From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (2024)

The story of Barbara Corcoran is one that many aren’t aware of. She is a native to New Jersey and started her booming real estate business in New York. It is very rare that you hear about an ex boyfriend stealing your secretary away and marrying her!

Well this is one of the many things that Barbara encountered and believe it or not, if it wasn’t for this happening, she wouldn’t be where she is today. She split her company with her then boyfriend into two. He took half and she took the other half. They moved office floors and she began The Corcoran Group. It’s been history ever since.

Read along for more about Corcoran.

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (1)

Photo sourced IMDb

Barbara Corcoran Overview

Barbara Corcoran is more than just her role as an investor Shark on Shark Tank. She is a business mogul and a female entrepreneur that has herself dipped into many different industries. The New Jersey native worked 20 jobs by the time that she had turned 23 and since then she has been unstoppable. She was a waitress at a diner when she met her first boyfriend (she didn’t know it at the time) but he told her that she was meant for more than the diner lifestyle and she should move to New York.

Together, they moved to New York and she was given a $1,000 loan by him to begin her journey in real estate. With this $1k, they got an office space, grabbed some desks, got the 8th floor of a building and hired some employees. One day, Barbara was home with her boyfriend when he told her that he was going to marry her secretary. She couldn’t believe it. She took all her things, left and was couch living with her friend until she could get back up on her feet. They returned to the office and for 2 years, she worked with her ex and his new wife (the secretary) until one day she couldn’t take it anymore.

She took her broken heart and said she was going to leave and start her own company. She took half the employees and he took the other half. She got the same office space a few floors up and by the next week, they had their new office and new space ready to take on New York. Before she knew it, Barbara had turned this $1k loan, into a billionar dollar business and since then has went from real estate, to investing, public speaking and more. Watch the full interview with Barbara Corcoran below. Years later, she sold The Corcoran Group for $66 million dollars after receiving that $1k loan from an ex. Read more about Barbarahere.

Life in New Jersey

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (2)

Via Barbara’s Instagram @barbaracorcoran

Barbara Corcoran was born and raised in New Jersey. More specifically the town of Edgewater which is now known for its shopping centers, waterfront homes and more. She was born on March 10th in 1949 and had a tough time growing up when it came to the education system. Barbara realized she was suffering with dyslexia as she got older when her grades, assignments and public speaking in class was taking a turn. She would be made fun of by those in school and was even labeled a “dumb kid” because she was a D student.

She grew up in a house of 10 siblings total, including her with 6 sisters and 4 brothers plus her parents. In many podcasts, interviews and articles, Corcoran mentions that her parents were a huge inspiration and would always help her stay creative. Her dad was never able to hold a job down and she’s mentioned before in many podcasts as well that her dad was meant to be a business owner and have his own rules because he had all the traits of it. Barbara said her mother was extremely positive and always combined this with her efficiency.

Whenever he would come home early on a weekday, all the siblings would gather around and her father would say, “guess what kids?!” and they would all scream “you got fired?!” and everyone would cheer. Their dad would give a story about how he told a manager or his boss to shove it where the sun don’t shine and that’s most likely how a majority of his jobs would come to an end. However, a few weeks later their dad would always find a new role. From her dad, she learned the power of play which was not that parents take their kids on fancy vacations, but instead to be in the moment and do fun or bizarre things that they’d remember.

Every time her mom would come from the hospital with her new sibling, her mom would stick them with a specific trait such as a dancer. She would gather all her siblings around and give label them with these fun roles to contribute into the family. Barbara was given the creative and fun sibling role to bring everyone’s imagination together. On rainy days, Barbara’s mother would tell her to take all the kids into the basem*nt and make a fun game with her imagination for all the siblings to be together.

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (3)
From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (4)

Photo sourced here: Barbara Corcoran Facebook

From Diner Jobs to New York

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (5)

Barbara Corcoran Photo Source CNBC

Barbara was working multiple jobs growing up and had about 20 different roles before she made the change to go to real estate in New York and this happened purely by chance at her job while she was 23 working at the Fort Lee diner. She was in charge of one whole counter at the diner and this was her job at the moment.

