Most industries are dominated by monopolies. How we enforce antitrust law explains far more than you might think.Photo courtesy of BP Miller.
My first monopoly was AT&T.
I lived on a commune until I was eight. We didn’t have toilets, but we did have phones. We didn’t own them. It was a commune, after all. But they were in our house and we got to use them.
When we reentered “normal” civilization, we still didn’t own our phones. AT&T did. This was 1984, the same year Congress broke them up. I was more confused than injured by their power. Capitalism was new to me. Every single thing in our house was ours, for the first time, except that one. We had to lease it from Ma Bell. Even weirder, the lines in our house were apparently not ours. (I mean. We were renters. But you get the idea.) We had to pay to attach other objects to ports in our own house.
This confounded me. “Some… outside company I’ve never heard of makes rules about what we have in our house?” Yes indeed.
Thankfully, it didn’t last. With five siblings, we needed but could not have paid for those extra phones.
My second monopoly was Microsoft.
They had complete dominance of desktop operating systems and software (the Office suite, plus Outlook/Exchange for email). I went to Reed College, so I exited school as a Mac user, in the middle of their dark days. In hopes of avoiding Windows I tried everything else: BeOS, Linux, Solaris, you name it. No matter how fast I ran, I was often stuck on Windows at work because, well, everyone was.
Microsoft abused its monopoly heavily and freely until being taken to court. Microsoft’s abusive behavior is usually discussed in terms of its effect on the web. But I’ll never forgive them for Outlook. It taught multiple generations of people to do email incorrectly. To this day, the average business user is incapable of having sophisticated discussions over email because Outlook trained them not to.
Ironically, Microsoft itself likely only exists because of Congressional antitrust action against IBM. The government eventually withdrew its case against Big Blue, but not before convincing it of the importance of leaving room for others.
The Paradox of Antitrust Choice
Kids coming up today are lucky. They have so many monopolies to choose from.
Of course, I don’t actually mean “choose”. You pretty much have to use all of them. Google for search, Facebook for social, Amazon for e-commerce and cloud infrastructure, and Apple for hardware and apps worth paying for.
Tech is absolutely rife with monopolies. (And monopolists.) But the industry itself is largely in denial about that. “We’re different!”
The last month has highlighted this. Congress has dragged the richest, most powerful tech founders and CEOs in to testify. More importantly, a Judiciary subcommittee has produced a huge report on concentration in the tech industry.
I’m going to focus on that last link, from Ben Thompson. He makes a throwaway comment:
consumer harm, which is the de facto standard for antitrust in the United States
The article itself is interesting and informative, as most of Ben’s writing is. But this small line shows that Ben is in a box that limits how he thinks about antitrust. And if he can’t see out, few others are likely to.
I think he should. I think you should. I think everyone should.
Abuse of monopolies affects all of us. It’s not just about tech. We’ve allowed most of our industries to become highly concentrated: Agriculture , pharma, internet access, and many more. Heck, even eyeglasses.
America doesn’t have a tech monopoly problem. We have a plain old monopoly problem.
Ben works hard to explain that the tech monopolies are natural because of what he calls Aggregation Theory. He implies this makes their monopolies more acceptable, even inevitable. He accepts there is abuse, but a very narrow definition of it. Even if his theory is sound (which I am not convinced of), it doesn’t explain the rest of the monopolies that plague us.
Something else does.
The “consumer welfare” standard is not the law
Ben is right that US antitrust law focuses on consumer welfare. That’s pretty much the work of one person: Robert Bork. His book, The Antitrust Paradox, successfully rewrote the history of American antitrust enforcement. Gone were concerns about competitive markets, or any discussions of the downsides of market power. Nope. If prices are low, it’s good. That’s it.
He didn’t get any new laws passed. He just convinced our country to enforce them differently.
Yes, consumer welfare is an important input in the laws themselves. But there’s far more to it, including a healthy focus on market power. Yet Bork managed to gut everything else with one book. (To be fair, there were a lot of rich and powerful people set who became even more so once he won.)
To be clear: The laws themselves have not changed. Only how we enforce them, within the government and the courts.
It is impossible to understand antitrust enforcement in our country without accepting this fact: We have strong antitrust laws and are choosing not to enforce them. They have been gutted by an extreme interpretation, and fifty years later, nearly every industry demonstrates the ruinous consequences.
Revisiting Consumer Welfare
Bork successfully reframed the downsides of market power, with a lot of help from the Chicago School of Law. But there have always been people fighting back.
Lena Khan produced the seminal work in this category, Amazon’s Antitrust Paradox. She lays bare how powerful Amazon is, and how useless consumer welfare is as a means of assessing monopoly abuse. Its impact has allowed her to carry the flag even further.
In particular, she was part of the team that ran that Judiciary subcommittee hearing, and produced the related report.
Yes, her argument - and thus at least partly, the argument made by Congress - is that Amazon and its peers have too much power, and they are abusing it to gain even more.
But more importantly, she’s arguing that you cannot have a conversation about market power without also talking about standards other than consumer welfare.
That’s what Ben Thompson (and Ben Evans) and all the other tech commentators need to understand.
The argument is not really whether one of these companies is a monopoly. It’s what standard we should use to assess their behavior.
Do we let Bork decide, and use a light hand and generally tolerate heavy concentration of power?
Or should we follow the original intent of the laws, focusing more on encouraging a competitive landscape and a market free from companies that are too big and too powerful?
The Tech Monopoly Minefield
Every tech founder I know builds their business around the reality of these monopolies. If you’re in e-commerce, your business is defined by the space Amazon leaves you. You don’t necessarily have to be on Amazon, but prepare to be attacked if you’re not. If you’re in social, you have to ensure Facebook doesn’t want your business. If you make apps, you can only make or sell them the way Apple lets you.
I expect most founders and investors don’t even realize how much we’ve given up on doing because of these monopolies (and all the smaller industry heavyweights, like Salesforce). We talk big about agile startups outwitting the big players, but… that only works if they can’t choke off your suppliers, outbid you for engineers, or take hundreds of millions in losses to destroy your company.
What could we build if we didn’t have to fear so many big players?
Conclusion
I’m still haunted by that AT&T phone we didn’t own.
