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How Alexandra Lebenthal has taken on Wall Street's boys' club

Alexandra Lebenthal speaks with CNBC's Jon Fortt.
CNBC
Alexandra Lebenthal speaks with CNBC's Jon Fortt.

Alexandra Lebenthal is a third-generation Wall Street power broker. Her grandparents started Lebenthal & Co. 92 years ago, helping to redefine the municipal bond business.

Her company has seen better days — she's in the process of selling much of it to South Street Securities Holdings, though she'll maintain control of the corporate bond operation.

Through the years, Lebenthal has shown a determination to maintain the family business, and to blaze a path in the boys-club world of finance. I sat down with her to talk about growing up in New York's financial world, her view of gender imbalances in the corporate world, and how she feels now that her college-age daughter has surprised her by deciding to follow in her footsteps.

Here are some of her insights:

Find your gym

Though she grew up watching her grandmother Sayra run the family business, Lebenthal says she realized she still needed confidence boosts. An all-girls school on the Upper East Side of Manhattan, the Nightingale-Bamford School, provided that environment in high school.

Lebenthal particularly remembers headmistress Joan McMenamin: "If she said it once, she said it every single day: 'Girls, you can do anything you set your mind to.' For anyone to hear that over and over, it does drill into you. … You always need to hear it, at every stage of your life. Even as you're a grown-up."

The universal lesson here: Even after we've heard the motivational speeches and seen success up close, we still need a tune-up now and then. Find the places and people that help you shore up your weaknesses and gain confidence in your strengths.

Never hear no

When Lebenthal decided to rebuild her business 10 years ago after selling control, Merrill Lynch, which had acquired the family name, at first refused to sell it back to her. She didn't give up.

"That is one of the things I have learned in life, is, never hear no. Just think of it as a placeholder until you figure out how to get to yes."

How many times did she hear no in that case before she figured it out? "I got four, and one of them was from Stan O'Neal [the CEO at the time]."

She also remembers a time in the 1970s when her father faced a crisis that nearly sank the business. Things worked out in the 11th hour. "As an entrepreneur, you're always going to have moments of great challenges. And the trick is keeping yourself together and getting through them."

Stand out

Lebenthal never has been much of a wallflower, and that's reflected in her fashion choices. Don't expect to see her in a boxy, black power suit.

"Believe it or not, I actually embrace being in a room where I'm the only or one of few women, because I think, 'Hey, here's my opportunity. I don't look like everyone else. I don't dress like everyone else. So let me be in as bright colors and big jewelry as possible, and just figure out, OK, how can I make this ultly be something beneficial for me in business.'"

It's a lesson in taking the trait that otherwise could be a disadvantage and finding a way to make it work for you.