Barbara Corcoran – How this D Student Went From Waitress to Running a Billion Dollar Property Empire

By Stephanie J. Hale

Barbara Corcoran started a tiny real estate company after quitting her job as a waitress. Over the next 25 years, she turned it into a 5 billion dollar business. Barbara is also a best-selling author and appears as the sole female entrepreneur on the TV show ‘Shark Tank’.

The following conversation is an excerpt from the book “Millionaire Women, Millionaire You” by Stephanie J Hale.

Q: Barbara, you got straight D’s in high school and college. You had over 20 jobs by the time you turned 23 and you then famously borrowed $1,000 from a boyfriend and your life changed forever. Tell me exactly what happened.

I was working as a waitress and fortunately Ramóne Simóne was his name – Ramóne Simóne with an accent on the O’s or whatever he did – ordered a cup of tea at my counter, which was very lucky because he offered me a ride home. I lived one town away, which was about half a mile away from the diner. He drove me home and that was the beginning of our relationship. Ramóne was about 10 years older than me, and from a whole different world – or so he said. He said he had been raised in the Basque Country, as in Spain. He had olive skin, dark sunglasses, jet-black hair. He had a very shiny suit on and I had never seen anything like it.

So he drove me home in his very fancy yellow car, which was a Lincoln Continental, and drove me to my family’s house. We had in our family 10 children and I was the second oldest. So that night he walked in and met (I don’t think my older sister was home) but he met at least nine out of the 10 kids and they just loved him!  They thought he was like a Hollywood rock star walking into our house with the car running outside. It was like we had been found, but my parents hated him on sight. I think they saw him for who he was, 10 years older than their young daughter and Trouble!

So he proved to be trouble in their eyes, but he also proved to be the luckiest break I ever got. The trouble he caused was he encouraged me to move to New York City, and in fact he offered to pay for a week at a women’s hotel in New York that was quite respectable. You had to wait in the lobby if you were a date, you couldn’t go upstairs. I guess he thought that would make my mother happy. She was not happy. She’d forbidden me to go, but I went anyway and I never moved back to New Jersey again. One thing led to another after that. Within that year, he loaned me the $1,000 to start the real estate business. Why I started that business?  He just said I’d be great at real estate and he seemed to be a man of the world who would know that kind of thing. So I said “okay” and we started a partnership together.

So would you say he was your first mentor?

Definitely. I don’t think we even knew the word ‘mentor’ back then quite honestly. I think that’s more of a modern day word, but he was my boyfriend, my man about town, my counsellor. So if that all adds up to a mentor, that’s what he was. He was a super mentor because he covered all bases. He was my lover as well.

So that was what gave you the courage to take that first step?

It wasn’t even a courage thing. I assumed he knew what he was doing. He sure looked and acted the part and I figured anyone who could come all the way from the Basque Country and have a big car like that had to know what he was doing. I later found out he wasn’t from the Basque Country. His mother told me he was from 145th Street, otherwise known as Harlem. I also learned his name wasn’t Ramóne Simóne, it was Ray Simon. So he was a great self-marketer – I remember my mother saying after she met him that first night, “He’s a phoney” and my outraged response. “How could you say he’s a phoney?  You’re just uncomfortable because you’ve never met anyone like him,” blah, blah, blah. But of course, my mother was right, she always was. But he was a good phoney because he was someone who had come from nothing, with nothing going for himself, and made a success of himself. So he just merchandised himself in a much more interesting way, which was certainly impressionable on a young 23-year-old.

So how did you carry on with the partnership with him and then set up on your own?

Something went awry. He fell in love with my secretary, Tina. Those little details make a change. But what happened is I moved in with him, about a year and a half after I stayed at that hotel. Initially, I got two roommates, and then later I moved in with Ray. But once I moved in, I also found out he had three young daughters and they moved in with us too!  So I became Mrs. Mom at a very young age raising those three girls.

So seven years after I had met him, (I was his sort of wife – even though I wasn’t a wife) he came home one night while I was making pasta for the girls. I remember it because I was dumping the pasta in the strainer and the steam was in my face, and he said: “We have something serious to discuss.”  I said: “What’s that?”  He said: “I’m going to marry Tina.”  I couldn’t believe it. It seemed like a joke.

Anyway, I moved out that night and then I continued to work with him – and Tina – because he reminded me that I couldn’t fire Tina, which I wanted to do because it was very uncomfortable. But he reminded me he was the 51% partner and I was the 49% partner and he was in charge, which was true. He had never used that before, but he clearly was in charge.

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Stephanie J. Hale

Stephanie J. Hale is award-winning author of 9 books including 'Millionaire Women, Millionaire You', "Celebrity Authors' Secrets' and 'Millionaire Author'. She is a former BBC and IRN news reader, who now specialises in helping celebrities and public figures to write and publish books.