Coming of age is never easy, but coming of age in Silicon Valley is especially weird. Between applying for Thiel Fellowships, courting VCs, and getting recruited by Palantir at the career fair, today’s young tech workers are entering a world deeply marked by the previous generation’s mistakes. But they’re also joining the industry at a time of genuine disruption, with business as usual facing challenges from below. Unprecedented numbers of tech workers are organizing their workplaces and new algorithmic justice movements are achieving real victories. What does that mean for young people going into tech?
Reboot is a publication and community for young technologists, primarily students and new graduates. Its aspiration is to reclaim techno-optimism from the techno-utopians—a counterpoint to the endless parade of “tech for good” initiatives, where solving systemic crises is only ever an app away. We sat down with some members of Reboot—Jasmine Sun, Jasmine Wang, and Alan Luo—to help understand how the next generation of tech workers sees their work and their future. We talked about lying to VCs, learning to “pass” in Silicon Valley, and how to find a sense of agency in a world of crisis.
Let’s start by having each of you introduce yourself.
Jasmine Sun (JS): I’m currently a tech worker at a startup. I grew up around the tech industry on the Eastside of Seattle, but I was always more interested in the humanities and social sciences. Then I went to Stanford and got immersed in Silicon Valley. I was shocked by the amount of money and power and prestige flowing through the Valley and ending up in the hands of very young people—even some of my freshman-year classmates. Often, the young people didn’t know what to do with all that responsibility. But it also felt like an opportunity to me. I had an interest in social justice, and while I was initially interested in going into academia or law, I started to think it would be higher leverage to apply that interest in social justice to the tech world.
Jasmine Wang (JW): I was born and raised in Alberta, Canada. The main industries there are oil and gas and agriculture—no tech. There were no computer science classes offered in my K-12, except for a typing class in elementary school, and a class in junior high where I learned how to use Google Drive, if those count. In university, I started out studying comparative literature and doing nonprofit work. I went to my first hackathon in my first semester and built a website for the nonprofit I had founded. I was really moved by the scale at which people were dreaming in technology, as well as seminal texts I was reading in the digital humanities class I was taking, and it was an easy decision to transfer into computer science the next semester. I had the sense that I needed to move to Silicon Valley to have a real pulse on things, and worked hard to get internships there, and ended up living in the area for about two years all together. It very much felt like I came of age in the Valley—a lot of my worldview and value systems were deeply formed by that experience.
Alan Luo (AL): I started programming at a young age. I was always interested in making video games because I played them growing up. My first exposure to the industry was when I published something that I made on Reddit, and it went a bit viral on Hacker News. It was this program that you could use to generate art. Then someone reached out to me to ask whether I wanted to freelance for them. So that was my first job in high school. What immediately struck me was how much money I was receiving for the work I was doing—there was nothing else like it. So then I went to Columbia, and did one year there before the pandemic hit.
Jasmine (Wang), you said you founded a company. What was that experience like for you? There’s a lot of cultural emphasis in Silicon Valley on the young founder. How did you navigate that?
JW: Founding is an interesting thing. When you are a founder, the mission of the company has to be your personal mission. You are not able to recruit talented people or get venture investors on your side if you can’t convince them that you’re going to put the best ten years of your life into a company. You have to bleed, sweat, and die for this thing to exist. You need to persuade everyone that your startup is deeply aligned with your value system and worldview, or people won’t take a bet on you.
I think it’s deeply unhealthy. I think it has caused a lot of mental health problems that founders are not able to talk about, because it would hurt their prospects at raising another round and hiring people, not to mention keeping bread on the table. That’s the thing: as an employee, you can just show up and do the job, to pay the bills. As a founder, you still have to pay the bills, but you can’t divorce yourself from your work on an ideological level. Even if you’re super burnt out, you can’t check out—you have to keep performing that founder role. This wasn’t the case for me, but I imagine that for younger founders labeled as some sort of wunderkind that this dynamic would be even more damaging—especially if the company fails, as most do.
AL: The way people view you affects how you raise money. That is definitely true.
JW: I remember a conversation I had with a mentor of mine where I told her, “I only want to say things that are true.” To me, words and language are almost the only things that we have; they’re so precious. They’re how we dream and make commitments to each other. And my mentor laughed at me, in all kindness. She said, “Never start a company. You will constantly have to say things that are not true to you, if that is what is required for the company to exist.” There’s also actual danger with saying things that are not true to you—the cognitive dissonance is so painful that you shift your self-concept for saying those words to make sense. It’s the same reason why manipulation tricks, like getting someone to do a favor for you to make them like you, work.
