— In the history of American higher education, it is hard to top the luck and timing of the Stanford class of 1994, whose members arrived on campus barely aware of what an email was, and yet grew up to help teach the rest of the planet to shop, send money, find love and navigate an ever-expanding online universe. They finished college precisely when and where the web was stirring to life, and it swept many of them up, transforming computer science and philosophy majors alike into dot-com founders, graduates with uncertain plans into early employees of Netscape, and their 20-year reunion weekend here in October into a miniature biography of the Internet. A few steps from the opening party, the original Yahoo servers, marked “1994,” stood at the entrance to an engineering building, enshrined in glass cases like religious artifacts. Brunch the next morning was hosted by a venture capitalist who had made a key investment in Facebook. At a football game, the alumni brandished “Fear the Nerds” signs and gossiped about a classmate who had recently sold the messaging service WhatsApp for over $20 billion. “I tell people I graduated from Stanford the day the web was born,” said another alumnus, Justin Kitch, whose senior thesis turned into a start-up that turned into an Intuit acquisition. Photo Photo The reunion told a more particular strand of Internet history as well. The university, already the most powerful incubator in Silicon Valley, embarked back then on a bold diversity experiment, trying to dismantle old gender and racial barriers. While women had traditionally lagged in business and finance, these students were present for the creation of an entirely new field of human endeavor, one intended to topple old conventions, embrace novel ways of doing things and promote entrepreneurship. In some fields, the women of the class went on to equal or outshine the men, including an Olympic gold medalist and the class’s best-known celebrity. Nearly half the 1,700-person class were women, and plenty were adventurous and inventive, tinkerers and computer camp veterans who competed fiercely in engineering contests; one won mention in the school paper for creating a taco-eating machine. Yet instead of narrowing gender gaps, the technology industry created vast new ones, according to interviews with dozens of members of the class and a broad array of Silicon Valley and Stanford figures. “We were sitting on an oil boom, and the fact is that the women played a support role instead of walking away with billion-dollar businesses,” said Kamy Wicoff, who founded a website for female writers. It was largely the men of the class who became the true creators, founding companies that changed behavior around the world and using the proceeds to fund new projects that extended their influence. Some of the women did well in technology, working at Google or Apple or hopping from one start-up adventure to the next. Few of them described experiencing the kinds of workplace abuses that have regularly cropped up among women in Silicon Valley. But even the most successful women could not match some of their male classmates’ achievements. Some female computer science majors had dropped out of the field, and few black or Hispanic women ever worked in technology at all. The only woman to ascend through the ranks of venture capital was shunted aside by her firm. Another appeared on the cover of Fortune magazine as a great hope for gender in Silicon Valley — just before unexpectedly leaving the company she had co-founded. Dozens of women stayed in safe jobs, in or out of technology, while they watched their spouses or former lab partners take on ambitious quests. If the wealth among alumni traveled across gender lines, it was mostly because so many had wed one another. When Jessica DiLullo Herrin, a cheerleader turned economics whiz, arrived at the tailgate party, her classmates quietly stared: She had founded two successful start-ups, a living exception to the rule. Photo Photo Not everyone was troubled by the imbalance. “If meritocracy exists anywhere on earth, it is in Silicon Valley,” David Sacks, an early figure at PayPal who went on to found other companies, emailed that weekend from San Francisco, where he was renovating one of the most expensive homes ever purchased in the city. Without even setting foot back on campus for the reunion, he was stirring up old ghosts. Because Stanford was so intertwined with the businesses it fostered, the relationships and debates of the group’s undergraduate years had continued to ripple through Silicon Valley, imprinting a new industry in ways no one had anticipated. Mr. Sacks had fought the school’s diversity efforts bitterly; those battles had first made him an outcast among many of his classmates, and then sparked his technology career. Every reunion is a reckoning about merit, choice and luck, but as the members of the class of ’94 told their stories, that weekend and in months of interviews before, they were also grappling with the nature of the industry some had helped create. Had the Internet failed to fulfill its promise to democratize business, or had the women missed the moment? Why did Silicon Valley celebrate some kinds of outsiders but not others? “The Internet was supposed to be the great equalizer,” said Gina Bianchini, the woman who had appeared on the cover of Fortune. “So why hasn’t our generation of women moved the needle?”