I could not be happier that the government is finally revisiting our antitrust standards. And honestly, I’d rather they make mistakes in regulating the huge players than not regulate them all. We’ve seen what five decades of almost no action results in.
Like everyone, I love fast cheap shipping. But it’s not worth destroying independent retailers over. Honestly, I can’t stand using any of Facebook’s products, but maybe I could if they were stand-alone instead of part of a soulless corporation bent on domination.
I believe in the free market. But none of the markets I’m interested in are. They’re all dominated by players so large, so powerful, that our only choice is to work with or around them.
It’s long past time to get rid of the consumer welfare standard, and bring back to true antitrust enforcement.
Privacy expectations are changing. How will companies change with them?Photo courtesy of Tobias Tullius
Change is coming to how tech companies handle privacy. Everyone is going to have to adjust, but new startups are caught in the middle: Be as useful as the companies built in the old world, while following the new rules.
Today’s dominant tech companies don’t care much about privacy. Many of their businesses couldn’t exist if people were careful with their data. Facebook only survives if people are willing to share widely and publicly. Google’s ad engines feed on reams of public data.
Privacy will matter far more to new companies. Google has taught companies the cost of sharing their data publicly. Consumers are slowly waking up to how pernicious Facebook’s data practices are. And the laws themselves are changing.
Regulation is already happening at the state level, and internationally. You might not want federal legislation, but state by state rules would strangle growth of new startups.
I know some say government can only create problems, not fix them. I am not so cynical. The creation of the EPA is a great example of government taking industry in hand and making the world better. I am eager for Congress to take privacy as seriously.
The Business of Privacy
But I’m not a legislator. I’m a builder. I’m more interested in understanding how people’s behavior will change, and what that means for the products I’m creating.
For some, the future of privacy is already here. DuckDuckGo is thriving (despite its silly name) on promises of providing great search without all the tracking. The Brave browser is growing for similar reasons.
But how big is this change? Will the average person in the next decade expect to retain privacy, demand companies respect their data? (I originally wrote “computer user” here instead of “person.” With the smartphone, there is no difference.)
Or will privacy concerns continue to be like security concerns have been for the past decade: the domain of the few, the nerds?
This starts as a moral question. Privacy is a fundamental right. We deserve applications whose business model requires it, rather than neglects it.
But it’s also a business question. What kinds of companies thrive in the current privacy framework? Will they thrive in ten years? What about a world with little privacy? Which companies might do better if people cared more about it?
It’s worth elaborating on what I mean by privacy. Google and Facebook have very different definitions, for example. Facebook’s business is built on promising as little privacy as possible, and delivering even less. They share your data with pretty much everyone. Google just uses your data internally. They don’t share your browsing history; they just use it to market ads.
There are far more companies out there like Google than Facebook. Everyone shouting “data is the new oil” is advocating for Google’s business model: Collect a ton of data and profit off of it. It might start as your customers’ data, but if you collect enough it, and tie it all together, it becomes your data.
By policy, these companies (usually) care more about privacy than Facebook does. They rarely sell or share your data. This is better. But privacy isn’t restricting data to only a few trillion-dollar companies. It’s sharing my data with people, not companies.
It’s instructive to look at one company offering less privacy today than in the past: Microsoft. In the old days, all of my documents sat on my computers. My email ran through servers run by corporate. Microsoft could never have gotten to any of them.
Now it’s all “on the cloud.” What does that mean? Microsoft has it. They might not be sharing it with others, but they’re certainly looking at it. Oh, maybe individuals aren’t. But their programs are.
This can be good. Usage data can help vendors improve their software.
But mostly, it’s bad. These promises of better software tend to be hollow. I don’t want better ads. I don’t want your algorithm picking what I see. And I certainly don’t want machine-learning recommendations based on a statistically average user.
People are beginning to see the downsides of handing all of their data to companies. They know that Facebook, Google, Microsoft, Apple, and Amazon have too much power. They are changing their privacy expectations. Not just the nerds, but average people.
But how much? How fast?
The Cloud Conundrum
Privacy in the modern era is a special quandary. The cloud is pretty great. No synchronization. No management. Easy sharing.
No one wants to give that up. Yet today, cloud usually brings severe privacy compromises.
Do I try to build without the cloud, enabling more privacy, and try to compete with what might be less functionality? Or do I build on the tools everyone else uses, where a lack of privacy means there’s little limit to what I do?
Is there a world where you get all of the benefits of centralization, of the cloud, of being online, but don’t have to sacrifice your privacy? Can you be in the cloud, but keep your own data instead of letting a company put it all into one bucket?
I think so. For many cases, I don’t even think it will be that hard. It will just require thinking differently. It will require new answers, maybe slightly harder ones. But not whole new forms of math or science. Something attainable and reasonable today.
As a founder and investor, there still might be big downsides. It might mean you can’t be the next Google. The next Facebook. Or even the next Salesforce.
It might be that a company is worth less if it does not exploit your data.
What if ethical, privacy-conscious companies stay small, and unethical privacy-destroying companies get to keep growing? There is precedent. Prior to the creation of the EPA, an industrial plant would be committing fiscal suicide to spend money reducing pollution.
I worry about this. I’d sure love to see better behaved companies get rewarded with growth. But that’s certainly not the world right now.
Of course, this is partially why we need new regulation. The rules need to change. There was a time when big business just dumped all of its waste in the local rivers. It was cheap. Why should they care if it killed people and ecosystems? Gotta protect shareholder value! But then the rules changed. Nixon (!) created the EPA, and now we take it for granted that industrial players are forced to protect the air and water at least a bit.
The rules will matter less if enough people change. If you stop buying from companies who abuse your data, they’ll stop doing it. If the next Facebook can’t be built off of your data, then someone will need to find a new way - and hopefully a better one! - to meet your needs.
But maybe those businesses won’t be quite as big. Or get there quite as fast.
Are you ok with that? Is that a reasonable trade off?
It is for me. Facebook didn’t make me a billionaire. I’m not at risk of some other data-centric company making me rich. I’m not investing in companies that collect and exploit your data.
But a lot of people are. A lot of our industry is built on the idea that access to this data is good. Many companies could work without it, but choose not to.
