California Dreamin': Entourage, Silicon Valley, and the Importance of Delusion

California Dreamin': Entourage, Silicon Valley, and the Importance of Delusion

It can be difficult to explain what you want most in the world. To a mountain climber, for instance, it would be difficult to explain to most people why you’d be willing to risk your life on one of the most grueling climbs imaginable, in one of the most remote places on the planet, just for the thrill of standing on a big rock. You can’t explain what makes that possible without explaining a sort of passion or ambition, a force within yourself strong enough to override common sense. Without an inner force like this, no one would summit difficult mountains like Everest or K2; it’s too difficult and too likely to kill you. You have to have a passionate ambition to climb; you also have to have a certain degree of masochism, or at least pain tolerance for the challenges you'll face.

Not too long ago, we were based in San Francisco, center of Silicon Valley, and we noticed a lot of people with the same mentality. Everywhere people seemed very smart, very capable—and very stressed. In some ways it’s easy to appreciate California living: good food, steady climate, beautiful scenery, and plenty to do. But, of course, we also saw the exorbitant rent prices, the high turnover and failure of startups, and everywhere signs cultural, political, and economic that the tech boom had changed the city permanently. There was wealth and great opportunity in San Francisco, but also punishment for failing to sustain them. Still, despite the clouds that hung over parts of it, San Francisco was motivating in part because of that ambition which had a fire lit under it—people willing to climb high and fast even though the fall might grievously injure them.

As Mike Birbiglia points out in Sleepwalk with Me, there’s an element of delusion that’s crucial to many forms of success. By Birbiglia’s own description, he’d never have become a comedian if he hadn’t convinced himself that his first show had gone well enough that he should continue performing. By any measure of common sense, someone who promises 30 minutes of material for his first set, pukes immediately before walking on stage, and then bombs 4 minutes of material has not done well at all—but he convinced himself he did well anyway. He kept coming back and getting better, and now he’s quite successful. Delusion was his friend.

Delusion seems to have been Elon Musk’s friend as well—since, by any measure of common sense, a car startup is a terrible idea. Not only is a car a particularly difficult good to manufacture, but it’s one of the oldest and most entrenched sectors of manufacturing in the world. More to the point, no one wanted Tesla’s cars when they were first starting; Musk had convinced himself that a $100,000 electric car was something that the world wanted. It took a lot of big gambles paying off, but pay off they did, and guess what? Whether he'd been ahead of his time, or whether he himself was responsible for it, his delusion became reality. Lots of people want Tesla’s cars now; over 100,000 people signed up for a Tesla Model 3 in the days after preorders were made available on their website.

It’s hard to call people like Elon Musk or Steve Jobs "deluded" when they wound up getting so much right. We don’t focus on their delusion, important though it is, because it’s overshadowed by the brilliance and struggle of their efforts, by the size of the chances they took. So, to zero in on the delusion part a bit more clearly, we turn to the sort of genre that accentuates delusions: comedy.


Two of our favorite shows are the HBO comedies Entourage, which ran from 2004 to 2011, and Silicon Valley, whose third season debuts this month. Both are, in broad strokes, sophisticated sitcoms, and they’re both shows about people wanting to strike it rich in sunny California, where everything is beautiful but maddeningly expensive.

Let’s be clear: in neither show do the characters have a great grip on reality. In Entourage, for example, our main character Vince is out of work for months and is rapidly accruing debt on his credit cards, six figures at a time, with nothing to pay them back. His accountant calls him screaming; his entourage member Eric, then a voice of reason, cautions him to slow his spending. But other entourage members Turtle and Drama—and Vince himself—remain convinced that everything is fine, that nothing will go wrong, and that none of their expensive habits (such as $2,500 per month on vitamin supplements) need to change. Vince explains the Maserati he buys Eric on credit as a “matter of appearances” for himself and his friends; when invited, he bets $100,000 he doesn’t have on a soccer game. Any sensible person watching Vince spend money instinctively begins biting their nails (video below is NSFW due to language).

