Executive Suite: Hedge Fund Founder Whitney Johnson On Failing To Step Up And Wall Street ‘Suits’

Every week The Grindstone interviews an influential woman in the world of business. We scour our brains and hearts to come up with strong, successful women who not only inspire us, but will also inspire you. No industry is off limits, no interview subject too controversial.

Whitney Johnson is quite a woman. She never imagined working on Wall Street as a kid growing up in San Jose, California but she ended up in New York with her husband when he went to Columbia to get his PhD. Though she confessed in her TED Talk that she was terrified to even go out in New York without her husband she knew she needed to get a job. But she figured she was at a disadvantage as she had a degree in music, didn’t attend an Ivy League school, had no connections on Wall Street, was a woman and had no confidence, according to her. But she could type super fast and so she got a job as a sales assistant or as she says, a “fancy name for secretary.” In her TED Talk she describes how her office or bullpen was straight out of the Tom Wolfe novel Bonfire of the Vanities. “It was essentially a locker room for 20-something guys aspiring to be masters of the universe if only they could open one more account,” she said. “The pressure was so intense and testosterone was so high that they went for the hard sell. And inevitably there was a lot of smack talk.” But as the men told their clients to “Throw down their pom-poms and get in the game,” Whitney decided to take this advice as well. She started taking finance courses at night and eventually made that very hard transition from administrator to professional investment banking analyst. She disrupted herself, she says.

She disrupted herself again a few years later when she became an equity research analyst and then a few more years later when she left Merrill Lynch to become an entrepreneur and start her own firm. And now she is the president and co-founder of the hedge fund Rose Park Advisors and a regular contributor for the Harvard Business Review blogs. After conquering Wall Street she decided she wanted to help other women pursue their dreams. She started a blog called  Dare to Dream and also wrote the book Dare, Dream, Do: Remarkable Things Happen When You Dare to Dream. Having invested in her own dreams, Whitney is passionate about encouraging others to take stock in theirs. She and and her husband reside with their two children in Boston, Massachusetts. We were lucky enough to get to pick her brain for a bit about Wall Street, writing on the side and lessons from shows on the USA Network.

Do you think there is too much hype over the male-dominated atmosphere of finance or do you find it is true?

Apart from statistics such as 90-95% of all VCs are men, my experience bears out that there simply isn’t a level playing field. At the end of 2004, I’d had a great year at Merrill Lynch. From stock-picking to commission dollars to peer reviews, I was top of the class. Surely I was on solid ground when I conveyed to management that I expected to be a top 10% earner. Instead, I was told I was out-of-line. And yep, you guessed it, my pay wasn’t in the top 10% — in fact, it wasn’t even in the top quartile.

Despite the glass ceilings and walls, I am seeing a lot of women in their 20s and 30s moving things forward quite remarkably. Which makes me wonder if I am not, in fact, my biggest barrier.  There’s a television show called Unforgettable that I like. Just last week, the main character was explaining to the male protagonist that she missed questions on purpose on a test at work so people wouldn’t know how smart she was because she didn’t want to be a pariah. And I thought, I used to do that all the time. I wouldn’t let people know how smart I was.  But as I got good at not being competent, I actually cultivated the belief that I wasn’t competent.

As for a strategy as a a minority, number one we need to acknowledge the fact that the glass ceiling is a reality. Number two: Even with that reality, “I am still in charge of me.”  Number three:  don’t downplay the strengths that I have as a woman, like emotional attunement.   Because, if I can walk in a room, be uber-competent, and also read a room — that’s a real strategic advantage.

Can you tell us about things you have done you considered to be a failure in your career and how you learned from them?

As a high school student, I definitely failed to step up, like like not taking calculus in high school because I was afraid I wouldn’t get an A.   I try to be more fearless now.  For example, I am taking the Code Academy class.  And — I tell young women to take calculus, the hardest finance class — whatever field you are in.  Once you are actually out of school, no one will care of if you got a B.  You just need to know the material.

Another notable failure was when my husband and I backed a magazine.  At one point, it looked as if it would be quite successful, with circulation reaching 100,000, but then it eventually imploded.  It was very devastating emotionally and financially. But it was an important lesson for me. I learned that I need to set clear boundaries.  As a woman, this is especially hard.  When I meet men professionally, there’s an underlying expectation that we are going to try and do business.  With women, are we doing business or looking at becoming friends?  It’s important to figure that out.  But realistically you can’t.  So I’ve learned to just start by collaborating on small things.  Also, I’ve learned that I need to accurately assess prospective partners. Every partner has his or her weakness.  To be expected. The important piece is be sure that the combined weaknesses aren’t toxic.  Finally, I now understand that I need to ask questions like, “How are we going to work together? Who is going to own what? and “Who will own this piece of the pie?” And I do.

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