Take the smart home, for example. My smart thermostat is in my house with me, right next to my phone. On the same network. But how does my phone configure it? Not by talking directly! No. My phone contacts cloud services, which then contact my thermostat. Why? Partially because it’s easier. But mostly it’s about data.
There’s no chance Google would have bought Nest for $3.2B if that data weren’t available.
Maybe Nest would be a better company if it were more concerned with making better devices instead of extracting our data. But I don’t think Google would be as excited about that other company. Investors like the multiples that all that data gives them. And product people like what the data allows.
Like industrial effluent, this data is toxic. Dangerous. I’m afraid of what’s being done with what leaks out. I’m afraid of all of the bias. I’m afraid of businesses built on my lack of privacy, my lack of boundaries.
My Bet on Privacy
My new company assumes people will care more about privacy than they have. I expect I’m giving up some long-term potential by doing so. There are things we can’t do as a result. Things that our competitors might find easy to do.
But we’ll be able to make promises no one else can. And we’ll find new ways - hopefully better ones - to solve our customers’ most important problems.
Even writing this frightens me a bit.
I’d love to believe that promising privacy would make my company more valuable, make it easier to raise money. I know it will make it easier to hire people.
Some users will choose us specifically because of our privacy model. But how many? And will it be enough?
Automation is not to blame for all the job destruction and wage stagnation. But you can still do great harm if you build it for the wrong reasons.
We’re told that automation is destroying jobs, that technology is replacing people, making them dumber, less capable. These are lies, with just enough truth to confuse us. You can have my robot washing machines when you pry them from my cold, wet hands.
I’m not some Pollyanna, thinking tech is only ever positive. Its potential for abuse and hurt is visible across the centuries, and especially so today. But I’m more optimistic about the upside than I am pessimistic about the down, and I’m uninterested in scaremongering screeds against it.
And yet. Technology and automation are not forces of nature. They’re made by people. By you. And the choices you make help to determine just how much good or bad they do. Even with the best of intentions, you might be doing great harm. And if you don’t have good intentions at all, or you don’t think ethics are part of your job, then you are probably downright dangerous.
I’m here to convince you that you have a role in deciding the future impact of the technology you build, and to provide you - especially you founders, tool builders, automators - some tactical advice on how to have the best impact, and avoid the dark timeline.
As I was building Puppet, explaining that I was developing automation for operations teams, execs and sales people would think they got it: “Oh, right, so you can fire SysAdmins!”
Ah. No.
When prospective customers asked for this, I offered them a choice: You can keep the same service quality and cut costs, or you can keep the same cost, and increase service quality. For sysadmins, that meant shipping better software, more often.
Their response? “Wait, that’s an option?!” They only knew how to think about their jobs in terms of cost. I had to teach them to think about quality. This is what the whole DevOps movement is about, and the years of DevOps reports Puppet has published: Helping people understand what quality means, so they can stop focusing on cost.
And those few people who said they still wanted to reduce cost, not increase quality? I didn’t sell to them.
Not because they were wrong. There were real pressures on them to reduce costs, but I was only interested in helping people who wanted to make things better, not cheaper. My mission was completely at odds with their needs, so I was unwilling to build a product to help them fire their people.
This might have been stupid. There are good reasons why a CEO might naturally build what these people want. The hardest thing in the world to find for a new product is a motivated prospective customer who has spending authority, and here they are, asking for help. The signal is really clear:
You do a bunch of user interviews, they all tell the same story of needing to reduce cost, and in every case, budgets are shrinking and the major cost is labor. Great, I’ll build some automation, and it will increase productivity by X%, thus enabling a downsizing. The customer is happy, I get rich, and, ah, well, if you get fired you probably deserved it for not investing enough in your career. (I heard this last bit from a founder recently. Yay.)
This reasoning is common, but that does not make it right. (Or ethical.) And you’ll probably fail because of your bad decisions.
Let’s start with the fact that you have not done any user interviews. None.
The only users in this story are the ones you’re trying to fire. Executives aren’t users. Managers aren’t users. It seems like you should listen to them, because they have a lot of opinions, and they’re the ones writing checks, but nope.
This has a couple of consequences. First, you don’t understand the problem if you only talk to buyers, because they only see it at a distance. You have to talk to people on the ground who are doing the work. Be careful when talking to them, though, because you might start to empathize with them, which makes it harder to help fire them.
Even if you do manage to understand the problem, your product will still likely fail. As much as buyers center themselves in the story of adopting new technology, they’re largely irrelevant. Only the people at the front line really matter. I mean, it’s in the word: Users use the software. Someone, somewhere, has to say: Yes, I will use this thing you’ve built, every day, to do my job.
If you’ve only talked to buyers, you have built a buyer-centric product, rather than a user-centric one. Sure, maybe you got lucky and were able to build something pretty good while only talking to managers and disrespecting the workers so much that you think they’re worthless. But I doubt it. You’ll experience the classic enterprise problem of closing a deal but getting no adoption, and thus not getting that crucial renewal. Given that you usually don’t actually make money from a customer until the second or third year of the relationship… not so great.
Users aren’t stupid. Yes, I know we like to act like they are. But they aren’t. If your value promise is, “Adopt my software and 10% of your team is going to get fired,” people know. And they won’t use it, unless they really don’t have a choice. Some of that is selfish - no one wants to help team members get fired, and even if they’re safe today, they know they’re on the block for the next round of cuts. But it’s just as likely to be pragmatic. You’re so focused on downsizing the team that you never stopped to ask what they need. Why would someone adopt something that didn’t solve their problems?
What’s that you say? You ignored their problems because you were focused on the boss’s needs? This is why no one uses your software. Your disrespect resulted in a crappy product.
Call me a communist, but I think most people are skilled at their jobs. I am confident that I can find a learned skill in even the “low skill” labor. I absolutely know I can in most areas people are building software.
I was talking to a friend in a data science group in a software company recently, and he was noting how hard it was to sell their software. He said every prospective buyer had two experts in the basement who they could never seem to get past. So I asked him, are you trying to help those experts, or replace them?
He said, well, our software is so great, they aren’t really necessary any more.
There’s your problem. You’re promising to fire the only two people in the whole company who understand what you do. So I challenged him: What would your product, your company look like if you saw your job as making them do better work faster, rather than eliminating the need for them?
