The European Union and Apple are locked in a fight nobody wants to cede. First was the Digital Markets Act (DMA), which made Apple create an entirely new subset of rules for iOS and the AppStore. And yesterday, Apple was fined almost $2 billion for their anti-steering provision affecting companies like Spotify and Amazon’s Kindle.

All digital purchases on the iPhone must go through In-App Purchases, which involve a 30% commission to Apple (goes down to 15% for long-term subscriptions). While certain services like Netflix and Spotify (classified as “reader apps”) can ditch IAP, the resulting user experience gets weird. You cannot sign up if you download such an app as a new user. And the AppStore rules prohibit developers from even suggesting to their users that they should go to the website instead and start their subscription there.

This is probably one of the most egregious examples of how Apple’s strategy leads to suboptimal experiences on their devices. Apple feels entitled to this tax, which you can clearly see in their statement.

Despite that success, and the App Store’s role in making it possible, Spotify pays Apple nothing. That’s because Spotify — like many developers on the App Store — made a choice. Instead of selling subscriptions in their app, they sell them on their website. And Apple doesn’t collect a commission on those purchases.

Spotify didn’t really make a choice because they didn’t have one. Some companies, like mobile game development studios, can shed 30% of their income because their marginal costs are more or less zero. This isn’t the case for Spotify since they have to give back most of their revenue (which amounts to 74%) to copyright owners (i.e. labels and artists). The same is happening with Books. You can’t buy books on Kindle or Audible on your iPhone because then Amazon would have to pay 30% to Apple. And for any book, there’s already a pre-defined distribution between the publisher, the author, and the seller. Amazon would be losing money on every book then.

One of the main problems with the AppStore fees is the rules don’t differentiate between goods with marginal costs and those without them.

What makes Apple look particularly bad and should have motivated this case is the fact they operate competing services in the face of Apple Music and Books. And Apple doesn’t have to pay themselves 30%. So, they enjoy better economics and a better user experience since you can sign up right away. One could build a legal case that Apple is extending its monopoly power from one industry to another, which is prohibited in most major jurisdictions.

The Digital Markets Act has many provisions. Apple carefully crafted such a response that most developers would not even dare to use the updated EU regime. They did open certain things, like access to the NFC chip, and later, they removed some of the limitations. However, they still want to control the overall experience and charge money.

In my opinion, this is indeed a case of an unstoppable force facing an immovable object. And it gets ugly. The European Union shouldn’t make tech product decisions. What is even worse is that most EU regulations are written in a particular way. Like with the infamous GDPR, businesses have to guess what exactly they need to do for the government and regulators to assess whether it’s compliant. It’s also noticeable that the EU’s fines are getting arbitrary by this point. Writing a big number because Apple is a wealthy company and simply saying “the tech giant’s terms were “unfair trading conditions” without providing clear guidance on what exactly you want them to change isn’t a great way to regulate.

And Apple should see a writing on the wall by now. The longer they hold on so profoundly to their entrenched position, the worse the outcome will be for themselves and their users. The company had an easy way out: let all developers share a link to their website instead (or in addition to) using an IAP. Lots of developers would have likely stayed with the IAP just for the sake of conversions alone. Most (over 70%) of AppStore revenue is coming from games. A mobile game likely won’t suddenly ask you to go online, set up an account and buy some gems there because it will be afraid of losing a potential sale.

Of course, some companies might prefer this approach anyway, especially if they have the brand power to pull it off. Epic Games’s Fortnite is probably the best example (if it was allowed back in the AppStore). Tinder would also use this, and dating apps surely drive a significant part of AppStore revenue as well. But most games and apps aren’t like that. Such an approach would make things easy for businesses selling goods with notable marginal costs. And most importantly, it’d provide a better user experience for the users.

Apple can talk a lot about how their system provides safety, but they have no problem with you giving your credit card to Uber right in the app. And what’s actually the difference?

The current system creates perverse incentives for Apple and forces the company known for building great products to provide subpar experience. Even Apple might be better if they get off the needle of AppStore fees. When Tim Cook provides an update on the “Services” revenue growth, he wants you to think about AppleTV+ and Apple Music. Yet most of this revenue category is provided by just two things: AppStore fees and Google’s default search payment. And none of this makes things better for actual customers.

I support sideloading, and I don’t believe Apple should ultimately decide what software I can run on my own device. This limits innovation and puts them in a position where they can be forced to run censorships for authoritarian governments, just like they had to remove VPN apps from the Chinese AppStore.

But I also understand that one of the reasons iOS has a thriving app ecosystem is the lack of alternatives. If you have an Android device, there are countless websites and forums filled with cracked apps you can install immediately.

Instead, Apple might see governments worldwide legislating their product experience, and the result will likely be far worse.

Most politicians are populists, which is the natural result of the basic rule of communications: the larger your audience is, the simpler your message should be. And with politicians specifically, there’s a straightforward line from the size of their following to their actual power.

Politicians are incentivized to find a slogan that resonates with people and run with it regardless of their personal opinion on the matter. As an off-topic, I doubt certain US Republicans have a significant issue with LGBT themselves, but they adopt the message that works for people who can vote them in (or out), however cynical this might sound.

The same is happening to AI. And it’s accelerated by AI becoming a major trend covered by practically every media publication. Not only most have dedicated AI writers, but there are entire outlets (e.g. VentureBeat) that have largely shifted their focus to AI.

And sometimes, they’re just broadcasting the opinion of crazy people like Elizier Yudkowskiy, who isn’t an expert in any modern area of AI. He’s a self-proclaimed expert on “AI safety”, which seemingly means regurgitating ideas from sci-fi novels with specific outlooks to convince everyone we’re doomed. Balanced opinions are complicated, and slogans are easy, which is why both doomers and proponents of AI (i.e. “e/acc” movement) dominate the discourse even though all practical discussions are somewhere around the middle (and should be happening in a completely different plane).

Whether Biden or Sunak actually believe AI is dangerous is irrelevant (although Biden might have indeed been spooked by an underperforming action movie). If politicians think doing something publicly will help them score, they’d do this. OpenAI, Anthropic, Google, and all others will be the first to tell you they support strict regulation of AI precisely because this will help cement their hard-earned position at the forefront of the industry.

There are copyright and safety questions, but all practical concerns fall into a completely different bucket than what pundits say. Generative models won’t drop a nuke on Los Angeles (“The Creator” is a great movie, though), nor would they automate everyone’s job. But they raise the same old problem of algorithm-based decision-making and pose a new problem that doesn’t map well on our current copyright laws (both in the letter and the spirit).

Safety

Algorithms have been used to make decisions affecting people’s lives for decades. Sometimes, they’re basic; sometimes, they’re pretty advanced. Credit scores, mortgage assessments, and background checks aren’t manual but run by algorithms.

The actual problem worth discussing is the potential of inherent bias AI might ingest from the training data and negatively affect someone’s life while obfuscating the process.

Old OCR algorithms used to recognize printed texts were highly complicated and cumbersome and relied on computer vision and advanced math. We use AI to solve specific complex problems differently and abstract away the solution when it’s too complicated to build. We use data to train more-or-less generic networks and then run primitive arithmetical operations many times, ultimately providing good results we wouldn’t achieve through classic algorithms.

Because of this, most modern AI networks are essentially black boxes. You know the input and the output, but you don’t see how the decision was made, and it’s challenging to dissect the model while it’s “thinking” to understand why.

So, if a financial institution uses AI for credit checks and fraud assessments, one could imagine a scenario where flawed training data would lead it to discriminate by race or other parameters. And since it’s a black box, only long-term statistical observations would allow us to see the problem, though most likely, the people in charge would claim the discrepancies are accidental.

This problem is more tedious but is way more accurate. AI won’t do it because it’s terrible. It’s emotionless and doesn’t have a goal. This is a popular trope in sci-fi, but I don’t believe Artificial General Intelligence could be a cold, emotionless beast. Emotions give purpose, which is why ChatGPT doesn’t think anything until you tell it to. It’s simply not there yet. What we have now is way more basic.

Copyright

Neither large language models nor image generative networks fit well into our copyright frameworks. The line between plagiarism and inspiration was always blurry. All human artists, including writers and painters, learn by observing the works that came before them and then produce something of their own.

Vanilla Ice used a guitar riff originally composed by Queen and David Bowie. He then claimed he added a beat between the notes and that the original melody was different from his. It was ultimately decided that this was not the case. Ultimately, he had to pay up, but only because it was too transparent. Musicians get inspired by others’ music all the time.

Generative networks aren’t too different from humans in this regard. But since this is machine intelligence, they can do this much better, at scale, and then provide everyone with a quick and easy way to create pieces that might copy someone’s material too directly.

Writers like George R.R. Martin claim that OpenAI’s GPT4 was trained on their material, which could very well be correct. Before, we had a simple delineation. A writer consumes existing material and hopefully uses it to write their own Song of Ice and Fire. Nobody just starts writing one day without reading a single word imagined by others.

If you use others’ material too directly, we call it fan fiction and mainly don’t pursue it as long as you aren’t trying to sell it. Then it’s illegal.

But the ultimate use case of GPT4 is not someone using it to retell some author’s book but to write new stories under a user’s command. Yet the reason it’s capable of doing so is all the writing that was consumed during the training stage. So, does it break the copyright?

Generative networks are stuck between humans and plain computers, and until we develop new frameworks and the common law system in the US and the UK create precedents, nobody is sure what to do.

***

Now, the emergence of generative networks might have already affected the job market globally. As usually happens with technology, the biggest threat is to the low-level contractors, such as people who accept $5 orders on Upwork since they’re based in a cheaper (and poorer) country.

The scandal around the intro to Marvel’s Secret Invasion is a perfect illustration. The VFX people working on it used purposefully poorly-made AI-generated images due to their Uncanny Value quality relevant to the story. Half of the Internet reacted as if the producers fired everyone and went to write the prompts themselves (and manually did all the VFX on top to make the animation, I guess).

In fact, actual commercial writers, designers, and other content creators were the first to start using tools like Stable Diffusion and MidJourney in their work. A game development company I know uses these tools to accelerate its image pipeline. This specifically helps designers spend less time on mundane things. For them, AI hasn’t replaced a single worker; it simply allows people to produce more content and, most importantly, elevate the floor of the overall quality.

Sometimes, it simply acts as a reference. I’ve heard a music artist explaining that he can now use MidJourney to explain what he wants for title art from his designer. And I myself use it to produce covers for my Spotify mixtapes. Again, technology always raises the floor, and MidJourney, along with other tools, allows people who can’t draw anything to turn their fantasies into reality (well, a real image).

You probably do need to think about AI when making life-long choices. My aunt recently told me her friend’s daughter had just enrolled in a university as a translator. Google Translate was shit ten years ago, got pretty good after this, and then was blown by GPT4. Does this mean we will not need translators soon? No, but there surely will be fewer jobs, and they will primarily focus on high-value tasks, such as adaptations of movies, popular books, etc. Ultimately, this means fewer translators and less money for them.

What happens when AI goes upmarket and captures way more? We’ll probably have to deal with this than by finding a balance. On the one hand, if we don’t automate things, the economy won’t grow, and everyone who is poor stays poor. On the other, as a society, we sometimes make decisions that might be suboptimal for the greater good. We’ll see what happens here, but even if one country severely regulates AI out of existence, others might embrace it.

Technology has replaced thousands of professions, all while creating new ones. We no longer have human “calculators” or telephone operators. Caution and the desire to preserve the living standards for some people is welcome, but imagine if we used the same approach a hundred years ago. We’d probably still have actual humans running elevators.

