A feature article in the latest issue of Fortune documents Kentucky Sen. Rand Paul‘s efforts to win support among the West coast tech community.

Wooing the Patagonia-wearing, Blue Bottle coffee-sipping denizens of Silicon Valley, and especially San Francisco, may seem like a fool’s errand for much of the GOP, but not for Paul, who recently made his second swing through the Bay Area in as many years. Indeed, his libertarian leanings, which can rankle Republican Party pooh-bahs, resonate in the Valley, where folks are messianic about private enterprise’s potential to solve all the world’s challenges. (Exhibit A: Google CEO Larry Page saying he’d rather bequeath his wealth to entrepreneur Elon Musk than to philanthropy.) Among the technorati, Paul’s willingness to engage ideas outside the mainstream isn’t a liability — it’s his strongest virtue.

On his recent trip in late March, he talked like a native too: publicly delivering a harangue against the federal surveillance regime at Berkeley, which earned him two standing ovations in the liberal stronghold, and privately dropping by investor Tim Draper’s entrepreneurship school and gamely entertaining the billionaire’s quixotic pitch for splitting California into six states. (Paul says he’s dubious but hasn’t formed an opinion.)

It’s all part of Paul’s high-stakes gambit to expand the GOP’s appeal in precincts generally hostile to conservatives. “I see almost unlimited potential for us in Silicon Valley,” Paul tells Fortune in an April interview in his Capitol Hill office after his trip. “Many more of them are libertarian-leaning Republicans than they are Democrats, and they may not know it yet.”