It’s a big shift. But it’s an important one. In his case, I think it’s necessary to reduce the friction in his sales process, and even more importantly, to keep those experts in house and making their employers smarter, rather than moving them on and losing years of experience and knowledge.
The stakes can get much bigger than downsizing. In his new book, Ruined By Design, Mike Monteiro has made it clear that designers and developers make ethical choices every day. Just because Uber’s and Instacart’s business model requires that they mistreat and underpay workers doesn’t mean you need to help them. While I don’t think technology is at fault for most job losses, there absolutely are people out there who see the opportunity to make money by destroying industries.
This is not fundamentally different than the strip mining that happened to corporations in the 1980s, except back then they were making money by removing profit margin in companies and now they’re making money by removing “profit” margin in people’s lives. Jeff Bezos of Amazon has famously said your margin is his opportunity, and his warehouse workers’ experiences makes clear that he thinks that’s as true of his employees as it is of his suppliers and competitors.
Just because they’re going to get rich ruining people’s lives doesn’t mean you have to help.
I think your job matters. I think software can and should have a hugely positive impact on the world; not that one project can by itself make the world better, but that every person could have their life improved by the right product or service.
But that will only happen if we truthfully, honestly try to help our users.
When, instead, we focus too much on margin, on disruption, on buyers, on business problems…. we become the problem.
The limitations of mobile devices perfectly complement the strength of the cloud, as foretold by Sun Microsystems two decades ago: Your computers will be weak and hold no data, and the servers will be powerful and store everything. They were just wrong about what form those weak computers took (and, of course, who would be selling the servers).
I obviously love the benefits of mobility, of having an amazing computer in my pocket and having access to the world’s information pretty much wherever I am. And there are many capabilities we take for granted that you just could not provide without large central collections of data that the cloud enables.
But many of the changes in our tech landscape are accidental outcomes of cloud + smartphone. I regret them. And I want to fix them.
One of those big changes is the demise of the document.
You might think, no, I still have documents. I mean, yeah, I used to have Microsoft Word documents, but now I have Google Documents. Right?
No. The content you have in Google Docs is stored in a big database. Sometimes, when they choose to, you can treat it like a collection of documents. But it’s not.
This is pretty obvious when you try to use Google Drive. Compare using documents there to a Dropbox folder full of Word (or Pages1) documents. One comfortably exists in a world of folders, hard drives, and file systems, and the other just feels…. not quite right. That’s because Google Drive is wearing the camouflage of a filesystem, but it’s a database in the back end, and the truth leaks through. We’re not fooled that easily.
It starts with a miserable user experience, but doesn’t end there. Because Google is storing all of your data centrally, you need their permission to use it. This is new.
Until the smartphone and cloud took off, Microsoft had a comprehensive monopoly in digital documents, in text, spreadsheets, and presentations.2 To participate in business, you pretty much had to own Office. Their position was so strong they built a Mac version just to prop that platform up enough for it to look like a viable competitor. The market just didn’t see an OS as competitive without office.
But lo and behold, times change, and now you want all of your files online. Google wants to help you do it, and just happens to have a couple of fancy features you couldn’t (at the time) get without uploading everything. Real-time collaborative editing is actually pretty sweet.
Microsoft worked for years to prevent other apps from reading their documents, but they seem to have stopped that at some point. I don’t know if they just gave up the arms race, realized they had already won so it didn’t matter, or actually felt the need to reduce their market power. But by the time Google acquired Writely and rebranded it as Google Docs, it wasn’t that hard to read these docs separately. This was a massive boost for Google (and theoretically smaller companies, but it didn’t turn out that way).
After all, all the docs you care about were right there, on your computer. You didn’t need to ask Microsoft for a copy; you did not have to export them, wondering what data was included and what was kept back. And the form you’d send to Google is the exact form you’d send to anyone else, via email or on a USB drive. Their ingesting of all of your critical data was pretty easy as a result.
But in 2019, things are very different. Want all of your data from Google Docs in the next new company’s fancy web app? Step 1: Export. That’s right. You have to ask Google to give your data. Because, and I hate to belabor this, you don’t have it.
Then your fancy app needs the ability to import the special arbitrary 100% proprietary format Google exports in. It’s true that some apps might allow you to skip this step: They’ll authenticate directly to Google and slurp your data down. But just like when Facebook shut down data access for Twitter and other competitors after building its own network by copying data from Friendster and others, Google will only tolerate this kind of integration when they don’t feel threatened.
You need their permission, their tolerance. Given their use of monopoly power to weaken Yelp, among many others, you can be sure they’ll have no qualms about quashing a budding competitor by making this hard if someone gets close.
So here we have two analogous situations, with almost identical data, but in one case you have your data, and in the other, you’ve got to ask permission for it. There are downsides to each, but there’s no argument they’re different.
Note that this isn’t really a question of data “ownership”. Google would probably argue that you do actually own your data, as might Facebook. You just can’t access it in a useful way.
I’m thrilled that the cryptocurrency/blockchain communities are driving a conversation around data ownership, but it’s still disappointingly naive. This concept runs up hard against the reality that digital copies are free, and it’s basically impossible to prevent people from copying data you’ve given them read access to. Conversely, “ownership” means nothing if I can’t get all - and I mean all - of my data in a useful form.
What they need to talk about instead is rights. Realistically, I can’t own my birthday. Would that be a copyright? Trademark? Patent? Of course not. It’s just a fact, and facts can’t be property. But we all know that my birthdate matters.3 I need the ability to prevent you from, say, publishing it widely, or using it in combination with other facts to impersonate me. These are legal rights, not aspects of ownership.
I miss the rights that documents gave us, now that we no longer have them. Because these rights were implicit, a consequence of the technology reality at the time, we did not even know we were giving them up. But we’ve got to fight now to get them back.
The first thing you can do is be conscious of this when you choose your tools. All life is a compromise, and sometimes it’s the right answer to give up rights for functionality. But many apps are functionally equivalent, yet make vastly different choices about your rights.
As one example, I recently migrated away from Evernote, because their business model is shifting to a focus on businesses, which, well, I am not. It was a nightmare. Even though everything in my Evernote notebooks was either a text file or a PDF, I couldn’t export literally a single thing as text or PDF. Well, that’s not true. I could export each individual item that way. But not the whole collection. My choices were HTML or a proprietary format. It took hours of manual work, and a lot of it I just dumped in a folder, never to look at again unless disaster strikes, because it wasn’t worth it.
