🌻 fit to rule

an anonymous conversation about Donald Trump

As of yesterday, Elon has left the Trump White House to pursue the full-time venture of Twitter canceling his former boss. For many, the fallout of the “tech right” is no surprise. Silicon Valley and MAGA conservatism were always an odd fit—tied more by who they hated than what they support.

I’m still fascinated and befuddled by what drove so many founders and investors to support Trump in 2024. Most of these folks are not deep Republican partisans or racist caricatures; many are even intelligent, well-intentioned, and politically engaged—yet voted in a way I consider deeply and destructively wrong.

I trawled my group chats for someone willing to have a candid conversation. This person is a founder, immigrant, and Bernie-to-Trump supporter. Below, we discuss “country club Democrats,” why founders see themselves in Trump, and why he turned on the current administration. I’m grateful that he spent time talking to me, and hope you’ll give it a read. (As with the last anonymous interview, this person is an individual, not a spokesperson.)

PS: I have a new piece on home-cooked apps in the Wall Street Journal, which made it to digital, print, and podcast!

fit to rule

The interview has been edited for length, clarity, and privacy.

Tell me about your background.

I’m a startup founder. I’m originally from Chile, and grew up across Chile, the US, and France.

How would you describe your political orientation?

Heterodox is one way to put it.

My parents are the children of wealthy, left-leaning intellectuals. I discovered Marxism around 14, and that really opened my eyes. The idea of human dignity really mattered to me. When you read stories of the US factories and the meat producers, it’s fucking nuts.

Bernie announced his candidacy in 2015, when I was finishing high school in the US. He was the first politician who really touched me. I would cry at Bernie speeches. His theory of economics felt so true, about a class being left behind. The 2016 election was very unexciting at first because the polls were all Jeb Bush vs. Hillary Clinton. It felt so trite and boring. Then Bernie announced, and I became a complete aficionado. I had a Bernie Instagram account. It was his authenticity.

My disillusionment with establishment Democrats started during that primary, because it felt rigged. You could see television actively lying about who Bernie was, using sound bites incorrectly, picking favorites. I never felt Hillary Clinton was elected. She was just appointed.

Anyway, Bernie loses. Trump is in the race at that point, and you get to the actual election. At that point, I'm basically a Trump supporter. I always think of politics as having a candidate of hope and a candidate of the status quo. I felt that Trump was the candidate of hope, weirdly enough.

Did going from Bernie to Trump feel like a dissonant thing to do?

No. It was like, fuck these people that stole the election from Bernie. They're not on our side. If you look at where Bernie versus Hillary stood in 2016, she was essentially a Republican in ways that were the worst of both worlds. She had the elitism of Democrats, and also all the bad neoliberal policies that Bernie fought against. The pitch was literally, "My name is Hillary Clinton." And it's like, "Says who?" Trump winning was the revenge of the Internet, in some ways.

Trump 1.0 was very much about immigration. You're an immigrant from Latin America. Was that weird?

No. I wasn't in the US for most of Trump 1.0, so it never came my way. I knew he delayed visas. I never took it as a big deal. My perception of Trump 1.0 was that the first year was really tumultuous, and the other three years were actually really good.

Trump was very radical and courageous with Israel policy. Peace deals, things that the Clinton types would never do. Then he just did it, and it worked. Also, Republicans made the stock market go up for a while. So it felt like a good, interesting government. The counterfactual would have been Hillary going to war in Libya or something.

Trump has this unpredictability, the willingness to do shit that maybe you shouldn't do. That worked with his foreign policy. He knows how to empire.

Where does your populism come from?

The reason I love technology is that I think technology is individualizing. Before technology, you needed other people to do things for you, so it was a collectivist way to see the world. Now technology lets you do things on your own—that lets the people you connect with be a choice, not a need. That's more enhancing to the human spirit.

I think the same is true of populism. There are a lot of people in this country who are neglected and forgotten by this country-club-esque Democratic establishment that cares about the coasts and is smug and condescending towards the center of the country, which, I get it, is poorer and less educated. But they're still people. I feel genuine fury at that kind of neglect. The pitch is always, "Back to normal, let's keep things as they are." But things aren't good for a lot of people.

When do you start thinking of yourself as a “tech person”?

My last year of high school, I made an app and sold it for $40,000. But I thought I was going to be a lawyer. Then I read Zero to One. I was very interested in philosophy. Peter Thiel is a big philosophy guy, and it’s the only business book I've read. It started an obsession with the future that was really exciting. So when I started building technology, I thought, “This is the highest leverage thing to do.”

Then you leave high school and go to college in Europe. How do your politics change there?

