How to make a fortune working in Silicon Valley
My first job out of college, I worked at a tech startup that suddenly turned hot, raising a big series C.
I’d cut my teeth on stories about the heroic age of the tech world—people pulling together, working all-nighters along the CEO, coming to him with break-through ideas. And at one of our company socials, I stayed after the event ended and let the CEO talk me into following him to an after-hour bar in SoMa.
This long-haired CEO was one of these intense, shamanic individuals who would walk barefoot even on the dirty streets of SoMa in San Francisco—and I bought completely not just into his particular intensity (his ability to invest you with his complete attention), but also into the feeling that this person must be a genius, must be destined for great things. And at around three o’clock in the morning, I leaned towards him with boozy intensity and said that I’d be willing to do whatever he wanted, no questions asked.
After that, he kept pulling me onto teams, CCing me on emails, saying, “What does N____ think of this?” Within a few weeks, I was working one-on-one with the new Head of Recruiting, helping them liaise with the various unit managers to figure out their needs and make sure our hiring process was sufficiently nimble. My title, my pay, my stock options—none of that changed. But I expected that if I did the work, then the money would follow soon.
And at the CEO’s apartment one night, he asked, “Okay, I just want to know. Why are you here? Be totally honest? What do you expect to get?”
“Well…I don’t know…”
“Come on, cut the bullshit,” he said. “Be real with me. I just want to know, so I can help you.”
“Well…I want to make money,” I said. “I want to…I want to…I want to be at, at least worth a hundred million. I want money.”
“Yeah?” he said. “That’s why you’re here?”
“I mean…yeah. Is…is that wrong?”
“What the fuck?” he said. “I don’t want people who’re just here for the money. That’s not the mission.”
Afterward I sent him a long email, and he never responded. A few weeks later he asked to meet me at the bus stop near our work, and he let me go. Said I wasn’t a good culture fit, and could I please fuck off right now, and oh yeah—since it’d been less than six months, my stock options were forfeit.
The next time a CEO took me under their wing, the same thing happened. It was a woman this time, with long blonde hair and empty green eyes, who talked quite slow. She said, “N____, hey, N____, let’s talk about you.” Her voice was such a low growl. “What do you want?” she said.
“I just want to change the world…”
“Oh,” she said, tucking her lower lip underneath her upper teeth. “Okay. That’s good.”
Again, I was unceremoniously let go.
The third time I spoke to a superior, and they asked for a look deep into my soul, I knew to assess her first. This was a trim, blonde middle-aged woman with tidy bangs and horn-rimmed glasses, brought into a failing company to do a turn-around.
“What’re you looking for in an employee?” I said.
“You’re on edge,” she said. “You’ve been in tech too long! I’m not playing games. Just trying to chat, make conversation. What’s your life outside of work?”
“Mostly I care about my work,” I said. “But I read. I do a little writing.”
“Good!” she said. “Don’t lose that. Don’t lose perspective.”
“I won’t.”
Later on, she asked if I wanted a new role, and I knew the song and dance, I talked a while about the work, and then I asked about a salary raise and title bump. She gave me a nice offer. I asked for stock, since I was still a believer—I figured nobody else wanted any RSUs, so I could them pretty cheap. She advised me, “Take the salary. The stock isn’t gonna be worth much…”
But I knew the rumor that the CEO herself had big performance incentives tied to the stock. She’d negotiated for those strenuously, so I figured I’d align myself with her. If she made money, then I would too. And everyone knew the company had this one valuable asset—shares in a Chinese tech company—and if she could sell these, everyone would make money.
Well, she pulled a shenanigan. She spun out our firm into two separate companies. One was essentially a private equity firm that owned our valuable overseas assets; the other owned our operating business. I and all the other employees were given shares in the second company, but not in the first. When the first was sold, she added another billion to her net worth. My shares were worthless, and I sold them at a loss.
Afterwards, I consulted a lawyer, trying to make sure that I was protected from upside risk. If the company went under, I was okay losing out, but so far I’d been at three successful companies, and I’d lost out each time. I wanted a contract that would be iron-clad.
