Barbara Corcoran has never been afraid to fail.

In fact, she wears her failures like merit badges, showing how they shaped her journey from a $1,000 loan to a $66M real estate business and a seat on ABC’s Shark Tank.

Instead of hiding the tough parts, she shares them openly, building trust and connection with millions.

In today’s newsletter, I’ll share Barbara’s unvarnished story of failure along with:

Enjoy swimming with this shark… LG

Barbara Corcoran grew up as one of 10 children in a poor family in New Jersey. The size of the family forced her to learn quickly that the only way you get attention was to talk the loudest and most frequently or you would disappear. 

That skill helped her develop the gift of gab at home, but at school it got her into trouble all too frequently. Barbara could not read or write when she entered 3rd grade, so they sent her back to the 2nd grade. She felt ashamed of herself that day, and to rub salt in the wound, the teachers told her she would always be ‘stupid’ if she didn’t learn to pay attention.

That was the first time she truly discovered that she had a label, and it was about failure, a lesson that would stay with her for years to come.

School was never easy for her. Sometimes she would get straight D’s, but she stuck with it, determined to get her diploma one day. Because she didn’t have any money, she started working at the age of 11 while going to school.

By the time she finished college, Barbara had worked 20 jobs doing everything from selling hot dogs to working as an orphanage housemother.

After graduating from college, she started working as a waitress where she met Ramone Simone. Ramon liked her charm and thought she would be great in sales and said he would loan her $1,000 to start a real estate company that they would co-own. They gradually built the company over the next few years and eventually started seeing each other. 

However, two years after they had been dating, he decided to marry his secretary instead of her. Barbara was heartbroken and started to lose confidence because she felt she was nothing before Ramon found her.

One day, she decided she was not going to do this anymore. She got up enough courage to leave and told him they were going to end the partnership. Within 10 minutes, they split the company, and they each got 7 salespeople and half of $37,000. 

On the way out, he gave her the gift of a lifetime by saying to her: 

That statement left a scolding tattoo on her heart, but a mark that motivated her like nothing else. She vowed to herself that he would never see her fail. She saw it as her insurance policy for success. 

Four days later, she rented a space, phones, and desks four floors above her old offices and started her new company. She was off and running, making more on her own that next year than they had done together.

As Barbara started to grow her business, she got her first public speaking opportunity in front of 300 bankers. She practiced every day for over three months, memorizing every word, making sure she was prepared for her big day.

But when the day came to speak, she couldn’t utter a word in front of the crowd. 

As the moderator said thank you and asked her to sit down, she felt like a failure and swore she would never speak again.

Shocked and still embarrassed, a few days later she decided to get over herself and signed up to teach real estate for 12 weeks at an NYU annex classroom. In that class, she met the woman who would become her best salesperson ever and be the #1 real estate salesperson for the next 25 years in New York. 

Barbara realized that if she had not failed on that podium, she never would have met this woman.

As she started to sell more homes, she came up with an advertising idea to get more exposure. Typically, you put an advertisement in the New York Times or Wall Street Journal, and then they call the agent to make an appointment to go see it.

She decided to take the property to them by videotaping the home and the agent so the customer could see all of the properties without ever leaving their current house. 

She spent all of the first year’s profit, $77,000, to buy the video camera and film everything. But the agents never handed out the tapes because they wanted to keep control over the relationship, or they were afraid that a customer would see another agent on camera who was more attractive and want them to help. It failed miserably.

As she was preparing for a big sales meeting, she didn’t want to admit that she had failed. That same night, she was having dinner with her husband, a Navy Captain, who had just gotten back from Korea and was explaining how excited he was about his most recent trip there. 

They were using this thing called cyberspace to play war games. They were doing it in real time on this thing called the Internet and it changed everything for how they did their military maneuvers.

She had no idea what the Internet was, but it gave her an idea. 

She registered The Corcoran Group’s URL the next morning and took all the videos and put them on this Internet thing. In the sales meeting, she announced,

They had two sales out of London within that week.

By 1993, they were selling real estate online, two years before their competitors. Barbara also registered all the URLs for her competitors who had a brand so that they’d have to come to her when they wanted the name. 

