This blog has moved

I’ve been invited to join the Svbtle blog network, and I’m moving my blog to that platform. I’ve christened the new blog Uncharted Territory.

My first post is already up, and I hope you’ll follow me there in your feed reader or by email.

Making “doing it right” easy

If you’re like most people, you don’t think too much about how you type quotes, dashes, or ellipses. As people have done since the days when most text was in ASCII—or before that, the days of typewriters—you type the same character for left and right quotes, three dots for an ellipsis, and (bless your heart) two little dashes--like this--when you want to insert a pause. These substitutions were a good form of economy back when keyboards and character sets were limited, but today, almost all text is in UTF-8 and supports ideal quotes, dashes, and other marks.

If you’re typing in a word processing application, it might automatically improve your punctuation, turning double-hyphens into em-dashes, straight quotes into “smart” ones, and the triple-period into a proper ellipsis. But most web-based text editors haven’t caught up, and as more typing moves to the web, we are more often left with the old approximations.

If you want to up your punctuation game, the secret is to learn the keyboard shortcuts for the ideal marks. On a Mac:

  • To type proper quotes, “like this,” use option-[ for a left double quote and shift-option-[ for a right double quote.
  • For single quotes, ‘like this,’ use option-] and shift-option-]. You can also use shift-option-] for an apostrophe.
  • For dashes, only use the short dash on your keyboard for a hyphen. For ranges, such as 3–5 or Nov 1–Dec 31, use an en-dash, which you can get by typing option-hyphen. For a long dash in a sentence that indicates a pause—like this—use an em-dash by typing shift-option-hyphen. (Alternatively, use an en-dash surrounded by spaces – like this. Wikipedia has a decent guide to dashes.)
  • For an ellipsis … like this … simply type option-;. (Make sure you’re using a proportional font, though.)

This won’t slow you down once you automatize it. I learned how to do proper dashes a long time ago, and now it’s second nature; I don’t even think about it. The keys are in muscle-memory; I had to look at my fingers in order to consciously remember the proper combinations. I’m training myself on the others now.

Why bother? For my part, I’m doing it to sharpen my typography sensibilities, as part of heightening my overall design sense.

There’s a deeper point here: You need to practice doing things right so that when you’re doing actual work, doing them right is easy. If you haven’t practiced, then doing things right will be prohibitively difficult. It’s not worth slowing down just to get one punctuation mark perfect. To make it worthwhile, you need to make it fast. That’s why you need to learn the keyboard shortcuts rather than inserting the marks through a special UI, and why you need to practice them until they’re automatized.

The same goes for other aspects of design. The tech community has learned to value design much more in the last several years, but most engineers still turn out ugly apps when left to their own devices. Why? Because when you haven’t learned how to make a proper gradient button in Photoshop, how to use a CSS grid system, or how to create a rational site navigation structure, doing so slows you down too much.

The same goes for other technical skills. As a software engineer, if you already know how to write efficient SQL queries, use a JavaScript framework for client-side MVC, or write a good automated test suite—you’ll do it. If you haven’t learned those things when you start a new project, you won’t have time to learn them, and you’ll compromise. (Sometimes that’s even the right choice.)

If you want to do something right, practice the skill until doing it right is easy.

Thanks to Carolina de Bartolo for giving the talk on typography that got me thinking about this, and to Designers + Geeks for hosting her recently.

To the circling vultures

Dear recruiters,

No need to all send me a LinkedIn message at once today. You have no special opportunity to get my attention just because my company had a bad quarter and our stock price dropped. I make commitments for the long term, and am not swayed by the vagaries of the public markets.

Best regards,

Grit and determination

In her talk at YC Startup School, Jessica Livingston said in essence that determination is a startup’s greatest virtue. She broke determination into two parts: resilience and drive. “Resilience keeps you from being pushed backwards. Drive moves you forwards.”

Reading this, I was struck by the similarity to the analysis of “grit” by Dr. Angela Duckworth, which she defines as “perseverance and passion for long-term goals”. Like Livingston, Duckworth says that you need both parts: perseverance in the face of setbacks, and the passion to focus intently on one big goal over the long term.

If this intrigues you, watch this TED talk by Duckworth introducing the concept:

For more on what it takes to do great work, see this roundup of the research by Eric Barker.

