Jeanne Pinder (left), the founder and CEO of Clear Health Costs and Jessica Lawrence, managing director of NYTM.

“How different is this room right now, in terms of the percentages of women versus men?” Jessica Lawrence, the managing director of New York Tech Meetup asked the audience at the second Change the Ratio and NYTM Women’s Demo night on Tuesday. She had a point. The crowd gathered at Facebook's Midtown offices to watch women-run founders demo their startups was diverse in terms of age, race, and ethnicity, yet predominately female.

Ms. Lawrence kicked off the evening by confessing that, even as the event’s organizer and a former Girl Scouts CEO, she had mixed feelings about the self-selecting event. “In some ways," she said, "having a whole separate stage just for women sometimes kind of defeats the purpose."

However, Ms. Lawrence went on to explain that in her year and a half of work at NYTM, she has had an extremely difficult time getting female-founded companies to apply to demo. “I couldn’t believe it was because there were no female founded startups in the city, so I decided to do an experiment and put out a call for Women’s Demo Night,” she explained. “And low and behold, 37 female founded startups applied."

“They were all hiding, and now I know who they are and where to find them, so I can invite them to demo at NYTM,” Ms. Lawrence said. The end goal "is to get the ratio to the point where we don’t have to have Women’s Demo Night because half the people demoing at NYTM are women.”

Ms. Lawrence described the event's atmosphere as more “intimate” than a typical NYTM. The rules for demos were also more welcoming—presenters had a loosely-timed five minutes rather than three, and early stage companies were welcome to include Powerpoints and screenshots if their pitches weren’t yet flawless. Attendees grazed on spreads of cheese and cookies, while others looked longingly at Facebook's ping pong table and mini basketball setup.

The demos were as diverse as their founders, featuring everything from Upswing.me, a platform designed to connect black and ethnic women with hair stylists specializing in curly hair (a huge market) to Continuum Fashion, a combination design lab and fashion label that uses 3D and advanced digital printing technology to change the way consumers approach apparel.

“Fashion is about so much more than just buying,” said Continuum cofounder Mary Huang. Along with a pair of her company's 3D-printed shoes, Ms. Huang was also wearing a dress designed using a photo a friend took in Barcelona made by a company called Constrvct--an interactive brand featured on Continuum. “We don’t want to be a site where you just order things,” she added, explaining that all of the user-created designs on Constrvct are public in order to encourage “a creative space for fashion design.”

The night also featured demos from two different gift-giving Facebook apps, Gift Simple and Gift Hit, as well as Fun Org, an event-finding app that launches Wednesday in New York and San Francisco.

But most impressive presentation of the night came from Jeanne Pinder, the founder and CEO of Clear Health Costs, a startup dedicated to increasing the transparency of the healthcare industry. “The problem we’re trying to solve is that nobody has any idea what stuff costs in healthcare,” said Ms. Pinder, who worked at the New York Times for over 20 years before receiving multiple grants to launch Clear Health Costs.

The site, which is currently in beta, uses crowdsourcing as well as a number of other journalistic techniques to gather information about what patients are paying for health care procedures all over the New York City area. “We’re finding that prices vary by a factor of 10,” she noted.

As an example of the type of data she's gathering, Ms. Pinder drew upon an effort to use crowdsourcing to determine the variation in the cost of birth control prescriptions throughout the city. On the site, users can share information about how much they paid for certain procedures and prescriptions, and where. “People are really excited about sharing things,” she said somewhat dryly, going on to reveal results which showed that in Park Slope one can buy birth control for just $17, though two blocks away the same prescription costs $50. The price range for a cardio stress test is even more striking, with procedures varying anywhere from $150 to $1,790.

“The idea is to tell patients where they can get their services, and at what price,” Ms. Pinder said before announcing that the team has finished collecting comprehensive data for the New York area and is currently working expanded into another city.

(flickr.com/flickr4jazz)

Much has been made of tech’s gender divide, with the seeming consensus being that this industry is something of a sausagefest and no one knows how to fix it. But buried within this TechCrunch report, drawing on statistics from Startup Genome, is an eye-catching little factoid: Compared to Silicon Valley and London (which are running at 80:20 versus 90:10 ratios), New York has almost double the rate of female founders.

We’ve remarked upon this trend ourselves, but those numbers are pretty stark. So naturally we can’t help but speculate recklessly as to why this might be the case. Could it have something to do with New York’s comparatively more recent rise to startup hub status? Maybe the lack of an established old boys’ network makes for a different ratio. Perhaps it’s related to demographics, or maybe it’s partly an outgrowth of the boom in female-friendly fashion and beauty startups. Whatever the reason, it's a trend we welcome here at Ladybeat.

