Adithya Sambamurthy/The Bay Citizen

Joanna Rees, center, campaigning for mayor on a bus in the Sunset district

How’s this for a Harvard Business School case study: The Bay Area is renowned for its entrepreneurial culture and the fortunes amassed by its technology elite. But leaders from that world have been notably unsuccessful persuading voters that business smarts qualify them for elective office. (Think Meg Whitman, Carly Fiorina and Steve Westly.)

Can a member of this tribe win an election here?

As she campaigns to be elected San Francisco’s next mayor, Joanna Rees, a moderately successful venture capitalist and a Columbia MBA, is determined to prove that the seemingly immutable laws of local politics do not apply to her.

Rees, a 49-year-old mother of two, has spent the past two years visiting coffee shops and churches and riding Muni buses (in four-inch Chanel pumps) to chat up voters — employment anxiety dominates the conversations — as she angles to break the business elite’s string of electoral losses.

A formidable networker, Rees has an impressive list of campaign contributors: Mark Pincus of Zynga, Marc Benioff of Salesforce, Reid Hoffman of LinkedIn, Craig Newmark of Craigslist, assorted Pritzkers and Bronfmans and Coppolas, the wife and the sister of former Mayor Gavin Newsom and the musician Quincy Jones.

As Rees makes her rounds, with a business-friendly message that puts her well to the right on the San Francisco political spectrum, she is winning some support. “She is as smart as hell, a real person, not political,” said James Ludwig, former head of Saks Fifth Avenue in San Francisco.

Impressed by her focus on public-education innovation and her business savvy, Ludwig recently sent out hundreds of letters on Rees’ behalf. Hilary Newsom, the former mayor’s sister and president of the PlumpJack Group, has done the same.

Yet Rees remains mostly unknown. The mayoral race has many contenders, with old City Hall hands — David Chiu, Bevan Dufty, Leland Yee, Dennis Herrera, Phil Ting, John Avalos and Michela Alioto-Pier — crowding the field. In a March poll, Rees’ name did not even register. The powerful San Francisco Labor Council has not included her among the seven candidates invited to speak to 500 union delegates next week.

Rees’ problem is money. She has it. (She and her husband, her partner in a venture capital firm that is now being dismantled, live in Presidio Terrace, a gated enclave with uniformed guards.) But she has, as yet, refused to spend it.

Adithya Sambamurthy/The Bay Citizen

Joanna Rees' campaign literature at a bus stop in the Sunset district

Though she stands to collect as much as $900,000 in public financing by agreeing to campaign-spending caps, Rees herself has not yet contributed a single dollar. And under the campaign-spending caps, none of her well-heeled contributors can give more than $500.

“I am an entrepreneur who bootstrapped my way into the old boys’ club of venture capital,” said Rees, who is not affiliated with a political party but has contributed to Democratic candidates, including the liberal Senator Barbara Boxer. “I have been down in the trenches with entrepreneurs, rolling up my sleeves, to help turn a small idea into something real. That is why a grass-roots field campaign is so compatible with who I am.”

“I am raising money the old-fashioned way, supporter by supporter,” she said.

Corey Cook, a University of San Francisco professor who organized a candidates’ forum last week, sees promise for “someone who can really claim to reform from the outside, who is effective on the business side.” However, Cook notes, “that’s not a message that traditionally plays well in San Francisco.”

And, of course, Rees cannot win if most voters do not know she exists.

“She cannot just go to bus stops and shake hands with strangers,” said Nathan Ballard, a Democratic strategist and former adviser to Newsom. Ballard is not involved with any of the mayoral candidates, though he is one of the many local political operatives Rees has consulted.

“I would advise her to write a big check,” he said. “She needs to help herself.”

And that, even if you didn’t go to business school, is Marketing 101: Under-investing when launching a new product is a recipe for, well, nothing.

This article also appears in the Bay Area edition of The New York Times.