My inbox and timelines have been flooded all day with Peter Thiel/Gawker related posts and emails, and below are some unadulterated thoughts — in no particular order, and replete with typos.

The censorship-via-lawyer problem is what most people are talking about right now, and rightly so. The notion that Thiel or any one percenter could wage a war of attrition against a media outlet with the intent of destroying it for slights real or perceived should be horrifying to anyone who believes that freedom of the press is a necessary condition for an open society where corruptions of power can and should be exposed. But as someone who (for the second time in my career) is operating as an entrepreneur and not a journalist, my first thought on reading the Forbes article this morning was unrelated to journalism.

My first thought was that this must make any entrepreneurs working with Thiel a bit nervous.

The whole situation reads like the plotline from an Evelyn Waugh novel — if Waugh had lived long enough to be exposed to two of our most American of cultural exports: professional wrestling and grainy sex tapes. You have Thiel biding his time for ten years, assembling a legal team, looking for as many opportunities to sue Gawker as possible, and then moving forward with the legal equivalent of a nuclear assault that would be financially implausible without Thiel’s extraordinary levels of wealth and Gavin Belson-y inclination to utterly destroy his enemies. And then you have Gawker, which has been, to put it charitably, inconsistent in the way it defines what is and isn’t newsworthy and invariably tends to be defined by its occasional bad judgment or bad taste rather than its occasional admirable displays of bravery or willingness to cover abuses of power and hypocrisy.

Which sometimes pains me as the founding editor of Gawker, though when I was writing it (2002–2003), it was a very different site. It was New York-centric, far less celebrity focused, and I wasn’t publishing sex tapes. If anything, I probably would have paid good money not to ever have to think about Hulk Hogan’s sex life. (And there have been stories Gawker has done that I wouldn’t have. I thought the Conde Nast CFO story was appalling.) My era of Gawker was mostly interested in insider media stuff, and even then, it just wasn’t that scandalous.

But this new situation disturbs me even without my connection to Gawker.

On the one hand, you have to admire Thiel’s sheer and apparently unending determination to make Denton and Gawker pay for coverage he didn’t like — it’s Olympic level grudge-holding. But the retribution is incredibly disproportionate in a way that seems almost unhinged. It would be hard to argue that Thiel was materially damaged by Gawker’s coverage in the way that he’s now trying to damage Gawker. His personal finances haven’t been destroyed and even the most egregious things Gawker has written haven’t put literally everyone who works for Thiel out of a job. (What did Lifehacker ever do to Peter Thiel?) And given his hard libertarian tendencies, it should at least make him uncomfortable in a very prickly way to utilize government bureaucracy to put a capitalistic enterprise out of business.

Even if Thiel wants to argue that Owen Thomas’s 2007 notorious “Peter Thiel is Totally Gay, People” post had a cataclysmically negative emotional toll for him, trying to destroy the entire business via abuse of the U.S. legal system still seems so epic in its vindictiveness that I couldn’t help but wonder whether this kind of asymmetrical reaction is just part and parcel of what you can expect in Thiel’s orbit generally, if you choose to do business with him.

I honestly don’t know if that’s the case. I hope it’s not. I’ve never met Thiel, though I do get invited to his Dialog conference every year, so it’s conceivable that we’re in similar orbits at least some of the time. And I never go to the conference, but admittedly not for any lack of interest. Thiel has been described to me by mutual friends as brilliant and mercurial, and brilliant/mercurial is, well… kind of my type. (Ask Nick Denton, who could also be described that way.) And he would have been someone I’d have been curious to meet, in part because I am convinced that he’s smart, provocative, and thinks in a very long term way about big thorny problems.

But there’s interesting-fun-mercurial and there’s the kind of mercurial where you start to worry about being anywhere near the blast radius when the person blows up, for of being completely incinerated — maybe even unintentionally. And that’s where I wonder what he’s like as an investor in situations where he’s actively involved. If you have a disagreement with him, is the result a reasonable adjudication of the conflict, or is there always a possibility that even small things could result in total annihilation?

