Why 'free' proprietary software will always end in tears

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Nearly every day, my kids come home from school and go on about some new app or game they and their mates are excited about. My younger boy invariably looks at me when he says "and it's free!" hoping that I'll smile back, but I say, "cool. I wouldn't use it". He's crestfallen . "But why!?" And... I have to pause and think and eventually I say, "well, it's kinda hard to explain". But there's an oft repeated pattern here, so I'm explaining it now, for future reference, with this story.

A while back, I ran a scout group. The national scouting body decided to launch a new "Scout Management System" that we were required to use for everything from organising meetings and recording attendance, to health-and-safety checks and risk registers, to paying dues, sign-ups and managing leaders and adult volunteers. Unfortunately, it didn't work. At all. It was the worst software implementation process I've ever seen, and I've seen a lot in my career so far. Most of the leaders (myself included) did everything possible to avoid using the system.

My fellow leader, a die-hard Apple fan, said "hey, my kid's football (soccer for you North Americans) team uses this app called Heja to coordinate practices and stuff. It's free! Let's just use that instead."

I felt bad about being negative but I advised him, and the others, against adopting Heja. Here's how I explained why I was pissing on his bonfire:

How proprietary web services work

The joyous introduction

Heja is a nice app. It has a hip website, with almost unbearably cool founders and happy looking developers and marketing people - it even has an 'onboarding team' and 'experientialists' whose job it is to make joining Heja an unmitigated joy. Heja's development is funded by generous Venture Capitalists (VC) - wealthy business investors - who forwarded Heja's owners $6 million to build the product.

Heja have adopted a common business model for this sort of 'Software as a Service' (SaaS) application: offer a 'free tier' service that's quite compelling and useful. Get a lot of people using Heja and spreading the word about how useful it is, roping in new people all the time because it's easy to get into and "it's free!"

Organisational dependence achieved

The community organisations these enthusiastic Heja users run progressively build Heja into their organisations' communications structure. Eventually, it becomes a mission critical dependency on they way they function. People who can't run it, like due to an outdated or incompatible phone, are out of luck. Some end up buying a new phone just so they can participate. The organisations write stuff like helpful 'how to' guides for new organisation members carefully documenting the process of installing Heja and all the ever-expanding modes of using it for crucial activities.

Return of the VC

Then, at some point (as is guaranteed to happen) the VCs tells the good folks building Heja "you've had long enough 'developing' your product. Now we want that return on our investment you promised us when we gave you the money." Ah. Right. That. Gulp.

Progressive enshittification

Heja really only has one option: they will start reducing - probably gradually at first (so as not to spook the horses) the elements of the service available under the 'free tier'. Heja will trumpet all sorts of 'enhancements' to the app. Users will be very excited... but then things your organisation used to do no problem will suddenly be met with a jaunty message: "upgrade now to Premium Heja to undertake [task name]"! They'll have a per-organisational fee per month or year (with maybe a 15% discount for an annual subscription instead of month-by-month).

Hey Heja angry! We used to do that for free. Now all our parents and kids are using your service. You want how much per user per month for the 'Premium' version?!!! That's 10 times more than our organisation's annual budget!?

But now it's too late. The total upheaval of having to find and switch everybody to a new system... and then rewrite all of those helpful documents... ugh. No, we'll use Heja to coordinate an emergency payment by all parents to upgrade to Premium Heja. And they've got you. Hook. Line. And. Sinker.

What you're seeing is so predictable and ubiquitous that it's got its own name "platform enshittification". Cory Doctorow coined the term in a January 2023 blog post, characterising it like this:

Here is how platforms die: first, they are good to their users; then they abuse their users to make things better for their business customers; finally, they abuse those business customers to claw back all the value for themselves. Then, they die. I call this enshittification, and it is a seemingly inevitable consequence arising from the combination of the ease of changing how a platform allocates value, combined with the nature of a “two sided market,” where a platform sits between buyers and sellers, hold each hostage to the other, raking off an ever-larger share of the value that passes between them.

