Menu

Sanspoint.

Essays on Technology and Culture

Why Technology Companies Don’t Understand People

There’s a joke in technology circles about how programmers don’t understand how non-programmers use computers. Daring Fireball used to have a “UI of the Week” feature that linked to UI atrocities that only a programmer could love. It’s true that not every piece of software needs to be as sexily designed as a piece of Apple hardware. There’s nothing wrong with a utility looking like one. It’s just one small symptom of a larger problem in computing as more and more ordinary people embrace technology.

Joel Marsh claims that Google and Microsoft “don’t understand people.” This is an understatement. [1] Most technology companies don’t understand people. Often, it’s that their focus isn’t on the person who actually uses the software every day. Episode 39 and episode 40 of Accidental Tech Podcast go on deep dives into why so much Enterprise software is awful. In short, they’re selling on features to people who don’t have to use it. There’s no incentive make the user interface better, because it won’t move more units. Apple doesn’t get a free pass here, either. By all accounts, their back end for app developers and content creators to get stuff in people’s hands is downright awful. There’s also no incentive to make it better, because it’s clearly not keeping people from putting apps on the store and music on iTunes.

If only this problem were limited to enterprise software and tools for programmers. Apps that add new features because they looks good on a press release, companies getting into “social” because that’s the buzzword of the week [2], trendy redesigns that impede usability, and forcibly integrating unpopular new products into popular old ones, all of these are symptoms of not understanding people. Even worse, it’s thinking of people as eyeballs to monetize or wallets to pry open. Thinking about this problem, I come back to Tab Closed; Didn’t Read. The pattern of obscuring content with subscription boxes and social media buttons is exploiting a specific sort of knowledge about people. It’s a lazy technique that makes product guys think they’re doing something with a measurable benefit while frustrating people. Worse, it’s not a big leap to go from newsletter subscription boxes to popups that pretend to be system dialogs reporting fake system errors. Behaviors like this are common enough that they have a name: Dark Patterns.

Fundamentally, people approach technology from a task-oriented mindset. They sit down at their computer, or take out their smartphone because they want to do something: share their thoughts with their friends, buy a pair of socks, or fling cartoon birds at cartoon pigs. It’s the job of the technology to let them to do that thing they want to do with the least amount of fuss. It’s why iOS is still built around an incredibly simple grid of icons. If you want to share your thoughts with friends or fling cartoon birds around, you just touch. Apple builds its experience around reducing friction. To do such a thing, however, requires a willingness to understand the real human motivations and real human frustrations that come when trying to accomplish a task with technology.

The underlying reason for all of this? Most technology companies haven’t had to live in the consumer space until recently. It wasn’t until the Internet took off in the mid–90s that personal computers took off in the home among ordinary people. By this point, most of the companies in the space had fossilized around a business and design model that focused on business users and the odd hobbyist who wanted to learn how to use a computer for fun. (I was the second type.) It’s the enterprise software problem writ large, and companies are scrambling to learn how normal people think and use computers. Most of them aren’t doing a very good job of it.


  1. Marsh does make a lot of great points in his piece, though I think his criticism of the original gMail interface is a little off the mark. It may not have been pretty, but it was usable as all hell.  ↩

  2. Google+, Ping, and Microsoft’s so.cl all come to mind.  ↩

Some Thoughts on Entrepreneurship, Startups, and Venture Capital

A note, before I begin: I have only a year of experience in the world of startups, and I am unsure if my experience is typical. Some probing of others suggest that it is, if not typical, at least not unique. My experience shades some of my thoughts. However, the particular startup I worked for allowed me to see some parts of how the sausage is made, in terms of venture capital and funding. A lot of what I saw, I did not like, but this may be from my particular experience.


I wonder if we have our priorities a little screwed up. When I think of the word “entrepreneur,” I think of someone who is trying to build something and shepherd it through the long term. It’s bringing something into the world you want, scratching your own itch, but other people’s itches as well. If you’re not scratching their itch, you’re not going to last long as an entrepreneur, after all. You don’t enter into it lightly. If you bring on employees, you accept responsibility for them, and they for you. When this happens, you’re not just building something for yourself and your customers, you’re building something for your employees and their families too.