Ayn Rand and Silicon Valley

Travis Kalanick’s recent talks at YC Startup School and elsewhere, in which he often decries the interference of protectionist regulations that block competition in the taxi business, have some people talking about how Kalanick has been influenced by Ayn Rand and Objectivism.

Rand resonates, to a greater or lesser degree, for many in the tech startup world. Fred Wilson recommends Atlas Shrugged, and Brad Feld is a fan as well. Several less prominent investors and entrepreneurs, such as myself, are Objectivists.

The reason is that Objectivism and the Silicon Valley ethos have a lot in common.

Maker mentality

The Valley’s ideal is a productive maker who is driven by a creative vision, something he passionately believes in and wants to make real. This is exactly the essence of some of Rand’s best-known heroes, such as architect Howard Roark from The Fountainhead:

Austin Heller: “What in hell are you really made of, Howard? After all, it’s only a building. It’s not the combination of holy sacrament, Indian torture and sexual ecstasy that you seem to make of it.”

Howard Roark: “Isn’t it?”

The maker works long and hard over many years, triumphing over obstacles, setbacks, and naysayers—like Hank Rearden, the industrialist from Atlas Shrugged, did to create a new metal. Rand describes:

the nights spent at scorching ovens in the research laboratory of the mills—

—the nights spent in the workshop of his home, over sheets of paper which he filled with formulas, then tore up in angry failure—

—the days when the young scientists of the small staff he had chosen to assist him waited for instructions like soldiers ready for a hopeless battle, having exhausted their ingenuity, still willing, but silent, with the unspoken sentence hanging in the air: “Mr. Rearden, it can’t be done—”

—the meals, interrupted and abandoned at the sudden flash of a new thought, a thought to be pursued at once, to be tried, to be tested, to be worked on for months, and to be discarded as another failure—

—the moments snatched from conferences, from contracts, from the duties of running the best steel mills in the country, snatched almost guiltily, as for a secret love—

—the one thought held immovably across a span of ten years, under everything he did and everything he saw, the thought held in his mind when he looked at the buildings of a city, at the track of a railroad, at the light in the windows of a distant farmhouse, at the knife in the hands of a beautiful woman cutting a piece of fruit at a banquet, the thought of a metal alloy that would do more than steel had ever done, a metal that would be to steel what steel had been to iron—

—the acts of self-racking when he discarded a hope or a sample, not permitting himself to know that he was tired, not giving himself time to feel, driving himself through the wringing torture of: “not good enough… still not good enough…” and going on with no motor save the conviction that it could be done—

—then the day when it was done and its result was called Rearden Metal.

Going against the consensus

The virtue of independence—thinking for yourself—is the theme of The Fountainhead and a cardinal virtue of the Objectivist ethics. It’s also a part of the maker mentality: innovation comes from following one’s own judgment, not the herd. Fred Wilson says social proof is dangerous, while Brad Feld exhorts investors to make their own decisions.

In contrast to the makers, mere copiers like the Samwer brothers are looked down upon. In the Valley, you get more respect if you try an original idea and fail than if you copy an idea and succeed.

Rand’s basic conception of independence is having one’s primary orientation to realityto the facts; not to other people and their ideas. To succeed in entrepreneurship and especially in investing, though, you need to go farther. You need to be not only be right, but non-consensus right. I first heard that idea and that phrase from Mike Maples, but I heard a variant of it from Peter Thiel in his recent Stanford lectures on entrepreneurship, and from Reid Hoffman at a Pando Monthly event.

Creating more value than you capture

This one may come as a surprise to those who only know that Rand advocated “selfishness”. But Rand’s basic guideline for human relationships was what she called the trader principle: deal with others by trading value for value, by mutual consent to mutual advantage, never seeking nor granting the unearned, never sacrificing yourself to others nor others to yourself. In other words, seek only win-win relationships.

The maxim to “create more value than you capture” is a corollary. If you try to capture more than you create, you’re seeking the unearned. When you create more than you capture, you’re making sure that those you trade with are getting something out of the deal, too.

Playing the long game

Creating more value than you capture is part of a larger theme in the Valley: playing the long game.

