Senator Rand Paul, the Kentucky libertarian, faces a tricky challenge as he crisscrosses the country courting Republican moneymen for a potential presidential bid. Rocketed to national fame on the strength of his contrarian ideas, he’s now got to convince a skittish donor class that the same approach shouldn’t disqualify him if he seeks to carry the GOP’s banner in 2016. In many places, it’s meant twisting himself into pretzels to accommodate more traditional views, especially on foreign policy. Lucky for Paul, there is one corner of the map with both heaps of money and an appetite for investing in unproven startups founded on funky ideas: In Silicon Valley, the Senator is building something of a second home base.

We went behind the scenes of Paul’s whirlwind visit to the tech capital earlier this spring, then sat down with Paul back in his Senate office to talk about his wooing of the industry, for a story published online today and in the May 3 issue of the magazine.

It’s a high-stakes gambit for Paul, and he ups the ante by predicting a wholesale transformation of the liberal stronghold into a bastion of conservative support — provided, of course, the GOP chooses the right nominee. “I see almost unlimited potential for us in Silicon Valley,” Paul tells Fortune, positing the area is rife with libertarian Republicans “who may not know it yet.”

Read the full transcript of Fortune’s Rand Paul interview

Paul allies say the Valley will feature prominently as a reference point for his broader economic vision, in which unbounded private enterprise creates vast wealth while tackling social needs. But first thing’s first: The area holds tremendous potential for its ten-figure personal fortunes that can single-handedly sustain a presidential bid in the new, anything-goes era of campaign finance. The wide-open Republican primary field underlines the urgency for contenders to assemble topflight national networks. Out in northern California, Paul has a jumpstart with the region’s band of techno-libertarians, like investor Peter Thiel, who spent more than $2.7 million supporting Paul’s father’s 2012 presidential bid without ever having met the candidate.

Paul is already tracing a more methodical path to winning tech support. The story details how Paul announced himself to the industry with a bang, by apologizing to Apple CEO Tim Cook last May during a Senate hearing intended to shame the corporate giant for its tax avoidance strategies. A week later, Paul made his maiden visit as an officeholder to the tech hub and met with a hero’s welcome. In the time sense, he’s forged connections to big-name investors: Marc Andreessen, Sean Parker, and Thiel himself. Though Thiel remains publicly uncommitted in the 2016 sweepstakes, he also once described his 2012 contributions to super PACs supporting Ron Paul as laying the groundwork for 2016, and it’s difficult to imagine somebody other than Senator Paul claiming that inheritance.

But just how natural is the affinity between Paul and Silicon Valley’s libertarian cohort? Paul’s privacy crusade, sharpened by the Snowden revelations, gave him common cause with tech CEOs outraged over government snooping into their consumers’ data. It was also the official basis of his latest West Coast jaunt – a speech at Berkeley railing against the federal surveillance regime’s abuses that earned him two standing ovations in the lefty epicenter. At the same time, Paul stakes out a potentially provocative position when it comes to the industry’s own responsibilities, telling Fortune that consumers need the power to sue tech companies who violate the terms of their user agreements. And other potential friction points lurk. Paul on his most recent trip attended a fundraiser cohosted by Joe Lonsdale, a Thiel acolyte and the founder of Palantir, whose data-sifting software won it startup funding from the CIA and work for the NSA. Paul himself dismisses any suggestion of an inconsistency, insisting he’s not “afraid of the loom” nor against spying, as long as it’s done within a strict legal framework.

Read to the end, where Paul offers his pitch for a tweaked Bitcoin.