Don't put your career in stealth mode

When I started my last startup, I kept quiet about my work. I didn’t tell anyone what I was working on, didn’t blog or tweet or promote myself or my apps.

I put my career in stealth mode.

At the time, I had several reasons to stay quiet. I wanted the freedom to explore multiple projects without the pressure of commit­ting fully to one of them. I hated startup­s’ “About Me” pages, full of smiling people bragging about themselves in the third person. And if my startup failed, no one would know—I could quietly move on to the next project.

Five years later, I see this as a huge mistake, maybe the biggest one I’ve made in my career.

Because I have almost no public presence on the Inter­net, you probably have no idea that I’m a programmer (let alone a good one) unless you know me person­ally. Yet I spent most of my time from 2007 through 2011 writing thousands of lines of code, powering apps used by millions of people.

Now, most of that code is dead. Thousands of hours of my life, literal years of work—gone.

My cofounder and I wrote some pretty cool libraries, including:

  • an iPhone table view markup language we called JSTN (JavaScript Table Notation, or Justin, a play on JSON, the JavaScript Object Notation)
  • a simple command language to allow a server to dynam­i­cally control iPhone app flow, such as pushing a new ViewCon­troller, popping up an alert, etc (called SICC, pronounced sick, for Server Invoked Client Commands)
  • many Rails hacks to allow seamless caching, distrib­uted reads and writes, and database sharding

Some of this code lives on in the apps that my cofounder still runs, but nobody knows about it. Like most of my work from the past five years, it’ll probably languish and eventu­ally die. But If we had open-sourced any of these libraries, I’d wager that at least one (and possibly more) of them would still be living today, because they solve real problems.

I recently left my job to start a new startup. One of my goals is to open-source as much work as I can, because I want my code to be used and improved by others. And I’ll write about what I’m doing, so I can share my successes and my failures.

I don’t want to repeat my past mistakes. I’m going to make my work visible, for better or worse. So I’m taking my career out of stealth mode.

There’s some discussion on Hacker News as well.

Writing about loss

Writing about loss is diffi­cult. Few can success­fully describe the empti­ness one feels after the sudden death of a parent, child, friend.

And yet we try. When my mother passed away nearly twelve years ago, I started a web journal. Writing helped me process my thoughts and feelings into something concrete and more understandable.

Joan Didion described loss with quietly powerful language in The Year of Magical Thinking and Blue Nights, her memoirs about the death, in shock­ingly short succes­sion, of her husband and daugh­ter. Despite the painful subject matter, I highly recom­mend reading them (in order), both to people who have experi­enced a sudden loss and to those who haven’t. Didion captures the empti­ness of life without her husband so well—the immediate eleva­tion of once-unimportant miscel­lany to artifacts, the new strange­ness of once-familiar daily routines.

William Maxwell’s So Long, See You Tomorrow is a short, moving work about memory, family, and loss, set in a small town in Indiana. Like The Sense of an Ending, most of the action occurs in the distant past, as an elderly narrator looks back on his life. And, like SenseSo Long can be read in an evening, though I’d recom­mend allowing some time for the words to sit in your mind. Maxwell uses decep­tively simple language throughout the book; it took me some time to realize how carefully he chooses his words, and their cumula­tive effect is powerful.

I’m not sure how long a quote is too long, but I found this passage near the begin­ning of the book exceptional:

My father was all but undone by my mother’s death. In the evening after supper he walked the floor and I walked with him, with my arm around his waist. I was ten years old… Because he didn’t say anything, I didn’t either… His eyes were focused on things not in those rooms, and his face was the color of ashes…

I had to guess what my older brother was think­ing. It was not something he cared to share with me… At night we undressed and got into bed and fell asleep without taking advan­tage of the dark to unburden our hearts to each other. It strikes me as strange now. It didn’t then… What I didn’t say, across the few feet that separated our two beds, was that I could­n’t under­stand how it had happened to us. It seemed like a mistake… I had to find an expla­na­tion other than the real one, which was that we were no more immune to misfor­tune than anybody else, and the idea that kept recur­ring to me, perhaps because of that pacing the floor with my father, was that I had inadver­tently walked through a door that I should­n’t have gone through and could­n’t get back to the place I hadn’t meant to leave. Actually, it was the other way round: I hadn’t gone anywhere and nothing was changed, so far as the roof over our heads was concerned, it was just that she was in the cemetery.