There are two things that were very interesting about Europe at that time. One was GDP at 0% growth, which is actually fine. I'm in favor of the European lifestyle; they're generally happy. But it's hard to get jobs, so people stick around in the same job. And there's a "Why are you trying hard?" mentality. To believe in things is how World War II happened, and "We should believe less" is the ethos of Europe. If you think about World War II as a war of ideals, that's why nihilism and existentialism come about. No one was an existentialist or a nihilist during the Nazi era. They all believed their shit. There are some great things that come with belief, but it's certainly more dangerous and violent.

Then I saw the immigration wave happen in real time. In 2015 and 2016, France started to take in a huge influx of immigrants from Syria, Sudan, and other countries. I worked at a community center that housed refugees, and I got to meet them. I saw them being discriminated against, being shunned. And I also saw them make the life of Jews worse, because antisemitism was big and violent in Syria. Therefore there was more antisemitic violence in France. You can put yourself into complicated spots if you take in 10% of your population from countries that don’t “align with your values.” It all happened very fast.

What is the next turning point in your politics?

October 7.

What was going on with your life then?

I came back to the US in 2022. I had just started working on my own startup.

October 7 was the weirdest week of my life. I didn't know anyone firsthand who was killed, but I knew 100 people second-degree. All my friends from Israel knew people. It was really bizarre, a true Trail of Tears of everyone calling me, everyone freaking out, yet life feeling normal or even antagonistic for everyone else. There was not quite the condemnation that you would expect from the Democratic establishment. The left wing of the Democratic Party is pretty anti-Israel, so even before there were tanks rolling into Gaza, they were saying “It’s Israel's fault for creating an open-air prison” or whatever.

That was really strange. I felt sincere sadness in ways that I can't explain. That's when the straw broke. At that point, I was very excited about Trump.

You say the Democratic Party didn't condemn the attack the way it should have. What did you expect from them?

If something 9/11-scale happens, you would expect that there wouldn't be an "Oh, however..." There was relativism. But there was also a lot of formalism. That was the feeling I had with the Biden administration. It was country club formalism: We will say the right things, we'll write the right statements, we'll tweet a certain way. It's so fabricated and so inefficacious.

A lot of why I was very much pro-Trump by 2024 is that I thought the the war in Gaza was terribly handled by the Biden administration. Counterintuitively, I think it could have ended much sooner if they had been clear about their support of Israel and an aggressive but fast engagement. Then you wouldn't have the food insecurity that we're still dealing with. Hamas is a terrible, murderous government, but there are two fucking million people it rules over that need to live, who have dignity.

Once again, I thought that the established country club types are not fit to empire. They're not fit to do the right thing. They're inefficacious. And we need to find a new way of doing things.

You mentioned the left equivocating in response to October 7. But I don’t think the Biden admin said that stuff.

No, the official admin would not have said that. But funny enough, it was more frustrating. Because they hold the reins. The left can be mad, because they don't win. But when you hold the reins of power, and you're focused on formalism… like, what the fuck? That's where it hurts.

I left my old tech company job because there were a bunch of random formalism people who were there because they had a job before that looked like the one they have now. But they weren't actually good. They just knew how to say things a certain way, and it fucking pissed me off. I felt that in college with people that went into traditional roles. They did the right things, and now they're investment bankers. These people should be brought down.

I've always been interested in revolution. I think technology has a revolutionary angle: it's the destruction of something as well as the construction of something new. And to me, the Democrats’ genre of politics feels like the exact thing that I hate most, which is stagnant, unearned elitism.

What do you mean by “fit to empire”?

Establishment Democrats never had to earn their position, they were just maintaining a certain status. They never understood what it takes to get there.

There's a general discomfort in the language of establishment Democratic politics in saying the things that have to be said. A great example of that is Trump 1.0's negotiations with Iran. Being a strongman actually works in a way that “Best regards, Joe Biden” energy doesn't.

There's something middle-manager-y about it.

Yes. "We ought to analyze… Let's pinpoint that." Middle management language prevents you from thinking the things you need to think to rule effectively. And it's important. If the US doesn't do things, wars can start. You have a responsibility to do what's right.

I just felt like these people were messing with the lives of billions of people and millions of Americans for some country club status, as in, "I said the right things. It didn't work, but I said the right thing." Moral purity, even though it's deeply morally impure. There's no logic behind it. It's all agreements within these small groups, and they get to run the country because MSNBC told them to. None of this shit makes sense. I believe the internet is the Cassandra, the bearer of the future. And it frustrates me when you have stagnant institutions running the show.

Was your feeling of isolation just about October 7, or politics in general?

Politics in general. You have to remember it was also peak wokeness. I'm a fan of woke, but it became very Stalinist at some point. Trump said shit that was obviously true, that you were not supposed to say out loud. Like I don't actually care about the border being open; economic immigration doesn't bother me at all. But it should have been communicated that there's a lot of immigration happening.

