To walk through San Francisco is to interrogate the lurid, sometimes brutal history of California’s settlement in the mid-nineteenth century. Each street has a story. Guerrero Street is named for Francisco Guerrero, a landowner and politician killed by a slingshot-wielding horseback assassin in 1851. Charles H. Gough, a local milkman, served on the committee that named many of the streets in 1855; in a bit of minor civic corruption, he named a major thoroughfare after himself and other streets after his sister, Octavia, and a friend, Steiner.
Noah Veltman, a San Francisco-based coder and designer, wanted to create an application to exhume this history. He envisioned a scrollable, zoomable map to surface the stories behind each street name. And because each tale is so intimately tied to geography, he wanted explorers to be able to access his map on-the-go. These days, says Veltman, “designing anything of substance involves thinking about mobile” — which means grappling with new constraints and problems.
Modern newsrooms have the same challenge, caught as they are between two powerful trends: the exploding volume of digital information, and the rapid shift to mobile computing.
Veltman had to figure out how to ensure even fat fingers could “click” tiny streets
The storage company EMC estimates that we created 2,800 exabytes of data in 2012 (to put that in perspective, one exabyte is roughly equivalent to a billion gigabytes, and can store 36,000 years worth of HD video). Ben Fry, the designer behind the Processing language, likes to say that visualization is one of the best ways to cope with this data overload because “our eyes are the highest bandwidth channel for getting information into our brains.”
And in the context of news, more and more eyeballs are directed at mobile devices. Nearly half of American adults own a smartphone and 31% have a tablet, according to Pew Research Center. More than a third of those people check the news daily on their devices; NPR reported that fully half its traffic on election night last year came from mobile users. This shift in reader behavior is mirrored by a shift in business imperatives, with mobile ad revenues up 80 percent in 2012, to $2.6 billion, while the overall digital ad market grew 17 percent, according to Pew.
Veltman is currently working at the BBC as a Knight-Mozilla Fellow, a program that embeds hackers in newsrooms around the world. He found that creating clickable streets on a dense map interface was a major challenge. “It was already borderline unreasonable to expect people to successfully click on them with a mouse,” he says. “It was impossible to expect it with a fingertip.”
What I ended up doing is listening for mouse clicks anywhere on the map that isn’t clickable, and then doing a bunch of math to figure out the closest clickable point, and then, if the distance to that point was less than a certain threshold, highlight that object. So basically it estimates in a very convoluted way what street you meant to click.
Didn’t quite get that? Don’t worry. Veltman, who’s been designing websites since the Geocities era and is a veteran of several startups, is in the 1% of newsroom programmers. And when it comes to visualizations for mobile devices, most organizations still need to grapple with the basics.
“I think most news organizations are getting ahead of themselves when it comes to mobile dataviz,” says David Yanofsky, a designer and coder in the Quartz newsroom. While the digital cognoscenti fawn over complex, cutting-edge projects, “there still isn’t a good archetype” for the simple stuff, he says. “I have yet to see a well-designed interactive line chart made for mobile. Once the simple stuff gets figured out, the more complex stuff will have a better foundation to build off of.”
Amanda Cox, a vaunted interactive designer at The New York Times, says designing for multiple screens — even when the designs are simple — is an enormous challenge. “Simple adapting tends to lead to stuff that’s mediocre in at least one space,” she says. “Good designs exploit what’s unique about the environment they live in.” Interactive newsrooms need to update their style manuals, and decide on rules for when and where mobile-specific actions, like sliding and shaking, are appropriate, and templates that ensure that desktop buttons and links don’t shrink to unclickable specks on mobile screens.
Mobile designers must also become as integral a part of the newsroom process as desktop designers have become, helping editors and reporters figure out the best — and most realistic — treatment for their stories. At the same time, they must acknowledge that not every news story lends itself to an infographic, and not every inforgraphic will work on a smaller screen. Quartz tries to make every graphic mobile-friendly, but “sometimes we decide that the specific thing we’re making is inherently not mobile-friendly,” says Yanofsky. Mobile devices are, after all, still more limited in terms of processing power. And while they’ll get faster, there will always be a new form factor (Google Glass, anyone?) that introduces new limitations.
Once they figure out the basics, newsrooms can start looking for clever ways around those limitations, just as Veltman did when he came up with an algorithmic way to guess a user’s intention. Still, the emphasis must remain on the story and the information, not on programming tricks.
“Designers need to embrace their lack of control in a device-diverse world,” says Veltman. “Yes, painting when you don’t know the size of the canvas is hard, but when you worry less about the paint and more about what the painting is trying to say, it starts to make sense.”
Finance is a bit like a secret society in that it likes to obscure commonsense ideas with intimidating language. Loans become bonds, bond insurance becomes credit default swaps. It's a way to separate insiders and outsiders and raise a protective moat around in-the-know practitioners.
