That's rich. People who think like that should really take some time to read a few first-person accounts on sexism and misogyny in tech industry. Once you've read about how women have to worry about their appearance and behavior on a daily basis just to be able to somewhat tone down the sexism they're exposed to, men's complaints about how they might have to start worrying a bit more become laughable.
To illustrate, here's an excerpt from the Forbes story making rounds on Twitter [1]:
Unlike my male peers, who could wear anything from jeans and a hoodie to a well-tailored suit, I had to choose my attire carefully. Feminine but not sexy, structured but not form fitting, classy but not too expensive, lest I imply that I was bad at bootstrapping and not "scrappy enough," professional but not so stuffy that people would assume our product lacked creativity. My hair was almost always worn in a bun or pulled back conservatively.
During the ten years that I worked in international development, clothing was a tool to defuse gender, a strategy for gaining access to an almost exclusively male professional environment. We referred to it as "taking on the third gender." For all its self-regard as the most forward-thinking place on earth, it seemed I would need to use the same tactics in Silicon Valley.
[1]: http://www.forbes.com/sites/jeffbercovici/2014/08/07/what-it...
If you're a VC, you should be adept at assessing risk. If you think that the "risk" of working with female founders outweighs the potential upside, you're definitely not going to be touching my money and I'd rather not have any of yours.
If they're not outright bad investors, they are at least investing a suboptimal way.
Not saying, of course, that this justifies any kind of harassment, just that maybe some of these investors have learned in the hard way that their judgment gets clouded when dealing with women.
Where did you read anything about gender in that reminder from Jessica? That was guidance on behavior. I'm sure YC has strong positions on racism, but that doesn't in any way imply that VCs should be concerned about working with founders from different races/ethnicities.
Just don't be a jerk, and you'll be fine.
Personally, I see where you're coming from. I learn more about how sexism manifests itself in the tech industry every week, it seems. Even with good intentions and a lot of conscious thought about the issue, it doesn't seem extremely unlikely that some action I previously considered harmless could be taken the wrong way.
You can't assess that via the internet. You have to meet them.
Best take him to the gym and do manly guy things like working out and hanging out in the steam room to prove his masculinity.