A couple of other interesting stats from the report:

• In New York, there’s a scale-stage spike--from 45 percent to 67 percent--in high risk companies. That’s four times as many scale-stage high-risk companies as Silicon Valley. But scale-stage startups also raise 27 percent more money in the Alley than the Valley.
• Local entrepreneurs are 4.3 times as likely to list “content” as their competitive advantage. (This inspires us to wonder what percentage of these startups are founded and/or staffed by literary liberal arts refugees.)

And lastly, something that comes as a surprise to absolutely no one: hometown hero Fred Wilson is the city’s favorite startup expert. Duh.

Kathryn Minshew never had much luck with tech incubators. "My first company I applied to a whole bunch and got rejected." So with her new venture, The Daily Muse, a content and career site for young professional women, Ms. Minshew was planning to skip the applications and focus on bootrapping her firm. "If it wasn't for Rachel Sklar and her post about getting your name out there, I never would have applied to Y Combinator." (That Sklar, always changing the ratio and changing minds.)

The Daily Muse decided to apply and prepped with  local YC alumni. "There is a very specific culture and interview process at Y Combinator. It's like a college, you need to know the culture."

Boom, accepted, which means another thing on their already very full plates. "We just had 100 percent growth month over month in our traffic. We're trying to hire new staffers. Now add moving to California into the mix," said Ms. Minshew. 

Unlike some teams, which head to Y Combinator with little more than a prototype, the team from Daily Muse is going to work on a very specific detail. "We are building out our job products and that is going to be the focus at YC. What we've found among our readers is that traditional job boards are not cutting it for women. We think there is a more holistic approach."

This Saturday the team will be hosting there first live event to introduce members of their online community to one another. She Makes is a pop up fair to celebrate women who create, being thrown in partnership with Saatchi & Saatchi, 85Broads and News on Women.

"We were thinking it might be fun to get some Task Rabbits to dress up in holiday gear and steer people to the party from the street," said Ms. Minshew. Hey, it would not be the strangest task going on this week, by a long shot.

Illustration by Paul Kisselev.

Charlie O’Donnell has long eyelashes, an athletic build and a shiny shaved head: a 32-year-old in his prime working at one of the most highly-respected startup investment firms in New York, First Round Capital. The kayaking enthusiast and devotee of the fitness Bible The 4-Hour Body is known to broadcast his nine-mile cycling commute on Twitter, where he goes by @ceonyc, a reference to his initials.

A power networker, Mr. O'Donnell has made himself a fixture at tech parties in search of the next Mark Zuckerberg, or as it were, the next Margaret. Trouble is, he's also looking for the next Mrs. O'Donnell.

“For men, if we are single, any single female that we are hanging out with has the potential, at least at first, to be a potential date,” Mr. O'Donnell wrote in 2004 on his popular blog, This Is Going To Be Big. “But for girls, you never really know. You can be doing all of the dating type stuff... showing interest, asking them out, etc... and they'll seemingly go along with the whole thing, until the point that you're sitting across from them and you realize, ‘Hey... wait a second... this isn't a date at all!’”

Business and pleasure often mix in the Silicon Alley startup scene, where investors are known to karaoke with their portfolio companies. By now, everyone knows a pitch and a drink can be one and the same—but what about a pitch and a date? With more women on the tech scene, uncertainty is increasingly common.

“I once scheduled a meeting with someone and it turned out to be a date,” one well-connected female techie told Betabeat. That someone was Mr. O’Donnell. One female founder was “asked out to dinner on the pretense of it being a meeting, but it turned out to be a date” with a local venture capitalist, who followed up with an extended series of flirtatious text messages. That man also turned out to be Mr. O’Donnell. In fact, Mr. O'Donnell's name came up repeatedly in the course of reporting a more general story about women in tech.

Even so, there are far more nefarious scoundrels on the scene. Betabeat heard some stories of other investors that sounded like fodder for Mad Men. “I've even heard of VCs trying to sleep with their potential female investees,” said one female founder who used to live in New York and now lives in the Bay Area. “Pretty sketchy stuff.” One woman who organizes tech events said she was stalked for years by a consultant who stopped only after her brother intervened; one female founder met with a Silicon Valley investor who followed up with an invitation to his hotel room via a midnight text message—“and he was married!”

