"A Lot Of Us Are Really Embarrassed About This Money:" Interview with a Tech Employee Who Made It Big (2019)

What it's like to make so much money you never have to work again

This was originally published on the website for my magazine, The New Modality, in 2019.

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A few years ago, a European organization contacted me. They were fascinated by Silicon Valley, and they hired me to get an interview with “a formerly ordinary person” who had “made it big in startups” — who never had to work again.

It took me some effort to find a person who fit that description and who would talk about it. I had friends who I knew had made a fortune in Startupland, but most of them told me they didn’t want to go on the record, even anonymously. I finally found the person who spoke to me for this interview, and I appreciate their willingness to share their perspective. It’s interesting to get a less filtered take on how it feels to make an unexpected fortune at a tech company, and then figure out a meaningful life afterwards. Plus, the interview doubles as a reflection on dynamics of the broader tech industry.

This interview has never been publicly published as far as I know¹, but I’ve often thought of it in the intervening years, as millionaires keep getting minted in the tech industry (and often have an impact on the culture around them afterwards). I’m excited to finally share it.

LYDIA LAURENSON: How did you end up at Twitter?

ANONYMOUS: I was one of those misfits who school didn’t work for. I was terrible at hitting deadlines. I dropped out of film school and I had literally no idea what I was gonna do with my life. I was applying to work at Wal-Mart.

But I’ve had access to the ideas around coding from an early age, because my dad was a programmer and was always bringing home Commodores [early computer models from the 1980s]. And through my college network, I was lucky enough to meet some inspiring open-source hackers. One of them got me up to speed on modern programming, and he had this amazing life, flying around the world to speak at Linux conferences at age 17. So I had this idea of programming as my shot at financial independence.

For five years, I worked different gigs as a contract software developer in New York. I would always take on projects that were more difficult than I thought I could do, so I learned as fast as possible. And I was hearing all these stories from Silicon Valley — the standard startup dream, that these immature untrained white dudes would have a random idea and then it would suddenly blow up. So as soon as I had the chance to move to San Francisco, I went.

My first startup job was one of those utopian Silicon Valley things. I had a passion for game design, and in my first startup, we thought we were building a future learning platform, a game framework where anybody could teach anybody. It was cool, and I still have a soft spot for that utopian Silicon Valley thinking, but the startup fell apart, as most of them do.

At the time I had some friends who were working for another startup, Twitter. And I loved Twitter as a product. It was still new then, and I must have personally convinced 20 people to sign up for the service. I thought it was such a great product. So one of my friends at Twitter got me hired when my first startup fell through, and that’s how I ended up being one of the early employees at Twitter.

In hindsight, I had a lot of hustle, and I worked hard. But I also know that a lot of it was luck and privilege that positioned me so I had that kind of shot.

LYDIA: What was it like to work at Twitter during those days?

ANONYMOUS: It was crazy. It’s always crazy to work at a startup that’s just getting big, and Twitter was no exception. During my first project, I remember another engineer saying that if the project didn’t work, it was an existential threat to Twitter — that Twitter would stop functioning if we didn’t succeed at our project. And I was like: Oh my God, I just got here. But it was fun too.

I joined during the Arab Spring, when Twitter played a key role in the uprisings. And we all really believed in the service. Within Twitter, we used to call Twitter “the free speech wing of the free speech party.”

I was there for five years, and the company was in flux. I never quite felt like I belonged there. I used to have these recurring nightmares of wandering through a mansion where I didn’t live. I would dream that I was really tired, and that I would try to sleep in different rooms of the mansion, but then the people who actually lived there would come home and I’d get thrown out.

Like many people who work at fast-growing startups, that job was my whole life. I worked late, I worked weekends. I started to feel like the job was sucking out my soul and I had to leave. I was so tired, I didn’t want to do it anymore, and I had always sworn that I would never work a job I hated just for the money. But then Twitter announced that they were going to IPO [i.e., they announced their Initial Public Offering of stock, which had a chance of making early employees rich].

So I got to ride out the last chapter before a major IPO, which was incredibly surreal. We were all so excited. It was the moment we’d all been waiting for. On IPO day, we were hoping for 24 bucks per share, but it actually doubled on the first day and then kept going up!

Most startups structure their contracts so that employees can’t sell for a year after the IPO. That means that employees can’t leave the company until that time has elapsed, at least not if they want the money. So then there’s this bizarre, year-long process where all the early employees at the company are trying desperately to keep the stock price up, because on paper you could be a 7x or 10x or 20x millionaire as long as you keep it up, but that money goes away if the stock price doesn’t stay high.

And everyone says they’re not gonna let this change the company. But because of the financial pressure, some people immediately start catering to Wall Street — looking at short-term metrics, thinking about the next quarterly report, rather than what’s good for the product.

LYDIA: What did you do when you left?

ANONYMOUS: There’s a common Silicon Valley story about stock options, and that story happened to me. When I joined Twitter, I didn’t know how stock options worked. If I had known better when I negotiated my contract, then a few small choices could have made me a very different person today, financially speaking. Not that I’m complaining, because I did fine.

Different people have different numbers at which they’re willing to retire. And part of it depends on your choices. For example, if you’re willing to move to Minneapolis or Jersey City, then your number can be much lower than in San Francisco or New York. To me the number is: What allows you to do whatever you’re truly passionate about?

If you always thought, maybe you want to be an archaeologist, but you did something different because you have student loans? Or what if you always wanted to be a stay-at-home dad? How much money allows you to be an archaeologist or a stay-at-home dad?

