Frank and Sanne break down why SaaS subscriptions are quietly draining your wallet, and why Claude, open-source tools, and a willingness to clean up your data might be the exit ramp.
Moneybird sent Frank a cheerful anniversary email. Ten years as a customer. And, by the way, the price is doubling in two weeks. Fifteen euros becoming thirty. An invoicing tool he uses for one purpose: making invoices. That email is what kicked off a conversation that kept circling back to the same uncomfortable truth: a lot of the software people pay for monthly has quietly gotten worse while the price has quietly gone up.
There's a term for this, coined by writer Cory Doctorow: enshittification. It describes how digital platforms and services start out genuinely useful, then gradually degrade as the pressure to extract more revenue overrides the original reason the thing was built. Frank and Sana spent a good portion of their conversation testing the word out loud, debating whether it was real ("It's a coined term rather than a traditional dictionary word," their AI assistant Perplexity helpfully clarified), and then agreeing it described pretty much everything they were frustrated about.
Enshittification refers to the process of a product or service gradually getting worse over time — platforms decline in quality due to profit-driven decisions that prioritize monetization over user experience. "Enshittification refers to the process of a product or service, especially online platforms, gradually getting worse over time. It's basically describing how platforms decline in quality due to profit-driven decisions." — Perplexity AI
Dropbox came up as the clearest example. Frank uses it heavily for video editing work, which means large files, often on the road. A few years ago it was rock-solid. Now, files get offloaded to the cloud automatically, and if you're on a plane with 100 gigabytes of footage that's been quietly pushed online, you're stuck. The workaround — right-clicking every folder to "keep downloaded" — is exactly the kind of friction that signals a product losing its way.
The underlying business logic isn't hard to read. If Dropbox can nudge you to store more (they now prompt you to back up any external SSD you plug in), your storage fills up, you hit your limit, and you upgrade your plan. The incentive to help users manage their data efficiently runs directly against the incentive to sell more storage. So the product drifts toward the latter.
It's definitely enshittification if you compare it to how robust the product was five years ago.
For lighter users, Dropbox still works fine. A few PDFs, occasional sharing, no complaints. But for anyone doing serious work with large files, the experience has slipped noticeably, and the price has not.
The deeper problem is how these costs compound. Dropbox. Moneybird. Adobe. Microsoft 365 with a terabyte of OneDrive nobody uses. Netflix. Each one feels manageable month to month. Added up across a working life, Frank's rough estimate lands at a thousand euros a year going to tools that have either gotten worse, are underused, or both. Over ten or twenty years of a professional career, that's a significant sum flowing toward services that weren't designed with loyalty in mind.
The goal is to save a thousand bucks a year — in 10 or 20 years of your professional life, that's a lot of money going to enshittification companies.
The response Frank has started taking is to replace paid SaaS with open-source or self-hosted alternatives wherever possible. He rebuilt his own website in a JavaScript framework Claude helped him choose, replacing a managed WordPress service that cost several hundred euros a year. The new version costs about fifty euros annually. He then did the same for Sana's photography portfolio, finished in under half an hour, with a setup where she can hand Claude a batch of photos and ask it to add a new gallery in the same style as existing ones.
The invoicing situation is next. He's actively looking for an open-source alternative to Moneybird. Not because he's unwilling to pay, he's clear about that, but because a 100% price increase for the same service crosses a line.
This is where the conversation about AI tools gets interesting. Frank uses Claude Code specifically because it can run tasks in the background across multiple sessions simultaneously. While one session works through a problem, he can open another and start something else. It's also what let him build a small app to control the ISO on his Blackmagic cameras remotely over Bluetooth, which he casually demonstrated mid-conversation by dimming the studio cameras.
The broader point he keeps returning to: as AI agents get better at building functional tools on demand, the case for paying monthly for off-the-shelf SaaS weakens. Why pay for a subscription to software that does 80% of what you need, in a degrading way, when you can ask Claude to build the specific 20% you actually use?
Sana's use of AI is more conversational and immediate. She throws festival lineup flyers into ChatGPT and gets back clean, formatted text she can copy directly into her advancing notes, saving the error-prone work of transcribing times and names from an image. She also uses it as a thinking partner for tricky emails, particularly useful when she's dealing with contacts in Japan, where Dutch directness can read as bluntness and a softer tone matters.
The Dutch are notoriously hard and straightforward. I think we can learn a thing or two from other cultures.
She started using AI to improve her English business writing a few years ago, and that particular use case has mostly run its course: she can do it herself now. But for those moments when she's busy and firing off a quick email that comes out too clipped, she still asks it to soften the tone. Frank, meanwhile, asks it to do the opposite: cut the fluff, get to the point.
The conversation took a useful detour into data storage and why people accumulate so much of it. Sana's argument: you should go through your files regularly, delete what you don't need, and stop buying more storage as a substitute for curation. Frank's counter: the math doesn't really work that way.
He's got 8.5 terabytes of documentary footage from a Norway shoot that a filmmaker later reached out about wanting access to. Deleting a thousand phone photos might free up a gigabyte. The Norway footage, untouched, is orders of magnitude larger, and actually irreplaceable. The comparison to cleaning out a closet breaks down when you're comparing boxer shorts to a full snowboard kit. Or, in his words, when one item in the closet is worth keeping and takes up the space of a thousand of the others.
The conclusion they landed on: yes, you should clean up your data. But the reason data centers keep expanding isn't that people are hoarding duplicate selfies. It's that genuinely valuable, large-format files accumulate, storage gets cheaper, and the path of least resistance is always to buy more space rather than to audit what's there. Which, of course, is exactly what Dropbox and iCloud are counting on.
The episode ended with a live experiment: can you use Apple's Pages to collaborate with someone on Microsoft Word without it becoming a mess? Perplexity walked them through it in real time. Pages exports cleanly to .docx. A Word user can open it natively, edit it, add pages, save it as .docx, send it back. Pages opens that updated file directly, no re-exporting needed. The .docx format is effectively the shared language both applications speak.
The one thing Word offers that Pages doesn't, according to their AI assistant, is Copilot integration and a more robust commenting system with permission controls. For most everyday documents, that gap is narrow enough that switching is plausible, especially if it means getting off a Microsoft 365 subscription you're only using for Word and a terabyte of OneDrive storage collecting dust.
The broader challenge Frank floated at the end: run a systematic experiment, tool by tool, and find out what you can replace, what you actually need, and what you've been paying for out of inertia. The subscription economy has been very good at making that inertia feel normal. Enshittification, it turns out, only works if you stay subscribed.