When Stanford students of the early 1990s got rejection letters, especially from banks and consulting firms, they often posted them on the doors of their dorm rooms, as if to thumb their noses at conventional notions of what they would achieve. Even by the standards of the young and Californian, their world felt open and new. Mikhail S. Gorbachev came to campus, talked about sweeping away the Cold War and pronounced that “the ideas and technologies of tomorrow are born here in California.” The front page of The Stanford Daily featured a picture of Rachel Maddow, a campus activist before she became a news host, locking lips with her girlfriend at a gay rights march, then a startling sight. The university retooled its curriculum and residential life to prepare its students for a more diverse future. No one was allowed to know the name of his or her freshman roommate before arriving on campus, to prevent prejudgments based on ethnic names. In seminars by day, students read texts by Aboriginal Australian writers; in the evenings, dorm counselors held programs on black and feminist issues. With no iPhones, text messages or even websites to distract them, students immersed themselves in long discussions about how sexism had expressed itself in their families back home or, in later years, about Condoleezza Rice’s policies as provost. The first issues of Wired magazine were published while they were undergraduates, capturing a spirit of optimism. “Life in cyberspace seems to be shaping up exactly like Thomas Jefferson would have wanted: founded on the primacy of individual liberty and a commitment to pluralism, diversity, and community,” Mitchell Kapor, founder of Lotus, would write in an early issue. So the residents of one dorm, Donner House, were floored in the spring of 1991 to discover graffiti in their common room reading, “If a woman says no, she means yes!” and “You’re all [expletive] slaves.” The graffiti, written by four students, caused an uproar and led to a dorm-wide meeting. Afterward, David Sacks, an awkward freshman who often had trouble looking other students in the eye yet showed a flair for theatrical, cutting remarks, argued that the graffiti writers had been treated unfairly. He made it clear that he found the graffiti itself deplorable, calling it “sexist and violent,” in his first essay for The Stanford Review, a conservative-libertarian campus newspaper. But he also argued that an earlier round of graffiti — including a crude statement about President George Bush — had been just as offensive. A dorm discussion of the incident had a “mob mentality,” he wrote. “Why was an apology demanded of the writers of the sexist graffiti,” he asked, and not of the Bush slur? Almost no one else in Donner House saw it that way. “I remember David being stunned by the reaction” to his arguments, Adrian Miller, his resident counselor at the time, said later. Shunned by many of his dorm mates, Mr. Sacks made a new home at The Review, which was founded by a law student named Peter Thiel to critique what he saw as incessant political correctness. He and Mr. Sacks saw themselves as relentless defenders of excellence, and they viewed the university’s diversity efforts as its enemy, a clunky, top-down effort at redistributing power. In the pages of The Review, they defined feminism in negative terms — alarmist, accusatory toward men, blind to inherent biological differences. Feminists “see phallocentrism in everything longer than it is wide,” Mr. Sacks wrote. “If you’re male and heterosexual at Stanford, you have sex and then you get screwed.” By his sophomore year, he was the editor of The Review. Photo Photo There were just a handful of women at The Review, and some were peeling away. “I didn’t think I could stand up” to Mr. Sacks, Samantha Hamlin, formerly Samantha Martinez-Colson, said in an interview, adding that as a Latina she found the social penalty for being a writer there to be too high. Years later, in interviews, Mr. Sacks and Mr. Thiel would emphasize The Review’s independence of spirit, its willingness to take on the political correctness that more than a few classmates found suffocating. “There was a creative contrarian ethos which encouraged rethinking problems from first principles, and not just accepting the world the way it was,” Keith Rabois, another former editor, said in an interview. But there was an ugly side as well; Mr. Rabois left campus in 1992 after yelling “Can’t wait until you die,” punctuating it with a homophobic slur. He said afterward that he had been protesting campus speech codes. Mr. Sacks was almost as abrasive, joking in print about an imaginary course called “Bathroom Self Defense for Heterosexuals.” The editors made