For me, the way I think about my number is: I want to do fulfilling work. And I don’t want to have to work as hard as my dad did. I want to be able to spend time with my kids.

So I left Twitter as soon as I could, and I took a very brief 4-week trip to Europe, and then immediately started a new gig in game development, working on a project I’m truly passionate about. Turns out, this is even more stressful than working at Twitter, but more of an opportunity for personal growth.

LYDIA: What kind of choices did your friends from Twitter make?

ANONYMOUS: I’ve seen good and bad examples of people who left without getting jobs. A lot of us gave our whole existence to Twitter while we were there. If that’s your life, then first thing that hits you when you leave is: You don’t need to work.

It’s like looking into the void, because so many other choices you make in your life, from what college to go to to what city you live in, are about your job and how to make your salary go up. Then, suddenly, you realize that it’s almost impossible to make more money than you made at Twitter. The only possible way would be to become a startup founder.

So I think a lot of people became founders afterwards in order to keep themselves on the hedonic treadmill, trying to make more money than they did before. The CEO class has their own way of looking at money, which is a score tally. That is truly a trap. I sometimes wish there was some other way we could find for egomaniacally ambitious people to keep score in a way that wasn’t money, because then they’d share more of it.

Then there’s the people whose number is just really high. There’s a phrase that I’ve always hated, but I heard as soon as I got to Silicon Valley, this phrase: “Fuck you money.” The first person who said it to me explained it like this: “Fuck you money” means you can say “fuck you” to everyone in the world, because there’s no damage that can hurt you anymore. In this way of looking at things, you’re only truly free when you have that much money.

Those people seem to see it as a number that represents complete safety. And it seems to be very binary for some people — and always out of reach. Maybe because if they don’t have something to reach for, then they have to face up to the question of: Why am I here?

So some people started companies after they left Twitter. But a lot of people knew that starting a new company is an incredibly bad idea, because most startups fail. Or they were already burned out from working so hard. So they decided to wait. I know someone who was earlier than me at Twitter, so he must have gotten tens of millions of dollars. He invested in a super intense home video setup and he played a lot of video games. And he traveled. But he got really depressed. He described it as not having a reason to get out of bed in the morning.

I’ve seen that depression move fast, and get bad, for people who had so much money they never had to work again. You hear about suicide. You hear about people who can’t see the point anymore and end it all.

When you make that kind of money, one thing you know about yourself is that you’re now a Rich Person. This is incredibly alienating. You don’t want people to even know it about you because it changes the way they look at you. If you’re dating, it’s gonna be incredibly unbalanced. You find someone you like and they have four roommates when you have two houses. I had one friend from Twitter who went through several doomed relationships at his previous economic level, and finally just started dating a rich girl he met at a philanthropy conference.

So it’s alienating, and it’s worse because no matter how depressed the person gets, they can’t complain about something this great. Like, what would my depressed friend say? He can’t say, “Life is so bad for me, I’m sooooo rich!”

But on the other end of the spectrum, I know people who seem to be doing great without working, at least from the outside. One of my friends from Twitter was so chill, even when she was at the company. You kinda got the sense she didn’t care what her stock was worth, even when she was there, working constantly. And after she left Twitter, she traveled the world, and she has these great pictures of doing yoga on top of mountaintops, stuff like that. And I’m sure she gives away money on top of it, like a lot of us do. She seems happy. She seemed to somehow shift into a graceful peace with her good fortune.

Honestly, most of the time I pretend I’m not wealthy. I haven’t changed my house, I don’t own a car. I haven’t even invested my money. I know that’s dumb. But it’s just, like… this number in my bank account.

A lot of us are really embarrassed about this money. We know the startup game is basically random. No one I know thinks they’re unique because they got this windfall. No one thinks they can brag about it. I never thought this would happen to me. I don’t feel deserving. So most of us aren’t ostentatious.

In Silicon Valley, everyone’s wearing a hoodie, not a designer suit, even if they have millions of dollars. But you also don’t see as many civic works. You don’t see things like what Andrew Carnegie did for America, building the public library system with money he got from the steel industry. And maybe we don’t do those things because people feel embarrassed about it.

I think that this is one reason people in Silicon Valley are so interested in basic income. A lot of us basically already have it. I think a lot of us care about basic income for everyone, because we’ve lived with it ourselves.

And a lot of us want to find a unique thing we can do. We know that the money was luck of the draw, so we end up trying to find a small charity we can start, or in my case to create a very personal game, a game that is a work of art.

LYDIA: Is there anything else you’d like to add?

ANONYMOUS: Thank you for giving me the opportunity to talk about this. I don’t get to talk about it very often.

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1. Update: After the publication of this post, I realized that this statement might benefit from further elucidation. I was commissioned to do this interview around ~2017 or so. The interview was one of three pieces I did for a European media company whose name escapes me. The person who commissioned me told me that they were doing a magazine issue about Silicon Valley. They paid me after I filed the pieces, but then I never heard back from them, though I tried following up.

So, if they published the pieces, then they did so without notifying me. I have always assumed that the pieces were never published. Maybe this is a bad assumption, but I’ve never handed in another writing assignment and not heard anything back at all, so I’m uncertain what else to think. (Typically the editor will at least tell you what happened to the work, whether it was published or not.)

After some time went by with no word from them, I figured that I was free to republish the interview on my own platforms. This also fit within my agreement with the interviewee, who requested anonymity, which I have of course maintained.