What is the key to a healthy marriage?

Communication? Laughter? Therapy?

If you ask Barbara Corcoran, the real estate entrepreneur who founded the Corcoran Group in 1973 with a $1,000 loan and sold it in 2001 for a reported $66 million, it is an extra apartment.

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In the summer of 2008, a jubilant Barbara Corcoran boarded a plane to Los Angeles, her heart thudding with excitement. Seven years earlier, she’d sold her stunningly successful real estate company, the Corcoran Group, for $66 million, and since then had struggled to build a television career from scratch, with intermittent gigs on The TODAY Show and Fox News. Now she seemed on the verge of landing a game-changing job: Survivor producer Mark Burnett had called her about a high-stakes reality show called Shark Tank, in which five tough business titans meet with aspiring entrepreneurs to consider investing in their companies. Would Corcoran care to audition for one of the titan spots? “I thought, This is what I’ve been dreaming about,” Corcoran says. “The big kahuna! I love to help people, and I’d love to buy businesses.”

Known in New York as the female Donald Trump, Corcoran came from a background far less privileged. The daughter of a printing press manager and a homemaker, she’d grown up in a modest home in Edgewater, New Jersey, sharing one bathroom with nine siblings. Brash, funny and entirely self-made (she’d held 20 jobs by the time she was 23), she thrived on power while never losing her blue-collar roots. On that flight to L.A., the seasoned entrepreneur gave way to a giddy, starstruck kid. “I felt like such a big shot,” she says. Corcoran arrived to find that she would be the only woman among five panelists on the show. They taped a pilot to present to the networks; contract negotiations commenced. When she returned to New York, however, Burnett’s office called and said, “Sorry, we’ve picked another woman.”

Corcoran couldn’t believe she’d been jilted. After starting her real estate business with a $1,000 loan from a cheating boyfriend in 1973, she’d transformed it into a behemoth with 700 agents, $2 billion in annual sales, and a client roster that included Jerry Seinfeld and Richard Gere. Her smiling face had beamed down from Corcoran Group ads plastered on billboards all over town. Her motto as the boss was “Happy people work better,” and the firm’s eye-popping perks included massages, manicures and yoga classes. One of her legendary company parties featured a hot air balloon; another, 10 gleaming Thoroughbred horses in full gear for staffers to ride.

But by 2001, her priorities had shifted. Corcoran wanted to spend more time with her seven-year-old son, Tommy. She and her husband, former FBI agent Bill Higgins, had gone through a lot to get Tommy in the first place; they’d weathered almost seven years of fertility treatments until Corcoran’s younger sister, Florence, volunteered to donate her eggs. Now, dropping off her son at school in the mornings, Corcoran felt distracted by the urge to be at her desk at 7:30 sharp. “I constantly had this tension between my top salespeople, who were very needy, and my child,” she says. When a rival firm offered to merge, she quickly decided to sell the company outright, buoyed by the thought of walking Tommy to school every day, “holding his chubby little hand,” Corcoran says. “I ran for that carrot — before it was too late.”

She sold the business to the real estate conglomerate NRT and signed the papers on September 7, 2001, just before the New York housing crash that followed the terrorist attacks. The huge sale should have been a sweet triumph for Corcoran. “The whole world said, ‘You’re amazing, rags to riches, blah blah blah,’” she recalls. But afterward, despite the joy she got from her walks with Tommy, she felt as if her identity had been utterly wiped out. “Oh my God,” she says, “I was so distraught.”

Although she remained chairman of the board, she allowed the new president to take over all the high-profile functions she’d previously fulfilled herself — like giving speeches. “Without being able to display that kind of power, I felt empty,” she says. One day she walked into the company’s office and noticed a familiar face smiling out from one of the trash bins: her own. Someone had thrown away the poster of her that had always hung in the reception area. She got the symbolism.

But she’d always been resilient. As part of a large family, she quickly learned that to grab attention, she had to speak up, manipulate, charm and negotiate. She was a D student in school (and didn’t find out until she was in her fifties that she had dyslexia). Classes were awful, she says, but because she couldn’t focus on the lessons, her imagination had free rein. “Do you know what an advantage it is to be a dunce?” she says. “You’re a daydreamer par excellence!”

After selling the Corcoran Group, she jumped into writing a funny, juicy memoir titled If You Don’t Have Big Breasts, Put Ribbons on Your Pigtails, & Other Lessons I Learned fom My Mom. “That killed a lot of time,” Corcoran says with a little laugh. “But I was working around a deep sadness, and once the book was done I thought, Now what?” She reeled from one scheme to the next: A school for dyslexics? Renovating apartments to flip? She just couldn’t muster the passion to get anything off the ground. Within a year of selling her real estate empire, the woman who once coolly faced down Donald Trump in court to collect the unpaid half of a $4 million commission (and won) was as insecure as a teenager. “I felt sure I had lost my touch,” she says, “and that the Corcoran Group was just a fluke.”

