told me. "It disconnects you from average people. It's a big, big problem. You assume your experiences are everyone's experiences, and with wealth that becomes dangerous. Moral exceptionalism is disgusting, and Silicon Valley has tons of it, and it stems fro a lack of empathy. You assume the people who don't see the world as you do are uneducated or stupid."

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 [...] "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 meritoratic hiring process, "only the best" became the shorthand with which Trilogians described themselves and hte candidates they were looking for. [...]

[...] 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. [...] "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?"

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 Perignon. 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.

[...] Rabois believes PayPal is a "perfect validation of merit" and of Silicon Valley as a meritocracy. "None of us had any connection to anyone important in Silicon Valley," he told me. "We went from complete misfits to the establishment in five years. We were literally nobodies.[...]" The early PayPal team would go on to found some of the biggest companies in Silicon Valley, including Tesla, SpaceX, LinkedIn, YouTube, and Yelp. Thiel funded and joined the board of Facebook. Establishment achieved.

Obviously, Thiel didn't consider himself one of those doomed lemmings. But how does one find other nonlemmings? Just look for unusual behavior. In his book, Thiel notes with pride that "of the six people who started PayPal, four had built bombs in high school." In our interview, he told me, "There is something that's always quite extreme about the personalities that go into starting a company ... Having some extreme personalities, I think, is a somewhat good thing."

But we didn't have a term for "meritocracy" until the twentieth century, when the British sociologist and politician Michael Young wrote a book in 1958 warning of how dangerous the world's relatively new method of establishing status might be. In his novel The Rise of the Meritocracy, Young portrayed a dystopian Britain in which status based on birth and lineage was replaced by status based on education and achievement. Young wasn't advocating for a return to the old system, but he did see grave dangers in the new embrace of meritocracy, eerily predicting that in this new world, status would still be accessible only to a select few: those who had access to elite education. As a result, meritocracy would produce a new social stratification and a sense of moral exceptionalism.

Though Young's book was meant as a cautionary satire, the idea of meritocracy took off, all negative connotations forgotten, as the term for a new equality of opportunity [...]

That's when Young penned an op-ed for the Guardian in which he confessed he was "sadly disappointed" by his book's effect. "It is good sense to appoint individual people to jobs on their merit," he wrote. "It is the opposite when those who are judged to have merit of a particular kind harden into a new social class without room it in it for others ... If meritocrats believe, as more and more of them are encouraged to, that their advancement comes from their own merits, they can feel they deserve whatever they can get. They can be insufferably smug, much more so than the people who knew they had achieved advancement not on their own merit but because they were, as somebody's son or daughter, the benefitciares of neptosim. The newcomesr can actually believe they have morality on their side. As a result, general inequality has been becoming more grievous with every year that passes."

Sexist behavior often comes from the top, and in Holmes's telling that was the case at Cooliris, where the young CEO, Soujanya Bhumkar, gave the entire staff copies of the Kama Sutra [...] Bhumkar would often joke, "Thank God we don't have an HR team," [...]

[...] because most venture capitalists are men, they are likely to be more passionate about ideas that appeal to, well, men. When Lake was raising her seed round, she noticed that a fair number of little league coaching apps were getting funded. "I'm like, how big of a business is that? Seriously, a T-ball league? But your target audience is these VCs who manage their son's T-ball league," Lake says. [...]