Onetime VC Joanna Rees Sees Little Traction in San Francisco Mayoral Race

Joanna Rees has been riding buses and knocking on doors to drum up support for her campaign to become the next mayor of San Francisco, and she’s been doing it in her Chanel pumps, according to at least two newspaper accounts.

It’s easy to laugh at the image, but the onetime venture capitalist, who reportedly shuttered the San Francisco office of her firm VSP Capital in May, is clearly taking her run at the office seriously.

In February, she opened a campaign office seven blocks from her home in San Francisco’s Richmond District. She hired top-notch Democratic strategist Ace Smith, who is credited with securing wins for L.A. mayor Antonio Villaraigosa, and California’s lieutenant governor, Gavin Newsom. And Rees has attracted many well-heeled donors, raising $365,000 so far from Zynga founder Mark Pincus, LinkedIn founder Reid Hoffman, and Brook Byers of Kleiner Perkins Caufield & Byers, among about 950 other private donors. (She has raised an additional $470,000 in public financing.)

Still, Rees’s campaign appears to be sputtering. According to the San Francisco Chronicle, which profiled Rees this morning, the 49-year-old “is barely registering a blip in polls.” And “Ms. Rees cannot win if most voters do not know she exists,” the piece concluded of the November race.

Improving Rees’s odds of a win remains challenging for a variety of reasons. First, she’s facing a crowded field of at least 11 serious contenders, many with deep ties to San Francisco City Hall, like Michela Alioto- Pier, a longtime member of San Francisco’s board of supervisors (and granddaughter of a San Francisco mayor) and the city’s incumbent mayor Ed Lee.

Indeed, displacing Lee alone is a tall order, suggests Eric Jaye, a San Francisco-based political consultant who represents another mayoral candidate. “We have a popular incumbent mayor who can command enormous attention by virtue of that incumbency,” says Jaye. It’s “hard for any candidate to build a platform for candidacy” as a result.

And Rees has a particular challenge, suggests Jaye, owing in part to those Chanel heels.

“As a venture capitalist, people seek you out and you have a very positive feedback loop,” says Jaye. But “as a candidate for mayor of San Francisco, ‘venture capitalist’ means something else in San Francisco than it does on Sand Hill Road, and it’s not necessarily a positive to many people in various precincts of the city.”

Not last, it isn’t clear that Rees — or anyone, frankly — will do well in what will be San Francisco’s first mayoral election to be decided by ranked-choice voting, which will ask voters to list their top three choices on election day. The idea is to avoid a costly run-off. If no candidate wins more than half the votes, last-place candidates get eliminated, and their second- and third-place votes become redistributed until someone wins a majority.

“What to watch in this race are which candidates make informal alliances to encourage their supporters to consider their second and third choice” for mayor,” says Garry South, a Santa Monica, Calif-based political strategist. “It’s like playing three-dimensional chess. You can’t just say, ‘Vote for me.’”

It isn’t clear that Rees has the unifying skills necessary to play the game. Smith, Rees’s valuable strategist, dropped her in March. He’s now supporting the campaign of Lee, a veteran civil servant who became San Francisco mayor when Newsom was sworn in as lieutenant governor in January. (At the time, Lee said he had no intention of running for mayor. He publicly declared otherwise earlier this month.)

More, while Rees plays up her success as a venture capitalist, many industry observers still recall that investors in the firm’s third and last fund pulled the plug on their commitments following infighting among  the firm’s partners.

We sent an interview request to Rees’s Twitter account (@JoannaRees), and we’ll update this post if she responds.