A few years ago, Derek Sivers announced a plan to rewrite CD Baby’s web interface in Ruby on Rails, and he had a blog for his progress. That blog went dark a while ago, and recently he announced his plan to abandon that project. His insights are interesting, and I in general would agree with him. As much as I enjoy Ruby on Rails, and for as much as I could not have built and maintained AmigoFish without it, I wouldn’t recommend people rewrite existing systems in RoR without a very good reason, and maybe not ever. It’s fantastic for greenfield development when you can pick everything, but less so when you have to mold it into the shape to fit your legacy systems. When you have a functioning business generating real cash already in that legacy system, you should be very careful farting around with the fundamentals.