The Games We Play
Years ago I went to meet someone who was an investor. He did not invest in the spaces that I invest in but this one investment was a crossover and our mutual friend thought we should meet. And so we did.
I remember that I felt like we were circling each other when I got into the office. It was like we were about to start sparring but it was intellectual sparring. He essentially began to tell me about how smart he was, the deals he had done, how he went about them, how it all works. There was zero humility there. I sat there listening and acknowledging as the thought went through my head “if you want to play this game I can play this game too”. So I pumped up my chest and began to talk about my world in the same vein. I call this game my dick is bigger than your dick. It is a game that women rarely play.
There is no doubt that I am playing in the boys sandbox. When only 4.4% of active VC’s are women that says something. I am not a VC but my involvement and many of the things that I do to engage the companies I have invested in is similar to the way VC’s operate. After all, I have been sitting on the sidelines for many years being involved in the backend through my husband. There was a learning curve getting into the investment business and I am still learning every day but the curve was not as steep as it would have been if when I made my first investment and did not know the different between preferred and common stock.
There is a competition in the investment world that nobody really talks about but it is there in black and white. Did you see this deal? I am in that deal. They are killers. It is going to be my best deal. Oh I saw that deal, you invested in them? Hmm. I was in that deal last week that got acquired. I made a killing. I was able to get out now and sell my shares, so smart of me. I don’t need to go on but you get the point. It is the same game, my dick is bigger than your dick.
Here is the thing, I really don’t like the game but I can play the game. I am extremely competitive. I do not like to lose. I also find myself playing that game when I find myself in a room of men investors. I always walk away thinking to myself “why did you have to behave like that”? It is probably better to say nothing at all and just smile. More than likely it is all my age old insecurities coming out. I don’t like the way this game makes me feel in in the post.
On the other hand, I am glad that the game was played at the end of the year. Gives me a lot to think about when it comes to taking some time off and mentally preparing for the year ahead. My biggest wish that is in 2015 there are more lone women investors who I work with. We probably play a different game but at least I find the game has more humility.
Its the same with founders. Flaunting Investor names and “How did you get her to participate”….A bunch of investors who came into our 2nd seed realised you were invested in SE *after* they committed and told me they respect you and have co-invested in a few deals with you.Point being they might have committed faster if I said I had Joanne Wilson in our round, but I didnt.If Investors dont have conviction in my business, taking another Investor’s lead is a poor way to start a relationship.Thanks,Pranay
Love this post 🙂
The question is — and I definitely struggle with this — how do you change the conversation in these situations? I’m not always content to sit and smile but neither am I content with joining the big dick game.
that is the million dollar question.
Because I am in the sport space I have to play the big dick game on a daily basis. As I have gotten older, gained more experience, navigated successfully and disastrously through different circumstances I have learned to trust my whole self – my knowledge, my judgements, my instincts and readily acknowledge what I don’t know. I am also eager to learn from every interaction, circumstance and relationship. A wise friend told me – don’t shrink, don’t puff, stand your sacred ground. No better antidote to the BDG!
I love that, “don’t shrink, don’t puff, stand your sacred ground.”
I look at it from the flipside: Sometimes, it is niggling insecurity layered with a fondant of superiority and a sprinkle of douche on top that makes people act like braggarts. If investor X is so competent, then why brag about it? I.e. if your dick is that big, we should have heard it swinging in the market without you having to talk it up. The investor from that meeting probably looked you up beforehand and went from impressed to a bit uneasy, so, he felt the need to impress his accomplishments upon you.I agree on having the ability to play the game but not necessarily seeing it as the optimal way to proceed. Assuming a situation of peers, what of countering along the lines of “hey, we’ve obviously looked each other up and agree that co-investing in future has potential, hence agreeing to even meet. So, lets get down to it [intro agenda item1]…”?
Joanne, I’m so happy you’ve given me the opportunity and appropriate context in which to say this, but I really admire the size of your dick. 🙂
I like your blog.
You can’t change men’s characteristics or the size of their dicks. I too wish their were more women investors.
That kind of behavior always reads as insecure to me. My guess is he was intimidated by your record and experience, and wanted to show you right off the bat that he is also formidable. I have found myself playing that game as well — and then cringing afterwards, too! I’ve found that another tack also works. When I recognize the behavior, I just sit back and say, “Wow. That’s great.” to each item til they run out of steam. And if you can do it with not all that much enthusiasm (but not in a rude way), they often end up realizing they are MORE than tooting their own horns and then get real. And it’s amazing how quickly and how often it works!
I think it is a game that many men eschew as well. Over the past few years I’ve recognized the intense dislike I have to business relationships with type-A, alpha males. Though their sport is largely similar to your interaction above, and many are wildly successful at it and their businesses, I’ve found it healthy and refreshing to smile, keep my interaction short, find the appropriate exit from the meeting, and move on with life; it is already much too short.
Seems like you do just fine with your approach and set a great example for other women investors to follow.Leave a wrong where you found it.
Corollary: You can’t invest in every deal. I am glad when people do well. If someone passes on a particular deal that works out, ask why they passed. Might be a different reason than you assume if they are honest (for example, Fred Wilson’s story on AirBnb). Sometimes with angels, you are not in the mood to invest, don’t have the cash flow to invest at that moment, or didn’t want to invest with co-investors in the deal you didn’t care for. Lots of reasons.
