Alex Payne writes online here.

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The five most recent posts.

Back To My Roots

Since my life was turned upside-down in mid-2012, I haven’t had a good answer to the question “what do you do?”. I’ve been doing things, of course. I’ve traveled, consulted, advised, invested, and written. I spent a lot of time in museums and a lot of time staring at the ocean. I did things I wanted to do, and I did things I needed to do.

This has been the first time in over a decade that I haven’t had a full-time job for a long stretch. My knee-jerk response to that lack of definition was to jump back into a familiar structure. At the beginning of 2013, I rushed into a role at a startup that turned out not to be the right fit. Since then, I’ve cautiously evaluated the opportunities that have presented themselves.

To make things a little more surreal: a few weeks after I turned 30 this past October, Twitter went public, confirming that I never need to work again. (I’m still getting my head around that.)

So, what do you do when you don’t need a job?

I considered a bunch of options. Agonized, even. I thought about going back to school for subjects as diverse as computer science, philosophy, art, political science, economics, and architecture. I thought about writing full time. I was approached by VC firms, and by a number of startups looking for technical leadership. At my most frustrated, I even thought of pulling a jwz and flaming out of tech entirely, maybe to make music or volunteer all the time or who knows what.

None of that felt right.

Finding DOBT

When asked about my background, I usually mention that I grew up in DC and got my professional start there building software for campaigns and non-profits. This was well before the technology-driven victories of the Obama campaign, and even before Howard Dean’s pioneering use of online fundraising.

One of the instrumental figures in the Dean campaign’s use of technology was Clay Johnson, who I first met during Twitter’s breakout year at SXSW 2007. Clay immediately went on my mental list of people I’d like to work with someday. Since then, Clay has led efforts to open public data at the Sunlight Foundation, written an influential book on conscious information consumption, and has been fighting for procurement reform and innovation as a Presidential Innovation Fellow.

Several weeks ago, I found myself sitting on the couch, a little demoralized after exploring yet another job opportunity that didn’t feel right. My lovely and talented girlfriend put on an episode of The Daily Show in which Jon Stewart was (justifiably) ranting on a recurring topic: the inefficiency of the VA. At that moment, my train of thought: “Someone in tech needs to do something about this. I should do something about this. Who do I know who’s probably trying to do something about this? Clay.”

I’ve joined up with Clay, his talented technical co-founder Adam, and government relations whiz Sid at The Department of Better Technology. Simply put, we’re making software that makes government work better.

Now this feels right.

Company Values

DOBT operates by a set of values that have, through experience, become very important to me: allowing and encouraging remote work, operating internally without titles, self-directed time management, and a non-dogmatic approach to building quality software products. I’ve seen enough business madness, and DOBT eschews it all. We’re working to build something sustainable at both a financial and human level.

Supporting diversity in tech initiatives has been a personal cause, so it was equally important to me that the people I work with understand the necessity of overturning the exclusionary monoculture that so defines our industry today. DOBT is not only a company with a commitment to diversity, but we’re advocating for a streamlining of minority- and woman-owned government contracting set-asides. Those reforms will unlock some five billion dollars for workers who have been economically disadvantaged.

Lastly, what attracted me to DOBT was the idea of working with a group of people who believe in government, and believe that technology can be a force for positive momentum in government. The debacle is just one example of what an uphill battle we have to fight, but it’s unquestionably worth the effort. For all its faults and frustrations, government is a pillar of civilization and deserves a foundation of well-crafted and open technology.

I still believe in technology, I still believe in government, and I still believe in startups. I’m happy to be putting that all together again with my new colleagues at DOBT. I hope you’ll consider joining us.

Feb 11, 2014

Bitcoin, Magical Thinking, and Political Ideology

Last week, investor Chris Dixon posed a provocative dichotomy when introducing his employer’s USD $25M investment in Bitcoin service Coinbase:

“The press tends to portray Bitcoin as either a speculative bubble or a scheme for supporting criminal activity. In Silicon Valley, by contrast, Bitcoin is generally viewed as a profound technological breakthrough.”

Now working at vogue venture capital firm Andreessen Horowitz, Dixon is in a fine position to speak for Silicon Valley. But to the extent that the Valley is a placeholder for the technology industry at large, I beg to differ. Bitcoin is “generally viewed” quite differently.

Most charitably, Bitcoin is regarded as a flawed but nonetheless worthwhile experiment, one that has unfortunately attracted outsized attention and investment before correcting any number of glaring security issues.

To those less kind, Bitcoin has become synonymous with everything wrong with Silicon Valley: a marriage of dubious technology and questionable economics wrapped up in a crypto-libertarian political agenda that smacks of nerds-do-it-better paternalism. With its influx of finance mercenaries, the Bitcoin community is a grim illustration of greed running roughshod over meaningful progress.

Far from a “breakthrough”, Bitcoin is viewed by many technologists as an intellectual sinkhole. A person’s sincere interest in Bitcoin is evidence that they are disconnected from the financial problems most people face while lacking a fundamental understanding of the role and function of central banking. The only thing “profound” about Bitcoin is its community’s near-total obliviousness to reality.

Regulation and Other Minor Details

Bitcoin owes its present flexibility to a lack of regulation (or, more accurately, a lack of understanding around existing regulations and/or unwillingness to comply with them). If the broader Bitcoin experiment doesn’t implode, the currency will be regulated just as any other. In this best-case scenario for Bitcoin, what of the benefits Dixon claims?

