iFilesNine years, a million downloads, and learning what I could charge for
iFiles has been on the App Store for nearly a decade. In that time I tried three different ways to make money from it โ and users taught me, three times over, exactly what a tool app is not allowed to charge for. This is the honest version of that story.
The week I launched, Apple showed up
On September 19, 2017, iOS 11 shipped with Apple's own Files app. Eight days later, iFiles 1.0 passed review. I had spent a long time building a file manager, and a week before it launched, Apple made "file management" a system feature.
It sounds like a bad joke, but back then putting a movie or a PDF onto an iPhone was genuinely painful โ the standard move was to plug into a computer and dig through iTunes file sharing. iFiles was built around that pain, and soon after launch I added Wi-Fi transfer: the phone becomes a little web server, and any browser on the same network can upload and download without a cable. In the era of "plug in and open iTunes," that felt like magic.
Riding on the system's back
Over the next two years the Files app grew stronger with every release. Fighting a system feature head-on is a losing game โ Apple doesn't need to beat you, it just needs to absorb your core feature in the next update.
So I made a directional decision: don't fight the system, ride on its back. I rebuilt iFiles on Apple's document-based framework so files stayed fully visible and interoperable with Files, and I focused on the two ends the system did poorly โ getting files in (Wi-Fi, AirDrop, camera, share sheet) and opening them well (play video without converting, read PDFs and Office docs, unzip archives). That positioning is what kept iFiles alive.
Three times I tried to charge, three times I got it wrong
First came a splash ad โ everyone had one back then, and I had hundreds of thousands of users. The complaints came fast: a quiet tool users had trusted for years suddenly interrupted them. Fair enough. I pulled it.
Then "pay to remove ads." It reads reasonable on paper, but it meant I had first made the app worse and then asked users to pay to undo it. That doesn't sit right either.
The third time, in early 2026, I put the most-used feature โ Wi-Fi transfer โ behind a paywall. It worked: real money came in every week, the closest this app had ever been to paying for itself. And the one-star reviews arrived just as fast. One stuck with me: after all these years, charging for it out of nowhere โ that's just greedy. I stared at the rating curve for a long time, then took the paywall down.
What users were really telling me
The lesson wasn't "users won't pay." It was: you can't charge for value people already had for free. Wi-Fi transfer had been free for years โ turning it into a toll booth felt like betrayal, no matter how gentle the price. "Greedy" wasn't about the money; it was about the move.
So I wrote it into the project as a hard rule: file management and Wi-Fi transfer stay free, forever, in every future version.
The fourth attempt โ this time, no backlash
If not the old value, then the new. The tools I added after the rewrite โ document scanning, web-page-to-PDF, photo metadata (EXIF/GPS) cleanup, PDF merge/split/compress/password, ZIP, a Face ID vault โ none of these existed before. Each one you can try free, in full, once. If it's useful and you want to keep using it, that's when Pro comes in.
The trial is a real trial, the paid boundary is clean (the "save" step of a tool), and nothing old gets touched. Revenue is still modest โ I won't pretend this is a financial-freedom story. But two things changed for real: the one-star reviews stopped, and the people who pay are happy to.
Nine years, four attempts. The first three taught me what I couldn't charge for; the fourth is the first that felt fair to everyone. iFiles is still free to browse files and transfer over Wi-Fi โ try it, and if the deeper tools earn their keep, Pro is there when you want it.