It was a normal day at the diner, she was working and suddenly a man named Ramone Simone walked in and this would be her soon to be boyfriend. He offered her a ride home in his car and she introduced him th her family and both her parents hated him as soon as they started dating. He told Barbara that she was meant for more than just being a waitress at a diner but that she should consider moving to New York.

Simone told her that she was meant for this big life and of course, Barbara said yes. He booked her a one week stay at the Barbizon Hotel for women in New York and it was a block away from Bloomingdale’s. She couldn’t believe that she was going to New York. She told her mom she was leaving and going to pursue this. Her parents did approve but she went off anyway.

Ramon gave Barbara $100 to buy herself a suit and so she did. She got a lavender stretch top, lavender suede pants and lavender boots. She walked to the Barbizon and felt super cool.

While she was at the hotel and had this lavender outfit, her and Ramone decided to start real estate together. She was working as a receptionist during this time for a development company. He was going to be the finance partner and she was going to be the working partner.

Ramone took 51% of the company and Barbara took 49%. For the next 7 years, they built their own rental company in NYC in a sublease space with 14 rental agents. She was earning more money than she was earning as a receptionist and felt so great about her life.

They were very successful in the beginning however, this is where the part of Barbara’s life took a turn that she could have never imagined. When she was living with Simone, he came home one day and told her that he was going to marry their secretary Tina, from the office. Barbara couldn’t believe it. She packed her things, left the apartment and moved in with her friend Kathy. Barbara was staying on her couch until she was able to get back on her feet again.

She felt like a nobody. She was turned down for a woman 5 years younger than her. Barbara continued going to work everyday seeing Tina and Ramone together. She wanted to fire Tina but couldn’t because Ramone was the controlling partner of the company. She had a broken heart and lost confidence due to this.

Barbara felt like nothing now. Her boyfriend had left her for another woman and Ramone was the only one supporting her. He had given her this whole new life she didn’t think was possible without him. Ramone was her mentor, her love, the one who gave her confidence and more. She really felt like she wouldn’t succeed without him. One day she decided she was going to do this anymore.

She walked over to Ramone one day and said that she was ending this company. They were going to divide the 14 people they hired and give 7 and 7 to one another. Within 6 minutes they ended a partnership like that. They had $37,000 in cash and wrote Barbara a check for half of that. Just then, a real estate recession happened. This was great because commercial space wasn’t leasing well. She ended up renting up a few floors above from their original office space and this was on a Thursday. By Monday, all the sales people that Barbara had picked were in their office and Ramone was with him. This was the beginning of The Corcoran Group.

Barbara found out from Ramone’s mother that he was from Harlem and his real name was Ray Simon. Not this whole persona he had put on to make himself seem cooler than he actually was. He ended up telling her that as she left, she would never succeed without him. Every time Barbara was near death with the business, growing it up and down, owing money or facing anything, she remembered this insult he said. She thanks him a million times for this because if it wasn’t for that comment, her life wouldn’t have turned out the way it did.

Lessons from Barbara

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (6)

Barbara Corcoran Facebook Photo Source

Lesson #1: She is great at failure.

She had 23 jobs before real estate. She was fired from 3 of those. She started 3 related businesses to real estate that she thought would be successful. Out of the 3, only one had done well and she realized that people don’t even care about the failures. They only count the successes. She had 2-3 losses for every 1 great thing she did.

Barbara was invited to speak in front of 80 bankers at CitiBank. At this speaking engagement, she opened with a joke and realized the joke didn’t go that well so she froze and was asked to sit down by the moderator. She was mortified but instead of letting this get to her, she signed up for a class at NYU to teach for 14 weeks with 6 kids in the class. 2 nights a week for the summer, she taught real estate and how to sell it in NYC.

In this class, a lady named Carrie Chiang came to her. Barbara’s top sales person was making $35,000 for the year and at the time this was amazing money. Carrie said she had over $200,000 from real estate. Barbara’s one goal was to get this woman to work at her company. One thing that Carrie discovered was that a new product in New York was going to take over and this was called a condominium as we know it today. They were being built and she had people from Taiwan come to buy these. People from New York weren’t buying it so she had them come.

