Every commercial open source company has this conversation eventually, and how it is handled decides whether you get revenue or a fork. Key learnings: - Where to draw the commercial line so it reads as fair rather than extractive - Signals that an open source user is ready for a commercial conversation, and signals they never will be - How to talk about money with a community that did not sign up to be a lead The session works through how different companies have drawn that line, what the reaction taught them, and what they would do differently now. Practical rather than philosophical, and drawn from the times it went badly as well as the times it went well.