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Where is the Female Mark Zuckerberg?

E.B. Boyd | November 22, 2011 | Story Profiles News and Features Tech World

One wintry Boston evening in 2008, Leah Busque and her husband, kevin, were meeting friends for dinner when they realized they were out of kibble for kobe, their yellow lab. The cab was on its way, and stores would be closed by the time they got home. “Kevin said, ‘Wouldn’t it be nice if there were a place online where we could say we needed dog food, name the price we’d be willing to pay, and see if there was someone in our neighbor- hood who would be willing to help us out?’” recalls busque, a sunny brunette whose mama-bear warmth belies a tenacious drive. They looked at each other and instantly knew: That’s it.

“We had been talking a lot about what I wanted to do next in my career,” says Busque, 32, a programmer at IBM at the time but an entrepreneur and CEO at heart. (Her first “company,” Pollution Solutions, involved ordering her sister and cousin around as they handed out flyers on recycling. She was eight.) By the time the cab arrived, she’d whipped out her iPhone and grabbed a domain. Over margaritas, she and Kevin, her high school sweetheart and a programmer at a health care startup, brainstormed how the service would work.
Nearly four years later, TaskRabbit—a site that helps you get “just about anything done by safe, reliable, awesome people”—has taken off with a speed that has everything to do with the Great Recession and the ways that social networks are creating new forms of commerce. There are hordes of underemployed potential Rabbits looking for income and legions of frantically overworked beavers yearning for relief. “People use it for all kinds of things,” Busque says: picking up prescriptions, posting stuff for sale on Craigslist, standing in line at the DMV, driving Grandma to a wedding. One guy wanted help selecting his Fantasy Football team. Another needed someone to write a letter to his ex-girlfriend to convince her to come back to him. One of the most common tasks? “Set up my Ikea furniture.”
The service is now up and running in six cities, including Boston, New York, and San Francisco, where the Busques moved last year. By this November, more than 2,000 people had signed up to be Rabbits, and though the company won’t disclose how many tasks have been completed, it does say that the number has tripled since it closed its $5 million in Series A financing in March (total funding approaches $7 million). The site is logging about $4 million in transactions every month.
Busque tells me TaskRabbit’s story while giving me a tour of the company’s new digs near South Park. They’re cavernous, furnished with long tables and gigantic monitors and exuding an anticipatory, optimistic vibe. (At the moment, the company employs a staff of 35, but Sean Flynn, a Shasta Ventures partner who led the latest funding round, tells me, with just a touch of VC hyperbole, that it could be “as big as eBay.”) As Kobe (“chief inspiration officer”) pads alongside us, Busque points out the standard startup features: a kitchen stocked with treats, a conference room–playroom complete with ping-pong table and large-screen TV— even the scuff marks on the floor where walls have been knocked down (the previous inhabitants were lawyers) to create one open, democratic space.
What she doesn’t point out is that she herself embodies a new trend in the startup world, the female entrepreneur. “I never really gave it much thought,” Busque says. She’s an alum of all-female Sweet Briar College in Virginia, where she studied math and computer science. “Spending four years surrounded by other really smart women who were into technology, it never occurred to me that this wasn’t what I was supposed to be doing.”
As I move through Silicon Valley, I meet more and more women like Busque—former programmers, MBAs, and even designers who are launching their own companies. The trend is in stark contrast to the industry’s prevailing narrative. Four decades into the tech revolution, people are still chafing at the fact that there are so few women in the industry, that the typical startup involves a handful of brash young guys and the occasional geekette. The excuses haven’t changed much, either: Women are risk-averse. Women aren’t technical. Women can’t figure out the work-family balance. VCs are so besotted with male Harvard and Stanford drop- outs that they barely give brilliant female entrepreneurs the time of day.
