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Katherine Barr, partner, Mohr Davidow Ventures.

Rachel Idzerda for The Globe and Mail

Katherine Barr is used to standing out.

When she was in university, she managed the top-performing College Pro painting franchise in Quebec and led Japanese tourists around Banff, Alta., on horseback. "It was me and 80 cowboys," she says.

She grew accustomed to stares from locals when she worked in Japan for the Nagano Winter Olympics; one elderly lady on a train remarked that the 5-foot-10 Ms. Barr was as tall as a mountain, not realizing she understood perfectly what was being said about her. "I didn't totally fit in all the time and I had to be okay with that," the Perth, Ont.-born Ms. Barr says. "Being comfortable with breaking the mould and not just conforming to what society expects of you is a really important thing."

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I've invited Ms. Barr to lunch on a crisp January day in Toronto to talk about how she is breaking the mould as a venture capitalist with one of Silicon Valley's most established financing firms, Mohr Davidow Ventures.

The affable, upbeat, 42-year-old Ms. Barr has played a pivotal role opening doors for Canadian startups in the Valley. A surging class of Canadian entrepreneurs, including Shopify's Tobias Lutke and Hootsuite's Ryan Holmes, is rebuilding the country's reputation as a high-tech hothouse, and Ms. Barr can lay claim to some of that success as co-chair of the C100, an organization formed with other Canadians in the Valley to link Canadian entrepreneurs with U.S. financiers. "She's been a tireless worker and supporter of the community," C100 co-founder Chris Albinson says.

Ms. Barr also holds another distinction that speaks as much to her achievements as the deficiencies of her adopted ecosystem. She is one of precious few women who have reached the level of general partner at a Silicon Valley VC firm, and is believed to be the only Canadian woman in such a role. Though she wears the crown of trailblazer rather cheerfully, her singularity points to a chronic problem in the world capital of innovation.

The provocative and controversial cover of the Jan. 28 issue of Newsweek offers the latest take on the issue: It depicts a black computer cursor lifting up the back of a woman's dress, next to the line "What Silicon Valley Thinks of Women." The story is a depressingly familiar roll call of anecdotes and data portraying Silicon Valley as a "bro community … stunningly backward when it comes to gender relations."

Despite the success of top female executives, including Facebook chief operating officer Sheryl Sandberg and Yahoo chief executive officer Marissa Mayer, the Valley is framed in the article as a misogynistic borough rife with "gender-based hiring and firing, major-league sexual harassment lawsuits and a financing system that rewards young men and shortchanges women."

While some of this is old news, it is also true that less than 3 per cent of U.S. firms that received venture-capital financing – the lifeblood of fast-growing startups – from 2011 to 2013 were led by women, according to a survey by Babson College researchers, while just 15 per cent had any female executives (up from just 5 per cent in 1999). As for U.S. venture capitalists, 6 per cent were women, down from 10 per cent in 1999, the study said.

As we settle in to lunch at Donatello, a cozy, upscale Italian restaurant near Eaton Centre, it's clear that battling sexism in the Valley is not a defining issue for Ms. Barr, though she acknowledges it's a problem. "I honestly don't think about it very much," she says, adding that her mentors were all men "who gave me a chance, let me stretch, spread my wings." At Mohr Davidow, she says, "I've had the privilege of working with adults." (As it happens, she has sponsored three companies led by women in her seven-plus years at Mohr Davidow. That's of the 14 investments she has sponsored or co-sponsored with other partners.)

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After Ms. Barr selects the house salad and squash ravioli in cream sauce with orange (I opt for the Caprese salad and ravioli stuffed with crab, goat cheese and roasted pepper in a tomato cream and pesto sauce). I inform her that lunch is on The Globe and Mail. "Venture capitalists don't often get treated to lunch," she says with a laugh. She always picks up the tab when dining with entrepreneurs, she says, though she jokingly tells them that after taking their companies public, they can treat.

Venture capitalists are extreme risk takers, backing entrepreneurial dreamers and their speculative ideas, services and products. If the ventures succeed, they can disrupt whole industries, change how we work and live, create enormous wealth and cause massive dislocation.