Then there was the exhilaration of seeing tech people support him—people I respect. I respect Peter Thiel deeply. I think he's one of the smartest people alive. I don't respect Elon Musk, but he's very efficacious. After everyone started to turn for Trump, I saw the TikTok where he stood up and said, "Fight." It was a moment of exhilaration. You had this fragile, clearly misplaced candidate in the shape of Joe Biden, and then you had this guy saying, "Fight," and I was like, "Oh my God, we have hope. We can actually take our country back."

That's how it felt—a release from this Ring of Fire Stalinist club that you're not invited to and you can never be part of. It doesn't matter how rich you become, you need to say the right things. It ended up being the Democrats’ downfall, because they picked a candidate that said the right things but was deeply incompetent.

Were you talking with your friends about Trump?

One of my investors became a very big Trump supporter. He was someone I'm thankful for forever, because he was one of the few people that spoke for the State of Israel after October 7. He made me feel heard and seen.

My founder friends were admitting to ourselves, "This is an administration that can think like we think." Mavericking, doing whatever it takes, doing what's hard, earning instead of receiving or being appointed. There's something about empire, about acceleration, like, "We can just do things, we can change things." Maybe we take Greenland, and that'd be fun and cool.

There's a real moment of euphoric exhilaration. Everyone around me is finally communicating that we feel this way.

Of your tech friends—and I understand this is a self-selecting group—what was the fraction of people who supported Trump?

By election day? 100%. Almost everyone.

There was a group of tech people who are Trump supporters, except they’d never admit it. They're trying to preserve their elite country club status. They'll share Trump memes and adopt right-wing Twitter lingo. They talk about the policies that they like, and they're all Trump policies. But they won't say, "I'm a Republican." So it's a MAGA-coded elite, an "if you know, you know" thing.

You can see that with the American Dynamists. They all say they'd vote for Kamala. I went to this American Dynamist party, and they were shouting U-S-A! U-S-A! These are small skinny guys like me. They're all twinks, but pretend that they're pro-military, tall, jawlined, blonde, fascist guys. There's a lot of LARP and status-seeking. At some point, the tables turned and it was cool to be right-wing in Silicon Valley.

Where are these conversations happening?

Group chats, parties, DMs.

And these are mostly founders and investors, as opposed to tech employees?

Yeah, mostly founders and investors. Powerful people.

Correct me if I’m wrong, but it sounds like there was some identification with Trump.

Huge identification, of course. The guy was a contrarian. Think about how much he was clowned in 2015. People said it would be the worst presidency in history. I don't know if it was a good presidency, but it was certainly a great presidency. Warp Speed was an insane operation. Normalizing deals in the Middle East, that’s hard. Not going to war. People said he couldn't come back as a felon. Yet he still had the will to win—this shit is inspiring for Fountainhead types.

One thing that I'm hearing myself say is that not at any point am I thinking about policy. It's all aesthetics. I think Democratic stuff is bullshit because the aesthetics are wrong. There are some policies that I don't like, but ultimately, it felt like the wrong way to do things.

I was going to ask about that. It's like if you're a VC, you're investing in a person, not an idea. Their ideas might change. They say they're going to build X, but who knows what they're going to build? If the person has the right attitude, if they have the grit, if they have the whatever-it-is inside of them, that's what you're voting for. That's what you're investing in.

Yeah, that is exactly correct.

At this point, when people say that Trump's going to be really bad on tariffs or immigration or democracy, what are you thinking?

It’s liberal tears. It's literally, "The guy says stuff. I don't think he means it." You're trying to attack the guy, and frankly, I think your policies aren't very good either. Apparently, the American population agreed with me on that position.

Then Trump wins. You celebrate.

One of my friends threw a liberal watch party, and I didn't attend because I knew that I'd be crying with happiness at getting our fucking culture back. I was extremely excited. I was on the group chats. I called my father and I’m like, "Finally. The US is a declining empire no more.”

Then it starts to go south. Before Trump takes power, actually, when the DOGE thing happens. In his acceptance speech, he's like, "Elon, a star is born.” And, okay, Elon is here. Then the DOGE meme starts, and that's a little weird. I like jokes, but ruling is serious business. Then tech people I know start to work at DOGE, and they're the least talented, most sycophantic, most status-oriented founders and builders that I knew. Big claims are starting to be made. Trump wanted to do things that I didn't agree with.

Which claims or actions did you disagree with?

DOGE claimed "We're going to end the deficit." And if you look at the charts, most of it is Social Security. I think Social Security is good. Again, human dignity. So that started to get disconnected from reality. You're on a high of winning, then you look at the facts, and they don't quite match.

