Follow The Money Yes, VCs play a guys' game. But women are learning the rules.
By Julie Rose with reporting by Sasha Smith

(FORTUNE Small Business) – Roberta Chicos was elated after her meeting with a venture capitalist. She was looking for $5 million to start Booming.com--a financial services site for aging baby-boomers--and she thought she'd struck pay dirt. "He called me a visionary," she exulted to friend and fellow entrepreneur Rob Rosen, who was also on the money hunt. Rosen quickly burst Chicos' bubble. "That's a no, Roberta," Rosen explained. "Move on. Don't waste your time." Chicos, 46, did move on. For almost a year, at the height of the Internet boom, she called more than 100 investors and gave 30 presentations from California to Paris. She never got a penny, and last year she gave up. Back in the corporate world where Chicos started, "it was nothing for me to raise $3 million,'' she says. But now that she was on her own, suddenly "people weren't talking to me as a strong, intelligent person." Meanwhile Rosen, 43, found $33 million for his second enterprise, an Internet consulting firm--even though his first company had burned through $20 million and failed.

Why did Chicos strike out? "Roberta's idea was as good as many,'' Rosen says. The problem was the pitch. He says he urged his friend to be brasher, zippier. But "Roberta would not give the two-word answer to a question. She'd talk about the issues. They weren't interested. VCs are simply asking themselves, 'Can she do this?'"

Chicos agrees. "At some point, I realized I was talking another language," she says. "I was talking about people's dreams. And I was being a little too honest about when the payout would come. But I thought that was what business was about."

Women have long struggled to get financing in any form, be it from bankers or the stock market. But VC funding has proved a particularly tough nut to crack. Companies founded by women received only 9.4% of the $35.4 billion in venture capital doled out in the first half of 2000, according to the latest figures available from Reuters' VentureOne. That's up from the 1999 figure of 6%, but it's still discouraging considering the huge increase in women business owners. (The number of businesses--bigger than single proprietorships--owned by women skyrocketed by 32% between 1987 and 1992, while the number of businesses overall grew only 3%, according to the Small Business Administration. Studies show that similar rates continued through the 90s.) With the economy sputtering, women have to give even tougher answers to the hard question: Why don't we get our share?

It isn't enough to chalk this up to sexism. As Chicos' story demonstrates, more important are the mistakes women themselves make. Too often they don't have the networks, don't create the investments VCs crave, and, once at the table, don't strike the chords that make VCs pull out their checkbooks. These issues, too, involve gender. But the burden is on women. That's a happy irony. Once women learn the obstacles, they can usually get to the finish line.

Hurdle 1: The VC world is a good-old-boy network. Women (and men who want to break the mold) have to work with that. Only 4% of partners in the top 38 venture capital firms are women, according to a survey by the Center for Women & Enterprise (CWE) in Boston. And the big-risk/big-bucks ethos is a macho and clubby one. Talk to any VC, and he'll insist that his firm is gender blind. But in more private moments, a VC, like anyone, will acknowledge that the comfort factor counts. Of course, that goes for women negotiating with women as well as for men with men.

The result, however, is moments that go beyond awkward. Rebecca MacKinnon, who heads a profitable, $4 million health-care software firm, was surprised on a visit to a VC last year when he spent the entire hourlong meeting addressing the male colleague she'd brought along. "Each question was clearly posed to our finance guy," MacKinnon says. The VC "never made eye contact with me."

Even more obvious? Janet Kraus, 34, and Kathy Sherbrooke, founders of Circles, which provides concierge services in the workplace, met with two male VCs. According to Kraus, one man said to them, "Kathy, you're married, and Janet, you're not. Janet, what happens when Kathy gets pregnant?"

"I looked at him dumbfounded and said, 'I'll throw a shower,'" Kraus says. Says Lise Buyer, a VC at the Silicon Valley firm Technology Partners, "People think sexism died 20 years ago. It didn't."

With this kind of old-boy spirit still alive, it's no surprise that women obsess over access. Venture firms may receive 5,000 business plans in a year and hear just 50 presentations. "It's impossible to [do] cold-calling,'' warns Megan Smith, CEO of PlanetOut. Only an introduction can "bring the plan up from the bottom of the heap."

But even starting at ground zero, you can build a network--if you do it right. Rebecca Moore, 37, says she didn't know any investors when she started looking for money to start MuseumShop.com in 1997. She got names from former business school classmates and network groups, then called on 100 potential investors. But Moore discovered she was knocking on the wrong doors. "I went down a lot of dead ends," she admits. When she shifted her focus to a small group of firms that funded Internet retail companies, she raised $3 million.

