I had a friend back in the early 2000's who did this.
He paid for this way through school by abusing the schools T1 access and pirated shitloads of movies and would dump them all to DVD-Rs and then sell them on ebay. He wouldn't make exact DVD rips, he instead would fill the DVD with tons of different movies or shows and sell them as collections. He did especially well with anime, which was difficult to access in the US at the time.
He later went on to be an electrical engineer at Boeing.
I also remember people hating Valve at first for this DRM scheme, and it's also weird that people forgot that Steam itself is a minimally invasive form of DRM.