Dec 9, 2016 ยท 6 minutes

Since about the time Peter Thiel stunned the Valley by breaking its group-think ranks and agreeing to serve as a delegate for Donald Trump, I’ve been hearing a common refrain from senior folks in the industry: “He and I haven’t spoken.”

Max Levchin, said as much on stage at Pandoland last summer when we asked the passionate pro-immigration defender… who co-founded PayPal with Thiel and is one of his closest friends. When asked about Thiel’s decision-- given his entire wealth pretty much came via working with and selling his company to immigrants-- Levchin said they hadn’t spoken.

I’ve had at least a dozen conversations like this since. Whether it’s Thiel or the latest rumored convert to the Trump camp, David Sacks, or other Trump-leaning members of the PayPal mafia. “Truthfully, we haven’t spoken about it…”

I’ve spoken to exactly one person -- also off the record so I can’t share who-- who admitted to having a lengthy debate with Thiel. Everyone else in the Valley is seemingly simply too busy to reach out to some of their closest friends and ask how they could take a political stance that they feel is at best unpalatable, at worst downright dangerous for the planet.

This isn’t a coincidence, and it isn’t a matter of everyone is too busy. Silicon Valley’s strength is its interconnected network of previous co-founders, investors, employees, college buddies and neighbors. It’s the serendipity of continually bumping into so many tech folks that gives the Valley such a multi-decade track record of excellent returns. You can bet if you substituted “Trump” for the next hot startup seeking investment, these people would all find plenty of time to hop on the phone with one another.

This is a continuation of a recent trend in the Valley against ruffling feathers. Long gone are those antagonistic days of Larry Ellison and Scott McNealy where competitors would trash talk one another. It’s all off the record and behind everyone’s back these days. Everyone is keeping their head down, running their own race, and claiming the market is big enough for everyone. Everyone is “a big fan” of everyone else.

Of course in a Valley where CRV was one of the only VCs to -- as a firm-- denounce Trump, no one is going to pick up the phone to Thiel and ask him to explain himself. Reid Hoffman-- yet another friend of Thiel’s-- said as much in the run up to the election. From an article in the New York Times with Andrew Ross Sorkin:

But Mr. Hoffman said he almost didn’t make his political views — and the card game — so public because he worried, as did his family and friends (who originally counseled him against it), that he might become a target for Mr. Trump and his Twitter account — or worse.

“People are fearful that, especially in a circumstance where he might be in a position of extreme power as a potential presidential candidate, that that would be used in a retaliatory way, that would be used in vengeful way,” Mr. Hoffman told me in an interview. “Everyone gets worried about being attacked, and part of the logic and mechanics of bullies is that they cause people to be fearful that they’ll be singled out and attacked.”

Mr. Hoffman continued: “It’s the same thing like on school grounds, when people won’t go help the kid who is being bullied because they’re worried that the bully will focus on them.”

Mr. Hoffman articulated a view that is often whispered within the business community — among those who are voting against Mr. Trump — but rarely spoken aloud. I have talked to some of the top executives of the Fortune 500 companies in recent months, and I’d be hard-pressed to name one who didn’t at least roll his or her eyes when Mr. Trump’s name was mentioned.

Technology companies are afraid that Mr. Trump might criticize their approach to privacy, as he did with Apple. Wall Street banks worry he might seek to break them up. Health care companies are nervous that he might attack them over pricing. Multinationals are worried about trade. All of these are valid issues on the campaign trail — but with Mr. Trump, unlike other politicians, the criticism seems more personal and vitriolic.

That makes sense when talking on the record and on behalf of an organization (sort of.) But that doesn’t explain the fear in having private conversations between partners and close friends.

Even when companies engage in unquestionably bad behavior, the Silicon Valley of today is mum. When Uber, for instance, threatened to go after the families of critical journalists-- starting with me-- there was a mix of silence and “Well, I’m sure they didn’t mean it.” When a court subsequently had to order decryption of emails to prove that Uber did indeed engage in these kinds of tactics against another critic, there was deafening silence throughout the Valley. Instead condemnation came from the judge who described the tactics as “possibly criminal.”

What few voices that do rise up to question the motivations of some folks in tech are frequently squashed by tech’s apologists. For example, this Jessica Lessin column where she argued that tech billionaires have a right to simply be heard and not questioned. As Paul pointed out, the architects of the greatest communication platforms on the planet have plenty of opportunities to express themselves. And given they do control the greatest communication platforms on the planet, we have a duty to question them, not treat them like Kindergarteners whose self-esteem we’re all trying to boost.

In the void of real conversations, we have the ever increasing genre of Peter Thiel Fan Fiction where East Coast journalists pretend to get inside his head and come up with explanations for his actions.

To be clear: I get the human inclination of this. Leading up to the election I couldn’t bring myself to ask my parents who they were voting for. My five-year-old wanted to know and couldn’t understand why I found asking them so hard. He may not yet realize that I ask uncomfortable questions for a living, but he certainly knows I do around the house. I told him that “sometimes something is so important to you, and you love someone so much, that you just aren’t sure you can handle it if they don’t agree with you.”

He pushed me until I agreed to ask them, and I was glad he did: It turns out my evangelical, conservative parents did switch parties. And while it wasn’t enough to deliver Tennessee for Hillary Clinton, it made a massive difference to me personally. I can’t imagine traveling home for Christmas to see parents who voted for hate and bigotry.

But that is a family. And families are messy. Silicon Valley-- despite its chumminess-- is business. And this business is theoretically based on making high-risk bets based on who people are, what they value, and what they’ll do when the chips are down. We talk up the importance of trust, transparency, and being direct with one another. But increasingly, we’re an ecosystem too uncomfortable to have real conversations-- in public or private.