Shortly after graduating college and bouncing around various jobs, Barbara Corcoran had an epiphany.

She compared the lifestyle of her hotshot boyfriend, who had his own real estate business, to the constant struggle of her father, who was a printing press foreman. The direction to take was clear.

She cofounded the Corcoran Group real estate firm in 1973 with her boyfriend, and after they went their separate ways, she continued to grow her reputation in the New York City real estate scene. Corcoran sold her firm to NRT Incorporated in 2001 for $US66 million and started to build her public persona on television and in print.

In 2009, she joined the cast of ABC’s reality pitch show “Shark Tank,” which soon became not only a hit series but her full-time job.

We spoke with Corcoran to discuss how her business philosophy has changed over the years and what it’s like being a Shark.

The following interview has been edited for brevity and clarity.

Business Insider: At what point did you realise you wanted to be an entrepreneur? Was that something you always had in you or was it something that developed over time?

Barbara Corcoran: No, no, no. Not at all. I was an entrepreneur in two different businesses — I had a flower of the week club first and then I had the real estate brokerage firm — but no, I don’t think I even saw myself as an entrepreneur.

It was a job, basically. When I started my flower of the week club, I thought, “Wow, I could make money early in the morning by delivering flowers before I even have school.” And then when I started the Corcoran Group, it was just ’cause my boyfriend at the time said, “Hey, you’d be good in real estate. Why don’t you start a company?” And I go, “OK, why not?” I didn’t aspire to it one bit.

My dad had a huge influence, though. Because he worked for someone his whole life and hated it. He was a printing press foreman, and he would constantly get fired for insubordination. Then he would take weeks to find a new job. He was a guy who didn’t like authority, period, from anybody. He’d tell his boss, “Go to hell, and your son goes to hell, too!” And get fired immediately!

He was a walking, talking example of insubordination, and I gotta believe that was an influence because nine of the 10 kids in my family are all in business for themselves. And that couldn’t just be a coincidence.

Most people that start businesses for themselves, I find, generally, when they do it at a very young age, they have parents who are in business for themselves, and that’s all they ever saw. So they assume they’re going to have a business for themselves.

BI: Have you had mentors who have taught you how to build a business?

BC: I’ve had two great role models. I had my mum, who was never in business. But in my household — which had two bedrooms, 10 kids, and one bath — you would have recognised her as a phenomenal businesswoman. She was just super organised, definitely in charge, had everybody doing what she wanted, motivated everybody. She was just in charge. And so her house was her business.

And then the role model I had as an adult, even though [my mum] kept proving to be the best role model honestly for business, was Ramone Simone, my first boyfriend who gave me $US1,000 [to start a business] because he was 10 years older than me. And he was building houses in New Jersey, that was his business, and he was a guy who was in business for himself. Everyone in my hometown, with the exception of my dad and maybe two other dads, worked for the aluminium company.

And so I never saw anyone who worked for themselves, really. But Ramone Simone did, and he had a big fancy car, and he had nice suits on, and he laughed, and it seemed like he had endless money. It was like, “Whoa, this is easy!” So when he said, “You’d be great in real estate. Why don’t you start a real estate firm?” [I was like] “Yeah, ok!” I mean, if he had said, “Why don’t you jump off a bridge?” at that impressionable part of my life, at 22, I would have leapt right off that bridge. So I was game for whatever he was gonna say.

BI: Was there a particular piece of advice that has stuck with you?

BC: Yeah. Again, I give Ramone Simone the credit for that. It was the early ’80s, when he left me to marry my secretary — which was a big downturn in my life. When I ended the [real estate] business and divvied it up into two teams, he picked the first one and I picked the second.

On the way out the door he said, “You’ll never succeed without me.”

He’d never said anything mean to me, but he was so angry we chopped up the business. And I wouldn’t have chopped it up, honestly; I’d have stayed with him had he allowed me to fire the secretary but he wouldn’t. And he was the majority shareholder, with 51%. I said, “I was the one running this business, doing the billing. How did you get in charge?” And it was because he had 51%. It was rough.

