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Originally published Thursday, June 7, 2012 at 5:30 AM

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Bachelorville's big fish

Mark Zuckerberg is now taken, but Silicon Valley's dating pool is still well stocked with eligible singles.

The New York Times

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When Mark Zuckerberg of Facebook married his longtime girlfriend, Priscilla Chan, recently, one of the world's youngest billionaires was off the market.

But that doesn't mean that there is a dearth of eligible singles in Silicon Valley.

Perhaps nowhere on earth are there more young, bright, wildly overcompensated hyper-achievers who are currently unattached. The Facebook initial public offering alone spawned, by some estimates, 1,000 millionaires (never mind that $1 million these days barely buys a ranch house in Palo Alto, Calif.). And every year, the pool grows, as a new crop of kids arrives from Stanford and Harvard, fueled by Mountain Dew caffeine and IPO dreams.

But with everyone in a sprint to make their killing before the next crop of dreamers arrives to take their place, many find it hard to find time for dating. Faced with 16-hour workdays, it is hard enough to find time to shave.

Part of the reason for the glut of singles is demographic. For all the inroads that female power brokers like Marissa Mayer of Google or Sheryl Sandberg of Facebook have made, the upper echelon of the tech world remains largely a male domain. Of the American startup tech firms with venture capital backing, for example, only about 11 percent had female chief executives or founders as of 2009, according to Dow Jones VentureSource data, cited in The Wall Street Journal in 2010. (The industry's gender imbalance also lurks at the core of the recent high-profile sexual-discrimination lawsuit by Ellen Pao, a female junior partner, against her employer, the venture capital firm Kleiner Perkins Caufield & Byers).

The imbalance is also painfully clear to the male tech executives in the Santa Clara Valley, who bitterly joke about living in "Man Jose" or "Manta Clara."

For women, "the ratio certainly can work in your favor," said Julia Allison, a former tech journalist who divides her time between New York and the Bay Area, and says she finds digital entrepreneurs more satisfying partners than Wall Street moguls: "Wouldn't you rather be with someone who was changing the world?"

Unlike Hollywood, or even New York, Silicon Valley is not a nightclub culture. People talk work even for fun in their supposed off-hours, trading industry gossip in low-key spots like Philz Coffee or the Old Pro, a sports bar, in Palo Alto, said Amy Andersen, who runs Linx Dating, a Menlo Park-based dating and social network that caters to high-earning tech executives. It's an insular world. "Silicon Valley connections — whether they are for business, love, or friendships — occur from trusted sources," she said.

The following is an admittedly unscientific roundup of some of the unmarried tech executives who inspire the most buzz in Silicon Valley and its East Coast counterpart, Silicon Alley. At this point, it's still mostly men who have a net worth in eight or nine figures, although that could change in the next few years as a generation of hard-charging single women in their 20s (Alexa Hirschfeld of Paperless Post, Hayley Barna from Birchbox or Melody McCloskey from StyleSeat) begin to make their move.

Pete Cashmore, chief executive, Mashable

Inc. magazine tagged Cashmore — 26 and with a net worth estimated as high as $95 million — as "the Brad Pitt of the blogosphere." Gawker called him "the planet's sexiest geek." He currently sees Lisa Bettany, a photographer and entrepreneur. And like a matinee idol, he has a sultry air that has even become an in-joke among techies. An anonymous Twitter account called @hotpetecashmore is dotted with tweets like "Am I the only one feeling hot, hot, hot tonight? — Pete." But Cashmore did not make it on his looks. He started Mashable in his bedroom in Aberdeen, Scotland, at age 19, and for a time some tech insiders joked that he was the "Loch Ness Blogger," because so few in tech circles had actually laid eyes on him. Those days are over. Mashable now attracts more than 20 million visitors a month, and this year, Cashmore made Time's list of the 100 most influential people, as well as the Forbes "30 Under 30" list.

Matt Cohler, Facebook employee No. 7, now general partner at Benchmark Capital

Since Cohler, now 35, struck out trying to make it as a saxophonist, the Manhattan-raised Yalie has been on a winning streak. He was one of the first employees at LinkedIn and then at Facebook. (His Facebook shares were valued at a reported $680 million before that stock's slide.) As he said, "I am very aware that I'm one of the luckiest people who ever lived." Except — so far — in love. Last year, he and his longtime girlfriend broke up, and he now finds himself looking for company in the brownstone that he recently bought in downtown Manhattan, which he has decorated with works by Richard Avedon and Vienna Secession-period furniture.

Jack Dorsey, co-founder, Twitter and Square

Dorsey, 36, has gone from bike messenger to Internet superstar, net worth estimated at $650 million, all on the strength of a simple idea that turned out to be one of the most intoxicating time-sucks since television. Along with money came the trappings of fame: the Prada suits, the A-list friends (Ashton Kutcher, Alyssa Milano), the long Vanity Fair profile last year — and even hints that he is eyeing a political future. Dorsey tends to keep his romance private, although he did discuss a recent relationship with Sofiane Sylve, a principal dancer with the San Francisco Ballet, in that Vanity Fair article. "I've learned a lot from ballet," he was quoted as saying. "I appreciate the coordination and the discipline. Making something simple is very difficult."