It’s not fair to describe So Long, See You Tomorrow as a book strictly about loss; the plot revolves around a murder, the details of which are revealed slowly. But all of the charac­ters feel loss of some form or anoth­er—death, betrayal, separation, regret.

It’s a beautiful book. You can probably find it in your local used-book store, and on Amazon.

The death of the master builder

Atul Gawande expanded a great piece in the New Yorker from 2007 into The Checklist Manifesto, a short, compelling read about how a simple tool can help humans tackle complexity.

Most of the book explores reducing human error in medicine (spoiler: good check­lists prevent mistakes). But Gawande includes a fasci­nating chapter on the construc­tion industry where he writes:

For most of modern histo­ry… the dominant way people put up build­ings was by… hiring Master Builders who designed them, engineered them, and oversaw construc­tion from start to finish, portico to plumb­ing. Master Builders built Notre Dame, St. Peter’s Basil­ica, and the United States Capitol build­ing. But by the middle of the twentieth century the Master Builders were dead and gone. The variety and sophis­ti­ca­tion of advance­ments in every stage of the construc­tion process had overwhelmed the abili­ties of any individual to master them.

The solution? A combi­na­tion of delega­tion, commu­ni­ca­tion, and checklists.

I see many paral­lels to the computing indus­try. Thirty years ago, Steve Wozniak designed and built a complete computer by hand, the now-legendary Apple I. Today, I carry a computer many orders of magni­tude more complex than the Apple I in my pocket: the iPhone. There’s no one person who can under­stand every single compo­nent of the iPhone and how they work together, let alone assemble one from scratch.

Our solution in both hardware and software is abstrac­tion. Different special­ists and compa­nies handle different compo­nents, and agree on inter­faces between those compo­nents, much like the plumbers and electri­cians and HVAC special­ists collab­o­rate on a skyscraper.

In software, abstrac­tions have evolved at the same speed as the under­lying complex­ity, so that appli­ca­tions like the webserver Nginx and the game Minecraft can still be largely written by one person. The tools just keep improving.

The Apple iPhone SDK is a great example of an excep­tional tool: for (almost) no cost, Apple offers devel­opers a complete coding environ­ment, UI compo­nents to make beautiful inter­faces, a distri­b­u­tion channel, and payment process­ing. It’s never been easier for a team of one or two people to make great software that reaches a large audience.

Moreover, program­mers have created many varieties of automated check­lists to fight against increased complex­ity, from unit tests to full functional tests that click on buttons within an app.

Without such tools the age of the programmer “master builder” would have ended long ago. I’m curious if we’ll ever reach a point where one or two people can no longer create meaning­fully useful applications.

The Checklist Manifesto can be found at Amazon and elsewhere.

We had grandma for Christmas dinner

Several years ago I decided to start collecting jokes.

I was inspired by this 2009 New York Times article quoting Robert Provine, a professor of psychology at the Univer­sity of Maryland, explaining that “[w]hat makes a joke successful are the same proper­ties that can make it diffi­cult to remem­ber.” Jokes are hard to remember because memory relies heavily on pattern-matching, and humor often arises directly out of breaks in our usual patterns.

So I made a conscious decision to remember jokes, much in the same way I made the decision to actively remember people’s names after reading Dale Carnegie. They’re both great party tricks.

Most of my close friends know my favorite jokes by heart; I habit­u­ally recite them in awkward conver­sa­tional pauses, at parties, in bed. This one has been in my reper­toire for years:

Did you hear about the two TV antennas that got married? The ceremony was boring, but the recep­tion was great.

I still think it’s funny, even if my girlfriend doesn’t.