But that was the “advice” that got me through the thick and thin, mostly because it slammed me in my gut, and I didn’t want to let him have the satisfaction of seeing me go down. That’s what I always leaned on when things were bad. I’d be like, “Damn, I’m not gonna let him see me [like this].” And he probably didn’t care at that point. He had three kids with his new wife.

BI: What are some other insights or experiences that were critical to your approach to business?

BC: I saw a lot of examples of what not to do. I worked for a very short stint for two people in the real estate business, the Giffuni brothers, who were two elderly men who owned lots of properties in New York, and I was their receptionist. They were both extremely warm and loving toward their staff, so I felt very much at home and I didn’t want to ever leave them. I did, obviously, to start my own business. So they were very influential in a good way.

I needed to get a sales licence, so I had to work for someone before I could open a firm. I worked for another guy who will remain nameless, but he was a bastard. Everybody hated him but he owned the biggest rental company in New York that eventually went under. He took your spirit away.

It was my job to rent apartments in a specific building on 87th and 2nd, and I sat there all day and people would come in and I’d rent them an apartment. I rented five apartments in one week and people couldn’t believe I managed that because it was a hard-to-rent building by reputation. And he came in and he asked to see my sales sheet. And he looked down the sales sheet and I was aglow — I was like 21 years old and I was so happy — and he dropped the sheet on the table and he goes, “I say you’re just a piss in the bucket.” I was devastated. Like my world crumbled.

But you want to know something? In hindsight now, being an adult and looking back, that’s probably how he motivated people, by insulting them. That also worked for me with Ramone Simone.

So I think you learn more by how not to do things. I never had a star model to mimic, other than my mother.

BI: Something I found interesting on “Shark Tank” is the moment you got angry with the entrepreneurs who were the sons of the guy who founded Game Stop…

BC: Rich kids.

BI: You made a comment about never investing in rich kids. Were you caught up in the heat of the moment, or do you always look down on privilege?

BC: It’s not that I look down on it. It’s harder for a kid with privilege and successful parents, it’s harder for them to succeed if they’re going to be in business for themselves. I’m not talking about in corporate America or investment banking — all those connections play to your advantage, I think, along with education.

But what I do believe, and I truly do believe it, is that if you’re a rich kid and come from a family of privilege, it’s so much harder to succeed in your own business because you’re missing the most valuable card, which is called “need.” You don’t need to succeed. And so all your landings have been softened for you your whole life.

The best way to think of a solution in business when you’re slammed up against a wall is to try to think of five different solutions to get around it and keep going. But when you know that you have a trust fund, you know that you can always fall back on your parents, and you know that you can get additional funds, you get cheated out of thinking of those spur of the moment, very needy ideas that get you through.

So I do not invest in businesses owned by rich kids. I just don’t do it because I can’t get the taste of them. I can’t take a bite out of the entrepreneur and feel a tremendous pressure, and so I can’t identify with that. I like to work with people that I feel I can really align myself with, and I get them and they get me. There’s a great magic that happens there that you can’t fake.

BI: So the main thing you’re looking for in an entrepreneur is that need for success?

BC: Yes. And I another thing I must say I’m biased against is a well-educated entrepreneur. I’m going to tell you something: Everything in the education system encourages left-brain thinking, and the better the school (not always) and the better the privilege, where the crowd you’re hanging with is made of very affluent kids…

BI: Are you talking about MBAs?

BC: I’m talking about even undergraduates at really fancy undergraduate schools. I love the brainpower. You could see that the kid is so smart. But that generally doesn’t bring with it street smarts. I really want those kind of smarts. The kind on the street. Those are the ones that win in business.

BI: What is it like often being the only woman among the “Shark Tank” investors for an episode, or at least just one of two? Does that affect the dynamic?

BC: Well, it’s better having two women on the set, definitely. Because I was the only woman on the set for three years.

