There’s so much content out there, why would I ever pay for a newsletter?
The short answer is “because some newsletter writers are just that great.” It all depends on what you’re interested in, how much you value the insight of a writer, and how much you want of that insight. Do you NEED to pay for content? No.
But you might want to sometimes.
Take for instance a friend of mine; we will call him Ed. Ed reads a LOT and he subscribes to a lot (NYT, Wall Street Journal, Matt Levine's Money Stuff, Benedict Evans' Newsletter, etc) . But there was one newsletter in particular that he found himself most looking forward to reading: Stratechery, by Ben Thompson.
“I was excited to get up every Monday and read it; it’s the best thing I read every week! I craved more.”
After actually thinking about it, he realized he COULD actually get more-- by subscribing. And why wouldn’t he pay to read more of the BEST reading he could? People are used to paying for newspaper content, for magazine content, for tv content, for lots of content. So it may seem like a “duh!” moment, but yes, he decided to pay for the newsletter content. Ed has zero regrets, content he’s really appreciative of, and deeper, better knowledge in the tech-business space.
Great newsletters do take time, effort, and often a lot of research on the part of the writer. Some do it full time-- and it is their primary source of income. Some do it part time or on the side. So while it might seem strange at the outset to pay for newsletter content, think about the value you’re deriving from it and you can decide whether you’d value more of it -- or not.