easy fun of the excesses of Stanford’s diversity drive, but it was not clear that they recognized the basic concerns of many female and minority students — that they would not have the same opportunities as their white male peers. Photo Looking back years later, some alumni wondered aloud how well the thunderous debates about gender and race had really served them. At what turned out to be a formative hour for Silicon Valley, diversity had come to seem to them like a matter of overheated rhetorical contests instead of mutual compacts for success. As Mr. Sacks had predicted, identity politics pushed many people into homogeneous groups; Scott Walker, one of the only African-Americans in the class to try founding a start-up, said in an interview that he regretted spending so much time at his all-black fraternity, which took him away from the white friends from freshman year who went on to found and then invest in technology companies. But those debates did a great deal for Mr. Sacks. After graduation, he and Mr. Thiel published “The Diversity Myth,” a book-length critique of Stanford’s efforts. Within a few more years, he, Mr. Thiel, Mr. Rabois and others had transformed themselves into a close-knit network of technology entrepreneurs — innovators who created billion-dollar business after billion-dollar business, using the ideas, ethos and group bonds they had honed at The Stanford Review.

Before Jessica DiLullo became perhaps the most successful female entrepreneur in the class, the one whose career formed a map to what many others had missed, she was one of its least likely members. She had transferred from a community college, the daughter of a wild-child mother with whom she no longer spoke, a former high school cheerleader who had often skipped classes. Ms. DiLullo arrived as the beneficiary of another aspect of Stanford’s diversity drive, an effort to recruit students who were less privileged. In her first week, she ran into the valedictorian of her high school class, who was so surprised to see her that she blurted out, “You have got to be kidding me.” Scrambling to prove herself as an economics major, she quickly made friends who remember her as warm, practical and decisive. By the end of senior year, she was passing up an investment banking job to move to Texas to work for Trilogy, a software firm. Hungry and confident, she did not care what others thought. “I didn’t need a gold star from someone else,” she said later with a throaty laugh. Many of her female classmates made more conventional choices, going into law and finance, which were opening to women as never before. A large number of the women who were inclined toward science and information analysis chose to become physicians. Throwing yourself into the exhausting marathon of medical training at least promised a lasting, meaningful career; throwing yourself into an equally demanding start-up was likely to yield nothing at all. “The Internet was the Wild West,” said Arielle Miller Levitan, who enrolled in medical school. “You could do anything there, but it was such an unpaved path.” Technical skills were not strictly necessary to enter the field, but they helped, and male computer science majors had outnumbered females, four to one. Some women took posts at hardware and technology consulting firms, but within a few years of graduation, more of their male classmates were already starting companies. Photo Photo Photo Photo There was no time to waste. Before the Internet era, most revolved around the “sole possession of a piece of technology that was hard for others to replicate,” like a new kind of circuit, said John L. Hennessy, the Stanford president and an engineer-entrepreneur himself, during an interview over the reunion weekend. But with the web, “all of the sudden we began moving to a market where first mover advantage became enormous,” he said. Connection speeds were growing faster, Americans were starting to shop online, and multiplying e-commerce sites fought gladiatorial battles to control most every area of spending. Midway through the conversation, he paused. If the dawn of the start-up era meant that consumer-oriented ideas were becoming more important than proprietary technology, he asked himself aloud, shouldn’t more women have flooded in? “The natural inclination would have been, in the consumer space, with a lower technical investment, a lowering of the threshold for women to participate,” he said, sounding puzzled. But there were still many hoops women had greater trouble jumping through — components that had to be custom-built, capital that needed to be secured from a small number of mostly male-run venture firms. Ms. DiLullo blew past those limits; at 24, she threw