We’re told that Bitcoin “fixes serious problems with existing payment systems that depend on centralized services to verify the validity of transactions.” If by “fixes” you mean “ignores”, then yes: a Bitcoin transaction, like cash, comes with the certainty that a definite quantity of a store of value has changed hands, and little else. How this verifies any “validity” or cuts down on fraud I’m not sure; stolen Bitcoins are spent as easily as stolen cash, which is why theft of Bitcoins has been rampant.

With those risks in mind, are the fees that existing card networks and payment processors charge – Dixon’s “roughly a 2.5% tax on all transactions” – outrageous, or are we perhaps collectively subsidizing the cost of fraud prevention and regulatory compliance? In what plausible universe will legitimate Bitcoin transactions be allowed to take place without such protections, and thereby without the associated costs? (Incidentally, you can expect to pay a similar “tax” just to reclaim some semblance of the anonymity that Bitcoin fails to provide in the form of mixers, a zingy term for money laundering.) To be sure, the credit card companies have fattened their margins beyond the raw cost of moving money around, but we have a miraculous salve for this called regulation.

If Bitcoin’s strength comes from decentralization, why pour millions into a single company? Ah, because Coinbase provides an “accessible interface to the Bitcoin protocol”, we’re told. We must centralize to decentralize, you see; such is the perverse logic of capital co-opting power. In order for Bitcoin to grow a thriving ecosystem, it apparently needs a US-based, VC-backed company that has “worked closely with banks and regulators to ensure that the service is safe and compliant”.

And Coinbase certainly feels, uh, compliant. It took me over a week to use the service to turn US dollars into a fraction of a Bitcoin, an experience that coupled the bureaucratic tedium of legacy consumer financial services with the cold mechanization of notoriously customer-hostile PayPal, but with the exciting twist that I have no idea from moment to moment how much my shiny new Internet money is actually worth.

Magical Thinking

While most of the claims around Bitcoin are merely wince-inducing, there is one that deserves particular attention: that Bitcoin is “a way to offer low-cost financial services to people who, because of financial or political constraints, don’t have them today.”

Economic inequality is perhaps the defining issue of our age, as trumpeted by everyone from the TED crowd to the Pope. Our culture is fixated on inequality, and rightly so. From science fiction futures to Woody Allen character sketches, we’re simultaneously alarmed and paralyzingly transfixed by the disappearance of our middle class. A story about young people dying in competition with one another just to continue lives of quiet desperation isn’t radical left-wing journalism, it’s the pop fiction on every teenager’s nightstand and in every cinema right now.

With this backdrop of looming poverty, nobody can reasonably deny that the euphemistically “underbanked” are in desperate need of financial services that empower them to participate fully in the global economy without fear of exploitation. What’s unclear is the role that Bitcoin or a similar cryptocurrency could play in rectifying this dire situation.

The push toward Bitcoin comes largely from the libertarian portion of the technology community who believe that regulation stands in the way of both progress and profit. Unfortunately, this alarmingly magical thinking has little basis in economic reality. The gradual dismantling of much of the US and international financial regulatory safety net is now regarded as a major catalyst for the Great Recession. The “financial or political constraints” many of the underbanked find themselves in are the result of unchecked predatory capitalism, not a symptom of a terminal lack of software.

Silicon Valley has a seemingly endless capacity to mistake social and political problems for technological ones, and Bitcoin is just the latest example of this selective blindness. The underbanked will not be lifted out of poverty by conducting their meager daily business in a cryptocurrency rather than a fiat currency, even if Bitcoin or its ilk manages to reduce marginal transaction costs (at scale and in full regulatory compliance, that is). But then, we should note that Dixon wasn’t talking about lifting anyone out of poverty, just “offer[ing them] low-cost financial services”. Also notable is that both Andreessen and Horowitz supported Mitt Romney’s failed presidential bid, giving us some insight into the likely level of concern for economic inequality around Dixon’s office.

In Bitcoin, the Valley sees another PayPal and the associated fat exit, but ideally without the annoying costs of policing fraud and handling chargebacks this time around. Bankers in New York and London see opportunities for cryptocurrency market-making. International investors see the potential for arbitrage and are taking advantage of cheap electricity, bringing the environmental destruction of real-world mining to the brave new world of digital money.

In other words: Bitcoin represents more of the same short-sighted hypercapitalism that got us into this mess, minus the accountability. No wonder that many of the same culprits are diving eagerly into the mining pool.

Moving Past The Failed Techno-Libertarian Agenda

For the past few months I’ve been giving a talk, informed largely by feedback on my post about the tradeoffs of joining startups earlier this year. The talk delves into the history of Silicon Valley and venture capital, tying past to present. Though I cover a lot of ground in a short sprint, I hope my message is clear: that the dominant socio-political ideology of Silicon Valley has failed to deliver sustainable profits to the broader investor class while technological innovation has slowed and jobs have dried up. It’s time for new thinking.

Bitcoin is not without its left-wing supporters, but I think it’s safe to say the currency has mostly proven to be a rallying point for those who see the state and central banks as little more than obstacles to a libertarian techno-utopia, a worldview perhaps best captured in The Californian Ideology. In this sense, Bitcoin is ready-made for a cultural moment when Silicon Valley ideologues are discussing plans for a new opt-in techno-centric society and sliding so far right that a return to monarchy is on their table.

Working in technology has an element of pioneering, and with new frontiers come those who would prefer to leave civilization behind. But in a time of growing inequality, we need technology that preserves and renews the civilization we already have. The first step in this direction is for technologists to engage with the experiences and struggles of those outside their industry and community. There’s a big, wide, increasingly poor world out there, and it doesn’t need 99% of what Silicon Valley is selling.