Compare that to what I’m replacing it with: Keep It (as of today, anyway). I’m sure I’ll give up some features to pick it, but, ah, I haven’t found any yet. And all the files I put in it? They’re just - hold on to your seat, folks - files. I can open that directory on my Mac. I can add things to it. I can remove them. Then I can see them in Keep It. If I stopped using it tomorrow, I would have to, um, add the files to something else. Or use the Finder, or Dropbox, or something similar.
It’s obvious that Keep It respects the document, and they see their value as adding functionality on top of it, rather than subsuming it in some way.
This should be the gold standard. You should be able to adopt an app that gives you functionality, but does not take away rights.
In the age of documents, apps like Microsoft Word could try to curtail your rights, but other developers would be on your side trying to give them back. In the age of the cloud, and the smartphone, you don’t get that option. You no longer have rights, you have “permission”, with a side of binding arbitration.
I don’t think we can go back to the era of documents on a disk. But it’s worth looking back and asking: As we’ve gained so much, what have lost?
And then demanding that our software providers begin to give some of that back.
Although even Pages, and all of Apple’s productivity apps, weaken the definition of a document, because they use bundles instead of a single file. ↩
Yes, I know this photo is of the old model. But it perfectly captures what’s still wrong with the new one.
The iPad has been my primary mobile computing platform since a couple years after it came out. I’ve had every version since the very first, and I immediately replaced that one when a version with LTE arrived. I spent two months traveling with my family last summer and only used my iPad. I’ve taken countless trips with nothing but it and my phone to get work done.
I’m not mobile-only. I have a 5k iMac on my desk, and am far more capable and productive on it than I would be on anything else, because of screen size if nothing else. It’s worth noting that I’ve worked professionally on MacOS (Classic and X), Solaris, Linux (I tried nearly every distro available until around 2008, and even tried the BSDs), BeOS, and once in a while a little Windows. I had two 21" Trinitron monitors on my desk in 1999, and I’ve spent more hours than I could count fiddling with my computing experience to maximize productivity. Heck, that’s what ended up with my starting Puppet: I just wanted to get more done, faster. So when I say the iPad is the most productive device for me in many situations, I’m saying that within the context of twenty years pursuing exactly this.
I’m a heavy iPad user, and it’s really important to me. I use my phone, but I love my iPad.
That context is important for this review to make sense. We’ve seen many reviews of the new iPad that could be summarized as, “I’ve been using a Windows desktop for twenty years, and the iPad still can’t replace it for my use cases.” Those reviews are useless. I mean, unless you’re one of those people. Get a Kindle, I guess. This review is for people who are willing to shift work styles and recognize that different platforms optimize for different problems. Success for the iPad is more about whether it has valid and compelling uses rather than whether it works for each and every one.
The short version of this review is that I love the new iPad Pro, but I decided not to keep it. I already have two of the older versions at home. The difference between this and previous generations is not a big enough jump for me in the ways I use it, especially given I’m between jobs. For the things that were working great, they now work better, but more of the things that weren’t working, it doesn’t really make an impact.
Your scroll bar is telling you, though, that this is a much longer review. Settle in. (Or silently close the tab, and save half an hour of your life.)
How I fell in love with the iPad
I know some find that travel is explicitly where they struggle to survive without a laptop, but it’s where I flipped the fastest. The easiest explanation for why - also explaining the importance of LTE - is my pattern of travel when I was still running Puppet.
Here’s what it looks like if I have a laptop:
I show up at the airport. I find a seat, pull my laptop up, log in, and join the local wifi. Most of the time this doesn’t work, because airports, so I tether with my phone. Then I wait. No idea how long. I use Apple’s Mail, and the desktop version has consistently had some issues downloading mail efficiently, especially from Google. I’ve tried literally every other mail app; don’t @ me. So I wait. When boarding is called, or all the mail is obviously downloaded, I close my laptop. I have often found myself carrying an open laptop through the boarding line because it’s not done yet.
On the plane, once we’re at 10k feet, I process the mail. When I was running Puppet, I received about 230 mails a day, and sent about 30. Ideally a 1.5 hour flight between PDX and SFO (my most common trip) would at least get me to “no scroll bar in my inbox”, and sometimes even inbox zero(tm).
I land. If I am taking a taxi, I get in, open my laptop, tether to my phone, and let the mail start flowing out. Some of them make it. Some don’t. I’ll try to join every wifi network I spend more than five minutes around. If I’m not taking a taxi, no mail gets sent until I get to my hotel after dinner, most likely - I can’t do this while driving, and the trains are usually too far underground to get service.
I just spend the rest of the day dealing with inconsistencies in the inbox on my phone and the one on my laptop. 🤷♀️
Here’s what it looks like on my iPad:
Once I get on the plane, I open the mail app on my iPad to make sure it’s fully synchronized. I then put it in airplane mode, and start reading on it. At 10k feet, I lower the tray and start typing. I’m a little less efficient on an iPad than a laptop, so I get a little less email done, but it’s shockingly similar.
When we land, I turn airplane mode off. I open the mail app just to ensure it’s going to synchronize as quickly as possible.
I get annoyed texts from my team about the torrent of emails I’ve just unleashed.
That’s it.
You could argue that this says nothing about the iPad. Any device that was always on and had an LTE connection could do this, no problem. But of course, my other computers don’t and can’t have these features. I honestly don’t know why I can’t get an Apple laptop with an LTE chip in it, but I do know why it’s not running 100% of the time.
Once my primary travel computing use case - email - flipped, I found a way to make most other things do so.
There are many people whose primary use for computers is sitting in one place, working on one or two problems for hours at a time. I’d be surprised to find those people prefer an iPad. Even if I could program on one, I wouldn’t want to, because the screen just isn’t big enough to show everything, and I can’t have all the windows open that I need.
But as a CEO, my job was constant change, constant context shifts, constant movement. I craved depth, but usually in vain. The iPad fits that life perfectly.
That’s why I love it.
