Entrepreneur

How to succeed in the ‘old boys club’ of venture capital

Above: Debbie Wosskow, CEO of Love Home Swap

This story originally ran in the Daily Telegraph‘s Wonder Women section.

As a tech reporter, I hear from female founders in Silicon Valley and its British equivalent, “Silicon Roundabout,” that it’s an ongoing challenge to fund a business, hire talent, and gain the respect of male peers.

Also at play, they say, are the shortage of female mentors and that women do not receive the gilded invitation to network the old boys of venture capital. Just 4.2 percent of venture funding goes to women-led businesses, according to Stanford University’s Clayman Institute for Gender Research.

This topic has been debated ad nauseum for years, but it reached a fever pitch in 2010 when Silicon Valley commentator Vivek Wadwha wrote a blog post condemning the tech industry for having a “gender problem.” And yet, the numbers refuse to budge. A 2012 report by the Kauffman Foundation found that women form only 3 percent of U.S.-based tech startups and represent less than 10 percent of venture capitalists.

Still, there is some cause for optimism. A small group of female founders are already proving that their tech startups are more efficient with money and capable of generating higher revenues. These women are forming close bonds and networks, like Women 2.0 and Women who Code, and are laying the groundwork for future generations to succeed in tech.

Considering joining them? I caught up with startup founders, U.K.-based Debbie Wosskow and Silicon Valley-based Ruzwana Bashir, to share their tips for launching and building an internet business.

Meet the entrepreneurs

Wosskow and Bashir recently succeeded in raising several million dollars in startup capital for their companies, a process that Bashir describes as “really stressful for anyone.” They are also both graduates of Oxford or Cambridge (“Oxbridge”), and they each have a unique personal style and a knack for accumulating air miles.

Above: Peek CEO Ruzwana Bashir

That’s where the similarities end. The entrepreneurs chose to headquarter their respective startups, Peek and Love Home Swap, in different cities. If you’re not yet familiar with these, Peek is a social travel site to discover things to do in any city. Love Home Swap is one of a handful of home exchange marketplaces, a “next generation timeshare,” as Wosskow likes to call it.

Wosskow, 39, just opened a new office in hip Shoreditch (which is in the East End of London); Bashir set up shop in foggy San Francisco, a mere train ride away from the major venture firms of Silicon Valley’s Sand Hill Road.

Both women work long hours. Wosskow is a single mother with two kids who juggles school runs with the day-to-day tasks of running a global business. Bashir is a few months shy of her 30th birthday and regularly mingles with some of the most successful investors and entrepreneurs. She’s become a fixture in the style and business pages, having made Forbes’ most recent “30 under 30 list and the cover of the New York Times‘ style section.

How did the two get started as an entrepreneur?

Wosskow got started with her first company at 25. She believes that it’s possible to be an entrepreneur at any age, but it’s easier when you’re young. “The attitude you have then is about wanting to give something a go,” she says. “That’s a very American trait.” Another hurdle later in life is the sky-high cost of child care, which is a constant struggle for Wosskow. Meanwhile, Bashir formed the idea for Peek in her mid-20 as a graduate student at Harvard Business School, and she subsequently moved to Silicon Valley to raise capital and grow the company.

Better place to found a company: Silicon Valley or Silicon Roundabout?

London is as good as any place to start a company, but it hasn’t always been. Wosskow wouldn’t consider relocating to the U.S., at least for the time being, as her professional network is primarily based in the U.K. She views her network of girlfriends as her “power collective,” who will always fight her corner. However, her primary complaint about the London startup scene is that it can feel a bit limiting, perhaps even stuffy. Success is often more about who you know (and your college at Oxford or Cambridge) than anything else.

For Bashir, Silicon Valley afforded her access to the top investors and the brightest technical minds. “I wanted to tap into the investors, the talent, and be part of a thriving ecosystem,” she told me. The only drawback is that people can get a bit too obsessed with tech, and Bashir will often find herself at dinners, deep in conversation about her favorite iPhone app.

What’s it like being the only woman in the room?

The entrepreneurs agree that you can make the most out of being in the minority, but it’s not easy. “You are more unique, but you have to fight certain assumptions,” Bashir says. Wosskow feels less alone than she used to, as she’s made an effort to seek out and form close bonds with other female entrepreneurs. “It’s a funny life to choose [and] it can distance you from your peers,” she says.

What are the management philosophies that you live by?

Bashir hasn’t had a troublesome time expanding her team, which currently stands at 20 employees. Many of her standout hires discovered the site on their own, got hooked, and reached out and asked for a job. To make sure her workers feel valued, she sets aside an office hour in the morning where she’ll hear out any problems and discuss potential product ideas. She also sets up “brown bag” lunches, where employees are invited to teach the team a new skill-set, like “Photoshop 101.” Outside experts are occasionally brought in to the office for a Q&A session; Twitter and Square founder Jack Dorsey recently stopped by for a chat.

What was it like to raise capital for your startup?

Fundraising is one of the most challenging processes for any entrepreneur regardless of gender or location. The tech press has speculated that the “Series A crunch” has become acute in recent years, meaning that many early-stage companies will have a hard time securing funding.

It all depends where you choose to raise capital — the pitch will differ depending on whether you’re intending to reach investors in Europe or in the United States.

“In the U.K., I’ve noticed that not many funds want to do venture; most want to do growth,” says Wosskow. “The U.K. story is, Tthis is what we’ve done so far; this is the revenue, and here’s our projections,’” she says. Meanwhile, American investors are eager to see the product and understand the big vision.

How important is it to network?

Networking is crucial — startup founders will need to be prepared to liaise with investors and others with cash. When Bashir formed the idea for Peek, she reached out to friends in the startup world, and several of them cut her a check in a matter of months. Meanwhile, Wosskow has developed her professional network of trusted friends and allies over 20 years.

“If you didn’t have the network, I don’t know how you’d go about raising money and building a company from scratch,” she says. Wosshow runs regular tech events, like Collaborative Consumption Europe, and recommends that budding entrepreneurs make the effort to attend.

Any tips for maintaining a work-life balance?

Wosskow is an early riser — she’s typically up at the crack of dawn so she can respond to a few e-mail and go on a run before she drops the kids off at school. She can never fully switch off and will often have to take late night calls to the U.S. and Australia. With the company in full expansion mode, she jets off to America or Australia at least twice a month.

Bashir also works around the clock and admits that it’s a struggle to main any kind of balance. She is at the office 15 hours a day, six days a week. Saturday is her only day off, as Sunday is a “strategic day” to reflect on new ideas and the long-term vision. “I’m pumped out this opportunity to make a difference, so it’s easy to lose track of time and find myself still working at 3 a.m.,” she says.

That’s the thing about startups — it’s risky, arduous work, but there’s never a dull moment.


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