By contrast, Mr. O'Donnell's dalliances aren't perverse—just pervasive. And by most any standard, the energetic VC would seem to be a catch. A Brooklyn boy at heart, he still lives in Bay Ridge near his family. “To my mother’s chagrin, I’m her last hope for local grandchildren,” he told Betabeat in an interview. A product of the Jesuit-run Regis High School on the Upper East Side, he started at the General Motors Pension Fund as an intern in high school and eventually landed a job there. He works hard, plays hard (in addition to kayaking, he runs a pick-up softball game and a dodgeball team), has good taste in restaurants and seems earnest about matters of the heart. “I want to find someone who not only loves me, but lets themselves experience love and doesn't worry about the chances of things actually working out,” he blogged in 2008.

[Disclosure: While Betabeat was reporting this story, we discovered that an Observer Media employee had briefly dated Mr. O’Donnell. She had no involvement in this article.]

Mr. O’Donnell is exceptionally well-connected in the scene and yet still puts his calendar online so anyone can request some face time. He's something of an industry gatekeeper—or as he puts it, “more like a concierge.” Mr. O’Donnell, though he says he doesn’t drink, attends a vast number of events; socializing is practically a job requirement. “The reason I get the results that I do is because I’m a part of the scene,” he told Betabeat. “I have a big social network, and that leads to a lot of inbound. I get an early look at a lot of good deals because I am out at the parties.”

To hear the city’s female entrepreneurs tell it, an ambiguous date-meeting with Mr. O’Donnell is almost a rite of passage—like living on ramen while you launch your first app. One female founder recalled a recent girls’ night out with a mix of tech and non-tech friends, during which Mr. O’Donnell came up in conversation. “We were talking about how he was trying to hit on [one female entrepreneur who was present],” she said, when one of the women who did not work in the tech scene recalled a similar situation she’d encountered in college years ago. “She said, ‘I was the president of my investment club and this guy came to speak. He was bald and he worked at GM and he came up to me afterward and asked me out to dinner, and made it seem like it kind of was a mentoring thing, but it was a date, and it was really weird and really uncomfortable.’” The guy turned out to be Mr. O’Donnell, too. Of the seven women at dinner, the source said, five had stories about fielding Mr. O’Donnell’s attentions.

Not that attention from a young, long-lashed VC is always a bad thing. “My friends and I sometimes joke, we don’t always mind the ratio,” admitted Sarah Wulfeck, a director from a digital agency, referring to the gender disparity. “I think lots of women in tech feel that way sometimes, too, if they're honest. What do you do at an event with a lot of smart young professionals who are drinking and schmoozing and talking about money and dreams? Human social behavior is what it is.”

We turned to Nancy Slotnick, who works as a dating coach and is the founder of Facebook application MatchMaker Cafe, for perspective on how personal the professional should get. “I'm kind of all for flirting,” she said. “I think women don’t do it enough!”

If you’re not sure whether you’re on a date, just ask, she said. “There's so many situations where you could be trying to figure out, is this a date or not a date,” she said. “These days, people work so much, especially entrepreneurs, and if you’re trying to meet someone for dating, you have to do a fair amount of switch-hitting.”

Many New Yorkers complain about the murkiness of modern dating rules, but the issue is particularly dicey in the tech scene, which feels morally tormented by its gender imbalance. Between panels everywhere from South By Southwest (“Has The Glass Ceiling Ever Smacked You In The Butt?”) to the White House (with Valerie Jarrett), countless stories in the tech press (“Not Enough Women In Tech? Stop Blaming the Men,” “Tech Really Is A Man's Man's Man's World”), and awareness campaigns like Change the Ratio, handwringing is endemic. “Nothing seems to irritate nerds more than the idea that they're oppressing people,” one techie mused recently on a forum discussion about women in tech. “It probably has something to do with the fact that so many of them were picked on growing up.”

Most women in tech try too hard to separate work and romance, in Ms. Slotnick’s opinion. But she acknowledged that things can get complicated when the players are a founder and a VC.

“That’s not a switch-hitter situation,” she said firmly. “That’s a situation where you have to choose: date the guy and put the situation on hold, or if you want to get his money, focus on that and put the dating stuff on hold.

“But that doesn't mean you can’t flirt,” she added.

But in light of his influential position, Mr. O’Donnell’s flirtatiousness has come close to getting him in trouble. One woman complained to Josh Kopelman, the managing director at First Round. When Mr. O’Donnell was confronted, he tried to guess who had complained—and guessed wrong. Another well-connected woman in the New York tech scene said she has spoken to Mr. O’Donnell about toning it down. “A few women who have offered their guidance and feedback to him only to be met with defensiveness and a refusal to hear it," she said.