But it wasn’t in her nature to brood. Instead, she puzzled out her talents. She had the gift of gab, liked to give advice and had always been a lively, informed guest on talk shows. Shy couldn’t she be a television personality? With renewed energy, she phoned every network head she could think of. Recognizing her name, they returned her calls with gratifying speed and agreed to meetings. “I thought, Whoa, this isn’t bad — I’ve got some power here,” she says. She carefully prepared to wow them. Tapes of past interviews: check! Artfully crafted pitch letters: done! Selling was something she knew how to do. But each visit went the same way: An executive would listen to her spiel, then say, This looks really interesting, let me talk to my producers. “Then they’d say, ‘Listen, let me ask you a personal real estate question,’” recalls Corcoran. “Then they’d never return my call again.” Her confidence plummeted. She’d change her outfit 15 times before she left her apartment, and dreaded running into former colleagues who would brightly ask what she was up to. Her millions provided scant comfort.

Burying her anxiety, she kept plugging away at the networks. In 2004, Fox News interviewed her about real estate legislation and soon afterward offered her a regular slot as a political commentator. There was only one problem. “I’d never read a newspaper in my life,” Corcoran says. “I didn’t even know which Bush was in office. It was an effin’ joke, if I may say!” She and Bill were considering adopting a baby, but there was no way Corcoran was going to turn down the offer. “I didn’t sleep at night. I would memorize how to say names. It was horrific. I was faking this personality, but that was the only job I could get.” After she gained on-air experience (with intermittent stints on Good Morning America chatting about real estate), she contacted the TODAY Show, armed with DVDs of her work. In 2007 she accepted a job as the show’s weekly real estate contributor — a gig she’s had ever since. And a year later, she published a nonfiction book about real estate, Nextville: Amazing Places to Live the Rest of Your Life.

Burnett’s audition offer — and subsequent rejection — came in 2008. Fired up, Corcoran banged out an e-mail response to Burnett, hit SEND and also had it hand-delivered to him. “What I learned in real estate sales helped me in the TV world,” she says. “Perseverance, breaking through rejection and going back for another swing at the ball as quickly as you can.” Her letter read, in part:

Although I appreciate being reserved as a fall-back, I’m much more accustomed to coming in first. I think you should consider inviting both of us [Corcoran and her rival] to LA for your tryouts. I do my best when my back’s against the wall. I’ve had all my big successes on the heels of rejection and frankly, it’s right up my alley. There was Sister Stella Marie in 5th grade who said I’d always be stupid because I couldn’t read. Then there was the New York old boy network trying to lock me out of their real estate fortunes, until I became their largest competitor. Then there was The Donald himself who wrongly swore in court I’d never see a penny of the $4m commission he owed me for saving his ass and making the largest land deal in the city’s history. And of course there was my ex-partner Ramone Simone who parted with the words, “You know you’ll never succeed without me!” I consider your rejection a lucky charm.

She closed her letter by ballsily informing Burnett that she’d already booked her flight to LA. Three weeks later, she was back in his office.

The turbo-motivated Corcoran won the job. Later she discovered that Burnett had rejected 40 wealthy, powerful people. “But none of them came back fighting!” Corcoran says. “It’s a great lesson.” Shark Tank had a successful first season, and although it was not renewed for the fall [since the original date of publication Shark Tank has been picked up for eight additional episodes!], Corcoran has gotten her groove back. At 61, she says she has “huge energy — I’m eager, I’m excitable, I work hard.” She continues to dish on the real estate scene on the TODAY Show, where her fizzy demeanor — flirting with the cameraman, joking with Al Roker — has won her many fans. She’s “shepherding to success” the eight Shark Tank businesses she bought and is feverishly pitching new shows to the networks.

“Now I truly feel like I’m on my new adventure. The minute I can do anything well, I’m thinking, OK, I got that down. Now what else can I do?” Corcoran says, laughing. “And the only way I’m going to find out is to keep throwing the crap up there and see what sticks.”

– Jancee Dunn

Barbara Corcoran and others answer the question “What’s the worst money advice you ever received?”

Travel Essential:
I never travel anywhere without my trusty Ferragamo fringed double-cashmere cape. I have two, one in charcoal gray and another in toasty brown, and they go with everything. I paid far too much for them, but they’re worth their weight in gold!

Travel Uniform:
I always pack two white Hanro stretch T-shirts. They always feel comfortable, look fresh and seem to brighten my face and even whiten my teeth! I also always pack two pairs of Cambio Celia jeans. They look good with everything and are made with Lycra, so they wear well for days.

The Bag:
I carry Bric’s faux cowhide carry-on with wheels. They fake cowhide looks and feels more luxurious than the real deal, and it never gets dirty. The bag fits perfectly in the overhead compartment. Its adjustable handle never jams, the hidden wheels roll quietly and, should something spill inside the bag, the lining zips out and can be thrown into the washer.

Sounds of Silence:
I can’t imagine even a short plane ride without my Bose noise-canceling-headset.

In-Flight Entertainment:
I always pack a travel-sized Scrabble game. It’s helped me make friends all over the world. It’s easy to start a conversation with “Do you play Scrabble?”

Delta Sky Magazine, August 2010