Why we built Lookmark

Reposting from the Lookmark blog, with apologies to the family member whose Facebook update I single out in this post. If you want to skip ahead, just sign up for Lookmark and tell me what you think.]

When I first joined Facebook, I updated my status and added photos often. It was a place for me and my actual friends to have actual conver­sa­tion­s—a welcome change from Myspace, which had been filled with animated GIFs and lots of quote-unquote “friends.”

Five years later, I barely update my Facebook at all—­maybe once or twice a month. When this update from a family member appeared in my News Feed a few months ago, I knew my relation­ship to Facebook had changed permanently:


Facebook has achieved their goal of building the best social graph on the Web. And that’s why I stopped updat­ing—every single update is shared to 700 current friends, former friends, random people from high school, coworkers and former cowork­ers, profes­sional contacts, immediate family, not-so-immediate-family, and randoms. Each update now forms a piece of our Timeline, to chron­icle all of our life events for posterity.

I stopped sharing because I don’t want every link I share to be perma­nently archived and viewed by any of my friends and family, or the HR depart­ment for my next job, or my future kids (if Facebook is still relevant by the time they’re old enough to use their iPhone 19).

This is exactly the problem that startups like Path are trying to solve. Path is meant to be a new, virgin terri­to­ry—a place for your real friends and family. It’s also the reason that I will never use Facebook Social Reader apps, like the Washington Post app, which automat­i­cally share all articles you read to your Timeline. I don’t want to share every article with my 700 friends, and I don’t want to perma­nently, publicly archive it on my Timeline. And I don’t want to see every article my 700 friends read, either.

Automatic sharing can be very compelling, though. When Last.fm launched (way back in 2002!) it was one of the first services to take advan­tage of automatic sharing—by simply installing the Audio­Scrob­bler plugin, you could share every­thing you played in iTunes, automatically.

While brain­storming ideas for new apps, I thought: “What about a Last.fm for news, a browser plugin that shares what you read automat­i­cal­ly?” I built a proto­type of the concept in a few days back in April to test the concept. When I showed it to my cofounders, we all agreed that it was very compelling, even with a total of 3 people using it—so we’ve spent the last few months building and refining the product. We call it Lookmark.

Lookmark is a Chrome exten­sion that automat­i­cally and privately shares what you’re reading from sites you choose (like the New York Times or links from Hacker News) with the friends you choose. Lookmark solves many of Facebook’s sharing problems because we designed from the ground up it for private sharing with a small group of close friends. It’s become an addic­tive source of news and conver­sa­tion over the past few month­s—and we’re just getting started.

We’re slowly opening Lookmark to new users. Inter­ested? Sign up at Lookmark.com and add me as a friend. I’d love to hear your feedback.

The joy of code

I’ll admit it—I love program­ming, and I have since I was a kid. This makes me a nerd, but at least I’m an honest nerd.

Code is a unique medium. There’s no activity better suited for the achievement of flow, which Wikipedia defines as “the mental state of opera­tion in which a person in an activity is fully immersed in a feeling of energized focus, full involve­ment, and success in the process of the activity.”

There’s something really special about hacking away on something and then, after hours or days of strug­gle—­making it actually work. And that joy of comple­tion, of having heroically strug­gled and then solved the problem, happens again and again. A good programmer working on a hard problem has little dopamine bursts firing in their brain all day.

I’m still not over it. And I think many people would benefit from (and enjoy!) learning how to code.

A computer on every desk, and in every home

Steve Jobs gets most of the credit for being a revolu­tionary technology leader, but Bill Gates was equally, if not more, vision­ary. In 1980, Gates defined the mission of Microsoft “A computer on every desk, and in every home.”1 It’s diffi­cult, now that we we all have incred­ibly powerful computers in our homes, cars, and pockets, to remember how insane this was at the time.

Microsoft executed that insane vision nearly flawlessly.

Computers became integral to many jobs in the 1980s and especially the 1990s, as the Internet penetrated workplaces and Microsoft’s Office software became ubiqui­tous. New software dramat­i­cally changed the nature of office work.

We’re about to experi­ence another dramatic change. The New York Times recently published The Age of Big Data. You should read it, but let me summa­rize: As computers become part of more things (phones, cars, toast­ers), they will generate more and more data, and we’ll need smart analysts to make sense of it all. Office workers will experi­ence a big shift like they did in the 90’s,as the ability to analyze data becomes more integral to every job—from manage­ment, to market­ing, to design, to front-line information workers.

I believe that simple computer profi­ciency will no longer suffice as software takes over more aspects of work and life. Not that it’ll be neces­sary for all office workers to become masterful program­mers; but those who can write simple programs to help automate their daily work and make sense of piles of data will have an advantage.

This change means more people will have the oppor­tu­nity to experi­ence the joy of code. Unfor­tu­nately, learning requires hard work, and most people haven’t been educated in the basics of computational thinking.

How will all these people learn how to code?

Learn BASIC now

When I was around eight years old I asked my parents to buy me a book called Learn BASIC Now. (Amazingly enough, Amazon still sells the book for a penny.) I remember sitting down at the computer in our living room and working through the book’s exercises in Quick­BA­SIC, a program­ming language included with most PCs at the time.