The iPad today
Everyone has said this 1000x times: The iPad’s hardware is great, it’s the operating system that’s lacking. I agree, but I have more to say than that. And it’s not just about features like reading files off a disk, which I doubt I would ever use.
Apple has to (ahem) think differently about the device altogether. They’ve gotten better: They’ve agreed it’s not just a big phone, it has different users, different use cases. It needs a different experience.
But they’ve barely begun to work through the consequences.
I love my iPad. I use it more than every other device put together. I have for years. It is great at so much.
But its user experience for absolutely mundane work is a shocking embarrassment.
I built an automation company to almost 500 people. Our software was built on the recognition that system administrators - the people who make your computers work for you - were spending too much time on menial tedious work, and it got in the way of their real work. Puppet helped restructure their entire work life, automating away the tedium and making space for the most important, most valuable work.
The iPad has provided me great new abilities, but forces me to take the long way to using all of them. If you were to watch me using it, you’d notice that a huge portion of my direct interactions with it are only necessary because of its failures, not my desires. Some of this is not a ton better on the Mac, which always focused more on simplistic usability than working hard for power users. Coming from a fully customized keyboard-driven experience in FVWM and its descendants, I was never going to be happy. I still miss focus follows mouse with no window auto raise. But man, it could be a lot better.
I need you to understand. I want you to feel what I feel.
On my desk, my mouse is less than an inch from my keyboard.
But every single time I have to take my hand off the keyboard - every time - a large buzzer sounds in my room, a million candle power red light starts flashing, and the overhead sprinklers turn on.
Ok, it’s not quite that extreme. To the observer. But that’s what it feels like to me. When I say I want to do everything on the keyboard, what I mean is every time I have to do non-keyboard interactions it is a massive disruption in how I work, move, flow. It breaks my interaction. Some of these are ok - scrolling is probably the least disruptive, although it’s such a core use case it’s amazing there’s no good option from the keyboard1. But clicking into a text box? Selecting text? *shudder*
I grew up remodeling houses with my dad. Imagine a hammer that required I put it down every time I needed a new nail. Or a screw gun that required two hands to load a screw, so I had to hold it between my knees on a ladder. Insane. You could never get flow. You’d throw that stupid thing away.
That’s what it’s like to use an iPad.
Let’s just pick the simple stuff. Something I do every day, often multiple times a day. Let’s walk through each little step, get granular so you really see it.
I have to make a calendar event based on an email. I’m in Apple’s Mail, and the calendar app is next to it. Again, there’s an air horn next to me, a strobe light mounted to my left, and a bucket of water above my head, ready to tip over every time I touch the screen.
I’ll be generous. We’re making the appointment for today, so no need to navigate within the calendar to pick the right day.
Task one: Switch to the calendar app.
Oops. I foolishly have both apps on screen at once. You can’t shift focus between those apps. Or can you? Wait, what does focus even mean on an iPad? No one knows. I’m in Mail, so I know it starts with focus. I lift my right finger up, and select the slot on the calendar I want. The world explodes.
In this case changing focus would not have helped, because Google’s execrable iPad apps don’t really support keyboard shortcuts. Huh. The company whose keyboard shortcuts are so dominant in desktop email that everyone else is copying them, doesn’t even use them on mobile? Maybe if Apple cared, Google would? Probably not, but since Apple clearly doesn’t, why should they?
I wipe the water from my face, and am now in the new event pseudo-pop-up. Oops, I need to copy the email address of the person, because it’s someone not in my contacts. I slowly, cringing, move my finger back to the mail app. How many taps does it take to get to an email address? I’m not sure, but I think it’s about four. It should be Cmd-Tab, Cmd-R (to reply, which I have to do anyway), Shift-Tab a couple of times to get to the To field, Cmd-A, Cmd-C to copy the address (I can use arrows and such to get just one if I want), Cmd-Tab to get back to Calendar, Cmd-V to paste.
Yeah, not here. I think focus is now in the calendar app, so I have to touch the mail app again anyway. I hit the reply icon. I use Shift-Tab to get to the To field, which mostly works. I then try to copy the address. This fails at least 50% of the time. Like, just fails. I mean, the buttons on the keyboard work. But when I try to paste elsewhere, the clipboard appears to be empty. Or something. Nothing happens. Since I’d rather have a crappy workflow than an inconsistent one, I use my finger again to touch the email address. How does one copy an email address when copying doesn’t work?
You don’t! You drag! Because absolutely, the one fix I want to bad keyboard shortcuts is different touch experiences. I love that drag and drop is more powerful now, but can’t you get the basics working, too?
Honestly dragging is also inconsistent, but weirdly, I’ve found it’s more consistent than the keyboard. I frequently swap email addresses in a mail - when I respond to an intro, I swap the default ‘To’ person to BCC, and move the ‘CC’ to ‘To’. If I drag them around, it almost always works, but if I use the keyboard, it just… doesn’t. It fails differently all the time but nearly always fails.
Ok, so I drag it into Google Calendar. Hmm. I can’t seem to drop it on the Guest field. Maybe because it’s not the active text field? Ok, I let go, touch the calendar, and then tab to the guest field.
Hah! Just kidding. Tab doesn’t work, it just puts tabs in the event title. I touch the guest field, and drag again. This seems to actually work.
By now, I have successfully put a person’s email address in a field, and I’ve had 14 buckets of water dumped on my head, I’m flash blind, and I’ll never hear again.
I won’t bore you with the details of actually getting the rest done. Obviously GCal not having keyboard shortcuts of any use hurts a lot, but even better shortcuts would not help much, because the biggest disruption is switching apps back and forth, and once in an app, picking the correct field.
And before you tell me to switch to Fantastical or something, please. My calendar is currently showing eight separate calendar feeds, all different colors so I can easily tell them apart. E.g., mine, my wife’s, my travel, my kids, the two soccer clubs I follow (#gunners #RCTID). My main event feed further colors every event by event type. Just today I can see four different colors of event. And I only have one meeting I’m personally attending. Apparently no one else does this, because no other apps even come close to Google in effectively managing this overlay of info. Don’t @ me. I don’t know how you people live.
