Hillary can probably win Silicon Valley—but it'll take some work: VC

Hillary Clinton is set to do well in Silicon Valley, a venture capitalist told CNBC's "Squawk Alley" on Monday. But even in historically liberal California, it won't be a slam dunk win for the Democratic front-runner.

"Over the last five or six presidential elections, the candidate with the most charisma ended up winning," said Paul Holland, general partner at Foundation Capital. "I don't think you can discount Donald Trump from that perspective. I think that's a place where Hillary Clinton needs some work."

Holland last week held a meeting of about 40 technology industry insiders for a spirited discussion on the current field of presidential candidates. A significant share of the attendees he described as "right of center." Trump may pick up more votes in the valley than people realize, simply because he's a "phenomenon," Holland said.

"I think Trump is an enigma," Holland said, noting that as a blue state, California doesn't see the heavy political advertisements that saturate televisions in contested states.

Some technology insiders do have skin in the game through the Republican Party, with Robert Mercer of Renaissance Tech backing Ted Cruz, and Oracle's Larry Ellison donating to Marco Rubio. But while Trump was a popular focus of the conversation, out of 100 invitees to the event, Holland said he couldn't find a single person to speak on the record for either Trump or Cruz.

"Once he's out here and starts paying attention, I'm sure he'll have his fans, or have some people that are interested," Holland said. "But I just have to say, the valley is an incredibly diverse place. ... It's a tough sell to come here and really sort of preach to people this notion of closing the borders and intolerance."

Indeed, the Clintons have a long-tradition of ties to the technology industry, Holland said.

"Hillary Clinton has done a very good job of forming relationships out here," Holland said. "The Clintons are well-respected. I think they did well by the tech economy."

— CNBC's Eamon Javers contributed to this report.