Battle of the Sexists


On Women and Tech

I am scared. About sharing my thoughts publicly. For the first time. And that’s unlike me. But engaging about women in tech is a minefield and so many choose to stay on the sidelines. Then three things happened (not including the nasty man’s behavior in the Presidential debate), all of which compelled me to write, all against the backdrop of having two daughters and many friends who are female founders, corporate execs and VCs.

The first incident is now known by many of us. A white male VC advised women to hide their gender online and in business communication in an OpEd in the WSJ. Sure what he is suggesting is repulsive, demeaning and would roll back women’s rights but that’s not the worst of it. This man actually thought he was helping women and he was so certain he chose not to get feedback before he posted. As expected he was excoriated and ultimately apologized.

I bring this incident up because it reveals one of the the roots of the diversity challenge. Men still hold the power in tech and many of them, while wanting to be progressive, are clueless about how to do it. Their (and my own) blind spots prevent some from even knowing how vital it is to seek advice from women about how to advise women. I weighed in strongly and publicly here but it was more about what not to do vs what to do. By the way, the feedback I received for this post from multiple women in tech was invaluable.

I can relate to this misguided OpEd experience because four years ago I co-wrote a job description for an analyst/principal position at Freestyle, the venture capital firm I co-founded. Though we’d hoped to attract lots of female applicants to help diversify Freestyle, we only received five. Dismayed but hopeful, I organized a lunch with some of my female friends and they, much to my embarrassment, pointed out that using male-oriented words like “crushing it” would subtly turn women off. I adjusted the language with some nurturing outside editing, and more importantly, recirculated the job post with the help of the women who attended the lunch and we finally found our female hire.

The second incident is lesser known but equally important. Motherboard criticized Elon Musk for not following any women on Twitter and some notable techies from both genders piled on. I actually challenged this attack on Elon for many reasons, the most important of which is I felt that this kind of unsubstantiated critique would actually push “undecided” men to the wrong side of the gender issue. I was called out by several people I respect but that paled before what the Elon criticizers experienced. A mob of men and some women surfaced and lobbed furious, ugly personal attacks at my friends, to the point where they were blocking accounts whack-a-mole style and deleting their own tweets to extricate themselves from the thread.

I bring this incident up because it reveals how polarizing the gender issue still is, even and maybe especially within tech. I received numerous DMs from men and women saying “Man, I agree with you but I can’t believe you waded into this so publicly”. If we can’t have civil, honest dialog about gender then the movement won’t progress nearly as fast as any of us want.

The third incident occurred behind closed doors on Sand Hill. I sat down with a female founder from outside the Bay Area who is in the middle of fund raising. She shared that the “ice breaker” question from the very first VC she met with was “How are you going to compete with all the male CEOs in the Valley”. This question is so wrong for so many reasons, none of which I am going to discuss here. My point is we still have a long way to go. A recent LinkedIn survey to members working in venture capital and startups confirms this: Nearly 80% of female investors have witnessed episodes of sexism in the industry (conscious or unconscious), whereas only 28% of male investors reported witnessing sexism in the industry.

So here is what I currently do to help advance women in tech. Like so many of you, I engage publicly and constructively, 95% of the time pushing for greater sensitivity on women’s rights and every once in a while pushing back against the PC police when I feel they are turning off the very men they want to bring into the fold. We must have a continuous and public dialog about gender because effecting behavior change demands it.

As VCs, for better or worse, we are in positions of power and can truly have an impact, not just with funding but with coaching and advice. Having started and sold two companies, I know how shitty fundraising can be and how “crushing” it is to found and run a startup. I receive far more inquiries for funding and advice then I could possibly answer. All things being equal, I am more likely to respond to and meet with a female founder than a male founder. Since I receive 10x male to female inquiries (used to be 20x), I feel this extra consideration can actually have an impact. And it seems to be working since the last three companies that I have funded are led by women. I should reveal though, that when it comes to actually making a funding decision, I am gender-neutral and treat all founders equally.

We recently made Jenny Lefcourt an equal partner in Freestyle because she is an amazing investor and a serial founder. To be fully transparent, we at Freestyle will also reap the benefits of diversifying our partnership by adding a female partner. While there are in fact more women at tech companies (most in non-tech positions) today than even 10 years ago, it’s happening too slowly and gender discrimination is still all too real for too many. Men need to ask more women about what they can do vs thinking they have all the answers. We need to attack less and encourage more civil, constructive dialog by removing some of the mines that are keeping this vital conversation in the shadows.

You can also find me on Twitter as @joshmedia (

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