Technology on Luke Kanies

Those Great New Calendar Tools Probably Won't Help You

luke@lukekanies.com (Luke Kanies) — Fri, 15 Sep 2023 00:00:00 +0000

They’re built for people who hate meetings, not for those who need to be great at them.

Photo courtesy of JEShoots.

There is a new movement around tools for managing your calendar. My favorite is Reclaim, but there are many others. They provide help running meetings, rearranging them, and avoiding them.

It’s great that these tools exist. The calendar is the least improved area in the average office worker’s life in the last few decades. My particular bugaboo is that calendar apps don’t know that you exist as a physical person, so they are perfectly willing to let you schedule two in-person events five minutes and 3000 miles apart. Any other kind of application would see that as a catastrophically brain-dead bug, but somehow the tools we use to arrange our lives don’t.

But… Something always struck me as off about these new tools. I didn’t want to use any of them. I’m a tool junkie, so this is pretty weird. Even Reclaim took me a while to understand and fit into my life. It was obvious these tools weren’t for me, but why not? Who were they for?

They’re for front-line workers: Developers, accountants, SREs. I used to be one of those. I’ve certainly been yelled at enough by them for putting meetings on their calendars.

But I’m not one today. I haven’t been in at least a decade.

My employees at Puppet used to say they hated meetings (I’m sure they still do, they just don’t work for me any more). I would tell them: Replace “meeting” with “collaborating with my team-mates” and say that again, eh?

So yeah, I have a different perspective on meetings.

Not that I think they’re all awesome. But for me — and most other leaders and managers — meetings are how we do our job. The life of a manager is built around communication. Much of it can be unscheduled, and ideally asynchronous. But a lot of it needs to be direct, synchronous, interactive.

That interactive time is much less efficient than, say, email, which means managers have to schedule their time carefully to ensure they get everything done. And of course, employees hate it when a manager shows up at their desk unannounced and asks for time. They want that meeting scheduled, too.

So a manager’s day is built around meetings, and there is a new crop of tools to help with them. What’s not to love?

Well. The tools are built by and for people who hate meetings, and often who aren’t very good at them. Instead, I want tools for people whose job is built around meetings, and who know they must be excellent at them.

Managers do need help. Not nearly enough of them are actually good at the mechanical parts of their jobs, including managing meetings. But these tools are mostly about avoiding or constraining them. They’re for the people asked to join, not for the ones calling them or running them.

I hope these tools do well. I want there to be a mature market of great tools in this space.

But even more so, I hope to see a parallel mature market for tools to help make better meetings. The average employee suffers from all the meetings they have. If managers were better, there would be fewer meetings, and the ones remaining would be better.

That’s a much better world.

My Monopolies

luke@lukekanies.com (Luke Kanies) — Wed, 18 Nov 2020 00:00:00 +0000

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.

Responses from the tech industry have not been great. Many have laughed at congress members for their lack of tech prowess. Some focus more on what the tech companies haven’t taken over yet than on what they have. Others have claimed that tech is so different they have to be looked at fundamentally differently.

Tech is not special

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.

And they’re finally starting to make headway.

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.

Designing Tomorrow’s Privacy

luke@lukekanies.com (Luke Kanies) — Thu, 22 Oct 2020 00:00:00 +0000

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?

I know the bet I’m making.

But I also know it’s a risky one.

The Automator's Dilemma

luke@lukekanies.com (Luke Kanies) — Fri, 24 May 2019 00:00:00 +0000

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 Rights You Lost When the Document Died

luke@lukekanies.com (Luke Kanies) — Tue, 08 Jan 2019 00:00:00 +0000

There are many upsides to the era of the smartphone and the cloud. But I’ll never forgive them for killing documents.

Photo by Daniel Zurnau

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. ↩
I was on team break-up. ↩
I can’t believe you forgot mine last year. ↩

Review of the 2018 iPad Pro

luke@lukekanies.com (Luke Kanies) — Thu, 29 Nov 2018 00:00:00 +0000

The sideways logo gets hidden, rather than fixed.

Photo by eleven x.

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. ↩

We Were Promised Flying Cars and Five Hour Work Weeks

luke@lukekanies.com (Luke Kanies) — Fri, 26 Oct 2018 00:00:00 +0000

Work is not a zero-sum game

Image courtesy of Clem Onojeghuo

Remember those stories from a few decades ago, about how improvements in productivity and automation would mean that we’d only be working 5 hours a week by now? They seem as fanciful, and predictive, as The Jetsons.

It’s almost a punch-line now, because many actually work more hours today than back then. How could they have been so stupid?

Of course there is actually a lot baked into the fact that higher productivity has not reduced hours worked (nor, it turns out, has it raised wages for the bottom 50% of earners in the last three decades, quite contrary to the previous, oh, 200 years). But a big part of why that prediction seems so silly now is it included an implicit assumption: That the work we’d be doing today is pretty much the same as what we did then. You know, before computers.

And I don’t mean, they could not foresee how much time we’d waste on social media. Their primary mistake was not thinking about how we’d use the space created by greater productivity.

We’ve known for centuries that increased efficiency results in increased consumption - we keep improving fuel efficiency, yet we’re consuming more gas than ever. Why?

We also know that expanding a freeway has never reduced traffic congestion. It has the same cause.

Induced demand. People who would not have driven with only two lanes, because of all the traffic, will now drive if there are four lanes. Trips you would not have taken because of the gas cost now become affordable and reasonable.

If your goal was to get more people driving, and maybe get the resulting increase in economic activity, then I suppose you got what you wanted. But if you were trying to reduce traffic - which is why most people say they want more freeways - then you’ve failed. If anything, you made it worse, because now twice the number of people are stuck in traffic. You didn’t reduce the problem, you just spread it around.

Demand is induced in many other areas. I grew up remodeling houses with my dad and got to see the impact of pneumatic nail guns and paint sprayers, which automated a huge chunk of how we’d spent our days. Of course, we didn’t use that newly free time to sit around, we changed our behavior: We did higher quality work, we finished jobs faster so got more done in a year, and we lowered prices.

I ran into this perception conflict all the time as I was building Puppet. I’d say I was building automation for the data center, and salespeople and execs would say, “Oh, so you can fire sysadmins!” I don’t know what they had against operations teams, but no, I would respond: I can give you a choice between reduced cost at the same service level (i.e., you fire people), or keep costs the same but increase service quality.

“Wait, that’s an option?!” Without higher level tools like Puppet, people had no idea how to increase service quality. Cost was their only dial, so they focused on that, even if it made no sense. Once I gave them other choices, of course they wanted better quality.

So where success in 1999 was shipping twice a year, and not going down, like, that often, now success is shipping multiple times a day and never appearing down to your customers. The standards have changed entirely, and that change was made possible mostly through automation. You can bet Netflix doesn’t become the new standard for infrastructure hotness using the bad old manual practices of the 90s.

You might say, no, people’s standards changed and that’s what motivated them to invest in automation, but you would be wrong. They always wanted higher quality. They always wanted better service. They just felt they had no choice but to accept the status quo, until we showed them other options.

I’m not saying automation never destroys jobs, never reduces the amount of work to be done in an area. But it’s by no means the default result.

The first impact of automation is to increase quality. I felt this myself, building houses. The main reason I’m no longer a carpenter is because of how incompetent I was at setting trim nails. You drive the nail most of the way into the wood¹, then use a small punch to recess it. You cover that one little hole in spackle, and no one can tell. Unless you’re me. When I do it, I make a little sunflower, with a hole in the middle and holes all around in a circle, because I’m just that good at letting the punch head slide off the nail, into the wood. If we’d had the trim nailers that exist now, even I could have done a decent job. That kind of success might not have driven me out of the industry and into the welcoming arms of computers. I’m not a lot better typist, but the delete key does wonders for my self-confidence.

And let’s be honest about what we’re automating: It’s literally the most boring and least useful work we do. I wasn’t exactly high skilled labor, but I assure you there were more valuable things for me to do than try to set a nail while on my knees, bent over to the base molding. As a SysAdmin, yeah, my bosses thought my job was typing the same command 1000 times a day, but we can look back now and see that definition actually got in the way of the work, rather than being it. We had much more important stuff to do. Or at least, I did. Not sure about the bosses.

If we were all willing to drive cars from the 70s, while living in houses from the 70s (oh god the colors), using computers from the 70s (all three of them), watching channels from the 70s (all three of them), then yeah, maybe we could also work 5 hours a week.

But we all know what we’d do with the spare time: We’d make more work.

You’d do something silly, like write a book. And obviously, most of those books would be junk, but enough would be good that it would become someone’s job. And maybe the other writers didn’t actually have a knack for writing, but found they could be great at helping other writers. Oops, now you’re an editor, or a publisher. And now you’re working more than five hours a week again!

Stupid entrepreneurship.

Or maybe you don’t want to be a writer, you just hate Avocado Green enough to do something different with your kitchen. Oops, now your friends want the same thing, and you’re an interior designer.

Or maybe you realize that the gas-guzzling death-traps we all drive in are insane, and you figure out some way to start bringing those sweet little rides over from Japan. You know, just to fill the time. Because you can only consume so much of your day watching three channels (and remember, no ESPN in this scenario).

You’re not the only one that’s bored. Everyone else has more time, and a need to fill it. They can spend the effort to become experts in watches, furniture, bicycles, hiking, boating, economics, philosophy, or any number of other areas. And we all know the main outcomes of expertise, beyond insufferable newsletters: Demand for more specialized stuff, or enough disgust at the lack of it that you’ll just do it your darn self.

Some number of us won’t do the work, but we still want more, because why else would I have read three books on horology? It only takes a few people to step in to fill that demand, and suddenly your time is taken up.