Anyone who reads TechCrunch has heard of the term “convertible note,” and knows it's a common way for early-stage investors to bet on startups. But it's a hard-to-grasp term, even for someone like me with an economics degree and a year of an MBA under my belt. I recently learned exactly what it does and why it's used so frequently, and wanted to share that knowledge in a no-bullshit way. It's not super complicated, but if you're a 22-year-old Y Combinator grad building your first company, and investors start making offers, don't you already have enough on your plate without having to parse financial gibberish?
A convertible note is debt. It's a loan. The details differ, but usually when someone writes you a convertible note for $100,000, you're expected to pay it back, along with some interest, in 1-2 years.
But of course, no one really wants that to happen. That's because of the “convertible” part of the note. The investor is hoping that instead of getting paid back, your company will become the next Dropbox or Airbnb, and at some point you'll raise a real round of venture capital. At that point, the note will become equity, and instead of having the right to get paid back, the investor will have an ownership stake in your company.
Why do a convertible note instead of equity? In short, it's simpler, cheaper, and less time-intensive than an actual equity investment. For one, an investor and an entrepreneur don't have to negotiate the value of the company if they're using a convertible note - they can let the valuation be set during the first equity round. This is particularly useful for really young companies with one or two people and little more than an idea.
Also, if an investor decides to buy 10% of your equity outright, you may need to become an LLC or a Delaware C Corp. There are costs and tax obligations that go along with that. In general, the costs associated with a note can be 1/10th or less that of equity financing ($500 versus $5000, say). Also, if you've taken an equity investment and then go bust a year later, it's difficult (legally) to disentangle all the ownership stakes. If someone loans you a convertible note and you go bust, an investor can simply write off the investment.
Of course, as with all simple ideas, people have figured out ways to make them far more complex. As a founder, there are a couple key sticking points you need to know about:
The cap. Notes often have a cap, which means, “This is the maximum valuation that my investment will convert at.” Let's say an investor gives you $100,000 through a convertible note with a $1 million cap. That investor now owns a minimum of 10% of your company. If you raise venture capital at a $10 million valuation, your convertible note holder still gets 10%, i.e. $1 million worth of equity. Of course, if you raise money at a $500,000 valuation, then your note holder gets $100,000 / $500,000 = 20%. In other words, higher caps (or better yet, no cap) are better for entrepreneurs.
The discount. Another common element of a convertible note is a discount. This is kind of like a floating-rate cap. It basically means that, whatever the value of your company when you take your first equity investment, I get to invest as if it's happening at a lower valuation. So if a $100,000 note has a 25% discount, and you raise money at a $1 million valuation, your note holder gets $100,000 / ($1 million * 0.75 = $750,000) = 13.3% of your company (rather than 10%). Sometimes a note will have both a cap and a discount, and give the note holder the right to convert at the lower of the two valuations. In general, an entrepreneur prefers less of a discount (or no discount).
Auto-conversion. You received an investment in the form of a convertible note. A couple years go by as you toil to build your company. The note comes due, and you still haven't raised a round of equity financing. What now? Most often, the investor will simply extend the note. Or, if it looks like you're heading toward bankruptcy, the investor might write-off the note and consider it a loss. There's an interesting third case, though. Maybe your company is doing fairly well, but you don't need to raise more money. In this case the investor can choose to convert the note into equity… but at what valuation? Hopefully you can agree on one, but if you can't, the investor holds a trump card: He or she can demand that you repay the note (remember that it's still technically a loan!). If you don't have the cash, you go bankrupt – even if the company is otherwise doing well! It's far better to have some kind of auto-conversion option so that, if after a certain period of time you still haven't raised additional money, the note auto-converts at a pre-specified valuation. Of course, this requires talking about valuation when the note is written, which eliminates some of the advantages of a convertible note.
A year and a half ago I sat down with Evernote CEO Phil Libin for a wide-ranging chat. At the time, I was smitten with memory-decay algorithms, basically mathematical methods for learning new facts and concepts as efficiently as possible, and so of course I brought it up.
Phil didn't have any immediate plans to include such a feature in Evernote. But he did have a really interesting response to the idea (which I'm paraphrasing because I can't find my notes):
The hard part isn't periodically reminding people of something they're in the process of learning right now. It's what happens in 5, or 10, or 20 years, when people have decades of memories and information stored in Evernote. It'll be overwhelming. How do we smartly filter that information to remind people of what they already know when they need to know it?
It's taken me a while but I've finally gotten hooked on Evernote, and one of my favorite features is a really modest, easily overlooked part of the browser plug-in. If you opt into the “Related Results” feature under the toolbar's options, then when you run a Google search you'll see something like this:
This is genius. Every time my mind latches onto a topic (at least when expressed in the form of a Google query), Evernote subtly reminds me what I already know about that idea. I've been surprised about how often I re-search topics I've already spent time exploring; I think most people will also be shocked by the redundancies in their learning processes. The “related results” box is also an unobtrusive way to reinforce ideas you've recently committed to memory.