It’s much better having another female in one way because we have a camaraderie and can gang up against the guys, which we don’t often do, surprisingly. I don’t know why we don’t. I’m going to try to do that next season the best I can. It’d be good for the show!

What is interesting to me is that I’m very comfortable with men. I really am. I have no issue with it. I could usually manipulate a man much more easily than I could a woman, because they’re more vulnerable to manipulation from a female. They’re not expecting it.

I was in a man’s world. Even though you think of brokerage as a female business, it’s worked by women but owned by men. So everybody in my ballpark that I competed with, it was in a business owned by men and usually second or third generation. So I’m used to that. You can stick me with a bunch of men and I’m my best. If you stick me with women and I have to switch off from female topics to business, I’m not as fluid. I’m not used to it.

I also had four brothers, which helped, and I was older than all of them, so I pushed them around from the beginning. And so that was second nature to me, you know? [laughs]

The one downside from having another female on the set? I had a great advantage as a lone female Shark, which was I got a lot of the consumer products that the men just didn’t understand. They didn’t shop for food, they didn’t buy clothes for the girls. I’d say about 40% of what comes on “Shark Tank” is understood better by a female than a male. And so that was my little secret sauce, you know?

But now, of course, Lori [Greiner] has got a female and a very bright perspective, which is unlucky for me! I lost a little of my edge. [laughs]

BI: Of the investors, is there one you most prefer working with? In a recent interview, Mark Cuban said he most prefers working with you.

BC: It’s mutual. You know why? Because he’s buttoned-up, he does the due diligence fast, he closes the deals, he’s smart — not to take anything away from the other Sharks, who are smart in different ways — but he’s particularly smart in more ways, I think.

I’m smart in certain ways, but I know all the stuff I’m not good at. He seems to be smart across the board. And so, my odds of winning with Mark are better. More importantly, I like efficiency. So if a deal’s gonna happen, it’s gonna happen. Boom. Done. And he’s cut from the same cloth. Whereas the other Sharks, I think they take a lot more time and are more thoughtful, more cautious in their deal making.

BI: In this season, was there a moment that got particularly heated or emotional that you can take us behind the scenes of?

BC: There’s this one coming up where two women ball their eyes out. I thought they were gonna take a stretcher and haul them off. And they cried so much, I thought for sure it wouldn’t air, and it is airing.

I’m like, geez, how did they edit that one down? I hope they took their 30 minutes of tears and cut it down to like a 10 second clip! But I don’t know how they’re going to do that, because even in their pitch, they’re weeping.

Ay, ay, ay! If they weren’t going to be taken out of there, I was going to be taken out. And I bought them. Not because of the tears, but I had to listen between the tears to really get what the heck they were talking about.

So there you have it: weeping women. Not my favourite, but this will hold the record for the most weeping women in an episode. [laughs] I still can’t believe I closed on that.

BI: Do you think you got wrapped up in emotion with that deal?

BC: Never. It’s a great business and I’m very happy. They’re solid entrepreneurs.

Usually when anybody starts crying, female or male (and I’ve seen more men cry on that set, by the way), I would have to say that turns me off totally. I get a little embarrassed for people.

How I got over that one, I don’t know. I’m going to have to see the episode and tell you after the fact why I went forward! [laughs] It doesn’t sound like my style at all.

Corcoran with Pipsnacks founders (and siblings) Jeff and Jen Martin:

 on

BC: Oh, definitely. Already I can tell you it’s Pipsnacks. They’re two kids out of Brooklyn, a sister and brother. They’re terrific. They’re both in their own right phenomenal entrepreneurs. And they’re together! Do you know how exciting it is to get two for the price of one? Usually you have a winning entrepreneur and a sidekick who’s a quanter [numbers person]. Or you get the quanter running the show and the sidekick has to be pushed up above them, and that’s tricky business. I’ve had to do that. When you have two rock solid entrepreneurs, each with talents that are also complementary to one another, that’s the trifecta, three for two.

BI: What do you think was the best pitch on the show?

BC: The best pitch that always comes to mind is Cousins Maine Lobster. Those two guys, again, are two phenomenal entrepreneurs. They’re like Pipsnacks.

