We spent $85,000 for buttondown.com in April; this was the biggest capital expenditure I've ever made, and though it was coming from cash flow generated by Buttondown rather than my own checking account it was by rough estimation the largest non-house purchase I've ever made.

As of August, we're officially migrated over from buttondown.email to buttondown.com. I'm sure I'll do a more corporate blog post on the transition in the future, but for now I want to jot down some process notes:

• The entire process was made much more painful due to Buttondown's architecture, which is a hybrid of Vercel/Next (for the marketing site and docs site) and Django/Heroku (for the core app) managed by a HAProxy load balancer to route requests. We ended up using hurl as a test harness around HAProxy, something we probably should have done three years ago.
• I went in expecting SEO traffic to be hit as Google renegotiates legions of canonical URLs; it hasn't, at least thus far. Instead, everything seems to have just bumped fairly healthily.
• I expected more production issues to come up than actually did. I credit this to a fairly clear scope: the goal was "to migrate all web traffic to .com", which meant that a) we didn't need to re-map any paths and b) we didn't need to worry about mapping SMTP traffic (which still runs through buttondown.com).
• The hardest part of the process was the stuff you can't grep for. URLs on other sites, OAuth redirect URLs, that sort of thing.
• Starting with isolated domains (the documentation site, the demo site) that weren't tied to the aforementioned HAProxy load balancer gave me some good early confidence that the migration would be smooth.

Overall: very happy with how it turned out. I would describe the project roughly as "three months of fretting/planning, one week of grepping, and one week of fallout."

Was it worth it? Yes, I think so. Most theoretical capital expenditures Buttondown can make right now have a non-trivial ongoing cost associated with them (buy another newsletter company or content vertical and now you have to run it on a day-to-day basis; do a big marketing build-out and you have to manage it; etc.) — this was a sharp but fixed cost, and it's something that I knew I wanted to do in the fullness of time. (And, most importantly, people stop referring to Buttondown as "Buttondown Email", a personal pet peeve of mine.)