Founder's Poker at the MattPad.

There is a glaring shortage of women in the field of technology entrepreneurship. The industry, in fact, is often described as a “Boy’s Club” filled with chummy male investors and entrepreneurs. I am hardly the first person to notice this problem. What follows is a brief exploration of how that all plays out at the practical level, despite the best of intentions.

Recently, a friend introduced me to a female entrepreneur. She wanted feedback on her burgeoning online publishing business. Here’s how the email exchange went:

Her: “Nice to meet you Matt, would be great to catch up. How does 11am on Monday suit?”

Me: “Unfortunately, our company is in the middle of a major sprint and I don’t have time during the week to dedicate to stuff like this this. If u can pick a weekend morning that works for you, that’s best. LMK.”

Her: “No problem at all- how about 11am Sunday morning. I have a meeting at XYZ Restuarant at 2pm, though should give us plenty of time :)”

Me: “Sounds perfect. Just come by my apt. 123 Whatever St #123 SF. Near ABC Avenue.”

Her: “Great, know any good cafes in the area? Probably be better to meet there if it’s okay.”

At this point, I start to get a little annoyed. On the one hand, I can understand her caution. She’s a woman. I’m a man. We’ve never met. Going over to a strange man’s apartment is, for some, always a little worrisome.

Nonetheless, I am really effing busy right now. The correct word, actually, is “completely overwhelmed.” Going to a cafe is going to add an extra ~30min to this meeting. “Ugh. I probably shouldn’t be taking the meeting in the first place,” I tell myself. (Then again, I probably shouldn’t be blogging either…)

Regret is starting to set in.

Maybe I’m taking it too personally and overdramatizing the situation, but what’s worst is that now I also feel a little insulted: “Seriously, you’re asking for my help with your business on the one hand, and then treating me like I’m some Craigslist rando on the other?”

Not that her concern is completely irrational, but it makes me think about all the weirdness and wonder: “Why even bother?”

I feel defeated.

Me: “In that case, then maybe let’s just stick to email.”

I do not like this resolution. I want to help. The quality and quantity of the advice I am going to give her over email is going to pale in comparison to the advice I would give her in person. Assuming my advice is actually value-additive and not just a waste of time, this female entrepreneur is now at a competitive disadvantage for no other reason than because she is a woman.

This is not the result of sexism. (I invite entrepreneurs of all sexes over to my apartment all the time.) I was behaving rationally. I had good intentions. In her own way, she was behaving rationally as well. But she wouldn’t have this issue if she was a he.

And I’m sure this problem plays itself out all the time in matters of business and politics and everything in between. #Fail. Relationships drive business. Relationships drive politics. Relationships are how you get ahead in most things most of the time. And if women can’t have the same kind of relationships with the men above them as their male peers, then they’re just not going to rise to the tops of their industry or field and nothing is going to change.

Honestly, I attribute much of my (tentative) success to the fact that I’ve been able to cultivate relationships with a string of high quality mentors (all men, btw). These people have sped up my learning and personal development in crazy, awesome ways. And I am incredibly grateful to have had those opportunities. It is because I feel such gratitude for the people who’ve helped me that I am so willing to carve time out of my already overwhelmed life to help the strangers that ask for it.

Except, apparently, I can’t help women. At least not in the same way I’d help a man. I really don’t like that fact. But I don’t know what to do about it.

Update: While I’m only referencing one situation here, I’m writing about this topic because I’ve seen this kind of dynamic play out repeatedly with other entrepreneurs in other situations. The pattern is basically: guy entrepreneurs make friends with other guy entrepreneurs. Bromance ensues. As a result, junior dude learn the tips and tricks and inside scoops that are going to give them an edge in the marketplace from senior dude. However, I don’t see the same thing happening with junior female entrepreneurs and senior(ish) male founders. And I don’t think the reason is that people are trying to be sexist. My story is simply illustrative and, perhaps, indicative.

Matt Mireles and Marc Randolph, Founder of Netflix, at his house in the mountains above Santa Cruz.
Me and SpeakerText consigliere Marc Randolph, Founder of Netflix, at his house in Santa Cruz.

UPDATE on August, 2014: When I originally wrote this 3 years ago, I got brutalized in the comments, called a rapist, a chauvinist, and more. It was awful. It also turned out that I was wrong in my impression of the situation––the entrepreneur in question had been introduced blindly by a well-intended friend and wasn’t actually seeking advice. In retrospect, my response was a bit douchey and self-important. Yet all of these post-hoc learnings reinforce my original thesis. And yes, I’ve learned a lot since I wrote this and no longer invite entrepreneurs over to my home, but that’s as much a product of the fact that I have a family and 2 year old as it is anything else. But if it’s not me, it’s some other, younger, less enlightened entrepreneurs that’s 100% used to drawing no boundary between work and life. Professionalism comes at a later stage in the company building process. In the early days, there are no boundaries, most of the time. This probably not true re: serial entrepreneurs on company #2 thru N, but that’s how almost every high functioning first time founder that I’ve seen operates. Sadly, I still don’t know how we fix this. For more info, I strongly recommend reading What It’s Like Raising Money as a Woman in Silicon Valley