Slopes started as a paid up front app, because that's how you "did" apps. $3.99 -> eventually $7.99. The price tag was really hindering growth and I was having to spend a lot of time convincing people to download the app and try it (and once they did, they loved it). I was getting tired of the struggle, and figured I needed to change something if I was going to really have a go at making this app my job (I was split between Slopes maybe 30% of my time and consulting for the rest). To date Slopes had only made a total of $11k in the two seasons it had been around.
Paid up front just wasn't working.
So I spent the summer of 2015 moving Slopes to the freemium model and a $19.99 subscription. Back then, a lot of apps were still pay-once. Some early fitness apps having yearly subs, but not many others. My big a-ha that made me feel OK with the move, beyond wanting to make a serious go at this, was in the name of the sub - "Season Pass".
That was a lesson that has stuck with me: my niche, the ski market, already has established ways of doing things. The more I aligned with them, the better.
But it was still tough. Figuring out the right paywalls to put up was a struggle (one I still question). I had seen at least one competitor give away way too much for free, and I saw their revenue struggles. But I also had to balance that against my user-self that didn't want to be unreasonable.