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The two examples we have aren't great: video streaming and newspapers.
For video streaming, they try to create as much of a monopoly as possible and then extract value from you--enshittification. And even at this early stage, it's not the "ad-free" tier it's "ad-free^*^" tier.
For newspapers, rich people just buy them and blatantly use it for propaganda; they're willing to operate at an official loss if it saves them from regulation or taxes.
Honestly, the ad-free* tiers is what is making me want to do away with ads the most. I don't mind paying for a service, I do mind paying for a service just to get ads anyway. The double dipping is so annoying.
It's becoming increasingly difficult to find a service provider that isn't actively forcing ads into premium tiers.