Barbara Corcoran Loves to Fail

Why she’d prefer a chip on the shoulder to a degree any day.
Barbara Corcoran Loves to Fail
Barbara Corcoran Loves to Fail

Barbara Corcoran likes to tell people that she got straight D’s in high school. It's a line in nearly every profile written about her—that and the fact that she had 20 jobs by the time she was 23. She mentions it not just because it’s part of her incredible story of coming from nothing and making herself into one of the most famous real estate icons in the country, but also because it’s the hallmark of a quality that has made her such a huge success: her ability to embrace failure. So much so that she’s called it her sweet spot, even saying, “Failure is what I’m best at.” Every time she’s encountered it, it’s only served to light a fire in Corcoran to push on to achieve better things.

That sort of mindset isn’t unique in the entrepreneurial world. The ability to “fail fast” and grow as a result of it—the importance of grit and overcoming obstacles—have become part of Silicon Valley gospel, preached by every start-up founder hacking away the nights to get dreams out into the real world. And that's a mental habit Corcoran has, too. In her words, “You don’t have to get it right, you just have to get it going.”

Determined to Take Charge

But Barbara Corcoran didn’t start her journey toward becoming the icon she is today with a dream of being a huge success. For her, it was just about the desire to not have a boss anymore. In those 20 jobs by the time she was 23, Corcoran got sick of being told what to do and, unlike most, she was willing to take her destiny in her own hands and get moving instead of worrying about getting it right. 

Along the way, Corcoran faced many challenges. People who thought she couldn't do it—said she wasn't smart enough or didn't have what it took. Which is maybe the other reason why she likes telling the story about making D’s in high school. It's a symbol of what's well-known among many of the self-made—that being the smartest or the best matters far less than the willingness to dig in, work hard, and believe even when everything’s going wrong.

Every single failure has an equally great upside if you are willing to stay in the game.-Barbara Corcoran

A Struggle From the Start

Before she was a star on Shark Tank; before her real estate business was worth billions  or she had even started the business at all, Barbara Corcoran was a girl born in Edgewater, New Jersey. She grew up as the second of 10 children in a crowded household where money was tight. Her mother’s energy and commitment to managing her chaotic household inspired Corcoran, but she also found a way to learn from her father's less-than-positive contributions. 

Corcoran's dad had trouble keeping a job throughout her childhood. H
e would come home and complain about whatever boss and whatever short-term gig he had, and that was the first time it crossed Corcoran's mind to never want to have a boss of her own. The two of them were similar in other ways; he was known as the fun dad in the neighborhood, and she was the sibling in charge of making fun for her four brothers and five sisters. But no amount of fun could keep the financial struggle from wearing on the family. At times, food was even hard to come by. The meals the family ate were only thanks to the generosity of a grocer who delivered food to them for free until they could pay for it.

That sort of poverty as a child is something that Corcoran sees as a positive now, saying that it’s actually harder for people to succeed when they’re educated and wealthy than when they start off poor. As she told Inc in an interview with Kris Frieswick, “Poor kids have nothing to lose and nowhere to go but up. They have no parental pressure to be a somebody when they grow up. They don't have to succeed, but they have in spades the wonderful trait of being needy. They need to succeed. That's the magic bottom-line juice I'm looking for, and it's very hard to have that innately if you've grown up with privilege and a high degree of education. It truthfully is. You're better off being poor."


Learning to Beat the Boys

Her father's joblessness wasn't the only negative that Corcoran turned into a positive. Her father had a tendency to drink too much, and Corcoran never knew which father, the fun one, or the mean one, would come home. Seeing him talk down to her mother became a crucial lesson for Corcoran that prepared her for when she entered the boy's club of real estate, where she made an early commitment to never letting anyone talk to her the way her father had talked to her mother.

The minute a man talked down to me, I was my best self. I was going to get from that person what I wanted, come hell or high water. Even by the time I got it, sometimes I didn't want it anymore, but I grabbed it because I had to show him that he was not smarter than me. He was not going to dismiss me. I would not tolerate it. I would say quietly to myself, 'Fuck you.'-Barbara Corcoran

Ironically, it was an older man who gave her the break that would turn her toward success, and then threaten to end it all. His name was Ramone Simone, and Corcoran met him during her time as a waitress at a diner in New Jersey. He walked in with an air of luxury, wearing navy blue aviator shades and a suit with a pressed collar. The minute Corcoran slid into the leather seats of his Lincoln Continental for a ride home, she was hooked. They quickly fell in love, and she moved in with him in New York and began her real estate career.


The Apartment that Started it All

Corcoran was working as a receptionist for real estate holders, the Gifuni brothers, when Ramone suggested she had the personality for real estate sales, and encouraged her to give it a try. With 20 jobs already under her belt, Corcoran decided to do it, and took a $1,000 loan from Simone to create a company where he owned 51 percent. Then she went to her boss to ask for an apartment to list.

He gave her the worst one imaginable. It was in the back of the building and tiny, but Corcoran once again saw the possibility in the hardship. She convinced the owner to put up a half wall in the middle of the apartment so she could list it as a "one-bedroom with den" for the same price as regular one-bedrooms. It got snapped up, and she was off to the races.

Things started to take off. She made enough to rent a desk, then employees, then an office, and started building her real estate empire apartment by apartment. Then, in
 1980, Simone dropped a bomb on her—he was leaving her to marry his secretary. Not only was it the end of their relationship, but it was the end of her company as well, since he owned 51 percent. She still remembers what he said on his way out the door. "You'll never succeed without me."

But he didn't know that Corcoran would take failure in stride quite the way she did. In response to Simone’s betrayal, she started her own business and got right back to building her empire—this time with a chip on her shoulder to prove him wrong.

And she did it. In 2001, Corcoran sold the real estate company she built after Simone said she'd never succeed for a cool $66 million—a number she picked just because she thought it sounded good. It was one of the largest monetary examples of turning failure into success in her story, but it wouldn't be the last. 


Scoring a Second Act

In 2008, Corcoran was contacted about an opportunity to be on the show that has now made her more famous and successful than ever—Shark Tank. She was so thrilled at the offer she returned a signed contract without even reading it first. But then the show called. They told her they’d changed their minds and hired another woman at the last minute. 

Rather than give up, Corcoran once again used failure as fuel. She dashed off an email to the studio owner, Mark Burnett, telling him what had been true her entire life: that she did the best when her back was against the wall. She proposed something not even on the table—that the studio bring both women in for try outs—and made Burnett’s assistant promise to print it out and give it to him.

It made all the difference in the world. Her letter and her story about overcoming failure convinced Burnett to give her another chance. She tried out and got the job on the show, and for the last 12 years has been finding even more success as she invests and mentors other businesses.

Corcoran says  she knows which entrepreneurs are a good bet, because they have so many of the same qualities that she does—they're independent and hard working. But above all, she loves the ones who come from nothing, and have learned to turn hardship into an asset. Because after seeing where it's taken her over her life, she knows they'll be a success. 

A bad childhood? Yes! I love it like an insurance policy. An abusive father? Fabulous! Never had a father? Better! My most successful entrepreneurs didn't all have miserable childhoods, but somebody said they couldn't, and they are still pissed.-Barbara Corcoran