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Why Ellen Pao was doomed to lose

March 30, 2015, 11:01 AM UTC
Closing Arguments Made In The Discrimination Case Pao v. Kleiner Perkins Caufield & Byers LLC
Ellen Pao, former junior partner at Kleiner Perkins Caufield & Byers, exits state court in San Francisco, California, U.S., on Wednesday, March 25, 2015. After two days of closing arguments, a month of finger-pointing testimony from both sides, the day of reckoning for the venture capital firm Kleiner Perkins Caufield & Byers has finally come in the sex-bias trial that has gripped Silicon Valley. Photographer: David Paul Morris/Bloomberg via Getty Images
Photograph by David Paul Morris — Bloomberg via Getty Images

It may be politically incorrect to say, but it’s true that anyone can sue. And plaintiffs tend to be outliers. Like whistleblowers, gadflies and other disruptors, plaintiffs are usually people who don’t get what they want the way that the rest of us do. So, they sue.

This appears to be the case with Ellen Pao, the onetime junior partner at Kleiner Perkins Caulfield & Byers who sued the venture capital firm for gender discrimination and, with Friday’s verdict, lost her three-year legal battle. I don’t know Pao well, but in 2011 she was on a panel that I moderated. I recall wondering to myself at the time how a woman so reticent and obviously insecure could have advanced so far in fiercely competitive Silicon Valley.

Already I envision angry comments pouring in—which is why I didn’t write about Pao until after the trial ended. But I think my view is worth sharing now, for several reasons: Because I’ve studied and written about women and power for 20 years, because I know Kleiner and many of the firm’s partners, and because the problem that Pao’s lawsuit spotlighted—the lack diversity in the VC industry—is worth ongoing attention.

Ellen Pao was, quite simply, ill-equipped to take on this important issue. She was still at Kleiner when I interviewed her on a panel at a BlogHer conference in Silicon Valley four years ago. My first question was: What is the best personal asset that helps you succeed? The two other panelists, serial entrepreneur Kim Polese and Omnicom(OMC) EVP Janet Riccio, talked about “galvanizing a team around a mission” and “bringing other women up in the organization,” while Pao’s answer was this: “I’m bad at self-promotion. I like to help people and help entrepreneurs.”

I appreciated Pao’s candor, but she never swayed from her negative tone. When I asked each of the panelists what was their biggest career mistake, Pao replied, “I didn’t take advantage of all the opportunities in front of me, didn’t ask people to coffee [because they were busy], and wish I had.” When someone in the audience asked the panelists if they had to change their style to succeed in male-dominated industries, Pao answered affirmatively and explained, “I’m an introvert, not a self-promoter. Our firm has a lot of interrupters, and I wasn’t raised to be like that.”

A daughter of Chinese immigrants who has three Ivy League degrees, Pao eventually learned to activate her aggression, as her lawsuit against Kleiner Perkins indicates. No one but she knows who and what caused her to take on Silicon Valley’s most famous VC firm, but I have to believe that her husband, Buddy Fletcher, had something to do with it. Alphonse “Buddy” Fletcher, Jr. is a hedge-fund manager who is facing client lawsuits and government probes related to his failing money-management business.

I interviewed Fletcher 21 years ago for a story called my “Don’t call me Slacker,” about America’s most successful twentysomethings. At the time, he was 28 years-old, running his own firm, and getting chauffeured around Manhattan in a Bentley—the fringe benefits of having sued his former employer, Kidder Peabody, for short-changing him on his bonus. Fletcher, who is black, had won $1.3 million from Kidder, then owned by General Electric (GE), and he was seeking $5 million more, claiming racial discrimination. “Bite off more than you can chew. Then chew it” was Fletcher’s philosophy, he told me. That advice came from his grandmother.

Fletcher didn’t appear at his wife’s trial in Silicon Valley, and the jury of six men and six women was not allowed to hear about his legal and financial troubles. But the truth about Ellen Pao and Buddy Fletcher, whose extraordinarily complicated lives Fortune chronicled in a 2012 cover story, suggests that she was hardly the ideal change agent to help fix the gender ratio in the VC industry, where 94% of the partners are male.

“I think it takes someone with a little bit of crazy to actually stand up and take a stand on these issues,” wrote one Silicon Valley observer, Sue Decker, who took her two young daughters to last week’s closing arguments because she believed this, regardless of the verdict, may be “a watershed moment” for diversity. Decker is a former president of Yahoo (YHOO) who now serves on the boards of Berkshire Hathaway (BRKA), Costco (COST) and Intel (INTC)—and she’s right. Pao deserves credit for catching America’s attention. But if we expect to make real progress, we’d better hope for more effective activists than Pao could ever be.