Larry Ellison, chief executive, Oracle

At 67, Ellison might not fit everyone's definition of "eligible." But since his fourth marriage — to Melanie Craft, a romance novelist a quarter-century his junior — ended in 2010, the tech pioneer (estimated net worth: $36 billion) is back on the market. Ellison is one of the Valley's biggest personalities (Mike Wilson's 1997 biography of him was titled "The Difference between God and Larry Ellison"), one who has invested hundreds of millions of dollars in a yacht-racing team and scored an America's Cup victory in 2010, and few think he will be out of the dating game for long.

Tony Hsieh, chief executive, Zappos.com

Like Mark Zuckerberg, Hsieh went to Harvard and favors hoodies. Like Zuck, he also made a fortune at a very young age (at 24, he sold a company he co-founded to Microsoft for $265 million) then an even bigger one later (in 2009, Amazon snatched up Zappos for more than $1 billion). The value of his stock has been estimated at more than half a billion dollars, plus he has a colorful-enough personality to keep things interesting. In press interviews, the 38-year-old founder of the online shoe and clothing retailer has openly discussed his interest in pickup-artist books like "The Game," by Neil Strauss. "I don't use the term 'dating,' " he explained in a recent email. "My current philosophy is to not look at things as black and white," he said, "but instead to just enjoy hanging out with different people." But marriage may not be in his future: "I'm not opposed to the idea of marriage. But statistically, if half of all marriages end in divorce, and of the ones that remain married many are unhappily married, the odds are stacked against you."

Salar Kamangar, senior vice president, YouTube

When a network dating show recently approached Kamangar to appear as a contestant, it didn't get far. Kamangar is as private as he is eligible. But you can understand the network's interest. Kamangar, 35, joined the early team at Google as a gofer and now runs one of the most popular Web properties on the planet. The Tehran-born executive, who studied biology at Stanford, took over YouTube in 2010, after playing a key role in developing AdWords, the advertising system that has generates most of Google's revenues. (A 2006 article in BusinessWeek read, "It's safe to say that without Kamangar, Google wouldn't be Google"). As for romance, Gawker ran an item a few years ago linking him to Ivanka Trump, before she was with Jared Kushner of The New York Observer. But it would have never lasted. He's far too press-shy to be a Trump.

Aaron Levie, co-founder, Box

Many Silicon Valley observers consider the cloud-computing storage company that Levie and his partner, Dylan Smith, conceived in Levie's University of Southern California dorm room as a potential Next Big Thing. At 27, Levie has already taken a page from the Steve Jobs playbook. Last September, he played ringmaster at the company's first conference, BoxWorks, showing up in orange sneakers and firing up a crowd of hundreds with motivational pronouncements before handing out free Motorola XOOM tablets for everyone, Oprah-style, and giving over the stage to Third Eye Blind. While Levie, who has a longtime girlfriend, hasn't made an enormous killing yet, many Silicon Valley observers consider it just a matter of time. Recently, Box reportedly turned down a buyout offer exceeding $500 million.

Matt Mullenweg, founder, Wordpress and Automattic

Mullenweg, who moved to the Bay Area after attending the University of Houston, made a fortune in the early days of blogging by giving future bloggers the tools they needed to chase their online dreams: in this case, WordPress, the open-source content management system used by nearly 15 percent of the top million websites worldwide. Still only 28, the boyish blond with the snowboarder stubble is now worth an estimated $40 million. An unreconstructed geek, he types on a Dvorak computer keyboard (as opposed to the traditional, yet less intuitive, qwerty typewriter layout) to speed up his fingers. Does the time saved leave more hours for dating? Mullenweg remains coy on the subject. "I'm not engaged or married," he wrote in an email. "Most entrepreneurs, myself included, are married to their work, though."

BEN RATTRAY, CO-FOUNDER AND CHIEF EXECUTIVE, CHANGE.ORG

At 31, Rattray still drives a 1996 Toyota Camry and shares a cramped Noe Valley apartment in San Francisco with three college buddies. But the Matthew Fox look-alike is perhaps the tech world's comeliest crusader. He is the rare Silicon Valley entrepreneur who deliberately left the fast-money track to start a tech company. His epiphany came as an undergraduate at Stanford, where he had his sights on investment banking. His younger brother had come out as gay and described the discrimination he faced, so Rattray decided to make a difference instead of a fortune. His idea, Change.org, is a company that provides a platform for people to start online petitions to promote social change. The Washington Post singled out Change.org as "one of the most influential channels for activism in the country," and its success has landed Rattray on the Time list of the 100 most influential people, as well as appearances on programs like "The Daily Show." After a recent appearance, one young Chicago woman tweeted: "New crush: Ben Rattray, founder of http://change.org. He exists at the beautiful intersection of activism and stubble."

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