Hurdle 2: Once in the door, you'd better pitch the right kind of business. Although women are starting more companies, too many--fashion or food concerns, for example--perpetuate the image of "pink ghetto" entrepreneurs. No matter how legitimate the idea, many of these won't attract cash. VCs have typically funded 90% in technology; now it's 95%, says Andrea Silbert of CWE. If you're not in that "space," as the lingo goes, the going gets rough.

This bias was clear even at Springboard 2000, a series of venture forums designed to infiltrate the old-boy network and help create a new-girl one. CEOs are rigorously screened to pick the "creme de la creme," says Springboard cofounder Denise Brosseau; they then get tough coaching in presentation skills. At a daylong gathering, 30 women pitch ideas to hundreds of investors. The top draws last year were companies like Cynthia Fisher's biotech firm ViaCell Inc., which has a proprietary technology for stem-cell treatments. Investors lined up to put $5 million into the firm, which had already raised $48 million. Tougher sells were service and retail concerns.

Kristin Rhyne, 30, who founded Polished Inc., a chain of beauty and spa services in airport terminals, knows this all too well. Airport shops can be lucrative retail spaces, and Rhyne had already nailed down a prime lease at Boston's Logan International Airport and had two others pending. In addition, she had a winning management team through her connections with Harvard Business School and from her days in investment banking. But her search for funds had turned up nothing. Her target figure--up to $1.5 million--was too small to get most VCs' attention, and the concept wasn't ringing anyone's bell. But the Springboard process swung Rhyne's pitch 180 degrees, from beauty rollout to real estate play. Suddenly she had a string of prospects and real money, although she won't reveal that amount.

All right. So you're in the door and you've got the right plan. Now what?

Hurdle 3: Style. In too many cases women simply don't display the flair and conviction that men do. "Venture capitalists are not discriminating against women," says Chicos' friend Rosen. "They're discriminating against what they perceive to be indecisiveness." He argues that in a presentation "a guy will say, 'I can do that.' A woman will say, 'I think I can do that.'" The little-engine-that-could routine won't do the trick. (It so happens that the engine that chanted "I think I can'' was female.)

Even experienced entrepreneurs can strike the wrong note. PlanetOut's Smith, who has raised almost $30 million, may have had a tougher time than necessary, says one investor. The investor is a fan but criticizes Smith's "unbelievably demure and self-deprecating presentation'' Smith shrugs at the description, saying, "That's my style." The investor says she has seen other female CEOs with the same problem, including one last year from a hot software firm. "There was a lot of buzz,'' the investor recounts, "but her presentation was full of 'ums' and mannerisms that were not CEO-like. And she [was] almost apologetic for her success. If a man did that, I wouldn't give him money either." The problem isn't uncommon, says CWE's Silbert: "Women would rather underestimate than underdeliver."

If delivery is a sensitive issue, here is one even more delicate: Who's on your team? Entrepreneurs and investors alike admit that, socialized the way we are, a team without a man can look weak and unbalanced. Take the case of Robin Chase, 42, who fired her male president last summer just before going on vacation. That left Chase and her female cofounder in charge of their fledgling company, Zipcar, a car-share concept.

A few days into Chase's idyll on a remote island, she learned that her move had unnerved a major investor, who wanted to renege on his $200,000 commitment. Chase scrambled, spending hours on the island's only phone with her lead investor, who in turn calmed down the $200,000 angel. Chase acknowledges that she is short on management experience, but won't attribute the investor's reaction to gender. Still, she notes the skepticism she has encountered in the male-dominated auto industry. (Instead of calling Chase, one investor always phoned the head of her Boston office--a man.) The incident seems to have left her feeling that she needed a male executive. She's now hunting for a CFO, and the candidates she has seen thus far are men.

No one expects a seismic shift in the ease with which women get VC money --not until there are more female venture capitalists, says Patty Abramson, a partner in the Women's Growth Capital Fund. Accordingly, a study by the National Foundation for Women Business Owners found that 67% of women investors had put money in a women-owned company in the past three years, compared to only 40% of male investors.

But women are quick studies. As they build networks, hone their pitches, and, most important, build track records with startups, they are gaining ground. And that has caught the eye of astute investors. Companies run by women are "making people a lot of money," says Michael Cronin of Western Presidio Capital, adding that his investments in women-led firms since 1990 have given him a 63% return. Mark Thaller, a partner in Zero State Capital, even argues that the plans he gets from women are of higher quality than those from men. Women lead four of the seven firms Thaller has invested in over the last two years, simply because they met his demand "for the best deals at the best prices."

Oddly enough, the slump in tech stocks may also help women, by altering the climate of the venture world. Investors going back to basics may look less kindly on bluster and more kindly on cautious CEOs who can work on a shoestring. Those who burn through $10 million in six months? "We don't want them,'' says VC Abramson. "I want people to come and show me how they can do it for less. Women are good at that."

with reporting by Sasha Smith