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LearnVest CEO Alexa Von Tobel: What Women Do That Holds Them Back

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In first grade, Alexa von Tobel decided to be president of the United States. A few years after that, she settled on her ultimate -- and perhaps most ambitious -- career goal: entrepreneur.

Today, von Tobel is the founder and CEO of LearnVest, a startup focused on offering personal finance advice to women.

Motivated by her mission to help women take control of their bank accounts and bottom lines, von Tobel created LearnVest in order to do for personal finance what Netflix has done for movies: make it easily accessible, convenient, personalized and reasonably priced.

The idea for the company, which she founded in 2009 after taking a leave of absence from Harvard Business School, came to her after a realization that she graduated from an Ivy League university without ever taking a course in personal finance. Despite having a bachelor's degree from Harvard and experience working as a trader at Morgan Stanley, she did not know how to intelligently manage her own money and was unable to find satisfactory guides to help do so.

"Having command over your finances is a huge aspect of taking command over your life, from changing jobs to who you end up with, to having the courage to ask for raises," explained von Tobel.

She credits her leadership skills to growing up with two older brothers with whom she struggled to keep up and struggled keep in line.

"My parents used to joke I was the one who was always trying to organize them because they were always getting in trouble," she said of her brothers. "I always wanted to hang out with them so always made sure I was comfortable doing things like playing sports that I had no interest in playing, and putting myself out of my comfort zone."

In an exclusive interview for The Huffington Post's Women in Tech series, von Tobel explained her take on what women do that holds them back, facing fear and finding mentors.

What's the single most important lesson you've learned from launching your company?
How to face fear. Learning how to do that really makes you invincible because you stop being scared. For everything that scares me, I think through worst-case scenarios and realize it's not that bad -- at the other end of it, I'm still alive, I'm still healthy. It's okay to fail.

I also think through what the 90-year-old Alexa would say, which helps put everything into perspective. Once I start thinking like that, everything started having lot of clarity.

What's the best advice you've ever received?
The best advice I ever got was from someone who once said to me, "If you knew what it takes to create a startup you'd never start." That was the most real sentence I ever heard. If you knew everything that it takes to start a company, you wouldn't get out of bed in the morning.

I think the best advice is to really build the smartest and best team, then take great care of people on your team. That love makes people excited to work and it's the committed, passionate people that help create magic, which is what you create when you're the CEO of a startup.

How do you find those people?
It's what I call well-finessed stalking. Find out who's the best, and smartest in your space and go after them.

You've had some amazing mentors, such as Catherine Levene, former COO of DailyCandy, Ann Kaplan, the first female partner at Goldman Sachs, and Richard Branson, whom you met last year. How have you gone about connecting with these people?
It's simple -- relationships don't work if it's not genuine. If I seek someone out, I seek them out as a friend and confidante, and I don't seek out relationships that I don't want. I treat everyone like a friend.

SOUND BYTES: Alexa von Tobel on...
Her indispensable gadget: Her iPhone

Her favorite app: The game SET

Her favorite Twitter account: Steve Blank (@sgblank)

Her "required reading" recommendations: Richard Branson, Losing My Virginity ("It gave me courage when I dropped out of business school," said von Tobel. "I read it cover to cover twice.") and Ayn Rand, The Fountainhead

What is the greatest challenge you've faced as a leader?
For me it was really important getting comfortable with risk. Getting LearnVest going from when I dropped out of business school -- and there was nothing -- to building it up today was a really scary time, but also a very real time. Any day that you catch me there are good days, bad days and scary days. The uncertainty doesn't go away, but being comfortable with that uncertainty is what matters. The motto that goes through my head is, "Take one day at a time."

What is something that you failed at?
Where do you want me to start? We should have built products sooner. We could have, but we were so thoughtful about what our products would be, and we worked hard to make the best products at the expense of things moving slower. That being said, if you ask anyone else they'll say we're moving at lightening speed. But I think we can always move faster.

Trying to raise seed funding was grueling. We didn't fail--it took a total of six months to close the round and ultimately we succeeded--but it felt like a lot of failure when people said, "I need to see more traction or a product," "Come back when you make 'XYZ' progress."

Do you think that the skills men need to succeed as entrepreneurs are the same as the skills women need?
I really stay away from the whole men-women debate when it comes to skills, because I think there are so many different things it takes to be an entrepreneur. I never thought of myself as a female entrepreneur or a male entrepreneur. It's hard enough to be an entrepreneur, you don't break it down more than that.

Entrepreneurial people rely on strengths they have. If your strength is that you are incredibly determined and detail-oriented, then that's that. My strengths are that I am the hardest worker, I have tons of energy and when I commit, I commit a million percent.

What is something that women do that holds them back?
It's an obvious one, but one that's very important to me because of LearnVest: Having command over your finances is really critical to being the person you want to be. It doesn't mean being a rich person, but it means being a person who can follow the path they want to and create new paths for herself.

The other thing is being comfortable with risk. Taking big leaps is really scary for anyone, including women. Having taken my own risks and jumps, and having been less comfortable with it, risk wasn't easy for me.

Find more profiles of pioneering women in tech -- including Google's first female engineer, the chairman of Gilt Groupe, and NASA astronaut Tracy Caldwell Dyson--on HuffPostTech here.

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