The lawyer said, “If the company wants you to make money, then you will. If they don’t, you won’t. You have to talk to the founders. Really listen to what they’re saying.”
So for my next company, I looked for a good culture fit. My goal, I knew, was to earn. I wanted a CEO who was a shark, focused on making dough, but was also fiercely loyal. I had by now a good resume and a great record for picking winners, so I could afford to search for honesty.
Finally, I found a man with poor eye contact and a nasal voice, who said, “Of course.”
“Of course what?”
“We’re here to make money. What else is all this for?”
“Great, and what about me?”
“We all eat.”
That was my first failure. The company was a fraud, and we all had to hire lawyers and get deposed.
Reflecting on my experiences with these two women and two men, I thought, Some CEOs are visionaries and hate to employee mercenaries. Some are mercenaries and hate to employee visionaries. Some are mercenaries and hate to employee other mercenaries. Some are mercenaries and want to employee other mercenaries, but they are so mercenary that they can’t help screwing over everybody. Presumably there is out there a visionary who is looking for a good, practical mercenary.
My next time, I looked only for companies doing good, holy work. Not the kind of work that helps people—oh no, that’s absurd—I meant good products that fulfill necessary gaps in the internet architecture. Little fiddly products that only engineers get excited about. I asked every engineer I knew about the best company they knew. And I was directed to one company dedicated to the unheralded process of making web pages load much, much faster. When I interviewed at this company, I told them simply, “I asked my friends about the best company, and you are the best company.”
I went to work for this company, and eventually it raised a large Series C and began to grow. I found myself at a table with the CEO, who resembled my first CEO quite closely, right down to the long hair, and he was expounding on the untapped potential that would be unlocked if websites could run faster.
One of the data scientists said, “Yes, we calculated the cost savings, and if people spend even a fraction of a second less time—”
“Forget about cost-benefit analysis,” I said. “The fact is: our technology is going to underpin the entire internet. That’s the thing. Companies that use our tech will find they can build different kinds of sites—do different things that they’re afraid to do now, because of the performance issues that’d arise. And those new sites will have functionality we can’t even imagine right now. Yeah we can think of some applications, but we don’t know all of them, not by a long-shot. That’s the pitch. That’s the goal.”
These words were very similar to the ones the CEO often said, but I’d put them in much plainer (some might call it ‘quaint’) language. The CEO was duly charmed. Like magic, my performance reviews improved and my promotions got faster. Later, when the company was sold to a big tech giant, most of the company was disappointed. They knew this meant we’d never fully get to develop our technology. It’d get strip-mined for parts and assimilated into this tech giant’s rather shitty in-house products.
The CEO’s deal was structured such that he could take an instant pay-out. But management had golden handcuffs. We’d make millions, but over the course of four years. When the CEO announced he was leaving, I thought, He did it. He fucked me over again. They’ll find a way to fire me, so I don’t earn.
But the new CEO sought me out in his first week, and he asked me about the company. He said the outgoing man had mentioned my name to him, said I was somebody he could work with. I came to realize that in selling this company, the CEO had really been selling people like me. He’d convinced the acquirers that we would stay on, finish the product, maintain its mystique as a world-beating, game-changing product, even as the innovation was slowly sanded away. I’d thought I was working for a visionary, so I’d pretended to be a mix of practical methods and idealistic rhetoric, but instead I’d found a mercenary who’d built up a little cadre of visionaries and sold them to a company who needed some fresh infusion of new blood.
Unfortunately, over my time working at this company, I’d actually come to believe rather strongly in its product—so when California passed legislation voiding the non-compete agreements in our contracts—I forfeited the rest of my contract and left, along with many of this company’s employees, to start a competing concern. We brought our product to market, and for a time our valuation soared. The rise, unfortunately, was so rapid that by the time the company was sold, I hadn’t yet gotten my full allotment of stock, but I did modestly well.
Author’s Note: This tale is a work of fiction. It’s a composite of various things I’ve seen, and stories I’ve heard, during the twenty years I’ve spent on the periphery of the tech industry. Every Thursday, Woman of Letters publishes short tales (told in a variety of styles)—something my usual subscribers are used to—but since it’s been three weeks since the last such post, I figured I’d put in this reminder.