Blogging became popular in the late 1990s and early 2000s, with the rise of platforms like Blogger and WordPress, which made it relatively easy for people to run their blogs.

Then came social media platforms and managed services like Medium that ultimately gathered hundreds of millions of people who’d never bothered to set up their own blogs. Traditional blogs have been almost abandoned during this time.

And even though we’ve seen the resurgence of email newsletters and Substacks, they operate a bit differently: newsletters are usually more professionalized, and authors stick to one or two areas and generally write to make money out of it.

It’s not like all blogs died. I’m subscribed to a few dozen of them via RSS. But it’s certainly not what the majority of people are doing. Social media provided a straightforward way of broadcasting to a big audience, but as intermediaries, they could change the rules of this game (many media orgs felt the result).

The same is happening to Twitter now. Before Elon, its algorithmic feed was primarily focused on people you follow, bringing their most essential tweets and conversations higher while injecting a few “heroes of the day” for your amusement. I liked this feed and preferred it to the chronological one. The current “For You” feed is more like a textual TikTok, gathering anything engaging from your language’s segment of Twitter.

It’s indeed very engaging. Sometimes, I accidentally switch and notice myself scrolling through posts from unfamiliar people and all the emotions they produce in me. At the same time, I realize posts from the people I follow don’t always make it into my feed. The “Views” counter Elon introduced showcases this even better.

Unless you’re already big or willing to commit to this game of engagement farming fully, anything you write on Twitter there will likely stay irrelevant.

And here we come back to blogging. I started writing here four years ago, and at the beginning, it felt like shouting into the void. Coming up with content ideas was difficult. But everything I wrote was compounding. I can never predict which posts will do well, but in the long run, a few will attract attention. And sometimes, specific things and concepts I wrote about previously suddenly become popular, and people go to read up on them. Even coming up with ideas has become much easier. There are at least 10 posts I’m yet to write.

Compounding is the name of the game. Anything you write is searchable instead of being drowned or pushed outside everyone’s feeds. At this point, Google and Direct traffic vastly outnumber any Twitter engagement for me. Nobody cares about your old tweets (unless they want to cancel you), yet people regularly find the posts I wrote a few years ago.

There’s a concept called “Create Once, Publish Everywhere” and having your own blog helps, even though most centralized platforms suppress posts with outside links. When you lead people to your domain and provide them with some ways to follow you (email, RSS, and social), the conversion rates might suffer, but any of these followers is worth so much more. This was the key reason for newsletters’ popularity – not because everyone loved email, but the fact you could reach people directly without an algorithm between you (well, Gmail anti-spam and categories are a bit of an algorithm).

If you want to set up your blog, I have a guide here. Ultimately, it doesn’t matter what platform you use. What matters is that you stick with the practice and continue writing no matter what.

Superhuman is a productivity-focused email app initially designed for founders and executives that has massively expanded its focus since then. Its “the fastest email experience ever made” tagline is well-deserved. It’s also known as an email app that charges $30 a month and amassed over 200,000 on its waitlist, which made many people believe it’s obnoxious.

I’ve been a user of Superhuman since its early days (in fact, we invested in the company). I think it’s indispensable for people who deal with email a lot. This is enabled by many different things, forming a unique software experience I haven’t seen anywhere else.

Superhuman is fast. It’s a web app, but it’s the fastest web app I have ever seen. I mostly use it as a pinned tab, and there’s an Electron wrapper if you need one. All interactions are rapid yet smooth. But it goes deeper. Superhuman breaks the age-old concept of GUI and consciously eliminates UI elements like menus and buttons unless they’re critical. Instead, it pushes you to learn keyboard shortcuts and operate like a power user. In case you forgot or if you need to access a rare, more convoluted function, there’s a powerful Cmd-K Command Bar that has become a standard for powerful productivity-focused apps. And Superhuman’s natural language processing is genuinely one of the best.

As a result, the app is clean and streamlined. It’s almost impossible to miss an important email. One of my friends working in VC said this was the reason he’s paying for Superhuman, simply because missing a particular email could become a major problem for them one day. And if you need to deal with something later, it has fantastic Remind Me functionality.

Superhuman has a self-explanatory Split Inbox feature, allowing you to filter all emails into dedicated folders. If you’re asking how this is different from Gmail labels, you should understand that a) all splits are right in your face at all times, and b) you can cycle between them with one keystroke. It’s more similar to Gmail categories like Forums or Social, except you can create them yourself and as many as you need.

One thing many apps miss the mark with is their mobile apps. Superhuman doesn’t. Its iOS and Android apps are, of course, different, but they have all the necessary functionality for you to do things on the go.

***

Everything I described above can be helpful for anyone dealing with email. Now, one of the reasons I’m willing to pay that much is specifically because I use Superhuman in my work when pitching stories and announcements to journalists. It was just as relevant when I was talking to founders, other investors, and Limited Partners when I worked in VC. And it could come in handy for many other areas.

Superhuman has Read Status tracking. It even started a controversy a few years ago, which, in my opinion, was way overblown (but it’s good they removed IP and geography tracking from it). Now, one aspect of pitching reporters is that they get a ton of emails and rarely reply. If I see that they read my pitch and ignored it, I don’t have to follow up. Of course, there is similar functionality in other email apps (which aren’t free as well) and Gmail extensions like Mailtrack. But these extensions never integrate well. This was one of the original ideas behind Superhuman. Its founders built and sold Rapportive, a Gmail extension connecting with LinkedIn, and realized that many people used half a dozen of similar extensions at any time. Superhuman is a brand-new app that comes with these functions baked in.

And then there are little things they never even boast about. For instance, if you worked with Gmail a lot, you know its text formatting is a mess. You write something in Google Docs, paste it into Gmail, it looks completely natural, and you send it only for the receiver to get an email with a giant font you never intended (sometimes it only breaks in mobile Gmail which is even worse). Cleaning all the formatting could help, but what if you need the text to use bold/italic and links? When you paste text into Superhuman, it preserves that and removes font and size inconsistencies. The entire app is filled with these wonderful little things.

***

Is Superhuman perfect? No. For me, there are still issues. The primary one is the pace of development. The team shifted focus to money-making audiences of enterprise clients, sales teams, and Outlook users; as a result, the app has barely seen any improvements for the single-player mode in years, with AI being the only major update.

There are things I’d love to see in Superhuman. One is more advanced attachments search and management functionality, similar to what you can find in Outlook and Hey. I often had issues finding “that lost version of the agreement signed by both sides”. Certain aspects of the email workflow remain the same as they were a decade ago and I don’t believe they can’t be improved.

The main reason Superhuman is able to charge so much for an email app is that there isn’t any real competition. Mac users can try out Mimestream, a lovely Gmail client with a native app available on a much cheaper subscription. But it has no iOS app and probably won’t have one any time soon. Apple’s Mail.app is conceptually outdated and a bit slow since it relies on IMAP. Gmail’s iOS app is barebones. Outlook for iOS is actually nice, but it had the same bugs driving me crazy for several years, and the desktop version is much more convoluted. Spark was OK but wasn’t that much better, and I lost my outgoing emails on too many occasions for me to trust it again. Twobird is an interesting newer entrant, but I’ve seen so many services emerge and die over the years I don’t have much confidence yet.

Frankly, there isn’t a single iOS-capable email app I could recommend to someone. And this is pathetic.

The truth of the matter is building a capable email app is incredibly difficult. Creating a sustainable business on top of one is even more challenging. At least Superhuman seems to be doing both of these things together.

If you want to try it, here’s my referral link.

There’s a widespread notion that Uber is getting more and more expensive. You can find multiple series of articles produced on this topic each year and entire SEO-optimized webpages for this particular query.

Some people even believe that Uber is worse than conventional taxis right now. Uber’s only advantage to them was the price, and since those prices have soared, they see no value. In fact, these people believe Uber could only grow because of its initial low prices, artificially attracting customers and taking market share, only to leverage its semi-monopoly position later.

I think they completely misunderstand what Uber actually is and what makes it an excellent service.

Uber isn’t the only ride-sharing company even though it was the first. Depending on the country, you could switch its name with Lyft, Bolt, Grab or something else. I’d keep using “Uber” throughout this story.

***

While Uber and its clones dominate most markets, some have been left out due to insufficient volume (imagine a remote island) or government intervention. Bulgaria prohibited global ride-sharing apps. Barcelona (Spain) instituted an artificial 15-minute limit to force you to hail a conventional taxi on the street.

Every time I visit such a place, I realize what Uber is and how difficult it was before.

First, you have to find a cab. You likely need to be in a popular city area to do this, or you will have to wait a long time (or walk to a busier street). Maybe you can order via phone, although you’d need to know the language and have roaming enabled on your carrier plan.

Sometimes, there are entire lines of yellow cabs. When I went to Madeira, I saw a stereotypical line of two-decade-old Mercedes. They spend most of the day waiting, so when you take one, your fare also includes this empty time. You don’t know if they’ll have a terminal to pay with a card. The A/C might be busted, the car can reek of cigarettes or something similar, and if there’s a line, all the drivers expect you to take the first car, regardless of its quality.

A conventional taxi operates very similarly to a tourist-trap restaurant. There’s no expectation you will visit again. They probably don’t want to be completely terrible, but they also have zero desire to make it comfortable for you or invest in this beat-up Mercedes they bought for some unknown reason.

Uber changes this equation by becoming the arbiter. By leveraging their power as an aggregator, they can assign ratings to drivers and riders and execute control over them. Each particular passenger is no more likely to end up in the same car. But each passenger is a rider provided by Uber, something they could give or take back if a particular car isn’t great for their business.

And suddenly, fares go down a bit because Uber cares a lot about supply utilization. Drivers rush to buy a hybrid Toyota Prius with its great mileage (it also has lots of space in the back). And they never just stand in a line waiting for the next customer to walk to them.

The taxi experience before Uber and its clones was miserable. Did they subsidize the rides initially? Yes, probably. But its critics should at least stick to their line of reasoning. Because for many years, they were sure Uber would never be profitable until it suddenly was.

I don’t use Uber because it’s cheap. I’m OK if they raise prices to ensure drivers and the company make enough money. I use Uber because the experience is generally better, and if something happens, I have the company to deal with it.

***

Is Uber perfect? Probably not, as any big company. But we must accept reality and deal with externalities while considering consumer benefit. Do you seriously think a corrupt system artificially limiting taxi licenses to the point that they cost a million dollars in New York City is great? I find it laughable.

Basecamp and DHH specifically know how to trigger people and use this all the time to drive awareness without spending a dime. They take stuff that’s happening anyway, like when they had issues with Apple because of Hey, and sometimes they write something edgy out of the blue.

They juggled the names of Basecamp and 37signals, with the latter being the current one, but most people know them as Basecamp, so this is what I’m using here.

Basecamp is known for building very opinionated and slightly old-fashioned products as a remote and bootstrapped company. There are many similar companies out there, but Basecamp is certainly the most recognizable. Why?

Several reasons. First, they started back in 2004 (the year they switched to building products) and have survived to this day, which is an impressive feat for a tech startup and helped generate awareness along their journey. Second, they built open-source products, making them popular in the community, and an entire tech stack in the form of Ruby on Rails, which once was a very reasonable choice for web development. Now, Ruby’s share is about 5%. People used to it might continue working with RoR, but practically nobody is getting into web development through it.

Most importantly, they knew the role of marketing and communications early on. They showcased their uniqueness. Wrote multiple books on the topics they were into. Ran a blog. Hosted a podcast. Ultimately, advertised their company as a great place to work. Writing a book in the 21st century won’t make you rich unless it’s a bestseller, but it creates status. 

