Women at Wildcard

Posted on January 8, 2014. Filed under: startups, venture capital, wildcard |

I’ve wanted to write this post for a long time…and every time i sat down to do it…it just didn’t come out right. If you’ve read this blog for a while, you know that I care about the people on our team more than just about any other dimension of Wildcard…more than I care about product…more than I care about fundraising…team is everything. It was true it Hyperpublic and it’s true now. When Hyperpublic was acquired by GRPN, we were 10 people…9 engineers and me…1 first generation immigrant and 9 born Americans…8 caucasions, 1 Asian, 1 African American…1 profesional musician, 1 chef, 1 billiards master, 1 former professor, 1 outdoors enthusiast, 1 fashion efficianado, 1 college drop out, 1 improv master, 1 son of a preacher man, 1 semi-manic tech blogger…and 10 MEN…we had such an amazing and diverse group along so many different axis…except gender…where we were shockingly homogenous.

At Wildcard we are now 10 people as well…6 engineers, 2 designers, 1 ops, and me…guess how many women? Not for a lack of interest and not for a lack of effort…but still the facts are the facts. I have a handful of close female friends in the tech community, and a smaller handful of close female friends in the engineering community in NYC…and over the past few years I have listened carefully as they’ve shared their views on building a multi-gender culture into your startup. Here are a few “near quotes” that I’ve heard that have stuck with me and inform the way we make decisions at Wildcard.

1) “if you get to be too big without bringing on a female employee, it get’s much harder to do so down the road.” The spirit behind this observation is that it can be intimidating for a potential recruit to be “the only woman” on a team of 15 males…obviously that intimidation factor grows when you replace the number 15 with 20, 30, and so on.

2) “It isn’t enough simply to have female employees at your company. You need to have female employees in leadership roles at the company.” The spirit behind this thought is that young ambitious women want to see that your organization is a place where they have the ability to grow and advance into influential roles within the company. If the leadership in the company is uniformally male, that does not set a tone of opportunity within the company.

3) “you’re brand of being badass engineers is too unwelcoming and does not appeal to the female psyche in the same way that it does the male psyche. Consider modifying your tone from working amongst the most badass engineers to working amongst the most intelligent people in NYC. There is nothing wrong with communicating the pedigree and ability of your team, but do it in a more gender neutral way.” I didn’t realize that “badass” was a more male value…but I can see how that is sort of lazy language to articulate how special the human beings at our company are.

4) “Women don’t want to be hired simply because they are women. Nobody wants to feel like the token girl that got the job because your startup needed a woman.” This one is so important because I think I and many startups have fallen victim to the reality that it is difficult to source female candidates for open positions…but when you advertise that you are looking to or excited about bringing that diversity into your culture you set a tone that can unintentionally trigger the above sensitivity. In fact, one of the very reasons for writing this long, verbose post is to say “I’m listening…i’ve been paying attention…i understand many of the gender dynamics that are at play in the startup ecosystem. I don’t have all the answers, but I care…and maybe this post will lead to a change in the complexion of our team and maybe it won’t…but I’ve BEEN listening and I don’t know what else to do to address it other than write out where I am in the process of figuring out how to build the best team of men and women and New York City.

So yea, I know there are more dynamics at play than the ones I’ve articulated, and in some sense I’ve condensed hours of conversation down into a few bullet points, but at least this on paper…this is how I’m thinking about gender at Wildcard…and my and our actions will be in response to these shared observations and any more that people would be willing to share in the comments of this post. Been too frustrated with this challenge for too long not to work through it head on.

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2 Responses to “Women at Wildcard”

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Hi, Jordan.

A facebook acquaintance sent me this link after a longish, multiparty debate over your Medium essay about not mashing on your future wife. The person who posted the essay thought it was great; lots of the rest of us thought it boiled down to “guys, please, simulate being a human and it might pay off with a cute smart wife,” which is of course not a helpful message. So the ensuing debate was really about incrementalism and whether that’s worth anything, particularly if the presumption is that the audience is not in a place to hear that it’s wrong and insane to treat women as anything but people, and that people who do that should not be in positions of power, full stop.

After reading this post, it seems to me that you’re really troubled and sincere about wanting to do something to change the culture, but that you’re also so deep inside it that you just plain have no clue. If what you’ve got is the tools you’re working with above, I can tell you that you aren’t going to get very far.

Learning other cultures is expensive, but you’re a guy of means. The way to learn another culture is to go live in it. So here’s what I suggest.

Leave tech for a while. For a few years. Go work in a female-dominated industry, where the first thing that’ll hit you is how shit the pay is. You’ll feel like you’re not getting paid at all, like you’re volunteering. And eventually you’ll have to accommodate to that, because it’s the actual money all your colleagues are living on, with kids and everything, and yes, it’ll be rude for you to be flinging your money about. At that point you’ll be tempted to shrug and decide they’re saints, and that’d let you out neatly because sainthood is admirable but not what you were after. But that’s not allowed when you’re learning the culture. They’re not doing it because they’re saints; they’re doing it because (a) that’s the available money and (b) it had not occurred to them that they deserve kajillions. These are normal people. So – you’ll need to acclimate to the pay level at which people actually live.