JS: I am uncomfortable with lying in general, even when it isn’t harmful, or if it’s just an exaggeration. I had a couple of advisory conversations recently where I was asked whether I would ever do Reboot full-time as a nonprofit. I told them, “Oh, I feel like I couldn’t get the money to do it.” And they were like, “No, you can get the money, that’s easy. But in order to get the money, you have to say you’re gonna scale Reboot to 20,000 people and 200 schools.” On the subway home, I was just like, do I want those things? Would I enjoy the version of Reboot where I was trying to scale it 100 times?
JW: I want to make a distinction. When I use the word “lying,” I mean saying things that are not true to one’s self. And this doesn’t have to be an outright lie. It can be something that is factually true, but misaligned with who you are.
I remember calling some friends as I was getting ready to raise a round. Their advice was: “Act like Mark Zuckerberg.” Apparently Mark had a reputation of being disrespectful to VCs and telling them he didn’t need their money. That shocked me. And I think it’s because being disrespectful goes against my core values. I’ve never intentionally disrespected someone. And also, I couldn’t imagine telling VCs I didn’t need their money. What a concept. Of course I need their money! What sort of world are you coming from? Like, how can you not need money? And then I was looking at Zuckerberg and realized, oh yeah, his dad gave him a $100,000 loan to help start Facebook. He didn’t need other people’s money—at least not in a food-on-the-table type way.
Second Languages
You all had to learn to present yourself a certain way in order to be maximally appealing to the gatekeepers of the industry, whether it was VCs who might fund your startup or companies that might hire you. But how did you learn to perform these roles? Was it just a process of trial-and-error, or was there a more systematic way that you taught yourself the cultural protocols of the Valley?
JS: When I first got to college I had imposter syndrome, because I met so many people who were child prodigies. They were on magazine covers. I hadn’t done anything. I felt depressed. I also noticed that everyone in Silicon Valley was speaking a language that I didn’t understand. Like literally, I didn’t know what the words meant. So for a year I read a bunch of books that seemed to be the Silicon Valley canon: Zero to One by Peter Thiel, The Hard Thing About Hard Things by Ben Horowitz, Hackers: Heroes of the Computer Revolution by Steven Levy, Radical Candor by Kim Scott. I read whatever I thought other people were reading. Because I didn’t have a network yet—I didn’t have a way to learn directly from other people. But I wanted to know how the Valley thought.
JW: I didn’t know anybody in the Bay Area when I came here. I didn’t even know what books I was supposed to read. So I joined as many different communities as I could. I thought they could give me what I was missing. It can be hard to find that information, because there are so many limits in terms of what is chronicled. Most of the stories about Silicon Valley are written by very particular people who live very particular sorts of lives. There are so many stories that are not chronicled, like those of women and people of color. So you have to go find those stories in different contexts—more high-trust contexts, not public forums but Signal and phone calls.
Ultimately, I felt like I had to learn the right language to pass in the Valley. A lot of what you need to know is what you’re not supposed to talk about. In tech, you don’t really talk about money or power. Everyone’s default is, “I have no idea how much anyone earns.” Everyone dresses approximately the same and lives in approximately the same way. But some people wield much more power—orders of magnitude more.
AL: A lot of queer culture is oriented around being very “out.” But something’s at stake, so you might want to twist your words to get what’s best for the company. I don’t know if I care about participating in mainstream queer culture anymore, because it’s just not made for Asians. I want to be representing me, I don’t want to be queer for the sake of being queer. So if there is a version of like, Sino-queerness, which draws from traditions of Taoism and the existence of two spirits within the body or whatever, that’s the version I want to be creating.
The Bamboo Ceiling
JW: Technologists are told that they only need technical competence, which is incidentally convenient for the bureaucratic governing class. This is perpetuated by the model minority myth, which says you only need to be good at STEM to have a good life, and that to be a good citizen you should keep your mouth closed. But the reality is that those skills only go so far. People talk more about the “bamboo ceiling,” but it’s always been there: Chinese-Americans might have technical competence, but they often don’t have the social capital needed to rise into C-level positions. Those are positions that require a lot of networking, a lot of buy-in, and often build off of generational privilege. Seeing which founders get funded and what they look like—that’s all about social capital, not engineering prowess. But then you look at those founders’ engineering teams and it’s a very different demographic makeup.
JS: My mom told me many times, “If you’re good at math, you’ll be good at everything.” I’m not good at math. And I had a lot of issues around my failure to be good at math growing up. It made me feel like I was failing in general, because my parents, and all their friends, and all their friends’ kids, were good at math.
