Judy O'Brien didn't want to keep the mountain of inscribed plastic cubes, odes to the deals she'd done over two decades, when she left Wilson Sonsini Goodrich & Rosati in 2001.

She tried to recycle them, but deal toys, as it turns out, aren't recyclable, so she threw them out.

"I decided that was not what my life was about anymore," said O'Brien, 59, who was a top partner at Silicon Valley's leading firm.

But she kept one, which now sits in her small office at Obopay Inc., a mobile banking startup in Redwood City where she is general counsel. It's a wooden box with monogrammed scissors and letter opener inside, and a little plaque on top memorializing LSI Logic's April 1983 initial public offering.

At the time, the tech IPO was the biggest ever, raising $153 million, but O'Brien has kept the box because she filed the preliminary prospectus the day before she was due to give birth to her son. Just an associate, O'Brien had written the maternity leave policy at the still-small law firm and she became the first to use it. Twenty-five years ago, in 1984, she became the first woman to make partner at Wilson Sonsini.

In the midst of the macho Silicon Valley culture of lawyers and engineers, O'Brien's career scribed an arc that has become a model of success for women. She led her own practice, hit pay dirt with Wilson's investments during the dot-com boom and then left it all to become a venture capitalist and now the GC of a small but promising company.

"She had succeeded in a world where it was not all that common for woman to succeed in," said Mark Bertelsen, who led Wilson Sonsini for many years.

But the way she climbed the ladder isn't how people think of it today: It was about fitting in with the guys and then working harder than them. "Clients want their work done on time and they don't want to hear that you're sorry that there are baby sitter problems and for whatever reason you can't get the work done," O'Brien said. "The life balance is very, very difficult, and I don't think there's a good solution to it. What I did is wake up at 4 o'clock in the morning for 15 years, 20 years and I worked from 4 o'clock until my kids got up at 6:30 or 7, and then I'd get them to school. ... You have to do things like that to keep up."

And at Wilson Sonsini, a firm never known for its gentility, she taught herself to swear and tell dirty jokes. She would practice swearing at home with her husband, Brad O'Brien, also a Wilson partner.

"I didn't swear before this, and I would say, 'Oh, shit,' and my husband would say, 'That's not the way to say it,'" she said, laughing. "So I actually got quite good at swearing."

VENTURING OUT OF LAW

O'Brien left Wilson right after the go-go days of the late 1990s in Silicon Valley.

She won Recorder affiliate The American Lawyer's dealmaker of the year honor after the 25-lawyer O'Brien group, as it was called, closed 11 IPOs in 1999 for companies like Juniper Networks Inc., Avanex Corp. and VA Linux. She was a steady leader, but away from her colleagues, it was clear she was getting tired.

"My husband said he knew I was leaving Wilson the day one of my clients called me up on Saturday and said, 'We're being acquired,' and after I got off the phone I burst into tears," she said.

She also had enough money to do whatever she wanted. She had stakes in her clients that went public through Wilson's investment arm, WS Investments, as well as her own personal fund. Partners who brought investments to the firm got 10 percent of the firm's stake. So, O'Brien, in just the single instance of Juniper Networks, one of her many clients, probably held stock that was worth about $4.5 million at its peak.

O'Brien doesn't like to talk about her wealth. She still drives a 1998 BMW and lives in the 3,410-square-foot Menlo Park home she and her husband bought in 1985.

When she left the law, she joined longtime client Milton Chang at the newly formed Incubic, a firm that invests only the partners' money into startups. With her kids in high school and her mother ailing, she was able to work part-time, which to O'Brien means 40 hours a week.

"When I worked with her [as a client], I would brainstorm business ideas with her, and she gave me good advice," Chang said. "That's an essential part of a venture capitalist."

She joined Obopay in 2006, after she was captivated by the idea of putting banking services on mobile phones. Here, it means sending money to someone via cell phone; overseas, it would help the many people who have cell phones, but no access to a bank. O'Brien wanted to be a business executive, but Obopay founder and CEO Carol Realini wanted a GC. "I can do that in my sleep," O'Brien said.

At Obopay, she's back to working on weekends and late nights, and she's not getting paid nearly what she made at Wilson.

Of course there's some upside if the company hits it big, but O'Brien said at this point it's less about money and more about what she wants to do.

"It appealed to my global interest, my fascination with different cultures, my do-gooder instincts," she said. "It enables commerce in the developing world."

Her husband also observed that O'Brien always likes being in the mix. "She's very interested in business; she enjoys the relationships she has in the business community," he said. "It's kind of something where you're in or you're out, and so you have to play full-time to be taken seriously."

She's been helping raise venture capital, dealing with banking regulators around the world, and closing big deals with companies like MasterCard. After one particularly contentious deal with Essar, an Indian company, Realini presented O'Brien with a pair of pink boxing gloves that now hang in her office.

"She's a strong negotiator, but she does it with a very soft approach," Realini said.

NEGOTIATING STYLE

Former colleagues liken O'Brien to the current Wilson CEO Steven Bochner: a high-powered partner at Wilson who doesn't have sharp elbows and is respected by most of the firm.

At the negotiating table, lawyers who worked opposite her on deals say O'Brien set the tone by not trying to one-up opposing counsel just to make an impression.

"She knows that when you have an issue, you don't argue it in front of the client," said William Sherman, a corporate partner at Morrison & Foerster. "She'll take it offline so people don't get in the business of having to impress their clients with how tough they are."

O'Brien has a firm, confident presence, but she's also personable. Imitating what her husband says to her after she goes running/talking with a friend (her husband might say it's talking/running), she took hold of the sides of a reporter's face, saying, "I see you got a lot of exercise."

O'Brien's career hasn't been all roses. Her name recently came up in connection with the government's stock option backdating lawsuit against Lisa Berry, who was general counsel at KLA-Tencor Corp. and Juniper, two of O'Brien's clients. Berry's lawyers say that the GC sent a memo to Larry Sonsini -- cc'd to O'Brien -- that discussed backdating.

"I learned about the backdating at KLA and Juniper and Brocade from the San Jose Mercury ," she said. "It was, 'Oh my god, how could this be?'"

Even with Sonsini as a mentor, life as a young female partner was sometimes difficult.

Companies expected their lawyers to be men and she was forced to bring men along to pitch business. But eventually, she was respected on her own. So much that on one occasion she brought a gaggle of Japanese executives from Kawasaki Motors Corp. to her house to close a deal while she put her two young kids, Conner and Lauren, in their pajamas. Her son took a liking to one of the execs and sat in his lap.

"They were lovely," she said. "We got the deal closed."