The Tim Ferriss Show Transcripts: Barbara Corcoran — How She Turned $1,000 into a $5B+ Empire: PR Stunts, Sales Techniques, Critical Early Wins, Fighting Trump, and Becoming a Real Estate Mogul (#725)

Please enjoy this transcript of my interview with Barbara Corcoran (@BarbaraCorcoran), an investor/Shark for the past 15 seasons on ABC’s four-time Emmy-award-winning show, Shark Tank, investing in more than 100 businesses to date. 

She is also the founder of an eponymous real-estate company, which she started with a $1,000 loan after leaving her job as a waitress in New York City. Over the next 25 years, she would parlay that $1,000 into a $5 billion real-estate business. Barbara is the author of the national bestseller Shark Tales: How I Turned $1000 into a Billion Dollar Business and host of the top business channel on Patreon, Barbara in Your Pocket, which provides exclusive content created for entrepreneurs at every level.

On Patreon, Barbara will dive deep into the topics most important in business today, give an inside look at how she runs her business and works with her Shark Tank companies, and join members live to answer their toughest questions.

Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

Listen to the episode on Apple PodcastsSpotifyOvercastPodcast AddictPocket CastsCastboxGoogle PodcastsAmazon Musicor on your favorite podcast platform. Watch the interview on YouTube here.

#725: Barbara Corcoran — How She Turned $1,000 into a $5B+ Empire: PR Stunts, Sales Techniques, Critical Early Wins, Fighting Trump, and Becoming a Real Estate Mogul

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Tim Ferriss:
So I thought we would start, Barbara, with your fake funeral, because I would love to know, for your 70th birthday, how did you decide to have this funeral rehearsal, effectively? How did that happen?

Barbara Corcoran: It was a competition with my friends. I overheard two friends were planning a birthday party to me as a surprise, and they didn’t know I knew, but I don’t like surprises. I like it when I give the surprise. So I immediately kept thinking, “I’m going to surprise them. I’m going to surprise them with my own surprise.” And then when I gave it some thought, I tried to think of the most absurd things, and the most absurd thing was to kill myself and have my own funeral. It just seemed like the right thing to do, because I knew it would have great shock value and I love to shock people.

Tim Ferriss: You do love shock value.

Barbara Corcoran: So I planned it, but I took other two other good friends into my confidence who could keep a secret. So we switched the party. They thought they were waiting for me to come into the house upstairs in my apartment. It was a great memory of it. And I was really downstairs, waiting in the coffin. And then my good brother told them, “Hey, she’s coming in downstairs, hurry down the stairs.” They all came charging down the stairs. I guess I had 85 people there, and they walked into a funeral, and the guests, I mean, if it had ended there, I would’ve been satisfied, because the guests were — I could hear it with my eyes closed. They really thought I was dead.

And then they came up and paid my respects, and I had the rabbi give the last rights or whatever he does in the Jewish faith. And the minister, they’re both phony friends, but they were dressed for the occasion. And I got to hear what everybody said about me before I was dead. And I thought, “I’m probably the only person on Earth who actually is hearing about it before I’m dead.” So I loved it. And I had a beautiful gown, I looked the part, I was gorgeous. And so my final day was really a beautiful day.

Tim Ferriss: And I think there was, am I making this up, that you hopped out at one point and then started dancing the tango? Is that right? Something like that?

Barbara Corcoran: Yes, of course.

Tim Ferriss: Of course, the tango.

Barbara Corcoran: I had taken lessons. I had taken lessons for four weeks. I had a beautiful gown with a tall slit, red, I looked gorgeous. And when I kicked my leg up, I had practiced that move, I could kick my leg and hop right out. And then we started the dancing, and that was a dance party. We had a ball.

Tim Ferriss: Incredible, incredible. You really seem to have a knack and obviously an enthusiasm for shock value and PR stunts.

Barbara Corcoran: Yes.

Tim Ferriss: Getting press has been a superpower. And in the early stages of your business, certainly that was the case and continues to be the case. Where does that come from? In the reading and research that I did, I couldn’t quite figure out if that was you out of the box as a little kid. Where did that interest in buzz, and PR, and the knack for that come from?

Barbara Corcoran: Honestly, from my dad, you hadn’t met my dad, you would’ve known that, he was the king of fun. He worked two jobs his whole life, so he killed himself for his family. But on Saturday and Sunday, he was our playmate and he would think of the most irresponsible things to do with us. We had 10 children, and he was the most popular dad in the whole town, because he would put us on a wooden lattice, shove us down the side yard, over retaining wall, into oncoming traffic. He thought that was exciting, and it was.

Tim Ferriss: Surprised you didn’t have your funeral earlier, yeah.

Barbara Corcoran: Yeah, but he would put a twist on everything that would just make everything fun for us. So I realized the importance of fun. I mean, people just don’t have enough fun. I’m sure I’m everybody’s most fun friend, and I like that, because I think it’s so worthy to introduce fun, and joy, and memories into people’s lives, whether you’re at work or whether you’re at home. I think about it afterwards and I get so much satisfaction out of it. Even some days I think to myself, “Well, if I die today, I’d be happy, because I really had a good time last night,” but I didn’t plan on dying, yeah.

Tim Ferriss: And as I was trying to deconstruct, let’s just say the first five, 10 years of your business, and we’re going to talk about things that preceded that too, the 22 jobs and so on. And I’ll just bounce around, because it’s my curiosity that I’m chasing here. But your ability to storytell, it strikes me that you’re very good at people, you’re very good at systems, you’re also very good at positioning and storytelling. Is that also from your dad or was that a trained or learned skill on some level?

Barbara Corcoran: That’s an Irish trait. It’s called Irish bullshit. Talk to any Irishman, he can usually throw it around. I don’t think that’s a special trait at all. But why I like stories is people remember stories. You could lecture, you could share experiences, and people will like it for the moment, but they won’t repeat them nor will it resonate with them. Just like the old Indians probably sat around the fire and told stories, same kind of thing. And also, I was in the sales business, remember, and in sales, telling a good story is powerful.

The PR that I did for my real estate company were old stories, creating a story that people would be curious about, to pull them in. And so it always had a great, spectacular beginning or a hook. I always used think, “What hook could I use, what hook?” And then I would develop a story quickly. And that’s why I also think I did so well with the press, building my business, because of the storytelling.

Tim Ferriss: What were some of the hooks or early wins in the press for your business? Because in the beginning, my understanding is you’re basically competing against this old boy network, but they’re complacent, and they’re accustomed to doing the things the way their father or grandfather did it. And so you had certain advantages in terms of speed and so on.

Barbara Corcoran: Yes.

Tim Ferriss: What were some of the early wins in terms of press or early hooks that you used that seemed to really work in the beginning chapters of that business?

Barbara Corcoran: There were many, there were so many hooks, little hooks, big hooks, some that didn’t make money immediately but wound up making money and some that made a lot of money really fast. I think probably my first stunt was when I got my first big listing, which was — I don’t even remember who owned it now. Some famous guy had a ton of money and he owned the top floor. He had to sell the penthouse of the Galleria. Oh, Stewart Mott, that was his name. Mott’s Applesauce. Lots of money. Nobody could sell the damn thing. It was too big, too expensive, it wasn’t even attractive. And he had cows on the roof. So he thought the story might be that, “We have cows grazing on the roof,” which could have been — but what the story I developed was I figured out what the maintenance was per night and I asked him how often he slept there, because rich people have multiple homes.

He said, “Three nights, three nights, maybe four nights.” And I divided the maintenance by that and my headline was, “Uh-uh, live in this apartment.” And the picture was all over the place. “It will only cost you $80,000 a night to put your head on the pillow.” And people were fascinated. People would spend that money. I think right after that, I then got a very good listing because of that, because one thing leads to another in the real estate business, and I got the Guggenheim Mansion. Nobody could sell it. It had never been touched. It was a dump, a real dump in the most expensive block in town. I couldn’t even get anybody to see it twice. And so then I discovered a safe in the basement. I said, “What’s in that safe?” And they said, “We don’t know. We haven’t opened it.” So I invited The Today Show to come over for the opening, and they filmed it and we opened it, and there was nothing in it, but who cares? There was so much suspense about it that I sold it, like, within a week.

We had so many celebrities come to see it. They just were enamored with it. That’s a story. Those are early hits. And then I just started churning out, churning out any kind of bullshit I could think of, really. And people usually went for it. One of the most fun things was when the boards in New York, the stuffy boards, announced they were going to interview dogs before they let them into the building. I thought it was preposterous, but the very following day, I had all my salespeople bringing their dogs to Central Park. I invited The New York Post and I taught dogs how to shake hands, like 500, “Shake, yes,” and it was a great picture, so I knew people would go for it. Did that sell apartments? No, but it put my brand in front of everybody’s face and made the old boy network go crazy, which was half my reason for doing things, to compete, to show them that I could think of things I could never think of, you know?

