It may be that it wasn't feasible on large scale to match content to ads. I feel like recent advanced in machine learning and ai could change the game there. W

It may be that it wasn't feasible on large scale to match content to ads. I feel like recent advanced in machine learning and ai could change the game there. What were describing is essentially how television ads worked for decades, isn't it? You know the content, so you can identify the demographics and advertise properly. Podcast and YouTube sponsor deals often work that way too (not always, but that's on the advertiser).