Oh No He Didn't -- A Guide for VC's When Talking to Women Entrepreneurs

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An interesting phenomenon has happened since I've had twins and been taking some time off to mentor women-run companies in Chicago. At least four women founders have asked me to accompany them to VC meetings. Why? Because, in their words, they need "a buffer."

Wow. Why is this necessary?

It became very clear during some of the meetings that I had with these women. VCs, as far as I can tell, are almost all male, and they tend to take a very male-centric approach to things in meetings with women entrepreneurs -- especially in the first meeting. Instead of establishing trust, they unleash a question barrage. Instead of complimenting the work we've done, they tend to take a standoffish, "if-you're-lucky-you-might-get-a-piece-of-this" approach. And instead of trying to accommodate issues that women face, sometimes awkward questions arise that tank meetings completely.

Guys, put simply, it's like dating. First, we need to know that we're not going to end up dead in a ditch somewhere, second, we're the ones that are used to playing a little hard to get, and finally, a little foreplay is nice! The question barrage can come later. It's expected before you get married to have to answer a lot of queries. But it doesn't have to happen in the first five minutes of the relationship.

If you are a male VC reading this, you might question why you should care. You have the money, right? You have lots of entrepreneurs stalking you down corridors, cold-calling you and memorizing your Starbucks drink order, right? There's enough companies coming to you that you don't need to make concessions to your approach, right?

But here's why you should take notice. In my experience, women make awesome entrepreneurs. We have a particular knack for building organic companies on a very lean budget, and a real skill for in-person sales that often eludes men. In addition, more of us learning to code, and this makes us especially dangerous. The numbers of women building lean startup prototypes using their own coding skills are getting higher. These skills have become especially critical in a time when series A and B rounds are scarcer and overall angel funding is elusive. Women tech entrepreneurs are still in the minority, but not as much as you would think. Recent numbers from 1871, Chicago's premiere co-working space, have shown that it's composed of 22 percent women founders. That's not 50 percent, but it's enough to matter.

I have mentored hundreds of women entrepreneurs, and my experience shows that women tend to "over-prove" their business models, building so much with angel funds and seed money that we don't fit into typical buckets. We assume that if we create an amazing proof of concept that goes far beyond the typical 100k-a-month mini-machines that you usually see, that you'll be especially blown away and invest immediately. Logical, right? But our A-type approach may instinctually turn you off. No one liked that girl at the front of the class who always raised her hand and knew the answer to every question. You guys may identify more with a male entrepreneur that walks in and has some great data, a no-nonsense approach and a cocky attitude, but he might have a sub-par or average money machine to back it up. Our money machine will likely be bigger and better. And yet...you probably will have trouble overcoming that barrier of liking us, since NO ONE liked the know-it-all in grade school. She often added up to more homework. But you need to learn to like her. Because she can make your fund very, very happy.

I've also noted that women, moms or not, tend to view their companies with a maternal, protective eye. If you hit us with a question barrage right off the bat, we're going to clam up and take a suspicious, protective stance. But if you take fifteen minutes to get to know us and share a little about yourself we'll open up and trust you a bit. And then both sides will be talking, instead of one side talking and getting increasingly disdainful or annoyed while the other side gets increasingly angry and suspicious.

An additional trend about women that's relevant here is that most women I know are hard-wired to being pursued, not to doing the pursuing. This is not an overall rule. There are some women that buck trends and propose to their boyfriends. But I know very few. After you've spent a few minutes getting to know us and having a nice conversation, if you're impressed and want to work with us, memorize three things about us and mention them the next time around. It's my dream to someday walk into a meeting with a VC and have him have a Starbucks green tea latte waiting, as well as conversation starters like asking about my twins by name and how things were going at 1871. I know that this is totally non-traditional, but why not give it a shot? It happens so rarely that it'll definitely give you a leg up over any competition, if you decide her business is worth something.

Finally, in one of the meetings that I did accompany a woman to, the woman entrepreneur was pregnant. I won't name names, but it didn't go well. In fact, it was somewhat disastrous. I know that the minute you see a pregnant woman entrepreneur that that you're likely worried that we'll be tired, more forgetful, more emotional...I'm sure that if you have kids you lived through that with your own wife. Heck, we're even worried about how we'll deal with it all. But the fact remains that I've mentored scores of women and none of them ever failed due to kids. They just got better at delegating. Months after having my twins, even though I was exhausted, emotional and could not remember my own name, I threw myself into work beta-testing new technology at the Obama campaign as a volunteer. I would have done anything to distract myself from the postpartum depression that hit me for a few months, and it greatly helped me on the path to healing.

It greatly worries me that society has an impression that women can change completely when they have kids. There seems to be this idea that we're going to turn into cooing baby drones that want to do nothing but coo over baby blankets and make jam. (Not that there's anything wrong with making jam. I make a mean lavendar-lemon curd.) But this impression that we're going to change overnight is completely invalid. The kind of woman that starts a company is the kind of woman that needs societal problem solving to fulfill her intellect, period. She's not going to morph into something else. So remove that fear from your head, and instead concentrate on the fact that while she's tired, emotional and forgetful, she's still her, and there's a reason you set a meeting to talk to her. Don't, under any circumstances, ask her how she plans to manage her pregnancy. Assume she will have a plan. Only an idiot would not, and again, she's in front of you for a reason. And don't take the approach of ignoring it. That's just weird, if we're the size of a house. Instead, ask her when she's due, if it's a boy or a girl, and say congratulations. Share a story about kids. And then head to your office and have a worryfest, if you need to. Give yourself fifteen minutes, tops, then get over it.

I do think that there's a bit that women can do to make their companies more appealing to venture capital companies, as well. In general, it'd be excellent if the women-run companies I mentor would focus a bit more on data, instead of gut. I am guilty of this too -- it's not a huge problem for us to fix. And we should be the ones to self-correct our issue about over-proving our models. Enough is enough. Feel free to give us this advice, as well as any other advice that you have... the more we learn, the better we get at what we do. Just make sure that your approach leads to us listening, ok? Because in these meetings I have been attending, the most frustrating thing I see is that each side is struggling hard to connect... but not getting there. We just need to cut each other a little slack.