When my friends could­n’t supply me with enough new jokes to annoy other friends with at parties, I turned to my Internet pal Google for a little assistance.

Google can answer almost any question that comes up in conver­sa­tion—who invented the zero, for example (long story, but big ups to al-Khwārizmī1), or when Paul Simon’s album Songs from the Capeman was released (1997, not that you asked)2. A search for “good jokes”, in contrast, turns upFuNNy JoKeS make life gOoD and HuMoRouS in the top spot, which gives us this gem:

We had grandma for Christmas dinner ?
Really, we had turkey !

This might be the most brilliant anti-joke ever written. Or maybe something was lost in translation.

Okay, the first result isn’t always the best. Let’s move on to #2, Each joke linked from its nearly illeg­ible homepage contains one or more jokes along with some (usually conser­v­a­tive) commen­tary on just how gosh-darn crazy our world has become, complete with rainbow WordArt headlines:

Even when they are readable, none of the jokes are funny.

The third Google result, smileJoke, brings some modern “so­cial web” flavor into the mix. smile­Joke allows users to submit ratings for each joke, and appar­ently, all the jokes have a rating of 1. This is not surprising given the material:

My wife had gained a few pounds. It was most notice­able when she squeezed into a pair of her old blue slacks. Wondering if the added weight was notice­able to everyone else, she asked me, “Honey, do these slacks make me look like the side of the house­?” “No, dear, not at all,” I replied. “Our house isn’t blue.”

Friends, these are the top 3 sources for “good jokes” on Google. I guess Google’s ranking algorithm doesn’t have a sense of humor. But the next time your girlfriend asks you whether her jeans make her look like “the side of the house­,” you now know how to get the laughs.

The best source I’ve found is, surprisingly, the Jokes subreddit. It suffers from the usual Reddit demon­s—trolls, memes and misogyny abound­—but some of the jokes are funny, which puts it in the top 0.001%. Recently, Reddit ranked this gem as the top joke of the day (revised for clarity):

Q: What do free health­care and good jokes have in common?
A: Ameri­cans don’t get them.

Not bad. Still, the Internet disap­points when it comes to humor.

Why is it so hard to find good jokes? Humor is subjec­tive, of course, but is it more subjec­tive than, say, music? Google and others have used machine learning to solve problems that once seemed insol­uble, to find patterns and meaning in vast troves of data.

How come no one has applied this technology to finding jokes that are actually funny?


1 Source: Wikipedia

2 Source: Allmusic

Great reads: Uncommon Carriers

After living in New York for a year and a half, I miss San Francis­co’s excel­lent used bookstores. I feel lucky to work just half a block from The Strand, but there’s something about a small bookstore’s curated selec­tion of used books that makes browsing more fun.

I was working in SF last week when I happened into Aardvark Books one night after dinner. Aardvark boasts a great “re­cent arrival­s” section, just a few shelves long but brimming with excel­lent, inexpen­sive reads. I randomly picked up a hardcover copy of John McPhee’s Uncommon Carriers, based mostly on its excel­lent cover art and a vague recol­lec­tion of having read some of his work in theNew Yorker. (It helped that some bookstore employee wrote in pencil on the first page, “Pretty good!”)

It was a lucky find. Uncommon Carriers explores freight trans­port and the people who work Ameri­ca’s trucks, barges, ships, planes, and trains, day and night. This might sound boring at first glance, but McPhee’s writing is strangely hypnotic and enthralling.

One piece in particular, Out in the Sort, kept me up late last night. The piece begins with a detailed descrip­tion of a lobster-catching opera­tion in Newfound­land, and uses the lobster compa­ny’s trans­port needs as a segue into a decon­struc­tion of how UPS operates. Describing their world­wide hub in Louisville, Kentucky, McPhee writes:

This labyrinth, which outthinks the people who employ it, is something like the interior of the computers that run it. Like printed circuitry, seven great loops, each a thousand feet around, are super­posed at right angles above other loops… Unending sequences of letters and small packages zip around these loops, while the larger packages follow one another on the belts, each package tailgating the one in front of it but electron­i­cally forbidden to touch it… Collec­tively, the loops are like the circuits in the mother­boards among the inter­face cards of a central processing unit wherein whole packages seeking specific airplanes are ones and zeroes moving through the chips.