Tim Ferriss: Definitely. And as one of 10 kids, I’ve heard in other interviews that you’ve mentioned you learned how to compete, right?

Barbara Corcoran: Yes.

Tim Ferriss: And you learn a lot of social dynamics in that environment. And I’ve been trying to study what differentiated you from your siblings, in the sense that what were the contributors to your later success? One certainly seems to be your experience with dyslexia. Are there other experiences or innate differences that you feel really differentiated, ultimately, the trajectory that you took from your other siblings?

Barbara Corcoran: Definitely not innate, I don’t think, but taught or brought out by my mother, definitely. My mother would decide what each child’s gift was, and we had a role in the family, so we weren’t just 10 kids doing the same thing. We all had a job. My job was to entertain everybody. My mother said I had a wonderful imagination. I could think up games. She would always push me like that, the chalk was in my hand, not in a sibling’s hand. On the rainy days, I was in charge of entertaining the kids. So I think my mother’s belief that I was very creative, and she always told me, “You’re so creative, you’re so creative, you’re so good. You know what to do.” I think that gave me the role that I got. And then I practiced, I mean, not every day of my life, but constantly. I had to entertain kids.

And so I think I just grew up with great confidence that I had the ability to do that, because I could do it really well. I mean, if you were to walk into Edgewater, New Jersey when I was eight years old, nine years old, 10 years old, every kid in the neighborhood was playing in front of my house on the street, because I was able to draw extravagant snail games that went on for like a block and a half. To win the game, you had to go for a block and a half with the traffic going by. 

Tim Ferriss: What is a snail game? What type of game is that?

Barbara Corcoran: I don’t know if I invented it, honestly, I don’t remember how it came to be. It’s like a very sophisticated hopscotch board. Instead of having a straight line, I made it in circles, wounding, wounding, wounding, wounding. You couldn’t see where you’re going. And on certain spots, I had two feet, another spot, I had one foot, then another spot, I had two feet, one hand, another spot, I had no feet. You had to really jump to get over it.

And I always used different colored chalk, and it made it exciting, so people would cheer for the kids. It entertained us for years, my snail games, and if it was a rainy day, I would make board games at home. And my brother to this day says, “I wish I had those board games. I would’ve made a fortune if I had produced them.” I said, “I don’t think they were that good, Tom. That’s your memory.” But my mother was responsible, definitely. Moms are powerful creatures, as you know.

Tim Ferriss: Very powerful.

Barbara Corcoran: They can make you. My mom was a maker, thank God. God bless her soul.

Tim Ferriss: And it seems like that would also be, on some level, a tremendous confidence builder — 

Barbara Corcoran: Yes.

Tim Ferriss: — in combination, then, with starting work as early as you did, with school being difficult with the dyslexia, and then building confidence through work. If we look at that period of work, before you start your company, and I guess there was 22 or some odd jobs, I’ve heard you discuss service jobs, waitressing before, and I worked in restaurants for a long time as a kid, busboy.

Barbara Corcoran: Then you know.

Tim Ferriss: I think everybody should do it. And I’m curious if you could maybe take a second just to say what was so critical about that particular job in terms of what you learned, but also what second place might be. So outside of the waitressing, in terms, of learning, things that contributed to your later success, is there a second place type of job that really helped you?

Barbara Corcoran: And I don’t even think of it as first, second place. Honestly, every job I had, I learned something new on, and that’s what I wanted to do, I don’t think consciously. But my first job, when I was 11, as a playground supervisor, not a very big job, no doubt. But I watched four kids in the morning for three hours and played on the playground. But I’m thinking, “This town is filled with poor kids. Where are the kids?” So I took my kids and I sent a letter to The Bergen Evening Record, the local paper, and I said, “We have kids here coming for breakfast.” “Breakfast with Barbara,” I titled it. “Breakfast with Barbara,” I was 11. I had to have somebody else write it for me, because I couldn’t write, but I sent it out to the reporter, and they sent a camera down. And after, “Breakfast was Barbara” was in The Bergen Record.

I had close to 40 kids show up every day. And I realized my very first job, the power of the press, I never forgot that. But sales jobs, I learned so much in talking on my feet, I learned I could talk to people. I could get them to see things the way I saw them. So I would say, “Imagine if you had this granny dress at Schweitzer’s Department Store. Imagine if your kids had it. They could play house all day, they could blah, blah, blah.” And people would see it through my eyes and they’d buy one.

So I learned everything in my jobs. Nothing at school — not a damn thing at school — but I learned everything in my jobs and I found my confidence there, and I also found out what I wasn’t good at. I wasn’t good working for a bastard. If there was a really mean, cheap boss, I quit. After a while, I just wouldn’t take it. I was no good as a secretary. I couldn’t type, even though I lied to get the job, said I could. I couldn’t take steno well, even though I said I could, I would get fired. And so I really learned that I had a narrow, narrow piece, that I was good at selling, hustling, and PR. And so I came out, I got that early. How lucky you are when you have jobs as a kid, how lucky you are to hustle and get your real education. That’s the real life, you know?

Tim Ferriss: For sure. I would add another superpower, in so much that I’ve seen of you and heard and watched, the one thing I have never seen, and maybe I’ve just missed it, but I have never heard you take a victim perspective. And I have heard you say, for instance, that the difference between successful people and others is how long they spend feeling sorry for themselves.

Barbara Corcoran: So true.

Tim Ferriss: I’ve also heard you say, and I’m paraphrasing here, so if I get it wrong, please correct me, but that you are at your best — 

Barbara Corcoran: So far, you’re right, Tim.

Tim Ferriss: Yeah, that you are at your best when you’re being talked down to by a man, or something like that.

Barbara Corcoran: Definitely.

Tim Ferriss: And you take — and I would love for you to perhaps tell the story of your 51 percent partner in the founding of the company, but also I’m so curious where that resilience and ability to reframe what other people could take as victimization, and turn it into something to your advantage, because I’ve seen that over and over again in your story.

Barbara Corcoran: It’s such an important part. I mean, recovering from failure, in my book, is 95 percent of life. If you’re going to have a good life, you’d better be really good at getting back up, like a jack-in-the-box, boom, boom, boom. Just get back up. Get back up. I think I got that, honestly, by being dyslexic, because when you’re the kid in class that’s dumb, you’re a failure by anybody’s standard, and you’re constantly put down or looked down on, and I was embarrassed. I learned shame in the classroom. Terrible thing for a child, to feel like a nobody just because they don’t have a certain skillset. But that definitely taught me about — I had to go to school every day. I had to go back, and sit there, and hope they didn’t call on me for reading whatever. And I got used to being a loser like that, and getting back up, and I just had to go to school.

So I got early training in that area. And I also learned, from running salespeople my whole life, that really was the only difference between the superstars that I had making two, three million dollars a year and people who made an average of 45,000, which was the norm. How does a superstar do it? I became a student of that and I really did. I used to think it was connections. I would hire for that work ethic. I would hire for that, who did they know in real estate, high-priced real estate? I would hire for that.

And then I realized that’s just a starting gate. It gets you in easy, but when it comes down to it, it’s how well you get back up and how long you take to feel sorry for yourself. I admired, they drove me crazy too, but I admired my superstars so much because of that ability. I could see them, like you could punch them around. They’d go, “Ha ha,” get back up. And so I learned from them too, you see. But I don’t know if I answered your question, Tim. I think I got a little lost in that answer.

Tim Ferriss: You did.

Barbara Corcoran: Yeah, okay.

Tim Ferriss: I think you did answer it, and I think we’ll probably end up expanding on it a little bit. To give an example from earlier, would you mind describing the founding of the company, and your business partner, and how that came together? Just to give people a little bit of context. If they don’t have it.

Barbara Corcoran: Yes, of course. I was waitressing when I was 17, at the Fort Lee Diner, which was above my house, a middle class town, which I thought then was a rich town, but it’s really just middle class by comparison. And one night, a man walked in and I looked at him. He had olive skin, jet-black hair, aviator shades on. You couldn’t really see his eyes, and a real suit on. I had never seen a man in a suit in my life until that night. Nobody wore suits even into the diner for dinner. I looked at him and I thought, “I’m going to lose my virginity.” One look, I knew I was going to lose my — 

And I did, that month, and I knew it would be within the month. But anyway, his name was Ramon Simone, and he convinced me, after a month of driving me home at night, which my parents didn’t like at all, but he convinced me to go to New York City. He said, “With your personality, you should really visit the city. I’m going to pay for a week at the Barbizon Hotel for Women.” I’d never heard of that. I had never visited New York City.

Tim Ferriss: What is that?

Barbara Corcoran: It was the only hotel left in New York that only leased rooms to women. No men were allowed. So it was respectable. It’s now a Reebok club, of course, many years later. But my mom accused me of being a prostitute. I wasn’t.

Tim Ferriss: Your mom did?

