Sharp Barbs

The very rich love to talk about their bootstraps. They all seem to have made great use of them, pulling on them unremittingly to get to the top of the pile. Of course, a rags-to-riches route makes for better PR than a tale of a rich kid who just keeps getting richer, which, if we are honest, is nearly always what really happened.

But Barbara Corcoran, 66, is the real thing (although she prefers heels to boots). Unlike so many humble braggers who credit their individual genius for their fortunes, she’s quick to admit that her extraordinary achievements required lots of lucky breaks, mixed with a little tenacity.

“Being lucky is an attitude,” she tells LLNYC from the windowed breakfast nook of her Park Avenue co-op. “I am extremely lucky. I always expect luck. But you need scrappiness to recognize a lucky break when it comes along. I think lucky breaks and being scrappy are kissing cousins.”

Outside, a sliver of Central Park is visible between two buildings, with the San Remo in the distance. She has lived here for 18 years with her husband William Higgins and her two children, but will soon move two blocks over to an 11-room penthouse at 1158 Fifth Avenue  —  a home she’s coveted for decades, after delivering a package to the owner and being invited inside. She paid close to $10 million for the duplex apartment and its garden terrace  —  a splashout for the notoriously frugal Corcoran. And no, she is not buying a private island, as rumor has it. Besides her new apartment, she says her biggest expenditure was a $500 painting of a farmhouse in her lounge. For our photo shoot, she wore $10 costume jewelry, insisting that she never buys the real thing.

Most of America knows her from ABC’s reality show “Shark Tank,” where eager entrepreneurs pitch ideas to Corcoran and the other “shark” investors. She has just signed on for another three seasons of the show. But many New Yorkers recognize her primarily as the namesake of the Corcoran Group, one the city’s largest real estate brokerages. She sold her firm in 2001 for roughly $66 million before getting into the television business.

“I watched New York go from a middle-class city to a city of the rich. I watched it go from predominantly New Yorkers to mostly internationals. I watched the city totally reinvent itself, and I was the beneficiary of that,” she says. “It’s terrible for the people who got pushed out. It’s terrible news for families who can’t afford to live here. But if you can afford it, it is wonderful.”

The legend goes that Corcoran grew her business into the city’s second-largest brokerage with nothing more than her wits and a $1,000 loan (roughly $5,300 in 2015 dollars) from then-boyfriend Ramon Simone (who, in an act of cliché, would eventually leave her for a junior member of the firm). “I knew I was going to lose my virginity the second I saw him,” she laughs. “Women know these things.”

But it’s worth deconstructing this bootstrap myth. It’s to Corcoran’s credit.

Interior of Corcoran’s co-op on Park Avenue

“How do you grow a business out of $1,000? An inch at a time; no big leaps,” she says. Corcoran comes from a family of 12: 10 children and two parents in a one-bathroom house. “My dad was my mother’s 11th child. All he cared about was fun,” she says. They were poor and Corcoran says she always understood that she would need to provide for herself completely. Before she tried her hand at real estate, she had already floated between different 22 jobs.

She was a waitress four times; a hot-dog saleswoman along a highway; an over-the-phone tent saleswoman (“You would be surprised how many people need to rent a tent.”); a receptionist, twice; a secretary, four times; a stenographer (“I got fired, but it counts.”); a life guard; a “house mother” at an orphanage (“That was one of my best jobs. I got paid double time to sleep.”); a playground guard; a “home teacher;” a sales clerk at a department store; a bookstore clerk; a tour guide at an historic Greek diner; a florist and a babysitter. Getting into real estate seems to have been more or less an accident — or a stroke of good luck.

Before launching her own business, Corcoran worked as a receptionist at a small, family-owned real estate firm. After a year, they gave her their worst listing to market. It was a dark L-shaped one-bedroom on the corner of 83rd Street and First Avenue, asking $340 a month. “It sounds absurd now, but that was a good-sized rent in a doorman building,” Corcoran says. “I thought, ‘How the hell am I going to rent this thing? I didn’t want to seem ungrateful.’”

It was 1973, and the New York Times and the Village Voice had a near-monopoly on real estate classifieds. Corcoran placed three-line ads for the apartment. “It was like fishing back then,” she says. “If you wrote a good ad, you got a call.” 

She noticed a glut of ads for one-bedrooms priced similarly to her own listing. So she went back to the owner with an idea. “I said, ‘I think I can get you $380 a month if you’ll build me a half-wall in the L of the living room.’ ” Her new ad read: “1BR PLUS DEN $380 A MONTH.”

“My phone never stopped ringing. Who wants a one-bedroom, when they can get a bedroom and a den?” Corcoran recalls. “It worked like a dream.” The family hired her to market the rest of the building, and she was able to slowly hire agents. By the end of the year, she had a four-person team.

“You sure as heck need lucky breaks,” Corcoran says. “Imagine if I wasn’t working for that family? Imagine if he hadn’t put up that wall?”

In 1978, Corcoran formed the Corcoran Group, and luck was with her again as many of the city’s rentals were being converted into more exclusive co-op apartments, which offered much higher sales commissions. Three years later she launched the highly successful and first-of-its-kind Corcoran Report on the health of the residential market, despite having only 11 sales to base her report on. In the following decades, her roster snowballed into a battalion of just under a thousand agents, making billions of dollars worth of deals every year.

