I really like how he automates his newsletter off of his blog, notes, TIL, etc., but it's also amazing how complicated it is. Imagine the blog would be on Markdown, nothing of this is needed as the "content" would just be locally for a Claude to read, it could do the SQL-query with a cmd-line instead, or you could build a small wrapper around if you want. Plus if the Newsletter supports Markdown, too (I use Listmonk), then the conversion would be straight forward too, also with no bugs.
This inspires me to automate one day more of my newsletter too, maybe as I have everything in place for it. And I automate blog post to send out automatically, but not a collection of notes and blogs.
There's also an accompanied blog post: https://simonwillison.net/2025/Nov/19/how-i-automate-my-subs...
I really like how he automates his newsletter off of his blog, notes, TIL, etc., but it's also amazing how complicated it is. Imagine the blog would be on Markdown, nothing of this is needed as the "content" would just be locally for a Claude to read, it could do the SQL-query with a cmd-line instead, or you could build a small wrapper around if you want. Plus if the Newsletter supports Markdown, too (I use Listmonk), then the conversion would be straight forward too, also with no bugs.
This inspires me to automate one day more of my newsletter too, maybe as I have everything in place for it. And I automate blog post to send out automatically, but not a collection of notes and blogs.