There’s too much to glean from the piece (and from the book) for a short blog post, but I’ll pick a few tidbits. We learn that UPS employs college students to deal with “ex­cep­tion­s”—­pack­ages that require human inter­ven­tion. When the company experi­enced diffi­culty hiring enough students, it founded and endowed a college of its own, Metropolitan College, in concert with the Univer­sity of Louisville and other local schools. UPS employees also service Toshiba laptops on-site, and keep the largest supply of Bentley parts in the world. McPhee’s great writing and sense of humor keep everything interesting.

There are hundreds of other fasci­nating details. If you have a New Yorker subscrip­tion, you can read Out in the Sort on If not, I managed to find a copy online, which you can download from Mediafire while it lasts. Either way, if this sounds at all inter­esting to you, you should find a copy of Uncommon Carriers. I know I’ll be looking for more McPhee titles next time I hit a used bookstore.

Great Reads: The Sense of an Ending

…when you are young, you think you can predict the likely pains and bleak­nesses that age might bring. You imagine yourself being lonely, divorced, widowed; children growing away from you, friends dying. You imagine the loss of status, the loss of desire—and desir­abil­i­ty… What you fail to do is look ahead, and then imagine yourself looking back from that future point. Learning the new emotions that time brings. Discov­er­ing, for example, that as the witnesses to your life dimin­ish, there is less corrob­o­ra­tion, and there­fore less certainty, as to what you are or have been. Even if you have assid­u­ously kept record­s—in words, sound, pictures—you may find that you have attended to the wrong kind of record-keeping.

Sense of an Ending is a short and wonderful book, a slim 180 pages readable in a single sitting. There’s much to savor, though, and like Marilynne Robinson or Alice Munro, Barnes chooses every word carefully and precisely. Highly recommended. Amazon

6 Reasons to Move to New York City

New York City lacks the startup density of Silicon Valley, but there are plenty of reasons to start your next company here:

1. A great (and growing) startup scene. Soho, Union Square and the Flatiron district form the new Silicon Alley, where you’ll have your pick of compa­nies, meetups and events. Great startups are doing great work here across industries—including tumblrfoursquare10genBetaworksturntable.fmEtsy,Skillshare, and Harvest, among others 1. New York also has a sizable angel and VC community 2.

2. Bubble-free. SF often feels like a company town; in contrast, New York is a national hub for publish­ing, adver­tis­ing, fashion, food, and finance, to name a few. Being in the center of all these indus­tries is inspir­ing, and your startup can take advan­tage of this diversity.

3. The singles scene. Some folks might rank this as #1; I’m trying not to assume too much. But if you’re a single straight guy or gal in SF or Mountain View, you (or a friend) have likely complained about the singles scene in the Bay Area.

Forbes ranks New York as the best city for singles, putting it above San Francisco, which clocks in at #7 3. For single guys, the numbers don’t lie—there are 210,820 more single women than men in the New York metropol­itan area, while the Bay Area boasts a surplus of 65,000 men. 4 

Plus, being a hacker/en­tre­pre­neur is more unique in New York—telling someone you make iPhone apps elicits inter­est, not eye-rolls. (Try it.)

4. Official support. Mayor Bloomberg wants to turn New York into a tech hub, and city officials reach out to local entrepreneurs. The NYC Economic Development Corporation offers great resources including info on city incen­tives and discounted office space for startups.

5. The city never sleeps. NYC is much friendlier to the late-night hacker’s sched­ule—­sub­ways and buses run 24/7 and great restau­rants stay open till 2am or 4am. Contrast this with San Francisco, where it’s hard to get good food after 11pm, even on a Saturday night.