herself into an idea for an online gift registry. When she and her business partner met with one venture capitalist, he looked at them and said, “I see the pretty girls. Beyond the pretty girls, what do you have for me?” They ignored the slight, took his money and dropped out of Stanford Business School to start their company, Della & James, which competed with WeddingChannel.com and then merged with it, riding the wave of the dot-com boom. In 1999, Ms. DiLullo appeared on “The Oprah Winfrey Show” as a can-do example of female entrepreneurship. Hundreds of women contacted her in the weeks after, wanting to know how they could start businesses, too. But a year later, the dot-com bubble burst, leaving Silicon Valley so despairing that some classmates remember the local U-Haul companies running out of trucks. The bust had come right before their 30th birthdays, just as many of them were looking for stable jobs that could accommodate marriage and children. A Slow Slide for Women in Technology The share of women working in technology dropped after the sector collapse in 2000. Although the sector recovered, participation by women is lower than in 1998. +2 pct. pt. 0 ’98 ’05 ’09 ’13 ’98 ’03 ’09 ’13 –2 All workers Managers –4 Change from 1998 in percentage of women in the technology sector Change from 1998 in percentage of technology managers who are women –6 –8 0 ’98 ’05 ’09 ’13 –2 pct. pt. All workers –4 Change from 1998 in percentage of women in the technology sector –6 +2 pct. pt. 0 ’98 ’03 ’09 ’13 –2 Managers –4 Change from 1998 in percentage of technology managers who are women –6 Even Ms. DiLullo retreated. She wanted to start companies, not work for them. But WeddingChannel.com had become a big organization with three co-founders, and she and her new husband, Chad Herrin, wanted children, which she could not reconcile in her mind with a dot-com life. So the class’s most prominent female entrepreneur moved back to Austin for her husband’s career and took a safe corporate job at Dell.

David Sacks, on the other hand, was unmarried and unencumbered, and in 1999 he left politics, his law degree and a job at the consulting firm McKinsey & Company to join his Stanford Review friends at a technology start-up, because of “the desire to live on the edge, to fight an epic battle, to experience in a very diluted way what previous generations must have felt as they prepared to go to war,” he wrote at the time. For his generation, he wrote, “instead of violence, unbridled capitalism has become the preferred vehicle for channeling their energy, intellect and aggression.” Led once again by Peter Thiel, the men had found a new way to translate their libertarian impulses and hatred of bureaucratic impediments: They wanted to create an alternative to the monetary system, but they settled for an electronic payment method that bypassed banks. They would go on to call their vision PayPal, and it provided Mr. Sacks with the war he craved: The new service fought competitors, regulators and Russian hackers who stole tens of millions of dollars. Photo Mr. Sacks almost wasn’t hired because of doubts that he could work well with others; during his job interview, he put the chief financial officer on notice that his own job would be totally different once Mr. Sacks arrived, Mr. Thiel remembered. But his lack of social grace became an asset, according to Mr. Thiel and other former colleagues. He did not waste time on meetings that seemed pointless, and he bluntly insisted that the engineers whittle an eight-page PayPal registration process down to one. Everyone knew Mr. Sacks was politically conservative, but in the office, he was less bombastic. He had become a manager, he said in an interview, and did not want to hurt the cohesion of his team. But he and Mr. Thiel now had a setting in which to try out their ideas about diversity and meritocracy. “In the start-up crucible, performing is all that matters,” Mr. Sacks wrote about that time. He wanted to give all job applicants tests of cognitive ability, according to his colleague Keith Rabois, and when the company searched for a new chief executive, one of the requirements was an I.Q. of 160 — genius level. The goal was “pure meritocracy,” said Amy Klement, one of a small number of women to rise high within the organization. She and other women called Mr. Sacks an effective, relentless, generous boss. But some also wondered how comfortable the men running the company were around them. Lauri Schultheis said that when she interviewed to be PayPal’s office manager, and its first female employee — before even Mr. Sacks arrived — an engineer asked her, “Does this mean I have to stop looking at porn?” Photo PayPal had a hard time hiring