If they fail – as most do – millions of dollars invested by the likes of Ms. Barr can vaporize. Ms. Barr, one of six general partners parsing out Mohr's $670-million (U.S.) Fund IX to enterprises, is expected to generate a threefold return for her investors, so the successful investments must generate returns of at least 10 times the investment to compensate for those that fail. She tells entrepreneurs that if they want to tap VC money, "realize what you're signing up for: To partner with your investors to swing for the fences and not stop until you've reached a $1-billion valuation," she says.

Venture capital is an unconventional career with no standard way in. Some venture capitalists are trained financiers, many are entrepreneurs, others are ex-journalists. "Sometimes, I think you almost have to not want to be a venture capitalist to become one," she says. "A lot of it is serendipitous."

The daughter of a small-town entrepreneur, Ms. Barr grew up wanting to become a CEO. She was an achiever with a sense of adventure, presiding over student council, competing on her high-school downhill ski racing team, riding at Olympian Ian Millar's horse farm and travelling the world. "My philosophy was I wanted to try as much as possible," she says. "I didn't want to focus on one thing because I felt I'd be missing out."

Ms. Barr studied philosophy and learned Japanese at McGill University, which led to jobs in Banff and Nagano. Following the 1998 Winter Olympics, she visited her younger sister, who was working in Silicon Valley for Elon Musk's first startup, Zip2. The dot-com boom was under way and Ms. Barr was entranced. "It felt like … the world was being invented there," she says. "I wanted to be a part of it."

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She earned a master's degree at Stanford University and took courses in the management science and engineering program, where she says she "found my people," interacting with entrepreneurs and venture capitalists as she helped run business-plan competitions for the student business association. She then moved to Boston in 2002, working briefly for a tech startup before joining Vantage Partners, a consulting firm co-founded by the Harvard Law School negotiation specialists who wrote the bestseller Getting to Yes.

Ms. Barr spent four years as a negotiator working with big tech firms including Cisco and getting "first-hand exposure to what works and doesn't work in a business environment," she says. She once saw a client grind down a supplier so much on pricing that it put the other company out of business – to her client's detriment. Treating business as a zero-sum blood sport, she concluded, was not good business.

Ms. Barr, who had a late breakfast, barely touches her salad and will leave much of her ravioli behind. The waiter looks disappointed, asking whether there's anything wrong with the meal. "No, I'm just talking," she replies.

After tiring of constant travel for work and still in pursuit of a CEO job, Ms. Barr decided to return to California. Stanford professor Tom Kosnik asked whether she'd ever considered a career in venture capital. She hadn't, but thought it might be a good fit. Mohr Davidow was looking for a partner, he said. She joined in 2007 and became general partner three years later. (She also married a Canadian aerospace engineer working in California; they have two children, ages five and three.)

Colleagues describe Ms. Barr as a great listener with a deep sense of empathy for those she backs – but also as an incisive board member who asks tough questions and gets to the root of challenges facing the businesses she's backed. "Katherine is particularly good at being honest with entrepreneurs," says Atlee Clark, former executive director of the C100. "She doesn't waste anybody's time."

Those entrepreneurs Ms. Barr has backed say they appreciate her interest and comfort in diving deep into their business issues, while displaying an important quality for a venture capitalist: a down-to-earth personality the entrepreneurs felt they could work closely with for several years.

"We had our pick of investors," says Max Yankelevich, CEO of New York-based WorkFusion, a startup whose technology reduces freelance labour costs for companies, which chose Mohr Davidow to lead a $15-million financing last spring. "One of the biggest reasons we chose Mohr is because of Katherine. Because the board is quite small, you want to make sure everyone fits in. She can get her point across but in such a way that nobody feels like she's telling them what to do."

Ms. Barr advises her entrepreneurs and helps them recruit senior executives, but "we don't tell them what to do, we don't run their businesses," she says. She tells them to be authentic, to figure out their values and who they are, and "be true to both."