And of course, if you want to buy that fancy Patek Philippe to pass on to your kid, you probably need to work a few more hours than the minimum.

So now you know why we don’t work five hours a week, and hopefully you have a little more confidence that automation will generally be good, not bad. It’ll create more entrepreneurs, raise wages, increase quality, and reduce cost. Not every time, but most times.

It doesn’t explain why those prognosticators in the 70s were so silly, but, well, I bet it wasn’t the worst decision they made that decade.

16oz Estwing finish head with a curved claw, natch. ↩

Owning My Strava Ride

luke@lukekanies.com (Luke Kanies) — Tue, 11 Sep 2018 00:00:00 +0000

I know what it means to own my code contributions Github, but what does it mean to own my rides on Strava?

Photo by William Hook

I recently went mountain biking in Bend, Oregon, which is a few hours’ drive from my house. As I usually do, I used Strava to record the ride. This was a new trail for me, and I got lost multiple times, so I also used Trailforks to figure out how to get back to my vehicle.

I’ve been thinking a lot about how services like Facebook start out helping us, but at some point the relationship shifts and we’re stuck helping them more. I don’t think Strava has gotten to a stage where the relationship is abusive, and maybe this is weird but I hope they stay too small to ever get there. Even without that shift, though, I am a little uncomfortable with our relationship.

I was standing on the trail, trying to find the right trail and idly watching a coyote search for chipmunks. As I switched between apps, I realized that I was losing a lot by recording in Strava instead of Trailforks. Or rather, I wasn’t; people who want to bike this trail in Bend were.

I log my rides (and my infrequent, hilariously slow runs) in Strava for, um, reasons. I don’t want kudos, and I don’t really look at my historical performance, although I do enjoy being able to study my rides at times. I want the data there, even if I rarely use it. And it conveniently automatically completes my daily exercise goal in Streaks. It’s kind of useful, but if it went away tomorrow, I wouldn’t miss the online component much, if at all.

If I instead recorded all of the trail rides in Trailforks, then everyone who came after me could get some value from the information provided by my ride. They could see what route I took, could likely tell based on my speed when I had to walk and when I was able to ride, and they could over time get a sense of what routes are most popular, or even what signage is confusing.

I built an open source company, so I’ve thought a lot about the worth of contributions. A developer’s time on one project can’t be spent on another. Someone who writes documentation for your baby is giving up the opportunity to contribute elsewhere. It’s a conscious choice on the part of the contributor, and a constant interaction between the project and its constituents to keep people coming back.

I think Trailforks really understands the value of my contributions: If you do this, people who ride here will have higher quality data, and probably better rides.

I am super confident that Strava knows the value of my usage: I’ll get feedback from friends and I can track my speeds and feeds. But those aren’t contributions; that’s not something I’m giving up for the greater good. It’s something I am doing for selfish reasons.

The value of my trail ride could be for the greater good, though. Even my road rides and runs could be, as they could help people find routes, but the trail rides especially seem valuable, because the downsides of being lost out there are materially worse than not having the right route for your run.

It’s clear to me that Strava is not seeing my data as a contribution. They’re focused on engagement. That’s not inherently bad - lots of people use and love the app - but it is different. I find it interesting to think of what the experience would look like if that changed.

But after that, I thought: Why can’t I just share the data with both apps?

I mean, to some extent I can. I can just run both of them and let each record its own view of the world. This is what I did with Slopes and Strava in Mammoth, taking the lifts up and riding down. That made a little more sense because neither quite has the correct view of the world - Slopes doesn’t know what bikes are, and Strava doesn’t know what lifts are. It was pretty kludgy, but more importantly, I didn’t run into this conflict because the apps exist to do pretty much the same thing, just for different sports.

I could duplicate here, I assume, but… it seems stupid.

Beyond our relationships to service providers, I’ve been thinking about what it means to own your own data. It sounds awesome, but it’s rarely very useful in practice.

It turns out, I do own the data that I have posted on Strava. Great! So I’ll just share it with Trailforks, too.

Hmm. What would that look like? Can I… download the data, and then upload it to Trailforks? Is it a common data type?

Can I record it separately on my phone and post it to both apps? Is that what truly owning my data would look like?

It’s hard to imagine that world: You use apps that generate data, which by default is yours and only yours. It gets recorded in forms that are easy to share, understand, and manage. If you like, you can then contribute that data to other sites, and in doing so, you get to negotiate with them exactly what rights you’re passing on. Either way you have the data, but now they get a copy, too. If you don’t like their offer, you still get the data, and most likely, given you have all your delicious data, other apps will crop up with a different offer, because they can focus on that rather than all the data collection.

It would look a lot like the text editor I’m using to write this article, Ulysses. It allows me to publish, but is built first and foremost to make it easy to write. Sharing, contributing, engagement, and all of the other online stuff is left to other sites, other apps, like Wordpress and Medium. And yeah, those apps do allow both writing and publishing, but it’s a horrible experience, a great way to lose data, and if you only write there then your data is stuck in their system and is pretty hard to get out in a useful way.

The world of writing looks weirdly different from the world of recording rides. And a lot worse.

I’m not in control. Legally I own the data, but, ah, I don’t have it. Strava does.

I would never write directly in Medium, so why am I logging my rides directly in Strava? What am I giving up because of it?

I’m pleased to find that Strava will allow me to give other people the data - the data that I own! - and it turns out that Trailforks knows how to slurp it out of Strava.

So it all ends well: My rides are in both locations, and every mountain bike ride I post to Strava will now be automatically imported intro Trailforks. Probably.

But for that brief moment, in Bend, while watching the coyote… I saw what it would take for me to really own my data. I liked it a lot.

An alternative crypto-history

luke@lukekanies.com (Luke Kanies) — Thu, 28 Jun 2018 00:00:00 +0000

Filesystems, version control, and the blockchain

Image courtesy of Adarsh Kummur

This is the fourth, and possibly final, article in my series on the blockchain without blockchain.

I’ve always had a warm place in my heart for filesystems.

I taught myself shell scripting while automating the installation of Disksuite, Sun’s free but sadistic disk mirroring software. I barely recall the actual work, instead remembering a hallway. I undertook a literal journey to learn programming, a repeated pilgrimage to the desk of a friend who took visible pleasure in explaining to me what I was doing wrong.¹ It’s fair to say that if filesystems were less painful in the 90s, I would not be where I am today.

When Sun started advertising ZFS as the (finally!) successor to Disksuite and the filesystem it was built around, UFS, most of its functionality seemed obviously good - make the computers manage the disks, don’t demand people know up front how big a filesystem should be, don’t fail miserably when the server crashes, little things like that. But what was this data integrity thing? I’m embarrassed to say it took me a while to realize I needed it - who really cares if your filesystem is good at storing data, amirite? - and even longer to understand how it worked.

To explain it, I’m going to have to teach you cryptography. Just a little. You’re welcome to skip ahead if you’ve already got this part covered, but I expect most could use a little, ah, refresher. Step 1 in cryptography guides is usually: “Get a masters in mathematics from MIT.” I’m hoping to do a bit better than that. Cryptography really is just a form of math, and while we can’t all understand the details (I certainly don’t) we can at least understand the “algorithms happen here” flow diagrams².

Cryptography is most famous for its privacy utility: You use it to ensure you and only you can read your files and chat messages. It gets more complex once we need to read them on all of our different devices, but most of it is pretty similar in concept. Even more useful is ensuring both you and I can read some text, but no one else can. It’s more complex, but is essentially an extension of that first use.

Privacy is not the only use case for cryptography. It’s also useful for efficient validation. That is, it can be used to see if a file you have today is the same one you had yesterday. I sent you a document, you think it looks wrong; how do we make sure it did not get changed somehow in transit?

Obviously one way to do that is to just send it again. This is not a great solution, because if you did not trust it the first time, why would you trust it the second? That might also be a bad idea if bandwidth is expensive. You generally want a verification mechanism that takes less space than the original file, and less CPU power than directly comparing the two files.

Cryptography provides just such a capability, usually called a ‘hash function’. It’s an algorithm that converts, say, a large text file into a much shorter string. If you want to ensure the file is not changed in some way, just run it again and compare the output. The short strings are easier to compare than the long documents, and you could even read them over the phone to someone so they can check the file on their end. These algorithms generally produce a string of a fixed length, regardless of input - this makes them efficient for long term storage and comparison, and safe to run on any size file. Here’s an example hash from my files:

03f39f4bfad04f6f2cfe09ced161ab740094905c

As you can see, it’s just a long string of gibberish. It’s not only useful for comparison, not meaningful in it’s own right.

What’s critical about these algorithms is that given a unique input they always provide a unique output. If you and I each have a file that hashes to a given string, then we can be confident we have exactly the same file. Of course, this can’t literally be true: We could design a hash function that only had 256 possible outputs, and there are obviously more than 256 possible inputs. This would produce a lot of what are called collisions, when two files hash to the same output, and, ah, is not terribly useful.

All of the modern hash functions are incredibly long. It is possible in theory but not in practice that a collision would happen. You’d need to execute the function 2^128 times. That’s 3.4 with 38 zeros after it. So, mathematically possible, but you can expect the sun to swallow the earth before the most secure hash functions get compromised. I mean, you can’t. You’ll be gone by then. But your files will still be safe.

Now that you’re at least as much an expert on cryptography as most of the bitcoin hodlers, why does any of this matter?

We were talking about data integrity.