You see, Basecamp isn’t unique in being a bootstrapped company. The entire Indie Hacker community wants to get the same – become a millionaire and live off the income from your product, ideally without having any investors to report to. The challenge is it’s incredibly difficult. Only 5% of people there see any success. Andrew Wilkinson shared the failure story of Flow, his project management tool. This would likely happen if you tried building such a company yourself, although your mistakes would be different to his.

Their level of awareness and brand recognition is what makes Basecamp different from all of these indie hackers and small teams. This “secret sauce” enables them to sustain tech products operating in very competitive sectors. It’s practically free marketing. And because of their loudness and strongly-held beliefs, they manage to attract customers who are OK with their products the way they are. I heard a phrase that perfectly describes them: “Basecamp is a marketing agency with a software business on the side”.

Somewhere along the line, they realized that being loudly contrarian gets them attention. And what they actually do might be irrelevant, as it happened with the latest thing. DHH made a snarky commit that removed TypeScript support from their framework Turbo. Surprisingly, this coincided with their announcement of Once, which seems to be a new brand for software products you buy once and then figure out how to run and manage yourself.

And by this point, it truly feels too often they’re being contrarian for the sake of it. As if they’re specifically looking for a way to be different to everyon else. At the same time, they might be pushing people off with this approach Even their newer open-source projects, like Hotwire and Stimulus, are way less successful than Ruby on Rails was. Svelte is probably a good peer for their frontend framework, it’s also much less popular than React and Vue, yet still has 10x more stars on Github. 

Basecamp’s products are opinionated and old-fashioned. The description for Basecamp itself, their project management and communications tool, sounds perfect for a small team like ours. I tried it several times, but it always felt like you had to commit to its vision, as it seemingly lacked any flexibility or customization. I get a feeling it’s primarily used by a small number of people who click with it or non-tech companies. Especially, considering how proud they are for supporting older versions (these are customers who literally don’t want updates).

Hey, their email service, made a big splash, primarily because Apple wasn’t letting it into the AppStore. That wasn’t the smartest idea, considering the people they went against. For DHH, it was like he fell into a well of free chocolate He even went to the US Congress to talk about it. 

Hey is extremely opinionated, locked down to the point you can’t import your email history or use third-party apps with it, while their own apps are mediocre at best (largely because they’re cheaply made wrappers over their web version). I know it works for some people. It is ambitious, has an interesting story, competes with Gmail, and comes from Basecamp. I can tell you that they’d nice media coverage for this. But because of this “war” with Apple, they got 10x of what they would have if they just launched it peacefully.

I wanted to get back to the cheaply-made apps. This is a repeating theme here. Basecamp cares a lot about costs. One of the loudest recent crusades they went through was against cloud services like AWS. Don’t get me wrong, in 2023, it can be quite reasonable for a company like theirs. You have very predictable loads and aren’t planning to grow 10x; the tech stack is mature enough that running your own servers isn’t too different from virtual servers in the Amazon cloud, etc. But most importantly, they care about this because Jared and DHH get all the profits. They view it as a very reasonable and traditional approach for the business. And since their business is unlikely to start growing much faster, cutting down costs is very important. 

It’s just unusual for the tech industry. Employees of publicly traded tech companies get RSUs that complement their income and align the incentives with the company. Employees of privately held tech startups get stock options, which align their incentives and might potentially make them a lot of money (while being worth slightly over zero on average). Employees at Basecamp get nothing other than their salary, which is unusual for the tech industry.

Basecamp might be a great place to work. I heard the usual tenure for their employees is about 6 years, which is a lot for the tech industry. Although, this is the number I heard before they fired a bunch of people for discussing “politics” (or, being tired of being challenged). This arrangement might be perfect for them, they understood this in advance, it can be “priced in” their salary, plus they’re getting other perks, such as an asynchronous and remote workplace. 

I don’t have anything against this approach, as long as this was the agreement and both sides keep it. Mailchimp did a much worse thing: they didn’t offer equity, the founders boasted they’d never sell, then they sold to Intuit, and the employees who spent years building the product got nothing. 

Just don’t tell me being bootstrapped is some kind of a blessing here. It’s just another way to run your company, no more or less noble than raising venture capital or crowdfunding on Kickstarter. And it doesn’t prevent you from sharing revenue. Todoist, which was also bootstrapped, eventually started doing revenue sharing via stock options. 

For the same reason, I don’t understand companies that proudly say they will never attract venture capital or go public. It’s just not a great option for the team members, that’s all. 

Jason and DHH are genius marketers. All I’m saying is, maybe we need to be a bit more skeptical before we rush to write this tweet or a news story and give them what they want for free. P.S. Yes, I get the irony here.

There’s a certain community in tech that’s very vocal about their preference toward native apps. I share that sentiment, yet sometimes people take this idea too religiously.

First, what is a native app? It’s an app built using the native frameworks of a platform. For MacOS it could be SwiftUI. Such apps leverage the native platform’s interface, including windows, buttons, text areas, and everything else. They look right and familiar, and they behave this way. And most of the time, they’re smooth and fast. Historically, this has been the way to build applications for any platform.

But the Web has advanced so much from the early pages with hyperlinks that it’s now a platform for applications. Modern JavaScript runtimes, reactive frameworks (e.g. React), and platform APIs allow developers to use web technologies to build apps running on desktop operating systems. And this has largely become the preferred way to create new apps by now. If you use Slack, Notion, Spotify, or Todoist, then you’ve seen it. Their desktop applications are effectively just wrappers, usually built with a technology called Electron (Spotify isn’t though). And people hate Electron.

Here are the main problems people point out in web apps.

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Memory consumption

Each Electron app basically carries a large part of Google Chrome in it and has to keep it running. Naturally, this isn’t great for memory consumption. Of course, Notion is a complex app by itself, but in comparison, the native app for Apple Notes usually takes around just 120Mb for me.

This particular problem is impossibly difficult to solve. In fact, you might save a bit of resources by simply running all the same apps in your browser, since it will at least be able to share some resources and offload tabs when they’re needed.

They might be slow

Electron apps are known to be slow. There are just too many levels, and JavaScrip is an interpreted language, not a compiled one, so by default, it will be orders of magnitude slower than an app written in Swift, Rust, or C++.

Still, in my experience, this isn’t necessarily the defining characteristic of a web app. Superhuman is insanely quick. Todoist is also seamless enough. While VS Code is sluggish, it still performs better than Atom did. Unfortunately, such apps are rare exceptions. Yes, the foundations are indeed slower, but at least some people are capable of writing quick web apps.

Feel free to share positive examples you’re aware of.

They have unique UI

Since web apps can’t just use the components provided by the operating system, they have to recreate everything from scratch. And this creates a lot of burden for developers and, I think, lowers the quality floor. Creating beautiful, compelling apps is possible, but it requires so much work. People building native apps get it all “for free”. In fact, this could be one of the reasons Apple still has such a vibrant ecosystem of great artisanal apps since developers can build most things out of nice ready-made components.

This also means users often must learn your app’s UI instead of relying on their muscle memory.

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I’ve been focusing on desktop, but the same is happening on mobile, albeit at a smaller scale. Tools like React Native allow developers to build apps for iOS and Android. I’d say the “experience gap” is a bit larger on mobile. Notion famously started introducing more native components in their app, which instantly made it quicker and nicer to use. Still, their apps are largely web-based, which limits their functionality. For instance, it’s quite difficult to implement complete offline mode (Notion caches recently seen pages but nothing else).

Basecamp has a particularly good visual example of how this works, even though they use quite a “basic” approach.

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Web apps are here to stay. There are fewer and fewer artisanal Mac apps these days, even though sometimes a jewel appears out of thin air, as it happened with Craft. Quite unusually, they have native apps for all of Apple’s platforms and a web app with the same functionality, which is useful for people on Windows, ChromeOS, or Linux.

Native apps do feel great. But they have their own challenges. The first and the most important one is making them cross-platform. If you’re a small developer, you might not have enough resources for this. And if you’re a big company, you don’t want to struggle to keep all your apps’ development in sync. Building a web app and wrapping it with Electron ends up being the most reasonable approach for most people.

So most of the time, our choice isn’t between native and web apps. You either have that useful app or you don’t because it didn’t make much sense for the developer. And while I like native apps and enjoy them when I have such an option, I’d rather have a web app than nothing.

If I use the app all the time, I’d want it to be at least quick (and ideally, native). But if I need it occasionally, I’d be OK with pretty much anything, as long as it’s useful and there’s nothing better. Also, we have seen evidence it’s humanly possible to build quick web apps. The fact most people don’t bother is a different question.

It seems that we’re finally getting out of this weird period of collective gaslighting where people tried to convince everyone Zoom was the best conference app out there.

I prefer Google Meet. It’s just better. I understand it was terrible pre-COVID as if Googlers never used it themselves. But they’ve caught up in a major way since then. Now it’s a very competent web app that gets out of your way and lets you talk to people. You open the link, and you’re right in the call. Meet doesn’t ask you to update anything.

Look, I’ve been working remotely since 2014. We used to have calls with the US, and most of the time, people would suggest calling their cell (despite the terrible voice quality). Then I started noticing Uber Conference and GoToMeeting, which were a bit clunky but at least used VoIP to provide clear voices.

When Zoom appeared, it made things simpler, in large part by simply becoming a common standard first for the tech industry and then for everyone else. As long as you had the app installed, you could quickly join the call, and most importantly, it was reasonable to expect your invitees wouldn’t freak out because of this link.

But Zoom was never great. It still has a very clunky and ugly interface for scheduling and calls. Try quickly figuring out how to share the invite link when you’re already on the call. And the best option to schedule a call was using Zoom add-ons in Google Calendar or another app. Try doing it from the web or in the app, it’s like a flight control system.

The worst part about Zoom is its nature as a native app. I have no idea who decided it’d be a good idea to check for updates when you open it 30 seconds before the meeting and then block you from joining the call until it’s done. Zoom does have a web app, but it doesn’t want you to use it and hides the very possibility (most people don’t even know it exists). Why does a simple app need blocking updates so often? Oh wait, it’s no longer as simple as it was.

Zoom is worth $20Bn now and was over $160Bn at its peak. Between its annoying install prompts, forgetting you’re logged in, and the add-ons nobody asked for, there’s a simple truth that Zoom’s functionality is a commodity. If you run a company, you already pay for Google Workspace or Microsoft 365, which provide your employees with email, calendars, and video calls. So Zoom is desperately trying to justify its valuation and its entire existence by introducing things you don’t really need from it. I had to get Zoom Premium a few days ago, and it was almost $15 per user. That’s a lot of money for basic functionality you can find practically everywhere. And I’m not talking about their advanced features for webinars and such, most users don’t need this.

Zoom is going down the road of Dropbox. A company that once packaged known tech in a nice way and grew on it only to realize their product has become a commodity and every tech giant has a better-integrated version. So Dropbox decided to build features that would help justify companies paying for it and, in the process, ruined the experience for regular people (I pay for OneDrive now).

Right now, Zoom is very far from that old idea of an app that lets you simply join calls in one click. And despite all Google’s fumbles in messaging, Meet is just that. I know people have problems with Microsoft Teams, but I visited meetings that used Teams and it was fine. Again, no need to install anything, just open the link in your browser and click “Join”.

We also haven’t seen too much innovation in the space. Personally, I don’t like video calls too much (especially because I like to pace when I think). The only innovation we’ve seen is switching from big rectangles to smaller circles, which might be quite nice since it removes a little bit of anxiety and you don’t feel glued to the camera as much. SpatialChat is a good example, they’ve also tried putting everyone on a virtual plane so you can move between discussions as if you were in a room.