Barbara Corcoran: I knew I wasn’t. Oh, yeah, “Let a man pay for your hotel?” And I was going to New York City and leaving our home. Oh, not a good thing. Okay, but he gave me $100 to buy my new first New York outfit, and then I was wondering if my mom was correct, but she still wasn’t. I could tell. I was just taking the 100 to get a new outfit, but let me make a short story of that. That’s so boring. The key part is he gave me the $1,000 to start my business, and he said he would take 51 percent of the shares and I would take 49 percent, because he was the founding partner and I was the operating partner. And I said, “Sounds like a deal.” And off I went running.

About seven years later, when we had a rental business, we had, I think, 14 agents at the time, renting apartments all around Manhattan. He came home one night and I was making pasta for his three kids, who I became their mom and he said, “I’m going to marry your secretary.” And I couldn’t believe it. I thought I was hearing things. “That bitch,” I thought in my mind, but I said, “Tina?” And they were married within seven months. It just broke my heart.

But more than broke my heart, it really broke my confidence, because remember, he had found me at a diner. He taught me I could have my own business. He loaned me the money. He took me out of my hometown. He was a man 10 years older than me. He knew his way around the world. So all of a sudden, that’s gone. My legs were taken out from under me, and I thought I couldn’t live the year, almost, is how I felt at the stupid time. What a waste of energy. Anyway, just about a year later, I think I was finished off on a Thursday, watching Ray and Tina in my old office together, holding hands and making eyes. It broke my heart.

So the very next morning, I arrived and I said, “We’re ending the business today, Ray. We’re going to cut it in half.” I said, “You pick the first person, I’ll pick the second, until we have them cut.” And five minutes later, I took my seven people and I said, “Guess what? On Monday, we’re going to move.” “Where?” “It’s a surprise.” And it was a surprise.

But in those days, Tim, honestly, you could get a phone installed on a weekend, a great advantage. Ma Bell came on that weekend, installed phone lines. I had a landlord who rented me the 11th floor, which was just like our previous eighth floor. So I had a space to open it, and I was able to buy all my desks down on 42nd Street. And the guys ran it up to Midtown, put it in place. It was a different world. But on Monday, I was open for business, and that was the Corcoran Group. That was the first day of the business, and I named it the Corcoran Group, because I knew with my cash position and acumen, I was going to need a lot of help from the group to make it to the finish line, you know? Yeah.

Tim Ferriss: So I’m going to pick up on that very briefly. I have two follow-up questions. One is related to the landlord, but before I get there, I was listening to Diary of a CEO, your interview on that show, which was excellent. And in the course — 

Barbara Corcoran: Thank you.

Tim Ferriss: Absolutely. It was very vulnerable, very powerful. And one thing stuck out to me that I wanted to ask about, and maybe it’ll be a dead end, but when you were describing the — I suppose, I don’t want to say betrayal, maybe that’s a strong word. Maybe it is an appropriate word.

Barbara Corcoran: It’s life.

Tim Ferriss: Yeah, it’s life. But what you said that struck me is, “I don’t blame him.” Something like that. And I wanted to ask you if you meant that or if you could say a little bit more about that. And this comes back to my perception that you very rarely take the victim perspective. You use it in some way. But I’m curious what you meant by that when you said, “I didn’t blame him?”

Barbara Corcoran: Well, you have to realize Tina was five years younger than me. I was 30 when he left me. Tina was 25 or so, prettier than me, much prettier, had long, blonde hair. She was far more feminine than I ever was, and she was quiet and she adored Ray. So how could you blame them? They fell in love. They had three children together after they were married. I mean, they were clearly in love, but I couldn’t blame them. I mean, I would’ve fallen in love with Tina myself if I was Ray, probably would’ve helped him out the door, you know?

Yeah, no, I didn’t have a grudge, honestly. I mean, I was tremendously hurt, as we all are when we’re rejected. And I was at the age where I was thinking I should start getting serious about marriage, but I didn’t have anybody. So I had that moment where I was hurt, but I didn’t blame him. No, no. He did the right thing. He did me a great favor. Without him, I wouldn’t have gotten started. Probably, I would’ve found some other sucker to give me $1,000, I don’t know. But he was there, the one that did it. Yeah.

Tim Ferriss: Now, you were good at spotting talent, and we’re we’re going to come back to that point. What do you think it was that Ray saw in you?

Barbara Corcoran: Enthusiasm.

Tim Ferriss: Enthusiasm, what type of enthusiasm? There’s so many different species of enthusiasm.

Barbara Corcoran: I was a happy girl. I saw the bright side of things, which I have always done. My whole family was pretty positive. I had good positive role models, but I was highly enthusiastic, very talkative. It wasn’t my first job, remember, when Ray met me. He couldn’t look at me and realize I had been working since 11, and I was comfortable in my skin. I was flirting with the guys at the counter to get the bigger tips, because that’s how you get bigger tips. I knew the ropes, so to speak. I looked like a young girl. I wasn’t so young inside. I think he saw me as a fresh, happy person who wasn’t shy, and I made him happy. He was a bit of an introvert himself, a little bit of darkness in him that I didn’t have in myself.

Tim Ferriss: Yeah, so he wanted something to offset that, counterbalance it?

Barbara Corcoran: Yeah, we were pretty opposite. We were pretty opposite in that way, yeah.

Tim Ferriss: The landlord you mentioned who I guess gave you a floor, was that, and I might get the pronunciation wrong here, but was that Johnny Campagna? Or was that someone else?

Barbara Corcoran: That was John H. Campagna.

Tim Ferriss: There we go, John H. Campagna.

Barbara Corcoran: He always pointed that out. Yeah, John Campagna. Now, here’s a handsome man. Wow, was he handsome.

Tim Ferriss: So how does he fit into the story?

Barbara Corcoran: He did me a great favor. I had two roommates on East 86th Street, and I was operating my first business out of my apartment, as so many people do. And it’s another story, I won’t go on a different road, but I got lucky, in that somebody called me one day and I could smell the person on the phone wasn’t who they said they were. I could just feel it. And as it turns out, that lady posing as a customer represented the largest relocation company in New York. And I sensed something, and I gave her a dog and pony show all day, like the perfect agent in New York. And she fell in love with me, and she gave me all her business.

She said, “You know, I’m not who you think I am.” I said, “Oh, really?” I knew she was somebody else. And then she started shoveling me business. So as a result of that, getting back to John H. Campagna, she started shoveling all these young people from Citibank, young guys, and I would meet them in my apartment and show them apartments. I said, “Come to 86th Street.” It was turning over pancakes. They would come in so fast at me, and so I was showing them apartments. I had my routine, raking in the commissions, and that was going on probably for three or four months. And then Mr. Rock, the super, reported me to Mr. Campagna, the landlord, that he had a prostitute in the building.

And I get it, because I had spent my first check on a brand new coat at Bergdorf Goodman, my first commission check, $340, and I looked like a fancy lady. I knew it. And so I got eviction procedure. I found a note on my door, big red print. They put, it’s really a public embarrassment, “Eviction notice for prostitution.” But why I say it was a favor, I knew I had paid my rent. I knew I was quiet. I thought it maybe it was a mistake. But then when I thought about it, I thought, “I bet he thinks I’m a prostitute because of all the guys in the apartment all the time.” So I went and visited him in his office, and he was very buttoned up, did not like me when I walked in. I explained that I was not a prostitute. It took me a while to realize that, talking to him, “You think I’m a prostitute? I was almost a nun. I’d be the last person to be a prostitute.” He was Catholic, fortunately, knew what a nun was.

And then I explained to him how Mr. Giffuni, on the next block, another Italian, I did it on purpose, was renting his apartments like hotcakes. But I knew Mr. Campagna had eight empty, and I said, “He’s renting his apartments like hotcakes, because I was smart enough to tell him to build a wall in the L-shaped living room and call it a one bedroom and den. So he’s renting the same square footage as you for $40 more a month than you are getting on your plain one-bedroom.”

It was the idea I had for Mr. Giffuni, and I shared it with Mr. Campagna. He said, “You have the listings in all my apartments.” I got it. I didn’t even think of it as a sales call. I thought of it as a defense call. But I left that building, he fired his agent, who he had worked with for years. I can’t recall his name now, but I became his exclusive agent. And that was the first real exclusive agency I got. And so it was so easy with his listings, because I could get the city bankers in my apartment, go in the elevator, and rent them an apartment. Easy-peasy. So that was a fortunate happening, fortunate happening. I didn’t expect to land that way.

Tim Ferriss: So then you end up with the founding of Corcoran Group and you know you’re going to need some help.

Barbara Corcoran: That’s Ray and Tina. Yes, definitely.

Tim Ferriss: Right, exactly. And you’re going to need help. But I would imagine it was perhaps challenging to recruit in the beginning. Maybe I’m wrong, but I’m wondering what the key was to getting people you thought could be successful to join your company in the early days. What was the pitch? What was the trick?

