Archive for January, 2014

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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The Day is Upon Us

Posted on January 4, 2014. Filed under: startups, venture capital, wildcard |

As a founder, I am not big on company wide communications. At Wildcard we have a company-wide mailing list called “Family,” but I use it sparingly. If there’s an article that’s interesting or a new person starting soon I’ll fire off a quick note, but beyond that I prefer more personal communications with our crew. This past week, however, I did have an instinct to send a note to our group…New Year’s Eve has a funny way of commanding communication between family members, independent of where on the globe they happen to be.

As I opened my email to send a New Year’s message to our small but growing family, the most surface template that came to mind was something to the effect of “Love you all, 2014 is going to be a big year” or “Love you all…rest up…we are going to crush 2014.” I sat with the draft email open for a few minutes…but with slightly more depth behind my thought, I realized that these messages were empty…and further, not how I really feel about what 2014 holds. The truth is, I have this strong instinct that 2014 is going to be an incredible challenge. The email I would have written if I had more than a sentence or two to explain it, would have began with something like “Love you all, 2014 is going to be fucking hard.”

I am so proud of what we accomplished this past year. We have built incredible technology, assembled one of the most talented teams in New York City, and took what began as an incredibly abstract vision of what the mobile internet could become, and turned it into something real that you can touch and feel that hints at the probability and promise of this future. On one hand, I love where we are sitting…and I know that our investment over the last 12 months will continue to yield into the next 12…but I am acutely aware that what we have done is not enough…that for us to pull off what we aspire to…it will require near flawless execution…continued discipline and vigor…tremendous fortitude and flexibility…and increased emotional composure. In 2014 we will deal with an incredibly dynamic ecosystem of giants, bobbing and weaving through their legs and perhaps securing seats on their shoulders…We will get our first taste of the challenges in mobile distribution…We will most certainly say hello to a few competitors who we don’t yet know about…and we will learn what it’s like to design and develop within an organization that is twice our current size and larger than we ever built at Hyperpublic. We’ll move from developing product beneath the understanding lens of our own team and investors, to building under the judgmental and non-empathetic gaze of the masses…we will receive negative feedback…something we have had very little of to date…some people will hate us…or tell us we are wrong…our small knit community of believers will be drown out by the skeptics…and like every good startup to put product into the world…we will painfully learn how to communicate our message and convert the non-believers…pats on the back will turn to punches in the stomach…intermittantly eased by the deep tissue massages of our small and large victories.

There is a battle upon us…it is one I know how to win…but there is no shortcut…no secret weapon…that allows us or anyone else in our position to escape the hand to hand…in the trenches…ugliness of taking a spot in the world that many don’t know they want you to hold and that some actively know they don’t want you to hold. You might think from my words that I am not looking forward to 2014, but it is just the opposite. This is what we do. It’s why we kept the bar so high on recruiting. It’s why we don’t simply hire talent to fill roles, but rather dynamic athletes…with the mental and emotional strength to walk into this fight every morning…and not let the stomach shots or duress dilute our craft. This is the year I get to see why every hire we made over the past 12 months was so so right and I can’t fucking wait. So yea…you can see why “Love you all, we are going to crush 2014” doesn’t exactly say what I needed to say. Upon reflection, perhaps this message would have been more appropriate:

“Family, I don’t need to tell you how much I love this group of people. You can see my affection and pride every day I walk in the door. I feel deeply privileged to walk into the coming battle with such a fine and honest group of human beings. We are a small but formidable cadre with the skills and shared ambition to win any fight we choose to enter…and believe me, the fight was have chosen will not be without blood and grueling conditions. It is in our composure, sustained confidence and cohesion that we will endure and ultimately persevere against any that are not with us. Stick to our plan, but watch and communicate as the battlefield changes…Fight with humility and integrity and those that sit on the sidelines will eventually join our ranks…we are small but will not be small forever…whether back against the wall or advancing through enemy lines, remember that those that are not with us today, may well be allies tomorrow. It is January 1st, 2014. The day is upon us…”

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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 (p.s. i don’t use spell check…deal with it)


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