John Perry Barlow’s journey to Internet guru-hood may seem unlikely, but look closely and there’s a thematic consistency—a passion—that makes his one of the great reinvention stories. Ten years ago, this sometime Grateful Dead lyricist and full-time Wyoming rancher left the cattle business, got off his horse and into his car, and headed West to the next great frontier: Silicon Valley. He recognized the burgeoning Internet as an expression of the values he held dear as a cattle rancher and Wyoming Republican County Chairman: community, freedom of expression, frontiersmanship, and a hearty dose of libertarianism.

His cowboy skills didn’t exactly translate into the digital world, but he soon began to make a name for himself by hanging out at upstart companies, observing, thinking, and posting ideas to online communities like the Well. After a run-in with the FBI, he co-founded, with Mitch Kapor, the Electronic Frontier Foundation, the first and arguably the most influential cyber-rights organization. These days Barlow’s cowboy boots are a mainstay, but he wears many professional hats: Internet consultant, visionary, writer, and activist/advocate. When I met him, he was scrambling around the halls of MIT’s Media Lab, helping under-16 Junior Summit ’98 attendees prepare to address the United Nations by satellite video.