Trump’s rhetoric against colleges starts to get more aggressive. I visited Columbia when the protests were going on. I think the Columbia campus is antisemitic. But scientific research is important. I was really excited about the "burn it to the ground" stuff, then you start to realize what "burn it to the ground" means. It starts to freak me out.

When Trump takes office, all hell breaks loose. You get the ICE stuff. I see videos of immigrants being put in handcuffs and deported on a plane chartered by the US government. That's the point where reason came to my senses.

The other thing that made me dislike the administration as much as I do now is that I didn't realize how sycophantic people around him had become. I believe in the guy leading the thing and getting ideas through. And I believe in the Jared Kushner sort actually making it happen. But I don't believe in the Mad King theory of, "you should tear up the entire world," and then people build that as prescribed. That sycophantic nature of not having the feedback loop, not having any grounding in general. Seeing Republican policy just fall apart very quickly was just... you couldn't be a reasonable person and support those policies. They weren't good. The sycophancy overruled anything else.

The Trump admin started to feel like its own version of Stalinism, in a much worse way. Say what you will about the country club Democrats, but they're not efficient, so there's less harm done. And norms aren't always bad. If someone committed crazy financial fraud, as the founder of Nikola did, they shouldn't be pardoned because they made a political donation. When Trump launched his crypto coin, I was like, "This is banana republic shit." They wouldn't even do this in Chile. This is where I actually believed the fucking stupid Democratic stuff about “the corrosion of the office.” I thought Clinton was bad. I thought Hillary was bad. If I don't think this is bad, I'm a sycophant and I'm an idiot.

As Trump 2.0 comes into power, you realize there are parts of the system that you want to preserve. But what did you want to burn down?

What I thought was important to change was foreign policy. The US is an important peacekeeper. I think Iran getting a nuclear weapon would be disastrous. I think the war in Gaza ending as fast as possible and finding a solution for the people there was really important.

Those are the specifics. Then there’s the general idea of, "We can do things." Just because things happen a certain way doesn't mean they always need to. The possibility that things can change is not an establishment Democratic belief. If you brought up, even as a joke, in 2022, "You should take Greenland," you'd get a three-month lecture on the ills of colonialism or something.

I think differently because I'm a product person. I was talking to people about soccer. And I was like, "I think soccer would be more interesting if you made the goal bigger, because then there would be more scores, because it always ends at 0-0, and that's boring." Most people don't think about changing things. It’s the Thielian, Trumpian way of thinking. This system was established by someone else, and you could just change the variables.

Do you think you underrated the possibility of things changing in a bad direction?

Definitely. There were things that I assumed they wouldn't do. Like I think scientific research is good. Do I think the vaccine mandates were good? No, they were terrible. But was having vaccines good? Yeah. I assumed there would be more intelligence and critical thinking at the table. And there wasn't. It was one of the craziest things I've ever seen, the sheer stupidity that took over that administration.

What are your conversations like with founder and investor friends now?

“Boy, oh boy did we not know." It's like when you invested in a company that... it feels like post-SBF, in some sense. I think it started with the deportation of Mahmoud Khalil. He went to Columbia, he's an elite student. There's a heart surgeon who was deported as well. It started to get a little close to home. Then it started to actually impact business. It got hard to get visas, and tech likes visas. This stuff started to be very clearly misaligned with our interests.

Are people now saying, "We made a mistake?"

Definitely. The thing about this ruling style is that it burned a lot of bridges. So it’s just like, "The tariffs were stupid, and we don't know what to do now."

It's funny, though, the culture of right-wing Twitter energy is still present. We're definitely not back to Woke 2.0. But at least it's easier to not support Trump. This wasn't true a month and a half ago. I went to this hacker house where a friend of mine lives. Someone was talking about the DOGE engineer who put the union stuff on Github, and he was shitting on the journalists finding out that he did this. And I was like, "No man, I know the DOGE guy. He's a shit engineer, he was a shit founder, and now he's a shit government employee. And sure, we can union-bust. But do it right."

What do you want to see from politics going forward?

I'll go back to Bernie. Bernie was the first politician that touched me, not just because I think the economic policy was interesting, but because he had authenticity. You kind of get that with Trump's strong-man energy, but you also lose it, because he's such a cultist.

I think it's important to understand that things can be changed. I want to see less of the belief that what we have now—the normalcy—is good. It’s not. The US is a powerful country. It can choose to exert that power in ways that are good, or in ways that are bad. But doing nothing is perhaps the biggest of all injustices.

Thanks for talking. I’m happy I had this conversation.

I’m interested in speaking with more people on the “tech right,” even/especially if you have a different story of how you got there. If you’d like to chat, email or Signal me at jws.51.

Best regards,

Jasmine