Shark Tank's Barbara Corcoran Says Ex-Boyfriend Left Her For 'Younger And Prettier' Secretary After Giving Her $1,000 To Start A Business

Barbara Corcoran's rise to business stardom didn't come without a few dramatic twists, including a memorable breakup that became a cornerstone of her success story. The self-proclaimed "Queen of New York Real Estate" often shares the tale of how her ex-boyfriend, Ramone Simone, left her both personally and professionally – but not before giving her $1,000 to start the business that would eventually make her a household name.

In a December 2024 conversation on the Sprouht podcast, Corcoran reflected on the pivotal moment when Simone announced he was leaving her. After seven years together, he revealed he was marrying her secretary. "I was out. She was in," Corcoran recalled. "She was younger and prettier than me." Simone had been her business partner, owning 51% of the real estate company they had built together in the early 1970s. The breakup was devastating for Corcoran, but it also became the catalyst for her success.

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This wasn't the first time Corcoran shared the story. On Steven Bartlett's The Diary of a CEO podcast in 2022, she recounted how Simone's decision to leave – and his 51% stake in the business – meant she had to start over. His parting comment at that time? "You'll never succeed without me." The words were a gut punch but also fueled Corcoran's ambitions. At the time, she says she hated him, but in hindsight, she sees the breakup as the defining moment that drove her to launch The Corcoran Group.

After parting ways with Simone, Corcoran didn't just rebuild – she soared. Her first big move was placing an ad in The New York Times to announce her new business. The ad paid off, attracting clients and establishing Corcoran as a real estate force in New York City. She even took an office two floors above Simone's in some strategic (and satisfying) positioning.

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Corcoran grew The Corcoran Group into one of the most successful real estate firms in the country. In 2001, she sold the company for $66 million, cementing her status as a self-made business mogul. Looking back, she now says, "Thank God," for Simone's departure, recognizing it as the moment that allowed her to claim independence and drive her to greater heights.

From heartbreak to boardrooms, Corcoran's story is a master class in resilience and reinvention. What started as a $1,000 loan became a billion-dollar empire – and the ultimate revenge against anyone who doubted her.

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