Moved newsletter from Mailchimp to Buttondown.

In preparation for the release of An Elegant Puzzle, I set up the page to subscribe to my newsletter on January 20th, 2019, heavily inspired by Julia Evans’s approach. I didn’t know anything about releasing a book, but Brie Wolfson coached me through it, and having a newsletter to tell folks about the book seemed like a good idea. My blog had already had an RSS feed for ~12 years at that point, but RSS usage has steadily declined since the golden era of the 2000s.

Following Julia’s post, I set up my newsletter to run on Mailchimp, and that has mostly worked well for me over the following six years. (Looking at Julia’s website, it looks like she subsequently moved to Convertkit at some point.) However, over time I kept running into issues with Mailchimp. Those frustrations slowly mounted:

1. I could not find the “welcome to this newsletter” template to change the recommended posts. I think this might have been related to them rewriting their UX entirely at some point, but I didn’t really want to become a Mailchimp expert just to update this
2. Every time I changed jobs, someone would tell me that I needed to update the address for contact, and each time it felt a little bit harder to find the text field to update it
3. The DMARC changes were confusing to navigate within Mailchimp. DMARC enforcement was absolutely not Mailchimp’s fault, but configuring it with Mailchimp was a fairly confusing process. Presumably the documentation is much improved at this point, but wasn’t great for me at the point I cut over
4. I was paying $326/month for something that was difficult to tune to work how I wanted. The cost has increased over time, so I wasn’t paying this much the entire time, but back-of-envelope I paid Mailchimp somewhere around $15,000 over six years

Every year or so I’d considered migrating off Mailchimp to something that was more purpose-built for my needs, but never quite got around to it. However, this year I decided to go ahead and migrate. I did some quick research, landed on Buttondown (whose founder I happened to overlap with at Stripe), and the next newsletter on Wednesday will be coming from Buttondown rather than Mailchimp. I’m not quite sure how much I’ll end up paying Buttondown, but it’ll be either $79 or $139/month.

The cutover was very straightforward, including getting to write a bit of Django template syntax for the first time in a decade or so and some DNS setup. Now the imported archive is up at archive.lethain.com, and I’ll start sending this upcoming Wednesday. One small feature that I’ve wanted for a long time on Mailchimp is the ability to change the format when the newsletter has one or more than one post in it, which was a quick win on Buttondown.

This doesn’t mean I have plans to meaningfully change how I’ve been newslettering for the past six years, although I hope it’ll get a bit more interesting in 2026 versus the prior two years, as I’ve completed my book publishing goals for the 2020s, and am excited to return to writing more widely about stuff I’m working on! There’s only so many years of sharing draft chapters before it starts to feel a bit stale.

As a final thought, two years ago I think folks would have been confused by my decision to not move to Substack, just like six years ago they would have been confused by my decision not to move to Medium. The answer here is easy for me: my goals remain consistent ownership of my work, on domains I control. If I was writing to directly build a business, I imagine both of those choices would have been much harder, but at this point I’m surprisingly anchored to my desire to be an operator who writes, which is where I think the most interesting writing happens.