Over the last decade, Google Inc. has earned a reputation for rabble-rousing by pushing the limits of the traditional marketplace. But a recent confrontation underscored Google’s own rapidly changing circumstances: The tech giant and its rebel lawyers were on the receiving end when a 21-year-old student stood up to Google’s YouTube division.

At the heart of the commotion is Philip Matesanz, a computer science major who lives with his parents in Germany. In 2009 he launched YouTube-MP3.org, a website that enables users to rip audio—primarily music—from YouTube videos and convert it to mp3. The service is free for users; Matesanz earns revenue from ad sales. He won’t disclose his earnings, but he’s apparently doing well. He says he spends a “six-digit euro figure” on annual site maintenance.