To play the long game means to remember that the relationships and reputation you build need to last you a lifetime. Thus, we look down on those who screw over co-founders, employees, or investors; we admire those who honestly and bluntly admit mistakes. Reid Hoffman extols the value of “alliances built on trust and integrity”, saying that in the long run they are the most valuable.

The long-term mentality is also a key part of Objectivism. Rand’s ethics is based on the idea that to thrive and flourish, one must think and act long-range. The grubbing, short-term mentality is ultimately self-destructive. This is why a philosophy that advocates self-interest also demands ruthless honesty, integrity, and justice. Moral principles, Rand held, were the only way to grasp the long-range consequences of one’s actions and to make the right choices in the scope of one’s entire life.

Unlimited ambition

What I love most about Silicon Valley is the intense ambition that is a part of the culture—the drive to do great things, to achieve the extraordinary, to change the world. Our heroes are not martyrs; they are successful, happy, and often rich.

As Rand wrote in Atlas Shrugged, in a passage that could inspire any entrepreneur in his darkest days:

Do not lose your knowledge that man’s proper estate is an upright posture, an intransigent mind and a step that travels unlimited roads. Do not let your fire go out, spark by irreplaceable spark, in the hopeless swamps of the approximate, the not-quite, the not-yet, the not-at-all. Do not let the hero in your soul perish, in lonely frustration for the life you deserved, but have never been able to reach. Check your road and the nature of your battle. The world you desired can be won, it exists, it is real, it is possible, it’s yours.

That deep, abiding optimism, that sense of the grandeur of life and the world, is part of what drew me to Objectivism and what resonates with me so deeply. I think it’s what resonates with others in the startup community, too.

If you like this post, vote it up on Hacker News.

Map vs. compass at Facebook

From an article by Andrew Bosworth from a few years ago (emphasis added):

The path Facebook took to connecting everyone in the world was not the shortest and that has made all the difference… if we had tried to jump straight to the end state, we would have never gotten it right.

In technology we are constantly looking to the future and trying to see things the way they could be. Once we have a vision we want to work towards we tend to choose the shortest path to get to that place. On projects of sufficiently narrow scope this is clearly the right thing to do. When it comes to strategy, however, our success has come from not concerning ourselves with the entire path to the goal but rather focusing primarily on the next step in that direction.

To do something great you need a compass, not a map.

Managers who make your job easier

When a new hire joins my team, in our first one-on-one, I give them a spiel that goes something like this:

There are two kinds of managers: managers who make your job easier, and managers who make your job harder.

I strive to be the first kind of manager. That means you should let me know whenever there’s something I can do to make your job easier, or to make you more productive. It also means you should let me know whenever I slip into becoming the second kind of manager—which I do occasionally (usually when I’m bugging you for status too often).

I’m not necessarily going to be checking up on you all the time. If I’m not checking up on you, it doesn’t mean that I don’t care what you’re doing, or that your current task isn’t important. It means that I trust you to be productive. It’s your responsibility to be productive and to always be working on whatever the team’s top priority is at the moment.

If you don’t know what the team’s priorities are, you should come talk to me right away. You should also talk to me right away if you think the priorities are stupid. And you should talk to me if you can’t make progress on what’s most important.

Sometimes I have to wrangle all the details of a project to get it out the door. When I have to do that, I do. But it’s a better kind of success when the team gets a project done without me coordinating it, because we got aligned on goals and priorities first.

Everyone goes through The Struggle

Ben Horowitz’s latest blog post, on The Struggle, is a gem. It’s a healthier, stronger take than some things I’ve read recently that say “being a CEO is awful”, and a more mature, realistic take than “being a CEO is tons of fun”.

The most important point is that everyone goes through The Struggle—even those who win. You don’t win by somehow avoiding the struggle. You win by getting through it.

Thus, my favorite part was this: “If you want to be great, this is the challenge. If you don’t want to be great, then you never should have started a company.”

What I love most about the Valley is that it’s full of people who want to be great. People who know that the average startup fails and are going to do it anyway.

Some of them do it because they think it will be easy for them. They learn. When they learn, some of them quit. After all, when you’re going through The Struggle, it is perfectly reasonable to quit.

Maybe this is why investors like to back serial entrepreneurs, even one whose first company was a failure. They know how hard it’s going to be, and they’re doing it anyway. Again. They aren’t doing it out of a delusion that it will be easy. They’re doing it because they want the goal so much that they’re willing to go through the struggle again. That’s probably the best indicator that they might get through it.