Mark Twain’s travelogues
The above tale was inspired by the silver-fever sections of Mark Twain’s Roughing It, which describe the author’s repeated attempts to strike it rich as a prospector. He goes in search of an easy life, and as a result has to work harder than he could’ve imagined. As he puts it:
If you are of any account, stay at home and make your way by faithful diligence; but if you are “no account,” go away from home, and then you will have to work, whether you want to or not.
Mark Twain, for those who don’t know, was a 19th-century American writer. He was born before the Civil War and grew up in Missouri. His father (a lawyer) died early and Twain left school at age 11, then worked as a printer’s apprentice for some years. Eventually he became a riverboat pilot, but after the Civil War closed the river, Twain was looking for things to do (and he wanted to escape serving in the war), so he went west.
Twain has a class background not-dissimilar from several other 19th-century writers (Dickens and Trollope come to mind) in that he was from an educated family, but he had no money and was forced to work. In prior eras, I imagine people like Twain would’ve simply disappeared from view, but the existence of a mass-market for writing allowed him to become, essentially, a celebrity.
It’s not that Twain is uncultured or without class, but that connection to the mass audience allows him to play up the democratic aspects of his background. His books are filled with a profusion of incidents and a profusion of characters, and he’s well-known for his attention to the vernacular: the details of how people speak. His books were also popular literature. For instance, Innocents Abroad, his story of traveling to Europe and the Holy Land, exists within (and comments upon) the genre of sentimental travel literature. And Roughing It is a response, in part, to dime novels, the stories of Bret Harte, sensational journalism, and other forms of literature that attempted to retail a story about the American West.
That juxtaposition between high and low is what makes Twain interesting. For instance, there’s a part of Roughing It that describes the burial of a prospector. The dead man’s friend thinks, “We really should get a priest to preside over this burial”, so he goes and tries to hunt up a man of God. But the priest and the prospector speak so differently that they quite literally cannot understand each other. For instance, the priest asks if the deceased “had any religious convictions”, and the prospector says:
“I reckon you’ve stumped me again, pard. Could you say it over once more, and say it slow?”
“Well, to simplify it somewhat, was he, or rather had he ever been connected with any organization sequestered from secular concerns and devoted to self-sacrifice in the interests of morality?”
“All down but nine—set ’em up on the other alley, pard.”
“What did I understand you to say?”
“Why, you’re most too many for me, you know. When you get in with your left I hunt grass every time. Every time you draw, you fill; but I don’t seem to have any luck.
Then the conversation continues for a few rounds of them speaking past each other, to hilarious effect.
Looking through my clippings from Roughing It, I see that I clipped roughly 5,000 words of text! I was just so entranced by so many of the details. Every chapter of this book is brimming-over with life. To describe even an iota of what’s in the book seems impossible. Many of the stories in the book aren’t totally true, at least not the way he tells it. For instance, early in the book, he describes meeting a famous outlaw. In real life, Twain did meet him, but he didn’t know the man was an outlaw! Other incidents are complete tall tales or outright jokes, as when he describes a Mormon patriarch’s frustration at a traveling peddler who gives one of his children a tin whistle, and inspires the envy of all the other children from all his other wives:
I knew who gave the whistle to the child, but I could, not make those jealous mothers believe me. They believed I did it, and the result was just what any man of reflection could have foreseen: I had to order a hundred and ten whistles—I think we had a hundred and ten children in the house then, but some of them are off at college now—I had to order a hundred and ten of those shrieking things, and I wish I may never speak another word if we didn’t have to talk on our fingers entirely, from that time forth until the children got tired of the whistles.
Fundamentally, Twain is honest. You can sort of tell from the way something is written whether you’re intended to read it as being true or false. He fabricates incidents and changes details, or he inserts jokes or fables or rumors, but every story is told in the register that is appropriate to its truthfulness. For instance, the above dialogue between the prospector and the priest probably didn’t happen, but I have faith that the attitudes and diction of each one are roughly accurate.