I’ve enjoyed the thought experiment of Bitcoin as much as the next nerd, but it’s time to dispense with the opportunism and adolescent fantasies of a crypto-powered stateless future and return to the work of building technology and social services that meaningfully and accountably improve our collective quality of life.


First off, thanks to everyone who read an early draft of this post.

I wrote the vast majority of this post before today’s sizable Bitcoin crash, for what it’s worth (and, honestly, from moment to moment, who knows?).

At time of writing, I own a fraction of one Bitcoin. A portion of that was mined on a laptop several years ago as part of the Deepbit pool. More recently, I purchased some BTC with US dollars on Coinbase. I own this small amount of BTC because I’m largely in the “Bitcoin is a worthwhile but flawed experiment” camp, and I wanted to try using the currency for my personal edification. Several readers asked me to be harsher and more conclusive on the economic fundamentals of Bitcoin. I chose not to out of deference to the experimental potential I saw in the project, warts and all. Bitcoin’s, er, creative take on economics and monetary theory is well dealt-with elsewhere.

I was previously CTO at online banking service Simple. While that experience has informed my thinking on the role of technology in consumer finance, I am not aware of Simple’s strategy with regard to Bitcoin and this post should not be construed as representing the opinions or direction of that company.

I am on hiatus from Twitter through the winter holidays. If you would like a response to any comment about this post, please email me.

Dec 18, 2013

Switching Season Report, 2013 Edition

Every couple years I get the urge to peek out of my Apple-furnished hole and survey the landscape of alternative devices and operating systems. I call this urge switching season, and I give into it despite having laid out my own rules for computing happiness years ago. I figure that the least I can do when the urge to switch strikes me is to share what I’ve learned in the hopes that it saves other people some time.

When I first wrote about switching season, a debate was raging regarding Apple’s developer-hostile stewardship of their App Store, a debate which had a sense of urgency in the context of the iPhone’s precedent-setting ascendancy. While Apple may no longer have the raw lead in mobile devices sold, it’s widely acknowledged that users of Apple devices spend more money on apps and app-mediated purchases. Whatever debate was happening around the fairness of the App Store has since been set aside because C.R.E.A.M.

So while the bitter pill of the App Store has long since been swallowed by the developer community, there are still plenty of reasons to be wary of Apple:

  1. Despite widespread coverage and ensuing outcry, the labor practices of Apple’s suppliers continue to be abhorrent.
  2. Apple conspiring with publishers to fix e-book prices.
  3. Apple allegedly evading billions of dollars in US taxes.
  4. The questionable aesthetic choices in iOS 7. I feel that the jury is still out until they ship, but I know some people who took the official announcement video of the iOS 7 design as a death knell for Apple, or at least their personal iOS usage.
  5. iCloud. Personal computing is moving ever more into the cloud and Apple’s implementation is unpopular with developers and users alike.
  6. OS X. Apple’s desktop operating system releases seem to get progressively more paltry every year. When a banner feature for Mavericks is bringing Apple’s miserable maps app to the desktop, there’s cause for concern. It feels as if Apple is gradually draining resources away from OS X in hopes that desktop computing will simply die off.
  7. The rising sentiment that Apple is a rudderless ship without Steve Jobs, and that to buy their products now is to invest in a dying ecosystem.

Concerns aplenty, albeit of varying degrees of concreteness. But enough to motivate an exploration of what else is out there. Here’s what I found this time around.

Android Hardware

Over the past several weeks I’ve spent time with three of the best-reviewed Android devices on the market: the HTC One, Samsung’s Galaxy S4, and the just-released updated Nexus 7 tablet. I ran Google Play Edition Android 4.2/4.3 on all three, but I’ll address the hardware before the software.

The HTC One is the only non-Apple phone I’ve used that approaches the build quality of iPhone 5. The One’s pronounced seams don’t permit it the feeling of total structural integrity that Apple’s phone boasts, but as the reviews say, it feels like premium hardware. Its internal speakers are fantastic, putting both iPhone and iPad to shame. Unfortunately, even for someone who’s had an octave-plus reach on the piano since childhood, it’s simply too large for comfortable one-handed use. Reaching the right-hand side of the screen while holding the One in your left hand is a lost cause. The phone’s expansive size coupled with its weighty metal case make it unsuited to traveling in a pants pocket. So, premium qualities aside, the HTC One is an ergonomic non-starter; it quite literally didn’t fit comfortably into my daily routine.

The Galaxy S4 does not feel like a premium product. It is plasticky and sort of embarrassing to carry around, though its cheapness does lend it a sense of devil-may-care durability. But the S4 is slim, light, and fits much better in the hand, and for that reason wins out over the HTC One in my book. It may not sound as good as the One, but the Samsung’s screen is nice, and it seemed comparably speedy when Android was behaving. In a nutshell, the Galaxy S4 is uninspired but good. I’d recommend it to someone who wanted an Android phone today.

The Nexus 7 tablet’s screen is as surprisingly nice as you’ve heard, but it’s just not big enough for content to stretch out and breathe easy. Otherwise, it is hardware that looks every bit its modest price. The Nexus 7 is a comfortable weight and size for reading whether held in one hand or two. The exaggerated, unbalanced bezels on its front face drove me nuts, though. It felt silly to carry a seven inch tablet when the Galaxy S4’s screen approaches five inches, leaving the Nexus 7 in an uncanny valley between a large phone, a Kindle Paperwhite, and a full-sized tablet. Theoretically the Nexus 7 could have replaced the e-book reader and full-size tablet, but using it was so squinty and pleasureless that I happily parted with it.

