Barbara Corcoran talks about waitressing, happiness, and advice from Mom & Mark Cuban!

Nobody but nobody would have predicted the fate of Barbara Corcoran. The Shark Tank investor and native New Yorker left a trail of straight D’s in school, and began her adult life working a series of odd jobs (secretary, hospital admin). She suffered from dyslexia, a disorder that had yet to have a name or an understanding. That didn’t stop her – nor did anything else – from working 18-hour days, punching clocks.

As a diner waitress, one of her customers became her boyfriend, and he gave her a thousand-dollar loan to start a business. The result: a real estate company called The Corcoran Group. In 2001, she sold that company for $70 million, but not before becoming one of the most powerful brokers in New York. To this day, The Corcoran Group remains a real estate juggernaut, and Barbara’s story has become legend. 

Since then, Barbara’s honesty, genuineness and street smarts have earned her a place in the culture as a grounded, sensible, trusted voice. She and the other Sharks have helped teach America the value – and challenge -- of being entrepreneurial.

We look to Barbara for insight as we pursue a path that is rocky, unpredictable and filled with ditches and dead ends – but that same road can also lead to promise, opportunity and a rainbow’s end.

Here, Barbara tells Three Commas about what it takes:

Back when you were waitressing, did you ever believe that you would achieve the American Dream?

I didn’t even have that kind of American Dream, frankly. I was just happy doing my work. I always assumed that I would be working very hard. I always had many jobs, often two at once, even when I was in college.

Waitressing, by far, was one of my favorite jobs, always. I didn’t really see it then, but waitressing really is the same as sales. You’re in charge of your own counter, so you have your own territory. You make friends with your customers. I made friends with everybody who walked in. I gave them a big smile, because I genuinely like people. And based on the job you did – based both on the delivery of the food and talking them up – the more tips you got. It felt – for me – always fair. 

I anticipated the fast pace of my life, but anticipating the quality of my life now? No. If you think about it, the quality of life has to do with -- more than anything else -- being happy. I was a happy kid, I had a happy family, I had a happy mother. I felt I could work and provide for myself because I always had, so I felt confident and happy. I always felt I would have a confident, happy life.

In some ways, it’s almost easier to have that when you don’t have money than when you do. Money complicates things. It spoils your kids, gives too many options, you don’t know who your friends are, you don’t know what their real motives are, you second guess a lot when the other objective that people might have has to do with money. I wouldn’t want to say that it’s easier to be happy when you’re poor, but it was less complicated.

You speak well of your mom, who raised nine kids and kept a good attitude. How did she feel about your success?

In the beginning [when I first appeared on Shark Tank], the established Sharks were mowing right over me and I couldn’t even get a question in. Upset, I called my mom, and she said, “Barbara, put the two little angels on your shoulders -- your dad and I -- cheering you on.” And I found my voice.

My mom got more of a kick out of my success than I did. Moms like to brag on their kids. There were nine of us, and she bragged on all of us, but I think she got a special kick out of [my success] – and maybe I’m not even right on that – maybe if I talk to my sisters and brothers, they would all say that.

But I think she got a special kick out of my life because she saw it as a giant adventure. She was a real New York girl. And before she got married and started having babies, she was a real New York working girl. She talked about it all the time, and I was living that enchanted kind of life that she had a taste of.

What advice or reassurance would you give to yourself if you could go back in time and sit down with that waitress?

I would say exactly what my mother said to me -- and I didn’t listen: “It all works out. Just keep working hard. You’ll see. Everything works out.” I say it all the time now.

On Shark Tank, entrepreneurs look to you for advice, guidance and hopefully an offer – but do you ever learn anything new from the entrepreneurs who appear on the show?

What I have learned is that very few people have the capacity to succeed in building a business. People may be passionate about a product they can sell, but as far as turning it into an empire, so few of them are able to do it. So few people really have what it takes. They may have the desire and the belief, but they don’t have what it takes to get there.

Of course, you have to have the dream. You can’t get anywhere unless you can visualize it. But you also have to have the talent; you have to have good judgment. You have to have tremendous perseverance. Most entrepreneurs don’t have all of that.

Do you ever miss selling real estate?

I don’t miss the selling of real estate, because I sell for a living today, selling the entrepreneurs on coming into a deal. I’m even selling when I want to hire someone for a support staff position. And I’m selling when someone already has five offers, because everybody knows they are good. I’m selling all the time to get everything I want. I’m selling all the time. That’s like breathing to me.

What I tremendously miss – and I miss it every day of my life, truthfully – is the thousand people at that business [The Corcoran Group] and seeing this huge, happy family. My management team, especially – great managers who helped me run the business. I miss my business partner, who was my operations lady, so I didn’t have to deal with all the crap I didn’t like to deal with.

Also what I miss: thinking of an [idea] in the morning and executing it in the afternoon and seeing if it flies. Anything I could create, I would write on a blackboard, and I would have it get done. That creativity board and the ability to execute on anything I could think of and see it play out and come home and make money for me -- that’s so satisfying.

How digital are you?

I run my entire life by texting and I love that. You can track everything and it’s easy to find. I love social media, but not because I know a damn thing about it. But I hired someone who knows an awful lot about it, and they’re doing a great job for me on that. But for me, I’m really surprised when I’m using anything modern.

One thing all the Sharks seem to have in common: charisma. Do you think charisma is a necessary quality to possess in order to succeed in business?

Charisma is selling -- the ability to get someone to listen and get on your side. And, if all goes well, do what you want them to do. Charisma is powerful, because if people like you, you already have a sale. And we’re all selling. We need to get people to do what we need them to do -- family, business.  I never buy into any Shark Tank businesses unless they have charisma.

Making a pitch on Shark Tank seems like it would be the most difficult thing in the world! 

The ones who are comfortable in their own skin are the ones who shine and the ones who get the offers.

We have After The Tank to catch up on our favorite entrepreneurs. You seem to be very good to your partners and treat them like family. How do you bond with your partners and how does it help grow the business?

I did that kind of thing for two years before Shark Tank even knew about it, and then Shark Tank wanted to cover it. The whole objective in getting [all the businesses] together is to become friends. I find that if everybody really likes each other, and they continue the friendship and start sharing ideas, my businesses do better and they have fun.

Most of my good businesses are owned by two people, so they have each other. But when they [connect with] other teams running other businesses, they really bond well and they stay friends. What that really does for us is it makes us a family. Then the business kind of happens.

For Shark Tank contestants, it often feels like an American rags-to-riches story.

For all the entrepreneurs, it’s exactly that way, with the magic of Shark Tank sprinkled on top. It’s an amazing ride for each and every one of them. Even the ones who don’t succeed are thrilled with the ride.

You and Mark Cuban seem to have a good rapport on TV. Have you learned any entrepreneurial or business lessons from Mark in the years you’ve worked with him?

Mark is the smartest person on the set, hands down. Every Shark has their thing – Mark is people smart, which I think is my talent too.

He’s great with people, but he’s also great with technology. I don’t even try to know that space. So with Mark, that’s a double-header: people and technology.

With Mark, I did learn one thing that I use again and again. He said he never invests in a business [that features a large tech component] that is not run by a techie. And I’ve learned to do that too. I’ve learned that from Mark.

 

Find out more about Barbara here, and follow her on Facebook, Twitter, and Instagram.