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Barbara Corcoran Talks Shark Tank, Choosing Entrepreneurs Wisely, When to Quit, and the Self-Reinvention Myth

The entrepreneur on finding her way and her purpose.


In 1789, Benjamin Franklin wrote that two things in life are certain: Death and taxes. But what about examining some of life’s fundamental pillars that we can learn to chisel into sturdy traits so that we can flourish before death and in between the taxes?

If you find that fear of failure lurks at your heels, or you’re at the intersection of ‘what’s my purpose?’ and ‘when should I quit or keep pushing?’, you’re not alone. During a candid meeting with ABC’s Shark Tank’s, Barbara Corcoran, she served a hefty scoop of entrepreneurial advice, a dollop of confidence and a squeeze of humility sprinkled with some self-deprecation.

In 2001, the real estate titan-turned-investor sat in a coffee shop contemplating the ATM receipt in her hand taken from the machine only minutes before, that read an account balance ending in double-digits followed by six zeroes. Despite the lineup of obstacle courses through the decades (including a series of contentious meetings with one of New York’s prominent figures, Donald Trump), Corcoran successfully passed the Corcoran Group torch, and though she basked in the satisfaction of the accomplishment, she didn’t anticipate the greatest challenge ahead — feeling helplessly lost.

“I had no idea what I was going to do with my career after that,” she explains. “I thought about what it would mean to reinvent myself but soon realized I had to change my attitude about it. You can’t reinvent yourself,” she asserts. “You are who you are and that doesn’t change much, but you can repackage yourself and build around whatever assets you have.” She adds, “I had to get the monkey off my back that I had to be just as successful as before — I had to get over that pressure that I had to be someone else now, and once I did that, which took a little doing, I was able to say, ‘Ok, what am I good at? What am I bad at? What do I love about all of the jobs I’ve had?’”

Leaning forward, her head playfully turned and with a wink, Corcoran says, “I came down to a narrow description of myself. I knew I was needy and wanted an adoring crowd. I was honest about that.”


When the brainstorming dust had settled, the entrepreneur’s ‘gifts’ (including marketing and interior design) were boiled down to three types of businesses: Advertising, PR and TV, which ultimately led to NBC’s TODAY Show knocking on her door to be their real estate expert.

Reflecting on her own labyrinthine career path, the friendly ‘shark’ knew that quitting wasn’t an option even during some of the most trying times. “I needed to push until I really knew I had tried everything, until the cupboard was empty,” she says, “So that I don’t have any regrets a couple of months later.” But she advises today’s startup crusaders differently. “I think a lot of them hold on far longer than they should and they should quit sooner. It takes more courage to quit than to hang in.” She adds, “It’s underestimated how difficult it is to tell your friends, family and investors that it’s not working, and the words ‘pivot’ and ‘fail faster’ are used so often they’re almost trivialized, but a good barometer is, do other people believe in you?”

Fear of failure is the universal, debilitating critter that gnaws at us all. Perhaps its roots are primitive in nature, a survival mechanism of sorts or a shield for the ego to minimize suffering (perceived or real). Or, it could be a figment companion of our minds that serves very little purpose than to inhibit us from taking the critical steps that propel us forward. Google will even produce over fifty-three million search results on the topic for anyone in pursuit of extinguishing the venomous burden. Fortunately, Corcoran learned about the faces of fearing failure early on.

“I was asked to give a speech at Citibank. There were thousands of people there,” she explains, vividly. “I had practiced all week for it and knew what I was going to say, cold. But once I stood up there on stage, my voice was gone. I couldn’t say anything and I felt sure that the next morning everyone on New York’s streets would know about my speech that didn’t happen and I wanted to crawl into a hole and never come out again.” She adds, “But not one person for the rest of my whole life has ever said that they were in that room when I gave the speech and if they were, they didn’t care. Nobody cares about your failures and that was really freeing for me,” she emphasizes with an exhale and conviction. “It made me eager to try more things, flop more often and not really think about the after effect. It was about getting over myself, not the world anymore.”

When Corcoran swam into the Shark Tank with the likes of Mark Cuban, Daymond John and Kevin O’Leary, she had earned a coveted spot on a hit show — her dream job — that didn’t come easily, but once the show was underway she second guessed her decision. “I didn’t like being on Shark Tank at first,” she admits. “I didn’t think I had the business acumen for it until I realized that choosing the right businesses had nothing to do with it. It was actually the same as what I did well my whole life which was choosing sales people,” she explains. “Did I like them? Trust them? Think they would hit the finish line and be competitive and aggressive? Once I eliminated the need to understand the business, I was as smart as the next guy and I started relaxing and enjoying the show.” And through observation of the entrepreneurs she invests in, she has also noticed a seismic shift in the direction of the future of work as we know it.

“Today there’s a tremendous pressure on people to be entrepreneurs,” she says, largely due to the landscape of a dynamic global economy. “I find that most people though, will not be able to generate the same self-confidence when you take them out of the team setting and put them on their own but that’s changing. I find that men can’t self-start as easily as women and that when I think back on the women managers I’ve hired over the years, the women weren’t claiming success until they were at the top of the mountain where the men were claiming it when they were halfway up.”

One of ten children vying for the attention of two parents (all siblings are highly creative and in business for themselves except for one), Corcoran managed to galvanize the adoring audience she had forever craved, and in droves. The media cyclone hasn’t been able to sweep her far from the ground though; in fact, her feet are firmly planted close to where they began sixty-eight years ago in Edgewater, NJ.

“In the end I wound up pretty much like my mother,” she says with a sense of relief. “We’ve all mimicked our parents. We’re all hard working, self-motivated and very competitive. We all became a product of what we saw at home. Kids wind up becoming exactly what they see,” says the mother of two (at ages forty-six and fifty-six). She continues, “It’s the joy of being part of getting there, the journey, and that’s where all of the joy was at the Corcoran Group. It wasn’t the $68mil I put in my bank, although I have to say I didn’t mind having it — it was everything that I experienced with those people through the years to make the magic happen.”

There’s one common, critical thread that Corcoran looks for in the entrepreneurs she partners with, as well as colleagues and lifelong friends: Resilience. “The sad people in life who take the hits will become victimized and the happy people in life who take the same hits pick themselves up; they don’t feel sorry for themselves for long and they keep going,” she says. “If you can surround yourself with people like that around every bend, you’ve got like ‘happy wallpaper.’”

Originally published at medium.com

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