Dec 16, 2016 · 9 minutes

Two years ago, the tech world erupted into one of the ugliest gender-related scandals it has ever seen.

Serial entrepreneur and one-time wunderkind who sold a company to for $40 million at the age of 16 and another one for $300 million at the age of 25, Gurbaksh Chahal pled guilty to misdemeanor battery and domestic violence charges for assaulting his girlfriend.

This was a good outcome for Chahal. He originally faced 45 felony charges for hitting and kicking her an astounding 117 times over the course of half and hour. A video captured it, but that video wasn’t allowed in court because it was seized illegally from his home. This past August, he was sentenced to a year’s time in jail for violating his probation. How? By attacking a second woman in his home, kicking her ten times.

The Wall Street Journal further unearthed a second outrage against these women-- and all victims of abuse-- when it reported how the company’s board scrambled to save RadiumOne’s IPO amid these horrific allegations, so consumed with greed, they strategized to “minimize the fallout.”

At the time the scandal was erupting, we didn’t write much about it, and I kept getting asked why. After all, I don’t tend to hold my tongue when it comes to bad behavior in tech or misogyny of any kind.

Simply put: I didn’t have any additional inside knowledge of the situation, didn’t know Chahal, and I didn’t have much to add other than the horror that so many others were reporting. Instead, I tried to amplify the other great journalism I saw, because I frankly didn’t know what more to say.

That changes today. Because yesterday I taped an episode of Press:Here, where one of the guests was Nin Desai.

Desai is the CEO of NIN Ventures, the little-known Chicago-based venture firm that made headlines recently when it hired Chahal as an advisor.

Press:Here host Scott McGrew said he was stunned Desai agreed to appear on the show, and he couldn’t have been clearer with Desai that this topic would come up on air. He fully assumed she’d cancel or not show up. But there she was in the chair a few minutes before we started to tape.

I was shaking before this segment. And I was stunned they'd booked me to appear alongside Desai, given they wanted the exchange to be respectfully restrained. They know me.

When I read that news that Nin Ventures had hired Chahal, it was more than just a disgusting fig leaf of respectability applied to a man caught on tape savagely beating a woman. It also summed up two horrible things that seem to be getting worse in tech.

The first is that there always seems to be a second chance for men who’ve had any level of success. The elevation of “track record” over the way a founder behaves towards others. Whether those others are  children (in the case of the most lionized of all tech bad boys Steve Jobs) or women in the case of so many others is excused and tolerated and swept under the carpet in ways that increasingly disgust me. I’ve argued all of this and more in a 4,000 word story about asshole culture and why I think this is getting worse, not better, in the Valley.

The bro culture has not helped, nor has a broad mainstream hyper masculinity in which we see in Travis Kalanick breezily referring to his company as “boober” because of all the women he gets; in which we see in Donald Trump saying he couldn’t have sexually assaulted all those women who came forward because they weren’t attractive enough; in which we see in the he may have been convicted for rape but he’s “not a rapist” excuses made for Brock Turner; in which we see in the “oh, he was just in college then, that’s what they do!” excuses for Evan Spiegel’s degrading college emails.

We see it too in the hyper-masculinization of teenage boys, where “nudes” are demanded of 13 year-old-girls to exchange with upperclassman for liquor. As Nancy Jo Sales detailed in her excellent book, if the girls don’t provide nude pictures, the boys will pick a photo of a random naked girl online and say it’s her.

That’s only a cruder version of the threats of oppo research or made up smears that have been made by the tech bros when they don’t like what critical (typically, female) reporters write about them and can’t silence them any other way.

And why not? Our President Elect so bullied Megyn Kelly that Fox News had to explain to people on his campaign how it would hurt Trump’s chances if she got killed.

Tech elites act so horrified at this behavior of teenaged boys or the President Elect. But when it’s one of their investments, they simply look the other way and whistle. And there was no greater example in an era defined by a lot of violent and disrespectful misogyny than Chahal.

He was caught on tape. He pled guilty. These are not some vague allegations. If there is one man the industry should turn its back on -- even if it’s only pretending to give a shit about women -- it’s Chahal.