In Silicon Valley, our main character Richard isn’t delusional so much as he is blind; he’s a talented but reclusive programmer who doesn’t understand the power of what he’s created. Then, once thrust with the responsibility of making something from it on his own, he mostly fumbles. His cohorts Gilfoyle, Dinesh, and Jared are varying brands of exaggeration, shade, and naivete. The truly delusional one in the bunch is Erlich Bachman, with whom Richard is obliged to share equity and, given his rare extroversion and confidence, the responsibility of representing their company publicly. To give you an idea of a Bachman “good idea”—when he doesn’t like the name of the company, he takes a bag of psychedelic mushrooms into the desert to meditate on a name that sounds right, and this is the result (NSFW):

And yet, in their worlds, all does not go as poorly as it should.

In Vince’s case—spoiler alert, but we doubt this will surprise you—his reckless spending creates no problems for him. He lands a new role and a big check right in time. Life continues more or less as he dictates, spending and otherwise. Vince’s hilarious, unhinged rageaholic agent Ari Gold deserves a lot of the credit for Vince’s success, as viewers see, but Vince gets to preserve his image and wealth more or less as he chooses. For all of his delusion, Vince is rarely wrong in the end.

In Silicon Valley, Bachman is delusional because of his inflated sense of ability and importance—but he also seems to understand that his delusions are important to creating the right results for the team. He pushes the naturally shy Richard to be louder and more assertive. Where other companies mumble a boring presentation through a handheld mic, he prepares bombastic, Steve-Jobs-with-dance-lights presentations; over the top, perhaps, but borne of the right idea, namely that presentation always matters, especially for boring ideas. Even the ill-advised mushroom trip was an attempt to find genuine inspiration (which often starts as nonsense) in place of the uninspired status quo. Even when Bachman’s contributions to the team’s success are dubious, it’s hard to picture the team without a force like his.

Of course, we don’t intend to make real claims about the world based on what we see on TV shows. It would be horrifying, for instance, to follow any example of Vincent Chase’s when it comes to money; it would be stupid to hire someone loud and self-absorbed (and on shrooms) just because your team is too reserved. We do, however, enjoy the fantasies these shows provide, and we do enjoy that they make us more aware of our own delusions.

In our case: it seems silly, by any measure of common sense, to believe that you can change the world by selling notebooks. Yet we do believe we can change the world, especially if our notebooks are just the beginning of something bigger. We start with what we know, like what people say about our books, and then with what we love and want to grow about the books, and eventually we allow ourselves the delusion that they might someday contain some of the most important ideas of our time. Maybe it is a delusion, but if it is to come true, we have to have ambition to override common sense. We have to truly believe it first.

In shows like Entourage and Silicon Valley, shows that are not meant to depict reality, you’re not likely to find new revelations about the world, so much as reminders of what you already know about it. They’re colorful, exaggerated, and sometimes downright ridiculous, but somewhere in there they include a few real reminders about ambition and success:

First—Confidence is key. Fake it ’til you make it. When in doubt, look like you know what you’re talking about, and soon enough you will.

Second—Great expectations do have the potential to become real. Sometimes, you have to accept a situation where the odds are stacked against you to have a chance at winning the biggest prizes. Delusion is convincing yourself success is more likely than it is—which, to be real, is psychically necessary sometimes.

Third—Remember what you actually want. If landed stars like Vince seem less ambitious, it’s because they've already made it. You see how Vince gets to enjoy it—by numerous admissions he just wanted the good life with his friends, and he has that—but you also see how easy it is for Vince's life to lose direction. Things only stay good for successful people when they remain driven.

California, it seems, is perpetually a land of dreamers. Let’s not forget, after all, that the land of both Hollywood and Silicon Valley was once the original place for Americans to strike gold. The dream continues today, and if we’re being honest, it isn’t always realized—but that doesn’t mean we shouldn’t allow ourselves to dream anyway. It’s how great things get made.

Thanks for reading Ampersand, the Code&Quill blog. (Last week, we wrote about techniques for improving how you speak and present, so click here to take a look if you missed it.) If you’d like highlights from the blog, plus brand-new info about upcoming products and promotions, feel free to join our email newsletter here.


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