From Dropbox to Drive to Instapaper and beyond, there's no shortage of tools for outsourcing your memory. But no company is thinking as deeply and as creatively about how to access those memories, even (and especially) after they've spent years moldering away in your mind.
My first thought on reading Evgeny Morozov's dense, brilliant, and ultimately unfair takedown of Tim O'Reilly was: When did O'Reilly run over Morozov's dog? Morozov's Baffler piece is the academic equivalent of a flaming bag of shit on the tech publisher's doorstep, a pie-in-the-face as O'Reilly strolls down the red carpet.
Plenty of others have summarized Morozov's novella-length (over 16,100 words!) piece; i09's Annalee Newitz does a decent job:
Morozov is worried that the memes of Silicon Valley will reshape our government's future in a way that sounds democratic and progressive on paper – but will turn out, in practice, to create a nation whose citizens are impoverished and disempowered. Government will abdicate responsibility for providing its citizens with basics like roads, schools, scientific research, and health care. Instead, it will create an “open platform” that allows private industries to plug their private schools into the government system…
More importantly, Morozov believes this future will fragment our citizenry, eroding group solidarity and turning us into little monads who can't organize a protest or social movement…
It's a dystopian vision of the open future, and one that's worth paying attention to.
I have two problems with Morozov's argument.
The first, and relatively minor, critique of Morozov is that he's an asshole. Most people would agree that O'Reilly is a pro-market technologist with a knack for marketing himself and his company; to Morozov he is a “Randian” who “manipulates” through “propaganda.” Sorry, Morozov. Alan Greenspan is a Randian. The Nazis were propagandists. O'Reilly is neither. I'm not going to cry for a publishing magnate, and I'm sure O'Reilly can handle a few knocks on the chin. But it's a spineless move to turn down an offer to meet face-to-face with O'Reilly before publishing a hit piece, as Morozov did, arguing that “I don’t believe in interviewing spin doctors: the interviewer learns nothing new while the interviewee gets an extraordinary opportunity to spin the story even before it’s published.”
More substantively, I was struck time and again by Morozov's implication that technologists like O'Reilly, by foisting their open-source ethos on government, are despoiling some extant democratic process that yields better results. The thrust of Morozov's argument is that “government as a platform” and “open government” will create a passive citizenry. We'll be willing to make 311 calls to fix potholes, sure, just as we click the “Report Spam” button in Gmail. But we won't protest or write to our Senators. We'll tune out the news and become as disenfranchised and dissociated from the political process as we are from the secret-sauce algorithms that make Google work.
As a result, once-lively debates about the content and meaning of specific reforms and institutions are replaced by governments calling on their citizens to help find spelling mistakes in patent applications or use their phones to report potholes.
I'm sorry, but which “once-lively debates” is Morozov referring to here? The ones on Fox News and MSNBC? Or the camera-friendly “debates” on C-SPAN given to an audience of none? Or perhaps the Super-PAC-financed commercials played over and over in the handful of battleground states that determine our president while the rest of the country acts as little more than a gusher of campaign cash?
O'Reilly and “open government” aren't endangering our democracy. That honor goes to money, cognitive capture, revolving door politics, gerrymandering, income inequality, media partisanship, and any number of other factors far more insidious than the guy who publishes geeky how-to manuals with animal sketches on their covers.
I'm particularly biased against Morozov's argument at the moment because I just finished listening to This American Life's episode on disability benefits. If you haven't heard it yet, go listen - it's far more fascinating than the topic would suggest. The gist is that the number of disabled people claiming benefits in the U.S. has skyrocketed over the last few decades. And it's not really because more people are disabled. It's because people with poor education and no decent job prospects in the information economy have found a loophole that pays them a meager, taxpayer-provided salary as other types of benefits disappear. Moreover, after the Welfare Reform Act of 1996, state governments have a financial incentive to move welfare recipients off the dole. The idea is that beneficiaries get jobs instead of welfare, but many states are shunting them onto the disability rolls, which are paid for by the federal government.
Morozov thinks that politics may look ugly, but it's a more or less fair way to negotiate between competing visions of how our society should work and how to morally tackle problems like inequality or privacy. But when Morozov writes that “openness as a happenstance of market conditions is a very different beast from openness as a guaranteed product of laws,” I cringe. Laws have unintended consequences because smart people find ways around them, and the laws and the people who create them don't adapt nearly as quickly (if at all). When Congress reduced welfare benefits, states (and the lawyers and corporations that enable them) found ways to twist the disability program into something it wasn't intended to be. Similarly, when financial regulators required certain institutions to hold only high-quality assets, Wall Street found a way to turn subprime mortgages into AAA-rated debt. We all know how that turned out.
Morozov is an eloquent and much-needed critic of techno-centric thinking, and has done more than anyone else to remind us that innovations can create dystopias. He should remind himself, though, that the current world isn't exactly utopian.