> for a bootstrapped British company in 2004 it wasn't even a question, there was nothing to buy. So that's context I didn't have and it makes a lot of sense f

> for a bootstrapped British company in 2004 it wasn't even a question, there was nothing to buy. So that's context I didn't have and it makes a lot of sense for 2004. I wouldn't apply this to 2024 any more than I'd apply my old boss's lessons about dBase to modern database design. > I truly did spend a lot of time This is the core of the issue. If I were starting a business in 2024, I'd say "stick Stripe Billing on it" and "spend a lot of time" on things my customers care about instead. The reality of building your own billing system is that you have to learn about all the things we both mentioned above and, as your business grows, start praying that the team you have working on it also learn those things. Otherwise you end up with the problems I mentioned (and I know this because I inherited these problems from my predecessors).