Building for Software Appreciators

Product lessons from the nth calendar app

Why do people keep making new calendar apps? And I'm not talking about CS students trying their hand at a first React.js application (been there, done that). I'm talking about talented, proven entrepreneurs who appear to be violating every startup 101 rule by building commodity software in a crowded category to try and win a fraction of a market dominated by, let's double check, yep, Google and Microsoft! It's no surprise these apps rarely bring something genuinely new to the table. Calendars, and many other kinds of personal productivity software, are just too damn simple to inspire net new software experiences.

The calendar app is the jazz standard of web software—it's exciting to find a fresh take on an old classic, but nobody expects to top the charts with Autumn Leaves. But year after year comes the familiar tune of a buzzy Product Hunt/Twitter launch and a TechCrunch article about a new calendar startup, freshly funded by intelligent and capable VCs, ready to take on the world. What gives?

I know it sounds like I'm being a hater right now. But actually, I love new calendar apps! I've probably gone through five in the past two years (as a paying user, even) and probably will go through five more in the years to come. I don't expect each new app to be noticeably better than its predecessors—it's just really fun to use them all. And there are a growing number of people just like me. This cohort is interesting to consider because here the conventional wisdom about software market dynamics begins to break down and lose its explanatory power. I'll illustrate this by distinguishing two made-up groups, "software users" and "software appreciators".

Software users are normal customers in a consumer or B2B context. They care about what software does more than how it does that thing. They have a problem and look for software that solves it effectively and to the extent that it's possible, invisibly. Software users are the customers that you're supposed to build for. Software appreciators, on the other hand, may not have a "problem", or the problem might already be (mostly) solved. Software users are not merely trying to extract utility from a software experience because, for them, the experience can be an end in itself. When you build delightful UX into your product for software users, it's a subtle, subconscious trigger that improves your retention curves. Software appreciators notice it consciously and choose your product because they hope you can provide those delightful moments in spades.

Appreciators are not quite the same thing as power users, though they usually overlap. Appreciators see the software experience as a work of art more than as providing a function. Personal productivity apps like calendars tend to attract them more than any other category because the old advice that "the best notes app is the one you use" is true! With a basic solved-problem functionality as table stakes, it's the cherry on top that sells the milkshake. These products exist in a market where Hotelling's Law has long since run its course, and they can no longer differentiate on the features that make them valuable as consumer utilities. So they develop diverging feature sets, generally with small UI/UX changes, that appeal to the mercurial appetite of the software appreciator.

This is a cyclical process—the apps add new capabilities and easter eggs right up to the point that a new competitor emerges with a minimalist landing page and a "back to basics" product ethos. To be clear, even in these markets, software appreciators are a tiny subset of software users. But they form a vocal minority of true evangelists, and their obsession with tiny details that no normal customer would notice can bubble up into momentum that gets the app reviewed by the Ali Abdals of the world and thrust into the mainstream. That's the bet that everyone building these products is making; build for software appreciators and the users will come.

So why is this phenomenon interesting, beyond a quirk of some niche software markets? Because there is a real chance this strategy will become increasingly important as a result of two tailwinds: Internet Nativity and Generative AI. Being a software appreciator, like being an art critic, requires immersion. To understand why the keyboard shortcut in xyz calendar app is so awesome, you have to have tried out the other 10 apps that don't have it. And so it is with all other software products. An increasing percentage of the Internet software market is comprised of people who have spent their entire conscious lives using software. Today's iPad kids are tomorrow's tech employees—these people will have taste in software that many of us haven't the palate for. They will have opinions about niche details the average user ignores today because they experience software with higher fidelity. The internet isn't a second language for them; they will expect more from it, even at work.

Generative AI, on the other hand, is already changing the way we build products. The tldr is that it makes software a whole lot easier to make, and make quickly. It will be harder and harder to build a utility feature moat if your competitors can replicate it with a junior engineer and GPT-N in the afternoon. So products will be forced to differentiate on the dimension that can't be copied so credibly: style. GenAI may also make it easier to switch between providers (because LLMs make arbitrary data transformations trivial), so the future of all kinds of software products, not just calendars, maybe more similar to the fashion world than the internet boom. Even big companies with huge market caps may tend towards constantly cycling styles, remixing retro themes, and making very opinionated design choices.

If text is truly the universal interface, I think we are rapidly approaching a day when most apps can do most things. You'll probably be able to ask your CRM which part of the codebase a qualified lead's request would most directly impact, or do cohort analysis from your IDE. So the best teams will build for the software appreciators, who grow in number each year.

This post was inspired by the launch of Amie, a new calendar app. The landing page has some flashy and unnecessary animations. It's got bubbly fonts and a friendly feel, and makes it 5% easier to schedule a meeting. It integrates with the standards tools you'd expect it to. As far as I can tell, I replicate all of its features directly in Google with a single extra click maximum. But of course, I tried it, absolutely loved it, and immediately downloaded the desktop app and dropped the iOS widget into my home screen.