With no particular victories on the hardware front, on to the software side of today’s Android.

Android Software and UX

The Android operating system itself, in its unsullied Google-prescribed formula, is substantially better than it was even two years ago. There are still homely corners of the OS itself, but delightful interactions abound amidst the Tron-like Holo style. Customizing Android, as is the OS’s Linux-derived birthright, now seems unwarranted. The app selection in Google’s Play Store is vastly improved as well. Many brand name Android apps like Foursquare and Meetup are comparable to their iOS counterparts in both features and style. You can even have The Economist on your Android, and if that isn’t a mark of civilization I don’t know what is.

If you are not deeply committed to the Google ecosystem, though, the pleasures of today’s Android soon dry up. I recently de-Googled my setup and workflow (more on this another time), and so found myself resorting to unreliable third-party apps to make Android work halfway decently with open standards like IMAP, CalDAV, and CardDAV. (iOS, by contrast, works well with these standards out of the box; interacting with the Debian-powered personal VPS that replaced Google Apps for me is more seamless on iPhone than on Android, weirdly.) While you can put a “debloated” ROM on your Android device and use only the Google products you choose, you’ll find this creates more friction than relief. Android remains a loss-leader for the Google AdWords money printing machine, and the OS reminds you of that at every turn. No wonder Samsung is investing in its own Linux-based mobile OS, Tizen, even as it sells some of the most popular Android phones on the market.

“Fragmentation” is a heated word in the Android world, one perhaps bandied about too often by critics given the mobile OS’s massive adoption rate. That said, even when using straight-from-the-Google-tap Android on top-tier devices you feel the effects of fragmentation. The Galaxy S4 has dedicated physical buttons for bringing up a contextual menu and going backwards in the stack of interactions. The Nexus 7 presents these buttons in software, but differently, moving the button for the contextual menu to some ellipses that show up in the upper-right corner of the screen. The HTC One repurposes the company logo that mars its front face as a button that, when tapped, shows recently used apps. This too is done in software on the Nexus 7, but on the S4 by tapping the iPhone-like physical “home” button twice. Even in 2013, Android can’t seem to agree what the fundamental, always-available actions are and how they should be presented to the user. As a consequence, I found myself hitting the wrong buttons after moving from one device to another throughout my day.

Everything from Android’s name to its styling speaks to an aesthetic that’s technical and a touch retro-futuristic. After years on iOS, parts of Android look and feel cool, but the slightly anxiety-inducing cool of science fiction. The skeuomorphic approach that’s now been abandoned in iOS 7 may have been goofy, but it was the logical extreme of Apple’s clear intent that the iOS experience should blend seamlessly into the real world. Android exists primarily in digital space; iOS is largely an extension of the physical. Android was earlier to the trend towards flat design, but its flatness is cold and computational. The flattening of iOS in the upcoming release retains light and dimension while borrowing from print design traditions. It remains to be seen whether Apple’s approach with have legs, but Android could stand to take some further risks in the design department to make the OS humane and approachable.

The Holo theme – while fine for widgets, the Settings app, and other essential bits of the OS – evidently affords too few guidelines and interactions to steer the development of full-fledged apps. The best Android apps either invent their own UIs wholesale or borrow from their iOS counterparts. Holo interface elements, then, intrude on those custom UIs in context menus and dialogs. As with the fragmented button roulette issues described above, these factors illuminate Android’s lingering incoherency. Let’s not even speak of the system fonts, ugly but ignorable on a phone and downright offensive on a tablet. No, while much improved from several years ago, one does not use Android in 2013 for its looks.

Nor, unfortunately, for its stability. Everything from third-party apps to the Settings app and system launcher crashed with alarming frequency. I had a couple of days of reliable performance from the S4, but pretty soon it was running hot, draining battery like mad, and crashing frequently. This with essentially no customization, and even a highly recommended power management app policing cycle-hungry apps. Yikes.

Android is presently the only fully-baked mobile operating system that’s more open source than not, but other such efforts are coming to market. Mozilla has their Firefox OS, which seems to be targeted mostly at low-end phones and looks somewhat like Palm’s failed WebOS. Canonical has their own phone thing which seems to be built around the notion that people want to use their mobile devices as full-fledged PCs; where it doesn’t cater to that questionable idea, it seems to offer the usual mobile UI tropes. (I backed Canonical’s Edge fundraiser out of a desire to see more competition in the mobile space, but I don’t expect either Ubuntu mobile or Firefox OS to succeed, brutally.)

The fact that the Replicant project exists to provide a fully free Android distribution tells at least part of the story of Android’s pseudo-openness. Android is not free software by the Free Software Foundation definition, to the extent you decide that matters to you. Android is the mobile OS to which copyfighter Cory Doctorow lent the dubious distinction of failing well, and it must be described with couched phrases like “relative openness”.

There’s no question that Android is, as the FSF puts it, “considerably less bad than Apple or Windows smartphones”. Still, if you’re making an ethical commitment to free software, Android will not help you meet that commitment fully. I appreciate that you can buy Android devices with legitimately unlockable bootloaders, but that’s still not Freedom Zero. Rooting an Android device and jailbreaking an iOS device are basically the same act: warranty-voiding, dependent on third-party software that may come with security risks, totally unsupported and disdained by manufacturers.