You’d be right to guess that ZFS uses these hash functions to provide it. It goes further than just validating individual files. A little bit of cryptographic genius called a Merkle tree is the key. These don’t just hash the content on disk for later validation; they build a tree of hashes, where the leaf nodes are hashed by the nodes above them in the tree, which are themselves hashed by the root node. If any part of this system is corrupted - because the disk is broken, or someone changed the content some other way - it’s easy to detect. It’s not just that the individual hash will be different; remember each parent hashes all of its children, so now the parent is wrong. And its parent is wrong, too.

If the content is changed by any mechanism that does not also also update the Merkle tree, then it is easy to detect by rehashing all of the content and comparing the results to the stored tree.

This is how ZFS validates data integrity. It can write a block to disk, then pull the block and ensure it still matches the hash. When it writes a block, it updates the parallel tree, and when you ask for the block later, it can tell you if the block is still correct. If it’s not, it throws an error instead of handing it back to you.

When I first learned of this, it seemed overkill, but over time I remembered just how many ways there are for data to get corrupted. The most obvious one is someone changes it for nefarious reasons, but far more commonly you have a failure somewhere in the writing or reading process. The old spinning disks were error-prone, and the new SSD drives degrade eventually. It’s the complexity of reading and writing that really gets you, though: There are multiple layers of caches, drivers, and connections, any of which could introduce corruption.

For the first time on a normal production system, you could at least detect any of those problems. It’s too bad no one ever used it.³

I know, I know, you came to hear about how you could get all the awesomeness of blockchain without using the blockchain and instead I’m giving lessons on two things you could literally not care less about, cryptography and filesystems. Don’t worry. It gets worse from here.

Long after I learned about and promptly forgot ZFS (after all, it’s not like I was using it), I adopted Git. It’s a version control system, used for storing and managing source code. Every geek knows about it, but most of the world only recently learned of it when Microsoft bought Github for $7.5B with a ‘b’. I was an early adopter, switching Puppet to Git in 2008⁴. Eventually I even learned how it works. I was titillated and a bit horrified that I had duplicated in Puppet one of the key features that made Git work: A system of storing files that allowed them to be looked up by their content (or rather, a hash of their content). Normally you store files by a name, but if lots of people (or, in Puppet’s case, computers) store the same file, they might not call it the same thing, so Git and Puppet instead stored them by their hash. This ensured we never backed up more than one copy of a file, saving a lot of space, and made it easy to check for changes in files.

For Puppet, we just used this to back up files we changed, in case people later wanted to revert.

Git did a lot more than that.

Like ZFS, it builds a Merkle tree of the entire file repository, with a similar goal: To understand what files have changed and how. After all, git is used to track and share changes to a collection of files. The sharing is a critical component; you can easily copy an entire git repository to another computer, or another person, and it’s important that they be able to confirm that they have a faithful copy.

Git stores the hash tree alongside all of the files. At any point, you can use the tree to validate every file in your tree. If there are changes (which is pretty much the whole point of a version control system), it can automatically store the new files and update the related tree.

Just like ZFS, one of the key features here is that the Merkle tree allows us to validate every file stored. We can walk the file tree and compare each file to its hash, and then compare the file listing to its own hash, all the way up. Any discrepancy is easily spotted.

This is my favorite kind of cleverness: It’s simple in implementation, yet makes Git more flexible and useful. It has power that other version control systems are missing, just because it relies on this basic mechanism for storage and validation.

Ok. Now we get to the point.

Again, I’m not actually interested in the blockchain. I’m interested in peeling it apart, putting the useful bits to work while avoiding the whole anarcho-capitalist aspect.

It would be easy to see the blockchain as a sudden revolution, a dramatic change in what’s possible. Viewed this way, it’s hard to separate the pieces from the whole. If all you see is the big picture, it’s easy not to notice that every individual component has its own history, its own value.

The blockchain was gradual, for both me and the industry. It was not one giant leap forward. It was part of a story, a sequence, and the most interesting aspect - Merkle trees - is decades old in math and now pushing decades old even in popular usage. Most of the interesting features touted in the blockchain come directly from them. Immutability (which isn’t) and trustless systems derive directly.

It’s worth understanding that history, to see which stages and steps apply to problems you have. The current cryptocurrency tech stack is built to solve problems I don’t think exist. Certainly they aren’t problems I have.

Unlike the blockchain as a whole, though, the individual technical components have been used for years, even decades, in production. Focusing on the current trend can blind you to the opportunity history demonstrates. I think you’re a lot more likely to find broadly applicable solutions there than in trying to replace currency.

Because I got here from the world of filesystems and version control, I see different benefits than you might if you approach thinking of currencies or exchanges. Or chat messages. That does not make me right or wrong, but it does, at least, mean we’re going to work on different problems.

I expect most of you think this is boring. That’s great. It will give me that much more time to build something.

My brightest memory is learning that of course the ’echo’ command resets the exit code variable. This was a critical early lesson in how your own debugging can dramatically change the behavior of a program. ↩
When people talk about the futility of trying to ban cryptography, this is what they mean: You can’t ban math. ↩
Yes, I know some people use and love ZFS. But never to the extent it should be. ↩
Resulting in one of our critical community members abandoning Puppet in protest, for some reason. ↩

The virtue of a tool

luke@lukekanies.com (Luke Kanies) — Tue, 19 Jun 2018 00:00:00 +0000

Vendor success should be about customer needs, not its own.

Photo by Philip Swinburn

I am a tool junkie. I love the effortless balance of a well-known chef’s knife, like my hands know what to do all on their own. Heavy usage builds callouses and tunes muscles, its usefulness evidenced by scuff marks and changed infrastructure. Failure leaves blisters or even hospital visits in its wake.

A good tool proves its utility. Knives slowly shrink with sharpening, work pants thin, machines need oil. If they don’t, you’re either not maintaining your tools, or barely using them.

This wear is proof of your usage. They should be scratched. Dented. Aged. Patinas should be acquired from the shop, not factory treatments. Their callouses should pair yours. Tools can not be precious. They’ll just live on a shelf, then retire to your attic. You should seek that perfect middle ground, where you spend enough money that your kids can inherit them, but not so much that you are squeamish about giving them a job.

Tools only deserve the label if they help you work.

You might say I have strong feelings about them. I’m assuming this love led to my focus as a software entrepreneur on helping people people work. Or maybe my experience with tools in the physical world led me to seek them in the digital world, learning to make what I could not buy.

Given my tool fetish, you’d think I’d have a solid grasp of what I mean when I use the word. Apparently, not so much. I was recently pulled up short by a simple question, asked by Jordan Hayles of the Radical Brand Lab: What do you mean by tools?

What do you mean, what do I mean? It’s a simple question, right? The above text gives one example, but I would have thought I could answer it in a bunch of reasonable ways, none of which seem terribly controversial.

But the more I explored, the less simple the question became.

I’ve been describing my goal as building power tools for people. This phrase comes from my time building houses with my dad, and ‘power tools’ just meant the things you plugged in. You know? Because they needed power? It’s a common usage, maybe the word choice here did not mean much.

Except… I’ve spent more than a decade learning product management, describing myself as a product-oriented founder, managing that function in a growing company, and attempting to teach it to others. Yet here I am ignoring both the term and the field entirely. Why am I so quickly dumping my work of the last ten years? Is it just creative branding? Cynicism about my industry?

Why not power products? That’s a motor boat of alliteration: ‘power products for people.’ Awesome, right?

Ok, maybe not.

Product management as we know it began in the consumer goods industry. You’re handed a train car full of dish soap and told to sell it. You’ve got to package it, set pricing, convince a local store to carry it, argue with them about location, move it away from competitors, all that. Every product you see in your local grocery store is loved by a product manager who fights for its shelf space, believes it is beautiful, and wants you to give it a good home.

Tide soap is one of the most commonly stolen consumer goods, but not because it’s soap. The strong brand makes it easy to resell, even allowing it to be used as a stand-in for money in drug deals. I wish I was that good at product management. For all that, it says nothing about the soap.

Product management can also be used for evil. Laser printers had toner cartridges you could just refill. Not very clean, but cheap and reliable to run once you plonked down the cash for the expensive printer. Modern inkjet printers instead use disposable cartridges. To sustain profit margins in a rapidly commoditizing industry, manufacturers started putting rules in place on the cartridges: You had to buy them from the manufacturer, they had to be replaced every year, you could not refill them, you could not print in black and white if any color cartridges are empty.

The user was getting hurt so the vendor could make more money. People got pissed of enough that the US Supreme Court weighed in.

That’s good product management. Well, it’s evil, but you know what I mean. It’s effective. We’re talking big-B revenue effective. Hmm. A moral distinction begins to reveal itself.

These are examples of companies forcing their business model onto their customers. There’s no difference between the dish soap sold at retail and the one sold in bulk, yet they’re separate products, differentiated through packaging, shipping needs, and labeling. You pay much more for the retail package than the wholesale one, primarily because the business model behind them is so different.

But when I think of a tool, these complications are missing. When I use a hammer, it just has to fit my hand and smash stuff. When I pick up my drill, it works with every bit I own, regardless of the logo. The battery and charger are proprietary, but the vendor’s most visible role in my life is color choice. My yellow drill works just fine with bits from the blue or green companies. (You probably visualized brands by my just mentioning colors. That’s still effective here.) It does not matter whether I bought the drill from Home Depot or inherited it from my dad; once in my hands, it just works.

I think this begins to answer the question of what a tool is.

It helps you do your job, without your worrying about the vendor’s needs.

I know that DeWalt and Mikita need to make money to sell me a drill, but I don’t think about it when I’m using their tools. Even after more than two decades without one, I can comfortably recite that “my” hammer is the Estwing 22oz waffle head with a straight claw¹, but none of those details mean I need the vendor’s permission to hit a nail with it. I make a decision about the right tool, I buy it, I use it. End of story.