6. The upstart startup hub. This one is hard to quantify, but there’s something exciting about being part of the NY startup culture because it is less estab­lished than SF—y­ou’ll find plenty of room (and enthu­si­asm) for starting a new meetup, for example. There’s an energy in the air here, a sense that we are all part of something new and growing and awesome.

If you’re living in SF or elsewhere and looking for a change, come visit NYC and see if it’s right for you.

I’ll even buy you a coffee.


1 See a bigger list of NY-based companies here: Internet Made in New York City.

2 The New York market on AngelList hosts an excel­lent list of NYC-based investors and angels.

3 Source: Forbes

4 Source: Boston Globe

Great reads: Thinking, Fast and Slow

“The tendency to see patterns in randomness is overwhelming…”

Daniel Kahneman’s Thinking, Fast and Slow made many “best of 2011” lists this year, and deservedly so. Plenty of books on the system­atic faults of the human mind have made the rounds, from Ariely’sPredictably Irrational and its followup to Nassim Taleb’s Fooled by Randomness and The Black Swan.

Fooled by Randomness was a great book marred by the pompous­ness of its author. In fewer words (and with much less ego), Kahneman covers similar terri­tory in more depth and backed by better research:

How many good years should you wait before concluding that an invest­ment adviser is unusu­ally skilled? How many successful acqui­si­tions should be needed for a board of direc­tors to belive that the CEO has extra­or­di­nary flair for such deals? The simple answer to these questions is that if you follow your intuition, you will more often than not err by misclas­si­fying a random event as system­atic. We are far too willing to reject the belief that much of what we see in life is random.

I will do my best to remember the above quote whenever I jump to conclu­sions about a startup, an entre­pre­neur, even an A/B test.

There’s too much in the book that’s applicable to anyone starting a business, or inter­preting analytics from your website, or trying to make rational decisions. Instead of quoting from every chapter, why not just check it out for yourself? (No affil­iate link, I promise.)

Long-term thinking

Steven Levy did a great interview in Wired of Amazon CEO Jeff Bezos. The money quote, for me:

If every­thing you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people, because very few compa­nies are willing to do that… At Amazon… [w]e’re willing to plant seeds, let them grow—and we’re very stubborn. We say we’re stubborn on vision and flexible on details.

I know I’ve person­ally been too focussed on the short-term in the past—and any casual browser of the new startups on Angel­List will see plenty of fast-follow startups with little to differ­en­tiate them from the competition.

Bezos is a great CEO, and doesn’t get the credit he deserves. Amazon is an amazing company.

Talent is the limiting factor in startup growth

It is much easier to start a web startup in 2011 than it was in 1995, or even 2005.

You don’t need upfront capital to buy racks of machi­nes, miles of CAT-5, routers and load balancers, redun­dant power and backbone connec­tivity — all are avail­able on-demand from Amazon for pennies an hour.

You don’t need to write server-side Web frame­works — you have your pick in nearly any language. In fact, you have your pick for any number of services you might once have had to develop or maintain yourself: email deliv­ery, web analyt­ics, A/B testing, server monitor­ing, file hosting.

Because the infrastruc­ture cost of starting a startup has gone down, the amount of money you need from investors to get your company off the ground has also decreased. You can build a proto­type in a few months (as every YC class demon­strates, twice a year) for less than $20,000.

And there are more people to give you that money — VCs, ex-Googlers and Facebook­ers, other angels, startup accel­er­a­tors and incubators.

But ask any startup around what they really do need right now, and the answer is clear — great technical talent. Startups of all sizes are competing for a small pool of highly skilled candi­dates, and in startup hubs like San Francisco and New York the compe­ti­tion for engineers is fierce. This scarcity has persisted despite consis­tently high national unemployment rates.

And because it has become so easy and cheap to start a startup, convincing great engineers to join an existing startup has gotten much harder.

All of these trends will continue — infrastruc­ture costs will continue to decrease, tools for creating web products will get more sophis­ti­cated, and more people (and more kinds of people) will be investing in startups at all stages.

But those startups who can hire and retain great talent will achieve greater success because they have the capacity to out-execute their peers.