I don't mean the projects. I mean the ideas he is trying to convince people of. Take for example his stance on DRM. What does success look like, or rather, what does it not look like? You might be able to argue moderate success in music (iTunes switching to DRM-free, but Spotify having DRM), yet in books the wide acceptance and love of Amazon's Kindle indicates a lost battle.
But you might also say the same about convenience. It doesn't make sense to completely ignore either of convenience or freedom in pursuit of the other. Most people are pragmatic about it. They compromise some freedom for convenience, and compromise some convenience for greater freedom.