women, Max Levchin, another co-founder, later told a class at Stanford, “because PayPal was just a bunch of nerds! They never talked to women. So how were they supposed to interact with and hire them?” “The notion that diversity in an early team is important or good is completely wrong,” he added. “The more diverse the early group, the harder it is for people to find common ground.” Later, in an interview, Mr. Levchin said he had been speaking about diversity of programming backgrounds, not race or gender. But intentionally or not, he stated something many people quietly believed: The same thing that made Silicon Valley phenomenally successful also kept it homogeneous, and start-ups had an almost inevitable like-with-like quality. The kind of common ground shared by the early PayPal leaders “is always the critical ingredient on the founding teams,” Mr. Thiel said in an interview. “You have these great friendships that were built over some period of time. Silicon Valley flows out of deep relationships that people have built. That’s the structural reality.” Later, well after Mr. Sacks, Mr. Thiel and their crew had weathered the dot-com crash, conquered the hackers, beaten the competitors, taken the company public and then sold PayPal to eBay in 2002 for a billion and a half dollars, Mr. Sacks called the company “the template for the modern Silicon Valley start-up.” Less than 10 years after graduation, he and Mr. Thiel had been transformed from outcasts into favorites with a reputation for seeing the future. Far from the only libertarians in Silicon Valley, they had finally found an environment that meshed perfectly with their desire for unfettered competition and freedom from constraints. The money they made seemed like vindication of their ideas. “Those who win get to rewrite the history,” said Fred Turner, a Stanford historian of technology. The success of the struggle to create PayPal, and its eventual sale price, gave the men a new power: the knowledge to create new companies and the ability to fund their own and one another’s. Billion-dollar start-ups had been rare. But in the next few years, the so-called PayPal Mafia went on to found seven companies that reached blockbuster scale, including YouTube, LinkedIn, Yelp and a business-messaging service called Yammer, founded by Mr. Sacks and sold a few years later to Microsoft for $1.2 billion. At the time of the sale, Yammer’s executive team was half female. The harshness of the Stanford Review crowd’s old arguments was largely forgotten; Mr. Rabois, who had once yelled the homophobic slur, and Mr. Thiel had come out as gay. Mr. Sacks said in an email that he was “embarrassed by some of the things I wrote in college over 20 years ago, and I am sorry I wrote them,” adding that he was “horrified” by his old views on homosexuality and that he calls himself a supporter of gay rights and marriage equality. “These views do not represent who I am or what I believe today,” he said. But Mr. Sacks did not entirely lose his touch for provocation. For his 40th birthday, just after the Yammer sale was announced, he threw himself a Marie Antoinette-themed bash, shipping cakes as invitations, hiring the rapper Snoop Dogg to perform, and appearing at the party in head-to-toe 18th-century French court dress.

The next chapter of Jessica DiLullo Herrin’s career unfolded in a kind of alternate Silicon Valley reality in which venture capital firms don’t figure much, like-minded women start companies together, and innovation unfurls on a new-mother-friendly schedule. She deliberately started low-key, driving around Texas in 2004 with a car full of wires and glass beads, asking friends to host “trunk shows” where they could make their own jewelry. (“It’s easy and rewarding to host a Luxe Jewels party,” her fliers said.) Her real goal was to update the direct-sales industry — like Mary Kay makeup or Tupperware parties, transformed for the Internet age. But she was also pregnant with her first child, so instead of relying on venture capitalists who would impose a firm timetable, she funded the new business with her own money and the revenue that began trickling in so no one else would control her schedule. (She later relied on investors to expand the company.) Jessica DiLullo Herrin, chief executive of Stella & Dot, in the walk-in closet of her home where she invites top sellers for an annual Champagne brunch. By Sean Patrick Farrell. Image by Max Whittaker for The New York Times. She let the project slow for a time after she gave birth and then picked it up again, eventually switching to premade costume jewelry. Once her second daughter, Tatum, reached 6 months old in late 2006, she recruited the rest of the initial team. “When