What seemed to grate on many of Mr. O’Donnell’s targets was the sense that they’d been subjected to a romantic version of the bait-and-switch: expecting a meeting, they’d found themselves on a date. We heard other complaints, similarly mild—flirting over Facebook, flirting over latenight Gchat, flirting over email. A male founder-turned-VC was particularly irked because Mr. O’Donnell had hit on his wife. One female founder told Betabeat she had never had a bad experience with Mr. O’Donnell, because she had studiously avoided him. “I heard that there were stories,” she said. “Which is why I never took a meeting with him. But I don't know what the stories actually were. Just heard about heebie jeebies. Ughhh. I like, won't walk near him.”

The vagueness of the accusations is perhaps why Mr. O’Donnell, having established his reputation as a notorious asker-outer, has been unable to detect what’s rubbing some female founders the wrong way. No one accused him of molestation, or harassment, or even talking dirty (with one very nerdy exception).

The greatest offense Mr. O’Donnell actually stands accused of seems to be that of casting a very wide net—which raises the question of whether his detractors aren’t perhaps overreacting. "It's a joke. No one takes it seriously,” one female founder said, of Mr. O’Donnell.

Navigating such relationships is simply part of the territory, she said. “Initially, I remember it being a barrier for me. But I also found that once you prove yourself and you prove that you know what you're talking about, it works to your advantage, because the industry is so male-dominated that when a woman comes into the room, everyone pays attention.”

On a recent Friday, Mr. O’Donnell hosted a luncheon at Vapiano’s, the chic Italian eatery near Union Square where he frequently holds court. The lunch had a special purpose: Mr. O'Donnell wanted to meet more women founders as well as introduce them to other women. “I'm interested in creating more opportunities for entrepreneurs, especially women, to connect to investors early to build relationships—less name-dropping pitches, more casual lunches,” he wrote in an email invitation.

Seated against the window in the middle of the gaggle, Mr. O’Donnell thanked everyone for coming and gave a brief speech about how First Round had just invested in two female-led companies, neither of which had been referred by other women. “Stop being competitive!” he said, and asked the attendees to introduce themselves one-by-one. The group ate, drank and chatted for about an hour and a half. One attendee praised First Round Capital to Betabeat for its hospitality toward women, unlike Spark Capital and IA Ventures, which she referred to as “frat houses.”

After lunch, Betabeat asked Mr. O’Donnell privately about the stories we'd been hearing. He vehemently denied he’d ever blurred the lines. (“I take meetings in my office!” he cried immediately, his voice cracking, when we broached the subject of date-meetings.) Over the weekend, he sent out a mass email claiming a spiteful adversary was slandering him to tech journalists—to our knowledge, this individual is his invention—and asking women to speak on his behalf.

Over the next three days, Betabeat received about 30 emails from women (including Ms. Slotnick and Ms. Wulfeck) defending Mr. O’Donnell as a great supporter of women.

“If you're planning on writing a story about someone in the venture community who has been unresponsive to women, you're honestly looking at the wrong guy,” wrote Jen McFadden, VP of strategic initiatives at Xconomy. “When I first moved to New York as an entrepreneur, looking to build a network, Charlie was the first one to reach out,” wrote Carmen Magar, a consultant for McKinsey's Business Technology Office.

Other women shared stories of how Mr. O’Donnell gotten them jobs, encouraged them to start a company or made a crucial introduction. Betabeat reached out to as many of the emailers as we could, although Mr. O’Donnell had instructed them to “ignore any follow up.”

Some told us flatly that Mr. O’Donnell had never made an advance. But upon clarification that the story was not planted by a vengeful enemy of Mr. O’Donnell’s, and that the scuttlebutt wasn’t about his unresponsiveness to women, but rather his overresponsiveness, two of the emailers acknowledged that Mr. O’Donnell “has a problem,” as one put it.

One well-regarded female member of the New York tech scene rushed to defend Mr. O’Donnell, who she considers a friend. “Charlie does have a reputation for asking a lot of women in tech out,” she said in an email. “But he also has a reputation of supporting a lot of women in tech. It's really important you highlight this. He's helped me and my female tech friends in a number of ways that have had a profound impact.” Mr. O’Donnell recommended her to an employer a few years ago, introduced her to a crucial female friend and mentor, and advised a friend of hers to fight for a better title.

“And back to him and dates,” she said. “He's not sleazy about it. If anything, it's a bit comical because that's what Charlie does. And that's important. I've known Charlie for years and he's a good guy who means well.”