It is small. If you call something a tool, not a product, you’re saying it’s less, it’s not as complete a solution. This can be belittling, insulting, but it does not have to be. It’s also a statement of independence. Of freedom. Of, and this is going to sound crazy, compatibility.

Products have an implicit, ongoing dependence on their vendor. If that’s me, I love it: I want you to pay me all the time, not just once. That ongoing relationship is how I afford to keep improving what I’ve built for you. This can be a great way to ensure we have a long-term, sustainable partnership. But it’s not always a healthy relationship. The more you have to deal with how I make money, the worse the experience is for you.

I think this is what I like about tools. They’re self-contained. Independent. Using them is fundamentally pragmatic, not a lifetime commitment.

That independence has downsides for me as a vendor. You don’t get any of those delicious growth-hacker buzzwords. Your product isn’t “sticky”, there’s no “moat.” Those are examples of my customers being constrained by my business model, and their absence means revenue is harder to build, to protect.

One might argue I’m better off because treating my customers with more respect makes a better business in the long term, and I’d probably agree. This kind of respectful partnership should deliver higher returns than one that traps and mistreats its customers. I think this is often the right answer, but it’s not a popular one. It’s harder to get funding, to get off the ground. I might be accused of not “wanting to build a real company,” or I might have Silicon Valley’s most dire insult hurled at me: “That’s just a lifestyle business”.

Tell that to Adobe. Or AutoDesk. These are great tools companies. They are the behemoths we know today because they knuckled down and solved their customers’ problems. They worried about that, rather than how they could extract maximum revenue over time. It was a different time, but people have not changed.

I don’t think that every product is compromised when the vendor’s needs show up in the customer’s life, but I think most are. Some of it is laziness, shoring up product limitations with business model innovations, but a lot of it is strategy, recognizing the value of painting your customer into a corner.

Honestly, some of it is just survival. A lot of those inkjet printers are unaffordably cheap, but buyers care only about cost, not value. Some markets are intrinsically dysfunctional, with users and vendors slowly killing each through bad deals and cynical behavior. But as a vendor, I get to make a choice about what markets to play in, and how to work with my customers.

I am a simple person with a simple dream: I want to build something that helps someone work. I have to make money while doing it, because that’s the nature of the job, but I’m more interested in my customers’ work than my own. I know I need a business model, a go-to-market strategy, a plan for growing and supporting my business. But my customers should not need to care about that, should they? If they like what I’m building, they should be able to buy it, and use it. And tell all their friends how great it is. They should not wake up one day to find they’ve accidentally gotten married to me.

I just want to build tools. And I’m proud of it.

We told with great pleasure the (most likely apocryphal) story that this hammer was illegal in Florida because the metal haft could cut your thumb off. ↩

Decentralize Your Data

luke@lukekanies.com (Luke Kanies) — Thu, 31 May 2018 00:00:00 +0000

What does owning your data even mean, and can the Blockchain help?

Photo courtesy of Dennis Kummer

Congress recently required Mark Zuckerberg to defend his lifelong practice of mistreating your private information. Movements to give you control of this critical data took the opportunity to claim they can prevent future such breaches. Blockchain is the new solution in search of a problem, and personal data is in the crosshairs.

But can the blockchain actually help secure your personal data? What would that take? And seriously, what do people mean when they say we should own our own data?

It sounds nice. Too bad it won’t help. The problem is not “ownership” (whatever that even means in a world of infinite digital copies). It’s centralization. Having one person’s data is a small threat, only to that individual. Having everyone’s data is a national crisis.

By now we’re familiar with the huge amounts that Facebook, Google, Amazon, and apparently everyone except Apple have on us. But how did they get it? Mostly, we gave it to them, through using their products. What we didn’t give to them, we gave to someone else who then passed it on.

There have been massive breaches at Equifax, Facebook¹, and many others. Even the general public is becoming aware of the real causes. Some of the the largest companies in the world exist purely to collect your information and sell access to you based on it. They might not sell your data, but they definitely sell your attention using it.

These are the problems you know about. Don’t worry; it gets worse from here. If you think your birthdate and pictures of your kids are personal, what about your DNA?

Anne Wojcicki is married to a Google founder, and she liked their data accumulation so much she started her own company to build a huge pile of even more personal data. 23andMe does not scrape the internet - or your cheeks - to get your DNA; no, people pay for the privilege of giving it to them. Yes, they offer a service in return, but do they clean house after? Hah! No. They keep it. (Hopefully somewhat more safely than Equifax does.)

What’s so wrong about there being a database of DNA from a big chunk of the population? Let’s ask the police.

You might not be afraid of the police. You should consider yourself lucky. I know anyone of color in the US is and should be. I know I am; I grew up on a commune, and policed raided us using helicopters and assault rifles in hopes of busting us for cannabis. I don’t mean to imply that hippies have been as systematically oppressed as African Americans (and certainly not in the south); just that I grew up with my own justified skepticism of exactly what that force was here for.

Even if you don’t fear the police, you should fear the consequences of DNA testing. The science behind most parts of DNA are absolutely rock solid². The police work is another matter. Beyond outright fraud used to wrongly convict people, the messy world of testing DNA at crime scenes just makes it hard to get correct results. Juries inappropriately treat a complicated test as foolproof. It could be compromised anywhere from the crime scene to police handling to the lab itself. The failure rate even without fraud is high enough that I would not want to trust my life to it.

Not to imply that DNA testing is worthless; quite the contrary. It has been used to exonerate many people who were incorrectly imprisoned and put on death row. It’s not that it always fails, just that you don’t want to finding yourself gambling on it against life in prison.

But remember: This is just for cases where someone has a single person’s DNA. Like having just your fingerprint. What happens when someone like 23andMe has a whole database of it?

“If you didn’t do anything wrong, then you have nothing to fear.” Pfft. Yes, it starts with requests for the DNA of individual suspects, but it escalates to doing a database-wide search for DNA that matches. And by ‘matches’, we don’t mean, “is 100% guaranteed”, we mean, “eh, it’s pretty close”. A DNA “match” directed the police to someone they thought was a relative of a suspect, who was then brought in for questioning. So I guess as long as you’ve never done anything wrong, and aren’t related to anyone ever doing anything wrong, you’re fine. Right?

I feel so much better.

I had investors literally laugh at the idea that collecting this data introduced security concerns. They grew up at Google, so it’s not surprising they could not see centralization as a problem. Just like Equifax started out wanting to make it easier to get loans, and now they’ve got so much power you can’t get one without them.

There is a world of difference between giving someone your data, and allowing someone to include your data in a massive pile of it. Any discussion of the risks of data needs to acknowledge that.

Now we see our discussions of owning your own data don’t quite have it right. What we actually want is decentralization of data. We don’t want a single company to have access to this much information about huge groups of people.

And now you see the problem.

New technology can’t break Facebook’s business model. It can’t prevent Google from scraping every web site on the internet and identifying you by connecting everything. Whether you give it to them or not, they’ll know what you look like, where you live, and who you hang out with.

Most importantly, it can’t prevent people from sharing all that data with these services. After all, they’re getting something valuable in return, like connecting with friends and family. Or figuring out their family tree.

The problem is not the centralization. It’s the effectiveness of a business model built on centralization.

So anyone who comes to you and says “The blockchain will allow you to own your own data!”, ask them in return, “How will you make it such a joy to use that Facebook will go bankrupt?” And please, record the conversation, because I want to see them stammer.

This is fundamentally a product and design problem, but the technofuturists are treating it like a technology problem. “Oh, if only those college students had access to better cryptographic tools they never would have shared that data with Facebook!” 🤯 No. People will stop using Facebook, and 23andMe, and Google, when there are better solutions. And unfortunately, they need to work ten times better, not just a little bit.

So talk to me about the blockchain. I really do want to hear how you’ll use it to help people own their own data, and remove the incentive to centralize all of this data.

But talk to me of products. Of user benefits. Of business models built around all of this.

Because people have to want what you’re selling, and the only way to get that is to build something they want to use. Only then will they be able to own their own data.

This is the third article in a series of indefinite length on The Blockchain Without Blockchain

Although technically not a breach, since their usage rules weren’t broken - that’s how little they respect your privacy. ↩
Although we’ve still got a lot to learn about the epigenome, so don’t think we’re done here. ↩

Blockchain without Blockchain

luke@lukekanies.com (Luke Kanies) — Wed, 09 May 2018 00:00:00 +0000

There is powerful technology hidden in the blockchain. Just strip out the parts everyone cares about

Image courtesy of MemeGenerator

People are very excited about the blockchain, convinced it’s going going to replace cash, or gold, or credit cards, or even the internet. I’ve even read claims that it’s the most important invention since little things like money and democracy. Starving through a failed attempt at utopia has taught me to align with the skeptics who point to the lack of proven use cases (other than fraud and crime), and with the pranksters who make fun of the claims of salvation.

That doesn’t mean I think it’s worthless.

The economic use cases (cash, gold standard, “sound money”, etc.) rest somewhere between unproven and conspiracy theory. None get any love from me. Just because I don’t respect the Austrian school of economics doesn’t mean I don’t understand it. They’re so stuck on their commitment to not learning from history that they can’t let go of the switch away from the gold standard. I am also not silly enough to think that the anti-government libertarians are in it for anyone but themselves.

I’m only here for the tech, people.

The world of the blockchain is in a state of flux. This is normal for movements, and especially so for the definitions of words to be shifting quickly. I experienced this directly as Puppet was helping to create the DevOps space. Today, when we say ‘blockchain’ we mean a specific set of features provided by the code underlying Bitcoin; some might add the requirement for smart contracts, as added by Etherium.