It seems to be quite difficult to build a successful startup in this space. I’ve seen Whereby that since shifted into offering whitelabel calls to other products. And there’s Around, which was acquired by Miro, and focuses on remote and hybrid teams that have to collaborate a lot while also supporting conventional calls.

But don’t tell me Zoom is the best, please.

I’ve just watched a funny sketch about Threads from Ryan George (look him up!) and noticed one thing.

He was calling Threads an app by Meta.

When Zuckerberg renamed the company, people laughed at this as an attempt to avoid the negative publicity associated with Facebook, or a corporate reporting stunt similar to Google calling itself Alphabet.

There was one key difference.

Google barely uses this name for anything other than their corporate reports on one weird website and still makes its money from ‘Google’.

Meta actually uses its new brand throughout their products. It’s also safe to say it no longer focuses on Facebook, instead relying a lot on Instagram, which it used to implement new formats such as Stories and Reels, effectively blocking the potential growth of Snapchat and TikTok. And they’ve slowly been building out revenue-generating capabilities into WhatsApp, without making the app more complicated.

So they truly deserve a new name.

The launch of Threads, Meta’s alternative to Twitter, has reinvigorated discussions about privacy and data ownership. A number of smaller Mastodon instances have preemptively defederated Threads, people have concerns about Meta launching yet another social app and getting even more data, etc.

Personally, I believe that we’re in the midst of a moral panic our grandkids will be laughing about.

A moral panic is a widespread fear, most often an irrational one, that someone or something is a threat to the values, safety, and interests of a community or society at large.

I often see people confusing different privacy-related things and using weaponized language to convince you something is bad. Just look at the terms thrown around. You need to protect your privacy and fight the surveillance as if these people are living under Stasi or trying to fight the statewide network of spies—the words we choose matter. By framing the problem in the right context, you can position yourself as the winner without even making a move.

‘Facebook sells your data’ sounds bad. ‘Surveillance’ sounds bad. But it doesn’t sell your data, and it’s not surveillance. If you can only articulate why you dislike sometime with rhetoric that isn’t actually true, that tells us something in itself. Benedict Evans

Meta isn’t selling your data. Meta is selling an ability to show precisely-targeted ads to relevant audiences. Some companies want to sell you their product. This list includes everyone from Unilever to a local car shop that needs people who drive Chevrolet and live nearby.

Show Me The Harm

Most of the time, privacy proponents cannot provide evidence of harm experienced by anybody involved. You could come up with some examples. After several US states made abortions nearly illegal, people realized the government could demand Google to share its search and location data to prosecute women using those clinics. It’s true that if Google, Meta, and others didn’t keep this data, this “attack vector” wouldn’t exist. While this situation is extremely unfortunate, we must agree that the actual bad actors here are state governments, not Google. It’s very reasonable for services to keep the history of your searches and location data to provide better recommendations (even if this allows them to target ads better), and they have to follow the local laws (even if they’re barbaric). The reason people blame Google is twofold. Some dislike them, while others trust Google more than their government, which is why they put pressure on the former.

Other than this, all you can likely find is the old anecdote about a parent learning their daughter is pregnant because of targeted ads. This story doesn’t seem to have any solid foundation, though.

Finally, there was Cambridge Analytica. In 2018 everyone was raving about the dataset scientists gathered from Facebook and shared with third parties that basically “allowed either Trump or Russia to change the outcome of the US elections”. Except it didn’t. Because the U.K. Information Commissioner’s Office released a lengthy report that found Cambridge Analytica’s work didn’t affect either of the elections. Marketers can promise you a lot, doesn’t necessarily makes it true. Cambridge Analytica used the fact Facebook had a more open API at the time and couldn’t enforce what users would do with the data. Yet when they closed it down, a lot of people were unhappy.

Instagram Isn’t Listening To You

Some have even been convinced Meta’s apps are listening to everything you say via your smartphone’s microphone! How else would they know to show me an ad for a thing I discussed with my friends but never searched for?!

They don’t listen to you, because:

• It’s technically-challenging
• It’d be trivial to detect
• They don’t need to

Because if you talked to your friend offline, you likely were at the same place, which allowed Meta or Google to put you in the same lookalike audience and try showing you the same ad. This is why you might see something your partner is looking for online – because you spent a lot of time at the same location (be careful with your gift research). The modern adtech stack is simultaneously complex and much simpler than you imagine.

Some could say even this concept is creepy. I get that. There’s a difference between an intelligence officer watching my every move and a soulless black-box algorithm that doesn’t care about me and is only trying to optimize ROI for a certain creative. What makes me worried is exactly the governments collecting data they have no legitimate use for from their citizens.

You Aren’t the Product, You Use The Product

You’re not just losing privacy because you sinned. In return, you get access to enormous free services. I’ve long advocated for advertising-funded services because of how egalitarian they are. It’s easy for a middle-aged person born in the US to claim they’d rather pay for everything than watch ads. The only reason I got into tech is that as long as my parents paid for the Internet access (dial-up at first), I had access to all the content out there.

There’s value in targeted advertising. It’s one of the best vehicles for businesses to reach their customers. There’s a reason Apple uses two very different warnings for ATT and its own advertising engine. They try to make it sound like what they’re doing is fundamentally different, but it’s not. Apple believes that anything you do on your iOS device is their “first-party” for them but “third-party” data for Facebook.

It’s “Personalized Ads” for Apple, but scary “Tracking” for everyone else, and Apple turns their option on by default.

Sometimes I myself prefer the ad-free experience. I pay for the ad-free tier on Netflix. But there are services, like social networks, that only truly work if everyone can use them for free at all times. And you likely underestimate how much services like Instagram or Gmail would cost you in their ad-free version. In 2022, Facebook’s (the “Blue App”) ARPU worldwide was around $39.65 (per annum), but in the US & Canada, some of the most profitable regions for them, it was $206.44. Are you ready to pay $17 per month for Facebook?

But if they make so much money on us, they should pay us!

I’ve seen countless attempts to build startups aiming to do this, both for the conventional web and in crypto. All have failed. Your information doesn’t cost that much by itself (if you don’t believe me, try finding a buyer). It becomes valuable when ingested into black-box algorithms at Google and Meta that operate petabytes of data and know how to extract value from it. Oil isn’t the best metaphor for this, the closer one would be sand when it’s turned into advanced microprocessors by TSMC.

Confusing Private Things and Behavioral Data

To make things even more confusing, people conflate some very different concepts under the same umbrella. Personally, I’m OK with targeted advertising, and I understand what it requires. I’ve bought many things off Instagram ads and specifically permitted it to track my activity.

There are cases where I care much more about the security of my data. I wouldn’t want my home address to be shared with strangers. I don’t want my medical or financial records to be publicly available. Sometimes I get notifications from 1Password about yet another hack of some services that potentially includes basic details on me, such as my name, email, and my password. These rarely include credit card details because not every website keeps them, and the ones that do have to care much more about this due to reason and regulation.

I don’t like such events because they could very easily lead to harm. It’s not about algorithms reviewing my “data” to generate revenue, it’s about humans using it against me to their advantage. Nobody can just bribe Facebook to get your data out. All big platforms care a lot about their data, this is one of the things that actually improved since Google and Facebook started dominating the online advertising market.

Some things are almost borderline. They usually happen because of incidents or miscommunication. In 2010, Google admitted that the cars used by Google Street View projects collected 600Gbs of data from open WiFi networks in Germany. The cars were fitted with antennas that look for WiFi networks and use the data for their location services. I doubt they could have used that payload data, but they should have been more careful.

Another thing that comes to mind is tech companies storing voice command recordings to assess and improve the quality of speech recognition. I’d expect something like this to happen, but they should warn about it in advance and give you an opt-out if you want it.

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I’m not against privacy, and I understand why people might not want someone to track web pages or apps they use. But it’s important to remember that there’s a trade-off and be prepared for the outcome. While I don’t like most of the GDPR applications, which just make many reasonable things illegal and solidify the monopoly of the largest tech advertising companies, allowing users to export their data or demand their account to be deleted is a good development. Creating a framework that incentivizes companies to safeguard users’ data and punishes them for leaks is also important, although I think we should be reasonable. In their desire to punish the American tech companies, the EU is too trigger-happy to issue fines exceeding what oil companies paid for the largest spills.

People like to say they prefer chronological feeds to algorithmic ones. I’ve seen countless prayers to Meta to re-enable the former option in their apps. And when Twitter made the algorithmic “For You” tab the default one, entire Chrome extensions were built, and petitions started to disable it.

I don’t think a pure reverse-order chronological feed is the best option. The actual problem here is we rarely see *good* algorithms built to help us and not drive engagement. But I’d love to see a social network giving me tools to catch up on the people I care about.

Strictly speaking, chronological feeds are based on an algorithm. A very stupid one. They work well when you only follow a few people, but they can be gamed. By design, they prioritize people who post more. People like professional bloggers and influencers. And if you only have a few minutes to check up on your contacts, you see a small slice of everyone’s recent posts – not necessarily the most important ones.

Kevin Systrom, Co-Founder of Instagram, who is now building Artifact, described their disadvantages in his interview with Alex Kantrowitz:

You would friend people, and your social network became your filter for relevant content. If I follow you and you post something, I see it. These networks grew to be slightly too large for that to be manageable.  If, on Instagram, we just sorted your feed chronologically, the people that posted the most would get the most attention and people would self report seeing too much of one person while missing other people.

He talked on the same topic in his interview with Ben Thompson:

We used to say internally, “Your feed is already ranked, it’s just ranked by order by created at descending.” Who’s to say that that’s the correct ranking for actually getting to most of your friend’s content? <…> “Can we help you stay up to date on what your friends are doing on Instagram”? That was the core of when it made Instagram special, and it was getting totally lost in a chron-ranked feed, because your friend posted 8:00 PM and in between then and the next morning, the brands you follow, the influencers posted fifty times because they have a whole team to help them post, and that friend post was totally buried.

I agree with this assessment. In fact, it mirrors my own experience with Facebook and other early social networks. If you are using RSS, you’re seeing the same problems. If you try subscribing to a major news website, they will drown you in content, dominating everything else. And if you’ve been away for a week, you’ll probably glance at the last headlines and just mark everything as read.

(Two years ago, I wanted to build an RSS service that would rank articles and posts for you. Thankfully, they launched Artifact, and I just use it.)

In anthropology, there’s a concept called Dunbar’s number. It is a cognitive limit to the number of people with whom one can maintain stable social relationships. And Robin Dunbar himself estimated this number to be around 150. I’ve always felt that conventional social networks and chronological feeds break around this exact number of follows.

Some people (especially in tech) claim that you must manage who you follow much more strictly. Follow carefully, remove swiftly, and mute the ones who post too much noise. I did this myself. And there are two very clear problems:

1. You clearly can’t expect everyone to do this.
2. When you mute a person who posts too much, you lose them ‘forever’. Unless you manually visit their page and give them a second chance, they will never re-appear in your feed. Maybe they just went to Coachella but ultimately are still reasonable people?

Social networking apps have tried to solve this in different ways. A now-defunct Path only allowed you to be friends with 150 people (the same Dunbar’s number). This would lead to a weird dance of trying to find someone to throw away to make space for the new person you want to add. Others, like BeReal, solve it through their UI and by limiting the volume of content. All of these options seem too artificial.