And yet in the New Boom reshaping Silicon Valley, the old paradigms—gender and otherwise—are rapidly shifting. Not only are there more female founders than ever before, but for the first time in tech history, women founders in certain types of businesses actually have an edge over their male peers. It’s a striking development, but one that’s received remarkably little fanfare for an industry addicted to its own hype. Young female entrepreneurs don’t seem eager to trumpet what’s happening—blame millennial nonchalance, or post- feminist ambivalence, or the simple reality that being a pioneer isn’t something they think about day to day. As for the rest of the Valley—maybe it’s just so steeped in the idea that startup success requires an XY chromosome that it can’t see what’s happening right under its nose.
Silicon Valley has always had its female entrepreneurs—think Sandy Lerner, who cofounded Cisco, and Diane Greene, whose server software company, VMware, was worth a reported $10 billion when she took it public in 2007. But they’ve been rare birds, and largely unsung. In the Valley, a woman’s place is much more likely to be in marketing or HR.
Now, for the first time, there are so many women starting their own tech companies that you could easily use up all of your fingers and toes, and those of several other people, counting them. Last year, Women 2.0’s annual list of “Female Founder Successes” included an impressive 134 names. “When we started, the discussion about women entrepreneurs in technology wasn’t even happening,” says Shaherose Charania, a former telecommunications product manager who cofounded the organization five years ago. She recalls an early meeting with a group of women executives and programmers working at places like Google. “They were just talking about wanting to start companies. Now half of them are doing it.”
This boom within a boom began with the evolution of technology itself. “You don’t have to be an engineer to found a company anymore,” says Floodgate Fund’s superangel investor Ann Miura-Ko (aka “the most pow- erful woman in startups”). “You [just] have to have a really compelling narrative that will attract top-notch engineers and talent to your vision.” Success today is based on “your fundamental market insight,” she adds. “The technology field has been fairly leveled.”
It’s impossible to overstate the importance of this development for the New Boom in general and for women in particular, who account for just 18 percent of undergraduate engineering degrees and 22 percent of computer science degrees. Fifteen years ago, most tech startups were focused on some kind of core technology: faster chips, new kinds of storage, more powerful databases. Ten years ago, launching an Internet company still required a certain degree of technical mastery just to keep the servers humming and the algorithms cutting-edge. Now Amazon leases space on its massive server farms, eliminating two of the biggest barriers to entry in the field: the need for infrastructure and the money to pay for it. Companies like Facebook aren’t tech plays in the traditional sense—they’re great businesses built on existing technology. Today, if you have a good idea for a website or phone app, even the coding can be outsourced.

Meanwhile, startup costs have become so minimal—as little as $25,000—that you can raise what you need by maxing out a credit card. Instead of holing up in the proverbial garage, you can open your laptop wherever you happen to be—your apartment, Ritual Roasters, your parents’ house over the holidays—and launch. In Busque’s case, it was a spare bedroom in her house in Boston. Four months after coming up with the idea for TaskRabbit, she quit IBM. “I had never built web applications before,” she says. “But I thought, ‘This isn’t rocket science. This is what I do.’ ” She taught herself Ruby on Rails, a programming framework for the web, and ten weeks later, she had coded the first prototype.
Beyond technology, there’s the evolution in women’s social and business networks. Despite the college dropout–turned–tech genius trope, the vast majority of male founders work their way up inside existing companies, gaining experience, refining ideas, and making valuable connections before setting out on their own. The dot-com boom of the 1990s provided a path for women to do the same; many of the current crop of female founders did time at places like Yahoo!, eBay, and Google.
The connections matter immensely for women, who historically have had difficulty accessing the financial and business networks that make Silicon Valley run. “It’s still uncomfortable for men and women to do business with each other sometimes,” says Sharon Vosmek, CEO of Astia, a San Francisco–based not-for-profit that provides training, networking, and support for female tech entrepreneurs. “Most venture capitalists do investing in very intimate settings. If I go to have beers with a guy, I’m OK with it, but I happen to live in a marriage where that doesn’t cause problems.” The Mission or Palo Alto of 2011 is hardly iMad Men. But the reality is that a 25-year-old woman still can’t invite out a 40-year- old man to pick his brain and cultivate a professional relationship as easily as a 25-year-old guy can.