Barbara Corcoran: Well, I had a great gimmick, two great gimmicks I used. When I advertised in the want ads, I would never put, “Position open, salespeople wanted.” That’s what everybody put, “Salespeople wanted, salespeople wanted.” I made my caption in double height, I used up my lineage that way, “One empty desk.” Rare. People want what they can’t get, you know? And so people would call on the one empty desk, but I didn’t say, “Make high commissions.” I didn’t even address the money piece. I put, “Join a company that’s a lot of fun, and cleaning up, and having a blast.” I just trimmed up our team that we had, which was true. I wasn’t exaggerating on that, but it brought in a lot of calls.

Then, when I was opening up a much bigger office and needed to hire like 15, 20 agents at once, I had even a better gimmick. I put, “Learn everything you want to know about real estate, career night.” It sounds common now, but then they’d never heard of career nights. Nobody did them. And then as the 40 people would come into my career night, I had a pencil on one hand, a pen in the other. And if they looked good, I gave them a pen to sign in. 

And then I dog-and-pony showed them, made them fall in love with me, putting on my charm in every way. They all wanted to work for me. And they’d call me the next day. I’d say, “If you have any interest, call me tomorrow.” And when they called, I would just see if they were in pencil or pen, and I know who I wanted to talk to.

Tim Ferriss: That’s amazing.

Barbara Corcoran: So I would talk to maybe 30 percent of the people that were at the career night, and invite them in for an interview. And then I would try to figure out if they have the capacity to sell, which is no easy feat. It’s hard to recruit salespeople, very hard. Very hard to recognize the talent that you need to do it, yeah.

Tim Ferriss: Did you view being a woman in that business at that time as an advantage, a disadvantage, a mixture of both? How did you think about that, if you thought about it?

Barbara Corcoran: Well, I have to say, when I walked into my first Real Estate Board of New York meeting and didn’t see a woman in the room of the business owners, I was a little intimidated. But when I tried to talk to the sons of rich guys, that’s basically who the trade was owned by, they didn’t work very hard, they were cocky. I spotted the cockiness and I knew I could beat them at their own game. It’s a weird thing about cockiness. It’s a blinder. Like, “I’m cool, I’m cool.” But they’re never looking or hungry for other things. I was desperate, not only hungry, I was desperate to even get a first sale under my belt.

It was an advantage, it was an advantage, because I could then walk into the rooms and I always wore short, red skirts with my jackets, and I had great legs, and I knew it. And everybody would turn to look at — because a girl stood out. You didn’t even have to be special. You just had to be a girl, and you were different. But as competing with them, I never saw myself as a woman. I never saw it as a disadvantage or a real advantage. I saw myself as a competitor, just a competitor. And boy, if they treated me badly, or spoke down to me, or didn’t give me any credence that I could possibly make it in their world — they thought I was a passerby. I would say to myself, “You just wait, I’m going to become your biggest rival.”

I knew that right from the beginning, because I was very competitive by nature, and I hated the insult. It was like, “Send me back to second grade where the kids were laughing at me.” It was too raw. Even though I was much older, it was too raw. And so it fired me up. It was the best thing in the world. If I had walked into a world of women all competing, also all being good, I don’t think I would’ve been very successful. I think the men helped me. I just had to show them I knew what I was doing or would learn what I was doing, yeah.

Tim Ferriss: So you had this attitudinal advantage, right? You had this competitive drive.

Barbara Corcoran: Tim, let me stop you for a minute. I have to say, you are wonderful interviewer. I’m shocked at how much you know about me. It’s almost intimidating. No, really. Nobody takes the time. Good for you.

Tim Ferriss: Thank you.

Barbara Corcoran: Over prepare for sure, yeah.

Tim Ferriss: Yeah, thank you so much.

Barbara Corcoran: I’m sure you’ve heard it before, but I add my compliment. Okay, start again.

Tim Ferriss: Thank you, I really appreciate that.

Barbara Corcoran: I mean it, very much. Yeah.

Tim Ferriss: Thank you, thank you. I take it seriously. I enjoy doing this, and I also value your time — 

Barbara Corcoran: It shows, yeah.

Tim Ferriss: — so I appreciate it. So you had this attitudinal advantage. You had this competitive drive. You also later became very well known for systems. And I’m wondering, as someone with dyslexia, what did you do differently? Because you’re in an information business. On some level, you’re in a people business, but you have to handle listings, you have to handle, I’m sure, plenty of written material. What types of rules or systems did you have in place for yourself so that you could function at a high level? How did that work?

Barbara Corcoran: I don’t think dyslexia eliminates the ability to organize. I don’t know. I’ve never read about it. I got my organizational system for my mother, who ran our two-bedroom house like a bootcamp. You know, everything had its place. Anything she had to repeat, she made a system for. If she had to polish our white buck shoes to go to Catholic school in the morning, she used a thick paint brush and painted them on a radiator, turned them over to dry, painted the other side, and even painted the radiator white after a while, when she realized it was dripping on the silver radiator. She painted it white to get rid of that problem. Everything my mother approached, she approached that way. So everyone in my family, my nine siblings and I, grew up very organized, very organized. We knew what organizations was. We were part of her system.

And so I made my salespeople part of my system. I just mimicked my mother in every way. But as a dyslexic, you have a problem with numbers, as you know, and words. So I didn’t use them. I had no numbers, no words. I color coded everything. I had color-coded file cabinets, listing cards, one bedrooms are one color, two bedrooms are another color. When everybody else in the industry had white, I had buttons on things that signified things. I just did a visual organization, anything I touched, okay, and even right down to the memos that went out to congratulate people, I didn’t use words. I found pictures and put them together and it would make them laugh. So they got the message.

So everything was visually done, and very much like my mother, if I had to do it twice, I said, “I’m never going to do this again. How could I repeat it and have it automatically in place?” So everything was automatic. Everything. Yeah, it was really, if you walked into my company, I’m probably most proud, I shouldn’t be most proud of it, it’s systems. How excited can you get about systems? But I love them. I was so proud of the company, how well run it was. Because it was like, “Da, da, da, da, da.” You’d swear like a Nazi was running it. “Da, da, da, da, da.”

Tim Ferriss: And I get very excited about systems, so I’m sure the — 

Barbara Corcoran: Do you?

Tim Ferriss: Oh, yes, very much. I get very excited about systems and automating. So I guess we have that in common. You have the automation for these repetitive tasks or processes. You also have the chutzpah and the talent of, say, driving the press and getting attention. What other innovations in this industry really paid off in the early days, like the first handful of years of competing against these old boy networks, where they have committees and they have to get approvals — 

Barbara Corcoran: Isn’t that true?

Tim Ferriss: — then they have the lawyers, and so on and so forth. What were some of the ways that you experimented and innovated in the first five years, let’s just say, if anything comes to mind?

Barbara Corcoran: I think it all comes under the umbrella of urgency. If I thought of an idea on a Monday, I had it on the street by Tuesday. Big guys couldn’t do that. And if I thought of an idea, I asked myself, “Is anyone else doing it?” And no one else was doing it. I said, “Let’s give it a shot.” And you know, you try five things, one thing works, okay. But I kept trying different things, different things. There was a system in New York, which is unofficially still the system, even though people don’t really acknowledge it, where no one shared listings, everybody corralled listings, kept the good ones for themselves. Everybody in New York was signed up for that. There was no MLS, and I declared that we were going to start sharing our listings. My salespeople almost killed me. “Why should we share? Nobody else is sharing!” Which you can understand, “Because people will follow us, customers will like it, and people will follow us.”

Well, they didn’t follow us, and it took two years before the customers even caught onto it. And then the Real Estate Board of New York, all my competitors, I don’t even know what the motion is called, but they filed me at the real estate board, in a virtual real estate lawsuit without the money, to stop me from doing business in the state, because they said I falsely advertised, because I was advertising like crazy, what I call central listing system, because we had no MLS.

So I called it central listing system. “If you list with us, you will hit every broker in the community. If you list with your competitor, you’ll hit three percent,” which was true. Well, they told me the way they interpreted it was different. They kind of thought that I was saying to everybody that they were no good, which I kind of was, I guess. But they all banded against me and wanted to throw me out of business. And that was tenuous. It was a rough time, but that was something, trying to do things differently that didn’t pay off so good, really. If I had to do over again, I wouldn’t have done it.

Tim Ferriss: You wouldn’t have done it?

Barbara Corcoran: No, not worth the hassle.

Tim Ferriss: So we can talk about all sorts of highlights, and I do want to talk about some highlights, but let’s talk about, briefly, Homes on Tape. 

Barbara Corcoran: Yeah, was that good. I made a juicy $1.225 million in one day, three hours to be exact. That was another idea they said I couldn’t do. Huh, they were wrong. There was no law against it, I checked the law. Okay, what I did was, it was a terrible real estate market, it was when interest rates in the early ’80s, I think, or late ’70s, were at 18 percent. So no one bought real estate in New York. Nobody would dare buy, unless they had all cash, and very few people. So I thought of this idea. I copied it from a puppy sale that I went to with my mother. I guess I won’t give you that detail. I’ll tell you how I applied it to real estate. 