That Android remains middlingly open, unwelcoming to those who haven’t bought into the Google ecosystem, and still fairly abrasive to use despite its advances is a shame. I was hoping to thoroughly enjoy Android this time around because I’m excited about Fairphone, a mobile device built with social justice in mind that will run Android by default. Perhaps a more open mobile OS will emerge as a better partner for Fairphone and other forward-thinking device manufacturers, hopefully one that surpasses Android in reliability and usability.

The State of Linux on Laptops

Macs became the machine of choice for developers around the same time that open source stopped being controversial and started becoming an essential part of practically every technology-enabled business. Personally, I switched from Linux back to the Mac when I found out that OS X was built on an open source foundation. When you think “software developer” today you wouldn’t be off-base to picture a person sitting in front of a MacBook sporting a GitHub sticker. But there is a kind of cognitive dissonance to this: open source software being used and produced on hardware made by a notoriously secretive company with a mixed and complicated open source track record, running on an operating system that is increasingly locked-down.

Being an open source advocate who uses Apple products engenders the same ethical unease I felt as a vegetarian before going fully vegan: committing only partway because, dammit, I wanted cheese on my veggie burger. Windows is a non-starter for me for any number of reasons, and so Linux is the only alternative I investigated.

In brief: trying to run Linux on a nice laptop is still pretty dire in 2013. For context, I’m not just talking about getting the OS booting, but having everything from function keys to power management working smoothly on a light, powerful machine with ample battery life.

The longstanding answer to the quandary of Linux on a laptop is “get a ThinkPad”. After a read-through of the comment thread on this crowing post on Lenovo’s blog about a redesigned ThinkPad model, you might reconsider that advice. Whatever goodwill the ThinkPad brand retained Lenovo is rapidly squandering when not apparently installing back-doors for the Chinese government. The only truly desirable notebook Lenovo manufactures today, the X1 Carbon, has a lousy screen, takes no more than 8 GB of RAM, and won’t ship without some version of Windows on it. (While ThinkPads are thought of as Linux-friendly laptops, don’t forget that purchasing a ThinkPad is voting by dollar for Microsoft and pre-installed bloatware; your decision to put Linux on the thing goes unnoticed by the powers that be.) While I initially liked the X1 Carbon’s predecessor several years ago, my affection for that model died quickly during real world day-to-day usage. I remain skeptical of Lenovo-era ThinkPads, and, having cut my teeth on an old IBM-era 500 series brick, a touch bitter about the once-great brand’s decline.

Dell now sells an ultrabook aimed at developers, the XPS 13, which runs a pre-installed version of Ubuntu. Its hardware is, like the X1 Carbon, presently due for a Haswell refresh and only takes up to 8GB of RAM (I have VMs, many VMs). The forums for this machine aren’t exactly filled with happy campers. And while the XPS 13 may ship with open source software, the roadmap for the hardware is far from transparent. Dude, I sincerely question you getting a Dell.

As best I can tell, the only decently-specified, reasonably light laptop you can buy with Linux preloaded today is the Galago UltraPro from longtime Linux-friendly PC hardware vendor System76. Dig around a bit and you’ll see that this portable is a rebranded Clevo W840SU-T. Clevo’s press release claims that the unit “feels good as you look”. I’m glad the laptop feels good, because I feel pretty dismayed looking at pictures of the thing. It somehow manages to be the chunkiest, clunkiest ultra-light laptop I’ve ever seen. Reviews are scarce as units are just now shipping, but hopefully it performs better than it looks.

With enough time, you can get Linux running on anything; that’s kind of the point. But at the end of the day, my problem with Linux on laptops has less to do with Linux than the perpetually sorry state of non-Apple laptops. I don’t mind spending an afternoon tweaking config files and recompiling the kernel, but you can’t recompile crappy hardware. I’d love to see, for starters, a single PC portable vendor who’s put half as much thought into the design of their power adapters as Apple puts into theirs. The reason so many programmers have switched to Macs over the past decade isn’t just OS X and nice third-party Mac software; Apple remains the laptop manufacturer to beat in an era where desktop computers have all but vanished in most development shops.

The State of Linux on the Desktop

I’ve not paid particularly close attention to the desktop Linux world over the last several years, but I was shocked to find just how fractured it is today. Gone are the days of distributions you could count on ten fingers. Linux distributions have now branched out into spins, slight remixes that add a few packages here, remove a few there, and change some default settings around. You might today run a spin of a distribution that is itself downstream from Ubuntu, which is in turn based on Debian. More than that, at some point in the recent past Ubuntu became the enemy, dashing the primary hope for any unifying direction in the desktop Linux world.

Desktop Linux today makes Android’s fragmentation look like a mere broken teacup; the GNOME vs KDE war of yesteryear seems like an old-timey family feud by comparison. The GNOME community has sub-subdivided itself over the move away from a traditional desktop environment in GNOME 3, resulting in an even more bewildering set of choices for desktop Linux users. For example, the increasingly popular Mint distribution alone has spawned both the MATE and Cinnamon projects.

It’s hard to know where to start with this dismaying and backwards duplication of effort, but such is the prerogative of those who spend their time contributing to those projects. For the rest of us, it is never the year of Linux on the desktop. Beyond maintaining a commitment to free software, the benefit of running Linux remains oddball tools like tiling window managers (though happily OS X now has a handful of closed and open source ways to get tiling behavior). Trying to compute like a normal with Linux is, after all these years, still an exercise in masochism.


