I came across a lovely article today about something I had almost forgotten about: shareware (https://deadparrotbbs.com/what-happened-to-shareware/). And reading it brought back quite a few memories.
For anyone who started using computers a little later: shareware was basically software you could download, install and actually use before deciding whether you wanted to pay for it. Sometimes the free version had a nag screen. Sometimes a few features were disabled. Sometimes you could use almost everything and the developer simply trusted that, if you liked the program, you would eventually send some money. It was a wonderfully simple arrangement: here is my software, give it a try, and if you like it, please pay me.
I tried a lot of it
I used a lot of shareware over the years, especially during what I like to call my “Windows days.” And I bought quite a few programs as well. That was part of the fun of having a computer at the time. You would come across some little utility, download it, install it and see what happened. Perhaps it solved a problem you didn’t even realise you had. Perhaps you used it for ten minutes and deleted it again. Or perhaps it became one of those programs that stayed on your computer for years.
Some shareware became enormously successful. Programs such as PKZIP, WinZip, Paint Shop Pro, Total Commander and WinRAR all came from, or were closely associated with, that world. Games such as Doom and Wolfenstein 3D used variations of the same idea.
But the really interesting part was not necessarily those famous examples. It was the enormous layer underneath them: small programs, often written by one developer or a tiny team, designed to do one particular thing. An archive utility archived files. A graphics program edited images. A disk utility did something useful with disks. There wasn’t necessarily a cloud platform, an account, a dashboard and three subscription tiers attached to it.
Then software changed
The article I read does a good job of explaining why that world largely disappeared. Software distribution became more centralised. App stores made installing software easier and safer. Security became a much bigger issue. Payment systems changed. And, of course, subscriptions became an increasingly common business model. There are perfectly good reasons for many of those changes. Downloading random executables from unknown developers isn’t necessarily something we should romanticise too much.
But something was lost as well. Shareware made experimenting incredibly easy. You could try ten programs and perhaps keep one. You didn’t necessarily need to create ten accounts, enter your credit card details ten times or remember to cancel nine trials before they automatically turned into subscriptions.
And if you bought a program, it often simply became your copy. It sat on your hard drive. As long as your computer and operating system continued to support it, you could continue using it. I miss that sometimes.
Could we bring that world back?
That made me wonder whether it would be possible to recreate something similar today. Could we have another period in which people constantly experiment with small pieces of software? Where independent developers build strange, useful and very specific tools, put them online and invite people to play with them?
In some ways, I would love that. But then another thought occurred to me: perhaps we already have it. Only this time it looks completely different.
Enter vibe coding
Vibe coding changes the equation in a rather fundamental way. Instead of searching for a tiny utility that does exactly what I need, I can increasingly try to build that utility myself. That is quite a remarkable change.
During the shareware era, the excitement was often about discovering software somebody else had created. Today, part of that same excitement comes from thinking: could I make this myself? And then you open an AI coding tool, describe roughly what you have in mind and start experimenting. The first version probably doesn’t work. The second version works but does something ridiculous. The third version almost works. And suddenly, an hour or two later, you have a little tool that actually solves your problem.
In a way, that feels surprisingly similar to the old shareware spirit. Not because the technology or business model is the same, but because the barrier to experimentation has become low again.
Local first makes it even more interesting
There is another development I really like: local-first software. Instead of assuming that everything has to live in somebody else’s cloud, local-first applications put your data primarily on your own device. The cloud can still be useful for synchronisation, collaboration, or backup, but it doesn’t necessarily have to be the center of everything.
Combine that with another idea I find fascinating: malleable software. Software doesn’t necessarily have to be a finished product that somebody else designed and that we simply have to accept. It can increasingly become something we adapt to our own needs. Change the interface. Add a function. Connect two tools. Write a small script. Ask an AI coding assistant to modify something. Fork an open-source project. Build a tiny application around your own workflow.
In other words, instead of choosing between ten pieces of shareware, perhaps we can increasingly create number eleven ourselves.
Maybe I don’t really want the old days back
So yes, I am a little sad that shareware has largely disappeared. There was something wonderfully straightforward about downloading a small program, trying it and deciding afterwards whether it was worth paying for. And I still think there is room for software sold that way. In fact, parts of the model still survive in indie software, games, open-source projects, perpetual licences and applications that offer proper trial versions.
But perhaps nostalgia can sometimes make us overlook what is happening right in front of us. The shareware era gave ordinary computer users an enormous playground. There were thousands of programs to discover, test, break, remove, reinstall and eventually buy.
Today that playground may actually be much bigger. We have open source. We have GitHub or even better: that wonderful site called Codeberg (https://codeberg.org/). We have local-first applications. We have APIs. We have small local language models. We have increasingly powerful coding assistants. We have vibe coding. And we have this emerging idea that software itself can become more malleable — something we don’t just consume, but can reshape.
So perhaps the conclusion shouldn’t be that everything was better during the shareware days. I loved shareware. I tried lots of it. I bought quite a bit of it. And I genuinely miss that culture of casually experimenting with small pieces of software. But I am even more excited about what is happening now. We did some wonderful and interesting things with computers back then. Today, we can do even more.
Oh and just one more thing: did you notice the name of the website where I found the article about shareware? It’s called Dead Parrots BBS. Now that really does sound like a name straight out of the old days!