Twitter’s previous algorithmic timeline was actually quite useful in terms of surfacing the stuff I might have missed and mixing it with just a few percent of potentially interesting authors I don’t follow. The reason I (and many people) dislike the current “For You” tab is that it’s pretty much a TikTok for text. It’s extremely addictive, but when I pull away I realize that I don’t care about any of these people.

A useful algorithm would work to surface things I shouldn’t miss from the people I already follow. No matter how long you were offline, it’d highlight posts you need to have a look at. One of the common criticisms of algorithmic feeds is people refreshing the webpage and losing their position. This can be solved if the algorithm tracks the “seen” status (just like RSS readers do), so someone who is a completionist could read everything.

That’s what makes me slightly hopeful for BlueSky. One of the reasons they weren’t satisfied with ActivityPub and decided to build AT Protocol is precisely because the former doesn’t support algorithmic feeds.

At Bluesky, we’re approaching this challenge from a marketplace perspective. Our goal isn’t to create every algorithm in-house, but to enable the developer community to bring new algorithms to users swiftly and effortlessly

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Imagine being able, for the first time, to choose the algorithm building your personalized feed. Focusing on what you value. Mixing it with popular content or keeping it to the same list of N people you follow.

I don’t know who will actually ever build this. But it’d be wonderful.

Hating on media paywalls is very common. Whenever you see a paywalled article shared on Twitter, you can see people asking what’s inside and if there’s a way to access it.

One solution many people propose is micropayments. This implies being able to pay a relatively small fixed amount to access a single news story without subscribing. This is what Elon wants to implement at Twitter.

Rolling out next month, this platform will allow media publishers to charge users on a per article basis with one click.

This enables users who would not sign up for a monthly subscription to pay a higher per article price for when they want to read an occasional article.…

— Elon Musk (@elonmusk) April 29, 2023

Ben Thompson has a good explainer on why this wouldn’t work in the latest episode of Sharp Tech. The key reason is that while this might sound enticing for consumers (we’ll get back to this later), it’s technically impractical and terrible for businesses.

First, micropayments simply don’t make sense for publications. They can’t afford to acquire customers each and every time. They’ve invested in their teams and facilities. There are no marginal costs in a single article, but it’s also not an .mp3 file you could be selling for decades. Even the most successful publications, like The New York Times, aren’t terribly profitable (NYT had a profit margin of 15% in 2022)l. Most others fare much worse. So they’d much rather have a predictable recurring revenue instead of trying to entice customers to pay every time.

Second, card transactions are expensive. In the US, you’d pay at least $0.29 + 3% (most likely more). So if you want to sell one article for $1, over 30% would evaporate. And this is before we start talking about Apple’s 30% if you’re selling on iOS. There are ways around this. Twitch has tipping, so you buy a bunch of internal “tokens” in advance and then use them to award creators. This way, you only pay the credit card fees once. But you need a central actor to run this, and Twitter could have been such a platform, considering its role in the news ecosystem. Well, in its previous life, until Elon burned all the bridges and started replying to press requests with a poop emoji.

But now we’re getting back to the first point – news orgs (and everyone else) don’t actually benefit from micropayments. Twitter can build it, but I’m not sure who’d use it. It’s not just incremental revenue – it’s also lost recurring revenue from all those subscribers who’d subscribe if they couldn’t access the content another way. If you don’t want to subscribe, you aren’t the target customer.

One could argue that putting all your content behind a hard paywall could lead to a declining reputation since fewer people can read it (and be influenced). There are all sorts of factors here. This is a complex question, so let’s leave it for another day.

It’s impractical to expect people to subscribe to all news media. Well, I have to, because I work in PR, but I’m an outlier. But everyone has been saying the same about video streaming. The average person subscribes to 2.8 streaming services. You heard about that show on Disney+, so you subscribe for Disney+, and then you cancel it later.

Why won’t we do it with news websites?

Ok, there is no “Buy for $5” button, but if you really want to read it, why not subscribe for one month?

I think part of the reason is that people don’t actually trust their paywalls and subscription management. Netflix is the gold standard of subscriptions.

Look at its paywall. Clean, simple, no weird trials, no pricing change after the first month/year.

When you do subscribe, they send you an email before the next charge to remind you about it. Feel free to cancel in advance. And if you want to, it’s very straightforward.

With news media there are two key problems that I see over and over go: unclear pricing and a difficult cancelation process.

Now we’re slowly getting out of the terrible age when the only way of canceling your The New York Times subscription was to call someone. It maybe took FTC to get them them. But most news website have finally agreed you should be able to cancel your subscription online. Still, there’s still an expectation among consumers that you can’t. And with The Wall Street Journal it’s actually still the case (unless you’re covered by a local law). You don’t do this when you know you’re delivering value to you customers. You do this when you hope they don’t notice the charges for two years.

Then you have the “paywalls” themselves. Marketers at these companies try very hard to get you in and then start charging the full price afterward. The paywalls are designed to trick you.

Here’s Insider.

And here’s Financial Times.

You’d think having small grey font is something more akin to a sleazy insurance policy and not an news org you should trust, but here we are.

Just give us straightforward pricing and promise it’s easy to cancel online. I subscribe to The Information, and even though the subscription is expensive, the decision was easy, because I expect everything to be smooth and simple.

If you already paid for the first month, there’s a clear incentive to try using it while you can. The same you’d do with Netflix, Hulu or another streaming that shouldn’t have been started in the first place. And then, maybe, you realize you’re getting value and don’t want to lose it. Plus, nobody is subscribing to a news website to binge old news in one month just to cancel it right away.

Since Flickr made many terrible product decisions to alienate its customer base and Instagram decided they’re on to copy TikTok now, many photographers have been struggling to find a good place to post their photos online. You can find numerous Reddit posts with people wondering the same question.

The common thread you can see there is that there’s definitely not a single option the majority prefers.

Flickr was that option. The go-to photography website where everyone kept their own portfolio and caught up on the best photos posted in the community. They got too greedy. Or, they failed to deliver on mobile and correctly estimated the falling popularity of professional photography.

VSCO emerged as a more premium alternative as Instagram created the “VSCO Girl” phenomenon and is now trying to reinvent itself. 500px was popular for a minute and still seems to have a lively community, but it isn’t really mentioned in photographers’ conversations too often.

The common thread here is these apps either don’t target professional photographers or want you to pay up so much that they cripple the free tier.

Glass is the latest attempt to build a dedicated app and a community for photographers. It’s a subscription-based app available on iOS, Android, and desktop. The entire service is circled around photos – those are front and center.

The photos are glorious here. And the app itself feels quite nice. Some friction points exist, but I wonder if they’re intentional or accidental. For instance, if you want to upload multiple photos, you must do it individually. It’s not the best experience when you’re trying to put three, but I guess it prevents people from posting 20 in a row.

Part of the problem with such communities is that you can’t just find your friends or invite others. Glass definitely has a community. I simply posted photos there and started getting “appreciations” (that’s what they call likes) and even comments.

(You can look at my profile here)

Your photos showcase EXIF information (unless you manually erased it). Helpful to get the context behind the shot and how it was taken. You can also search for photos shot on particular equipment.

Probably one of my favorite features is the Public Profile. When you enable it, Glass gives you a link anyone can access to see your photos without having an account. And this webpage is gorgeous.

***

And now we’re coming to the key question I have about Glass. Social platforms are now trying to find alternative business models and testing out subscriptions. Glass heavily focused on “No advertising”. Instead, you pay $5 a month or $30 each year. I think the subscription model doesn’t make sense for general-purpose social networks, which must attract everyone to keep their network effects alive. But niche social apps targeting a specific affluent audience seem to fit a subscription product well.

Glass is fair in its business model. There’s a trial period, but there’s no free tier. But I fear that for an app focusing on social content, it’s an even worse lock-in than anything done by Meta.

Subscriptions for social apps are the ultimate lock-in

Let’s be clear, I’m not holding this against Glass. But your account effectively becomes a hostage.

As soon as you stop paying, the Public Profile is disabled, and the clock starts ticking. And then they delete all your photos. You can export, sure, but where would you import them?

And that’s why I’m hesitant to continue using Glass despite all the positive stuff. Because then I’m bound to pay for it forever or lose everything I’ve put and built there. And this is not a good feeling.

Considering this, it might make more sense to simply pay for hosting your photos on a blog so you’re the only owner. Or use the platform you can abandon at any time without feeling guilty. That’s why I started a microblog as my personal online journal with a separate photo page and also put some of them on 500px.

Reading all those discussions about the updates to Instagram and how people are turning disillusioned with the app, I began thinking: what would an ideal anti-Instagram service look like?

Let’s look at the most common complaints and try to find an alternative. Some of them are specific to the way Instagram works right now, some are true about any social network.

At last, we will try to figure out a potential business model that might work for this product and still onboard all of your friends.

Why Instagram?

However popular TikTok is becoming, I still think that Instagram is the primary social network for most regions in the world. This is where people keep their online profiles, this is what you ask if you meet a new friend (unless you go directly to messengers). Nobody is using Facebook to proactively meet and befriend people. Instagram offered a very simple way to produce content through photos and this is what most people can actually do. Especially compared to elaborate TikTok videos or endless snarky tweets.

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The Feed

The thing people vocally hate about the updates to Instagram is the changes to your feed. Instagram is pushing more and more content from people you don’t follow into your timeline because their data shows people tend to watch it.

The solution would be to only include content from people you’re following. There can be a dedicated discovery tab if you want to expand but it should never intersect with the feed.

It goes further. The OG Instagram was indeed about your friends. There were no influencers. The square photo format and filters were added for many reasons, but one od them was probably to disincentivize professional-grade content.

Is there a way to build a social network with no influencers? That’s a difficult question. You could copy Path and limit the number of follows or you could build it on top of phone numbers. Still, I could easily imagine services providing burner phone numbers so celebrities wouldn’t have to give up theirs.

Influencers are the power users of any network. They produce the most content per capita, likely the best content and generate the most engagement. Removing them might harmstring your growth but that would an interesting development.

Content

I don’t think people have problems with video per se. Except for the fact Instagram is favoring it algorithmically – which we “solved” in the previous paragraph.

Even more, get us more content types: text, entire galleries of photos, map locations, etc. There are apps like Dispo that experiment with the way you create content but I feel it’s just a gimmick. There’s no reason to make low-quality photos with your latest iPhone.

Photos are the easiest way to document your life and each of us now has a pretty good camera in our pocket. Let’s not limit it artificially.

When people are performing weird hacks to overcome the limitations of your platform it’s a sign that there might be something wrong. Instagram used to be quite good at noticing such trends and adapting to them. I remember how people started uploading vertical and horizontal photos by adding white bars. Eventually, Instagram submitted and let us upload freeform images.

When people on your platform are posting long texts as screenshots of Apple Notes in a gallery then something is wrong. When I’m making a screenshot just to use Apple Photos OCR to extract a link or a phone number then something is wrong. Such use cases should be assessed and processed. It’s weird that Instagram is worse than WordPress for a travel blog – it should be 10x better.

Engagement

There was a short period of time when it looked like Instagram cared about your screen time. You’d get a prompt that you have looked through all the new posts. But very quickly they started showing suggested posts instead of the previous ones.

This is a common claim towards any social network – they want to take over your time.

There’s an option to solve this I dream about.

Abolish the feed as it is.

Either use an RSS reader-style list of posts with read status explicitly shown or switch to a daily digest instead of a time-sucking endless feed.

Let’s say the user can choose the time of day and get their digest. Change it not too often.

BeReal found something similar but I don’t think it’s the content creation moment that matters. Most of the time I’m literally doing nothing spectacular. But if I only can catch up once a day it’ll be a much healthier experience.

