How Mr. Clean upset San Francisco politics

Nick Josefowitz wasn't supposed to win elected office in a city full of contradictions.

San Francisco has become the center of a digital world. Yet its political campaigns are largely analog operations, relying on printed material and the postal service to communicate with voters.

It has an all-Democratic government where candidates fight over a million shades of blue. Yet one Republican managed to get re-elected for 24 years.

It has a dirty, overcrowded and outdated public transportation system riders love to hate. Yet few know there is an elected board they can hold responsible.

All that changed this year when 31-year-old Josefowitz went on Facebook, publicized the failings of the BART board and ousted a Republican long supported by the Democratic establishment.

Josefowitz, a wealthy clean energy entrepreneur, had a simple message: Clean up BART.

The slogan was figurative and literal, considering the stench of urine in downtown stations and the fact that incumbent James Fang once paid $22,000 in fines for laundering Democratic campaign money in the 1990s.

Winning was not simple. Josefowitz was new to San Francisco and dared to take on the powerful Fang family, which has supported local politicians for decades. Many top Democrats endorsed Republican Fang. They even blocked fellow Democrat Josefowitz from appearing on their official slate card.

Why so much wrangling over the little-known BART board? Because it handles billions of dollars in contracts for a regional transportation system that includes power plants and development of housing and retail around its stations.

Attacks on Josefowitz came early. College essays he wrote a decade ago circulated around town out of context, trying to discredit him as not in line with San Francisco values.

“I knew what I was getting into. A bunch of people advised me about how aggressive James Fang is,” Josefowitz said. “The machine wants to keep him in power, but we don't have to accept that the crony insider is always going to win. We should live in a city where if we feel things aren't working we can change them.”

Other well-intentioned, good-government candidates tried to challenge Fang over the years and were summarily steamrolled. But Josefowitz raised $200,000 (partly from his tech friends) and then put another $200,000 of his own money into the campaign.

Josefowitz's war chest allowed his important message to be heard: BART must embrace innovation or be left behind while the Ubers, Teslas and Googles of Silicon Valley determine the future of transportation.

“When Nick called for innovation, he brought it into the campaign itself,” said his political consultant Nicole Derse of 50+1 Strategies. “He pushed us to spend a larger percentage of the budget on social media than any race I've worked on. If we just put his name on mail pieces, he wouldn't have won. We used the right message to get people to pay attention where they are online.”

Josefowitz's campaign also knocked on 90,000 doors. He used a smart phone app from Organizer, a San Francisco-based startup. It tracked responses in real time, eliminating the need for clipboards of paper and labor-intensive data entry.

Then there was Josefowitz's idea to hand out 60,000 “Clean up BART” sponges at stations and doorsteps.

Political insiders expected a large Chinese electorate to keep Fang in office. Yet Josefowitz did well in Chinese precincts. All five Asian supervisors at City Hall endorsed Josefowitz.

Some criticize Josefowitz's ability to self-finance much of his campaign. But we celebrate wealthy individuals throughout American history — from the Roosevelts to the Kennedys to Bloomberg — who became public servants and addressed tough issues they could have easily ignored.

“I was raised with the Jewish concept of tikkun olam,” Josefowitz said. “It's the notion that the most important thing we can do is work to improve people's lives.”

Joel Engardio lives west of Twin Peaks. Follow his blog at Email him at