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Barbara Corcoran on the Power of Failing Well

From overcoming a fear of public speaking to almost losing out on a breakthrough role, this entrepreneurial icon shares the upside to her experiences with failure.
March 24, 2015

I suspect just about everybody struggles with public speaking, but when I lost my voice during my first-ever invitation to speak, I was mortified. I had spent weeks preparing and knew I would knock it out of the park. But when I gazed at the faces of the 300 serious bankers staring back from their seats, I plum lost my voice. I still remember those fated words after the silence that lasted an eternity ... “Thank you, Mrs. Corcoran, you may have a seat.” I made up my mind right then and there that I would never, ever speak in public again.

By the time I got home, I knew I had two choices: I could stay in my rabbit hole and be ashamed forever, or I could learn to speak in public. The next morning I marched my butt over to the local university to propose my new evening course “How to Sell Real Estate”—the one thing I really knew how to do. I figured if I could get myself talking in front of a group of students every week, it would be my best shot at getting good.

That turned out to be a lucky decision. Not only did my 10-week course make me more comfortable talking in front of people, but one of my 11 students was a woman who became the No. 1 real estate salesperson in all of New York for the next 25 years.

The Upside of Failure

Everything great in my life always happened on the heels of failure. When I threw away my very first profit on a newfangled idea to put all of our apartments for sale on VHS, I watched that amazing idea turn into a very expensive flop. But instead of licking my wounds, I decided to throw the same videos on this newfangled thing called the “Internet,” and within two days, two buyers from London found their New York City apartments on

When my boyfriend and business partner announced he was going to marry my secretary, I was devastated. After all, he had found me at the diner, told me to quit my job as a waitress, took me out of my small town in New Jersey and even loaned me the $1,000 to start my little apartment renting business. I knew without him I would be nothing, and spent a day in bed before pulling myself together and hoofing back into the office to warmly congratulate the happy couple on their upcoming marriage. One year later, I finally mustered the confidence to end the business and start my own business, The Corcoran Group, which would later sell for $66 million.

A Shark Tale

Today I’m a Shark on ABC’s Shark Tank. When I first got a call from an L.A. producer asking if I’d have any interest in being on the new show, I couldn’t believe my good luck. I was headed to Hollywood! I signed the contract immediately and ran out and bought myself two new swanky outfits at Bergdorf Goodman, just for signing autographs. But a few days before leaving, the producer’s assistant called to say they had changed their mind and had given the lone female seat to someone else.

Ten minutes later, instead of getting sad, I got mad, and shot the producer an email. I told him I considered his rejection a lucky charm because everything good that ever happened to me happened on the heels of failure. I ticked off a list of all my triumphant rejections. I ended the email by suggesting the producer fly me out to compete with the other woman for the spot. It was my stand-up-and-be-counted-for email that got me on that plane, and I’ve been a Shark/Investor on Shark Tank ever since.

I know the importance of taking a hit and getting back up. I’ve never met a successful entrepreneur who wasn’t good at it, too. Failing well is far more important than a good sales pitch, the fancy degree or the right funding. Almost every successful business is built on a long string of failures that the entrepreneur has managed to overcome.

Read more articles by Barbara Corcoran.

 Photo: Getty Images