If you want to witness this behavior on an epic scale take a visit to a trading floor at a bank.
Ha. I’m sure
Something has been puzzling me.The tech world has built an infrastructure of support where winners plow capital back into the system as investors. Most certainly a skewed gender ratio.Through an investment in the wellness space I run into a good number of non tech, quite successful women entrepreneurs. There is a community of entrepreneurs in this space but I don’t see the same community of investors putting the capital back.Am I off on this? If not, why?Seems so curious to me.And–have a great holiday season!
The wellness space is just at the beginning. There are so many of them and few have had big scores. I would think once there are some exits and money is put into the pockets of some top entrepreneurs they will in turn support the next round of start-ups in that space.
This is a late addition to the discussion, but this would be a totally welcome topic for a Gotham Gal blog post. You don’t talk about the wellness space very often. Do you have any insight on why it’s “just at the beginning”? And when you talk about wellness, are you talking nutritionists? coaches? Reiki practitioners? Masseusses? Isn’t the reason because you can’t scale as a wellness provider? Or can you?
will write something.
I was thinking some more about this post and the comments this morning and the underlying theme.Perhaps the issue is how we respond to situations that are lacking balanced behavior. Our natural reaction is to respond with similar behavior in order to counter/balance the relationship. Or we do nothing. It’s a bit of a fight or flight reaction but neither seems to work.When I stop and think about it – the imbalance that we are really facing is usually much deeper than just some jerk being a jerk. Its things like insecurity, fairness, selfishness, etc. In my opinion, this is real enemy. Each virtue that we strive to uphold has a vice that is its shadow. When we are exposed to these shadow we sometimes forget that it is an opportunity to further our own development and practice virtuous behavior. In the case of an insecure investor who brags and doesn’t want to listen – the balance is being a courageous leader who is humble an active listener.
I think you are absolutely right.
You are so right on this. As a male I wish there were a more women in the investing space. It just brings so much more balance to the table. Not all men want to play the bragging game and have to put on this pseudo macho act as well – especially while fundraising. Could only imagine how much harder it is to play as a women. If we evened out the male-to-female ratio in the industry we would have a much better ecosystem, better companies, and more opportunity for everyone both men and women.
We should change the game and make it women only, an exclusive club of women doing business with other women, it kind of make sense since we analyze and feel things differently than men. We can come up with a new name too – “cleavage” maybe …
that gave me a good chuckle.
The upper hand is often had by sitting back and asking questions – Oh really? Why do you think that? I’m not sure I agree…etc.Pontificating is one thing, backing it up is another. Posers are more afraid of smart women than smart men, especially smart women who don’t give a rat’s ass.
In a video I watched a while back, Eve Ensler asked something along the lines of “Why do people say ‘grow some balls?’ or “they must have to have big balls to do that!”. She went on to explain that balls are weak and sensitive. If you wanna be tough, grow a vagina, those things can take a pounding. Basically we should be saying we have “strong vagina’s” and be more aware of how we use language and how it also plays a role in the ‘my dick is bigger than your dick’ dynamic.
i love that.
My problem is that I discount people like that immediately (in other business settings since I’m not an investor) and that’s not good for me. Men are so conditioned to talk nonsense in a sales pitch-like manner that it’s hard to sort out who’s real and who’s as full of BS as their patter would indicate.
Yes it is hard to figure out who is full of shit and who isn’t
Gotham Gal, one of first times checking out the blog. Some interesting articles so far. I preface this to not come off too much like the caricature or description of the BSD man profiled here (I have yet to be that successful, but building a good base at 26 I feel.. time will tell). Disclaimers aside, I think fundamentally it is foolish / you can’t remove this part of the game. No doubt you can tone it down and be more tactful and politically correct.. but our society is a “winner take all” world where the .0001 reap the HUGE rewards, and especially in startups. So it baffles me when people take pain / pause to not be HYPER aggressive / competitive. Steve Jobs, Larry Ellison, Steve Balmer, Marc Andreesoon, Andrew Carngie, james Piermont Morgan, Michael Jordan etc… literally some of the most ruthless competitive (and most successful individuals), to walk this earth. Doesn’t mean the ***best humans all around***… but at the top level of success odds are between 1 in 10k to 1 in 1 million you will not get there without being insanely competitive, so it will seem like my dick is bigger than yours.. because in reality they are saying their dick is bigger than the NEXT million. Can’t change the game, you have to out compete, men and women alike. I hope the analogy and insight is taken as an interesting counterpoint to the traditional more pc answer, and not as a typical 26 year old… definitely trying to bring a much higher/sophisticated analysis (a mini former of bsd 🙂 ). thoughts?
One thing to clarify when I say our society is winner take all.. I primarily mean it at the top levels of business, politics and sports. Not that all of society is that way and certainly not that it should be etc.
I am competitive as they come. It is about behavior. Hopefully over time you will see that.
Definitiely. I was intending to question that. I may have failed to articulate my point (it appears I have). Was not that you (or anyone else male or female in particular) wasn’t competive etc. But that because of the competitiveness there is going to be a pretty high level of disckishness / “spiking the ball”. Merry Christmas 🙂