Tim Ferriss: Wait, wait, wait. I’m so curious. Wait, no. Tell me the story. So puppy sale, what happened at the puppy sale?

Barbara Corcoran: The puppy sale, which my mother took us to visit our Grandpa Ward down in New Jersey, the shoreline. My mother made us sit and watch the farmer next door who was having puppies, Jack Russells for sale. And she had maybe eight or nine puppies to sell. And there was a long line of fancy cars, cars I had never seen so fancy. They were all from New York City, my mother’s told us. “All these fancy city people have come to buy the puppies.” There must’ve been 30 cars waiting to get a puppy. And there was so much fighting in the line when the last puppy was taken, because there wasn’t enough puppies to give everybody a puppy, of course. My mother said, “She’s really a smart woman, watch her operate.” And I remember thinking, “Operate? Like she’s going to cut the puppies up,” because I was young enough not to know what that means.

But it was her operation, she did this regularly. She had a bunch of dogs, and she would oversubscribe the appointments. They all had appointments, they left angry. So then I had 88 apartments owned by Prudential Insurance and Bernie Mendik. They couldn’t have an auction. They said they had to get rid of them. What could I do? I looked at them and realized they were not saleable. They had no kitchens, they were dumpy. They were in the wrong buildings. They were just really the losers in the marketplace. And so I went back and said I couldn’t sell it, nobody could sell it. I couldn’t think of any way to sell it, unless they let me do an auction. They said, “No auction.” And then Bernie Mendik, talk about positive reinforcing, great developer, he said to me, “Barbara, you’re such a smart girl. You’ll figure it out.” And I thought, “I will.” And I went home and I copied the puppy sale.

So I priced the 88 apartments exactly alike. Different floors, different locations, views, no views, no kitchens, didn’t have a kitchen, had a back wall, whatever, equalize them like the puppies. And I offered them for the same price, which now you’ll say, “Why wouldn’t people buy them?” But not a great price at the day. But they were all flat priced at 59,900, inch under 60,000. And I had almost 180 people waiting for me, the morning of the puppy sale, the morning of the one-price sale. The one-price sale, I called it. And you should have seen the couples, the individuals running.

I had a bus waiting for them for the East Side and West Side. It said, “Deals on wheels, deals on wheels.” And it took them to the West Side, took them up the Upper East Side, everywhere, and they grabbed those apartments. And then I had a great — well, I shouldn’t really say a scam. I had the contract of sales loaded up, big stacks of them, with signatures on. I signed them all. And then I had a new stack with no signatures. I go, “These are taken, sign the contract here.” People walking, signing so fast. And I sold them all, like within close to three hours, two and a half hours. And Bernie Mendik wrote me a check, and I opened two offices.

Tim Ferriss: How did you advertise this?

Barbara Corcoran: I didn’t advertise it, I had no money.

Tim Ferriss: How did you get the word out to people? How did they learn about the sale?

Barbara Corcoran: The best way, who doesn’t like a secret? I didn’t have money to advertise, but I wouldn’t have anyway, if I had the money. I told my salespeople, “Only bring your two best customers, pick of the litter. You get there early, your customer is going to get the best pick, get there early, but don’t you dare bring more than two customers, there aren’t enough to go around.” Now, two times, I guess I had at the time, 150 salespeople. That’s 300 people. That’s much more than I had apartments. And so it guaranteed me a line.

And they were all — there were people upset. You bet you they were, like, “I didn’t get my…” I was going to call it a puppy again. “I didn’t get my apartment. I didn’t get my apartment.” And you might ask, “Why would the person last in line who got the runt of the litter, a horrible apartment, who wants it? Why would they buy it?” Because they could turn around and see another 100 people in line, because in sales, everybody wants what they — you short supply, it’s kind of like one empty desk, the same theory. You make it tight. You can’t always get it. So people reach for it.

Tim Ferriss: Yeah, scarcity.

Barbara Corcoran: Yeah, yeah, yeah.

Tim Ferriss: People love scarcity. They love it.

Barbara Corcoran: That was the word I was groping for and couldn’t remember. Scarcity, yeah.

Tim Ferriss: Yeah, scarcity. Scarcity. And on the talent side, I want to ask you about Esther Kaplan. Am I saying that correctly?

Barbara Corcoran: Wonderful Esther.

Tim Ferriss: So wonderful Esther, when you first met her, it seems like — I’m just going to read here, this is from CNBC. “She was a petite woman, dressed in a little knit suit, with little pearl buttons, and spoke so softly, I could barely hear what she was saying. I had already learned that great salespeople were typically loud and enthusiastic.”

Barbara Corcoran: Yeah, it’s true.

Tim Ferriss: “So I handed Esther my car and told her I’d call her if something opened, having no intention of calling her.” So what changed? Why was she to be seen again? How did that actually get salvaged?

Barbara Corcoran: Boy, thank God she opened her purse when I gave her my business card, to put the business card in her purse, and that was all the difference, because she opened that purse with her little click. Even the click of her purse was concise, she was one of those. And she opened it up, and she looked for a place to file the card, and she tilted it toward me like you are where you are now. And she had a file cabinet inside it, not a metal one, but she had partitions with labels in her little purse. And I’ll tell you, I had never seen it in my life, and I’ve never seen it since. I thought to myself, which I’ve said before, but I remember consciously thinking, “I’d like to put my business in that lady’s purse.”

And I told her I’d open a position for her. I’d teach her everything I knew, she’d be my right-hand person, blah, blah, blah. I never expected her to make a sale, honestly. She did. She was a consistently hard worker, and sold, which she needed to, because I didn’t want to pay her to help me out. I didn’t have the money, but I told her I’d give her 10 percent of my business if she would be my right-hand man, and I’d teach her everything I know about selling. And that was a wonderful partnership. I could have never built that business without her. So she was my exact opposite. She did everything well that I didn’t do well, and I did everything well she didn’t do well. That was a lucky day.

Tim Ferriss: Yeah, what a lucky day.

Barbara Corcoran: It was.

Tim Ferriss: And lucky she filtered her purse.

Barbara Corcoran: Thank God.

Tim Ferriss: Did you find out if she did it accidentally or on purpose?

Barbara Corcoran: I’m having lunch with her tomorrow. She claims now, and she’s very elderly, I’m hoping she makes the lunch. She said her purse wasn’t nearly as organized as I make it up to be. I said, “It was, Esther. It really was.” She goes, “No.” It was. So we argue about that all the time. But she likes it. She says, “Even if it’s a story, I like it,” but it’s not a story. I distinctly remember what that purse looked like. I could draw you a picture.

Tim Ferriss: What were some elements of the secret recipe of teaching her everything you knew about sales? I mean, you’re an excellent salesperson. What were some of the key elements of what you taught her about sales?

Barbara Corcoran: How to assess a customer immediately when they’re talking to you on the phone, immediately. And it isn’t how much money they had to spend, what they’re looking for, what part of town, whether you even have the listing possibly to show them. The whole thing was urgency. “When do you need the apartment for?” I taught her the golden question in all sales. “When do you need it for?” “Oh, we’d like to get in by Christmas.” That’s a decent answer. At least it has a timeline. Another answer, “Whenever we find the right thing,” don’t work with them. The best answer of all is, “I really have to find something within the month because I’m being transferred here.” “Terrific, what are you doing today?” So to rate your customers based on need only, don’t worry about another thing. Just do they need it? And get out with them if they need it.

And so I taught her how to pick the right customers to work with. And nothing unusual, I taught all my salespeople how to do that, how to qualify customers, how to rate them A, B, and C. A, immediate, B, sort of immediate, C, forget about it, don’t call them back. And I also taught her how to hustle, how to build a routine in showing customers, show them one apartment that’s terrible. Or you could reverse it, show them the apartment you think they’ll buy first, and they compare everything else to it. There’s a certain sequence to selling that you want to expose. How to dress for the part, how to get away with not paying for the cab. Very important when you don’t have money in New York City. How do you show apartments — 

Tim Ferriss: How do you get away with that?

Barbara Corcoran: Try to hang out with the men. They usually won’t let a lady pay for the cab.

Tim Ferriss: It’s true, true.

Barbara Corcoran: So that’s a bonus. You could line up eight apartments to show to a man, but if you’re showing it to a woman, make sure the apartments are close, limited to three, not because you’re biased against women, but you had to make the cab fare. All these little details, how to sequence what you show. Like, what street? 86th Street was a choppy street. So I always approached 86th Street, not from Lexington, where my office came from, but I always went to York and East End Avenue. It was quiet, with the birds, and then got out of the cab and walked them through that neighborhood up to 86th. I wouldn’t say — well, maybe some people might call it scamming people, but presenting it as best you can. All those things are so important in sales.