It looks like I’ll be heading into 2014 still with Apple kit in hand and still uneasy about it. For my personal uses, nothing has emerged that warrants leaving the Apple ecosystem, but I continue to hope that will change for the sake of more competition, openness and user freedom, and to encourage more responsible corporate behavior on Apple’s part. For that reason I’ve backed projects like Fairphone and Ubuntu Edge despite my skepticism, and I’ll be rooting (no pun intended) for them from the sidelines over the next few months.

Aug 12, 2013

Letter To A Young Programmer Considering A Startup

I regularly get emails from young people, usually those with an interest in programming, who are trying to make decisions about school and/or their professional futures. This post is for those young people.

If you’re in your late teens or early twenties, you’ve grown up in a world that has come to idealize startups, their founders, and the people who go to work at them.

If you’re in school, maybe you’ve felt pressure or been incentivized to drop out and join or start a company. If you’re already out in the working world, perhaps you feel that your non-startup job is in some way inadequate, or that you’re missing out on valuable experience and potential wealth.

The generation you’ve grown up in has, for the past few years, teetered on the brink of being “lost”. Jobs are scarce, and going to university offers no assurance of landing one. Big, old corporations are no longer guaranteed safe havens in which to build a career. Startups seem, through the lens of the media, like the only sign of life in an otherwise dying landscape. I understand their appeal.

Everyone’s path is different, and your choices are your own. That said, you aren’t making your choices in a vacuum. Here are some things to consider that, in my experience, you’re less likely to hear about working in startups.

A startup is just a means to an end.

I recently interviewed a young man. I asked him where he wants to be in four years. “Running my own company,” he said without hesitation. I asked why. “Because entrepreneurship is in my blood,” he replied. There was no mention of what his hypothetical company would do, what problem it would solve for people. His goal was business for the sake of business. That’s what he had gone to school for, after all.

People are fulfilled by their work when they operate with a sense of purpose. So much of our understanding of the psychology of success is around setting goals and keeping those goals at top of mind: visualizing the moment of accomplishment, tracking our progress towards it, having others hold us accountable to reaching it. Goals give shape to our individual futures.

Maybe a startup is the best way to meet a goal, and maybe it isn’t. If the goal of the young man described above is to run a business – any business! – then perhaps a startup is indeed his best path forward. For others, though, I often wonder if they’re fitting their goals into the format of a startup because it’s an approach that’s lauded, admired, and easily understood (if not easily accomplished).

Maybe the best way to meet your goal is starting a non-profit or going into politics. Maybe it’s doing research at a university or making art in a squat. Maybe the answer is joining a large, stable company with formidable resources that you can leverage to meet your goal. Maybe your goal is best met by building a stable yet undemanding career that leaves plenty of time for family, friends, community, and self improvement.

A startup is just a means to an end. Consider the end, and don’t seek to revel in the means. What do you care about? Who do you want to help? Does a startup make meeting your goals easier or harder? Where will it leave you when your goal is met? Where will it leave you if it isn’t?

A startup job is the new office job. Startup culture is the new corporate culture.

Startups are portrayed as an exciting, risky, even subversive alternative to traditional corporate work. Startups are thought of as more free, more open and flexible. Some companies surely begin that way, but a few interviews at later-stage startups will make clear just how quickly they ossify into structures that look very much like the organizations that came before them.

As there was in the first dot com bubble, there is a current proliferation of startups, incubators, accelerators, angel/seed funding, and so forth. In order for the “startup community” to replicate itself, nanobot-like, the mechanics of “doing a startup” have been reduced to an easily transmitted sequence of actions accompanied by a shared set of values, norms, and language. As a consequence, the culture of most startups is blandly uniform, right down to a style of dress and grooming that helps “startup guys” – and all too often are they guys – stay with their herd (lest they be picked off by cougars).

Business school graduates like the young man I interviewed are going directly from college to startups, if they even finish school at all. Business majors, traditionally risk-averse, now say they don’t want to work for big companies. But startups are the new big company. They are, as I’ll describe below, the field offices of a large distributed workforce assembled by venture capitalists and their associate institutions.

There’s nothing inherently wrong with an office job. Just realize what you’re signing up for. When the company-provided keg runs dry, the free lunches are making you fat, and playing the Xbox in the break room is no longer as fun as it used to be, what then? When you find that you now report to a politicking middle manager and not the inspiring CEO who interviewed you, will you still want to be there? Is a supposedly novel working environment enough to sustain you? When everywhere you might consider working looks more or less the same, is the novelty even there?

Startups have been systematized, mythologized, culturally and socially de-risked; reduced down to formulas and recipes. Yet, there is no enduring formula for creativity and rebellion. When we attempt to factory farm innovation we breed out the very thing we’re trying raise: the creative destruction that stokes and re-stokes the fire of capitalism.

Startups are part of the system, not a rebellious wrench in the cogs.

The funding for startups – that is, the money that pays your prospective salary – comes from somewhere. Wealthy individuals and institutions invest in startups as just another asset class. The futurist Bruce Sterling recently quipped that “start-ups are full of [young] people working hard to make other people rich – Baby Boomer financiers mainly”. While that might be an overly general and cynical take it’s by no means untrue.

In broad strokes and excluding areas like biotech, venture-backed startups are a machine into which relatively small amounts of capital are inserted in one side and, ideally, quite a lot more comes out the other. (In actuality, this machine doesn’t seem to work anymore, though the effectiveness of VC as an asset class and VCs themselves is certainly up for debate). The salient point, though: what’s in the middle of the machine is you. You make it go.

