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 futile 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.