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I just want to elaborate on point #4. I chose those examples purposefully: Those three are all well-known business leaders who have dated or married their subordinates. Presumably, there was a point where Gates/Brin/Knight initiated or suggested to initiate romantic involvement.

If as it turns out the woman had not been interested, in retrospect, would the methods of initiation seem like sexual harassment? I believe it's very likely they might.

Again, there are clearly methods that are right and clearly some that are wrong. But I have a feeling the large grey area can be considered harassment if a woman turns out not to be interested, and adoringly recalled in a heart-warming wedding toast if they end up getting married.

If the women isn't interested, you stop. Seems like many men have a problem with rejection and accepting no, that's usually when it becomes creepy.

Had Gates asked his now SO out and she said no and then he politely went on his way like a respectful human being I really doubt anyone would cry sexual harassment.

Haha. You'll want to read the story of what he actually did before making this assumption. If the names were redacted from the Bill and Melinda story, everyone here would be calling for his head.

I don't know, it sounds like she said yes to the first date? Maybe I'm missing part of the story. http://people.com/human-interest/melinda-gates-love-story-bi...

A 34 year old CEO asking a newly hired 23 year old college grad out on a date sounds like sexual harassment to me even if it was just a one time thing.

It certainly raises some interesting quid-pro-quo questions. Every sexual harassment training I've attended has mentioned this as very dangerous territory, but not explicitly sexual harassment.

If a CEO asked a much younger employee out and it made her so uncomfortable that she quit would you still say that it wasn't sexual harassment? Once is still too much. And for all we know Melinda might have felt compelled to say yes to avoid retaliation and only later accepted it.

According to my many sexual harassment trainings, it doesn't meet the definition of sexual harassment under U.S. law. But it is extremely borderline.

I can't find anything other than that he awkwardly asked her out (after dating a number of Microsoft employees). Most of the recent stories read like sanitized rewrites of history.

But I did find this somewhat interesting 1995 history of the lengths they went to in order to protect their privacy:

http://community.seattletimes.nwsource.com/archive/?date=199...

He cornered her in the parking lot after watching her for several weeks and asked for her number. She said no, mentioning something about him not being spontaneous enough. She didn't give him her number.

An hour later he called her at home, having obtained her number through her personnel information, saying, "Is this spontaneous enough for you?"

This is the wealthy CEO talking to a junior new hire.

I can only imagine the mob if someone like Travis Kalanick did that.

According to the standard some posters here are advocating, that makes Bill an evil sociopathic predator that should have been shamed or even locked up for harassment.

Clearly, these simple Dos and Donts are not so simple. It turns out that he made the correct move, they fell in love, and are married to this day.

Had I been his wing man and he bounced that plan off of me, I'd have talked him out of it and said he was crazy. It makes you wonder if he was extremely socially retarded or extremely socially advanced. He took a risk and it worked out perfectly for both of them.

Yet we want to crucify the guy who joked about wanting to hit on someone in an interview. I don't think that was appropriate but I'd be lying if I said I could find where we are drawing the line between what Dave tried and what Bill tried.

> Seems like many men have a problem with rejection and accepting no

Women don't have the burden of having to initiate relationships and chase after potential partners

Men don't either.

Yes, being single forever is indeed an option.

Men should learn to deal with rejection, but let's not pretend that they don't have the burden of initiating. I've literally never been asked out by a woman in my life.

It's pretty evenly balanced in my social circles. Perhaps there is something else at play?

Probably culture.

I've been pretty successful with women in my life; whilst I was nerdy as a teenager things changed and I've since had a lot of luck with women.

In Europe, where I live, I have never been asked out by a woman that I can recall, despite having had plenty of girlfriends here and good relationships. Men always have to make the first move. The most extreme case of this was when I briefly dated a Russian woman. She had recently divorced with a young kid, and was incredibly beautiful - I couldn't believe my luck when we got together. But I kept asking her out on dates, we'd do a date, it'd be fantastic, and she'd go home the next morning ... without suggesting we meet up, or informing me of her plans, or even what she liked to do really. She'd just go home. At the time I figured she maybe just wanted some fun and didn't wish to begin another relationship so soon after ending her marriage. I took it as a hint that causal dating was fine but she didn't want me intruding on her family time. So eventually I stopped asking her out on dates. I was looking for something more serious and was hoping for her to suggest something she'd like to do instead of always waiting for me, but it wasn't happening. I found out later via mutual friends that she was quite upset when our dating stopped and she'd been hoping it'd get serious. Just that in Russian culture, men are expected to take the lead and tell the woman what's going to happen to a much greater degree than in my own culture, and I'd totally misread her.

However, in America, I've been asked out by women. It's a vastly more forthright culture where "sassy" women are lauded and "go getting" is seen as the way forward.