The machine doesn’t care about you. In fact, the machine is designed with the understanding that most startups will fail, or at most offer unremarkable returns to investors. The majority of the companies in many VC portfolios are acknowledged duds. One or two “10x” companies prop up most portfolios. At best, startup founders who fail get another pull of the slot machine. At worst, their failures drive them to desperation.

There is nothing inherently disruptive about a venture-backed startup. The startup system is just another system; an alternative to the corporate ladder with just as many rungs to climb. Some startups may end up dramatically reshaping a market, but then so might an incumbent player or an active regulator.

The now-perennial celebration of startup-driven disruption raises the question: if we accept that disruption is even happening, are we better off in the resulting disrupted market? Have we solved a problem, or have we shifted the problem elsewhere? Have we created value while furthering justice and equality, thus yielding enduringly positive change? Or have we merely made one group of wealthy people slightly more rich at the expense of another group of wealthy people? Are we creating a better future or just scrambling up the present?

Startups have an ongoing interpersonal cost.

No story of a startup is complete without a scene or two of macho heroics: nights spent programming to exhaustion, weeks away from home trying to raise money in pitch after humiliating pitch. Startups appeal to a desire for daring that’s lost in many forms of modern work, and we’re told stories of the rewards waiting when personal lives are sacrificed on the altar of the launch schedule.

Less frequently do we hear about the damage that startups do to people’s lives. In extreme cases, as with the entrepreneur whose story of failure and suicide was linked to above, the “community” might take a day or two to reflect and mourn in blogs and tweets. Then it’s back to “grinding it out”, and more importantly, making a public show of just how hard you’re working to appease investors and intimidate competitors.

I’ve seen firsthand the damage that startups can do to relationships. I’ve watched marriages and friendships fall apart, seen children and partners pushed aside, and failed those in my life in all kinds of ways when work came to the fore. I’ve listened as people who are the very picture of startup success – visible in the press and social media, headlining conferences, forever founding and exiting – have confided their utter loneliness despite being seemingly at the social center of the entrepreneurial community.

When you’re young, relationships seem like a renewable resource. Friendships are plentiful and come easily. Just out of the house and out in the world, you’re eager to escape the heretofore-constant presence of family. Being pulled into work makes you feel important, independent, and adult. Work itself can provide a new community and new friendships, and the bonds formed during intense collaborative work are strong.

I’ve made such friends through work at early stage companies. Ironically, those relationships are easier to maintain and enjoy when I’m not working at a startup.

Parting thoughts.

I’ve worked in startups on and off for over half my life now. That work has brought me some financial freedom, and I’ve put money I’ve made back into other startups. If there is, as I argue above, a modern “startup system”, I am a part of it.

I won’t equivocate: I am deeply skeptical of this system. I’m skeptical of this system’s slavering, self-congratulatory fetishization of “disruption” while so obviously becoming the sort of stolid institution it seeks to displace. I’m skeptical of the startup community’s often short-term outlook. I’m particularly skeptical of its callous disregard for both the lives of the people who participate in it and the lives of those who live in the world that startups seek to reshape. Let’s not even begin to discuss how commonplace collusion, price fixing, and other market-corrupting activities are in the world of VC. The point being: it’s a bad game and a rigged one.

And yet. There are startups I wouldn’t want to see disappear. There are people working at and funding those startups who are good, kind, balanced in their personal and professional lives, thoughtful of the impact of their work. Just as we might cast aspersions and accusations of corruption on other systems like politics, mass media entertainment, and professional sports, we must admire those who operate ethically and efficiently within them. We should further celebrate those who are pioneering new and alternative systems, for they work in the shadow of a community that has a constant hand on the crank of the hype machine.

Now, you could say that I’m laying too much responsibility at the feet of the startup world. Though this system daily broadcasts itself as the savior of everything from capitalism to culture, surely we can accept that business is business and ideals are best left at the door. As a VC at a top-tier Sand Hill Road firm told me during a pitch several years ago when describing a conceptual feature in Simple that would let users easily and regularly donate a portion of their savings to charity, “let’s not waste time on that stuff; we’re here to make money”.

You could take this tack, but I hope that your idealism hasn’t been worn down at such a relatively young age. I hope you want your work to be imbued with meaning, purpose, and value no matter what form that work takes. More than that, I hope you want your life to be defined by more than work.

Young programmer, I urge you to consider both sides of the startup coin. There are so many ways to make a dent in the world.

A note on feedback.

If you’re part of the intended audience of this post, I’d love to hear your feedback and answer your questions, preferably over email. My address is easy to find on this site.

If you’re not part of the intended audience and are very very mad that a stranger on the Internet has a different opinion than you, I encourage you to direct your energy into an alternative argument that a young person (or, really, any person at a point of career transition) might benefit from reading. They are your future employees, coworkers, or founders. It’s them you need to convince, not me.

May 23, 2013

Alone Together, Again

The following was written in August, 2012. It was published a month ago in the first issue of Marco Arment’s iOS-only publication The Magazine. Marco has generously allowed his contributors to retain copyright and the option to share their work on their own sites after a time. If you have an iOS device, please consider supporting Marco and The Magazine by purchasing a subscription.

· · ·

I am in a stranger’s apartment in Reykjavik, and for the first time in almost five years, I am truly alone.

Two months ago my life was as per David Byrne’s enthusiastically confused yelps: beautiful house, beautiful wife, not one but two large automobiles. I had a job that seemed like the job I should have at a company I was proud of. I lived in a city that I had carefully chosen to live in, a city that I thought was going to be my home for some time.

