First: I planned on delivering outside the Mac App Store. This involved updating via the Sparkle cocoapod framework and fulfillment through Stripe. What I found was that the whole process, from downloading and getting going to paying, was very high friction. Every middleman was scaring the potential user: Chrome would warn about the .zip file. MacOS would warn with a scary dialog (even if the app had been notarized). As someone who is wary of downloading apps off the internet, it crossed the line from what I would have done.

I'm also a one-man shop, so I was spending an inordinate amount of time working on fulfillment infrastructure, not improving the app itself. Enumerating other considerations: outside the store I'd have to know more about my user (a bad thing for me since I'm privacy-first), the long-term drain on resources (time and server costs) is higher, system complexity is way higher than through store.

You can always decide to launch outside the store at a later point in time if it's justified, and i've already round tripped the fulfillment process, so that wouldn't be too hard to roll out. All that said, I decided to target an App Store launch in early February.

Next up: I implemented Free Trial. Users would have 14 days to try the entire app for free, then have to make a decision. Ultimately, this also proved high-friction because Apple requires users to "Buy" (not "Get") the free trial as an in-app purchase before they could start using the app, which meant another ~90 seconds and potential confusion on the user's part before getting to try the app.

I landed on freemium for a few reasons: 1.) I know the basic free app can stand on its own as something users would enjoy, 2.) it was frictionless for users to get started, 3.) the install base would be higher because there's no "buying cliff", 4.) it allows me to package two completely different power user sets into distinct upgrades-and therefore, hopefully, capture more total value.