The arrival of Sheryl Sandberg at Facebook in 2008 was another milestone. When she was still at Google, Sandberg began inviting women to her house for monthly get-togethers, something very few other high- ranking Silicon Valley woman had done. “It’s encouraged the expectation that you give help and that other people help you,” says Gina Bianchini, cofounder (with Marc Andreesen) of the social media site Ning and founder of Mightybell, a new social network designed to help people achieve their goals.
Organizations like Women 2.0, Astia, and the Founders Institute are also playing an important role, and the focus on networking is paying off big-time. Veteran Googler Sukhinder Singh Cassidy met Accel Partners’ Theresia Gouw Ranzetta during the dot-com era, and they stayed in touch, bonding over shared life experiences like getting married and having kids. When Singh Cassidy decided to launch Joyus, which helps businesses sell their wares using video, Gouw Ranzetta was one of the first people she called. Similarly, when longtime retail executive Susan Feldman was looking for a partner to start One Kings Lane, BlogHer cofounder Lisa Stone connected her with Alison Pincus, a digital marketing and business development executive (and wife of Zynga’s Mark Pincus), who became Feldman’s cofounder and chief strategy officer.
Equally promising has been the erosion of the invisible barriers to cross-gender networking. “The people who have helped me the most are men my age or younger,” says Mariam Naficy, cofounder of Minted, which is revolutionizing the stationery industry. Naficy, 41, scored a solid hit a decade ago with, an e-commerce beauty-industry pioneer that sold for a reported $100 million. When it came time to launch Minted, she reached out to her whole network, men as well as women. As a result, her funders included several male classmates from Stanford Business School; a male VC she’d gotten to know socially; Jeremy Stoppelman of Yelp; and Google’s Marissa Mayer, whom she’d met through Minted’s chief technology officer, Niniane Wang.
At TaskRabbit, Busque’s personal and networking skills have proved every bit as important to the company’s success as her technical prowess. Early on, when she wasn’t coding, she donned the CEO hat and sought advice from technologists, entrepreneurs, and investors—anyone who might be able to help—while her husband stayed in the background, working part-time on the infrastructure and holding down his day job. “Leah’s a very dynamic and outgoing person,” Kevin Busque says. “It was clear from day one that she was going to be the face of the company and that I was going to be the person to support her.”
Among those she cold-emailed was Scott Griffith, CEO of Cambridge, Mass.–based Zipcar, which was founded by two women—a fact that has made him both particularly sensitive to the challenges faced by female founders and unusually willing to serve as a mentor. Griffith was so impressed by Busque (he calls her “a force of nature...born to be an entrepreneur”) that he let her work out of Zipcar’s offices for a year. “I thought, ‘If she’s going to really succeed, let’s give her all the help we can.’” It was Griffith and his gang who put Busque onto Facebook’s fledgeling fbFund, an incubator to support social-media startups, which selected TaskRabbit for its inaugural class. After flying out to work with the fund that summer, Leah decided the Bay Area was where her company needed to be. “The culture here is so supportive of innovation and new ideas,” she says. “You go out to a coffee shop, and everyone’s talking about technology and startups and the latest widget that they’re building. This just felt like home.”
But technoLogy and networking are only part of the story, as Aileen Lee, a partner at Kleiner Perkins Caufield & Byers, spelled out in a much-read TechCrunch post this past March, “Why Women Rule the Internet.” More women than men use social networking sites, which play a powerful role in creating word of mouth for new Internet companies, Lee wrote. And when it comes to buying stuff online, women shop more and shell out more cash. “A lot of companies that are growing really fast are built on insight into the female consumer as the target customer,” she tells me. Indeed, there’s so much focus on tapping the female market that several people interviewed for this story confided that they regularly get calls from male entrepreneurs looking for women to help get their companies off the ground.
