Founder, The Huffington Post
www.huffingtonpost.com

Becoming fearless. Could there be a more perfect topic for women entrepreneurs?

And who better to write the book on it than Arianna Huffington, who has launched and re-launched many times in her life, sometimes resulting in spectacular success, sometimes not.

Now Arianna, founder of the wildly popular political Web site The Huffington Post, is riding a wave of success and promoting her latest book, ‘On Becoming Fearless.’

Here she talks with Ladies Who Launch about the tug-of-war between desiring security and living your dreams, being rejected 36 times, the three best business lessons learned from mom, her favorite blogs, the new Dixie Chicks documentary, and more…

Why She Wrote ‘On Becoming Fearless’

Arianna: “I wrote the book for my teenage daughters. Looking at them, I was stunned to see all the same classic fears I was burdened with: How attractive am I? Do people like me? Should I speak up? I had thought that with all the gains feminism has brought, my daughters would not have to suffer through the fears I did. Yet here is our younger generation, as uncertain, doubting, and desperate as we were, trying to fulfill the expectations of others.”

How She Overcame Fear of Speaking Out

“One of the biggest fears I had to overcome was my fear of speaking out. In the book I write about how when I went to Cambridge, my thick Greek accent was a great source of fear — especially since I wanted to be part of the Cambridge Union, the school’s famed debating society. I conquered this fear only because my love of politics and debate was stronger than my fear of criticism and failure.”

How to Become Fearless about Money

“Even today, a surprising number of us still think that it’s the man’s job to make and understand money. Far too often, we delegate this responsibility and don’t learn enough about money, so of course we fear it. That’s where we have to start. We can never be fearless about money until we demystify it and take charge of it. We begin to become fearless about money when we start to value other parts of our lives more than we value our bank accounts.”

How to Become Fearless about Work

“Taking credit for our work and accomplishments, and fearlessly negotiating for compensation can be interpreted as ambitious and aggressive. But if you act timid and unimportant, that’s how you’ll be perceived. We have to let go of the idea that we must be sweet all the time if we’re going to be ‘real women.’”

How to Become Fearless about Leadership

“The most important thing is not to internalize the attacks on us, and to realize that any time we speak out against injustice or against the status quo, we are going to have attacks leveled at us. Our culture still isn’t comfortable with outspoken women. As Marlo Thomas famously put it, ‘A man has to be Joe McCarthy to be called ruthless. All a woman has to do is put you on hold.’ The best way to neutralize this kind of attitude is through laughing at it.”

Launching The Huffington Post

“Ever since college, I’ve enjoyed bringing together people from many different parts of my life and facilitating interesting conversations. These conversations have taken place around dinner tables, or at book parties, or on hikes with disparate groups of friends. With The Huffington Post, the idea was to take those conversations — about politics and books and art and music and food and sex — and bring them into cyberspace, creating a one-stop shopping site for news and opinion, with an attitude, in real time. So HuffPost was really an extension of what I’d already been doing.”

Secrets of Success

“I never discount the role that luck played in our success! Seriously, specific conditions led to the success of HuffPost. We arrived in the midst of a ‘perfect storm’ for a political news and blog platform. Both Internet news and ‘blogging’ have become wildly popular and the primary sources of information for millions of Americans. And our specific point of view allowed us to quickly create a HuffPost brand.”

How She Raised Funding?

“It was a combination of family and friends, then ads starting paying the rent. And we’ve just had an infusion of financing from a pair of venture capital groups.

Greatest Business Challenge - 36 Rejections

“It happened back in my mid-twenties when I was writing my second book. My first book, ‘The Female Woman’, had been a surprise success. Instead of accepting any one of the book contracts I had been offered to write on women again, I decided to tackle a subject I’d been preoccupied with through college (and indeed remain preoccupied with today): the role of leaders in shaping our world.

“I locked myself in my London flat and worked around the clock on this book. I would write until I couldn’t stay awake — sometimes into the early hours of the morning. The book was finally finished, and I don’t remember ever before or since having been as happy with the work I’d done. So imagine my surprise when publisher after publisher rejected it. Indeed, 36 publishers turned it down before it was finally published. It was the kind of rejection that brought up all kinds of self-doubt, including fears that I was not only on the wrong career path, but was going to go broke in the process.

“My desire to write turned out to be stronger than my fear of poverty. Had I been afraid, I might have tossed the manuscript in the wastebasket somewhere around rejection letter 15 and taken a job that had nothing to do with my passions. Instead, I walked into Barclay’s Bank in St. James Square in London and met with a banker named Ian Bell. With nothing more to offer than a lot of Greek chutzpah, I asked him for loan. And with a lot of unfounded trust, he gave it to me.”

Greatest Lesson Learned

“The biggest lesson I’ve learned is also the central theme of (’On Becoming Fearless’), which is that fearlessness is not the absence of fear — but the mastery of fear. It’s getting to the point where our fears do not stop us from daring to think new thoughts, try new things, take risks, fail, and start again.”

Three Best Business Lessons from Mom

“My mother… taught me three great lessons that I’ve been able to apply to every aspect of my life - particularly business. First, she showed me that there is always a way around a problem - you’ve just got to find it. She also taught me to accept failure as part and parcel of any entrepreneurial life. It’s not the opposite of success. It’s an integral part of success.

“Finally, she showed me the value of having a support group of family and friends - what I call your ‘fearlessness tribe’ - in place any time you launch anything. They are there to give you honest feedback, to support you when the going gets tough, to help salve your wounds and, just as importantly, to help you celebrate and appreciate the good times too.”

Words of Advice

“True fearlessness in business can only come when we are not driven by an insatiable desire for security, but have begun living a life driven by passion and purpose. It also helps to build a better mousetrap.”

Recommended Reading

“I think a great book for entrepreneurs to read is Malcolm Gladwell’s ‘The Tipping Point,’which is a brilliant analysis of how change comes about - and how it can be applied to business.”

Favorite Blogs

“I read many, many blogs, including (in alphabetical order so as not to play favorites among my favorites) Altercation, Americablog, Andrew Sullivan, Bloggingheads, BuzzMachine, Crooks and Liars, Eschaton, Firedoglake, Hullabaloo, Informed Comment, James Wolcott, Kausfiles, Taegan Goddard’s Political Wire, TalkLeft, and Talking Points Memo — to name but a few!”

Favorite Ways to De-Stress

“Yoga, hiking, and lots of sleep.”

Favorite Places to Shop

“With my daughters in little shops on Montana or at Brentwood Gardens in West L.A., and in SoHo where our HuffPost offices are.”

Favorite Getaway

“Staying home with the phones turned off! I’m a real homebody and I travel so much that staying in is my idea of pure heaven.”

Recent Discovery that Delighted Her

“I really enjoyed ‘Shut Up & Sing,’ the new documentary about the Dixie Chicks, and what they went through after criticizing George Bush on the eve of the invasion of Iraq. You want fearless? How about going on stage and performing in front of 20,000 people after being told that someone in the audience might want to shoot you.”