And also don’t try to tell me I should automate this whole process. Sure, you’re right. Except again, it would only work sometimes, I’m always dealing with natural language text that doesn’t easily parse, the automation would be brittle and I’d move from being pissed off at Apple and Google to being pissed off at my own code, and I’d spend my time trying to figure out how to build abstractions over similar automations on different platforms, version control them all, package and deploy them, and suddenly I’m trying to use Zapier with microservices in a docker container in a VM on my iPad just so I can create an event. That’s definitely better.
It should be clear to you by now that every time I do this from my living room, my basement floods, my neighbors call the cops because of the sirens, and the lights have knocked countless birds from the sky. It’s a disaster.
And this workflow is one of my most important, most common.
The basics just don’t work. Maybe you didn’t know you can “minimize” an email by dragging it by its top bar to the bottom of the screen. Where’s the shortcut for that? What about the one to cancel an email? Honestly just deleting email with the keyboard fails most of the time, and 100% of the time after the first few. Delete, delete, ooops now it doesn’t work. Of course, this is true on the desktop, too, so…
Everyone else, all the other app developers, they follow Apple’s lead. They know Apple does not respect the keyboard. So they don’t either.
But the thing is, this diatribe has nothing to do with the keyboard.
It has to do with my flow. And the flow of everyone who uses this device.
I love my iPad. But Apple has clearly not taken a critical eye to where it supports flow, and where it breaks it.
I grew up on a hippie commune in rural Tennessee. When I was about 7, the state built a bridge across a ravine, which shortened the drive to Nashville by 30 minutes. One bridge, and suddenly a trip we took all the time is an hour shorter, round-trip.
One little simplification can have a massive impact.
Apple is adding features, but not connecting them. They’ve run a freeway into town, but haven’t built all the feeder roads so people can use it. There’s a fancy bridge between two cities, but the roads to and from it are still gravel. There’s a high speed train between cities, but the stations are outside of town and you have to walk there.
It’s not enough to put things in place, they have to fit into a coherent, cohesive system.
And until Apple respects the iPad enough to really think about how it all fits together, I will finish my work day soaking wet. Brrr.
Now, about that new iPad
Naturally, I bought one of the new Pro models when it came out. I have the original (2016?) 12.9" at home, and also the 10.5" that came out in the spring of 2017, both with LTE and the keyboards, and one pencil to share.
I almost never use the big one. It’s just too big. It doesn’t fit into my EDC bag (mostly because that was specifically chosen to fit the smaller ones), it’s too unwieldy to read in bed on, and it’s just hard to move around like I do with my main one. I mostly use it to watch soccer games on while I’m making breakfast on weekends. I’d sell it, but we often have five kids at our house playing Minecraft or Roblox, and I would never hear the end of it if we were short one.
I think Apple did exactly the right thing by making the big one smaller and growing the screen size of the small one. I don’t think it will, but I really want the new big one to work for me. The thing I miss most about my desktop is the big screen. I want more space, bigger screens, multiple of them. I had two screens on every one of my computers starting in 1998, until I got this 27" iMac - the screen is finally big enough, and managing windows on multiple monitors on a Mac was just not worth it.
So, I got the big one to try it out. I bought it just before heading out to visit my family for the holidays. I left my smaller iPad pro at home, to force me to use this for everything, including reading books in bed.
I returned it on the 14th day.
I loved it. If I were still gainfully employed, I would have kept it. I’m having to optimize a lot for lack of income right now, and that goes big time into my decision. Even without that constraint, a lot is riding on iOS 13 to deliver real improvements. I’m expecting to be disappointed.
The reality is, the device is too similar to the two I already have. When I was less money constrained, it made sense to take every incremental upgrade. Today it does not.
For all my lack of keeping it, though, I think it’s worth sharing my experience. I think it’s enough different from others that it stretches the tapestry a bit.
The bigger one is enough smaller that it really does feel different. I could see myself traveling with just that, no smaller one - I just did for ten days. But I would have to replace the bag I have carried for years. A bigger bag would mean I’d pack more, and be less happy. But honestly, I think it would be worth it. I could consolidate to just one iPad, mostly portable but big enough to be more productive. I would love that.
One area performance was immediately obvious was loading photos. One of the things I love most about the iPad Pro compared to other iPads is just how fast it downloads from SD cards. last summer I took more than 6000 (yes, you read that right) photos, mostly on my Fuji XT-2, and processed them all on my iPad. The connection on the Pro is waaaaay faster than on the normal devices, and it makes a huge difference. The new one seems to download the photos even faster, so fast the thumbnails are shown even more slowly than the data makes it onto the device.
That being said, most of the speed doesn’t matter that much to me right now. I’m typing this on a 12.9" that’s almost three years old, and I suffer through the app reloads and web page refreshes that the new one did not force on me. But it’s a pretty minor sacrifice for what I do, which is mostly reading and writing.
One of the biggest features in this new one was a mixed bag. I love having Face ID. Sometimes. Apple stubbornly insists this is a portrait device. That’s wrong for the smaller device usually, but always for the big one. Like, literally, I never use it in portrait mode. I know some do, in a stand or something. I don’t. That poor decision by Apple compromises Face ID so badly that I think they’ll move the camera in the next release. Here’s why:
I’m right handed, so I use my right index finger for most touch interactions. This leaves my left hand to hold the device, move it around, etc. And when I do that, where am I holding it? Right over the camera.
Pair that with the fact that Face ID is built to be used less than two feet from your face, and it’s a bad setup. I am sitting on my recliner in my living room, and every time I use the device here, it would say, “Face too far away”. I grab it with my left hand to move it closer, and now I’ve got the camera covered.
When I got the iPhone X, it was a magical experience. I just did not notice Face ID. On the iPad Pro, I’m getting a constant “You’re holding it wrong” experience instead. I’m having to babysit how I log in or authenticate, and have constant friction. Again, all because Apple is wrong about how their customers use this device.
The other big feature is the new pencil. I would use this one more than the old one, but not a lot. I basically only ever use them when taking notes in meetings. That was much more important years ago, less so now, but it’s still not that useful for how I work. Most of my text apps don’t support it (e.g., the app I’m writing this in, Ulysses), so any notes get sequestered in Apple Notes, which is a consumer app that fails quickly for me when asked to do complex information management. I need complex folders, with PDFs sitting next to notes and text files. I mean, duh, I want to organize by content subject, not content type. Plus my handwriting is illegible. So I agree the pencil setup is better, but that’s more a statement of how bad it was than how clever or great it is now. I know this matters a lot to some, just not that much to me.
