One of the hardest aspects of writing on the internet is developing a core audience of people who will make a daily task out of reading your website. Website feeds have long been a good way to alert subscribers of something new, but they need to be explained, so they aren’t great for reaching a wide audience of varying technical ability. For a brief moment, it seemed like automatic delivery of links through pages on Twitter and Facebook would be a good in-between answer, but their constant fiddling with feed contents based on unknown user metrics severely hampers reliable delivery to subscribers.
Email is a great lowest common denominator solution. It is an open standard that everyone already knows how to use. An email client is a feed reader without a learning curve.
I think paid newsletters are cool. It’s such a clear way to monetize an audience that finds value in what you have to say. I would think the tech is less fiddly than website paywalls as well. You pay, you’re on the list, you don’t pay, you’re not on the list. Websites need login systems which are non-trivial.
I haven’t gone down that road myself as so far I’ve monetized my writing career with advertising on the site that’s not behind a paywall, which is, of course, good for SEO. That’s mostly blogging, but I do also write an email newsletter (it’s a team-effort) directly on the site (and it gets sent out after being published on the site). I highly recommend that as having a URL for things you write is just a good idea. Then if you want to paywall in the future as well, that’s an option. I’ve also done that with some writing.
Whether it’s paywalling on-site content, or a paid email newsletter, I think it’s probably smart to 80/20 it. 80% free, 20% paid. Your true fans will pay you, and the 80% helps find new true fans. Maybe once you’re outright famous you can tilt the scale one way or another depending on how well things are going.