Work in K-12 education, or in customer service. A hospital job where you help people deal with their bills or work with them to arrange services might be a good one. Or go to work fulltime for a woman-led political organization devoted to advancing women’s political opportunities. They can usually use a hand with all things tech but will not hesitate to put you in your place if you’re starting to act a bit special.

The temptation for a lot of STEM guys walking into spaces like this is to look around, find the setup slipshod and ridiculous, and decide to take charge and set things right. Nobody is asking you to do that. In fact nobody wants you to do that. Your job here is to learn and understand *why* things work the way they do, not to mansplain and hero your way around. You will probably find that the reasons boil down to several things:

1. There is never enough money because these are not things people like your tech colleagues value particularly, even though socially they’re quite important. So you’re working with a tremendously inefficient system of semi-connected workarounds. The important thing is that everyone knows how to use them already, and that they do in fact work well enough for the purpose.

2. The people being served are actually being served, more or less: they aren’t customers and ROI is not king. They are people.

3. All sorts of things that would be allowed in the world you came from are not allowed here, because you are required to take account of people’s humanity. They have lives outside of work, many of them. They have children who have school snow days. They have elderly parents whom they look after, and mildly disabled children. A union might even be involved, protecting their time and rights for them. They do not have spouses who handle their personal lives for them, nor would they expect or want their spouses to do that. When clients, patients, students, etc. have trouble, you can’t hand them something glib and a free something and a shrug: you actually have to solve what may be quite a complex problem.

4. There’s a leaderboard that people may or may not be much interested in. You’ll find few people there who have ever spent days fighting for a top score on a game, or devoting months to leveling up. They don’t care that much about games, they’re involved in actual life, where the stakes are far higher. And they don’t see the point of going balls to the wall for a point score where what you’ve won is…points. Even as children, most of these people didn’t find that exciting.

5. Social relationships are paramount. While it might be true that Laurie’s way of doing things isn’t the most efficient, everybody likes Laurie and she’s hella easy to work with, and she has relationships with *everybody* going back 20 years, which is worth gold. So we will live with Laurie’s way of doing things. What we won’t do is chronically snipe at her to show how much smarter we are about efficient ways to do things, because then she might feel bad, and eventually quit. And we don’t want that.

6. They don’t know about tech wonders that could wondrify their lives. On explaining, even if you can find the money for implementation, you might get a cool reception because the point is not necessarily for the organization to get ahead in the sense of sales, domination, etc. The point is for them to work extremely well with *many other organizations* to do particular things in an environment that is not awash in money. And if these are not systems the other organizations are familiar with or can afford, then they may not actually be very useful in this context.

7. Ranks and hierarchies might work differently than what you’re used to. Money is not clear evidence of importance to the enterprise. Clerical and support people are probably not regarded as lesser; they’re there because if someone didn’t do that job, the organization would be in trouble somehow.

8. There’s a fair amount of conversation about the social point of doing the work in the first place, what you’re all there for and how better to achieve that goal.

9. If someone starts ogling a young woman in the office and talking sexist, the weight of a thousand middle-aged women’s disapproval and enmity will come down on them. Sexual harassment means you’re out on your ass and persona non grata for years. No one will ever forget.

So essentially, in learning why things work as they do, you’ll wind up learning to respect ways of thinking and being that are actively disrespected where you are now. And you’ll learn in very tangible ways why they deserve respect.

A thing to keep in mind is that by the time you’ve hit adulthood in tech, any women you’re likely to meet there have already spent at least a decade accepting and normalizing a daily hail of miserable treatment and, maybe, priorities they don’t entirely share. It starts in elementary or middle school, where the math and robotics and logic-games clubs are all about *winning points*. Prowess through winning points.

I’ve had lots of arguments about this with guys who’re heavy into STEM Olympiads and wonder why more girls don’t show up when they say specifically that girls are welcome; I tell them that not too many socially capable girls want to spend a lot of time with boys whose entire focus is showing how they’re the best because points. They see this as not just pointless but unpleasant, even stupid — even though they may really dig math, love puzzles, love science. It doesn’t help that honestly, the boys don’t really want them there (and that maybe the coach is awkward around girls and much more comfortable with the boys, too). I mean they can sense that. The men I’m having these conversations with are intensely competitive people and, for them, knowing their rank at all times and fighting for a better one is the stuff of life. And it’s very hard for them to acknowledge, let alone understand, that TIMTOWTDI.

In the end, that old hacker acronym is what it’s all about. And this is very, very hard for a whole lot of tech bros to accommodate themselves to. Witness what happened after that payroll guy decided everyone in his company should be paid a reasonable living wage, how apeshit people went because it shrugged at the leaderboard thing.

If you want diversity, then you’re going to have to accept that values are also diverse. And that really is going to change the complexion of your company, and upset people. Same thing on a much bigger scale if you want to see that change across an industry.

Anyway — seriously, give it a shot. You’ll learn more about diversity and respect in three years working in an environment like I’ve described than you will in three decades of listening to other people tutor you for free in conversation.



Thank you for the thoughtful post. I think I’ll have to read it twice…a lot there

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at Jordan.Cooper@gmail.com (p.s. i don’t use spell check…deal with it)


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