It’s increasingly difficult for a single VC to keep dating and dealflow separate, as tech bleeds into every industry and more and more enterprising New Yorkers are seduced by the startup siren song.

“I met someone who was working outside tech, we started dating, and three or four weeks into it she mentions she has a startup on the side,” Mr. O’Donnell told Betabeat. “To be honest, I was hurt, like, ‘I could help you, you know, this is what I do for a living.’ She didn’t want me to think the reason she was interested in me was because of her startup.

“My thing has always been, I’m a person first and a professional second,” Mr. O’Donnell explained. “And these days, tech is so pervasive. I mean, where do you draw the line? Someone with a startup from Conde Nast? People coming from PR and marketing? A company with a website? If you kept your dating life relegated to Luddites, you would get pretty lonely.”

Computer scientist Barbie at The Makery.
Photo: Becky Carella

Women in the start-up world are outnumbered by men—we know this—and most of them tend to be later-stage employees in support roles, like marketing, public relations and office management.

But we've noticed a trend in the New York tech scene: a strong surge of women in tech who are, well, just doing it. They're starting companies without worrying about how male-dominated the VC-funded web start-up space is. They live and breathe the scene the way their male counterparts do, and many are just as rash, obnoxious and aggressive.

Some of them are working to bring more women into tech, but mostly they choose to ignore the industry's male-dominated tradition altogether, shrugging off the threat of sexism. Many seem not to notice when they're pitching to a room full of men; some notice, and don't care, or notice and care, but do it anyway.

These women are the future angel investors, powerhouse VCs, public company CEOs and start-up mafiosa. For now they're working 100-hour weeks and organizing events via Meetup.com, but--every day--they're hustling. Here's a predictive power list of 25 women to watch in New York.

Kara Bloomgarden-Smoke, Olivia Fialkow and Emily Foxhall contributed reporting.

Winning!

So I’ve been hanging out in the New York tech scene for a couple months, and I realized something: There’s way more guys than girls! Has anyone else noticed this?

I first noticed that all the CEOs were guys. Then I noticed that all the people at hackathons were guys. Then I realized that all the VCs are guys! Then, I got on a bus and it was all guys. Some staff members of some start-ups are girls, though, and some tech bloggers are also girls.

I know some people out there feel that this gender imbalance is bad for some reason, but I just wanted to take this moment to talk about how lucky it makes me feel to be one of a few girls in the tech scene.

Ladies, next time you feel awkward or out of place, think of the perks. First the obvious--the ratio is pretty great for a single girl! When I first started hanging out in New York tech, one guy who is my age but wayyy richer and smarter told me at a start-up party that I could have sex with him if I wanted to (and that his co-founder was also available for sex). This is going to be great, I thought. It was very flattering; I didn't even have to flirt with him.

I love founder boys! They’re so confident!

Being a girl also gets me invited to all the parties and events because the organizers don’t want to have a lame dude party or look like they're not changing the ratio. Perpetuating the notion that women in tech are less interesting and accomplished than men in tech is a small price to pay for complimentary tech bubble drinks, IMO. It's not like I'm gonna raise my own mil anytime soon, you know?

Another great thing about the gender ratio in tech is panels about women in tech. If you’re a female with even the slightest connection to the tech scene, you know you can always get on some panel somewhere to talk about this stuff (and some women tech Twitter lists, and lists of 100 people in tech, etc.). Soon it will be Internet Week, and I’m going to as many women in tech panels as I can. I learn something new every time.

The last but not least thing that’s great about the lack of women in tech: Pageviews! If you ever need a pageview boost, or you feel like your blog has been a little dry in the comments section, you can always throw up a post about how there are no women in tech. It’s always news because it’s always true, and you can pick any piece of tech news and make it about women. Let’s look at TechMeme’s biggest story today, for example: Amazon had a data center go down. Easy. Amazon’s CEO is a man! Post about how the outage could have been prevented if Amazon’s CEO were a woman, as women are known to take fewer risks. Or just write about how everyone is talking about Amazon’s outage when they should be talking about the gender ratio in tech, which is a much more important issue than Reddit being down for a few hours. The key is to get the one militant misogynist who wanders over from Hacker News into leaving some really offensive comment so 80 people feel compelled to respond!

To all my tech ladies: I hope this makes you feel better about being in the minority. Women in tech have been stressing about how to "change the ratio," but keeping the ratio is much easier, much less stressful and much more likely to result in us getting free gin and tonics. And if you think there should be more women in tech (whyyy?), the ratio is totally changing by itself . Like, we already got a Girl Scout in charge of the New York Tech Meetup. Everyone--boys and girls--I think we're good!