What Barbara Corcoran Really Thinks About Women Entrepreneurs

Jenna Kutcher 

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October 28, 2019



How to turn $1000 into a billion dollar business. With a B. That’s B for Barbara Corcoran. Listen, I know that first line feels click bait-y but I promise there’s a pay off here. Barbara Corcoran is taking the Goal Digger hot seat and I am so excited about it.

Maybe her rags to riches story can’t be perfectly duplicated (she even says in this interview that there’s no formula). And maybe she can’t give us the perfect 1-2-3 steps to transform from diner waiter to real estate mogul. But I’m willing to bet that you don’t reach Barbara’s level of success without a keen eye for a good investment, good people, and truly caring about what you’re doing. I want to hear her advice on all of it.

We’ve got a Shark on the show and I’m treating it like a masterclass in pitching, selling, investing, and motivating yourself in business through truly caring. This conversation speaks to anyone, no matter what your business looks like — product or service, online or in-person, new to the game or seasoned pro… We’ve got you covered.

Lucky Breaks and Hard Work

Barbara has a strong believe about success: It’s a mix of lucky breaks and hard work. Her first lucky break was meeting a man who sat down at the counter in the diner where she worked and falling in love with him.

He would be the person that would lend her $1000 to start her first brokerage firm alongside him. They ran it together with success for 7 years.

She said, quite candidly in our conversation, that the next lucky break was that same man (her boyfriend at the time) running off with her secretary. Barbara ended the brokerage partnership with him and despite her confidence disappearing, she started over again. That was how she learned her ability to succeed was totally within her, and not that man.

Identifying Talent

Barbara sold her second brokerage firm two decades after she started over. She had nearly 1,100 people working for her at one point, and she knows one of her biggest strengths is identifying talent.

Today, in her television and personality career, she has a team of five people. Just five. She calls them her “Mighty Mouse team” with each person capable of the work of three people.

I asked Barbara about identifying talent because I know so many of you are solopreneurs thinking about making your first hire. “The most difficult person to hire is the first hire,” Barbara said. And I couldn’t agree more.

“For women, the first hire is twice as hard,” and Barbara admits she hasn’t cracked the code on WHY that is, but she emphasized the importance of making the first hire to take the things off your plate that you hate to do or that you’re not good at yourself.

Barbara works with many entrepreneurs who can’t afford to hire someone… So they barter. A trade of services from one entrepreneur to another has proven to be a great strategy to get someone on board who can help you grow your business.

“You need to take the leap of faith to see what your time is worth,” Barbara encouraged. Press play to hear the full chat around hiring, because Barbara and I go back and forth on this topic and I loved what I learned from her here.

Why Being a Woman in Business is Better

“Women are better than men… And I know I’m not supposed to say that!” Barbara started our conversation about women in the entrepreneurial space with confidence. She’s seen and worked with women and men across a full spectrum of business endeavors. Her first hand experience has shown her that men have a considerable advantage in this space.

“Women are smarter in business because they’re better with people,” Barbara explained. She’s seen that there’s less ego involved. And the tendency for women to feel insecure allows us to have more empathy in business, “A woman who leans in to hear what someone else has to say won’t ruin your business. You can’t listen too much,” she advised.

“Women build better teams… For me to suggest to a guy that he lean on his teammates and give every man and woman equal power, and bring out the best in this [person] or promote this person, it’s a hard sales argument to have. But to have that conversation with women? It’s like breathing. It’s natural to them.”

Tips for Selling

Barbara Corcoran’s advice for women who battle a fear of selling is powerful: “I think women wrongfully see the sales pitch as asking for something. And it’s not.”

“Speak from the heart what you believe and put it on the table. It’s not your job to make somebody buy it. It’s your job to present it and to believe it,” she continued.

I could quote her word for word, right here in this blog post, but I encourage you to press play to hear it from Barbara Corcoran directly. Essentially, Barbara stands with the sales philosophy that if you’re fearing the sale then you don’t really believe in what you’re presenting, and that means you shouldn’t be selling that.

The formula for closing a deal lies within presenting with enthusiasm about the product or service or whatever thing it is and listening for the reaction from your audience. “And closing a deal is just about being around long enough with the client or customer until they get comfortable with the idea of saying I do,” she said. It’s not an aggressive act, but it is persistent.

Money is Not the Motivator

Her brokerage grew to a billion dollars. That is a substantial amount of money in any reality. Now that she has money, what is the motivator for Barbara? What launches her out of bed in the morning for a 14-hour day on set at Shark Tank?

“I’ve never met a hugely successful person in business whose goal was to make money. Making money was a side benefit. Most of us are surprised by making money,” she started.

“I did aspire to be the Queen of New York real estate from day one!” Barbara continued, but her main goal and motivator at the start of her business was to create a happy family and happy company culture within her firm. And that is what she created while the money followed.

Mid-conversation I took a pause to affirm Barbara. It was so clear to me that she really cares. She shows up in a way that others a space to be heard. She told a story about her mother that is best heard firsthand (so press play on the player above!) but continued to share this piece of advice:

“The business angle of really caring? It works. If you don’t fake it, that means you’re doing a good job and you’re pouring yourself into something. What you really get out of caring is you get satisfaction… So why wouldn’t you care? Caring is where you get all the good stuff.”

More from this Episode

This is one of the most comprehensive, insightful, and entertaining interviews I’ve hosted in a while. I cannot get enough of Barbara’s advice and no-BS attitude. Press play to hear her criteria for investing on Shark Tank (and why she cares about hardship over privilege), what happens after the cameras are off and the Sharks get ready to put ink on paper, plus Barbara’s advice if you’re just trying to make your next $1000, not build a billion dollar empire.

Find Barbara Corcoran’s Business Unusual where ever you listen to podcasts and look for her new show 888-BARBARA due out soon.


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  1. […] Bonus! Listen to Jenna’s inspiring interview with Shark Tank’s Barbara Corcoran here […]

  2. […] started out in real estate. She’s also a mom, and she tells it like it is. I really enjoyed this episode of “The Goal Digger Podcast” where Corcoran was interviewed, talking all about her career path and […]

  3. […] only does Jenna give away her best tips and advice, she often has incredible guests such as Barbara Corcoran from “The Shark Tank” and Katrina Scott, co-founder of Tone It […]

  4. […] Episodes:Defining Enough as an EntrepreneurWhat Barbara Corcoran Really Thinks About Women EntrepreneursThe Secret to Rest and Why It’ll Make Your Business […]


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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