we reached a million in revenue, I stopped breastfeeding,” she said. Her company was nearly as homogeneous as PayPal, stacked with female Stanford graduates interested in business and fashion. “O.K., who is in?” she asked her college girlfriends. At a Stanford reunion, she met a jewelry designer who became her partner, and they renamed the company after their grandmothers: Stella & Dot. But it was not precisely a Silicon Valley company. Ms. Herrin was giving sellers their own web pages and using Facebook to showcase goods, not trying to create a new device or software. “I’ve never tried to sit at the boys’ table,” she said. That may have been the safer bet. Of the tiny number of 1994 women who were starting and funding more technology-centric ventures, two were having a bruising time. Gina Bianchini had a sense of hustle and ambition similar to Ms. Herrin’s, also attended Stanford Business School, and also co-founded a company in 2004. Called Ning, it allowed people to create their own networks organized around specialized interests, like the “Twilight” franchise or working at I.B.M. Her co-founder was the Netscape founder Marc Andreessen, and together they took on over $100 million in funding. Ms. Bianchini was called a “Web 2.0 Hottie,” and Fortune featured her on the cover as one of “The New Valley Girls.” “She never, ever, would have founded a company about weddings,” said Kamy Wicoff, her classmate. But one day in 2010, her college friends got a text from her saying she was leaving unexpectedly, and soon Mr. Andreessen had sold the company. Some classmates whispered that she had only gotten the chance to co-found the company because the two had once dated — even though work and personal lives often overlapped in close-knit Silicon Valley. Photo Photo Photo Photo Another woman from the class of 1994 was quoted in the Fortune article: Trae Vassallo, who was Traci Neist when she built the taco-eating machine all those years ago, attended Stanford Business School with Ms. Herrin and Ms. Bianchini, co-founded a mobile device company, and then joined Kleiner Perkins, a premier venture capital firm. Ms. Vassallo did well, eventually playing key roles in two of its most successful deals of 2014, including the sale of Nest Labs, a maker of networked home alarms and other devices that was acquired by Google for $3.2 billion. But in early 2014, Ms. Vassallo was quietly let go. The firm was downsizing over all, especially in green technology, one of Ms. Vassallo’s specialties, and men were shown the exit as well. But in interviews, several former colleagues said it was far from an easy environment for women, with all-male outings and fierce internal competition for who got which board seat — meaning internal credit — for each company, not to mention a sexual discrimination lawsuit filed by a female junior partner, scheduled for trial in early 2015. They also said that Ms. Vassallo, earnest and so technical that she started a robotics program at a local girls’ school, had not been as forceful, or as adept a politician, as some of her male peers. If that was the case, the irony seemed cruel: She had just the kind of engineering background that everyone was always saying more women needed, but lost out, in effect, for being too much of a geek. Kleiner Perkins said that gender did not play a role in Ms. Vassallo’s departure and that 20 percent of its partners were women. “We very much value Trae’s contributions to the firm, and we continue to have a strong relationship with her,” a spokeswoman said. Ms. Vassallo declined to comment. Her departure became a source of frustration among women in her field. “A travesty,” Ann Miura-Ko, a fellow venture capitalist, called it in an interview. Since 1999, the number of female partners in venture capital has declined by nearly half, from 10 percent to 6 percent, according to a recent Babson College study. By that time, Ms. Herrin, Ms. Vassallo’s classmate, was getting ready to attend the 20-year reunion. She had annual sales of over $200 million in six countries; tens of thousands of stylists, to whom she had paid out hundreds of millions of dollars in commissions; and the beginning of an expansion into other products. Photo Her company could not rival the biggest ones founded by male classmates, and as with every direct-sales company, some women who signed on and failed to sell ended up with merchandise and no profit. But a few Stella & Dot sellers made hundreds of thousands of dollars a year. Every year, Ms. Herrin invited her top sellers to her mansion in the wealthy Silicon Valley town of Hillsborough, gathered them in the huge walk-in closet where her jewelry was displayed and clinked glasses in a Champagne toast.