This definition won’t last.

I think that when we look up in five years, the word will mean something quite different. As the conversation inevitably shifts from hype about its universal applicability to finding practical use cases, I am convinced the term ‘blockchain’ will invert from its maximalist form, including all possible features, to a much more minimal form, defining a base set of functionality that is suitable to solving far more problems. Different implementations will layer features onto that base set, but all of these derivatives will be called ‘blockchain’ (which will soon have purists crying we’re not using the “real” blockchain).

It’s that base set of functionality that I’m interested in. I’m hoping the world’s excitement over the complete package can turn into momentum around a more flexible solution. What can we take away, and what can we do once we strip things down?

Let’s start with the most obvious thing we don’t need: Lack of trust. Free markets are built on trust, so it’s silly to try to build one that doesn’t. I just don’t run into many problems that can only be solved if I never trust anyone. Even writing that out makes me cringe.

I’m interested in power tools, user productivity, and helping teams, which inherently means I’m interested in people who know and trust each other. That isn’t to say data validation and simple synchronization are never helpful, but trust between people is not a problem. So take out that whole part of the story.

Next up is consensus. Let’s be honest: You don’t really want the world to have access to most of your data. And most of you who do, well, it probably doesn’t want to see it. This solution for deciding whose copy of data is right? I don’t need it.

That isn’t to say there aren’t important consensus problems; it’s just that the blockchain’s version of them is not useful to me. I do actually struggle with managing conflicts in my own work. I’m writing this essay on one of the six devices I regularly work from, and I obviously want it to transparently synchronize between the rest. I can dream about never having conflicts, but in the real world I need a simple way to handle them when they happen. That’s my consensus algorithm. If I use the Blockchain’s, then one chunk of work wins and the rest of the work gets thrown away. That might work well in some environments, but is obviously a non-starter for my personal work. Instead, I need an algorithm that gives me control over managing my own work streams.

I expect a blockchain hodler would flip at calling this a “consensus algorithm”. It’s not. It’s more like a tool for managing merge conflicts. If you buy into the blockchain, you’ve added a ton of complexity that can and should be handled by a person.

It’s not a big leap from managing conflicts between one person’s devices to managing conflicts within a team. This is still an important problem, one wrestled with by anyone building online collaboration tools, but requires nothing like the level of infrastructure built into the blockchain. After all, I trust myself. I trust my team. I like to be able to verify, but I’m more worried about mistakes and data loss than I am about intentional subversion of the system. And actually, the current solution is horrible for teams. It’s one thing for someone else’s work to cause yours to sit in a queue for a bit, it’s another thing entirely to have your code thrown away because someone is in front of you.

Taking out the trust-less consensus allows us to remove the worst part of bitcoin: Proof of work. This is how parties in a blockchain transaction fight to have their work accepted and others’ rejected. If they win, they are rewarded with a token, which is how they’re “paid” for their work.

We don’t need any of that.

We’ve already established we don’t need an automated, trustless process for deciding who gets to update the database (and we’ve concluded we don’t want conflicting just thrown away). As a result, this whole mechanism can just be removed. Good thing, too, because bitcoin is in the process of consuming all of the world’s natural resources in the name of never trusting anyone. This also simplifies the problem of scaling these databases. Bitcoin is stupid slow because its proof of work system is stupid slow. Remove that, and any iPhone can trivially record new data as fast as you want.

Now that we don’t need proof of work, we also don’t need, surprise!, the currency itself. In a trustless system, tokens are used to compensate the networks recording the transactions. This is now so cheap we don’t need to reward people to do it.

There you go. Now you’ve got the blockchain, except without cryptocurrencies, trustless transactions, consensus algorithms, or proof of work.

The blockchain without blockchain.

It’s important to note: It’s not that I think none of these features are ever useful in any case. It’s that none of them are necessary to get the most important features out of the blockchain, and each of them should only ever be added to a system if they’re truly needed. In most cases, YAGNI.

What can we do now? Well, obviously, now that we’ve removed so much functionality we can do a lot more. General purpose languages are more powerful than specialized ones, and a more flexible database is a more powerful one. The current set of blockchain features can really only be used for a narrow set of use cases, and even those seem to be more theoretical than actual.

What’s left?

A database. That’s what the blockchain always was anyway. It’s built on Merkle trees, which means you can validate every change back to initialization if necessary. This makes it kind of trustless: I can validate your work, rather than just trusting your word of what you did. This ability actually encourages me to trust you more with my data, though.

Check back later for more about what I mean.

This article is the first in a series of indefinite length. I’ll explore the consequences of this stripping away. I will also address some of the potential I see for full current blockchain feature set. I look forward to approaching this topic from a different direction.

The power of better tools

luke@lukekanies.com (Luke Kanies) — Tue, 24 Apr 2018 00:00:00 +0000

There is a solution to wage and productivity stagnation. Just don’t call it automation

Image courtesy of Washington Department of Transportation

I don’t know what the rest of the world thinks when they use the phrase ‘power tool’, but for me it’s visceral, literal. My experiences using them and watching them transform my family’s work permeated my time building Puppet. These power tools aren’t little plugins to expensive frameworks, they’re large capital investments that dramatically change your job.

I grew up building houses with my dad. The worst task he gave me was trying to paint a set of louvre doors for a closet while in high school; I had to flip the doors over every 90 seconds to catch drips getting through the slats. After three days of misery, my father relented and rented a paint sprayer, with which we finished the job the same day, at a much higher quality.

Around the same time, my dad would rent a pneumatic nailer for big framing jobs. By the time I finished college a few years later, that critical tool went from borrowed to owned and traveled everywhere with him. Initially used only for large jobs, most contractors now have multiple nail guns to cover framing, trim, and every other use case, and the air compressor needed to power it is as important as electricity.

It might not be obvious, but both of these are examples of automation. You replaced a very manual process - applying paint, or nailing things together - with a machine. If this were a factory, these days you’d call those machines robots, but because it’s a construction site, we just call them tools.

And these tools were expensive. Even with how much faster we finished that painting job, I expect it cost more to rent the sprayer than to finish the work manually, because of how little he was paying me. (This does ignore the soft costs of listening to me complain, which were likely high.) Even today paint sprayers and nail guns are often rented rather than purchased, because good ones cost a lot of money and aren’t needed all the time.

It’s no surprise that discussions of tools and productivity are easier to understand from my experience as a carpenter than as a sysadmin. There’s plenty of room for arguments about what is or is not a software power tool, but when it costs more than a week’s wages, it trails a bright orange cord everywhere it goes, and it can nail your hand to the wall while you’re standing at the top of a ladder¹? It’s a power tool.

There’s a common story about what robots and automation do to people like my dad (and both of my brothers, who followed in his footsteps): It steals their jobs and ruins their lives.

What utter poppycock.

If you think of your job as driving metal spikes into wood, then a nail gun is a mortal threat. But if this is your value add, your biggest danger was never automation. My dad never sold his ability to join raw materials together quickly; he sold homes, he sold the opportunity to enjoy your house and family more. How did these new power tools affect that?

They were awesome. Painting and nailing are classic examples of menial, low-value work, and yet we spent most of our time on them. All of the differentiation we offered to our customers was packed into a narrow slice of work, because implementation took so much time and money. As we were able to bring more powerful tools to bear, the menial work shrank and larger portions of our time could be spent on design work, customer interaction, and tuning our customers’ homes.

Interestingly, my father’s next career step was even more pointedly about experiences enabled by tooling. He took a job with a state hospital in Tennessee, fabricating custom furniture for severely disabled patients. Suddenly he was using industrial sewing machines for upholstery, and partnering with medical professionals to design multiple beds for each patient, enabling them to be happier and more comfortable (and also avoid bed sores, thus saving hundreds of thousands of dollars per patient). Given the tragically minimal budget allocation for this kind of work, every dollar saved through automation and tooling directly delivered health and happiness to his patients.

It’s no wonder I see the value in power tools, that I am more conscious of the benefit they can deliver than the loss of low-value menial work.

I had a similar experience as I was building Puppet. I would meet executives and salespeople (I don’t know why it was always them) who would say, “Oh, automation? Great, you can fire sysadmins!” No. Beyond the obvious reality that I was selling directly to my users, who would never buy on the promise to fire their coworkers, that was just not why we were valuable.

Puppet gave people a choice between lowering cost but keeping the current service quality, or keeping your costs flat while providing a much better service. “Wait, making things better is an option? I didn’t know that!” Most companies were aware that their IT sucked, but they only knew how to measure and manage cost, so that’s what they did. Once you believed in the power to make things better, power tools turned out to be great investments for both the user and the buyer.

By letting people spend more time on the parts of their work they enjoyed, the work that makes them special, we also delivered higher quality experiences for their customers and constituents. “Spend less time firefighting and doing menial work, and more time shipping great software.” If the heart of your skillset is clicking buttons or responding to outages, Puppet might have been a threat to you, but our users knew where their real value was. We helped them spend more time there and less time on the boring, low value stuff. The sysadmins hated the work, the customers hated to need it, and the executives hated paying for it. Great, done, don’t worry about it.

When you look around the software market, though, power tools are out of style. There are big data companies building for the non-existent average user, minimalist companies building solutions that do little for almost everyone, and there are power tool companies of yesteryear still hanging around. There just aren’t that many modern software companies building large, clunky, expensive tools that just might cut your hand off if you’re not careful.

That’s partially why productivity has stagnated². The world has not changed that much - some of the greatest improvements to productivity come from making large capital investments in tooling for your workers - but how we spend our money has. People balk at a $5k computer, when the Mac IIci would cost more than $13k in today’s dollars just for the hardware, yet was a powerhouse in desktop publishing. This is to say nothing of how the mobile app stores have driven down what people are willing to spend on software.

