If your friend uses strong DRM and/or uses cloud based "purchasing" to keep users from possessing the bought files, I hope he fails.

The last thing I want is more DRM peddlers catering to people who aren't in the know about every tech nuance out there. So yes, it can he unduly harsh. But in our legal environment (with little recourse), drm providers almost always deserve it.

An exception to that is companies that sell "drm" servers to authenticate that only X licenses of software are used at one time. License compliance is another drain on innovation, but can be effective in keeping legit in compliance.