I wrote more about the pricing strategy here (https://buttondown.email/blog/pricing-page-driven-developmen...) but — when Buttondown first launched I _had_ a souped-up free tier (up to 1K subscribers!) and it certainly helped with early adoption, but hurt almost every other part of the business — in particular unit economics and customer service. Curtailing the free tier felt like ripping off a bandaid, but it also solved two of my biggest problems at once:
1. Conversion rates nearly doubled. People who found Buttondown valuable suddenly had an avenue and reason to pay for it!
2. _Margins_ went up. It costs money to send emails; a user who sends, say, one newsletter a week to five hundred subscribers costs around two or three bucks a year just in email alone. Supporting _thousands_ of these users (who are very nice people!) hurt my bottom line.
3. Customer service got way easier. This might not apply to all cases, but the _majority_ of my time answering emails and helping folks was spent on people who weren't spending a dime. While I genuinely want to help all people regardless of how much they are (or are not) paying, it was not sustainable for me to run a bootstrapped business where I spent 4+ hours every day helping people who did not find my service valuable enough to pay $9/month.
Having that free tier I think was a useful wedge to get initial customers and users onto the platform (and I am grateful for those initial users, who I've kept on their free tier!) but I think something significant would need to change for me to consider going back to that set-up.