Yes, Adobe’s software is expensive, but it’s that price because it delivers so much value. If it didn’t, no one would buy it. Every large market should be so lucky as to have the collection of power tools that graphic designers get. It sounds crazy, but we’re suffering from not enough expensive software. Instead of building the most powerful software possible and finding customers who see its value, companies are building the simplest thing they can and trying to get everyone to use it.

There are bright spots in the industry, like Airtable and Superhuman. I’m hoping they help to shift momentum back to automating away the tedious work and enabling focus on what humans excel at.

More powerful tools improve your life, but they also make you happier even if you can’t buy them. They tantalize you, promising you great returns, if only you can come up with the cash. And they’re maybe just a little bit scary, warning you that buying them is not enough. You must master them.

A friend of ours managed to do this when working alone in the time before cell phones. ↩
Yes, I might be being simplistic to make a point. ↩

The Market Is Wrong About Your Problems

luke@lukekanies.com (Luke Kanies) — Tue, 17 Apr 2018 00:00:00 +0000

What Voltaire and the Flaw at the Heart of Economics Have to Teach Us About Software That Doesn’t Exist

Voltaire’s Candide juxtaposes an optimistic philosophy with unbelievable tragedy. He was angry at the 19th century philosophers who proclaimed that we lived in the best of all possible world while destruction and death unfolded around Europe on an epic scale.

We might hear the claim that we live in the best of all possible words and scoff. Of course, we’re too enlightened to be such naïve optimists. But are we? Isn’t the belief tempting? Or even, doesn’t the behavior of those around you make more sense if you realize they believe this, at least a little bit?

Economists are theoretically rational, analytical, big picture thinkers, but at the root of modern economics is a belief shockingly close to Candide’s parody of optimism. They have what they call “The Efficient Market Hypothesis” (EMH), which roughly states that all assets are valued fairly. This is built off the idea that asset values in an open market are fair because they include all available information, and all the actors in that market are behaving rationally in regard to both the asset and the available information.

This theory tends not to trigger the cynicism that Voltaire does. Intuitively, it sounds not just right, but defined as so. Isn’t an open market essentially a mechanism for finding the fair value of an asset? It’s not so simple. And when it goes wrong, it does so spectacularly.

Modern economists cannot be as destructive as the great thinkers of the 18th century, whose big ideas justified eugenics and many other horrors. Just because they cannot as easily be used to justify mass murder does not mean they should not be accountable for the downsides of their obviously incorrect theory.

“No”, I hear you say, “the EMH is not wrong; it’s correct by definition.”

Economists have convinced us of what Voltaire was protecting us from: We live in the best of all possible markets, where all information is public and all assets are fairly valued. If the market does not value something, that it must actually be worthless.

But of course, if that were true Warren Buffet would not have become a billionaire buying stocks that were worth more than the market was paying, the finance industry could not have been built on advising clients about public stocks, and you’d have no need for lemon laws or other regulations that fight information discrepancies. Nor would Kahneman and Tversky have won the Nobel Prize for demonstrating that actors in an economic system behave anything but rationally, puncturing the EMH for good. Thankfully, this has forced the field to begin to grapple with its flawed underpinnings, but many modern beliefs are implicitly built around these bankrupt theories.

You might be patting yourself on the back right now for not being silly enough to draw Voltaire’s ire, but it’s baked into the value system of the world around you, especially if you live in the US.

The market moves from irrationally ignoring new technologies like the blockchain to irrationally dumping money on them, without any fundamental change to justify the shift
Investments are made based on proximity and serendipity rather than rationality and opportunity size
We tend to claim that the rich earned their status through hard work, rather than recognizing the role of privilege, inheritance, and luck in their status

Of course, not everyone in the market operates with such optimism, but each of us is biased in this direction. It affects our thinking whether we want it to or not.

“Ok”, you say, “even if I accept some people make optimistic investment decisions, what does that have to do with software?”

Great question. If we live in the best of all possible markets, where all information is public and all assets are fairly valued, then we can trust the market’s assessment of what software should and should not exist. Lack of software to solve a problem is a sign that it’s not worth solving.

If, on the other hand, our world could be better, or if our market is imperfect at valuing assets, then we can’t trust intuitive conclusions about where value resides. This is most true when it comes to valuing unsolved problems. It might be that a given problem has no solutions because it is not worth solving, but mundane reasons are more likely to be at fault.

Most great companies exist because they provided something the market did not know it wanted. Their founders encountered a flaw, and managed to build something great in the opportunity created by it. Henry Ford claimed if he’d have given people what they wanted it would have been a faster horse. The market knew how to value them, but not cars. Before Apple, the market did not value personal computers. Before Google, the market valued directories but not search engines. Before the iPhone, the market valued expensive phones for professional use but not personal.

These value statements were market failures, and their resolution generated billions of dollars for the companies resolving them. Now, of course, the market sees great value in what these founders have created, but not because the market is so smart; it’s because it can no longer fool itself.

It’s easy to grow despondent in the face of such obvious market failures. If the wisdom of the crowds, the great invisible hand of the market, can be so wrong, what hope does a lonely entrepreneur have? I take a different way.

I luxuriate in these misses.

They surround us. We bathe in them. Yes, many great companies have grown into critical market gaps, but even with all these successes, there are untold problems whose solution should be valued but is not.

Only once you reject the market’s flawed opinions about what matters, you begin to see nearly limitless opportunity. There are so many more unmet needs than there are perfect solutions. These are your opportunities.

Of course, just because the market dismisses a space doesn’t mean there’s a great opportunity there. It’s your job to know the problem, your customer, your user, your buyer well enough to draw your own conclusions, to develop enough certainty that you don’t need someone else to tell you what to believe.

Because that’s the real point: Trust yourself, not a bunch of paternalistic optimists.

Owning my writing

luke@lukekanies.com (Luke Kanies) — Fri, 13 Apr 2018 00:00:00 +0000

It’s the message, not the medium

I did more writing in 2017 than I ever have before, probably more than I had done in my entire life. I stated at the outset my desire to write in order to learn, and publishing regularly has delivered. More importantly, it forced me to capture and share many of the results of my R&D. The writing topics were primarily venture capital, the software startup ecosystem, and founder optimization, but one of my weaknesses is a drive to the meta, spending time on the tools and systems rather than the work itself. Unsurprisingly, this ground is as fertile in prose as it is in code.

I have done all of my writing on Ulysses, which has been a good tool. I do miss much of the power of Vim for managing text, but the usability trade-offs are usually worth it. Plus, Vim is not exactly strong on wrapped text. Ulysses’s most important capability for me is that it transparently syncs between my phone , both of my iPads, and all three of my computers (yes, I know). I can open any document on any device with no worries (given my iPads are on LTE, and thus can always download updates). Second to that is the ease of getting data out. I was able to text a 5k word document directly from Ulysses on my phone to two different people, because it converts anything to PDF and can send out via the share sheet. It publishes directly to most platforms, so I used it to post everything to Medium. I do wish its backend storage was more visible, so I could version control everything in git, but you can’t have everything.

The only time I ran into troubles was publishing my travel writing - I was copy/pasting photos from Apple’s Photos app into Ulysses, then publishing into Medium, and it turned out that no part of this process downscaled the photos, meaning each was about 20MB. This is fine when you’re on solid wifi, but not so good from a campground in Yellowstone. The primary reason I did not write during the second month of my trip is it was just too painful to publish. Ulysses really fell down here, because when it works, it works great, but when it fails it is miserable. I’d just sit and stare at my iPad for ages, with no visibility of failure or success until the very end, and it would often manage to upload the text but not the photos. The only fix for this was to delete the draft from Medium and try again. Not so great.¹

Over the year I became concerned, though. I heard about Andrew Chen, who built a following on successive publishing platforms (e.g., Blogger), each popular and well-funded, only to have the companies disappear (because that’s what Silicon Valley does to most companies). He eventually realized that the only way to consistently reach those who were interested was via email; it’s never going away, subscriber lists are easily portable, and of course everyone knows how to use it. He had to move from letting a platform own his audience to taking control directly, and email was the only real way to do that.

I think Medium is pretty good, and at least for now it has no shortage of funding. Even last year, though, it made well-publicized efforts to retool its business, a clear sign that whatever it was doing before wasn’t working. It seems unwise to bet that a follower on Medium will have any meaning in a few years.

It just so happened that I ended the year with an experiment in their new business model. My series on Venture Capital, in partnership with NewCo, was published behind Medium’s paywall. While the experience was positive overall, and I got paid more for those pieces than I have for, um, all of my other writing ever, earning money isn’t my real goal in writing. Yet, paying writers is exactly what Medium has to figure out in order to attract the content and audience it wants. I appreciated the extra attention working within their paywall provided, but I came out thinking it’s unlikely to be the right path for me in the long term. My goal is to maximize the reach of my writing, and it’s more about the arc of all of it rather than a couple of heavy-hitting pieces getting the most attention, which means our respective goals are orthogonal at best, and in direct conflict at worst.

While I have not written about it, I spent a lot of last year fascinated by email, inboxes, and how we consume content. I’ve been a deep fan of RSS from the Bloglines days (Unread is my reader of choice these days), but RSS is mostly dead (thanks, Google!). The kinds of sites that produced great feeds back in the day grew too big for a hobby. They became either wildly profitable for a small team and thus got destroyed with ads and shitty content (hi Boing Boing!) or people had to back away because it was just too much. Mainstream publications like the NYTimes might still publish RSS feeds (I literally have no idea), but RSS is a poor fit for how much content they produce.

