Food coverage is supported by a generous donation from Susan and Moses Libitzky.

Len Lehmann is a known name in pockets of the Peninsula and South Bay, both in the tech world, where for 30 years he was an entrepreneur and investor, and in the Jewish community as one of the founders of Kehillah Jewish High School in Palo Alto. He also co-founded the Jewish learning experience Limmud Bay Area, and has been very involved with the rebuilding of his synagogue, Palo Alto’s Kol Emeth.

But the place Lehmann spends most of his time these days is on his property in Portola Valley, tending to several acres of vineyards.

Many successful business people decide to open a winery, but usually they hire a winemaker and additional staff to run it. Not Lehmann. Largely self-taught, he is both owner and winemaker.

Portola Vineyards started nearly 20 years ago as a hobby. Today its grapes produce pinot noir, cabernet, chardonnay and rosé. Lehmann also makes a white port infused with almonds. “We wanted to do something a little more creative,” he said of the port. “It’s whimsical and delightful and really puts a smile on your face.”

Something else he does differently is invite volunteers — whether they be members of his wine club or neighbors — to come help him prune and pick at harvest time. The winery makes about 1,000 cases a year.

“People can come for an hour at a time. It can be meditative work,” said Lehmann. “Life here in the mid-Peninsula is pretty frantic, and some of my neighbors really welcome the opportunity to … work in an agricultural context, to care for the vines and see their annual pattern.”

Several people who picked up the wine bug working as volunteer assistant winemakers with Lehmann have gone on to attend the viticulture program at UC Davis, he said. “That’s how excited they get about the whole process. Sharing my passion for viticulture with neighbors in the community has been so rewarding.”

Portola Vineyards is the name of the wine, which is organic and certified kosher by Rabbi David Booth of Kol Emeth. That makes it the area’s fourth kosher winery — the two largest are Napa’s Hagafen and Berkeley’s Covenant, both Orthodox-certified. Four Gates in the Santa Cruz Mountains is another boutique winery.

Lehmann said the Jewish connection to wine played a major role in his decision to plant his first grapes in 2003, but it wasn’t the only reason. Before Silicon Valley was Silicon Valley, it had a long, storied history of winemaking.

“The Santa Cruz Mountains were really the epicenter of fine winemaking until Prohibition,” he said. “But ultimately, vineyards couldn’t compete with housing and other land uses.”

Lehmann began by planting 2 acres of organic pinot noir grapes that first year, intending to sell them to wineries nearby. But then his wife bought him a small wine press.

“She regrets that now,” he joked. “I started making wine and more wine, and stopped selling our fruit and then buying more fruit.”

Lehmann was mentored by some winemaker neighbors, but did not go through any formal training. Coming from the competitive tech industry, Lehmann appreciates the change of pace in the wine world, where everyone seems willing to share ideas, learn from each other and collaborate.

“There’s a great sense of cordiality and mutual support among winemakers,” he said. “For my first vintages, I was mentored by two local fine winemakers. During their busiest time of year, when they were working 12- to 16-hour days, they found the time to come here and help me.”

Pre-pandemic, the winery was host to occasional Jewish community events and a jazz series, where wine club members could come with a picnic dinner to listen to jazz among the vines. Lehmann looks forward to the time when those social activities can return. “It’s a very local business,” Lehmann said.

The wines are available to U.S. consumers through the Portola Vineyards website, and locally in stores in the South Bay and Peninsula, from San Jose to San Mateo.