22, that is how many jobs Barbara Corcoran held before she decided to start her own business.  Switching through jobs 22 times seems like Corcoran had a difficult time holding onto a job. Surprisingly, that wasn’t the case.

According to her, she enjoyed every single job she held. So why did she leave to start a business? Although Corcoran may have enjoyed her job and probably did it well, she didn't like having a boss.

“Other than that one exception, I enjoyed every one, the only piece I didn’t enjoy was having a boss,”

Her drive to be her own boss, a hasty decision, and a specific skillset is all it took to make Corcoran a successful entrepreneur. Here’s how it all began and what lessons other entrepreneurs can learn from her story.

It Wasn’t Even My Idea

Corcoran made her wealth in real estate. But, why real estate? That wasn’t a decision she arrived at on her own, it wasn’t even her dream job. The idea to go into real estate was her ex-boyfriend who also gave her a thousand dollars to start the business. Corcoran’s ex-boyfriend had observed she was ”really good at real estate sales” and so he encouraged her to go into real estate. The rest is history. Somehow, Corcoran was able to turn the one thousand dollars into a five billion dollar company known as Corcoran Group and this one skill made it possible.

I got along with people very well

While working as an employee, Corcoran honed her people skills. It wasn’t clear from the start that this was one skill she would be depending on in the future. But after she became CEO, Corcoran quickly realized that her biggest strength is her people skills, and she owes a huge part of her success to this one skill - getting along easily with people.

“I didn’t realize then that it’s the perfect background for real estate or the perfect background for any sale position.”

With this one skill, Corcoran was able to connect with her clients and bring deals. But what she lacked was the ability to close these deals, which is the whole point of sales. Corcoran struggled with closing deals, calling herself “the worst closer out there.

She believed this challenge wasn’t unique to her and that the best salespeople were better at bringing in deals than closing them. Knowing this to be true of herself, Corcoran had to figure out how to close deals. Her solution was simply delegating that part of the job to someone good at it

I am terrible at closing deal

While most people may want to learn and improve on their weaknesses, Corcoran chose not to. Instead, she delegated the tasks that were outside her strength. So whenever there was an extra commission not being put into rent or bills, she would use it to hire a salesperson. Someone better than herself at closing deals.

For Corcoran, hiring salespeople for her business was an investment because salespeople brought in commissions and with more commissions, she could hire more salespeople. With this simple strategy, she killed two birds with one stone. By focusing on hiring salespeople, Corcoran closed more deals, made more commissions, and expanded her business, at the same time she cut down expenses as she rarely hired anyone who wasn't a salesperson.

Her reason is that “Salespeople produce income, everyone else costs money”. Startups are often on a tight budget so it makes sense that she only spent money on things that were guaranteed to generate more money. To cover up for the other roles in the business, Corcoran implored her salespeople to take on extra roles until there was a budget to hire.

Identifying and Managing Talented Employees

“People stayed with me and worked extra hard for me because I could see the potential in them – I’m not so sure they could see the potential in me.”

One thing Corcoran had going for her was her people skills and this helped her identify exceptionally talented individuals whom she hired to work for her, the same skill must have played a role in making her “likable” enough for these individuals to willingly take on additional tasks and work for long hours. Typically, one would expect a high employee turnover under such working conditions, to which Corcoran was quite shocked that wasn’t the case.

“I was rightfully scared because they had the talent, they knew what they were doing, and they had the confidence. I was so surprised – no one ever did.”

Motherhood and the decision to sell

At the age of 46, motherhood came knocking on her door and Corcoran knew it was time to make some changes in her life to accommodate the little human she was bringing into the world.

“I wanted to be a 150% entrepreneur and a 150% mom, and I found that I was having a very hard time doing both. I was about 75% and 75% – still better than 100%, but not what I was accustomed to at work.”

This realization was a precursor to her decision to sell the company, but what actually gave her the push was realizing her company was the largest in New York City at the time and that means she had the upper hand in an acquisition negotiation. Without wasting time, she made the call “I’d like to sell my firm”.

To her, making the decision was easy. The buyers offered the best price and after just 4 months, she left the negotiation table with 66 million dollars. Once again, her deep understanding of people helped her press for what she believed was the value of her firm despite the “French Kissing” tactics employed by the other side.

“I learned that they’re going to beg to give you French kisses the day before the closing, and they’re not going to remember your name the day after – no matter what they promise you. You are an unwanted visitor in your own home the day after the closing.”

Lessons from Corcoran on Building a Business and Selling Successfully

Barbara Corcoran’s journey from a $1,000 investment to a $5 billion real estate empire offers valuable insights for entrepreneurs. Her success wasn’t just about hard work—it was about leveraging her strengths, making strategic decisions, and understanding people. Below are five practical lessons entrepreneurs can learn from her story.

1. Leverage Your Strengths

Corcoran discovered early on that her biggest asset was her ability to connect with people. Instead of trying to master every aspect of sales, she focused on building relationships and left deal-closing to those who excelled at it. Entrepreneurs should identify and lean into their strengths rather than trying to do everything themselves.

2. Delegate Your Weaknesses

Rather than struggling to improve at closing sales, Corcoran hired people who were naturally good at it. This lesson applies to any business—founders should focus on what they do best and delegate tasks that fall outside their expertise. Hiring the right people can accelerate growth more effectively than trying to do it all alone.

3. Hire for Growth, Not Just Operations

Corcoran prioritized hiring salespeople over administrative staff because sales brought in revenue. She understood that in a startup, every dollar spent should contribute to growth. Entrepreneurs should take a similar approach by investing in roles that directly impact revenue before expanding other functions.

4. Recognize and Retain Talent

Her ability to identify potential in employees and make them feel valued contributed to strong loyalty and work ethic in her team. Entrepreneurs should not only hire talent but also nurture and retain them by recognizing their value and providing opportunities for growth.

5. Know When to Exit

Corcoran sold her company at its peak when she had leverage in negotiations. She recognized that timing is crucial in business—whether it’s scaling, pivoting, or selling. Entrepreneurs should keep an eye on market conditions and be strategic about when to make major moves.

Final Note

Barbara Corcoran’s story proves that success in business is as much about understanding people and playing to your strengths as it is about having a great product or service. Today, Corcoran sits as a shark and an investor with the likes of Mark Cuban in the hit series Shark Tank.

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