I cannot overstate how much fun I had with these books. My favorite was Roughing It, followed by Innocents Abroad. I enjoyed Life on the Mississippi least, because it seemed to have the fewest details, but I still liked it a lot. They’re all the same—collections of observations and stories, linked by the travelogue format. I felt like Roughing It had the greatest density of insight and humor, but perhaps I feel that way because I read it first.
All three books are somewhat-racist—it’s clear that Twain doesn’t really respect non-white people. He respects visible signs of civilization: cleanliness, industry, and enterprise. Non-white people don’t have these things, so he doesn’t respect them. There are many long meditations about the dirtiness and backwardness of various non-white peoples. The people he respects the most are the Chinese people, and it’s precisely because they seem the most orderly and civilized.
But…unlike most other well-known 19th-century writers, Twain actually bothers to write about other people. He doesn’t do it much, it’s true—Black people especially tend to be absent from these travelogues—but he exists in a well-peopled universe. He is a very honest writer, and he’s going to tell you exactly what he thinks, and he’ll say it the moment he thinks of it. This is funniest, in my opinion, whenever he encounters great works of art or sites he’s meant to hold in reverence. In Innocents Abroad, for instance, he’s somewhat-scathing about the great art of Europe, which he regards as tattered, faded, and pretty shitty-looking. Here’s his comment on The Last Supper:
“The Last Supper” is painted on the dilapidated wall of what was a little chapel attached to the main church in ancient times, I suppose. It is battered and scarred in every direction, and stained and discolored by time, and Napoleon’s horses kicked the legs off most the disciples when they (the horses, not the disciples,) were stabled there more than half a century ago.
Responding to all the gush that’s been heaped upon the beauty of this painting, Mark Twain says:
We can imagine the beauty that was once in an aged face; we can imagine the forest if we see the stumps; but we can not absolutely see these things when they are not there. I am willing to believe that the eye of the practiced artist can rest upon the Last Supper and renew a lustre where only a hint of it is left, supply a tint that has faded away, restore an expression that is gone; patch, and color, and add, to the dull canvas until at last its figures shall stand before him aglow with the life…But I can not work this miracle. Can those other uninspired visitors do it, or do they only happily imagine they do?
It’s so funny, because…it’s true. He’s just saying what he thinks, which is that when he looks at The Last Supper, what he personally sees is not very beautiful, because the picture is old, faded, and beat-up. Similarly, when Twain sees something ugly or uncivilized or rude or annoying, he’s going to say so.
The beauty of Twain is that his honesty is never bitter and rarely particularly hurtful. You can read several thousand pages of his honesty and come away still liking the man and regarding him as a friend.
Further Reading
The audiobooks of these travelogues are voiced by Grover Gardner, who is an excellent narrator that tends to voice a lot of serious, weighty works. He voiced Robert Caro’s Lyndon Johnson autobiographies for instance. His slow, wry, gravelly voice is perfect for Twain.1
Personally, I’ve been slightly disappointed by reprint editions of these works. I couldn’t find Kindle versions of the Penguin Classics edition of Innocents Abroad or Roughing It (for these I just used the free Project Gutenberg versions).2 In general, none of the Twain reprints I’ve read has had a truly good introduction, that gives context on the author’s life and the writing of the work in question. Most of the Penguin Classics Twain books simply describe the plot and tell us the themes and techniques of the work, which seems unnecessary (in my opinion). An introduction shouldn’t just tell us what we’re about to read, it should give us the kind of social, historical, and literary context that will enliven our reading. This generally has been missing from the text versions of Twain that I’ve run across.
Links
Twain has been very well-served by his narrators: Tom Sawyer and Connecticut Yankee in King Arthur’s Court are voiced by Nick Offerman, the comedian, who does an incredible job. And Huckleberry Finn is voiced ably by Elijah Wood. All six of the audiobooks I’ve mentioned in this post are worth listening to.
I just now managed to find a Kindle Penguin Classics version of Roughing It—Amazon’s interface often makes it very difficult to find a proper edition of a public domain text. This edition seems okay, wish I’d had it earlier!
I never thought how much tech start-ups are like prospectors. California is the origin of both ventures. The field is full of mercenaries. Greed abounds. I honestly thought you were writing a story from your life because this is so believable.
Your first segment is really an ingenious tribute to Twain, I dug it!