But more and more women have their own great business ideas to occupy them—entrepreneurs like Megan Gardner of Plum District, a daily deals site aimed at moms; Mauria Finley of Citrus Lane, which sends care packages to new parents; and Jessica Herrin of Stella & Dot, which is reinventing the direct-sales jewelry industry. Floodgate’s Miura-Ko recalls the day in 2009 when Susan Gregg Koger came in to pitch ModCloth, a new model for indie fashion. The same day, two men presented an idea for another fashion startup— providing technology to magazines and designers to create slick lookbooks, or fashion portfolios, to view on the iPhone. “I asked one of them if he was really interested in fashion,” Miura-Ko says. “He said it wasn’t necessarily a personal passion; the iPhone was. But if you ask Susan what she does in her free time, she’s been vintage clothing shopping since she was 13.” Miura-Ko said yes to Koger and no to the guys.
Investors like Miura-Ko are salivating because there are huge fortunes to be made on the right bet. Gilt Groupe, the women-founded New York company that started the flash-sale craze, is reportedly valued at $1 billion. The stationery industry that Minted is diving into is worth $10 billion; the baby space that Citrus Lane is targeting, in the low $30 billions. Ironically, the trend toward female-founded and -focused sites is so strong that it’s triggered a backlash. During this fall’s DEMO conference, where many startups make their debut, one journalist tweeted her impatience at what some are calling a pink-collar tech ghetto—“Women: Stop making startups about fashion, shopping, & babies. At least for the next few years. You’re embarrassing me.”
This, in turn, provoked vociferous pushback from the likes of Tara Hunt, a serial entrepreneur who moved from San Francisco to Montreal two years ago and cofounded Buyosphere, a shopping site that lets people create “taste profiles” based on what they’ve done online (everything from their previous purchases to their tweets). Women need to cut each other more slack, she blogged. “Shopping = bad. Fashion = bad. Babies = bad. are a man.” She amplifies her point in a Skype conversation from Poland, where she’s been invited to judge a startup competition. “If a man enters a feminine space, then you can take the space seriously,” she says—pointing to such male-founded shopping megasuccesses as,, Amazon, Bluefly, Kaboodle, and eBay—“but if a woman enters it, it’s not taken seriously.” She sees the debate as a reflection of how hard women have had to work to gain any foothold in the tech world and also of women’s tendency to second-guess. “We’ve been begging and screaming to get included, and then we show up in high heels talking about designer snugglies and nail polish. Damn these women being all women-y talking about women stuff!”
Meanwhile, the “pink collar” brouhaha misses the bigger picture: an impressive array of women-founded startups that have nothing remotely girlie about them. Laura Mather, a former eBay executive, launched Silver Tail Systems to develop cutting-edge fraud-detection tools. UpMo, created by BEA Systems alum Promise Phelon, is building tools to help companies retain employees. SlideShare, a presentation-sharing site, is the brainchild of Rashmi Sinha, a designer with a doctorate in cognitive psychology.
Part of TaskRabbit’s genius is that it straddles the male-female divide. It didn’t start out as a company expressly aimed at women. But it turns out that overextended professional women are among its core customers—and underextended, formerly professional ones among its many wannabe Rabbits. The company also sees a potential market in helping businesses outsource mundane jobs and errands; investor Sean Flynn expects it to become an eBay for any kind of service you’d normally find listed in the Yellow Pages. “We made this investment because we think it has the potential to be a multibillion-dollar company,” he says.
So much for the glass-half-full view. The glass-half-empty contingent takes head counts at tech conferences and scrolls through the websites of the VC giants and wonders: If conditions are so ripe for female entrepreneurs, why aren’t there more? It’s possible that the actual percentage of women founders hasn’t risen much in the past five years, suggests Vivek Wadhwa, who teaches entrepreneurship at UC Berkeley, Duke University, and Harvard Law School. “Overall, entre- preneurship in tech has increased dramatically because it has become so much easier and cheaper. But proportionally speaking, I’m not convinced that women are doing more than they were doing before.”