Tim Ferriss: Super important.

Barbara Corcoran: Thoughtfulness. Thoughtfulness in how you present and, oh, and how to close. How to close, the best — 

Tim Ferriss: How do you close? That’s what I was going to ask, that’s what I was going to ask.

Barbara Corcoran: Very important thing, the reverse close, the best close in the world for any business. And it would start like this. “Listen, today I’m going to show you a number of apartments. I don’t expect you’re going to like all of them, but they’re all to be measured against one another. I’ll show you a range of prices, so you see the value.” This way, you’re moving them from the price they said they had to have, you would have like a 10 percent leeway. “I’m going to show you all of this stuff, and I want you to promise me right up front, you will not buy anything today.”

“What do you mean, I won’t buy anything?” “Because I don’t want you to be rash, everything takes thought. You should really buy something you love. And even if you think you love it today, you cannot buy it the same day, because it might not really be a love affair. Promise me you won’t buy anything.” I would have customers calling me at night, panting and begging me to let them buy something. It’s a routine, right?

Tim Ferriss: Wow, right.

Barbara Corcoran: It’s sales, but every customer was happy with what I sold them. Every customer referred their business. So I knew I was doing good and making everybody happy. It wasn’t like I was selling anything bad. I always believed in what I sold or I wouldn’t have shown it, you know? I’m saying that because I don’t want you to think I’m a bad person.

Tim Ferriss: No, I don’t think you’re a bad person. I mean, you’ve had a very, very low, very low churn rate in your company and companies, and I don’t think that for a second. I’m curious about the aftercare, if you had any particular type of follow-up, like after you sell something to someone, after you sell a home. Was there any type of call the day after or kind of protocol for that that you had within the company?

Barbara Corcoran: Well first of all, definitely, I bought a gift, which was from the salesman, because I want them to get the repeat business. Those are my men, I need that. Always sent a gift. I always had a lovely gift that wasn’t too expensive, but we were making money, so I could afford it. And the most important follow-up was to follow up. I made sure that, every three months, they got a postcard from the salesman, but it had my face on it, my brand on it, saying, “Hello.” I had cute little messages. Really hokey, now that I look back at it, but it’s unimportant. What was important is they didn’t have to open an envelope to find the message. They had to see it, because it was on a postcard, and it had a rhythm to it. Always like a steady drip, steady drip, so it was hard for them to forget us.

I remember I learned this lesson, I didn’t do it the first one or two years, but I was at Lincoln Center one day, having a lovely dinner with a friend, and I sat next to a couple, and they were talking about moving, and they were trying to recollect the name of the agent, right there, right next to me. And they were saying, “What was her name? Where did she wear?” But they had lived in this apartment like 15 years. And I thought to myself, “Oh, my God, that’s terrible.” And I went right back and created the system to stay in touch with people, because I saw what a lawsuit was. How much money did that mysterious agent lose that day? Probably a lot of money. They looked rich to me, the way they were dressed. I learned the lesson at her expense, whoever she was.

Tim Ferriss: Yeah, stay front and center in the mind of your customers. And what was the gift? I’m so curious. How did you choose what kind of gift you — 

Barbara Corcoran: We varied it, we varied it. We started, I think, with a calendar. Everybody gives a calendar, but my face was on it. Pretty ego-driven, don’t you think? Why would somebody hang a calendar with my face on it? A pin-up girl, maybe, but my face. “Ahh,” you know? But at least they see who I was. Then we did bottles of wine, Beaujolais. If it was that time of year, a nice, hardy red wine, with a lovely handwritten note. I don’t know what we did, we didn’t do anything special. But the fact of the matter is we did it, and a lot of people didn’t.

Tim Ferriss: It was the cadence. It was the steady drip.

Barbara Corcoran: Yes, it was. It really was.

Tim Ferriss: So speaking of consistency, I’ve heard you mention that exercise is your therapy. You’re very sharp, mentally, physically. What does your exercise routine look like? What has it looked like over the years?

Barbara Corcoran: Nothing special, but what it does have is consistency, and that’s the key to any exercise. I don’t think it matters what you do, okay. I’ve thought of taking up different kinds of exercises, I never get to it, but I have four appointments with a trainer well before I could afford it. She’d be the last person I’d give up if I was going to the poor house, a trainer that is at my door and I have no choice, because if I had a choice, I would never work out. But there she is, Margaret, who’s been with me now, like, 15 years, and I’ve got to do it. So it’s weightlifting, stretching, cardiovascular, a little bit of that.

I get away with this as little as I can. I don’t like it, I’ve never liked a day of training in my life. I really don’t like it. I’d love to give it up. I hurt my back a short while, and she insisted on coming anyway. I’m like, “Don’t I get a break?” But, no. 

Tim Ferriss: So you wish you could give it up but you don’t. So what do you get from the exercise? How would you explain that?

Barbara Corcoran: Oh, first of all, you have your own time. I have an hour just for me, splurging on me. It’s all about me. And I don’t ever have any time that, I don’t make the time. What I also get is relaxation. I run hot. “Ooh,” calms me down, calms you down. I get vanity. I look firm, I look good in clothes. People say, “You have a great figure,” so I get all the flattery. That’s good for my ego. And most importantly, I find that when I don’t exercise, it’s really a question what you don’t like. Even when I go on vacation and give myself a break for a week, I don’t think as well. I think it gives you a great ability to think clearly, I really do. Exercise and pulling weeds, in my mind, are the two best therapies in the world. I don’t really think you really don’t need much more than that. You straighten out all your problems that way.

Tim Ferriss: So you’re building strength. And, yeah, part of strength in my mind is also how you contend with fear if and when it presents itself. You do not strike me as a fearful person. And I want to bring up something I found. This is in New York Magazine, and I want to ask you about this. So here’s the paragraph. “Corcoran and Trump haven’t always seen eye to eye. In 1994, Corcoran accused Trump of not paying millions of dollars of commissions to tour brokers who brought him key Hong Kong investors of his Riverside South project.”

So I think a lot of people are intimidated by many things in life. Certainly, a lot of people would be intimidated by somebody like Trump, but it seems like you were willing to fight. And I’m curious how you develop that, or if that has been something from childhood that you’ve just carried forward. But a lot of people know what they should do or the moral thing to do, and they’re afraid to do it, because they’re afraid of some type of punishment or someone who is intimidating. And I’m wondering if you could just speak to that, maybe to the example, but it could be another example, and your willingness to not back down.

Barbara Corcoran: Well, that’s a good example, because he’s an intimidating man. He’s a bully. He’s a real-life bully in every way. With him, I wasn’t scared for a second. I had never had a lawsuit. I didn’t know how to hire an attorney. I didn’t know what it was about. I’m not a fighter. You’ve got me wrong on that, Tim. I don’t like to fight. I’ll walk a mile to avoid a fight, but when someone insults me, it brings out the fight in me. I don’t know where that comes from. I guess same thing with the competitors being insulting to me. I know where that comes from. When my father would drink, and he was a social drinker, so it wasn’t a big issue, but it was an issue, he would be abusive with his mouth, like a bully. And he was a loveliest man in the world and would turn into a bully.

I hated him for that. I hated how he talked to my mother. I hated how he talked to his children. And so it would just tip into that. So when Donald is like, “You’re not seeing a penny,” I’m like, I turn into a killer. It’s insulting to think I’ll really roll over on that, and thank God how life happens. It was the first year I made a real profit in Corcoran Group, because I never made money, because I was always throwing my money back in and living so cheap so that I could afford to open offices. Always, the money went to the business, the money went to the business, never came to me. And that year, I had more money than I could spend. I had over a million dollars in profit. The year before, the many years before that I either had losses, or 100,000, but it cost me $500,000 to sue.

But I had the cash, think about that. So I felt powerful, and I got the money to fight it, and I’m certainly not going to walk away. Because you know what my thinking is? I’m walking away from a well-fought fight, you resent it and regret it for the rest of your life. I didn’t want to be that girl who said, “Son of a bitch, how did he get away with…” You really, you regret when you don’t confront things, I think in anything, but particularly with a moral fight. And in my mind, that was morals, it’s all about morals. I earned the money, “You signed you’d give it to me and you’re not giving it to me? You’re suing me instead? Oh, no, I don’t think so.”

But what other lesson I learned at that juncture, just as important as a willingness to fight is get the right help. I’d never had a lawsuit, as I just said. And I interviewed the top law firm, and I think I had five or maybe four, maybe four is more realistic, the four top attorneys and the four litigious firms in town. And I wanted to hire the toughest guy, thinking, “I need a tough guy to beat this tough guy.” But I didn’t conclude there. I met an attorney, I forget which firm, Skadden, Arps, I think it was with, Richard Seltzer. He’s now retired, and he had the most solid thinking. And I used my common sense to say, “Which attorney is not saying I’ll win, but which attorney is saying why he’ll win?”

