Paul has already raised tens of thousands of dollars from the libertarian tech set. Rand Paul's new (rich) friends

Rand Paul goes hunting in San Francisco starting Thursday for two things Democrats usually expect to have locked up in the Golden State: rich technology donors and computer geeks game to leave their jobs to work on a White House campaign.

Focusing on a libertarian sliver of the Bay Area’s tech crowd, the Kentucky Republican hopes the three-day trip can tap into a powerful resource that could boost his fundraising skills, message delivery and voter turnout — potent technology tools that were a crucial component in President Barack Obama’s two general election victories.


But Paul also has a more lofty agenda — using his strongly held views on National Security Agency surveillance, Internet privacy and free markets to broaden the traditional GOP coalition — and perhaps even persuade California voters to turn their state red for the first time since George H.W. Bush in 1988.

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“I think it has to be someone with the right message, but I think there’s room for us out there,” Paul said in an interview where he called on Republicans to “run a 50-state strategy.”

In Northern California, Paul senses one big opportunity for his likely presidential campaign. Sure, employees at Google and other major tech firms skew Democratic and overwhelmingly backed Obama in the past two cycles. But he says the administration’s recent history on surveillance and economic issues could help the GOP turn things around when it comes to both donations and support.

“I’m not just talking about going out there to seek fundraising,” he said. “Every time I’ve gone out there, the response I get is, ‘You know what, while we supported the president, we’re disappointed in the president on issues of privacy but also on issues of fiscal responsibility, taxes, regulations.’”

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Republicans are, of course, still a long shot, to put it mildly, to win California in 2016. The party’s cast of political operatives — POLITICO interviewed more than two dozen for this story — also caution that Paul still must demonstrate he could put any new technology converts (both staffers and their ideas) to good use on the campaign trail.

The senator also can expect to face stiff competition for the tech set from potential GOP primary rivals — Chris Christie, Jeb Bush and Marco Rubio sit atop the list — who bring their own deep policy and political chops to these issues.

But in large part because of the digital infrastructure inherited from the presidential campaigns of his father, former Texas Rep. Ron Paul, many top GOP political operatives, including some who are already lined up behind other potential primary rivals, concede the Bay Area’s bloc of potential technology-oriented donors and campaign workers appears largely Sen. Paul’s for the taking.

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“Rand Paul represents a lot of what Silicon Valley expects in a politician. Someone who is willing to engage new ideas and debate politics that might be a bit controversial or inconsistent with what the establishment would expect,” said Garrett Johnson, a former Jeb Bush aide and Internet start-up founder who helped organize a small, beer-fueled happy hour for Paul in March in downtown San Francisco.

“He’s going to be the one to beat from a digital standpoint,” added Martin Avila, head of the GOP technology firm Terra Eclipse, which has offices in Washington, D.C., and Santa Cruz, California.

Don’t get Paul and his Republican allies wrong — they’re not expecting Democrats to lose their grip on the Bay Area’s liberal coalition, especially when GOP presidential candidates are taking controversial stances on issues like climate change and abortion. But there are also plenty of ways where Paul has demonstrated his appeal to tech-minded young voters — namely, by slamming the NSA — and with a free-market stance that attracts recently minted tech industry millionaires and billionaires.

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“I think most people in Silicon Valley are actually more conservative on fiscal issues than the president, and they’re probably more moderate than most Republicans on social issues,” Paul said. “But without me even bringing it up, many of them bring up the word ‘libertarian.’ They say I’m not really Republican, I’m not really a Democrat, but I’m libertarian.”

Paul has already raised tens of thousands of dollars from the libertarian tech set during two previous trips to the Bay Area. During one of those visits in the spring of 2013, he toured Facebook (clad in a black turtleneck, he met briefly with Mark Zuckerberg and signed the company’s chalkboard “Give Me Liberty + Post It To Facebook”), Google and eBay.

The senator’s aides say his past visits were largely introductory sessions with potential funders who agree that the best technological ideas flourish when the government stays out of its business. On this week’s San Francisco trip, Paul’s schedule includes a keynote speech and panel discussion titled “Where has our freedom gone?” Saturday at the “Lincoln Labs” libertarian-themed technology conference, a breakfast with local physicians, several technology-themed round tables, fundraisers and one-on-one meetings with potential donors and supporters.

Paul has already found one wealthy friend in Peter Thiel, the PayPal co-founder and early investor in Facebook and LinkedIn, who gave more than $2.7 million to super PACs supporting Ron Paul’s 2012 presidential campaign. According to POLITICO Playbook, Paul had private meetings earlier this month with both Thiel and Zuckerberg at the Allen & Co. media and technology conference in Sun Valley, Idaho.

Also in Paul’s corner: Scott Banister, a PayPal board member and marijuana reform advocate who is scheduled to speak alongside Paul during the panel at the libertarian technology conference in San Francisco.

“That’s the $64,000 question,” said Craig Montuori, a Banister spokesman and Silicon Valley tech expert working on immigration reform issues. “If anyone can get them to open their wallets, Rand can.”

Montuori said there’s buzz in the Bay Area surrounding whether Paul will open up a tech-focused campaign office in the region — much like Obama did in 2012. Either way, he expects a large number of tech types offering their services to a Paul presidential campaign.

“They’re at a point in their career where they’ll semi-retire to go work for Rand, whether that’s in Iowa, Kentucky, New Hampshire or out here,” he said.