I love getting two phenomenal entrepreneurs at once. They don’t come up so often, but when I see them it’s like I’m drooling but I keep my mouth shut so I’m not dribbling all over myself.

But the best pitch to date, even through this season, was clearly Cousins Maine Lobster. Because they were clear, they were good-looking (you couldn’t take your eyes off them), they were high energy, and they answered every question and objection like geniuses. Genuine, rock solid, and perfect answers.

I remember thinking to myself, “My God, these guys are amazing!” And you know why they answered everything so well? They were smart enough before they came on “Shark Tank” — I haven’t seen it before and I haven’t seen it since — they watched all four seasons of “Shark Tank” before they came on. They role-played. They worked on every objection any Shark had ever asked an entrepreneur. Reams of paper. And they practiced the answers.

You want to know the one question that none of us thought to ask when they were on that set? It was “How long have you been in business?” All they said was, “Sales this month are the highest ever,” and nobody asked, “Of how many months, or years?” And we always ask that. But they were so buttoned-up that none of us thought to ask that.

It wasn’t until I did my due diligence that I found it was just three months. But that’s how solid they were. I thought they were seasoned businessmen.

BI: What about the worst pitch?

BC: Oh, there are so many different ones, who do I pick? Very often the worst pitch is the most interesting, also, I have to tell you. Because you can’t believe this person’s doing this.

Of course, there’s the guy with the Bluetooth device that you surgically put down your ear canal. And then if it runs out of battery you have to surgically remove it and change the battery. He was an engineer, dead serious — tight lips like a military guy. That was the worst pitch. I think if you ask the other Sharks they would agree.

But then you have the wacky dentist whose toothpaste put you to sleep at night, the chubby lady who said her lipstick makes you lose weight… I mean, the claims we hear on there, they’re laughable.

Or maybe this one rivals the Bluetooth engineer — a Rhodes scholar, his thing, and he had charts and film to prove it, he would turn seawater into pure gold. Would you believe that? He was at least friendly. He wasn’t as scary as the Bluetooth guy. He smiled a little. But crazy things. They keep it interesting.

BI: What are you working on now? How do you balance it all?

BC: Well, my real estate investments I stopped making probably seven years ago, believe it or not. I always bought properties, four- to six-unit buildings that were up and coming. And that’s the investing that I had done over the years. And then in New York you start to look like a genius because they all accrued so much value.

But I haven’t done that. I have no time. I thought ["Shark Tank"] was a side gig but it’s not. It’s a full-time gig. Because it’s not just the shooting schedule of the actual episodes, you then have the updates, and then we’re flying around for the [upcoming spinoff].

How do I balance putting my eye and nose on what’s important and dropping the rest with my entrepreneurs? I have such a simple system.

I close on the corral of business that I do for the season — this season I closed on five deals. I’m like a bunny rabbit with each entrepreneur for Skype calls, or in person if they’re within shooting range. I help them with everything they do, I make to-do lists, I make sure the follow-through is there. I do that probably four months straight.

And then I decide who the winners are.

After I sign a deal, I have everybody send me a photo of themselves. I frame it and I put it on my wall. After that four-month period — it used to be six months, now it’s four, and I think I’ll make it shorter — the minute I realise they’re not a great entrepreneur, I flip the frame over. I keep the frame on the wall, but this way every time I look up, it’s my symbol: Don’t spend any time on this. I put all my focus on my good ones.

Because each season you pick up more and more and more. You can only really put your efforts into your winning horses, your best bets.

BI: How many businesses are you invested in now?

BC: You know, I’d have to count the photos to be exact, but I’d say about 26 or so. But ask me how many are right side up on my wall. That’s the key question. I’m actually looking at the wall. Let me see. Yeah, there are exactly nine. Nine are up right now, and I’m sure I’ll flip a couple over in the next couple months and be back to seven. [laughs]

Follow Business Insider Australia on Facebook, Twitter, and LinkedIn