But yeah, the reason Asian kids get ushered into STEM careers, like being a doctor or being an engineer, is because you usually don’t need social or cultural capital to succeed in those roles. There’s a certain set of things you need to learn to join those professions, and they’re open knowledge. You go on LeetCode [an online programming education platform] or you study for the MCAT. There’s not too many hidden codes about how to get those sorts of jobs.
Whereas being a VC is 100 percent hidden codes. There’s no playbook on how to get into VC. And if you don’t speak English well, or even if you just don’t know the social landscape, you can’t break in. I remember when I learned about cold emailing my freshman year of college. It blew my mind. I had no idea you could just email somebody and they would respond, because I couldn’t understand why they would talk to me. Now I love cold emailing—it’s the best thing invented. But you need that confidence.
The reason that I’m so interested in sociology is because I have been so baffled by the non-explicit networks and the other social components that go into creating technology products. Silicon Valley claims that it’s all about technology, that the product sells itself. But Silicon Valley is where I learned how much networking mattered, and how much it mattered to speak a language—which is very incongruent with what the Valley tells itself.
JW: My mother spent her entire life programming and she remained just an IC [individual contributor], and was never promoted. Once, she was fired out of the blue. It was simple to swap in another engineer for her. It seems much harder to swap out a general partner at a venture firm. That person’s power is rooted in relationships that are harder to build—less fungible. You can build technical skills by yourself, but social capital is predicated on so many other things. Who do you know? Where did you grow up? Do people like the sort of person that you are? Do you ‘pass’ to them as someone who’s in their social class? Are you able to afford the hobbies that give you access to the right people? In the Valley, people go to Equinox, Barry’s, and Burning Man—there’s all these stories about founders and VCs meeting at Burning Man. It costs thousands of dollars to sustain that lifestyle. So all these invisible things that accrue social capital take a lot of real capital and time to build. If you’re building technical skills, you can literally sit on your computer and do it alone in your room, and then go somewhere and get employed. But that also makes it less robust, in some sense.
Coming of Age
JW: Broadly, what we’re talking about here is coming of age. Some of the questions we’re struggling with are the same ones that young people have been struggling with forever. “What are my values?” “How do I prioritize between those values in order to ensure my personal stability and the stability of the work that I feel like I need to do?” “What conflicts do I attend to?” “How do I take care of and steward the lineages that are important to me?”
But we’re also asking those questions in a particular historical moment. So what’s changed for our generation? And how does technology fit in? What is unique about our time?
AL: I’ve been talking to my parents a lot. And they said, “Yeah, we knew this was going to happen, because this is what happened to our generation, when we were growing up in the Cultural Revolution. Every single one of us went through the exact same thing that you’re going through now. We started off being idealistic, and eventually realized somebody somewhere else was profiting from us.”
Because I spent so much time on social media, I just didn’t talk to my parents when I was younger. I wish I had, because then I would’ve heard those stories earlier, and maybe could’ve avoided certain situations. Social media put my head elsewhere. It uprooted me from my family and my history and placed me into a strange soup of fellow Gen Z’ers. My values have been shaped by that soup, not my parents or my lineage.
JS: I’ve been moving in the opposite direction when it comes to idealism. I was not idealistic for the vast majority of my life. I am a skeptic, and critic, by default. I think it has to do with coming of age while reading and being influenced by a left-wing academic world that has a lot of pessimism and negativity. In that world, the assumption is that anything you build is going to get co-opted. Everything fails, so there’s no future possible unless we burn it all down. And we probably can’t burn it all down.
I feel grateful to that world, because it gave me the capacity to understand power and systems. At the same time, it deprived me of a sense of personal agency because it doesn’t believe that things are worth trying. I see the same hopelessness in many of my friends and peers. They feel disillusioned by Big Tech—or really, by capitalism. They’re not very happy on a day-to-day basis. They’re depressed about climate change but feel they can’t do anything about it. Or they hate their job and think the company they work for is terrible for the world. But they also need to pay rent and have no idea what else to do. I also have friends who go into academia. And when I ask them why they’re doing it, they say, “Harm mitigation.” I’ve heard this from multiple friends. They’re like, “Every job is so flawed—it’s either the private sector or the nonprofit industrial complex. So I’m just going to go into academia, because I know that the university is not perfect, either. But it feels like it does the least harm.”
It’s a very pessimistic point of view. I want to reclaim a sense of agency. I think we need more idealism.