Corcoran admits that she had one advantage starting out: She credits her oversized, hyperactive family with giving her social skills others are forced to learn later in life.

“If you grow up in a house with a lot of kids, you have a tremendous head start,” she says, adding that her mother’s endless energy and work ethic was particularly inspiring. “We were all grown up before we were grown-up.”

“I watched the city totally reinvent itself, and I was the beneficiary.”

She recalls her mother cooking three meals for 12 people at their home in Edgewater, New Jersey, doing eight loads of laundry, ironing all of the children’s clothes and polishing all of their shoes each day. “We wore the same thing everyday, but we were the best-dressed kids in town.” After the kids went to sleep, she would clean the home. “We always woke up to a clean house and breakfast on the table,” she says. “My mother was a dynamo.”

Corcoran says her home was run like a boot camp, but that it taught her self-reliance, flexibility, cooperation and how to get attention.

“More than anything, you learn to get along with people. If you can do that, you have half of life licked. We had no kings or queens in our family. There was no room for it.”

Her upbringing also helps explain her leap into television, which was hardly an obvious move for her at the time. After selling the Corcoran Group, she had intended to retire and spend more time lunching with friends, cooking pasta and being with her son Tommy, now 21, and daughter, Kate, who she subsequently adopted and is now 10. But it wasn’t that easy.

“I was totally lost. I was fighting depression. I lost my children; I had a thousand kids,” she says, referring to the brokers she once managed. Her festive managerial style had created an intimate culture that she missed.

“The theme parties were my favorite part of the job,” she recalls. “The best one was my transvestite party. You had to cross-dress to get in, and the straight men all signed a petition saying they wouldn’t come  —  I didn’t have that many straight men working for me, most were gay. But I didn’t pay attention because I knew they would come. They came and had a ball. It was such a thrill to have 1,000 people all cross-dressed. And I think the straight men had the most fun. It gave them the opportunity to be something they weren’t.”

Corcoran says that she prefers the company of gay to straight men. “It isn’t that sex is dangerous, it’s boring,” she says.

Corcoran was notorious for mothering her agents, admitting that she needs to be worshiped by those around her. In her offices, she handed out yellow ribbons and cotton candy, hired yogis, masseuses and elephant-drawn carriages (at a countryside event), and threw increasingly extravagant parties. Even after selling her firm, she’s been known to spruce up the flowers in the office window boxes.

“I felt like I didn’t belong to anything, it was so sad,” she says of her departure.

She considered starting other businesses, first in public relations and then in advertising. But she wanted a job with independence. And after being invited onto Neil Cavuto’s show on Fox News as a real estate commentator, she realized she found her new calling.

“I need attention. I missed my brokers, and I needed something to belong to,” she says, with her television stylist at her side. “I love an audience, and I love people who adore me.”

She asked Cavuto for a regular job on Fox, but he found her a spot, not as a real estate or business commentator, but as a political correspondent.

“I didn’t even know the difference between the Senate and the House of Representatives. It couldn’t have been a worse suggestion, but I said I’d take it because it was a ticket in,” she says. “It was a joke; all I did was study. I don’t care about politics. Not one inkling do I care about politics. I guess I should, but I really don’t.”

She was able to leverage that job into a position as a real estate commentator on “Good Morning America” and the “Today Show” during the depths of the economic recession. “That was another lucky break. Imagine if it was a buoyant real estate market. I would have never gotten that job. Bad news prints.”

Corcoran will soon move to an 11-room penthouse on Fifth Avenue.

But it was after she was approached for “Shark Tank” that she became known outside of New York. Still, she says this latest stroke of good fortune wasn’t a smooth transition.

“For the first three or four years, ‘Shark Tank’ wasn’t fun. I was afraid all the time that I would be fired. I wasn’t comfortable in my own skin,” she says. “I was labeled a shark and they dressed me in black. It was off-character for me. I’m not a tough shark. If someone asked me for a word to describe myself, I would say ‘sweetie pie’ not ‘shark.’ ”

She says that the part of the show that really clicked for her was motivating the entrepreneurs, who were so similar to the real estate brokers she had managed for years. “My assessment on the show had nothing to do with the business plan. It had to do with my judgment of their personality. And I was very accurate.”

Corcoran says she invests in people who have energy, street smarts and are nice. She won’t invest with anyone who is a “bastard.”

“I never saw anyone without a lot of energy that was hugely successful,” she says. “And a lot of the people on ‘Shark Tank’ are very well educated … people who went to the right schools, learned the right lingo and have had a life of privilege. I can’t relate to them. For them, succeeding is an option, not a need. But I want someone who is desperate and has something to prove. Basically, I want someone who is insecure.”

It’s insecurity, not business school confidence, that Corcoran, and many other successful people, relate to. For them insecurity isn’t a weakness, it’s a driving force. What better motivation is there than the knowledge that at any moment the floor might fall out from under you?

This wariness apparently carries over into Corcoran’s personal life, where it becomes fodder for a self-deprecating laugh.

“I don’t like sex. I like massages. One-way sex every time!” Corcoran jokes. “I just don’t have the confidence. Image getting undressed in front of a younger man. Even I get disgusted. I’ve been hit on by younger men, but I am sure they want my money. It can’t be my body! I wasn’t born yesterday.”