Lessons From 7 Women Who Broke Wall Street's Glass Ceiling

The intersection of Wall Street and Hollywood Boulevard hasn't been showing the best side of the investment world -- whether giving us Leonardo DiCaprio howling at the high-finance moon in "The Wolf of Wall Street," or the cynical, cold-blooded capitalism that fueled the housing crisis in "The Big Short."

And if you stop to think about it, those wolves weren't exactly female, were they? Nor were the big shots in "The Big Short," though in one memorable scene, a woman plays the spineless, clueless Standard & Poor's gatekeeper.

[Read: How to Choose Between a 401(k) and an IRA.]

In an investment world lambasted -- and in many cases, rightfully so -- for its unmitigated greed and moral corruption, women are often shunted to the side as though they could never prove effective, let alone corrective. For them, the glass ceiling might as well be a dark tinted, bulletproof funhouse mirror.

"I realized a few things early on starting out in this career: It is male dominated and most of the men are white," says Francesca Federico, co-founder and principal of Twelve Points Wealth Management in Boston. Back then, she was 21; the only other women in her Morgan Stanley office (there were just three) were older than 50.

"It's an old boys' club, usually with men pulling other men in," Federico says. "When I ask most advisors how they got into this business, I usually expect the same answers: My father was in it, a college alumnus helped me, a relative helped me. I think women have had a hard time breaking in because there have never been that many to begin with."

The stories women tell about their attempts to rise in the investment milieu tell a collective tale of long odds and short ends of the stick. Still, some such as Federico have managed to find their footing and achieve a measure of success. Here, seven women share their observations and experiences on the way to beating Wall Street expectations.

Learn to clear the confidence fence. Many aspects of the working world have achieved a level of gender equality, so why isn't investment one of them? "A huge factor is simply confidence: Most women don't have it," Federico says. "Typically, women are shy and aren't as loud or outgoing as the men. And if they are, they sometimes get seen as too aggressive."

[Read: 4 Tips for Women to Overcome Their Financial Fears.]

Don't give in to grave expectations. Female investment neophytes have to prepare for maddening obstacles that sometimes border on the bizarre. Last year, Laurie C. Kamhi was recognized by Private Asset Management magazine as one of its 50 most influential women in private wealth. But the current director and partner at HighTower's LCK Wealth Management had to sidestep curious rejections first. "While interviewing for jobs early in my career, two top investment banking firms brought me in after looking at my resume and assuming that Laurie was a nickname for Lawrence," says Kamhi, who is based in the New York City area. "Once I arrived and they saw I was a woman, the interviews were over."

Turn the boys' club on its ear. At the desk of a male financial advisor, a husband-wife meeting too often turns into a triad where the woman gets left out. "When asked, the vast majority of women say that they are financially illiterate," says Binney Wietlisbach, president of Haverford Trust in the Philadelphia area. "But women advisors may have an advantage when advising female clients as usually women appreciate the softer relationship skills that female FAs often possess. Additionally, women FAs may be less intimidating and threatening while trying to engage the female client in conversation around financial matters."

Hold your ground. It's a lot more common for men to talk down to women in the financial world than the other way around. Katalin Takacs-Haynes, an associate professor of management at the University of Delaware, tells of reviewing a messy venture capital funding deal during her time in the private sector, only to conclude that the investment bankers pushing it didn't have their numbers straight. "I told them at a meeting that their numbers were off and that funding this deal was not in the best interest of my employer," she says. That's when one banker raised his voice and questioned her credentials. "I told him to back off and that I knew what I was doing. He then said, 'Did I ruffle your feathers, young lady? Venture capital is a tough business and you'd better get used to it.'"

Remote work raises remote chances. Despite gains in sharing the division of labor, "Women still tend to be the primary caregivers in their personal lives," says Allison Alexander, a certified financial planner with Savant Capital Management in Rockford, Illinois. "Wealth management is not conducive to taking breaks or sabbaticals from the workforce for purposes of child rearing or caring for aging parents." Enter the Internet: "The job offers an enormous amount of flexibility to work outside an office setting," she says. "With the exception of face-to-face meetings, much of the work can be done remotely."

[Read: Why Fine Art Can Beautify Your Portfolio.]

Crunch a different set of numbers. At first glance, the digits don't look encouraging. "Women are nearly 50 percent of the workforce, yet still only represent less than 25 percent of the investment industry," says Kathleen A. Grace, managing director at United Capital and based in Boca Raton, Florida. She also experienced pay discrimination while working at an investment and private banking firm -- when a younger male colleague with the same title and position, and producing less revenue, was paid more. But she cites encouraging numbers from a decades-long study by Terrance Odean at the University of California, Berkeley. "Single female investors outperformed single men by 2.3 percent, female investment groups outperformed male counterparts by 4.6 percent, and women overall outperformed men by 1.4 percent," Grace says.

Why break the glass ceiling when you can make your own way? Beth Blecker, the CEO of Eastern Planning Inc. in Pearl River, New York, manages about $300 million. You'd think that for any woman, that kind of standing would earn unconditional respect. "But on Wall Street, women need to be better than their male counterparts in order to be considered good," she says. "It is a male-dominated world that women can only break through by working harder and doing more -- and even then acceptance is not guaranteed."

Yet while the movies of the day portray Wall Street as cutthroat and carnivorous, "the same trait that makes women vulnerable on Wall Street -- their compassion -- can make them very successful as true wealth managers, especially if they are willing to explore the independent channel." Blecker should know: Much of the money she manages comes from high-net-worth women.

A former longtime staff writer, editor and columnist at the Chicago Tribune, Lou Carlozo writes about investment for U.S. News & World Report, and personal finance for Money Under 30 and GOBankingRates. He is based in Chicago. Connect with him at linkedin.com/in/loucarlozo.