Carrie was the number 1 sales person in New York City within the next 6 months. All of Barbara’s employees at her company also got famous because of Carrie since she was such a headliner in the news. Every January, Carrie will call Barbara and say how much she has made in January to joke with Barbara.

Barbara’s main goal was to collect the best sales people for her company. The problem is that if she was getting all these great people, they were all obviously not going to like someone being better than them so she had to create a positive work dynamic for everyone.

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (7)

Photo Source: Barbara Corcoran Instagram

With Carrie and all the top sales people she hired, the ones making millions and the ones only making $40k, wasn’t the background, schooling or where you were from. The difference was that it depends on how you take a hit. Her great salesperson can take a slam down from a rejection and it wasn’t because they didn’t feel it but they took less time to feel sorry for themselves. Her sales people she had to fire were the ones that got abused over and over from not getting sales and felt too sorry for themselves.

The top qualities of her employees are that they have empathy. They can read people and know what they are feeling. The other is that they have no ego, no drive and no real need to succeed.

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (8)

Barbara Corcoran Website Photo Source

Lesson #2: Perception creates reality.

Fake it until you make it. Barbara’s mother always reminded her to always be a good person and people will recognize that. Although this philosophy wasn’t good in the business world, Barabra noticed she had to develop a big mouth in New York in order to be noticed. So she began this thing called The Corcoran Report.

She ran to Bergdorf Goodman and got a fancy coat after getting a check. She bought a long red, fancy coat and wore it for 4 years over her not so fancy clothes. People responded differently to this coat than the one she had from New Jersey. She had to create the image of success for people to see it and they did.

People from her office were complaining about her not advertising. But she had no money for advertising and she was desperate. She needed more people to notice them. She took 11 sales and came up with an average price based on this for the year and typed on her typewriter, an analysis of numbers.

She put the average New York City apartment price, folded it and sent it to every reporter for the New York Times named after her. She never got a call but after she hand addressed the envelopes and sent them off, two weeks later she opened the New York Times on a sunday and on the front it had a headline that said “New York City prices hit all time low” and the second line said, “according to Barbara Corcoran of the Corcoran Group.” She cut it off from the paper, brought it to the office and hung it there. She showed her sales people.

Everyone hustled and she heard all the phones ringing asking for listings and numbers. They went from nobody to somebody in a day. She realized what happened and that the New York Times became her partner. She churned out this report, got a new red suit and became the lady known for reports in New York.

She even did a Madonna report because she saw Madonna was pregnant looking for an apartment. They didn’t have Madonna but she still wrote a report on what kind of apartment Madonna would want. She said that Madonna would need a doorman service, high views in the city and took more from the dream list. She was on 4 television stations in a week because Madonna was in the news and it was her name under most of it. No one asked Barbara if she was even working with Madonna!

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (9)

Business Jet Traveler Photo Source

She was named a celebrity broker but she never got Madonna because she never even ended up moving. But she got a call from an agent and was on another news station. He told her that he had a celebrity client who would be interested in working with her and it was Richard Gere. She made a Richard Gere report and leaked it to the press.

Everyone went on about this and then she got an endless amount of referrals because of this. This leads to the perception she created for herself. She wasn’t a celebrity real estate agent but she wrote about celebrities which lead real ones to come to her. Anything she dreamt of becoming, she put it in the public eye, figured a way to keep up with this and herself.

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (10)

Barbara Corcoran Photo Source: NY Times

Lesson #3: Everybody wants what everybody wants, and nobody wants what nobody wants.

She was asked to come to an insurance company to teach how to sell 88 apartments. She came in and saw they had 88 terrible apartments scattered around the city. The apartments were in horrible condition. Some half built kitchens, none painted and they wanted to sell the apartments but she said they couldn’t. But then, a week later, she was writing her out of business letter in January because she owed Citibank over $300k and they were in another recession. A lot of her other competitors were also out of business. She was writing this speech and something came to her head.