And because I know there’s someone somewhere reading this and thinking “well, what the fuck is wrong with total annihilation when someone screws you over?”, here’s what I’d say: there’s a reason why proportionality is an important concept in the ethics of warfare and I think there’s a parallel here. I don’t want to go into Just War Theory/jus en bello rules of engagement or whether it’s a morally correct military doctrine, but if we didn’t largely hew to it, we could easily end up in a “because we can” cycle of foreign policy that allows wealthy powerful nations to catastrophically and relentlessly attack weaker ones for minor offenses. Disproportionate response facilitates tyranny.

And maybe Thiel thinks that “because I can” total annihilation is appropriate. He is, after all, backing a Presidential frontrunner who views “because I can” as a overriding personal and professional ethos that justifies all manner of morally questionable “spirit of the law” violations.

Maybe Thiel exhibits the same kind of gleeful nihilism. Again, I don’t know. But as someone who will likely be fundraising next year for an analytics product that’s squarely in Thiel’s wheelhouse, these are the questions I was thinking about this morning, in addition to the obvious First Amendment issues. As an entrepreneur: how would I feel about working with someone who would do this?

I would like to think that I would know more about whether this sort of thing is typical of Thiel’s behavior because there would be enough evidence of it one way or the other in tech press. But I don’t think there would be. A lot of self-censoring happens in the tech industry because people fear blowback — and in a way that I haven’t experienced in finance or publishing. Entrepreneurs genuinely worry that capital markets won’t be accessible to them if they express any kind of criticism, or talk about the bad things that happen in the industry. (I am not of that opinion, obviously, but as the former CTO of a big tech co told me a couple of weeks ago with a bit of an eyeroll, “you’re not normal anyway, Spiers.”)

Another factor: I think Thiel aside, tech press is largely fawning toward successful entrepreneurs and venture capitalists, and mostly unintentionally. Journalists who haven’t worked in tech themselves are sometimes genuinely and sincerely enamored with the promise of what they’re looking at and are so dazzled that they fail to ask the questions they should. Some of them are lazy and it’s always easier as a journalist to write the glowing lightweight story, where no one’s going to press you to nail down the facts and you won’t get any blowback from sources or subjects. Ultimately, this has created a sense of entitlement in the industry where denizens of Silicon Valley expect the media to actively support them and any negative portrayals are met with real anger and resentment, even when they’re 100% accurate. And it’s never the media’s job to support the industry — that’s PR. It’s the media’s job to cover it, the good and the bad. But if you’re not used to being covered, and that would describe 99% of the tech industry, the scrutiny can be uncomfortable.

Even comic scrutiny. I’m floored at how many of my colleagues vociferously hate the HBO show, Silicon Valley, because they view it as an indictment of their career choices and take it very personally, seemingly oblivious to the fact that satire by definition seeks to caricature the negative — ideally in the hopes that making it more prominent and pointing out the absurdities will result in some improvement. Silicon Valley (the show) doesn’t say that everything in Silicon Valley (the place/industry) is horrible and corrupt. It says that this is what the downside of a boom looks like, and sometimes it can be horrible and corrupt, and sometimes it’s just hilarious.

I think when Valleywag was good, it did that, too, and there’s a place for that kind of coverage. I don’t think outing a tech executive serves that purpose, but if you write down the entire value of the Gawker properties on the basis of their worst posts, you fail to appreciate what it does that’s good and why that kind of journalism is necessary.

I certainly wouldn’t expect Thiel to appreciate that under the circumstances, but I also wonder if he knows what kind of signal completely firebombing Gawker sends. I’m know it’s satisfying to send an epic Don’t Fuck With Me message when you’re angry, but looking at it from an entrepreneur’s perspective, it’s hard not to look at the situation and read the message as, I Have No Sense of Proportionality and Might Go Completely Apeshit On You For The Slightest Infraction, Or If Godforbid We Just Have A Simple Misunderstanding.

It seems unreasonable to me. But then I’m not the kind of person who shows up with a gun when what the enemy really deserves is a good solid wedgie.

Writer, adjunct in the grad school of journalism at NYU, political messaging consultant, ex-editor in chief of The New York Observer, founding editor of Gawker

Writer, adjunct in the grad school of journalism at NYU, political messaging consultant, ex-editor in chief of The New York Observer, founding editor of Gawker