Last Christmas, my wife bought our 5-year-old daughter a Yoto player. To explain to those unaware - it’s essentially a music player where you have to purchase NFC cards that, when inserted into the player, will then stream the music to the device that was unlocked by the card. So, instead of streaming “Let It Go” on Spotify using a subscription we’re already paying for, we needed to purchase the “Frozen” NFC Yoto card that unlocked the ability to stream the album on the device. It may sound like I’m making it seem like it’s a cash grab, but that’s because it is. Anyway, this article isn’t about the Yoto.
My eight-year-old son, like most siblings, wanted what his sister had. There was no way I was spending $100 on yet another gimmicky music player, so I told him I had a device I could give him that did the exact same thing: an iPod.
Ah yes, my old iPod Classic 120GB, loaded up with the music I listened to in my teens and twenties, had been sitting in one of my desk drawers with a dead battery for over a decade. I figured I would just charge the device, load it up with some of his favorite songs, and let him experience the joys of the click wheel of the early 2010s.
Simple enough, except it turns out modern Macs can no longer talk to older iPods properly. iTunes has been replaced, the old MacBook that synced to the iPod originally is gone, and though there is a manual process of extracting the songs individually, the filenames were obfuscated and it was immensely time-consuming for the number of songs I had on the little device.
So I did what I usually do when I have a problem: I went looking for software to solve it. There were plenty of options; several apps that promised to pull music off an old iPod, rename the files properly, and organize everything into a usable folder structure. But almost every one of them was shareware. Thirty songs free, then you hit a wall and buy a license. Some were $20, some were $30. One wanted a subscription.
Then I remembered that I had a Claude subscription, so I thought I could do better.
Five Minutes to Build
I opened Claude Code and described what I needed: an app that could connect to the iPod, extract all the tracks, rename them using the embedded metadata, and drop them into a folder organized by artist and album. Basic stuff, but tedious to build from scratch. It took about five minutes to get something up and running.
Then I plugged in the iPod and let it go. Forty-five minutes later, every track was sitting on my desktop, named correctly, organized the way I wanted, by artist and album. I had my music and my son had his iPod.
And then I deleted the app, because I only had to use it once and was done with it.
The Shareware Bargain
Shareware worked because building software was hard. A developer had to recognize that there was a problem many users had, solve it, package it, and get it in front of the people who needed it. If they charged $20 for that, the math made sense. You paid once, you used the tool, everyone moved on.
The trial limitation made sense too. Let users try it, cap the free tier at something annoying enough to push them toward buying, and collect license fees. It was a reasonable way to fund a small developer doing useful work.
The whole model depended on the assumption that building the alternative yourself was not a real option. Most people can’t write code, and even people who can write code don’t want to spend an afternoon on a one-off file extraction utility. So you paid, because paying was cheaper than the alternative of doing nothing or figuring it out yourself.
The New Math
I am first and foremost a data guy. While I can code in Python and Go, and I’m picking up a bit of Rust, I would not consider myself a software engineer. I was also certainly not going to sit down and spend my entire weekend writing a Python script with proper iPod filesystem handling and metadata parsing.
What’s fascinating to me is that I don’t have to put up with shoddy freeware and shareware apps anymore. I describe the problem in plain English, Claude Code writes the solution, I test it, we iterate, and I have something working faster than it takes to evaluate the shareware alternatives. The barrier used to be skill, and now it’s closer to fifteen minutes of conversation.
The shareware model basically bridged a gap in the market where your need was real enough to matter but niche enough that not a lot of solutions existed for it. For complex software, there might still be a market. But for the category of “I need a utility that does one thing, I’ll use it once, and then I’m done,” that gap has essentially closed.
Who Pays for Shareware Now?
This isn’t a prediction about all software. Subscription tools, platforms, things you use every day with ongoing development and support, those still make sense to pay for.
But for narrow utility software that solves a specific, time-limited problem, the paying audience just got much smaller. Think about the person who needed an iPod extraction tool before me. It was a niche problem (people use phones for their music players these days), limited options, $25 price tag that felt annoying but acceptable. Enough people like them paid that a developer could build it and make money.
Now those same people have an option that didn’t exist two years ago. Describe the problem, build the application, use it, and then remove it. The developer who built that shareware did nothing wrong. They built something genuinely useful and priced it reasonably.
Where That Leaves Small Developers
Small utilities have always been a thin business, and the market was never huge. What’s shifted is that vibe coding gives the people who have the problem a way to solve it themselves, without a developer in the middle.
There are still things worth building and selling: enterprise software with dedicated support, applications that take sustained effort to get right, tools where the developer’s ongoing judgment is part of what you’re paying for. But the closer your tool is to a one-time-use script, the harder it is to charge for it now.
So, what happens to these shareware developers now? I have no doubt they’re also vibe-coding their way into other projects. It’s quite unlikely those apps were ever generating sustainable revenue anyway. My guess is most devs have turned their endeavors into open-source projects.
For now, the iPod is charged and sitting on the desk, ready for my son. I also lied about deleting the app. Like any good developer, I open-sourced it and made it available on GitHub: https://github.com/hyhenry/ipod-music-extractor
You’ll probably never use it.