And this guy told me why he was going to win, and the strategy, and it was so simple. I said, “You’ve got the case.” And he was a showman in court, like show business. And his thinking was so smart, and he didn’t give Donald an inch. And he called me after the lawsuit was won, like two weeks later, and said, “I need your permission to work for Donald Trump.” “Donald Trump, what are you working…” He said, “He’s hiring me for a major lawsuit.” He said, “It’s a conflict of interest.” I said, “I’ve got my money on the way. So no problem,” you know?

Tim Ferriss: That is incredible, that it only took two weeks.

Barbara Corcoran: No, to call the attorney. Oh, I wasn’t getting my money — no, I’m so sorry. I misrepresented. To call Donald Trump took about two weeks, I guess, because my attorney called me like two weeks later, “Can I represent Donald Trump?” But it took me five years to get the commission, because the judge — he said he didn’t have the money, which was true. He was near bankruptcy. So the judge made him pay me the commission in $55,555 in stolen payments for five years, or whatever, how many years it took. And you know what the best part of getting those commission checks? You’ve done such research, maybe you read this, but I’ve got to tell it, because it’s my favorite thing.

Tim Ferriss: Oh, please.

Barbara Corcoran: I sent him a giant bouquet of flowers when I got the first $55,000 hand delivered to me by messenger. I said, “Thank you, Donald,” hand wrote it. “I really appreciate the check.” And I sent him the note with the same messenger, and he took them back with the flowers, and he sent it back to me and he put a big — he always wrote them thick ink, you know, and he put on it, “Rejected,” and sent the flowers back to me. “Why is that stupid…” But then I had the flowers, so I sent him flowers for the next four or five — whatever many years it was. And flowers that I liked, because I knew he sent them back every month.

Tim Ferriss: “Take them back.”

Barbara Corcoran: “Rejected.” That’s the best part of the lawsuit.

Tim Ferriss: Oh, that is so good. That is amazing. I want to come back to something you said at the beginning, which is you’d walk a mile to avoid a fight. And I think this is really important to revisit, because I’m a fighter.

Barbara Corcoran: You are? You don’t seem like it.

Tim Ferriss: Well, let me take that back. I’ve historically been a fighter, very competitive, and I think to a fault, where I’ve been willing to justify fights based on principle more often than has been helpful. And as I’ve gotten older, it’s changed.

Barbara Corcoran: Were they really based on principle, you think?

Tim Ferriss: That’s a very good question. I think it was a certain sense of moral outrage about some type of situation. So for instance, if — I’m not going to name the company, but I did a deal with a very large company, ended up being a public company, and at one point they were paying, they were retaining me to help with consulting and a various number of other things. I hit their performance metrics and they were like, “Yeah, we’re not going to pay you.” And I was like, “But I hit your metrics.” And they basically said — 

Barbara Corcoran: Oh, that’s like Donald Trump.

Tim Ferriss: Yeah, they basically said, “Look, we have 20 in-house counsel. If you want to fight, let’s fight.” And I was like, “Really?” And that pissed me off. Now, ultimately that — 

Barbara Corcoran: It had to scare you, it had to scare you.

Tim Ferriss: Yeah, yeah, of course. And I mean, it’s intimidating because I’m paying out of pocket by the hour, even if I have a retainer. But I have ended up realizing that, for me, preserving my energy for the things that are really high leverage and matter is so critical that I want to avoid fights when I can. I will still fight, in certain instances. But how do you choose which fights to walk away from and which ones to engage with? Because I do know people, for instance, who are constantly in lawsuits.

Barbara Corcoran: So do I.

Tim Ferriss: It’s just a waste of their lives.

Barbara Corcoran: They’re not happy people, by the way.

Tim Ferriss: No, they’re not.

Barbara Corcoran: Those people that are constantly in lawsuits here. Which ones, how I assess them is probably backwards. I think, “How much energy is it going to take for me?” Because it’s always negative energy, it’s never positive. So I think, “How much energy is it going to take for me, for how long?” And I take a quick guess and I make my decision there, not on whether I could win or not, but just, “Is it worth the energy? Is it worth the energy?”

You do have to stand up for yourself, like on that lawsuit with Trump, because there was a lot of money at stake, and certainly that entered into it. I don’t know if I would’ve sued him for $10. There was a lot of money on the table, but I will almost always walk away, because it’s never worth my energy. You don’t really win. That’s what I’ve concluded. Now that I’m older, I watch people, not so much myself, but other people that I know well in business, they never win. And the people, like you said, the people who are litigious all the time, righteous litigiously, even worse, they’re always unhappy. It almost fuels their unhappiness, you know? What a waste.

Tim Ferriss: Yeah, I agree. So this is going to be a bit of a left turn, but I’m so curious. In the course of doing some research I found, on this website in the UK, this is Express.co.uk.

Barbara Corcoran: UK? Wow.

Tim Ferriss: Oh, yeah. So “Shark Tank businesswoman, Barbara Corcoran, has offered fans a rare glimpse of her mobile trailer for a video with TikTok Star.” I think it’s Caleb, perhaps Simpson.

Barbara Corcoran: Cute guy.

Tim Ferriss: Yeah, so it says that you use this humble Los Angeles trailer a few weeks per year. What is the story behind the trailer? I don’t know anything about it. I’m just wondering how you use it, why you use it, if you use it?

Barbara Corcoran: No, I do use it, and more than a few weeks a year, probably five weeks a year, maybe. I shoot my show of Shark Tank in L.A. and I always stay at the Beverly Hills Hotel, which is so luxurious, because they pay for it. I’d never pay the price, right? They put me up there. My next door neighbor in New York said, “I’ve always wanted to buy a house in L.A.” I said, “That’s funny, I’m thinking the same thing. Why don’t we buy it together?” So we went out there to buy it together. Her husband wouldn’t let her buy it. And then, I took a car, and I drove around, and I found a trailer park, and I fell in love with it.

That’s all I was trying to turn on US 1, which is hard to turn on, takes forever to make a U-turn. So I took her right up the driveway and I was in a trailer park, and it’s only a half hour from my studio. And I went around, and looked at all the trailers, and picked out, I thought, the best position, because you could always change inside, but you can’t change the location. And I met a lovely woman who owned the home, and I asked her if she’d like to sell it. She said, “No.” She had no intention of selling, maybe in a few years. And so I called the local broker. I never liked the homes I saw there that she showed me. And I went back to the lady, I said, “What if I give you a life estate? You could come and visit whenever you want. Would you move out?” And she said, “Yes.” And she — 

Tim Ferriss: Sorry, say it one more time. If you gave her what?

Barbara Corcoran: A life estate, that she what that could vacation — 

Tim Ferriss: What is that?

Barbara Corcoran: A right to use it for two weeks a year, any two weeks she wanted. She’s been using it two weeks a year, she’s so happy. She brings her family. She’s had reunions there, as tiny as it is, and she sold it to me. Now, I paid for that trailer, $800,000, which everybody in the trailer park said, “A woman from New York just paid $800,000 for a trailer.” I purposely overpaid by 100,000, but it seems so undervalued to me. I said, “What do I care about? I’m going to use it for 10, 20 years. What do I care about 100,000?” Which us true in buying real estate, what do you care about it, if you have the money to spend?

But you know, I put the place into a spin. We’ve had Hollywood, not because of me, I just bought at the right time. I put another 200, maybe $300,000 into it, and now it’s worth like 1.9, maybe two, not a lot when you’re in New York and you have crazy prices. But for that trailer park, it’s a lot of money. But I have a full view of the ocean. I’m like at the Four Seasons Hotel, flowers, I have my garden. It couldn’t be more beautiful. And so it was one of the best decisions I really made, definitely.

Tim Ferriss: What else led you to fall in love with the trailer park? Because I imagine a lot of people listening, they’re like, “Oh, my God, I would never imagine that Barbara would fall in love with this setting and this particular setup.” The view sounds amazing. The garden and the plants sound amazing, but what else, if anything, led you to fall in love with it?

Barbara Corcoran: I very much fell in love with my neighbors. I’ll tell you, my neighbors right up and down the street, you never get to know the neighbors on the other streets. So there’s like a total of 12, 13 houses. I know most of them. I know most of them well. I have dinner at their house. They come to my house for dinner. But why I liked them is they were just like my mother and father. They were simple, blue collar people with real values that were as lovely as the day is long. The loveliest people in every way. They cared for my trailer when I wasn’t there, let me know if there was trouble, a storm coming, making sure I was batting down.

I mean, if I tried to find neighbors in New York City around my very expensive apartment to even give me a pound of sugar, I’d be waiting forever. But these neighbors are so genuine and so real. They’re all from the Hollywood business, but they’re camera hands, stage hands, ladder people, holding the script people, they all had these menial jobs that most people see menial. They love their jobs. They were so happy to be in Hollywood. They’re always talking about it. They’ve had happy lives and they share them with me. So I could never move away, just based on my neighbors. You know, my trailer blew up or something, I would just move right back on the same block. They’re really lovely people, really.

