Overcast Tries Ads
If any new patron-only features are widely demanded, I’ll be stuck with the year-one problem again. If not, they won’t bring in enough money. The latter is more likely: what most people want (and will pay for) is pretty well covered by Overcast’s current features.
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Charging money only works in scarcity, but most kinds of software are no longer scarce, especially on iPhone. Whatever I charge money for, someone else can give away, and vice versa. For instance, most of my competitors now offer a dark theme at no additional charge, but if I give mine away without any other changes, I’ll go out of business.
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The content industries figured out the solution a long time ago. If 97% of my users can’t or would rather not pay, but they spend substantial time in the app every day, the solution is probably ads.
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My bet is on audio ads in Overcast (added between and eventually inside podcasts) whenever he decides he really wants to monetize.