By the way, in terms of things not working out, a lot of that is not because the internet has failed but rather because the particular business model was never viable or because our economic system itself or some aspect of it has failed.
The whole issue of advertising is a case in point, which was intelligently explored by Exapno_Mapcase above.
The main issue with advertising is that it was always tacked onto and usually unrelated to the product itself. In the era of print, especially when there was a low supply of and high demand for information, this usually wasn’t a problem. You read the newspaper, the advertising was not too visually intrusive, and you may even have wanted the ads to know about the sale at the supermarket, etc. Sometimes it could be quite synergistic: if you were reading a fashion magazine, the ads for fashion were positively desired.
In the era of radio and TV, the breakdown was apparent, since the ads interfered with the enjoyment of the product itself and were rarely related. If you were a kid watching a TV show in the 1970s, as I was, the endless “don’t squeeze the Charmin” bullshit ads were anything but welcome. Nevertheless, the medium of TV at least had a valuable resource to sell, eyeballs on the screen, and it monetized very neatly. (As for radio, David Ogilvy himself in his book Ogilvy on Advertising: Ogilvy, David: 9780394729039: Amazon.com: Books said that its effectiveness in advertising was unknown.)
Finally, when we get to the internet, advertising instantly achieved true dogshit status. This article is from ten years ago but has stuck with me:
Online, advertising is, as with other media, arbitrarily connected to the product and intolerable to the user but now even fails to monetize most business models. It probably also fails to provide a return to most of the individuals and corporations that purchase it, though I’m no expert on that.
So, advertising sucks, but the impressively pathetic thing is that, thirty years on and with millions of brilliant minds at work on the problem, we have still failed to create very many workable new monetization strategies for online business models.
If you can charge for the product itself, that’s great. I pay $120.00 a year for Chess.com (website and app), and it’s totally worth it. I finally subscribed to dailykos.com. I of course buy tons of actual stuff online from Amazon and other online retailers. I pay for Amazon Prime. I pay Apple for cloud storage. But that’s about it. I am pretty resistant to paying for streaming services and subscriptions, and I just don’t do Patreon, Buy Me a Coffee, or any of that crap. And I guess people are mostly like me, since it seems pretty hard to make money online unless you’re Google or Facebook or are selling physical products. Meanwhile, a lot of these companies are losing billions of dollars a year, either as entire companies (Open AI, etc.) or specific divisions within them (the metaverse thingie in Meta). But hey, at least Uber is profitable now.