Given how international tech workplaces are, you're getting vastly different dating cultures and expectations mixed together on a daily basis, in an environment where many men don't get to meet many women. I work in tech but virtually all my dating has been with women I met outside of work. But my colleagues often don't have a social life outside of their colleagues.

For what it's worth I'm also European but have lived all over. While I can see your point re Russia I'm not sure it's a geographic thing entirely.

Maybe you didn't meet the right person yet.

I think there is something of a disconnect for some men with changes in what is culturally acceptable when it comes to mating as well as holdovers from traditional structures.

There are definitely women out there who will ask guys out, but I'd wager, based on my own circumstantial and spotty experiential evidence in my culture, that it's men's responsibility to initiate has generally remained the case. I think guys who are less adept socially/are timid have difficulties resolving this facet of dating with the decreasing tolerance for overstepping boundaries--some dudes get wet feet because they realize they have to initiate but scare themselves out of it because, compounded with their inherent difficulties in socializing, they now build up this ridiculous fear-based narrative wherein their social clumsiness leads to misinterpretations which wind up screwing them way harder than a simple rejection.

This fear, of course, is unfounded. But I do think the mating initiator in most cultures, whether it be men or women, often relies on 'primal' methods in order to go after potential mates--aggressiveness, shows of power, confidence...When it comes to mating we really haven't moved far away from the schemes of any of our other animal brethren--yes we have money, cars, nice clothes, ambitions instead of colorful plummage, but things are otherwise the same--the old playbook. When you utilize this with restraint, all is well. When you let power go to your head and convince you that things are more animal than they really are and that this sort of behavior is always permissable you wind up like one of our lovely VCs here. That is still the case, and dating is of course nuanced--you have to utilize these peacock techniques but recognize a rebuff when you see one and cease your little dance. I think some guys fail to see the nuance and then read these stories correctly condemning jackasses for their behavior but lack the social understanding to realize this doesn't mean they should paralyze themselves out of asking others out, be afraid to initiate at all, or live under the tyranny of some ridiculous fear that if they so much as a approach a woman it will yield a lawsuit.

http://www.businessinsider.com/bill-gates-hacked-computers-t...

> If the women isn't interested, you stop.

I feel like this is much easier said than done. Emotions can be complex and fickle. Many books have been written about how to woo a potential mate. There have been tales of love potions for hundreds of years. The dating scene is filled with people who use subtle manipulative behaviour to score.

What I'm trying to say is that it can be very hard to know whether someone is interested. And the success of your wooing efforts determines -- retroactively -- their creep factor.

It's pretty easy to tell if someone is interested in you. It's when you ask them on a date, and they say yes.

If they say no, the respectful thing is to drop it.

Do the respectful thing. This is really uncomplicated. There aren't any "ifs" or "buts" after that. The notion that this is the time to start wooing is absurdly wrong. That's the time to know you've been rejected, and move on.

Accepting rejection, incidentally, seems like something many of these VCs have trained themselves to be terrible at professionally.

>Those three are all well-known business leaders who have dated or married their subordinates.

Here's another one: Bezos! He married a subordinate.

http://www.zimbio.com/photos/Mackenzie+Bezos/Business+Leader...

And she's cute. Cue ball did well for himself.

Apparently she initiated.

Bezos and MacKennzie met while working together at the New York City hedge fund D.E. Shaw.

In a Vogue interview, MacKenzie said Bezos was the first person she interviewed with at Shaw. She asked him out to lunch one day and they were engaged three months later. She was only 23 years old when they married.

“My office was next door to his, and all day long I listened to that fabulous laugh,” she told Vogue. “How could you not fall in love with that laugh?”

http://heavy.com/news/2017/06/jeff-bezos-wife-mackenzie-writ...

That’s a very important aspect. If the difference between inappropriate harassment and the start of a sweet, romantic Pam-and-Jim-like story is the question of whether she‘s interested or not, we are in for a lot of grey area and uncertainty.

Replying to #1, I think you are likely to see this dynamic in any industry where there are huge power imbalances, especially in an industry with tons of aspirants and very few successes (no one wants to jeopardize their potential "big break"). For example, Hollywood is pretty famous for this type of behavior.

People are talking about "sexism in tech", but this case much more about "sexual harassment by the powerful."

It's a lot to do with the culture of entrepreneurship-- to do this stuff well requires taking a lot of risks without a lot of oversight. You can become fantastically successful doing it too, which comes with a whole host of other psychological dangers. And there is an obvious power imbalance at play. AND most critically, it's a culture that is very relationship based, where you don't want to burn bridges. It's not at all clear that the women that came forward, even now, are going to come out of it unscathed. Nobody's gonna come out against them now, but if they want to raise another round next year, who's gonna pick up the phone? I hope it isn't an issue, but if it were, there's no telling why your round didn't clear.

Also want to reply to #4. The thing that differentiates the sexual harassment in most of these cases is that there's a power imbalance. Being hit on becomes much scarier if declining might jeopardize your job or your startup's funding.

