Barbara Corcoran Shares One of Her Greatest Lessons in Trusting Her Gut

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If you’ve ever seen Barbara Corcoran on “Shark Tank,” listened to her give an interview or read one of her books, you likely imagine that she’s always had the same confidence that inspires millions. But even highly successful people have their moments of doubt, and Corcoran is no stranger to the highs and lows of the business world — including learning how to honor her own intuition. 

The real estate maven sat down with Angela Yee, host of the radio show “Way Up” with Angela Yee, to talk about the current state of the market, the new season of “Shark Tank” (of course), and the one time that trusting her gut ended up earning her millions of dollars

The $66 Million Sale That Almost Wasn’t 

In her conversation with Yee, Corcoran shared a little-known fact about the famed sale of her real estate brokerage, The Corcoran Group. While she ultimately sold the business for that whopping sum, five years earlier, she was in a much different position. Anxious about the state of her business, Corcoran was initially relieved when Merrill Lynch offered her $100,000 for it. 

For Corcoran, who’d grown up in a family that occasionally relied on free meals from a friendly grocer, being her own boss and supporting herself was a major priority. She started as a waitress and later began selling apartments in NYC. A $1,000 loan from her boyfriend gave her the foundation to launch a real estate business with him. Years later, after he informed her that he’d be marrying her secretary, Corcoran dusted herself off and started her own firm, The Corcoran Group. 

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When Merrill Lynch approached with a six-figure offer for her business, Corcoran was initially tempted to take it. “That was when I was desperate for cash. I couldn’t believe my good fortune to have Merrill Lynch wanting my business for $100,000,” she told Yee. With the hindsight of her game-changing sale behind her, she reflected that it was “a shame” she ever considered the offer. 

What made her turn it down? Her gut instinct, she said. 

Trusting That She Could Do Better 

Deep down, Corcoran always had a hunch — or at least a desire — to sell her company for $66 million, in no small part because 66 is her lucky number. She had to ask herself: Was she truly desperate enough to settle for so much less? She told herself she wanted to try one more thing. 

“And in trying one more thing, you always find an answer. Everybody finds an answer just trying, trying, trying,” she said. 

Corcoran also had a sense that she needed to avoid what she called “the Cinderella syndrome” — the idea of hoping a random Prince Charming would come in and rescue her with a deal that wasn’t ultimately satisfying. Prince Charming, she noted, doesn’t just want to hand over the keys to his kingdom; he also wants a big say in how it’s run. 

As someone who prioritized being her own boss, Corcoran realized she had to pass on what seemed like a terrific offer. 

Learning the Value of Negotiation

Walking away from that offer empowered Corcoran to ensure that when she did sell her business, she wasn’t just hitting her lucky number — she was getting her worth. Initially, the firm that purchased The Corcoran Group offered her $22 million. But Corcoran had already decided $66 million was the magic number she would accept. 

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As a negotiation tactic, she rejected the $22 million offer. The very next day, the buyer called back with the right number, down to the penny. If she hadn’t trusted her instinct years earlier, Corcoran might never have been in the position to earn millions or launch the career that has inspired countless people.   

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