I think you're missing a small yet significant portion of people who will pay for content after consuming it. Off the top of my head I've "tipped" after the fact for: An awesome free work time recording app, "free" walking tours when I'm traveling, free online chess, Wikipedia — all after using them.

I don’t think payment friction has been reduced nearly enough to make that statement. If it was possible to click a button to instantly send ten cents to the creator of an article, and people still didn’t do it, then we could conclude that it doesn’t work. But we’re extremely far from that now.

>We’re three decades in with the web and it’s pretty clear that voluntary payment nudges don’t work. Most people won’t pay for free content after they’ve consumed it.

Humans have no problem tipping, the issue is that a single article or piece of content is rarely worth than a fractional amount of whatever your preferred currency is, and it costs more than that amount to transfer that currency. Sponsorships work because you pay normal amounts of currency to receive a larger future block of content.

To make tipping work, you need a system that supports allowing you to deposit normal sums of money but then dole it out in micropayments, and also not charge more than those payments for processing the micropayments. A payment system like Paypal, that maintains an internal balance that is used instead of just transferring from one bank account to another (zelle, venmo), could handle this but I don't think the financial incentives are there for them to bother with it.