However, when I look at the startup world, I don’t see a lot of that. I see a lot of people who just want to make lots of money, and a few people who want to scratch an itch. And as more people make lots of money in this game, even more people with lust for money are getting into the game with silly, frivolous ideas that tap into exactly what will get them large amounts of funding from people who also want to make lots of money. That second group are venture capitalists.

There’s nothing inherently wrong with venture capital, and there’s nothing inherently wrong with building something frivolous. So many wonderful things have been created in the spirit of frivolity, and many of the tools I use every single day have been born because someone else invested money early on. When applied right, venture capital is a great resource to help someone with a great idea get it off the ground and moving under its own power. When applied wrong, it gives us speculation, a bubble of inflated company valuations like $4 billion for Snapchat before they’ve made a single dollar—even if they have a monetization strategy now.

One part of this comes from the sheer shadiness of—again, some—venture capitalists. Another part comes from the inflated value of “entrepreneurs”. Most ventures are going to fail for some reason or another. I wonder how many venture-backed companies like Everpix fail because the VCs were too hot and bothered by “the next Facebook,” or some college drop-out in a nice suit with a dumb idea that will get a lot of users, even if it can’t make sustainable money. The more “entrepreneurs” who make it big and get the huge payout, the more people will desperately follow in their footsteps, waving their business plan and/or prototype app at the VCs in the hopes of free money.

But that money isn’t free, and I don’t mean in the sense of giving up equity in exchange. The money used to fund startup companies comes from somewhere, and it’s typically not some lucky winner’s largesse. Venture capital funds raise money from government and private pension funds, college endowments, non-profit foundations, and institutions that manage the sovereign wealth of entire nations. They invest because they hope to make enough back to pay retired workers, pay professors, build schools and infrastructure, and more. Considering the risks involved in venture capital, should there not be greater stewardship of that money? Is a smaller, steadier return not better for the people whose money is truly at stake, rather than finding “the next Facebook”? And this doesn’t even factor in the venture funding for things like clean energy solutions, new medical treatments, and other things that will only pay off in the long term, if at all. It’s too risky for investors whose only thought is how to get the company to a profitable exit, and fast.

This may be why I don’t invest in anything. That, and the lack of money to do so.

There are VCs out there who do want to help a company succeed, and will work with the companies they’ve invested in to put them on a solid footing. They share their experience with similar companies they’ve worked for, founded, or invested in, identifying the pitfalls and showing a clear path—if the founder will listen. There are also VCs out there who don’t care what the company does, how, or why, as long as they get back their investment and make a tidy profit on top. One of these is more valuable than the other, but I see the influence of the latter type more often when I look at technology and startup news. That’s something I try not to do as often these days, but sometimes it’s inescapable.

Building things, building businesses, these are not bad things. Investing in a promising entrepreneur with a captivating idea is not a bad thing, either. I’m not trying to tar all entrepreneurs and all venture capitalists with the same brush. It worries me to see businesses starting up and employing people with the assumption that the venture capital gravy train will keep flowing, or they will be acquired before the bill comes due and they need to make money. It worries me, because it shows a distinct lack of both long-term thinking and an unwillingness to consider the very real risks involved. In the tech world, having a failed startup or two under your belt is a taken as a good thing, and I will not deny anyone who tried a business and failed the right to claim it as such. I worry about the employees—the people who have x years experience on their résumé at a company that no longer exists and won’t take phone calls for references. The people who are trying to raise a family or pay off student loan debt on ramen noodle salaries and the promise of a payout. Can’t we do better by them, and by the investors?

Either way, this is the last I have to say about the whole thing for a while.