That's a fair point, but I chose those specific examples because there was a power imbalance. Brin was a co-founder of Google, where Amanda Rosenberg worked (dated for at least a bit). Bill Gates met his wife Melinda when she was a Microsoft employee (still married, 23 years).

And Phil Knight (founder of Nike) actually met his wife when she was a student in his accounting class (power imbalance #1). He then hired her at Nike (power imbalance #2) and eventually initiated a romantic relationship with her[1]. They're still married today, ~50 years later.

[1]This courtship, and the entire Phil Knight/ Nike story is told in his memoir, "Shoe Dog", which has 4.8 stars on Amazon, is highly recommended by Bill Gates, and is the best business book I've ever read.

Does that mean that powerful men should never hit on women?

A rich and powerful VC is almost always going to have more power than any woman he meets. Even if they're not actively raising money or trying to get a job, he's still a powerful man who could someday offer those things.

I'm not trying to be trite here, but I really do wonder what the line is. Even as a man, I certainly pay attention to my interactions with powerful men (investors, CEOs) despite not currently trying to get something from them. If they hit on a woman in that scenario, would it be harassment?

"A rich and powerful VC is almost always going to have more power than any woman he meets."

It means that he should be very careful in doing so, and in any case never do this in the course of his work - e.g: in the course of negotiating with entrepreneurs, or even co-workers.

I suspect that if this happened in a non work situation, it wouldn't gather this amount of outside attention. Would a tech VC, hitting on a TV anchor or an actress(say) be considered inappropriate, if he has nothing to do with the media business?

I genuinely don't know. But I suspect if he keeps his love life separate from work, things would get tremendously easier.I think "power imbalance" becomes a factor only when a working relationship is involved.

Still, interesting question. I think it behooves anyone who has significant money and/or power to be very careful in conducting their love lives.

My personal strategy is to avoid flirting with or hitting on anyone from the same industry entirely, but I think it's pretty restrictive. People want to have common interests with their partners, and both working in tech is a common interest so I can understand why people pursue it.

It's quite clear that hitting on a subordinate is unacceptable, but when you don't work together it's a lot less clear. Would flirting with someone at a conference party be harassment? What if you were from different companies, but at equal levels? What if you're a VC and she's an entrepreneur (but she hasn't mentioned raising money from you)?

"Would flirting with someone at a conference party be harassment? "

People have been evicted from conferences and lost their jobs for using 'inappropriate' language that some one passing by happened to hear.So yes, I would think this is a dangerous thing to do, and possibly a violation of the conference's code of conduct if it has one.

I agree it's dangerous, but it also happens literally all the time. Do you think nobody hooks up at SXSW?

I made no comment on whether such things 'happen all the time' or not. They probably do (and remain potentially dangerous for the careers of people who do).

My point is that saying they're dangerous (and we shouldn't do them) is not really helpful, since humans being humans we'll likely still do it. Instead, I'd like to think of ways to reduce the harm and make the dynamics less problematic.

Like, in theory coworkers should never date but in practice that's impossible to enforce. So many companies instead enforce a ban on relationships down the chain of command, which is both workable and addresses the biggest power dynamic.

a.) I've worked elsewhere for ten years prior to moving to Silicon Valley and I've never seen anything like what is described in the NY Times article. Also, every company big enough to have a HR department that I worked at also required employees to watch sexual harassment training (how to recognize what not to do, not a how to) videos. b.) The companies here in Silicon Valley that I worked for that were not startups also all had HR departments that required me to watch sexual harassment prevention training videos.

Let me address your #4:

Expressing romantic attraction to someone can be fraught. One party or other usually has to make some sort of leap, and that leap has the potential to backfire.

So. This is why adults learn how to do two things:

- Thing 1: Read the other person. It's entirely possible to take actions that could lead to romance, but that also allow both parties the ability to gracefully back out. Normal people should accept when the other person gently signals disinterest and attempt to restore the previous relationship. So I can believe that someone could form a solid and real romantic relationship with a subordinate.

But:

- Thing 2: Some people are creepy assholes with shit-bag pick-up lines who clearly don't see or care to see the lines between work and romance. These people say things like: "I was getting confused figuring out whether to hire you or hit on you." Normal adults know that this is inappropriate and wildly uncomfortable (at best) for the target. It frankly feels like the actions of someone who has learned about women through Penthouse letters and porn (depending on their generation). It's like a pizza guy who thinks women opening their doors to pay for pizza are offering a sexual come-on.

Executive summary: Trying to establish a romantic relationship with anyone is tricky, especially if you're already in a position of power. But normal, respectful adults know how to do so in a way that doesn't ruin relationships, offend people, hurt people, or confuse business relationships. Generally they do this by not muddying existing relationships and by by giving the other person a graceful out.