I did the CAD work and he the machining... He taught me how to use mill, and I taught him how to use the computer. This was at a time when I was designing housings for Ku Band earth terminals.
It was a rather fun experience, and really opened my eyes on what can be done with a hunk of 6063-T6, some imagination, and the right CNC machine.
I used AutoCAD for the design work and eventually had his computer set up and automated to the point where I could phone his machine and send a DXF file with depth info and he could assign some tools, and the prototypes would be done just a couple of hours.
It was great to have that sort of rapid prototype capability.