When I put the question to Dave McClure, founder of the hot Mountain View incubator 500 Startups and one of the executives turned investors who make up the PayPal Mafia, he draws an analogy to girls’ soccer. Title IX passed in 1972, but it wasn’t until 1999, when the U.S. team won the women’s World Cup, that large numbers of little girls started trading in their ballet slippers for soccer cleats, he says. “After the World Cup, you had a lot more heroes.”
The tech equivalent of a Mia Hamm or Brandi Chastain, McClure says, would be a woman with the iconic status of Facebook’s founder—a female Mark Zuckerberg. I ask McClure how far along that progression we are. Given everything I’ve seen in Silicon Valley, I’m thinking he’ll say, “Pretty close.” Instead, he looks apologetic and responds, “Maybe halfway?”
In part, it’s a numbers problem, says Janice Fraser, cofounder of Adaptive Path, a design consultancy that works with many of the Valley’s most innovative companies, who now runs her own incubator, LUXr, advising a new generation of startups. “We haven’t had the one in a million because we haven’t had the million.” And for that to happen, deeply rooted systemic problems need to be addressed. “At every stage, a female CEO has to be supported by her board,” Fraser says. (She’d rather not get specific.) "As they approach investment banks and prepare to do a road show”—in advance of an IPO—“the investment banks have to be prepared to take that female CEO seriously. There can’t be any last-minute quarterbacking and switching out of that woman for someone who might be better received on Wall Street.”
One of the biggest hurdles facing women entrepreneurs is their lack of access to capital, which in turn is largely a function of something called “pattern recognition”—one of the basic methods used by VCs and angels to evaluate where to place their bets. “Venture capitalists look for examples of prior success in the entrepreneurs they want to back,” says Ethan Kurzweil, an investor with Bessemer Venture Partners who participated in a panel on female tech founders at this year’s South by Southwest conference. “If they’re looking for the next Mark Zuckerberg, well, Mark Zuckerberg is a man.”
It isn’t just Zuckerberg’s gender, of course; male VCs (and 9 in 10 of them are male) look at all sorts of behavioral clues that they believe will signal whether an entrepreneur will have the tenacity, agility, and smarts to weather the long, lonely years of forging a business. Since men and women often have markedly different ways of presenting themselves, many investors interpret the absence of certain behaviors as a sign that a woman doesn’t have what it takes. “One investor told me, ‘I can’t figure you out,’ ” says Rebecca Woodcock, cofounder of Cake Health, a medical expenses management tool that was a finalist at this year’s TechCrunch Disrupt conference. “He said, ‘Most entrepreneurs are aggressive and pushy.’” Woodcock, in contrast, is one of the quietest people I’ve ever met in Silicon Valley. “He was confused,” she says.
Women will eventually overcome these subtle, subconscious biases, predicts Berkeley/Duke/ Harvard’s Wadhwa, noting that Indian and other Asian engineers faced the same challenge 30 years ago. The tech industry happily welcomed Asians onto its engineering teams, but balked at giving them other roles. Says Wadhwa, himself a former entrepreneur, “I was told my people don’t make good CEOs.”
Indians had to turn to their own communities for funding. Today, given the track record of people like Sun Microsystems cofounder turned VC giant Vinod Kholsa, Sand Hill Road is no more likely to automatically turn away an Asian entrepreneur than it is to slam the door on a hoodie-wearing nerd from Carnegie Mellon. “But that happened over a period of two decades,” Wadhwa points out. Women, he estimates, are only a few years into their own two-decade cycle. “In the next five years, we finally will have some very significant women who have risen very high and achieved success— they’ll provide role models for other women.”