Snapchat and Ethical Safeguards

In all the mystery around Snapchat’s insane valuations and dismissal of a $3 billion buyout by Facebook, there’s claims that Snapchat is being used by Wall Street for insider trading. Even if this isn’t the case, it’s the responsibility of Snapchat to ensure that it’s service is used in an ethical manner. This may be too much to ask from a company that made its bones by giving people a way to share temporary pictures of their naughty bits.

Hardware, software, and services all have different levels of control they have over how they can be used. Apple’s iTunes EULA has a clause requiring that it not be used to make nuclear weapons. If Kim Jong Un uses iTunes on his Mac, there’s precious little Apple can do about it. When was the last time you heard of anyone taken to court over an EULA? Once a piece of hardware or software is in the user’s hands, most bets are off.

It’s online services that have the most ability to influence what they’re used for. Many online services do enforce their terms of service, to a degree. Child porn is guaranteed to get services to act, for obvious reasons. Google and Microsoft both have created a program to block child porn from their search results. On Facebook, nudity is often a ticket to account suspension. Yet, of these same services are notoriously slow to act to shut down users who sexually harass and threaten users, behavior which is also against their terms of service.

Why? It’s easier to algorithmically identify porn than it is to identify hate speech and harassment. In Snapchat’s case, having people scan through the 350 million-plus photos on Snapchat per day for questionable or illegal content requires more manpower than is feasible. (That’s nearly a quarter million photos per minute.) Complicating matters further is that adding oversight from the start would have hampered Snapchat’s growth.

All of the the tools we create can be used for good or evil. Yet, as long as we are in the position to influence how our tools are used, it is a ethical requirement that we use that influence to make everyone’s lives better, not just line our pockets. Companies that acknowledge the potential use of their products for evil, who can act to prevent it, and do not, are committing evil by proxy. I am certain that safeguards can be put into place to, if not prevent unethical behavior on the part of users, at least mitigate its consequences. These have to be ingrained in the very fabric of the service, from the start, and it requires thought far beyond what most people put in to their apps. Perhaps we’ll see it in time.

Coin: One Card, Many Risks

There's a new product that's been making the rounds called Coin that promises to reduce the number of credit and debit cards you need to carry around to just one. It has a great video by Sandwich Video, and I was almost swayed. There were just two things standing in my way. One is the price—even the $55 (with shipping) pre-order price is a tad too rich for me right now. It is perfectly reasonable, however, for the product. The second issue is that I don't use enough cards to make it worthwhile: a debit card, and occasional credit card. Both of them fit in my minimalist wallet with room to spare.

However, after a conversation with Patrick Rhone on App.Net, I've lost all interest in the Coin project. Patrick raised a very good question:

Is it just me who looks at this and immediately thinks, “Great, just what we need. One company to get hacked for all of my card numbers and data.”?

If, as implied in the FAQ, Coin stores all their card data on a server, even encrypted, a hack attempt could pull every card a user owns and the contents of the magnetic strip, making it trivial to clone the card. 1 Even worse, as Patrick asks, “What if Coin is served with a FISA order to provide all of your card and purchase data to a government agency?” If a hacker pulls a pile of encrypted data without the encryption code, there's still a challenge to pull real data out of the mess. If there's a government order to get the data, Coin could be under the onus to decrypt it for them. Naturally, the FAQ doesn't cover these issues.

Ben Brooks disagrees, saying that Coin doesn't seem “more risky than storing, or using, a credit card with any other company on the web.” It's true, Coin has some great security features, including automatically deactivating if it's away from your phone for too long by using Bluetooth 4.0. I'm not sure what the range of that is, but if you don't store your wallet near your phone at home, you may have to re-activate your Coin before going out. There's also some sort of safeguard to prevent adding cards you don't own, but details are scant on how that aspect works.

In the App.Net conversation around Ben's piece, user @evs notes that Coin “would remove any safety for the seller to prevent fraudulent chargebacks.”, and that “many of the newer card readers have mechanisms to reject duplicated/cloned cards, which Coin is essentially doing.” Elsewhere, @gross points out the method Coin uses to switch cards may keep it from PCI-DSS ceritifcation. All of these add up to a lot more risk than many ordinary people should be taking with their financial data.