Ms. Barr typically invests between $3-million and $8-million at the early fundraising stages, focusing on opportunities in online retail and e-commerce, consumer technologies and work-force automation. In particular, she's looking for entrepreneurs who have the wherewithal to expand their companies into much larger operations, with enough initiative to make decisions on their own, but not too strong-headed to reject feedback.

The companies she has backed range from San Francisco-based Ticketfly – a disruptor in the event-ticketing business – to Vancouver's BuildDirect, an e-commerce firm that sells and delivers heavy loads of building materials to contractors and do-it-yourselfers. Ms. Barr doesn't want to single out any of her "babies," but she obviously has a soft spot for BuildDirect founder Jeff Booth, whom she backed in two recent financings. "He's one of the most determined entrepreneurs I have ever met," she says. "I just love working with him."

In her role with the C100, which ends next month, Ms. Barr is equally excited "seeing all these [Canadian] entrepreneurs grow up."

Much has happened since the C100 was formed in 2009. Successful Canadian startups were scarce, starved for financing and prone to selling prematurely. Several prominent Canadians in the Valley decided to help. Since then, the C100 has worked with the federal government to improve the venture landscape, leading to changes in the tax code and the introduction of a visa program to entice foreign VCs and entrepreneurs to invest here. Ottawa also created a $400-million (Canadian) fund to pour into venture financing. The C100 has sponsored gatherings for startup CEOs and brought many Canadian entrepreneurs to meet U.S. financiers through its "48 Hours in the Valley" program. Today, Canadian entrepreneurial success stories abound.

But there is work to do to refresh the C100 now that its initial goals have borne fruit. Ms. Barr and other C100 leaders have been assessing what role the organization should play to ensure it remains a relevant conduit between Canadian startups and Silicon Valley. Meanwhile, Ottawa "must do a better job of approving visas" for foreign executives hired by Canadian startups, she says, as some languish for months waiting for paperwork to come through.

If the C100 has unfinished business, so, too, does Ms. Barr. Now in her eighth year as a venture capitalist, she has yet to lead her first "exit," a transaction that locks in investment gains for Mohr Davidow. After investing in their early stages, she's confident the companies she oversees "will over the next handful of years be teed up for an exit."

As for her ambition of becoming a CEO, "I'm pretty convinced I will start something at some point," she says. For now, she says she feels "entirely fulfilled." If she does take the leap, it wouldn't be to realize an unfulfilled dream, but "for the challenge, to do something different – which is what I've done my whole life."

***

Hometown: Perth, Ont.

Current home: Los Altos, Calif.

Education: Earned a BA in philosophy at McGill University, an MA at Stanford and completed all but a handful of electives in Stanford's management science and engineering program.

First computer: Her father's TRS-80. She learned to program in BASIC on it.

Family: Married to a Canadian-born aerospace engineer she met at a "Digital Moose Lounge" Canada Day event in Silicon Valley. They have a five-year-old son and three-year-old daughter.

Childhood adventures: Got a pony at five, competed on her high-school downhill ski racing team, learned to ride and jump at Ian Millar's horse farm, travelled in Yugoslavia before its post-Communist breakup.

Adventures as an adult: Got a motorcycle licence, logged 22 hours of pilot training on a Cessna 172, has tried skydiving and off-piste downhill skiing, and climbed Japan's Mount Fuji. Her next adventure? Learning to play classic Canadian tunes on the fiddle her husband gave her for Christmas.

Memorable Olympic experience: Worked as an interpreter and announcer at the finish line of the women's downhill ski event at the Nagano Winter Olympics.

On how the Canadian startup scene has changed in recent years: "There are a lot more high-quality entrepreneurs who are wanting to swing for the fences. Their idea of going big is not $5-million in revenue five years from now – it's $100-million-plus."

What she'd like to see more of in Canada:"It would be nice if we could encourage more people to provide angel money for getting [startups] off the ground. That's where Canada still has a [funding] gap. We just don't have enough people who have seen the movie before in terms of what it takes to scale a company from $5-million in revenue to $20-million to $100-million."

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