At the moment, the woman to watch is Facebook’s Sheryl Sandberg. A year ago, at a TED conference on women’s issues, Sandberg gave a 15-minute talk, “Why We Have Too Few Women Leaders,” that instantly went viral. Sandberg didn’t focus on external barriers; instead, she talked about the ways in which women in all industries unintentionally hold themselves back. They don’t “sit at the table,” she said. They don’t assert themselves, they don’t negotiate for the things they want, and they don’t give themselves credit for what they’ve achieved.
Women also start “leaning back” at work in anticipation of eventually taking time off to have children. Long before they’re pregnant, they stop pushing for promotions or plum assignments, making it more likely that they won’t have a job worth coming back to. Sandberg admonished women to keep asking for as much as they want until the day they go on maternity leave. “Don’t leave before you leave” has become a rallying cry for women throughout Silicon Valley.
Earlier this year, Caroline O’Connor was a fellow at Stanford’s Hasso Plattner Institute of Design (commonly referred to as the After winning a slot in the school’s coveted Launchpad class, in which students take an idea from zero to launch in 10 weeks, with the implicit understanding that if the idea gains traction, they will turn it into an actual business, she learned that she was pregnant.
“My initial response was, ‘I’m obviously going to drop this class because there’s no way it’s going to work out,’” O’Connor, 36, says. But when she informed Sarah Stein Greenberg, the’s managing director, Greenberg told her, “You have to watch this TED talk.”
“Her perspective was that I had seven months ahead of me,” O’Connor says. “Why would I back away from the class when I had so much time?” Sandberg’s speech changed O’Connor’s mind. This summer, O’Connor and a partner launched Plum Gear, a “Netflix for baby clothes” that eases the strain on new parents’ wallets by allowing them to borrow items instead of buying. In October, the business got a write-up in the Wall Street Journal—17 days before O’Connor gave birth. “Sheryl’s talk really upended my point of view on what the next few years of my life could be like,” O’Connor says. “If I had backed away, I probably would have regretted it forever.”

One evening this fall, Taskrabbit and Eventbrite, the online ticketing service, cohost a party at a SoMa loft to launch “Do More. Live More. Be More,” TaskRabbit’s new marketing campaign. The wine is flowing freely, and twentysomethings in company T-shirts flit about excitedly, checking their iPhones every 10 seconds. When the companies’ founders take their place at the front of the room, though, it suddenly feels less like a typical New Boom party and more like a premonition. Instead of two guys in designer jeans and expensive button-downs addressing the crowd, it’s Busque, who’s a quarter inch short of five feet tall, and Julia Hartz, Eventbrite’s cofounder, who sports a striped tee, navy jacket, and six-months- pregnant belly.
Watching Busque reminds me of McClure’s prediction that the tipping point for women will come when there’s a female Mark Zuckerberg. I suddenly wonder whether Busque could be the one. She’s got the tech credentials. She’s got the business acumen. Her company could one day be worth billions, in which case she could become a household name—at least in SoMa and Palo Alto.
A couple of weeks later, however, I get a call from TaskRabbit’s marketing manager. She tells me the company is hiring a new CEO. Busque is moving into a chief of products role while the top slot goes to Eric Grosse, Hotwire’s founder and Expedia Worldwide’s former president. The company needs to scale quickly, the marketing manager explains, and Grosse has the experience to make it happen.
Now I think about Janice Fraser’s warning— how danger lurks for a woman founder at each stage of a company’s growth, how at any moment investors could decide to replace her. But I’m puzzled about this particular switch. When I asked Sean Flynn whether he thought Busque could go all the way, he assured me the answer was yes.
I pick up the phone, expecting to get a dejected Busque on the other end. But instead, she’s as chipper as ever, explaining that bringing Grosse on was her idea. “I went to my board about five months ago and said I think we need to bring on some executive leadership,” she tells me. With the company gaining momentum and opening up in new cities—and with competitors like Second Life’s Philip Rosedale jumping into the same space—Busque wanted to bring someone on board who could take TaskRabbit from promising startup to the powerhouse Sean Flynn has envisioned.