There's some awesome technology inside of Coin. From an industrial engineering standpoint, it's a pretty impressive first generation product. It also solves a problem that is real for enough people that Coin should be able to turn their business into an ongoing concern—if they can overcome the very real risks and technical implementation issues. If Coin doesn't provide some more details on implementation: if they store card data on a server, in what form, the strength of the encryption, and if they'll fight FISA requests, the risks outweigh the benefits by a large margin.


  1. Fundamentally, the technology behind Coin is similar to a card skimmer and recorder in one. When you set Coin to use the data from your debit card, it simply records the magnetic strip data onto its own strip. If they can do it, a malicious actor can too. 

Enough Of “It’s Like ___, but for ____!”

The startup elevator pitch of “It’s like ___, but for ___!” has become such a cliché that it has its own generator site, capable of churning out stuff like “It’s like SkillShare, but for SAT tutors,” or “It’s like ShoeDazzle meets SeatGeek.” That doesn’t stop people. If you’re looney enough to look at AngelList, you’ll see that same basic formula repeated in any number of startup company descriptions. Why? Because it’s easy. Taking the business model of one successful startup company, and applying it to a similar, perhaps more niche space, and rolling out a functional beta is a safe and easy way for the VCs to pick up your scent.

Admittedly, coming up with a truly new product is a hard thing to do. A lot of real innovation comes in the space of the “adjacent possible”, that is combining disparate things in new and exciting ways. It doesn’t always work, but when it does, watch out. That doesn’t seem like what a lot of startup companies are doing, at least not the ones getting huge piles of money for bringing in lots of people. How many “temporary” image sharing services do teenagers need to share naked pictures on, or social networks that gamify content consumption? How many industries can be “disrupted” before the unemployed and redundant start rioting in the streets?

In my past job, I was inundated by talk about what flavor of the month company was raising so much from whomever—partially because I was working for a startup company in the “___, but for ___” vein that was soliciting funding, and partially because our second blank consisted of people who manage the money to invest in venture capital funds, and the venture capital funds themselves. It grew tiresome, especially with so many startups doing exceedingly boring stuff with the intention of just bringing in as many warm bodies and eyeballs as possible to increase their valuations. No wonder some people think we’re experiencing a second technology bubble.

All of this makes the “Silicon Valley can do no wrong” rhetoric sound even more arrogant. If the modus operandi of Silicon Valley were less about eyeballs, advertising, valuations and exits, and more about solving real problems that affect real people, claims like “it’s becoming excruciatingly, obviously clear to everyone else that where value is created is no longer in New York; it’s no longer in Washington; it’s no longer in L.A.; it’s in San Francisco and the Bay Area.” would come off far less obnoxious than they do. Only in the venture capital world would something as scummy as payday lending get $14 million dollars. That same money could go to helping people improve their lives and finances to save them from even needing usurious loans to make it through the week.

The problem is that approach takes a long time, and doesn’t have the same prestige for the founder and profit for the VC firm. There are very real problems facing people around the world that are simply beyond the ability of web and mobile apps to solve: global warming, income inequality, disease, famine, and war. Technology can be a part of those solutions—just look at the work Gates Foundation has done for improving the cold chain required for vaccines. Even worse, with philanthropy on the decline, nonprofits and other organizations that work to improve people’s lives are forced to find new revenue sources. These sources often end up being returns from their investments, which are increasingly including venture capital funds.

If the endgame of serial entrepreneurs was to make a few billion in the startup and/or VC game, and then turn around and use their largess to improve the world along the lines of Andrew Carnegie, it might not be so frustrating. However, the situation as it stands is not sustainable. The numbers don’t add up, and either people will figure that out, or the bubble will burst. The end result will, optimistically, result in new companies focusing on building sustainable businesses to last. More likely, it’ll just be like the intervening years between the first and dot-com bubble and now. I think we can expect history to repeat.