Tim Ferriss: And why did you deliberately overpay by $100,000? Was that to get the deal done or was there another reason?

Barbara Corcoran: I’ve always paid for any real estate I want, I always overbid. I even get my construction jobs done by overpaying. Two summers ago, there was so much construction work in Fire Island, where I bought a new home, but it was dilapidated. I had to rebuild it. Last minute, the builder said to me, “I can’t handle it. You’re going to have to wait a year.” I said, “Really? Why is that?” He said, “Well, I can’t get the help. I can’t get the materials, it’s COVID, blah, blah, blah, blah.” He gave me a list so long, I was suspicious. I said, “What if I gave you $200,000? Could you get it done this month?” And he said, “Yes.” Didn’t even have to think about it. “Yes,” he said.

And my house was done in a month. The house that was supposed to take nine months was done in a month. So I always am willing to overpay. And you know who I really learned that from? Well, maybe didn’t learn it from, but first heard it, and I’ve always often thought of it was from Harry Helmsley. When he was the biggest landowner, big developer in New York and owned all the best real estate and the best locations, I attended a speech by him and somebody in the audience said, “So, like, what’s another tip? What’s another tip on buying? How do you win the bid and everything?”

He says, “I always overpay for everything I want.” He said, “Because you forget about it the minute you own it.” And I thought, “If Harry Helmsley, so rich, could overpay,” I was stunned by that answer. And I always overpaid and always bought real estate that wasn’t for sale, just by knocking on the door, you get exactly what you want. “I love that house. Let me knock on the door.” And you can often be two years early, but you could be persuasive with money. Yes, it works, works very well. And I love my homes.

Tim Ferriss: If you were going to give advice to yourself 30 years ago, let’s just say, you could send back a time capsule to give some advice to yourself 30 years ago, any advice come to mind? Tips or anything at all, warnings?

Barbara Corcoran: I would’ve told myself, because I had to learn this over a few years, hire happy people. I mean, I started hiring salespeople that were phenomenal from other firms, I turned into an ace recruiter, but they were miserable at home. They drove me crazy. Great salespeople have two personalities, most of them have two personalities. So I had, for a number of years, I had miserable people that could suck the life out of you with their bitching and complaining.

And then I decided one day, “I’ll never ever hire anyone unhappy again.” And that was like pulling the curtains back, and the sky opened up for me in every way. It was fun at work every day. You know, complainers are a funny thing. They’re part of all families, all business, all circumstances. But they’re horrible. Just, complainers, they suck the life out of you. So I think I would’ve gotten tough on complainers right away and fired everybody who complained, “You’re out of here, you’re out, you’re out.” It took me a while.

Tim Ferriss: I’ve heard you say complainers are thieves and that stuck. 

Barbara Corcoran: That’s exactly how they are.

Tim Ferriss: Yeah, that really stuck. So Barbara, let me ask you about Barbara In Your Pocket. So Barbara In Your Pocket is the top business channel on Patreon, why did you start this? It certainly seems like a rare opportunity for people to get a lot of insight, a lot of tactical advice from someone who’s been in the trenches, has had more adventures than you could possibly count — 

Barbara Corcoran: Yes, yes, yes.

Tim Ferriss: — misadventures too, I am sure. Why did you decide to do this?

Barbara Corcoran: Two reasons, I wanted to make a team of entrepreneurs that I loved, and also, I was constantly giving advice, constantly giving courtesy meetings to people to help them with them with their.. Constant. And I would get to maybe seven, eight a week, and it was heartbreaking, because I’d have 30 people who wanted help. So I just tried to think of a system where I could help a whole bunch of people at once, where they could interact with me, I could answer their questions, and then also get help from the other entrepreneurs, because all my entrepreneurs from Shark Tank help each other.

I molded them into a family. It’s not one business, it’s 130 businesses. They don’t all help. Some of them aren’t going to make it, but most really help. And so I wanted to bring people together to help each other, and I wanted to give them honest advice, no bullshit advice, not slicing my words, tell them what I really thought was a problem, whether they wanted to hear it or not, and I felt I could help them really build their business.

But it’s young. We just got started. I’m trying a new thing every week, a new approach to it, getting the feedback. They tell me what they like, what they don’t like, what they want to do differently. But it’s taken a life of its own. It’s only a muffle, but I see it like, “Boom, boom, boom, boom.” I almost feel like I have my old Corcoran Group back. Isn’t that weird? Because I see their faces, they tell me their problems. I can see what’s good about them, I can see what’s bad about them right away. I feel like I’m building my Corcoran Group all over again. I couldn’t have done it without a large platform to do it that way.

Tim Ferriss: Yeah, Patreon’s great. And I’ll just read this for folks as well. So the Barbara In Your Pocket channel will be providing exclusive content created for entrepreneurs at every level. And you’ll be doing a deep dive into the topics most important in business today, giving an inside look at how you run your business, how you’ve run your businesses, and also working with your Shark Tank companies, as well as joining members live to answer their toughest questions. 

And I don’t know if this is a tough question, but a question I have for you is what gives you the most energy these days? What is it that drives you, feeds you energetically? What do you find really tips the balance for you?

Barbara Corcoran: Easy. An entrepreneur coming back and saying I made a difference, that my suggestion to do this worked, and is successful because of it, which they’re exaggerating, I realize that. But feeling, or not feeling, knowing the feeling of having somebody come back as proof that I made a difference. If you think about it, I think maybe all of us just want to make a difference, you know? I don’t know, that’s a satisfying thing in life, but I like to make a difference with everybody by a smile, my hello, whatever I do. But my sweet spot is helping entrepreneurs. I know I make a difference. So having that confirmation come back at me makes my day. I almost have a hard time working after. It’s like, “Oh, I’m cool, I’m cool, I’m cool.” Then I squeeze my head down and go, “Get back to work.” That’s the most satisfying. Yeah, without a doubt.

Tim Ferriss: So Barbara, just a few more questions. This has been so fun. Thank you again for the time.

Barbara Corcoran: My pleasure, Tim.

Tim Ferriss: I’ve really, really enjoyed this. If you could put a message, something on a billboard, a huge billboard, this is metaphorically speaking, just to get anything out to hundreds of millions of people, billions of people, could be a quote, could be a word, could be a question, could be an image, nothing commercial, but just something to make an impact, what might you put on that billboard?

Barbara Corcoran: I’ll tell you, it came right to my head the minute you started asking the question. I would say, “You’re a lot more capable than you think you are.” People write themselves off so early. I mean, I saw people through my career, whether they be entrepreneurs, the Shark Tank, whether they be Corcoran Group agents, come in with battle scars from life, not really thinking they deserve this success or could accomplish it. I saw losers become winners constantly, and they wrote themselves off somehow too early. So I think people are so much more capable than they think they are. So I would write, “YOU,” with capital Y-O-U, “are more capable than you think you are.” Maybe I could come up with something better, but that’s how I feel. So I’m telling you that now.

Tim Ferriss: I think that’s a solid answer. That is a great answer. Well, Barbara, thank you so much. People can find you on all social, and we’ll link in the show notes for all of this. Barbara Corcoran, almost everywhere, Barbara In Your Pocket. People can find you at patreon.com/barbaracorcoran. Is there anything else you would like to say before we come to a close?V

Barbara Corcoran: Very much so, yes. I hope you can give me a moment, Tim?

Tim Ferriss: Of course, take all the time you want.

Barbara Corcoran: Thank you. No, it’s short. Will you marry me?

Tim Ferriss: You know, I am on the market, so never say never.

Barbara Corcoran: You are, really? You really are in the market? Do you like a little bit older, babe?

Tim Ferriss: I’m not against it, I’m not against it. I spend a lot of time in New York, maybe we’ll have to have an espresso martini and see where things go. I don’t know.

Barbara Corcoran: If you’re serious, I’m serious.

Tim Ferriss: Well, it would be great to meet in person at some point, no matter what. I do spend a lot of time in New York. I grew up there, got a lot of family.

Barbara Corcoran: Ooh, ooh. I’m kidding you, sort of. But I’m happy with your answer.

Tim Ferriss: Yes. Oh, well, thank you, Barbara. You are so good at what you do. You’re so engaging.

Barbara Corcoran: Thank you.

Tim Ferriss: And I’ve enjoyed this conversation so much. I really appreciate you taking the time, so thank you again.

Barbara Corcoran: You build my confidence, thank you. You’re wonderful at what you do. I’m not just giving you a compliment back, but you really are wonderful. I do a lot of these, so you are.

Tim Ferriss: Thank you. Yeah, thank you, Barbara. Well, have a wonderful weekend.

Barbara Corcoran: Bye, Tim. You going to throw kisses?

Tim Ferriss: I’m throwing kisses, kisses and kisses. Bye-bye.

Barbara Corcoran: Okay, bye-bye.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than one billion downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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