She remembers that when she was younger, her mother would take all siblings down to her grandpa’s house in Toms River, New Jersey. This woman there was selling baby jack russels. The dog lady had people on the front of her lawn arguing because she invited everyone who had a 12 pm appointment and there weren’t enough dogs for everyone. Everyone was complaining. The puppies flew out of the box and everyone argued over who would receive one. But this was a lesson that she took with the 88 apartments. She had an idea.

She would take the total amount that the insurance company told her the apartments were priced and divided it by 88. She had a huge one day sale and advertised. Instead of saying the business was going out of sale, they had a first come, first service sale and you had to line up in person. She stayed in business one more month to get this rolling. They priced even the apartments that had high floors, stunning views, and more. You had to get there early to get the best ones. On 82nd street at 7 in the morning, they had a whole line of over 300 people wrapping around these New York blocks of people that came for these 88 apartments..

They made a clause that everyone had 2 weeks to review their signed contract with an attorney. This brings back to the saying that Barbara mentioned earlier which was “everybody wants what everybody wants, and nobody wants what nobody wants.” In one day she made a million dollars in net commissions that were going to be paid in a month. She paid off Citibank, paid off an advertising agency and opened 2 more offices.

People started calling listings and she got all the publicity of the sale everybody in town was talking about. This ended up keeping her in business because everybody wants what everybody wants, and nobody wants what nobody wants. These apartments could not be sold for over two years but she turned it into a rare commodity and advertised it like this. Everyone wanted them right away.

She found there was never really a good time to expand but she always expanded and this is what she practiced religiously. This grew her business because she said “you have to realize if you’re the little guy and you got the big guy up here, you can’t do the same thing. You’ve got to do like five times more to catch up. So I practiced if I had a sales organization of 25 people and I thought, “you know what, I’m going to hire an office that could hold 50.” She did this because she was going to double the size.

After she had the space, she went out and worked hard until she got the office for 100 people. And then she stared at this empty space and thought of it like a closet. It never stays empty for long. Her focus was finding sales people, training faster, getting them to be more productive and leapfrog over her competition because of how aggressive she was with expanding.

Lesson #4: There are two kinds of people: expanders and containers.

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (11)

Barbara Corcoran LinkedIn Photo Source

She hired people in her office that were exactly like the opposite of her. And she would sit these people all equally which isn’t usually the case, but she made everyone partners and had them run around the office. These were the containers. She had people good at media, people good at recruiting, people good at making friends and more.

They had a media and advertising company come in and change her advertising every few years. She would ask her employee which one of the ads she liked the best. The one that her employee Esther didn’t like is the one she picked because she knew that this would have a reaction against people and it would make them look. Esther was her container because she was the opposite of her. Barbara was the best expander. The quicker that you can expand with a container, the more you can size the company up and hire better.

Barabra was keen on firing people religiously every 6 months. This was important to have a good system of fair play. They have to make a sale within 3 months and if not, then you’re out. If you can’t make this sale, then you’re just not a good salesperson. She created a system where she was constantly taking out this dead weight. Everyone knew the rules of this. She was also a stickler with negative people. She made sure no negative people would stay at her company, even if they were a top salesperson. Barbara says that negative people are like a cancer among others. It takes healthy people and makes negative thinking very contagious among them.

If Barbara had looked at the worry of failing, she wouldn’t have done everything she did for her business to grow it and scale it like she did. She thinks in the habit of constantly trying and never to win. She goes up and just puts good practice towards trying. Barbara sold The Corcoran Group in 2001 for $66 million dollars. Her original offer was for $21 million but she turned it down. She said nothing less than $66 million and the offer was made.

There are many lessons and notes we can take from Barbara’s story and throughout everything she went through, you can see that she constantly was persistent, used this insult to keep her going and always thought of top notch creative ways to stay afloat. This has led her to her life now where she is an investor on Shark Tank, does many public speaking events and helps other aspiring entrepreneurs.

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From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (12)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (13)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (14)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (15)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (16)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (17)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (18)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (19)From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (20)

From Heartbreak to A $66 Million Dollar Business: Barbara Corcoran’s Story & Her Entrepreneur Journey (2024)
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