The class of 1994 filtered back onto campus this fall amid the most intense round of founding and funding that Silicon Valley had ever seen, a new land grab to optimize seemingly every area of human endeavor, from getting pregnant to securing small-business loans. The atmosphere had been captured in a Twitter post by Mr. Sacks, who, after his classmate’s deal to sell WhatsApp was announced, proclaimed that payouts of less than $10 billion “just became quaint in Silicon Valley.” A Stanford entrepreneur was on the cover of Fortune again, with a company that promised to revolutionize blood tests. Women Studying Computer Science At Stanford, the number of women graduating with degrees in computer science fell sharply after 2001, but it has been rising in recent years. 70 60 50 40 Computer science graduate degrees earned by women 30 20 10 Undergraduate 1994 2001 2014 2009 As classmates started conversations with greetings like “How’s your fund?” some of those who did not work in technology joked that they felt like chumps. The Stanford campus had gone computer science crazy, with the majority of students taking programming courses. A career in technology didn’t feel like a risk anymore — it felt like a wise bet, said Jennifer Widom, a programming professor turned engineering dean. Computer science “is a degree that guarantees you a future, regardless of what form you decide to take it in,” she said. In terms of participation, current female students were still lagging behind men but doing more and better than the prior generation, with some starting companies while still in college. The founder on the cover of Fortune was a dropout poised to become one of the first women to start a technology company worth billions. The nature of start-ups was shifting again, too, this time largely in women’s favor. From servers onward, many components could be inexpensively licensed instead of custom-built. Founders could turn to a multiplying array of investment sources, meaning they no longer had to be supplicants at a handful of male-run venture firms. The promise that the Internet would be a leveler was finally becoming a bit more fulfilled. In fact, Jessica DiLullo Herrin had to watch her back: A young entrepreneur, who had put herself through Santa Clara University with direct sales of Cutco knives, had built what looked like an almost direct copy of Stella & Dot, called Chloe & Isabel, that was growing fast. Photo The frenzy had an unlikely effect on some members of the Stanford Review group: They were becoming cheerleaders for women in technology, not for ideological reasons, but for market-based ones. “Conservatives must acknowledge their role to expand the free labor market and kindle social progress by championing female technologists,” wrote Joe Lonsdale, another former Stanford Review editor and the co-founder of Palantir, a data analysis company, in The Review a week before the reunion. Like many others, he was finding that the biggest obstacle to starting new companies was a dearth of technical talent so severe they worried it would hinder innovation. “Everybody here has a huge incentive to get all the talented people we can, and that includes 50 percent of the population,” said Mr. Sacks, who a few weeks later joined and invested in a fast-growing start-up whose employees were 40 percent female, high by industry standards. The real surprise of the reunion weekend, however, was that more of the women in the class of ’94 were finally becoming entrepreneurs, later and on a smaller scale than many of the men, but founders nonetheless. Photo Photo The rhythms of their lives and the technology industry were finally clicking: Companies were becoming easier to start just as their children were becoming more self-sufficient, and they did not want to miss another chance. Their young companies matched technology companies with freelance legal talent; displayed art and photography on flat-screen televisions; and made electronic wristbands that enabled parents to keep track of children playing outdoors. Some of the female doctors in the class, ambitious yet risk-averse in their choices two decades ago, were taking the leap, too, founding companies that sold custom-blended vitamins online and helped monitor patients with chronic diseases. Dr. Dayna Long, a pediatrician, created a web-based screening tool to identify invisible factors that sapped patients’ health, like hunger and unsafe living conditions. When she pitched the idea to start-ups, requesting pro bono technical help, she was almost always the only black woman in the room. She was not an entrepreneur, but she had a vision for a new way to use technology, which she had persuaded hospitals across the Bay Area to adopt. As the reunion weekend drew to a close, Gina Bianchini sat down with Arielle Miller Levitan, the physician who co-founded the vitamin site, and a laptop to coach her on everything from font size to funding. Within a year of leaving Ning, Ms. Bianchini had started over, with her own company, named Mightybell. The way to prevail, she felt, was to be resilient, to risk failing twice, to pursue her years-old vision about connecting like-minded people and refine it until it was exactly right. “Silicon Valley loves redemption. So do I,” she said.