If they have standards of conduct (probably codified in some employee manual) there are probably contingencies for this exact circumstance which allow them to fire him.
No court would consider him guilty of anything for a joke about a dongle.
I doubt his company had a sexual harassment policy that was substantially more aggressive than what the law provides.
If she asked him to stop, and he kept going, then I'd say that he did something wrong. If he made a dick joke, then no. People make dick jokes in semi-private conversations. Women do, men do, because dicks can be funny. If she says "I wish you wouldn't make jokes like that around me", then he should have stopped and would be in the wrong, but I've seen no evidence of that.
The termination suit is uncertain. It's far from a slam dunk, obviously, especially since he admitted making comments that he considered wrong and embarrassing. Bad move to discuss this in the public so soon. He should be able to get defamation, at least with good enough odds to get a settlement that'll cover him till he gets his next job, given what PlayHaven's management said about the termination and about him.
I'm not an employee of playhaven, but I'm sure new employees sign employment agreements. Usually those agreements reference standards of conduct and that violations can result in termination. The court would have to establish that the employment agreement is null and void, which is a much harder challenge.
"I doubt his company had a sexual harassment policy that was substantially more aggressive than what the law provides."
What we don't know is if employees of playhaven complained about his banter. If they did, and he was informed and asked to stop, then it's his fault.
"He should be able to get defamation"
He might get defamation from her but not from PlayHaven.
(a) mr-hank did or said something sexually inappropriate. (He lost ground by admitting some degree of guilt on HN. Otherwise, it'd all be hearsay and he could say he was just talking about a literal dongle.)
(b) mr-hank's conduct was so bad that there was no choice other than to fire him: "having to let this employee go". It wasn't we decided to fire him. It was we had to fire him. Important distinction, and quite likely, technically false. They probably fired him to save face, not because of an objective violation of any law or ethical principle that left them no other option.
It's not a clear-cut case, and it's less so in the light of his HN admission, but he can certainly argue that the press release (a) misrepresents his behavior, (b) in a way that will damage his reputation and future employability.
He has a lot of options here. He may settle for an amazing reference and introductions to investors. Or he might get a six-figure sum out of it. Or he might walk away. Depends what he wants.
PlayHaven fucked up big time. These companies (especially PlayHaven; SendGrid has more of a case) should be more embarrassed than the people involved.
Honest question: if you essentially blackmail someone for an "introduction to investors" what makes you think the person introducing doesn't pull them aside before or after and say "this guy basically threatened to sue me if I didn't introduce him to you"? I have to imagine anyone in that position would likely do that, you could never prove they did it, and the investors would likely in no way take you seriously. That seems like the worst possible parlay I can imagine.
You get that in the settlement contract, two-way non-disparagement including your right to see any communication about you, that must be furnished in writing.
That's impossible to perfectly enforce, but if you suspect he's talking off the books, you trap him and hit hard for breach of contract. He should know that you intend to be checking. He should expect that and be careful. It's your job to make that so. You might not be able to catch all cases (he might say things to people he really trusts but not to everyone) but you can have some degree of a chilling effect on negative communication of the sort you described.
Also, what's better for him, once the contract is signed:
1. Make the introduction and leave it alone, or:
2. Make the introduction, then backtrack, making himself look inconsistent and weak to that investor? ("Yeah, I wasted your time, and here's why...")
He cares about his image in front of that investor, and will probably prefer (1). This assumes he doesn't hate your guts, which he might. That's a danger of doing the right thing.
What if the joke were "Why did the chicken cross the road? To get to the other side!" and she said that jokes about chickens made her uncomfortable. Is he obliged to stop telling dumb chicken jokes?
I see this case as two people and two companies who acted like children and both lost their jobs and look bad in the community, respectively. Some unfunny man made a joke to his co-worker because he thought it might have eased the social tension that comes from traveling, lodging, and attending a conference with another person over so many hours. An overzealous woman took offense to an overhead comment and saw it more constructive to bring attention to the public conversation that happens on twitter rather than the public conversation happening in that room because it was a more comfortable way to make sense of how she felt.
We're humans and we naturally want to surround ourselves with people who think, act, joke, argue with, and support other people like we do. It's pretty easy to never have to deal with groups we don't agree with on the internet. It's the reason swarms of misogynists got together on the internet to hate Adria and say she represented all the other women that they hate, and to call her awful names and issue a DDOS attack against her parent company.
Both of these companies looked past the human error in all of this, and enforced their zero-tolerance policies, and just fired both of them. This whole thing is a big deal because the other people we align ourselves with and allow to represent us (be it as employees, or pythonistas, or dirtbag misogynists) are making it really hard to connect on personal levels, and really easy to generalize and dehumanize issues into meaningless black or white distinctions.
If someone finds my breathing offensive, am I an asshole if I keep breathing?
I'm specifically ignoring the action of the companies, the firings and all that, because honestly, while I haven't heard the specific joke in question, it really doesn't sound offensive to me, and it seems as though Adria just decided to be offended by it, and while I'm wary of making assumptions (and even mr hank himself seems apologetic), I can't help but be thankful that it wasn't something I said. I was at PyCon, had conversations, and might have even made a joke or two. I don't think I said anything that might have come off offensive to anybody, but given how innocuous this whole thing seems to me, as somebody who admittedly hasn't followed the story, I just can't help but feel some great travesty happened.
When I do offend people, I often like to probe as to _why_ they're offended. In my experience, most people seem to be incapable of defining any concrete reasons as to why a given statement is offensive other than circular, "it's offensive because it's offensive" reasoning.
I think if someone said "Could you stop using words containing "e"? Such words hurt my brain." I think I would.
If someone said "Quit your "e" words, you bad guy!" I'd be less inclined to. "Words with the letter "e" are bad words, and you need to stop using them" even less (the difference between these two being hypocrisy).
Either way, I find it highly unlikely that I would even try to craft e-less sentences, regardless of how offensive someone might find it.
I imagine you're capable of understanding why they might find it offensive and acting accordingly depending on the context, which is the real issue. Whether YOU find it offensive is just beside the point, as it's a given that a person doesn't stand around saying or doing things that they find offensive. Whether you're capable of evaluating the other person's point of view is the key. (I bet you probably are)
If you can see why they'd find it offensive and continue doing it, you're pretty much by definition being an asshole. That's not a moral judgment, I think it's just descriptive...