How to (and how not to) cold-email a candidate

Like most engineers in the Bay Area, I get a lot of recruiting emails. I got two today.

One was pretty bad. Multiple spelling and grammar mistakes, unsubstantiated bragging, virtually no description of the role, no description of the company culture:

I’m super excited to be recruiting for the super hot startup, [company] ( [] )!!!

[Company] empowers people to [value proposition]. [Company] offers [product description] for iPhone 3GS and iPhone 4, and Android devices including [list of Android devices], and works with [etc].

[Company] recently recieved $XX Million in series C funding and are looking for iOS pro’s such as yourself… we need YOU!

Interested in the opportunity? Let’s set up a chat- let me know the best contact number and time to reach out =)

I didn’t even bother to respond to this: it’s a form letter, with nothing to indicate that the recruiter even looked at my profile. That’s my bar. If a recruiter personalizes the message at all, I will respond. Easily half the contacts I get fail to meet this bar.

Usually I dash off a one-liner saying that I’m not available. To get more than that, you have to acknowledge at least some of the key facts of my situation: I’m a former co-founder and I recently sold my company, so I’m very unlikely to move, and when I do, it’s likely to be to a co-founder role again.

The other recruiting email I got today gets it right:

My name is [name] and I work at [company]. I found your Twitter profile when browsing through some groups of iOS developers, which led me to your blog, and then your LinkedIn profile. Both [other person] (our current iOS “team”) and I are quite excited to get the chance to talk to you given your impressive history, from CMU to co-founding Kima Labs. Admittedly, we also found ourselves shaking our heads in agreement as we read through your recent blog posts.

A little bit about us. We’re a small start-up based in San Francisco, and combined our team has previously shipped products to over XX people. We’re using this consumer product expertise to improve [industry] by creating beautiful tools that deliver [value prop]. We’ve already launched an app called [app name], and there’s lots more to come.

We’re looking for an amazing iOS engineer to help us create next-generation [industry] products that drive meaningful [industry] change. Given that you recently joined Groupon, we know that the chances of you making a move are slim. But if you would like to learn more or know of other folks that might be interested in us, please don’t hesitate to reach out.

Highly personalized, fully acknowledges my situation, and gives me plenty of reasons to be interested in the company. This is how to cold-email a dev.

After thanking them for a great email, I said that I’m fully committed to Groupon right now and I’m not considering other opportunities. But if there are any iOS devs out there who want to work for a startup, drop me a line and I’ll forward you the details. (Of course, I will also pitch you on Groupon; I’m hiring for my team!)

“If you’re offered a seat on a rocket ship, don’t ask what seat”

Sheryl Sandberg’s speech to the graduating class of HBS is worth a read. My favorite part was her relating a conversation in 2001 with Eric Schmidt about an offer she had to work at Google:

So I sat down with Eric Schmidt, who had just become the CEO, and I showed him the spreadsheet and I said, this job meets none of my criteria. He put his hand on my spreadsheet and he looked at me and said, Don’t be an idiot. Excellent career advice. And then he said, Get on a rocket ship. When companies are growing quickly and they are having a lot of impact, careers take care of themselves. And when companies aren’t growing quickly or their missions don’t matter as much, that’s when stagnation and politics come in. If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.

In a way Sheryl and Eric are echoing the career advice of Marc Andreessen, who said:

Never worry about being a small fish in a big pond. Being a big fish in a small pond sucks—you will hit the ceiling on what you can achieve quickly, and nobody will care. Optimize at all times for being in the most dynamic and exciting pond you can find. That is where the great opportunities can be found.

Andreessen also recommends that “the best place to get experience when you’re starting out is in younger, high-growth companies”, because:

You’ll get to do lots of stuff. There will be so much stuff to do in the company that you’ll be able to do as much of it as you can possibly handle. Which means you’ll gain skills and experience very quickly.

You’ll probably get promoted quickly. Fast-growing companies are characterized by a chronic lack of people who can step up to all the important new leadership jobs that are being created all the time. If you are aggressive and performing well, promotions will come quickly and easily.

For this and more great career advice, check out The Pmarca Guide to Career Planning.