The larger screen really is better. I don’t do “multitasking”, but I often have two apps on screen. E.g., when I process email, I almost always need to look at my calendar. With the bigger screen I can have my calendar in a small window, showing daily view, and it works great. I can only do this on my small device if I squint a lot. Being in my 40s is awesome. (It’s not all work; I also often have Destiny Item Manager and Discord open at the same time.) Again, note, this is about allowing me to get all the apps for one task on a screen. The computer is multitasking, I am not.
The new keyboard folio is pretentiously named, and such a bad wrapper for such a beautiful device that I’m embarrassed to touch or see it. I think technically the first case for the first iPad might have been worse, but wow that’s a low bar. So I have three color choices for my $1500 device, but I have to wrap them all in a slate-colored piece of vinyl? Shameful.
I guess the new setup is better. I definitely love having two angles, and it’s certainly less confusing for others to use the device. It’s a bit more disorienting for this expert user, though. I never got lost on my old iPad, but this one is sufficiently featureless that I’m always struggling to hold it in just the right way when opening it. Where’s the hinge? What corner does the camera go in? I frequently felt like I was studying a foreign object rather than using a well-known device. It needs to be far more obvious how to grab it, how to open it. The asymmetry of the old one was ugly, but you would never be confused about where the hinge is, or the bottom, or anything else. And the keyboard being exposed on the back is just a mess. It gets filthy, that filth passes to the screen, etc. Yuck.
That being said, the actual keyboard bit is better. I am typing this on the old one, on my lap, so clearly that was never a problem for me, as it apparently was for others. But the new one is more rigid, and the actual typing seems better. I mean, not good compared to my mechanical keyboards, but better.
So for this one, I’m calling a pencil: Wow the last one was really really bad. This one’s a bit better, so it’s only really bad. Unlike the pencil it’s a real downgrade in orienting yourself on the device when you first pick it up. The materials and handling issues guarantee no better than a middling grade.
I like smaller bezels and the new form factor, but honestly none of that matters to me except for how it makes the device smaller. Yes, Apple has a knack for industrial design that immediately makes everything that came before seem antiquated, but I’ll suffer through somehow. My car is six years old. I’ll be ok. I’ll just start calling my old devices dadcore.
Conclusion
It often seems that Apple’s industrial designers are their favorite kid, and the software designers are only there because someone has to fill the machines with stuff. Jony Ive gets to lovingly expound from his featureless white room on the physical bits, but, ah, not so much on what it’s like to use it for anything other than a dinner plate. That’s someone else’s job, someone else’s love.
I don’t think this is “new Apple”. Holy cow I hated early releases of OS X. Yes, it’s far more important than my interfaces be lickable than usable. Of course.
Apple’s operating systems usually do have a much user experience than others. But, ah, you’re comparing yourself to XWindows, which still can’t automatically detect an external monitor2, and Windows, which is a clean-room copy of MacOS done by aliens. The competition isn’t exactly fierce.
After college, I switched from MacOS to BeOS. I loved that OS. There was so much forward thinking in it, and there was a real conversation about what usability really meant, with a close connection between the people building it, developing for it, and using it. When it went away, I had no real choice but to switch to Linux. Literally every year I cycled through all of the distros in hopes of finding one that didn’t require me to hand-maintain my X.org config to support two monitors, but always ended up back on Debian, because at least its packaging was sane.
I finally switched to Mac when I realized: Once a year, I spend a week being livid, utterly pissed, bright red and burning hot, at Apple, all their products, and how they seem to just not like or trust their customers.3 But I spent an hour every day feeling like that about Linux. I eventually concluded I’d rather compartmentalize all of that into one chunk than spread it evenly throughout my life.
So yeah, I love my Apple devices, but, like, only compared to everything else. I hate software, but I’m pragmatic.
With that as a preface, here is the most accurate, but also most damning, review I can give for these new iPads:
They are a stunning implementation of the wrong thing.
The easiest way to see this is looking at the Apple logo on the back of the iPad. If you use the new keyboard, it’s covered in shame, but on my existing devices, it’s either hidden or sideways. If I am not using the keyboard, it’s wrapped around hiding the logo, but if I am using it, then I’m in landscape, and the logo is on its side.
The crazy thing is that Apple already learned this lesson! They used to ship their laptops with the Apple logo upside down. Or rather, it was right side up when just sitting there, but not when you actually used it.
Look, I don’t care about the logo. It wasn’t my blind spot that led to this.
What I care about is what it means that Jony Ive, Tim Cook, and all of the other leadership aren’t seeing these sideways logos every day, and tearing their hair out.
I’m trying to imagine an exec meeting there, with fifteen Apple logos sideways around the room, and everyone just shrugging. I can’t. Someone has to notice, be pissed off, right?
I can only conclude they don’t use these devices the way I do, and that causes me some despair. They still have a long road to walk. They’ll get there. But not soon.
The first thing I do every morning is turn off rotation lock, and enabling it is the last thing I do every night. I only need it enable when reading it bed, and the rest of the time I want to easily switch back and forth. This little bit of software friction cuts my usage of the keyboard by like 50%. One of the best things about using the big iPad is it’s too big to read in portrait, so this problem goes away.
A teeny software change could just ignore rotation lock when the keyboard is attached.
That software change would have happened ages ago if the people building these products used them anything like how I do.
Since they obviously don’t, I am not optimistic they’re going to make the right fixes.
Yes, there are a bunch of features they should add. But it’s more important they make a psychological shift in what this thing is for.
This device does give me some bit of hope. Even they can’t ignore the debacle that is Face ID with these things in landscape. That will push them to reorient.
Until then, you’ll just have to hide your sideways logo. But I’ll know it’s there.
Page up/down aren’t scrolling; most apps handle them poorly. ↩
I’ve no idea if this is true. But it was true last time I checked, and that time was in the 21st century, so it’s still embarrassing. ↩
This was more so at the time, around 2007, then now. ↩
I’m a tech founder and recovering SysAdmin. I helped found DevOps and grew up in open source. These days I am convalescing from a decade of physical and mental neglect while running Puppet.
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Photo courtesy of BP Miller.
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