The Walled Garden

Instagram is a walled garden. At least we now have a web version, which you can use on the iPad in the absence of a native app. You can’t select and copy text. You can’t add links to posts, only stories. You can’t reliably read all comments, especially on the web.

I’m following all kinds of volunteers and while Instagram is a good place for them to build their audience, it’s terribly difficult to raise funds or even leave a CTA.

So let’s open it. And that might allow us to solve the chicken and the egg problem of any emerging social network.

Users have no incentive to start a new social network if it doesn’t have their friends already. So they should be able to easily share their content outside. And if we’re adopting the digests model, we can use email to distribute it. We still have to acquire and onboard the user who creates the content, at first their followers could sign up via email or third-party messaging apps.

Position it as a life journal so there’s an incentive to post at least for yourself while the network is trying to grow.

The app would provide a more complete experience, comments, DMs and all other things so people interested in it might join eventually.

Monetization

The most important part. We can come up with the ideal app, but if it doesn’t have a scalable and inclusive business model it will fail and lose ground to Meta or anything that comes after them.

Glass is an interesting example. It’s also a photos app. But because of their chosen style and a $5 subscription only photographers are using it. It’s unreasonable to expect everyone to pay a comparable fee, especially since the world has other countries in addition to the US and Europe. Micro.blog is similar. It is very close in terms of its ethos. But most of my friends will not be paying $60 a year for it.

WhatsApp experimented a bit with a $1 annual subscription in select regions. On paper, it might work. Build an app that has almost everyone and you will have at least over a billion dollars. Still much less compared to Meta. And in the early stages, this will likely be unsustainable.

In fact, I don’t even have a problem with ads. Ads made Internet free and available to millions of kids, including myself. But all the ideas introduced here, from daily digests to focusing on real friends, clash directly with the advertising monetization model and the engagement and data it requires.

***

I would call this the Social Network Dilemma. A social network is only good if it actually has at least most of your friends. To do so it has to be free for the end user and have a viable business model that powers its growth flywheel. But then we end up with an app that has dramatically different interests and doesn’t really serve us. And subscription access limits the numbers of people who’d onboard further decreasing the value of such a network.

I do believe that with a sort of a distinction between content creators and content viewers we can accommodate some of these downsides. If the content is spread beyond the network and people have multiple ways to follow without being active participants it is still viable. But who knows?

The only option we seem to have is some kind of a premium tier for people who might want a bit more in terms of features. Similar to what Telegram is doing (with an unknown level of success). If you want more photos per post, unique visuals and appearance, and other power user features – you pay. Only by letting people join for free and still earning money through subscriptions the network I described is likely to be viable. Still, the subscription by itself doesn’t solve all the underlying problem. You still want more users, you want them to be engaged, so you might end up in an eerily similar place. Or let business users in and charge them for their accounts. But you need to be able to generate value for them.

Building a social network is probably one of the hardest problems in consumer tech world and I’m not going to pretend I know anything about this. But as a user I do often feel that the apps we use let us down and don’t offer an experience designed specifically for our goals.

I think the lack of sideloading has been a tremendous advantage for iOS and Apple’s ecosystem overall. I also need Apple should open it up.

The fact you can only install apps from the AppStore on iOS gives users, developers, and Apple itself tremendous benefits. Users can install any app with no fear for their wallet or data (hm, most of the time). In turn, developers get more revenue because users are willing to install and buy new apps. Developers also don’t have to worry about piracy – it doesn’t exist. That’s different on Android, where I can go to an online forum full of cracked .apk files visited by 30 million people a month. Google even offers special anti-piracy protection to developers. I think it’s more than just about the lost share of their revenue. This status quo has likely affected the very business model of thousands of apps on Google Play Store, pushing developers to advertising or from developing an Android app in the first place.

iOS doesn’t have these issues. There’s a notion that all Apple platforms don’t really suffer from piracy or malware but I can’t really agree with that. There are websites with cracked apps for MacOS (I won’t link to them but you probably can find them) and there is malware targeting Macs. The scale is much smaller, of course, but that is just a correlation to the number of Mac users. This is just iOS.

The fact you had to go through the closed AppStore and give up 30% of digital revenue is an issue for many developers and publishers and will likely be one of the key points of any future anti-trust action against Apple. Epic Games played a game of chicken with Apple and working things out in court right now. If iOS allowed sideloading without jailbreak many developers might have chosen to stay out of the AppStore, just like they don’t distribute their Mac apps through Mac App Store. But that would also destroy some of the advantages iOS creates for both users and developers.

I believe there’s a very particulate user where sideloading is reasonable. To clarify, where Apple relinquishing control over what apps you install is reasonable.

It’s censorship.

People throw that word all the time now but I’m specifically talking about the government-level censorship. Some people believe that the block of Parler by everyone in the tech industry from Apple to Amazon AWS was an act of censorship but that’s a different discussion that I’m not going to participate in right now.

Clubhouse, a voice-based social app value at $1 billion in their most recent Series B, just got blocked in China on multiple levels: ISP, Apple AppStore, carrier networks. This means that in order to run Clubhouse there you need:

1. A VPN
2. An alternative iCloud account for the AppStore
3. A Non-China phone number

That’s more than enough friction. VPN is probably the easiest part, though most of the well-known ones are blocked as well. AppStore is a bit trickier – you can create a new account without a credit card. But it’s a huge hassle to switch between them and you’d lose some things e.g. like tracks downloaded in Apple Music. And if you need to buy an app or make an in-app purchase you’re out of luck – you need a foreign credit card as well.

Clubhouse is hardly alone. Most of the Western social networks and apps are blocked in China in a similar manner, although at least as far as I know they don’t always block confirmation texts. But you can’t access Facebook, Google, Youtube, or a myriad of other services in China. Apple follows the demand of China and removes entire categories of apps from the Chinese AppStore. They even built a unique Apple Podcasts app for the Chinese market.

India banned TikTok in June 2020 alongside 59 other Chinese-made apps, citing national security concerns. Russia blocked LinkedIn and has been developing the technical and legal capabilities to enforce such bans. Benedict Evans called the end of the American Internet in 2020 since 80-90% of Internet users are now outside the USA while the Internet itself became vastly more important. This means that countries with a tendency to show off their sovereignty begin to both favor their tech champions and heavily regulate the global entrants.

The Internet was born as something truly global but in a sense it was American. US-based companies dominated since they were able to generate more revenue and spread their fixed costs on a much larger userbase than any platform in a smaller country could. As a result, the US partially exported their legal system and values onto those platforms. And I think that had a positive effect on most of the world since those values often were more open and democratic. But now it seems that process was a fluctuation and not something we should take for granted.

Apple still wants to sell its products in China, India, Russia, and all other countries. But having the centralized switch to control what apps you can install and how you pay for them becomes a much larger liability for them when governments get involved. And it’s very detrimental to their users. There are bypasses for free apps but only of them. If iOS allowed sideloading even in some limited form alongside the main AppStore that pressure would be removed.

Potentially, getting access to a blocked app might be the only reason I’d ever buy an Android phone if there is no other way.

Our browsers are astoundingly outdated and their developers seem to be oblivious to that. We went from basic Hacker-News-style HTML pages sprinkled with a little bit of Javascript to running full-scale applications like Figma or Descript – something you wouldn’t believe to be even possible in a browser ten years ago. The whole definition of the web browser changed – it’s not just something you use to “surf the web”, it’s where people often do all of their work: email, calendars, documents, design, even code with things like Github Codespaces or Replit.

Now, look at this Chrome from 2008 or so.

And now look at the modern one.

It certainly looks better. Yet the actual UI barely changed in all these years.

I’m mostly using Chrome as an example because it’s at least 57% of the modern web and is expected to be the most advanced but you could look at most other browsers and you’d see the same picture.

We went from web pages to web apps but the UI paradigm hasn’t really changed. Everything is a tab and all tabs are the same and each belongs to some window – which are also the same.

You can pin tabs. Most of the time I have 3-4 most important apps pinned right there and I’ve seen a lot of people do that. Still, they live in the same area and occupy the same shortcut space (Cmd-1,2,3,…,N).

PWA and in-built Chrome’s functionality to “Install” apps could have helped. It creates a local shortcut for this webpage and launches as a dedicated app within your OS. But in order for the experience to be smooth you really need the app to be a PWA, otherwise, it’s too finicky for a regular user. For some reason, only a couple of Google services, such as Google Photos, are actually available as a PWA and look like a well-behaved local app. All of their most popular apps, such as Gmail, Calendar, or Docs don’t. Even if you “install” them, manually change the icon to look good, you’ll soon face issues, for instance, it’s impossible to change an account in Google Calendar without being thrown back to the browser. Google could have led us and turn all OS into literal launchpads for their own web apps would be highly beneficial but instead they dropped the ball.

In general, there are two distinctive ways people deal with browsers tabs:

• People who mostly have a few tabs
• People who have two hundred tabs at least

Personally, I’m in the first category as too many tabs immediately make me anxious. But I doubt browsers actually work well for the second category – or do anything about this scenario at all. Go hunting with your mouse or use shortcuts to switch between the first 9 tabs and left-right. There are extensions that help with it: from The Great Suspender that intelligently unloads the unused tabs to OneTab that helps you save sessions to things like Tabbs that just help you find anything in your browser. Unfortunately, most of these extensions are created by single developers, can be dropped at any moment and have terrible design (not all of them, but most). Basically, you’re at their mercy.

It reminds me of the way early Mozilla Firefox worked – its early versions were so barebones, you’d have to install extensions just to get you some basic functionality like saved sessions or downloads manager. I think we can expect more from our browsers in 2020.

Sometimes they give us an experimental feature that could really help, like recently added tab groups, but based on the past performance there’s no indication they’d continue working on it and provide an API to extension developers. Imagine if you could save a tab group for later, push any existing tab into a tab group you saved, if they could freeze automatically when you collapse a group so they wouldn’t take memory. If only.

In fact, these are the things I would want to be present in a browser:

1. Advanced tab management functionality
2. Session manager to quickly switch between different contexts
3. Command menu to quickly switch between tabs and look up items in history
4. Better support for proper web apps

You can achieve some of that with a combination of extensions but it’d all be supported with a duck tape and look pretty bad.

By the way, Reading Mode that Chrome added some time ago is a joke.

Solutions

In the past few years, I’ve seen a few attempts from venture-backed companies to create a new “browser” or augment the existing ones. Why venture-backed is important? Well, these are companies, not individuals, and they have enough cash to build out a product that might become financially viable. I’m not yet sure most of them would be able to justify venture-scale returns in the end though, except maybe a few.

Mighty

Mighty is a cloud streaming for Chrome. You can buy the lowest-end MacBook Air and then casually browse 500 tabs filled with heavy apps with no issues. Our laptops are highly optimized for video streaming so it should last long and eat way less RAM.

Initially, I thought it was a weird idea, but then I realized that a) we all work in web browsers b) if you solve Chrome streaming, you solve streaming for any app.

Mighty is in limited access right now. I haven’t tried it but as far as I know they add a few niceties here and there to make Chrome a bit better. Maybe in the future they’d heavily upgrade it as they had to fork it anyway but we don’t know yet. I suppose it doesn’t actually solve the issues I’ve been talking about but would solve the innate “heaviness” of Chrome.

Browser Company

The elevator pitch for the Browser Company is exactly about building a new modern browser from the ground up. They are very early so you can only see certain experiments they showcase from time to time.

Despite the ways our internet use has evolved, the browser has remained relatively unchanged. While all of our other software tools are changing for the better—with more collaborative features, flexible interfaces, and powerful functionality—the browser largely still does what it did twenty-five years ago.

