Newsom has gotten financial backing for many of his ventures from billionaire Gordon Getty (right), a longtime family friend who has taken keen interest in PlumpJack Winery.

Editor's Note: When Wine Spectator first reported on San Francisco mayor Gavin Newsom, after he won a hotly contested race for the seat last year, he was still little known around the country. Since then he's made a national name for himself with his controversial decision to issue marriage licenses for gay couples, sparking a boom in same-sex weddings in the city.

Gavin Newsom seems to have it all -- a successful business centered around wine, restaurants and resorts; good looks, charm and sophistication; a wife who is a former model turned city prosecutor; a politically connected father; and a billionaire family-friend and financial backer. Now, at age 36, he is also the new mayor of San Francisco and a rising star in the Democratic Party.

Newsom -- cofounder and (since his mayoral run) former managing partner of PlumpJack winery in Napa Valley, the PlumpJack restaurant group, and the PlumpJack wine shops in San Francisco -- says he always tries to set "big, hairy, audacious goals" for his businesses and for himself. "I don't want to have a modest goal and reach it," says the entrepreneur, whose innovative businesses include a fine-dining restaurant that sells wine at retail prices and a winery that puts screw caps on a $100-plus Cabernet.

He's certainly got a lot of audacious goals to meet now. Newsom is expected to create jobs and jumpstart the economy in a cash-strapped city still coping with the collapse of the dot-com bubble. And he must deal with a Board of Supervisors that has opposed some of his key initiatives.

Newsom's detractors depict him as a privileged pretty-boy. But sitting and talking with him, it's hard not to get caught up in his energy, confidence and what could be polished political rhetoric but comes across as boyish enthusiasm and idealism. ("I live in exclamation points," he says.)

Not much has stopped Newsom since he and Billy Getty -- son of billionaire philanthropist Gordon Getty, an heir to the Getty Oil fortune -- opened their first wine shop in San Francisco in 1992, when Newsom was 24. At the time, big chain retailers such as Costco were spreading, and heavy discounting was putting traditional wine merchants out of business. The two friends wanted to create a shop to appeal to younger drinkers, with high-quality, affordable wines and a fun-loving, irreverent attitude.

Though Newsom had gained an early appreciation for wine from family and friends, when he and Getty walked into wine shops, they would be shown to the beer section because they were young.

"We realized there was a real gap -- it was either a very pretentious atmosphere, or the atmosphere was so discount-oriented that it took away a lot of the romance and the story." They tried to fill a role in between, providing value and demystifying wine while keeping the romance. "It was a niche no one thought could work."

They took the name PlumpJack -- the witty rogue Falstaff from Shakespeare's Henry IV and Merry Wives of Windsor -- to represent their attempt to turn tradition on its head. (Gordon Getty had composed an opera called PlumpJack.) Newsom says, "We take our work seriously, but we don't take ourselves so seriously."

Newsom -- with the help of the Gettys, other investors and his management team -- has since built a mini-empire out of the PlumpJack brand, businesses united by philosophy and whimsical, theatrical design. Among the holdings in San Francisco are the PlumpJack Wines store, PlumpJack Cafe, Balboa Cafe and the MatrixFillmore nightclub -- all dominating a short stretch of Fillmore Street in the city's upscale Marina/Cow Hollow neighborhood.

The company encompasses another San Francisco wine shop and a resort -- PlumpJack Squaw Valley Inn on Lake Tahoe, which is also the location for two PlumpJack Sport clothing outlets and outposts of Balboa and PlumpJack cafés. And there's PlumpJack Winery in Oakville, whose Cabernet Sauvignons have consistently earned outstanding ratings from Wine Spectator since the debut 1995 vintage. "Each business we have reinforces the other businesses," says Newsom.

PlumpJack Cafe, just up the street from the shop, opened in 1994 selling prestigious wines at retail prices. "Immediately, the experts said, 'You'll go out of business,' just like they said with the wine stores. 'It cannot work, son, you know nothing about the restaurant business.' I acknowledged I didn't, but I knew what I liked when I went out," says Newsom, adding that PlumpJack makes money by selling higher volume and creating repeat customers.

"I have a hard time going to other restaurants, I'm offended [by wine pricing]," he says. "I just don't accept the arguments. Come on, I have Riedel now; I have a sommelier; I'm still selling wine at retail."

Newsom says he seeks out people who are willing to take risks and to ask, "What if?" Once again turning tradition on its head, he and the Gettys took a leap in 2000 when PlumpJack Winery became the first luxury brand to carry a screw cap to prevent the problem of cork taint. Starting with the 1997 vintage, they released half of their Reserve Cabernet with a screw cap -- and they charged more for it, $135 per bottle versus $125 for the cork closure.

The winery owns 53 acres in Oakville, with Screaming Eagle across the road, Rudd next door and Dalla Valle on the hill nearby. Since opening in 1995, PlumpJack has focused mainly on estate Cabernet, along with some Chardonnay and Merlot. Newsom says, "It's sort of analogous to politics: You have to reinforce the core, you've got stay on message. You don't want to be pretty good at a lot of things, you want to be great at a few things."

Newsom, whose father is a retired state appeals court judge, got his political start in 1996 when San Francisco Mayor Willie Brown appointed him to the Parking and Traffic Commission, then to a vacant seat on the Board of Supervisors.

A moderate Democrat, Newsom made his name with a pro-business attitude and a tough-minded approach to dealing with the city's homeless problem. Though Newsom was the frontrunner all along, the mayoral race came down to a surprisingly close run-off with Green Party candidate Matt Gonzalez. While Newsom is mayor, his holdings are in a blind trust, to avoid conflicts of interest.

Since first entering city government, Newsom hasn't had much time to enjoy the Napa wine country lifestyle. "I've only experienced the work side of it," he says. He's embarrassed to admit that he has just recently started assembling a wine collection, focusing on Burgundies and 2000 Bordeaux, among others.

"You'd think that I would have a great cellar. When we bought wine, I was in the business of selling it, not hoarding it. I always sold all our allocations. In hindsight, I regret it because I could have had an extraordinary cellar if I just set aside a little bit. But I think I have an extraordinary business because [of what] I did."

Should his political career ever come to an end, he has that business to fall back on. "I'd love to go back and do wine tastings in Napa every weekend. Those were the days," Newsom says. "I enjoyed being a wine merchant. I like the romance of it, talking about it. I liked opening and closing the restaurant, being a host. I'd be happy to go back and do that."