I'm not really sure what to think of Stratechery. It's got lots of words that are difficult for me to quickly skim the overall gist of to gauge whether they might be interesting, including paradigm 33 times, disrupt 58 times, and of course AI 247 times on the front page. From my angle it reads like a Dilbert comic so I guess I can't answer why the intended audience would or wouldn't pay $0.10.
Another observation though is that he literally describes his own site as having a "content business model" and his own posts as "content", so I think the word choice is more telling than you realize. I see it and just think "ok..." and hit back. I guess it pays his bills though so it seems to work. Apparently someone's giving him the $0.10. Other people in the content industry looking for tips like some giant ouroboros?
I don't know how I can be more clear about this. It was a thought experiment. Take the very best piece of writing from [BOOK/ARTICLE/TEXTBOOK/JOURNAL] you could ever imagine. Would you or should you be willing to pay 10c for it? I'm not asking about Stratechery in particular (although there are many, many people that happily pay Ben Thompson $15/month that I'm sure most people would describe as intelligent).
You might quibble that you would only pay for a physical book or whatever. I say why? Are you paying for the content (that word again) of that book or the paper? I'd argue the former. So why does it really matter if it was online or not? In the future it seems reasonably likely that there will be a higher proportion of the best writing online vs in books. Sure, a lot may be willing to write for free, but do you think it absolutely impossible that some percentage of them charge?
Realistically, like I said, I already doubt I will get through all of the physical books I have, so apparently I bought them as decor. I suppose deep down I knew that at the time which is why I got them for $0.50/ea at a thrift store.
So I suppose no, I can't think of any content I've thought to pay for recently, and have trouble picturing what I would pay for going forward. I already don't even take the time to read all of the writings of nobel laureates, fields medalists, etc. when they're already giving it to me for free. Not just old works but current blogs. There's more than a lifetime of the best works out there from world renowned experts. Thousands of years of the very best writing and I can't be bothered. And that's just writing. The list of things to occupy my time is endless. Acquiring something to read/watch is just not a problem I have. It doesn't make sense to pay for more. I have too much of it.
The content industry is competing with the entirety of recorded human history even before gen ai. A nearly impossible task unless someone destroys it all out of spite.
Another observation though is that he literally describes his own site as having a "content business model" and his own posts as "content", so I think the word choice is more telling than you realize. I see it and just think "ok..." and hit back. I guess it pays his bills though so it seems to work. Apparently someone's giving him the $0.10. Other people in the content industry looking for tips like some giant ouroboros?