That’s why we’re building a new browser—we believe it could do so much more to empower us. We’re imagining a browser that can think as quickly as we do, take work off of our plates, and pull our creativity forward. A browser equipped for the way we use the internet in 2020, and foundational for how we hope to use it in the future.

Building a new browser is insanely hard. They are extremely complicated apps. Even if you just fork Chrome and try to add some UI you’d likely fall behind very quickly. I’ve been using Edge for some time and it already falls behind Chrome in a few areas: no rich audio control, tab groups can’t be collapsed, etc.

Station

Station started as an alternative to browser – a command center for your web apps. Its biggest advantage was that tabs were tied to an app so you could have a hundred of them opened and you wouldn’t even see that. Also, things like being able to quickly switch between accounts in a more reliable way. Station was built on top of Electron, a framework developers use to bring web apps to the desktop. Each app or service has to be added to Station directly by the team. On top of that they had to rebuild all the features users would expect in the browser.

With time the developer realized it was a dead end. Users liked the concept but the performance was pretty bad so they’d churn. The team made a heavy decision to drop it completely and turn Station into a regular Chrome extension. Now they don’t have to recreate the entire browser but at the same time they don’t have control over it and their functionality will be forever limited by the APIs provided to them. Also, I recently switched to a new MacBook with M1 inside it, but on my previous Mac it was insanely slow and I couldn’t use Station at all.

There have been a number of similar apps such as Wavebox, Shift, and a bunch of others. I think the ones trying to rebuild the browser based on Electron won’t have much luck. It just doesn’t make sense if people still have to use another browser and it’d be quite hard to catch up.

Building a new web browser from scratch using a framework (Electron) that was never designed to do it meant iteration cycles were slow. Very slow. We were not learning fast enough. On top, we had to build features you simply expect as standard in a browser and fix bugs that users wouldn’t typically experience in a regular browser. That taught us nothing at all.

Workona

Workona is a Chrome extension that adds deeper integrations with apps and enables search across their histories, proper sessions and tab management, as well as collaboration features for teams. It also faces all issues of being a heavy extension replacing the new tab – on weaker machines it’s a bit unpleasant to use. When I was using it, it also had limited integrations with apps – it couldn’t really do more than search your browser’s history for a respective domain.

Sidekick

The team behind Sidekick decided to outright fork Chrome. That allowed them to perform far deeper modifications and keep it quick.

• Sidekick has a separate apps bar on the left that is visible on all pages. So if you always want to have Gmail, Notion or Calendar open you don’t have to keep them pinned and constantly stumble upon them. They’re here.
• Sidekick has a very powerful search across your history and open tabs. If you want to open a document, a Slack channel, or a Figma mockup it’s likely you opened it before – so they can provide a ton of value by just surfacing your history items.
• Sidekick has user sessions and you can quickly switch between contexts. At the end of your workday you could just switch to a personal session and have a clean slate, while all your countless work tabs are safely preserved.
• It has some nice additions such as an embedded ad & tracker blocker and ML-enabled tab suspender to save RAM.
• What’s also important is that their modifications are rather limited. You can enable Chrome syncing and other Chrome instances would believe it’s a regular Chrome, so you can send a tab to it from mobile, for instance. Still, the features may lag behind, it doesn’t have a build for Apple Silicon, for instance.

I really hope we will soon see ever more significant advancements in the browsers’ UI.

Upd. Based on the feedback I’ve adjusted the description of Wavebox as it’s not an Electron app but a Chromium fork.

Probably, one of my most controversial opinions is that online ads are actually great for the society and the public narrative shifting to paid subscription software, services and content might prevent a lot of people from accessing them in the first place.

You see people in tech being very vocal on the topic of monetization models of Google and Facebook. Some claim they’d prefer to have a paid ad-free experience and ready to pay however. As of September 2020 the ARPU for Facebook is almost $12 per month and it’s mostly driven up by the US and Western Europe – that’s how much they’d have to pay. Tech Twitter welcomed Hey, a paid email service that costs at least $99 a month, as well as a number of other apps and services. That effect is accelerated by the whole industry of apps switching from one-time purchases to subscriptions – a whole different question. And paid premium software is getting way more expensive, something I covered before.

It’s one thing to live in San Francisco, work at a tech incumbent or even a startup, and have enough resources to throw some for an exclusive email service. Or you can live in Utah. Or maybe in a small village in Italy. The average dollar-adjusted income varies in different developed countries but it’s still high compared to the rest of the world.

But there are people who have a much smaller income or maybe none of it. I didn’t have a debit card when I was growing app. They were a thing but my parents didn’t really have them. Even if I had some cash it would have been extremely difficult to buy something online with it. I was only able to start doing that when I started earning a bit of money doing web development – and accepting WebMoney, a product with a truly terrible experience but too few alternatives at the time.

Despite all of that I was able to enjoy the same global Internet as basically anyone else. We used the same Google. We all raved about Gmail when it launched. I learned a ton of stuff by reading tutorials and chatting on forums. Early social networks allowed us to communicate with our friends and classmates. All of that was free for us and funded by our mere potential to buy something. And it was beautiful.

I enjoy seeing great artisanal software created for people who are willing to pay more money to get nicer things. I’ve been one of these people on multiple occasions. And yet I worry that this might lead to the segregation of the Internet and radically different experiences for people with an opportunity to pay and the ones without it.

There’s nothing nefarious with collecting data we share online in order to serve better, more relevant ads. It’s not your crazy stalker watching your windows through a pair of binoculars. It’s a set of algorithms which don’t care about you at all. Radically limiting that data collection would lead to much lower CPM/CPA and fewer people and companies willing to pay for your attention. Online ads aren’t always great: they might lead to a bad reading experience or throttle your browser. I support fighting that part of the issue. But I’ve never really hated the experience that ads on Facebook or Instagram give me. It’s not ideal but I wouldn’t pay for that service.

By the way, Hey now has 30,000 paying customers, which is very impressive but also shows how many people are actually ready to pay for software when there are free alternatives.

And of course, there’s a ton of edge cases in tech, just like in any other industry. People might use social networks to spread political lies. Or target real estate ads to only white people. This is still a new industry and we need to deal with it on a case by case basis, learning and adjusting the policies to avoid this. But threatening to throw away the concept altogether is just impractical.

Google was founded in 1998. Altavista was created 3 years earlier and although it was probably the most popular search engine for the English Internet it lost its relevance simply because Google was better at indexing the web and ranking the pages to extract the most relevant webpage for your query.

There’s an infamous negging question that some investors ask:

“It’s cool you folks are doing that but what if Google enters the space?”.

That question is mostly useless because Google isn’t really a single entity. It has myriads of products that you could compete with:

• There are core products where Google is practically invincible: search and advertising network.
• There are products where Google’s advantages in scale make it harder to compete. Google Photos is probably one of their best services. Google can easily absorb storage costs and has enough CS PhDs to augment it with basic AI. Try building something better – and free. Google Stadia requires very specific competencies in data centers, custom hardware, and exquisite backend. Even Android phones – Google might not be the best at hardware, but the example of Essential showed us how difficult it actually is.
• And there’s everything else, from Google Tasks to a myriad of canceled products in the Google’s graveyard.

You can definitely compete with Google’s non-core products. Gmail’s former lead designer explained why even with all their resources Google would have issues with shipping better software.

The obvious ways to tackle this problem is from the inside. I’ve tried that. As much as I loved Google Inbox (a product and team I co-founded but left before launch), what launched was a well executed and polished but watered-down version of the original vision.It isn’t that the teams behind these products don’t care. They care deeply. But big products have big teams and are often inside big companies with their own bigger (and often unclear) priorities. It is messy.

Can you tackle their core business though?

Facebook managed to build a compelling advertising business due to their enormous userbase and innate ability to capture data to target ads better.

Nobody was able to beat Google search though. The problem is that like many kinds of software there’s a positive feedback loop. The more people use Google the better results it can provide. This leads to even more people using Google since they believe it’s a superior product. All the data goes back to Google and improves its algorithms. With all that revenue Google is able to hire the smartest people in the world and pay them way above the market to ensure its algorithms would be advancing faster than any competitor is able to.

Yes, there’s Bing and privacy concerns push some people to DuckDuckGo but almost all of them admit that its search quality is at least slightly worse – it depends whether you care more for the relevance of the results or visual simplicity, lack of ads, AMP pages and search snippets that alternative engines provide.

10x or Nothing

In order to really beat Google, you need to build a compelling product. And since users’ habits are really hard to change, this product needs to be not just marginally better, but 10x better – and without all that data that Google already has. But wait, how can you achieve it? It’s not like Google’s search results are trash. They’re generally very good. When I was a kid I had an entire book on how to use various search engines (most of the services it taught are dead already). But now you don’t even have to learn, it basically knows what you need.

The current understanding of technology trends say that new platforms emerge during paradigm shifts.

• Microsoft became a dominant tech giant because it entered the market with the right product at the right time. As the hardware architecture became open, it quickly was commoditized and IBM with their old mainframes couldn’t compete.
• Then Microsoft lost its relevance when modern smartphones appeared and turned out to be more important devices than personal computers. Apple and Google defined that market and benefited greatly from it. In 2019 Apple made 54.7% of its revenue on the iPhone alone.

That gives us the direction to look into. Google takes our queries and provides us with webpages. But the fact is, we don’t really need webpages, at least in most cases. We need answers. That’s why Google has been adding all those search snippets that give you an answer without making you follow a link. But these snippets aren’t automated at the high-level and there’s an army of developers of Google building them out.

The paradigm shift would be some sort of AI that gives you answers to your questions. That could convince people to actually move to your platform – because the advantages are 100% clear. And this is an improbable task. We’ve taught Alexa how to answer the birthdate of Lincoln and the distance between the Earth and the Sun. Imagine a service that has to answer any question. What’s the best chair? What drugs to take if you have the flu? There’s an enormous set of challenges, not even just technical but also related to legal questions and basic safety.

Open AI recently released their GPT-3 language model that can generate answers. But people already figured out reliable ways to crack it. We’re still not able to create something that would pass a Turing test and it seems in order to replace the search engine with the answer engine we’d need a proper strong AI.

Google understands that. They invest enormous resources in AI, so many that a $500M acquisition of DeepMind pales. But the thing about the paradigm shifts is that incumbents aren’t always able to overcome them and keep their position at the technology Everest.

***

Well, it’s 2023, ChatGPT is out there and Google’s founders got back to its HQ to discuss the threat posed by Open AI.

Recently John Gruber asked on Twitter if anyone is aware of a good native outliner app for Apple platforms. There are two extremely tragic aspects of the reactions:

• There aren’t any.
• Most people don’t know what outliners actually are.

What Are Outliners

Outliners are a very curious category of software products that have been mostly used by a small number of geeks but recently captured more attention with the launch of Roam Research. Yes, it’s also an outliner.

An outliner is a text editor that organizes information in a hierarchy, allowing users to control the level of detail and to reorganize according to the structure (source). In outliners the bullet item is the atomic unit of information. Your notes can be very detailed, yet organized for a casual reader to get a quick overview. Certain apps add their own flare to this workflow but similar at their core. Examples include apps like emacs org-mode, Workflowy, Dynalist, OmniOutliner, Little Outliner, and Roam Research.

Why People Love Them

Outliners impose a very strict hierarchical structure that shapes everything you write. Paradoxically, they’re also extremely flexible.

