pretix and Venueless are two pieces of software you've just interacted with if you're listening to this talk: pretix powered the sale of your ticket, and Venueless is powering the virtual conference platform in use. There are multiple different models to build a business around an open-source application such as SaaS, open core, support services, sponsored feature development, dual licensing, almost-FOSS-licenses. By now, we've tried every single one of these approaches and haven't been entirely unsuccessful: Currently, almost 15 people make a living building and supporting these two projects and their ecosystems. In this talk, I'll tell you the story of how we got here, hoping that at least some of the things we learned are transferable to other projects as well.