Nobody’s life ever really falls apart, exactly. Lives unravel, thread by thread. First, I came to realize that the job wasn’t the right job. Then the city wasn’t the right city. Two threads loose, easily stitched back in; there are other jobs, other cities. Our house went on the market. I resigned.

Then, a month ago, the person I thought I was going to spend the rest of my life with came home from a neighborhood-scouting trip to a place we were intent on moving back to. “We need to talk”. Never good. “I can’t do this anymore. We’re just too different”. The seam, ripped.

That was Saturday evening. There was no going back and no way forward. By Tuesday afternoon we’re in a lawyer’s office, drawing up a settlement. The court moves quickly when there’s no children and no disagreement over who gets what. The divorce should be final by the time this is published. I will probably hear about it by email, wherever I happen to be. I will look at my iPhone, wince, hit “Archive”, close my eyes, and breathe.

The next four weeks disappeared like a long weekend spent sick. I went to the other side of the country while she moved out. Family and friends did their best to hold me together as the stages of grief washed over me in no particular order. The last listed stage of grief in the literature is Acceptance. It didn’t take long to accept that this is all for the best. A gift, wrapped in barbed wire. I just wish I had seen it being wrapped.

Teeth gritted, I went back to the city that was no longer our city, back to the house that was no longer our house. I packed up what was left, put all but necessities into storage. Sold my car. I could have stayed, but I couldn’t stay. The whole city was our life together, brief as it was. Coupled a little over four years total, just a bit over two of which was spent married. We moved mere weeks after the wedding, bought the house not long after. Friends have been engaged longer than our entire relationship lasted. It was something small that we foolishly made into something big, and it’s already receding into the distance. I’m filling my vision with fields of lava, mossy valleys steamed by hot springs. Trying not to look back.

With my life in that place done, I got on a plane, and then another plane, and now I’m alone in an apartment in Reykjavik. Now, this is my life. Not the apartment or the city or travel, but the laptop I’m typing on. We are alone together, again.

· · ·

I owe my life to technology.

I first realized it in my early twenties. Everything important around me at the time, I’d found on Craigslist: my girlfriend, my job, my apartment. It was a powerful realization: I could sit down with my laptop and, in a matter of hours or days, change my world in both superficial and fundamental ways.

That was years ago. Technology specializes over time. The life I just finished packing up wasn’t courtesy of Craigslist. It wouldn’t be, now. The modern web has six sites for everything, branded and polished and localized and full of options. House from Redfin. Cars negotiated online before ever walking into a dealership. Wife from OkCupid. Wedding invitations by email. Date-night dinners booked on OpenTable. Fast and friction-free.

I spent four years telling anyone who asked how we met that OkCupid’s matching algorithms must have been off. “We were only a seventysomething percent match, with like a twelve percent chance of being enemies. Guess they need to work some bugs out!” The joke’s on me, of course. I emailed the right person at OkCupid to apologize for the years of disparagement.

I could blame technology. Maybe stitching together a durable life takes physical work, needle callouses. Maybe technology made it all too easy to slide into a life I wasn’t meant to have. It would be so convenient to think that way. Marriage didn’t work out? Blame the dating site. Bad experience at a restaurant? Blame Yelp.

Technology is just people, though. People like me. We get it wrong. And even when we get it right, people are people: they ignore the algorithms and recommendation engines and scores and weightings. People do what makes sense to them, then and there. What else are we to do? All the specialization, all the options, and we still have to choose. We still have to make our way in the world, alone, save for our technology built from other people’s frozen choices.

· · ·

I will owe the next part of my life to technology, but I will owe it more to experience.

I tried to imagine what my life would be like in the wake of all this if I had been living two hundred years ago. Most likely, I would be trapped. I would be living in the scraps of the life that had unraveled around me. I could not seek the support of friends from around the world at any time of day or night. I could not book passage to wherever I felt I needed to escape to. I couldn’t work from wherever I happen to end up. Trapped.

I am grateful that I live in this time. For all the loose threads in my life, I don’t feel trapped. Technology allows me to make choices that can shape and reshape my world. I don’t yet know what I will do, where I will live, or who I will love. For each of those decisions, though, there are tools, and the tools present options.

The trick, of course, is having the experience to inform the selection of the right options. For that, we have no technological substitute. You simply have to live, work, love, explore, fail at all of those things, and learn.

From Reykjavik to Berlin. Then on to New York City, maybe for a month, maybe for a lifetime. Airbnb, Hipmunk, TripIt. Messages in my inbox suggesting new ventures, new possibilities. Choices. Threads to be sewn together, making something whole again.

· · ·

Postscript, November 2012. A stranger’s apartment in Brooklyn.

I thought long and hard before submitting the above to Marco. Divorce is a subject that, despite its sad prevalence, remains taboo. Divorce is generally discussed behind closed doors, on long phone calls, or via whispers in crowded restaurants. I do not regret my decision to be public about my experience, though. I received many responses, often from people who are going or had gone through something similar. Those people found comfort in knowing that they were not alone, and that is justification enough.

My parents divorced just as I was on the cusp of adolescence. There was nothing in the world that I wanted less than to experience that again, much less firsthand. Some months on, though, I stand by my statement that this was a kind of gift. I do not live with shame, for I have nothing to be ashamed of; I was true and honest, and that was not enough. I do not live in misery. My life today is not at all what I imagined it would be, but it is wonderful and strange and exciting.

It is taking time to make things whole again, as it should. I’m in no rush. I spent so much time trying to organize the life that I thought I wanted. It wasn’t the same as living.

Nov 11, 2012