The Problem with Modern SaaS
I'll use Calendly as an example because that's where this started.
Calendly does one thing: it shows people when you're free so they can book time. If you want to charge me $20/month for that, you better be solving every single calendar problem I have. But Calendly doesn't. I have a personal calendar, a work calendar, and a family calendar. It couldn't connect to all of them. So I had conflicts. One job — and it couldn't do it right for my setup. Ironically, Calendly doesn't even have a calendar view.
It gets better. I was paying $20/month for Calendly's "Professional" plan. They quietly restructured their pricing, replaced it with a $12/month "Standard" plan that has nearly the same features, and kept charging me $20 on the legacy plan. The one feature I'd lose by downgrading? Routing forms — a sales team feature I never used. I was overpaying by $8/month and had no idea, because who audits 15 different SaaS subscriptions every month?
Instead of solving calendaring, they've given me a recurring mental load problem around calendaring. Legacy plans, plan restructuring, quiet price increases, features gated behind tiers you don't need. You came to them with one problem — "let people book time with me" — and now you have three: the calendar still doesn't work right, you're overpaying, and you're too busy to deal with either.
Here's what 25 years in this industry taught me: every codebase is full of tech debt. It's an industry-wide problem. Unless someone goes out of their way to consistently eliminate it, it's everywhere. Those large engineering teams at Calendly? A good chunk of them are managing their own mess. And you're paying for it.
And then there's lock-in. Try leaving. Export your Calendly booking history — your scheduling patterns, your meeting notes, your integrations. They make it easy to get in and hard to get out. That's not a partnership — that's a trap.
It Costs Too Much
If Calendly charged $4/month, I never would have built this. A booking page is worth maybe $3/month plus a reasonable margin. Fine. But they were charging me $20. They quietly restructure pricing, grandfather legacy plans, and count on you not auditing. Now why is LastPass charging me $3/month for something my browser does for free...
It Doesn't Do What I Need
It couldn't connect to all my calendars. I had conflicts. And the irony of a calendaring tool not having a calendar view is astounding. You can't make this stuff up. When you hit an edge case, you file a ticket and wait. Or you work around it. Or you leave. There's no option to just fix it yourself.
Privacy Is a Marketing Word
"We take your privacy seriously" is on every website and means nothing. So instead of saying it, we show you exactly what the server can and cannot read. Your vault passwords? Zero-knowledge — we can't read them. Your calendar? We can — and we'll tell you that. Delete means DELETE. Export means everything. Transparency over trust.
The Economics Have Shifted
Building good software is much easier than it used to be. It used to require a whole team of A-players to have a chance of getting it right. AI changed that. Teams can be smaller now. More opinionated. The companies behind the software can be smaller and less dependent on growth. One engineer with AI can build what used to take many — and you own it forever. No subscription fees. That's why the economics shifted.