If I was just a parent of a kid or two on the team, I'd be pretty dark about having to pay that unexpected expense (with a prospect of paying it again next month or next year!) given that adopting Heja was the organisation's choice, not the parents' - we weren't consulted or warned that this might happen.

Note that proprietary software developers - who exert total control over their software - have a myriad of ways to subtly  enshittify your experience of their 'free tier' and badger you into buying the premium version. They can reduce your ability to access or export your own data in their system (holding data hostage - indistinguishable from ransomware) or collaborate with others, or any number of other - often seemingly insignificant - arbitrary limitations... until you want or need them.

And, of course, these proprietary services also have other, unexpected, ways to make your life a bit miserable: their leadership might be too kind to enshittify their 'free tier'. Then their VCs will either replace that leadership with someone far less kind and more committed to achieving their expected return. Or they might go out of business altogether. Often quite suddenly. Or they might be acquired by a bigger player which will either lead to accelerated enshittification or EOL'd ("End of lifed") for 'strategic reasons' (folks who used Github's open source Atom IDE will know what I mean - Microsoft EOL'd it in favour of its own fauxpen source Visual Studio Code IDE upon acquiring Github).

How it plays out

Well, this is awkward

Heja will very carefully make the amount an organisation has to pay just enough to feel quite uncomfortable, but just low enough that, despite sharp intakes of breath, 80% of existing 'free tier' customers will grudgingly pay for what they previously got for free, because switching to something else will be extremely costly and a major hassle that will lead to organisational breakdown similar to what that horrible Scout Management System has done to the volunteers that really power ScoutsNZ.

20% will deem it too much and abandon the platform, but will then have to scramble to find another communication platform, causing similar pain and chaos within their organisation. Most will unwittingly wind up in precisely the same situation again with some other nascent proprietary SaaS app and will go through a similar upheaval in a year or two. I've seen this sort of thing play out many times over the past 30ish years.

The alternative path

The way to nip this vicious cycle in the bud is to not use a VC-funded profit-motivated startup's proprietary product. That is what, for example, Signal isn't. The key parts of Signal were created by some of the same people who created WhatsApp, now owned by Facebook, which reads every message sent despite touting end-to-end encryption... because Facebook owns & controls the client software at each end, (and you know what that means, right? Yup, full exploitation to maximise shareholder value) and uses it to build advertising profiles for each user which it sells to advertisers, making it many $billions in profit each year.

Signal was the developers' attempt to do WhatsApp one better. It's an interesting story - Signal's also end-to-end encrypted. And its developers decided to make it open source. And it doesn't cost anything - yes, "it's free", too. But they support it with a charitable organisation rather than a VC-funded 'startup'. I recently gave them a modest donation because I value their service and want to see it continue. Luckily, the main beneficiaries of the sale of WhatsApp to Facebook also underwrote the charity's endowment. It's fundamentally different model. An entirely better one, with far more virtuous incentives. It also produces extremely good software, a rare app (in both proprietary and open source worlds) because it's actually very well regarded for its usability.

I suggested to my fellow leader that instead we could instead adopt Signal - it does almost all the same stuff as Heja, and more besides. But my fellow leader knew Heja and didn't know Signal. He wasn't swayed by my explanation.

So they decided to adopt Heja.

Shortly after, coincidentally, my boys decided they'd had their fill of Scouts and decided to stop, allowing me to disentangle myself as well... but I remained on a few email chains and am friends with many of the leaders.

I've already heard that, as I predicted, the screws on functionality available in the 'Free tier' are being tightened, and stuff that they used to do now kicks up a "this is a Premium feature". For now, they're just avoiding those things (using ad hoc email to fill in the gaps). But the die is cast.


Earlier today, as I was sporadically writing this post, I saw a social media post (on Mastodon, dontchaknow) from a former colleague. They'd just used SurveyMonkey to send out a time-critical survey for prospective attendees of a conference they were organising... using the 'free tier' (which they'd apparently done plenty of times previously). They were cussin' because, having sent out the survey and received notifications of a good response, when they went to the results, they found an unexpected limitation: they could only view the 'first 10 responses' under the free tier. To view more, they'd have to upgrade to the premium version.

Oh dear. As you can imagine, I was shocked.

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