Which brings me to the second social trend in tech that horrifies me. An utter lack of empathy. An inability to care if it’s not your daughter (or you) being beaten by a tech bro. An inability to worry about, say, someone else getting raped or someone else's children being threatened, or an app being used for teen bullying, or someone else’s address being released by gamergaters. Or if the rules you benefitted from change, once you’ve already gotten yours.

The most extreme example of this may be (Pando investor) Peter Thiel-- an immigrant, who has also made his money by doing business with other immigrant founders-- supporting the presidency of a man who fanned some of the worst xenophobic and racist flames to get elected.

Tech leaders have made so much money, have so much power, and have become so insulated in the last few years now that a handful of companies are vying to be the first trillion dollar corporations and hundreds of companies are valued at north of $1 billion, that they’ve numbed their ability to think they could ever be a victim anymore. A true victim. Someone who can have everything ripped away from you in a moment of hate and violence. Not merely a rich dude who occasionally gets negative press.

This week, I was reading Mei Fong’s excellent “One Child: The Story of China’s Most Radical Experiment.” One very smart thing she did was to ask everyone who defended-- even lauded-- how necessary this brutal policy was for China how many kids they had. Guess what? Most of them had more than one child, despite talking up the hard sacrifices that everyone else should have to make for demographics and the environment.

I see that kind of thinking over and over again in Silicon Valley right now. It’s as if these great minds got stuck in time, in the early Internet era, where they were just making software that might only cancel your airline tickets if it glitched, not say, put you in physical danger or make a drone fall from the sky or influence the presidential election by spreading fake news stories and conspiracies.

I bring all this up, because what Desai kept saying fit this pattern: Chahal was a “gentleman” in all of her personal experiences with him. The unspoken logical extension of that thought is: So I don’t care about the women he wasn’t a “gentleman” with.

Again: Chahal’s behavior wasn’t even anecdotal like Trump bragging he grabs women “by the pussy.” Chahal’s violent behavior was captured on camera. He pled guilty. And then allegedly he did it again. He is going to jail.

Please, can there be some things in 2016 that we don’t normalize?

The other journalists on the show, and I kept asking -- trying in vain-- to understand what we were missing here. Why Nin Ventures thought hiring Chahal was OK.

Did he invest in the fund? No.

Did she somehow owe him a favor? Not that was apparent.

How does she explain this to potential portfolio companies? By emphasizing how smart he is when it comes to ad tech.

I brought up the Mike Goguen lawsuit, something that his attorneys have argued was a consenting relationship. I brought up the fact that Sequoia’s partners were stunned by the allegations that he’d kept his mistress as a “sex slave.” That Goguen too had never seemed like “that kind of guy” to them. That they’d had a very long partnership with Goguen. And that -- let’s be honest-- people would still pitch a firm as powerful as Sequoia no matter what horrible things its partners did in their personal lives.

And yet, Sequoia immediately fired Goguen after the allegation was made, even before his lawyers responded. I brought up this example and asked Desai why her firm should hold itself to a lesser standard.

Again: The reasons given were she’d never known him to be anything other than “a gentleman,” and he knows a lot about ad tech. So do a lot of people, I argued. We do not live in a time where only a few people have sold a company for $300 million or more. And I’m only aware of one sentenced to jail for violating probation after allegedly assaulting a second woman.

When the show is posted, I’ll embed it here. [Update: The video is here.] If you live in the Bay Area, tune in to watch it on NBC on Sunday morning. But I can say from the interactions I had after we wrapped, Desai seemed genuinely stunned at our collective outrage. And I simply don’t know what to make of that.

Except to say there is something so broken about not only gender in our country with all the micro-aggressions, unconscious bias, and men making eye contact with men in meetings and not women, sure. But there is something also so broken about our rationalization of sexual assault or other physical assault against women, as a nation, and corners of the tech industry aren’t too smart, liberal, elite, or “woke” to be above it.

In 2016, a man can be accused by a dozen women of sexual misconduct and still get elected president. A Stanford swimmer can get a light slap on the wrist despite witnesses to a horrific sexual assault and a victim who cooperated fully with authorities. A man like Chahal gets a job again despite the fact that he’s sentenced to jail. And a woman hiring him seems stunned any journalists are asking her how that’s even possible.

The message from our politicians, our judges, and at least one member of the venture capital industry is clear: We simply don’t give a fuck about your pain because it is not ours.