Banister and his wife, Cyan, who runs a soft porn website, have donated to Sen. Paul’s campaign and other outside groups supporting the senator. On a recent Twitter post, Scott Banister wrote: “News Flash: Rand Paul IS the wise man” and included a link to a recent Slate article on the foreign policy debate between Paul and former Vice President Dick Cheney.

Both Thiel and Banister declined interview requests, and sources close to them say it’s still unclear if they’ll dig much deeper into their wallets to fund Paul’s 2016 ambitions.

Paul acknowledged that he’s heard “some rumblings” that he should open up a tech-focused campaign office in Silicon Valley but stopped far short of endorsing the idea.

Democrats say they are paying close attention to Paul’s push into California, noting the fervent strain of libertarian-minded technology types who backed his father’s presidential campaigns. The same people also fueled Rand Paul’s own 2010 primary effort, when his campaign used so-called small-donation money bombs to beat the GOP establishment’s pick for the Kentucky Senate nomination.

“It makes every bit of sense that they’re looking for money in a place that’s just minted X number of billionaires. You’d be dumb not to,” said Stu Trevelyan, the CEO of the Democratic technology juggernaut NGP VAN. “The last go-around with the Republicans in their primary showed all you need is one really, really rich friend and you can last a long time.”

“I don’t know that I see his support as being as large in legion as Barack Obama. I do think it’s much, much more narrow, but there’s an intensity there that’s not to be dismissed,” added Laura Quinn, head of Catalist, another major Democratic technology firm.

Paul has carefully cultivated his technology image through social media and specific policy stances.

In December, he wrote to his 400,000-plus followers on Twitter with an homage to the faux “Seinfeld” Festivus holiday, sending out a series of messages (an “airing of grievances”) about soaring government debt, Federal Reserve policies and not remembering when to move his car for Washington, D.C., street cleanings. The senator’s Twitter audience, according to an analysis of his followers run by StatSocial, is nearly three-quarters male and favors media and entertainment from the Drudge Report, Ted Nugent and “Duck Dynasty.”

His official and political Facebook pages have more than 1.778 million and 594,000 likes, respectively, and feature photographs of him with Iowa’s famous landmarks and politicians, drinking a juice box at a McDonald’s in Manchester, New Hampshire, and seated on set with the Fox News team.

On the tech policy front, Paul has defended Apple’s brass against fellow Senate GOP lawmakers who complained about the company’s tax sheltering practices. His free-market stance could benefit Uber and Airbnb, tech-centered car sharing and travel lodging services, respectively, that face strong regulatory challenges at the state and local level.

In trashing the NSA and defending Edward Snowden, Paul has also carved out a position that contrasts with that of former Secretary of State Hillary Clinton, who recently called the former government contractor an “imperfect messenger” for launching a debate on government surveillance practices.

”She’s been part of an administration that hasn’t been friendly to privacy, and I don’t think I’ve ever heard a critical word from her on the NSA or any of this,” Paul said. “I think she’s been more complicit than adversarial on any of the privacy issues.”

Republicans bring mixed feelings over Paul’s outreach to the California technology community. For starters, he’s not alone in making a play for donors and their talent.

Chris Christie is close with Zuckerberg, who in 2010 donated $100 million to Newark’s schools and last year hosted the New Jersey governor at his first-ever political fundraiser. Bush’s support for a sweeping immigration overhaul is considered a winner among tech executives determined to hold on to prized talent. And Rubio is among the most prolific lawmakers on Twitter (his 625,000-plus followers ranks fourth in Congress behind only @SenJohnMcCain, @CoryBooker and @SpeakerBoehner), and he’s also championed Uber against local government regulators.

Several GOP operatives said they welcome the buzz Paul has generated in California. “We can only do better in the Bay area,” said Scott Tranter, a GOP consultant who has been working for Rubio’s Reclaim America PAC.

“You’re selling Coca-Cola versus RC Cola,” said Republican strategist Alex Skatell, referring to both Paul and Christie. “It makes everyone’s job easier. They’re going to do more interesting things. They’re going to take more risks. So it’s going to make everyone look smarter and more creative.”

Paul’s critics say his tech push is really more about good public relations and exciting potential donors than creating the long-term technology infrastructure that can help the party win the White House.

“I think a lot of it is atmospherics,” said one top Washington-based GOP technology operative.

Republicans are also cautioning Paul’s team against expecting too much from California tech types who offer political tools capable of matching the fast-paced rigors of a presidential campaign. They point to Mitt Romney, the former CEO and well-known data geek, whose campaign created a highly vaunted system for real-time tracking of voter turnout only to see it crash on Election Day 2012.

“I don’t know how many board meetings I spent doing political science 101, showing them how Washington works and then realizing they didn’t understand it after I explained it two or three times,” said Erik Nilsson, who founded Fundly, a Silicon Valley online fundraising firm, and who now works for a Virginia-based political technology company.

The senator’s supporters insist he’s on the right path and that his policy positions and past campaigns demonstrate he would make technology a working cornerstone of a presidential campaign.

“Anyone who is dragging their feet and wanting to ride in a stagecoach instead of a rocket is going to be left behind,” said Rex Elsass, an Ohio-based political operative and Paul supporter with close ties to the senator’s family (he once employed Paul’s wife, Kelley). “There’s not going to be any opportunity for those kinds of failures ever again.”