When I look around, it seems that the RSS feeds of ten years ago are now awesome newsletters. See how often your favorite sites talk about their newsletters vs their feeds. I’m pretty confident I’ve never heard a podcast ask me to sign up for a feed, but many casually mention their newsletters. (Well, to be fair, podcast feeds are just RSS, so in that sense it’s survived, but I think we can agree it’s a very different use case.) The market has moved.

This shift is not all peaches and cream. The superiority of email as a publishing mechanism has not brought with it a superior reading experience. Long form content from writers I follow does not belong in the same inbox as requests for coffee meetings, yet that’s where we are. (I asked the Feedly CEO if they would please please add newsletter subscriptions to their platform, and he could only say they were considering it. If you want to build the newsletter reading app, hopefully with an index of great letters to subscribe to, count me in as an early contributor.)

Even with its downsides, I’ve decided to move my writing to my own site via a newsletter-first publishing model. From now on, everything will be published first to that site and the newsletter (sign up now!). There will be exceptions, when publications offer enough exposure that I give them some period of exclusivity. I will also indefinitely duplicate each piece to Medium on a delay, to take advantage of the audience I already have there.

There are enough examples out there that I’m pretty confident this is the right long term answer, but it’s early enough that it feels like an unstable experiment. Like most, I love and hate email, and I am a bit bummed about the extra infrastructure involved in this system.

If you’re still an RSS person at heart, you can always just subscribe to the feed, and if Medium is your bag, at least for now you’ll be able to see everything there, too. Of course I can’t promise how this plays out in the long run - else it would not be much of an experiment - but you can bet I’ll work hard to find the right way to talk with the people most interested in what I have to say.

One note before I go: I could not have made this transition without the help of Mike Julian. He helped set up each of the services, mediated the hiring of a consultant to modify the site, and connected all of the services together. He’s got a great book on monitoring, and is available for consulting on monitoring and observability. I can’t recommend him enough.

Thanks for following on so far. I’m excited about another year of writing.

It’s worth noting that Apple’s iCloud Photo Library did wonderfully here; I could upload every photo to my iPad, and it would sync when it had good data, and sit quietly when it did not. I love asynchronous protocols. ↩

Abandoning Trello

luke@lukekanies.com (Luke Kanies) — Fri, 06 Apr 2018 00:00:00 +0000

On the value of change and focus

I have been a passionate advocate of Trello almost since the day it came out. Visualizing the work is incredibly powerful, and its use of priority by ordering is so obviously better I could not imagine using anything else. I have brought Trello into companies, and caused hundreds of people to use it. Recently, though, I stopped using it in key functions, moving my personal tasks into Things and other work into the applications that own it. It started as an experiment, but quickly snowballed into a full transition as I realized how much better it would be for my core use cases.

I am a productivity junkie, from GTD to Deep Work, and while I know the tools aren’t the work, they’re one of the fastest and easiest ways to change a system, bringing new perspective and abilities.

I initially adopted Trello for managing my personal tasks. From there, it slowly spread to group and company use cases, and by the time I left Puppet in 2016 it was baked into our core business operations.

I had considered switching away from it for my personal tasks a few times, because it’s been obvious for years that it was not a fit for how I managed and processed my life’s flow of work. Where I had always taken great pride in my productivity system, I could no longer muster the discipline it required, which meant it was extraneous process and I was also failing to do my job. I sank so low that I began sending person to-do items to my inbox. shudder However, my life as CEO was busy, yet not really built around task execution, so it was never worth the cost of the tooling change. Or so it seemed.

While I abhor tooling changes for their own sake, sometimes you just have to experiment, and when I had a run of open space I decided it was time. Even if other places were worse, I was better off spending time elsewhere to get out of my funk than I was continuing to stare at this board that just wasn’t working for me.

As I looked to move away from Trello, I wanted to switch to OmniFocus, but the timing is wrong. I recently downloaded the current version, but it reminded me why I stopped using it years ago: It asks too much of me¹. The biggest disconnects were the need for contexts, and the inability to set priority by dragging items around. It looks like the impending next version will be a great compromise for me, but I can’t use it until it arrives.

As I began moving tasks into Things, I was slowly reminded what it was like to have my task app be, well, an app. Before Trello I used Asana, at a time when its mobile experience was just a badly packaged web page. It’s been years since I had the pleasure of working with someone who bothered to build for the platforms I used. What a difference it makes.

Processing this small but meaningful change took over my brain for the rest of the day. I could not let go of the transition, but I also could not stop thinking about its consequences. “Thinking” is being too generous. I had not seriously looked outside of Trello for years; all of my habits and instincts are built within its constraints, its physics model. That meant wide open opportunity to construct whatever world I wanted, but also the need to do so, and embarrassing mechanisms for getting in and out. Creating a quick task in Trello is most easily accomplished by sending myself an email, which tells you how seamless the core experience really is. Telling Trello of work to be done in another application usually required custom applescripts to connect the two (e.g., creating message:// urls).

The keyboard’s change in utility keeps hitting me. I did not realize how rarely I used Trello shortcuts for their sheer disagreement with my hands. Well, partially, they were insane - ‘c’ archives cards, where I kept thinking it would create them, and repeating mistake kept my hands off the keyboard - but also, they were just different. I keep visualizing myself sitting at Things, fingers poised over the keyboard, in a world that makes sense to me. It’s pleasant.

I have a lot of work in Trello. Basically everything I’ve recorded in the last 4 years about what I could or should do is there, and it’s been the platform for organization all of that information. I’ve always been pragmatic, so even when I built it I would not have said it was the “best” answer, just that it worked at that time for my use cases.

Now I am questioning everything I’ve done recently - not to ask if I’ve made a mistake, just wondering what the world would look like if I had done that work differently. Are there projects languishing from sheer friction, that would suddenly become easier if migrated?

The answer in at least one other case is ‘yes’. I had a Trello board for managing all of my writing ideas, and I had a standard right-to-left workflow from idea to writing to done. I just never really used it. Instead, I did all of the management of writing in the same place I did my actual writing: Ulysses. I built a workflow from folders² instead of lists³, and eventually I realized that the Trello board was hurting, not helping. The ideas I put in there languished, and Ulysses is just as good at capturing a sentence or two about a post as it is for writing the entire thing. The board is now closed, and my writing is in the same place as all of the work needed to manage it.

Tools do not make the difference, but tools can make a difference. A thing can go from undoable to tractable with a small change in tools, just as a math problem can go from impossible to trivial if you flip the equation around a bit.

I know Things won’t work for many of the use cases I have in Trello, partially because it’s so obviously a single-person tool, and much of my work does not have a home I can move the organizational work into. E.g., I have a list of lists in Trello of all of the day trips I could consider taking around Portland, and I can’t think of where I’d move that. I don’t know where those other problems get solved now. Maybe they don’t change.

But I know my standards have been reset. I know I made a mistake letting myself sit in one tool for years, unhappy but unwilling to invest in the change. It’s a wonderful feeling to be looking at the world through new eyes again.

To be fair, I also stopped using it in the days when it took 45 seconds to open the app on an iPhone, because that’s how slow the data synchronization was. ↩
Which they call ‘Groups’. ↩
Really, are they any different? ↩

Great design is ruining software

luke@lukekanies.com (Luke Kanies) — Tue, 03 Apr 2018 00:00:00 +0000

The arrival of the smartphone has convinced the world of the value of great software design, but it’s not all good news

The smartphone has reached more people and delivered more value faster than any technology ever seen. Much of the world has had to adapt to this arrival, but software design suffered the greatest reckoning. As the smartphone ascended, developers finally adopted reasonable design principles, realizing that they could not pack every feature ever seen into the smartphone experience. This recognition of the value of design - and especially, minimal design - is a good thing. Mostly.

I could not be happier that the industry finally accepts that there are principles of design, and there is a practice and discipline behind building great software. It’s great that we’re seeing more focused software that does little, but does it very well, rather than the previous age of the GUI when software attempted to own large parts of our lives by doing anything and everything. For a long time, Microsoft Word was used by nearly everyone who had a computer, and their strategy was to ensure no one ever had a reason to choose something else by building every feature anyone might ever need; their toolbar was the canonical example of never saying no.

The smartphone changed all that. Those rows of icons would fill the screen on a phone and leave no room for typing, and of course, no one would use them anyway because of how different the usage patterns are. As people realized they could no longer just throw in the kitchen sink, they began hiring (and listening to!) actual designers, and those designers have been steeped in the culture of Dieter Rams and the minimalism of the Bauhaus movement, which is awesome. Mostly.

Unfortunately, the phone caused everyone to focus on the final design principle of Dieter Rams (“Good design is as little design as possible”), without apparently remembering the nine that came before it, or why they were earlier in his list. I get it; the design constraints in a phone are intense, and it might not be a good idea to minimize everything, but it sure is easy.

The consequence of this mobile brutalism is a new movement building simpleton tools: Software that anyone can use, but no one can become an expert in.

Trello is a great example. I adore Trello. I think it’s great software, and it’s clearly a success by any measure. However, for all that I’ve relied on Trello daily for years, I feel no more an expert than I did just after starting to use it. It’s not because I haven’t tried; it’s because there’s no depth. You can pretty much plumb the product in a couple of days.

That’s fantastic for getting new users up to speed quickly, but deeply frustrating after a couple of weeks. Or months. Or years. Compare that with Vim, which I still use for all of my code editing, yet it’s so complicated that most people don’t even know how to quit it, much less use it. I’m not going to claim its lack of user friendliness is a feature, but I will defend to the death that its complexity is.

