Gavin Newsom Wants to Be Governor of California. Would You Hire Him?

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Polarizing Figure: During Newsom's first campaign for mayor, he has burned in effigy by gay activist who accused him of turning against the city's poor. Photograph by Creative Commons

After our conversation at Max's, Newsom is off to a fund-raising dinner in Silicon Valley, hosted by "Anne and Lucy," better known as Mrs. Sergey Brin and Mrs. Larry Page, respectively. He takes special care to note that, although plenty of boldface Valley names will be there, it's not an official Google event. "Wouldn't want to hear that on The O'Reilly Factor," he says.

Newsom needs to prove that he can garner the support of business titans both to fill his coffers and to help him make his case. One local CEO echoed a common refrain: "What's he done? He's never here, and when he is, he's grandstanding." And the venture capitalists I've spoken to aren't sure they've seen their candidate yet. "This is a leadership issue," says Mitchell Kertzman, managing director at Hummer Winblad Venture Partners. With the onerous budget-making process and the remnants of Prop 13 (which limits property taxes) creating funding logjams, "someone has to be courageous and modify these things." If California were a business? "I'd wipe the slate clean," says Kertzman, "bring the valuation down at near zero, and agree to start again. But this isn't Chrysler or a startup we're talking about."

Fixing government by making it run like a business is the strategy Newsom originally campaigned on, and it's the one Whitman seems to be sticking with. Long married and congenitally buttoned up, Whitman is emphasizing her "strong values" and business record while she formulates an expanding portfolio of views and solutions. "Growing the economy, creating jobs will be a big priority," she told me recently, reverting effortlessly to her talking points.

Newsom, who has business credentials of his own, concedes that in a campaign, "you can usually get away with the 'I'm going to run government like a business' thing. It's an applause line." And then, he says, you get into office. "It's a civil-service system. It's not just a right/left advocacy thing. It's nuanced. And it takes time not just to fire people, but to hire them." You can either legislate change or go to the voters. By then, new economic realities hit. "And you have to react to that," he says. "You have less influence outside your realm than you think."

"You can get away with the 'I'm going to run government like a business' thing," Newsom says -- until you get in office.

A fourth-generation San Franciscan, Newsom grew up in a home of modest means run by a determined, divorced mother who worked two-and-a-half jobs to make ends meet, took in boarders, and fostered children. "She was a waitress," he says. "So I worked as a busboy." Hindered by severe dyslexia, he struggled in school. But his mother enforced a work ethic that kept him disciplined and focused. "I worked construction and had paper routes," he says. His sister, Hilary, once told the San Francisco Chronicle that her brother has been presenting himself as a power broker with slicked-back hair and tailored suits since he was a teenager. "I don't know about that," he says, rolling his eyes. "I'll say I was a focused kid."

His father, a judge famously associated with the Getty family, "was a great dad, but he wasn't there much," Newsom recalls. But through his father, he developed a relationship with Anne and Gordon Getty, who ended up investing in the wine store he opened in 1992. (They also paid for a hefty chunk of Newsom's first wedding.) Still, Newsom says, "When there was a heat wave and all my wine bottles popped, I was so undercapitalized that I had to tap the equity on my $179,000 condo. I know how hard it is for businesses that can't tap the credit markets now." The wine shop was the first piece of PlumpJack Associates, which he built into a successful business with 14 operations, including a café, two wineries, and two resorts; its 2007 revenue was reported to be in the vicinity of $50 million. (He retains an interest in the businesses that operate outside of San Francisco proper.)

But there's that baggage. He divorced his first wife, Fox newscaster Kimberly Guilfoyle, in 2005. The next year, his affair hit the news. He calls it a terrible personal mistake. While he reassures me that there is a part of the story that has yet to come out, he says, "I can reconcile everything but not the pain that I caused. I hurt two people, and that is my great regret."

He is now remarried to Jennifer Siebel Newsom, an actress and aspiring documentary filmmaker who, when I meet her in May, is imperceptibly pregnant with their first child. Cynical murmurs have suggested that this is a made-for-TV marriage, complete with camera-ready spawn. But watching Siebel Newsom wow the crowd at the recent Professional Business Women of California's annual conference suggests that she has some heft of her own. She's friendly, talking policy and women's issues without any handlers. She shows an eight-minute teaser of Miss Representation, her documentary on images of women in popular culture. "We're in our own fund-raising crisis right now," she says of her unfinished film. "I'm ready with my elevator pitch anytime."