What if the key to freemium models lay in machine learning?
Enrique Dans
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It looks a lot like the “membership” Medium is currently trialing with its core users: paying for a smart selection of readings. To be honest this works fairly well but is still far to achieve the level of customization you envision.

I could see a caveat in this model however. At least in some cases like media. I doubt Le Monde newspaper (I’m a paying subscriber) or Medium could offer me the best selection of readings because:

1/ Not all pieces of writing of interest are on their platforms

2/ they don’t have as much data on my habits as would have a third-party AI-based service that would take into account all my readings of every media (though they could themselves develop such a service)

What would be the added-value of Le Monde or any media against a pure-player dedicated to harvest data from millions of users across any media platform? That might be an issue unfortunately.