She didn’t charge them for the URL. She just wanted them to call and ask for it so that she’d know when the competition started selling online. The little guys, who had to be creative, called first. The largest companies called last.

Barbara’s company was about to go out of business during a down period of the industry, and she owed the bank $380,000 with no way to pay it. She got approached by an insurance company to sell 88 apartments that were in poor condition, overpriced, and spread all over town, so she said no. 

She saw eight Jack Russell puppies in a cardboard carton. There was a line of fancy cars from New York all arguing, trying to buy one of the puppies. 

Barbara’s mom told her to sit back and watch and explained that the woman selling the puppies was pretty smart. She invited everyone to come at the same time. Everyone had a 12-noon appointment, and there weren’t enough Jack Russell puppies to go around.

In that moment, she made a parallel between those puppies and the 88 apartments. She went back to the insurance company and asked what the total price they wanted was. Then she divided that number up by 88 and priced them all alike. 

They didn’t have any money for advertising, and neither did Barbara, so she quietly announced to her staff and clients about a one-day sale. Only tell your relatives and your very best customers. There weren’t enough to go around. She held a one-day secret first-come, first-serve one-price sale. 

Three hundred people showed up for those 88 apartments. In 90 minutes, she made $1.2 million in commissions and paid off all of her debt. Those apartments had been on the market for two years with tons of advertising, but no one wanted them. She made them a rare commodity, and everyone wanted them.

That first real estate company, NRT, sold for $66 million. Today, Barbara is a nationally known real estate expert and is a regular (Shark) on one of TV’s most successful business series, ABC’s Shark Tank. Barbara has reported having invested in over 130 companies via the show to date. Her estimated portfolio value exceeds $100 million, and her investments have generated approximately $700 million in combined revenues across her portfolio companies.

Barbara Corcoran’s life story is full of failure, resilience, and ingenuity. Her ability to turn setbacks into stepping stones, embrace vulnerability, and connect through vivid storytelling offers a roadmap for founders who want to inspire and influence others.

Here are three storytelling lessons you can learn from Barbara:

1. Embrace Your Failures Like Merit Badges
For Barbara, failure is a badge of honor. Every major business breakthrough happened right after a terrible, embarrassing setback. From being labeled “stupid” in school to freezing on stage during a big speech to being rejected from Shark Tank, she used each low point as fuel to push forward.

Adopt a “failure-is-an-asset” mindset by seeing each misstep as a learning opportunity. The next time you face a setback, write down 2 things you learned, and one action you’ll take to move forward and use that as part of your story.

2. Don’t Be Afraid to Be Vulnerable
Barbara’s willingness to share her low points, growing up in a cramped house with nine siblings, or being dumped by her business partner, makes her feel human and sucks you into her story. She doesn’t just tell you what happened; she tells you how it felt and it makes you root for her. 

You can build trust the same way. In your next pitch or post, share a moment when things didn’t go as planned, how it made you feel, and how you grew from it. Vulnerability doesn’t weaken your story, it deepens it.

3. Share Relatable Details
Barbara’s stories stick because they’re full of specific, emotional detail. Whether it’s the Jack Russell puppy sale or her disastrous sales pitch, she paints a picture that draws you in and makes the lesson memorable.

When you tell a story, don’t gloss over the little things. Mention what you were wearing when you made your first sale or what was going through your head the first time you heard “no.” These details make your story real, and make you more relatable. 

A Stackla survey found that 88% of consumers consider authenticity a key factor in choosing which brands to support. That’s because trust grows when people see the real, imperfect human behind the brand.

Sharing honest stories of failure, like Barbara’s early struggles, doesn’t weaken your image; it strengthens it. In a world of filters and polish, authenticity cuts through the noise and builds real connection and credibility.

In this TED talk TEDxBarnardCollege – Rethinking Failure – Barbara Corcoran, Barbara shows why she’s a natural storyteller, starting with a personal story that immediately pulls you into her life. She shares how failure shaped her journey from that = $1,000 loan to becoming a Shark Tank investor.

Through her candid and relatable style, Barbara offers a fresh perspective on failure and how it can drive success. Watch to see how she uses storytelling to connect and inspire.

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