Apple’s Notes is the ultimate expression of this trend in text editor form. It’s a fine text editor. I know some people have written huge, impressive programs in similarly simplistic editors like Notepad on Windows. But I personally could not imagine giving up keyboard navigation, selection, text munging, and everything else I do. The fact that complicated work can be done on simplistic tools speaks to the value of having them, but in no way invalidates the need for alternatives. Yet, on the current trends, no one will even be trying to build this software I love because they couldn’t imagine two billion people using it on a smartphone.

I think it’s fair to say that that’s an unfair standard, and even a damaging one.

I miss the rogue-esque exploration that tool mastery entails. It’s not that I want tools to be hard; I want them to be deep. I want to never run out of ways to invest in my tools. I don’t want to have to swap software to get upgrades, I want to upgrade my understanding instead.

But I look around my computer, and everything on it was designed for the “average” user. I was not average as a CEO with 40+ hours of meetings a week while receiving more than 200 emails a day, nor am I average now as someone who spends more time writing than in meetings. There’s no such thing as an average user, so attempting to build for one just makes software that works equally poorly for everyone.

It is a rookie mistake to conflate the basic user who will never plumb the depths of their tools with the expert user who will learn every nook and cranny of your software. It is a mistake to treat the person who sometimes has to solve a problem the same as a person who spends 80% of their time working on that problem.

I don’t want to be an expert in all of my tools - for all that I take thousands of photos a year, I don’t think I’m up for switching to Adobe Lightroom - but for those tools that I spend the most time in, that most differentiate me, I want the opportunity for true expertise. And I’d happily pay for it.

Back in the days when computer screens were tiny, there were plenty of stats that showed that paying for an extra screen would often give people a 10% or more boost in productivity. I know it did that for me. As a business owner, it was trivial to justify that expense. Monitors cost a lot less than 10% of a person’s salary, and don’t need to be replaced every year. Heck, the whole point of the automation company I built was to allow people to focus their efforts on the most valuable work they could do.

Yet, when it comes to software being built and purchased today, to the tools we use on a daily basis, somehow our software ecosystem is failing us. There is no calendar I can buy that makes me 10% better, no email client available that I can spend five years getting better at.

It’s great that people are finally making software that everyone can use, but that’s no excuse to stop making software for specialists, for experts, for people who could get the most advantage from that extra 10%.

Please. Go build it. I know I’ll buy it.

Where does your work live?

luke@lukekanies.com (Luke Kanies) — Tue, 13 Mar 2018 00:00:00 +0000

Most of our software is confused about what job we’ve hired it for

I’ve really enjoyed playing Zelda: Breath of the Wild, but my life has been changed more by one of its reviews than by the game itself. The review had a unique view on what made the game so great. It contrasted Zelda to other games - Destiny, for example - saying that while others tended to distribute gameplay across multiple areas (e.g., in Destiny, the radar is a critical part of the game), Zelda really focuses the game into the main screen where you walk, glide, ride, and fight.

The review (which I unfortunately cannot find, because of the quantity of posts online that all use similar words) called this “where the game lives”. I love what this phrase evokes. I absolutely loved the game Borderlands, but I was deeply frightened of ever finding out how much time I spent at its store screen, because item collection and management was such an important part of the game. A lot of its fun was specifically from the collection, rather than the playing, but that meant a large chunk of the game lived in the store, as opposed to out in the world.

Most of our software could use a similar dissection.

Like Destiny and Borderlands (which are both great, and quite similar), the tools we use show a surprising distance between what they help us do and what we’ve hired them for. If I may be permitted to steal from this review, this distance is a sign that our software is confused about where our work lives.

To pick a counter-example, I’m writing this post in Ulysses. People who choose this software laud its simplicity, which makes it easy to focus. What they really mean is, all you can do with it is write. There’s almost no formatting, very little organization, very little anything but writing. The work lives in the writing. (My first draft was written on an ipad, which further simplifies that focus.)

Contrast that with any task or project management tool. My wife and I are in the middle of planning a bunch of camping, and we’re using Trello to organize many of the options. What is Trello’s opinion about where the work lives?

Last time I looked, my wife had three browser windows open, each with about fifteen tabs. She’s also working in RoadTrippers (Pro, natch). To get this work into Trello is a process of copying, pasting, writing copy about why you pasted it, and then using Trello to file it so you can find and manage it later.

In this operation, where does the work live? It’s scattered across maps, calendars, browsers, and applications like RoadTrippers. Does Trello know that? Does it agree? How does its opinion of where the work lives affect its utility? Brief introspection leads us to conclude Trello has no idea where the work lives, and the humans using it are entirely responsible for connecting the two.

Here’s a simple exercise for anyone using a task tracking app: Envision yourself going into that app and just marking everything done, even though you obviously haven’t done the work. It hurts to even consider, doesn’t it? Your brain has absorbed that these tasks are representations of work, and it’s your job to match the representation to the work, because you know the tool won’t do it for you. When you mark something done, of course nothing goes out and does the work; you’re just lying to your software about the state of the world. And it has no idea! This disconnect is what leads to an allergic response to the idea of marking work done in software that is not yet done in the real world.

I’d like to say that Trello was just a bad example, but I think all task tools share this confusion. Bug trackers and project management tools are specialized examples of this, and they obviously have no idea where the work lives. If I’m writing code, all of the work is done in my text editor, in files on disk, and maybe in my testing tools to ensure the work is done and done right. I then go somewhere entirely different to mark the work done. Why? Shouldn’t GitHub know it already? Why do I have to explain it? The answer is because these trackers think tracking is the work, when of course, the work is the work.

It’s no better in personal tools. I just started using Things 3 for my own tasks, nearly all of which end up being expressed in email or calendars, yet Things 3 has no conception of either. It has no idea where my work lives, and expects me to put out all of the effort necessary to connect them.

Speaking of email and calendars, they have their own role in this conversation.

Email is interesting. Everyone hates it, because it’s so important to everyone that we use it constantly, yet this animosity is a result of its utility and criticality. In other words, people hate it because it works so well. But when you’re doing email, what work are you actually doing?

I’m not sure I know. You’re communicating. But usually, you’re communicating about some other kind of work, like a document, a meeting, or some kind of activity that takes place outside of the inbox. A well designed application will remove the need for communication via email - Google Docs is a great example of this. Its sharing and commenting features have allowed many discussions to move from email to where the work is, in the document itself; their addition of suggestions has doubled down on focusing on the work, rather than talking about the work. (Note that this is completely different from Slack, which advertises that it gets rid of email, by which it means it moves the conversation, not that it does a better job of bringing the work into the software.)

Of course, how do you have Google Docs tell you someone commented on your document? Email. :)

What about calendars? Why do calendars exist? As a tool, where does their work live?

I am thankful to have had to try to explain to a friend my position on this, otherwise I’d think it was easy to understand. It’s so counter to how people work today that a relatively obvious truth is impossibly counter-intuitive: calendars are about how I spend my time.

When using a calendar, the work is what you actually do. You, a person, out the in the world. That’s what the calendar is about. Its job is to ensure you do the right things at the right time, with the right people, in the right place. It’s about doing, not documenting, managing, or notifying. You can put something in a calendar and not do it, or do work that’s not in the calendar; any of us would say, obviously, that it’s what you do that matters, not what the calendar says. Merely creating an event has no effect, and thus no value; it only matters if it then affects your behavior. The work lives in what you do. But does your calendar make even the slightest attempt to directly manage how you spend your time? What would that even look like?

To pick a small example, my calendar apps seem to not care what city I’m currently in, or where I’m physically located. Isn’t this weird? The tool whose primary job is to manage where I am physically located makes no attempt to represent or take into account the core fact it is meant to control. It still dumbfounds me.

Yes, they can tell me in real time when I should leave for a meeting based on travel time (as long as travel involves driving, rather than walking down the hall to a conference room), but they can’t say, “Given that on Tuesday you’ll be in Portland, working from home, you should block out travel time to get downtown to lunch and back”. That is, they can alert me in the moment, but they can’t do their core job - reserving time to ensure I’ll be doing the right thing in the future. Because they can’t do this, I have to create those blocks myself, else I’ll find myself choosing between skipping one appointment or being late to another. The whole point of a calendar is to manage time, but in this simple example they fail to ensure I will have space to transition my corporeal existence between physical locations. Shouldn’t that be step one, rather than an exercise left to the human?

I also reserve time for tasks I do alone every day, like working out and writing. I do this primarily to ensure it gets done, rather than because those times are special (although I do get a bit jittery now if I don’t write first thing in the morning). There’s no way to explain to my calendar what I’ve actually blocked that time out for, and thus no way for it to respond to whether I’ve done it or not, even though my computer knows if I’ve done my writing, and my watch knows if I’ve worked out. Wouldn’t it be great to see your calendar dynamically rearranging your day because it noticed you missed your workout?

My calendar is confused about what work I’ve hired it to do, and therefore does not know it needs to look in those places.

We’re so used to the idea that our software represents the work that we seem to have lost hope that it will actually help us do it. Most of the tools we use are entirely disconnected from the work they’re supposed to help us with. Marking something done does not do it, deleting email does not indicate communication has happened, sitting at your computer while your calendar says you’re writing does not produce text. The representations are not the work, yet we forgive our tools for only dealing in representations, not actual work.

I don’t know if that reviewer was right about why Zelda: BoTW is so great. I can’t even imagine what all the software I use would look like if it were built around where my work lived, rather than merely being used to model and manage it.

What I do know is that our software can and should be built to help us do the jobs we’ve hired it for. But because it is confused about why we use it, what we do every day is lower quality, less fun, and just downright confusing.

This also shows just how much opportunity there is to improve the software we use on a daily basis.