“I wasn’t set on the specific role or title of the person I wanted to bring in,” Busque continues. “The whole goal was to find someone with complementary skills to mine.” When they found Grosse, with his experience in growing and managing large travel sites, she knew he was the one.
Fine, I say, but why cede the top slot? When Zuckerberg needed that kind of help, he didn’t step down; he brought in Sandberg as his number two. Why not do the same with Grosse?
Busque responds that given Grosse’s credentials, asking him to come in below her would have been “weird.” Holding on to the CEO job “comes down to ego,” she says. “This is about me finding a partner to help me realize a vision for the company. My involvement will be no less. I think the hardest part about being an entrepreneur is being able to make these tough decisions about what a company needs and doing what’s best for the company.”
At first, I’m struck by Busque’s maturity. In an industry where there’s no greater hero than the founder-CEO, she’s willing to step aside in the service of her larger vision. This seems admirable—until I remember Sandberg’s TED talk. Could what someone like Busque sees as “ego” be what someone like Sandberg (or a man) sees as “sitting at the table”?
I run the idea by Sharon Vosmek of Astia, since keeping women in leadership roles is one of her organization’s goals. “We’re breeding young women to not measure their skill sets in the same way that men measure theirs,” she says. “Women self-assess differently than men, and therefore they aspire differently.”
Vosmek tells me a story about one of Astia’s applicants. “She had run a successful hedge fund for 15 years. She had developed a platform for trading for hedge funds. It was a fantastic market opportunity.” But the woman said she wanted to bring in someone else as CEO. “She completely discounted her experience,” Vosmek says. “She said, ‘I don’t know if I could deliver on it because I’ve never been an entrepreneur before.’ One of our advisers replied, ‘You have all the right relationships in this industry. You have 15 years of experience. If you couldn’t deliver on it, who could?’”
When I look around, I begin to see examples everywhere of what Vosmek is talking about. Gilt Groupe’s founders have stepped aside to bring in a new, male CEO. So have One Kings Lane’s power couple, Feldman and Pincus, and Laura Mather of Silver Tail. When I ask why, Mather says that she doesn’t have any experience running a company and that it will be a great opportunity to learn from someone who knows the ropes.
Which again sounds entirely reasonable, until you look at a place like, a six-year-old company that’s giving Microsoft a run for its money in the file-storage and -sharing business. It has raised a whopping $162 million and counts a large chunk of the Fortune 500 among its customers. Sitting at the helm is 26-year-old Aaron Levie, who launched the company out of a USC dorm.
Levie is impressive, but no more so than Busque, nor does he have more experience tackling the kind of massive scaling challenges now in front of him. But when I ask him if he would voluntarily cede the CEO slot, he demurs. “I’ve always wanted to build companies,” he tells me. “The best way to keep me super excited is to keep me in the driver’s seat.”
Janice Fraser, as it happens, is an adviser to TaskRabbit. She declines to talk directly about the company, citing confidentiality agreements. But she puts a new twist on Busque’s decision. “This kind of thing happens a lot,” she says. “At a certain point in a company’s growth, it can make sense for the founder, irrespective of whether they’re male or female, to shift over to a product role and bring in the ‘We can make this a super-huge company’ kind of CEO.” But whether women are more likely to do that than men is unclear, given the small sample size. “If we had 20,000 women-founded startups, then we could look at the data,” Fraser says. “Until we have sufficient numbers, we’re not going to really be able to know what the patterns, and the differences, are.”
The challenge is to get the numbers to that level. Of course, at that point the need to understand the factors that encourage or deter women entrepreneurs will be far less urgent. The current mini-boom could be the chicken— or the egg. Says Bessemer’s Kurzweil, “Investors in today’s companies are having their minds opened to the fact that women can create new forms of e-commerce.” As VCs and angels dig into their pockets, they create new role models for female founders to emulate— which in turn leads to new patterns for investors to glom onto. “That’s how this problem will be tackled over time.”

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E.B. Boyd covers Silicon Valley for


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