Within a few weeks I was able to make simple video games, and by the time I was in middle school I was asking my parents for related stuff—­more books, then an Internet connec­tion, then a domain name (which cost $100 at the time!) and Web hosting service, so I could help others learn.2

One of the most popular games I wrote as a kid had primi­tive graphics that looked like this:

Lander QBasic game

This wasn’t state-of-the-art for 1994, but it was playable and maybe even fun. I called the game Lander. The goal was to safely pilot your ship to a landing strip on the moon, avoiding obsta­cles along the way3. I really enjoyed making games and sharing them with friends and on the Web—it was a great motivator for me to improve as a programmer.

But what worked for me would­n’t work today. The everyday systems we use have become more compli­cated, and it’s harder to create a simple program of acceptable quality.

Most DOS users would be able to find and run GW-BASIC or Quick­BA­SIC, two program­ming languages that shipped with the operating system—but although current Macs ship with several powerful languages installed, most newcomers would­n’t know where to find them. If they could, the Terminal would seem scary because the Mac user inter­face covers up its text-based underpinnings.

Even then, creating a text-based program would­n’t seem that impres­sive—the simplest iPhone apps come with beauti­ful, animated inter­faces that react instantly to our touch, courtesy of Apple’s design tools. A text-only number guessing game seems pretty lame by comparison.

Learning to code in 2012

So how does one get started, given the complexity of today’s computers and the high expec­ta­tions of users? Thank­fully, many startups and univer­si­ties have begun tackling the problem in innovative ways.

Udemy offers a class by Zed Shaw called Learn Python the Hard Way for $29. Zed also offers a free HTML book for the course. Zed’s premise is that the best way to learn is by doing, so you’ll be doing a lot of typing. This seems to me like a Good Thing.

Another startup called Codecademy offers a unique way to learn—sim­ple, step-by-step tutorials that run in your web browser, allowing you to inter­ac­tively learn how to code without installing any software or buying any books. They’ve recently received a lot of press for a 52-week program called Code Year. When you sign up for Code Year, you receive a weekly code lesson via email which you can complete on their website. There are also Q&A forums where you can get help with each lesson. Hundreds of thousands of people have signed up, including high-profile folks like Mike Bloomberg.

There are a couple of poten­tial downsides to Code Year and Codecad­emy. Currently, they only teach Javascript, which I would­n’t recom­mend as a first language for a begin­ning program­mer. Second, the inter­ac­tivity of the lessons hides some of the reali­ties of coding. Program­ming is a unique activity because for the most part it’s a very solitary journey—y­ou’re alone with your work, shuffling logic around your brain. I’m curious if the folks who go through Codecademy tutorials are ready for the kinds of frustra­tions they’ll face—Learn Python The Hard Way is much more like “actual” programming.

There are tons of other great resources, far too many to list here. The Khan Academy has great video lectures; Google offers excellent Python tutorials; MIT offers their Intro to Computer Science and Programming, and Stanford offers an Intro to Computer Science and Programming Methodology..

Regard­less of which method you end up trying, if you want to learn, find something that appeals to you and stick with it. Don’t get discour­aged; the rewards will reveal themselves over time.


Learning to code is like learning to play an instru­ment. Some people will achieve basic easier than others. But for nearly every­one, becoming a good programmer will take many hours of delib­erate practice; it’s not something you can achieve in hours or days, no matter how many tutorials you read.

To be a great program­mer, you have to really want to learn; it’s not going to happen in a day or a week. Thank­fully, you probably don’t need to become a great programmer unless you plan to pursue a career in software engineer­ing. You can learn enough code in a short time to improve and automate some of your daily work.

I hope that the changes ahead as we enter the “Age of Big Data” give more people the oppor­tu­nity to experi­ence the joy of code.

I’d love to hear from people who want to learn code. If you find a particular resource linked in this post helpful (or terrible), or you think I’ve missed something, please let me know.


1 The full quote is actually “A computer on every desk and in every home, all running Microsoft software.” Steve Jobs deserves praise for rescuing Apple in the early 2000s and taking leader­ship of the technology indus­try, but it was Microsoft who really brought personal computers to the masses.

2 Sure enough, some of my tutorials are still floating around the Web. This taught me an early lesson in how anything you put on the Internet never goes away.

3 The game borrowed from similar “land the ship” games at the time. A bit more expla­na­tion on its mechan­ics: the turquoise strip at the bottom of the screen repre­sents a lunar landscape; the red flaming comet is an obstacle to avoid; and the shaded golf ball-like things are supposed to be planets to dodge. (Don’t ask me why planets are hovering above the moon’s surface; it made sense at the time). The code for this game still floats around the internet—it’s embarrassing.

Starting up again

It’s been almost five years since I started my last startup.

I remember clearly the heady blend of optimism and anxiety that came with filing our incor­po­ra­tion papers, followed by the pride and sweat and joy of brain­storm­ing, building and launching our first real product.

I just started a new startup with two great friends, Amit and Drew, and those feelings are back. The five inter­vening years have brought successes, failures, and hard-learned lessons, yet I could­n’t feel more sanguine about the future.

I should probably be more worried about the months ahead­—there’s nothing to anchor me and my cofounders except our own deter­mi­na­tion and wits. It’s a long, hard road, and startups fail for a lot of reasons.

Yet despite all that, I still feel optimistic.

I’ll do my best to correct my mistakes from my last go-round1. Yet even if I fail this time, I feel like I’ve already won. Inertia is one of the strongest forces in the world—there are so many different things acting to prevent one from doing something, from making something. And somehow, we’ve managed to give ourselves the oppor­tu­nity to really create something awesome.

All we have to do now is make the most of it.

1 See my previous post about putting your career in stealth mode for one of the mistakes I made.

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.

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

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.