• Outliners are great for note-taking because they incentivize you to structure your notes.
• Outliners are great for task management because they let you build what you need at any particular moment. Ordinary task managers impose a specific workflow: some have projects, some have areas, some have priority tags. And if you were to look at people’s outlines – they are dramatically different.
• Real life is often too messy to accurately separate quick notes from tasks. Outliners can digest both notes and tasks at the same time.

I noticed that any meeting notes I write in them immediately become better as I a) ensure that any bullet item covers one thought or an action item b) related notes are attached together.

But outlining isn’t just about writing in bullet points, you could do that in a Google Doc. You can also expand and collapse certain nodes along with their children to focus on what you need at the moment. Modern outliners provide additional features, such as allowing you to zoom on specific items and add tagging and filtering to enable a second dynamic hierarchy in addition to the core static one.

That makes outliners perfect for task lists. Despite all kinds of productivity and task management apps out there, I noticed that most of the executives I know end up just writing everything as a list in some note. Or maybe something slightly more complicated.

I’m still not sure if that is a sign of failure of all these apps or if this particular approach is truly the best and we just haven’t seen the app built to capture that. Outliners are close, Stewart Butterfield, CEO of Slack, has been a fan of Workflowy.

emacs org-mode

emacs has a document editing, formatting, and organizing mode called quite literally org-mode. Org-mode was created by Carsten Dominik in 2003, originally to organize his own life and work.

It’s very geeky and just like many DIY solutions popular among the UNIX fans is known for its quirks, steep learning curve, and issues with specific implementations. Yet people still use it and add new feature through plugins.

Omni Outliner

OmniOutliner is an outlining app for macOS and iOS created by the famous productivity masters at The Omni Group. OmniOutliner has most of the features of a conventional outliner and comes in two versions: Essentials and Pro. Essentials is heavily stripped down and available for $19.99. The Pro version is priced at $99.99 and has extensive customization options, section navigation, automation, and other features.

It’s more focused on actual lists keeping and formatting. Compared to many other apps in this list it’s what Pages is to TextEdit. And this is also probably the only outliner that has a good native iOS app. Unfortunately, it’s pretty classic and doesn’t have any tags or filters – even though OmniFocus, their well-known project management app, excels at these.

Workflowy

Workflowy is one of the most famous apps in the outliners space. It was created by Mike Turitzin and Jesse Patel. Workflowy redefined the concept of the outliner in multiple ways.

1. Workflowy threw away the old-fashioned file-based structure. You don’t create new files or folders in Workflowy, instead you have a giant infinitely-nested list. But you can zoom in on any node and focus on it and put the nodes you often need in favorites.
2. Workflowy added tags and saved searches that allow you to filter nodes based and only surface what you need at the moment across the entire graph.
3. More recently Workflowy added dates providing even more project management capabilities.

For a couple of years, the app wasn’t seeing any updates and that took a toll as many users tried to switch to something else. In 2018 the co-founder promised to make it better. Since then they launched new apps and added some long-requested features like the dates support.

Workflowy is my personal outliner of choice now. My project management workflow is based on a long tree of clients with all the stuff I need to do and check. I mark specific tasks with tags: @do for what I’ll be doing today, @later for non-urgent things, tags for individual team members to remember what I delegated, and dates when we have specific deadlines. Workflowy allows me to quickly switch context from observing everything we have on our plate to focusing on a single project or task. It’s also just helpful for organizing my thoughts – I wrote this post in Workflowy first.

Still, the development pace isn’t exactly where I’d love it to be, it’s tedious to add notes and tasks to Workflowy from other sources (no options to add via email or via share sheet) and the iOS app is a pretty obvious wrapper on top of the web version that doesn’t feel native. Workflowy also has suboptimal official manuals: you’re supposed to read the blog and for a lot of stuff the most recent records 4-7 years old are often outdated.

Workflowy’s free tier is pretty robust yet you can only create a fixed number of new nodes each month. Early users have it fixed at 250, new users only get 100 now. The paid version is $4.99 per month and $49 per year.

Dynalist

Dynalist was created in 2015 and was more of a response to the stalled development of Workflowy.

Compared to Workflowy, Dynalist has more advanced dates, attachments, version history, calendar integration, and a ton of other stuff. It also just gets so many things right and the pace of development is much faster. The app itself doesn’t look that polished and mobile apps are especially bad. They’re wrappers of the web version and aren’t good ones.

It gives more for free yet costs $10 a month ($96 a year) if you want advanced ones (and believe me, you want the ability to quickly jump between nodes from the keyboard).

The good thing is that both apps can easily import the stuff from the other one and you can simply test both side-by-side to understand which one you prefer.

Roam Research

Roam Research is a “note-taking tool for networked thought” that has extended the feature set of a basic outliner by miles. It’s still an outliner and everything you type is a bullet-point. But the app doesn’t want you to create a defined hierarchy – instead everything is supposed to be dynamic. Roam allows creating new pages by just writing something inside square brackets (wiki-style), see backlinks (all the nodes and pages linking to the one you’re seeing right now), and block references (linking and repeating a specific node to provide context). The app wants you to build your own private wikipedia for your knowledge.

Roam Research has one of the steepest learning curves I ever saw in software. It allows you to do almost anything and that’s overwhelming. Thankfully, it has a very opinionated part of the workflow – “Daily Notes”. The idea is, instead of trying to find the perfect place in your hierarchy for all kinds of notes, you just type everything in the note titled with today’s date and add links and tags to connect those items. You can log your morning run, mention that you talked to a long-time friend, and type favorite excerpts from the book you read – and everything would magically fall into place. Roam also has some more unexpected features, such as Kanban boards, Pomodoro timers, and programmable graphs.

The app gathered a massive following – check out the #roamcult hashtag on Twitter. Roam doesn’t have a mobile app yet, its web version is relatively slow – it might take 20 seconds to open it for the first time but even then jumping between notes causes a noticeable delay. It’s also the most expensive at $15 per month.

What Follows

Maybe at this point Roam Research doesn’t have as many users as other outliners but it definitely has the most vibrant community expanding its ideas and coming up with usecases.

I believe it’s going to be beneficial for the whole space:

• More users get the concept while not everyone might need a powerhouse that Roam is.
• Other apps see the outlining approach validated and new features proven useful.

The team behind Dynalist has already added backlinks to their core product and even launched Obsidian, their take on a knowledge management app that’s based on local Markdown files. Since it’s not an outliner I won’t be talking about it much but you can read some of my thoughts here.

In my mind, the perfect outliner should nail the core workflow, have stellar tagging and filtering views, but also enable quick entry from other apps and services, moving the nodes around through keyboard and native mobile apps. I imagine it to be a mix of Workflowy and something like Things 3 taking the best of both worlds. If you ever stumble on something like that please send it to me.

Superhuman is an app that has been reviewed and discussed from top to bottom, we’ve seen countless mentions of “Superhuman for X”, discussions of “consumerization of enterprise” and I saw Rahul Vohra’s Product-Market Fit score estimations in dozens of startups’ decks at this point.

But I always felt that one topic has remained largely in shadow: how Superhuman moved the Overton window of apps pricing.

A Bit of History

Back in the days software was quite expensive. The list price of Photoshop 1.0 for Macintosh in 1990 was $895 (that’s $1,767 in today’s dollars). In 2011 it was priced at $699. Not everyone paid those prices of course. I even had a theory that Adobe specifically wasn’t fighting the piracy of their products (their protection was very basic) for individual users because it acted as a top of the funnel. Teens would learn Photostop and Illustrator to draw and publish something on DevianArt. Some of them would become designers and come to a workspace expecting to see Adobe products there. All good! In comparison, local Adobe offices were pretty adamant about piracy at workspaces.

Generally, software was distributed via the sharewave model through various catalogs and websites. Even smaller utilies could cost $10/$20/$50 because not a lot of people would discover them in the first place and even lesss people would pay. “Professional” software was expensive but individual users weren’t the buying personas for it and the prices didn’t matter that much.

Then came the mobile. Apple AppStore redefined the pricing of mobile apps and games. Every month millions of people were buying new smartphones and becoming new users for the apps in the store. Trying to compete for them, the developers have driven the costs way down. Now people expected apps to be either free or a couple of dollars – $5 is already quite expensive!

But then somethign changed. The market has become saturated. People are still buying new phones, but less often – and they already have previous iPhones (or Android phones) and had the apps they needed. One-time small purchases were no longer able to drive the revenue.

Apple initially offered subscription pricing on AppStore in 2011 but only for content. Subscriptions for apps appeared in 2016. Meanwhile, Adobe switched to SaaS-only model in 2013.

Since then multiple old apps, including Fantastical, 1password, Ulyssess and many others have switched. Subscriptions incentivize developers to care about their existing userbase and provide recurring revenue to fund the development.

In 2016 Recode wrote that “The app boom is over”, an editorial in TechCrunch stated that “The air of hopelessness that surrounds the mobile app ecosystem is obvious and demoralizing”, and The Verge wrote that “the original App Store model of selling apps for a buck or two looks antiquated”.

Originally, the subscription pricing wasn’t that scary. Things 3 for iOS/iPadOS/MacOS costs a few years of Todoist Premium costs, which makes them relatively comparable. The developers weren’t ready to charge much more for consumer-grade software.

The New Age

Superhuman shocked a lot of people with its $30/month pricing for an email client (that’s $360 per year). I believe that this greatly extended the “Overton window” for consumer software pricing and enabled other companies to charge 2-3x more of what they initially did.

There have been a few email clients before that and most of their either:

• Were acquired by large tech companies for reasons unrelated to their core business [1], [2]
• Failed drastically [1]
• Were noticed selling insights based on users’ communications [1]

Turns out it’s very hard to make a good email client. Even while they were alive, most of those apps weren’t polished enough.

What if you can do a better job but need to charge more money? You probably need to ask if there’s a market for this. Designers would spend their entire days in Photoshop or Illustrator. There are different pricing plans, but a monthly single-app subscription is about $30. What if the user spends an entire day in email? Does it worth it? I guess so.

What’s even more interesting, such pricing allows the products that earlier could only be small utilities supported by indie teams turn into venture-backed companies. Regular pricing, especially one-time purchases, can’t really enable the margins and growth rate needed. You can think of Evernote that wasn’t able to recover to its early expectations.

Now we’re seeing dozens of old and new apps embracing higher pricing. One of the common aspect is that you can technically find more primitive ancestors for the newcomers that were simpler and charged less.

• Roam Research, a “a note-taking tool for networked thought” that became quite mainstream on Twitter recently, is touting a price of $15 a month as they come out of their current “early-access” status.
• Sunsama, a better task management and calendar app, is $20 a month ($16 with an annual discount).
• Fanstastical, a great email app for Apple’s platforms, used to cost $49.99 for a Mac app as a one-time purchase, now it costs $5 a month ($40 a year with an annual discount).
• Linear, a better issue tracker, is expected to be aroud $10/month when they come out of beta.
• Command-E, a less hacky Alfred for Mac, is expected to be aroud $10/month when they come out of beta.

If you have any other examples, please share, I’d be happy to add them.

What’s Next?

The tools we use in our digital lives are mostly subpar. They rely on the decades-old principles. Consumer software has been optimized for the mass user resulting in the lowest denomiator effects – Gmail is used by 1 billion people so it has to work for 1 billion people. Enterprise software instead has been optimized for entire organizations and the buying persona. The CIO might love the product but it’s not necessarily the best for individual contributors.

There are now two combining effects: the widely discussed consumerization of enterprise, meaning that software is adopted bottom-up and optimized for the experience of individual users, but also the expanding realization that companies can charge way more for personal productivity tools – and use that revenue and expectation to build better tools.