Thrive Diary//

Thrive Diary: Barbara Corcoran on Conquering Self-Doubt and the One Quality You Need as an Entrepreneur

The “Shark Tank” investor gives her best advice on thriving through life’s important moments.

Barbara Corcoran wastes no time before asking how much the phone booths in Thrive Global’s office cost. She almost invested in a similar company, and wanted to compare the price point. She’s also curious about the cork stools throughout the new office — she’s been looking for some for her own workplace, but you wouldn’t believe how hard those are to find, she says. At the end of the tour and before beginning her Thrive Diary, she comments on the beauty of the space, but not without musing that a luxurious office likely means lower bonuses for employees. The room laughs — her directness is refreshing. And after all, the real estate mogul and investor on “Shark Tank” has made a name for herself by being frank about all things, including finances.

Corcoran sold her real estate company, The Corcoran Group, in 2001 for $66 million dollars, and has since engaged in several other ventures, like her podcast “Business Unusual,” which she calls her “latest baby.” More recently, she’s excited to be a part of the Real Relief for Visionary Women Campaign: a program that offers eight women entrepreneurs $5,000 grants, business mentoring, and a one-year supply of Systane dry eye solution. One woman will get mentoring sessions with Barbara herself, where she’ll “take their business, analyze it, and revamp it.” But the most important trait to successful entrepreneurship, Barbara stresses, is one that can’t be taught in a mentoring session. “I’m gonna make sure they have the gift of getting through hard times,” she tells Thrive. “If they can’t get through a bad time and pick themselves up — well, that’s the one thing you can’t do for someone. And so I’m gonna pick my winner carefully.” 

Here are excerpts from Corcoran’s Thrive Diary (full video below), where she talks about her foolproof strategy to pitching ideas, the “death party” she had for her birthday, and the hiring lesson she learned the hard way. 

Thrive Global: At Thrive, we refer to negative self-talk as the “obnoxious roommate” living inside your head. How do you quiet your own self-doubt?

Barbara Corcoran: Probably everybody has an obnoxious roommate in their head, as you call it, and it’s a killer. I had a voice in my head since the time I was in school because I was a terrible student. So I have that reel running in my head, I had it probably until I was 30, but I worked on getting rid of it because I knew it was in the way. As a result of [getting rid of it], I was able to accomplish so much because I had my own reel that tells me how wonderful I am and how confident I am. I just kick it right in, and I start falling for her, and that helps me perform. 

TG: What are some of the things that you say to yourself to quiet that negative voice?

BC: The first thing I do when that voice creeps in — and it doesn’t creep in much anymore, I’ve had a lot of years to practice on this — but when it does start to creep in, I declare war. I say, “Get the —”, I won’t use vulgar language, but I say, “get the heck outta here.” I refuse to give it an audience. I picture it as a little witch in my brain that’s coming in and making havoc, and I think of that witch dressed in black and I kick it out of my brain. I just kick her out. Like, “you’re not getting away with this.” It’s like a declaration of war. But I’m a warrior. 

TG: What are your tips for giving a good presentation?

BC: The most important trait if you’re going to make a pitch is communication. Talking simple. I’ve never invested in products on “Shark Tank” where people used fancy language. Like “burn rate.” That means that they’re burning my money up. Pivoting. That’s another recent phrase, I hate that one. “I’m gonna pivot.” Oh, you mean you made three mistakes and now you’re gonna try on your fourth? All these fancy terms disguise failures. No. I like to have someone communicate clearly what they have to sell, what they can sell it for, and who’s gonna buy it. That’s the essence of business. You have a product and a sale. And if you can communicate well and you look the part, and you lay over it a ton of enthusiasm, you’re gonna get what you want from the investor, which is their money — or from your customer, which is their cash. Works every time.

TG: What about the word “rebranding”? Is that another cover-up for continued failure? 

BC: The word rebranding sounds respectable, sounds intelligent, like you’ve assessed where you’re going and you’re going to make a new label. What I don’t like about the word is it covers up the tremendous time and money that was already lost on your old brand that you should have been right about in the first place. So if someone is telling me they’re rebranding — I know there’s a space for it and I’m all for it — but I’m thinking that maybe they won’t get it right this time either. 

TG: I recently read that each season of “Shark Tank” is filmed over two two-week periods. How do you prepare for that type of concentrated intensity?

 BC: The preparation is like working for a marathon. I start preparing three months before. I start working out like crazy. That comes first. I’m not the kind of person that likes to work out, but I get it in because of my vanity. I wanna wear my dress well, so working out is key. And then there’s the shopping. I have [my stylist] Tommy, who dresses me and drives me crazy. He puts shopping days in my book long in advance. Has to have the right heels, the right dress, the right hem. Drives me nuts, but it’s necessary for the show. It’s a visual medium. After two weeks of filming “Shark Tank,” to get half the season in the can, and then we go back again and film another two weeks, you’re totally exhausted. You have to realize that you’re seeing a segment at home that takes seven to eight minutes. We’re asking questions, drilling down for about an hour and fifteen minutes in actual time. The pressure is enormous because you’re really spending your money, and you’re trying to compete with your fellow sharks, and they’re fierce competitors. So when you want something, you might not get it.

TG: So how do you unwind afterwards?

BC: I always book a few days after “Shark Tank” just not to get up. Just to lay on the beach in Los Angeles, where we film. It’s totally exhausting, you need to recover. Two days later, I’m back in New York slamming my feet into my high heels and it starts all over again with some other media thing. 

TG: Thrive’s founder and CEO, Arianna Huffington, is a big believer in style repeats — which basically empowers women to repeat outfits, similarly to how men repeat suits all the time. How do you feel about this concept? 

BC: As an individual, I have no interest in clothing. If left to my own devices I’d live in my khaki pants that I never wash, and a clean t-shirt. But I’m in the TV business. It’s a visual business. So as much as I don’t like dressing up and spending the time, I do it meticulously because I know it’s part of the game. But I don’t like the fact that you have to change all the time and stay up with style because it’s expensive and it takes more time. 

TG: Your podcast, “Business Unusual,” is a new medium for you. What has starting that been like? 

BC: Some people are good at learning, and some people aren’t so fast. I fall into the not so fast camp because I have self-doubt. It’s not that I lack personal confidence, but in trying to make my podcast better and better, and more on target, and more meaningful, I find myself second-guessing myself, as if my advice may not be worthy. So I’m always trying to give a little bit better advice, a little bit more intimate, specific to the problem. I raise the bar on myself so high by the minute that I exhaust myself trying to get there. But when I look back three months ago on my podcast versus the one I did yesterday, I can tell you they’re a lot better. I don’t think there’s any shortcut to getting better at anything than just working your buns off as usual. But it’s a lot of stress. A lot. 

TG: How do you manage that stress?

BC: The best solution I have to managing stress — because I do have a very stressful life — is I have children that keep me balanced. I love my kids more than anything I’ve ever done in business. So that keeps me balanced. And then the second thing is, I weed my garden. I go out and weed my garden and for everything I yank out of that soil, let me tell you something, I get great clarity. So I think you just have to find something that makes you relax, and for me, it’s weeding. I’ll garden as often as I can. And if I’m having a nice day, I don’t feel a need to weed. What I do is clip and deadhead my flowers because I like my garden to be perfect. I’m a perfectionist. 

TG: What do you look for in people when you’re hiring? 

BC: When I hire anyone for my business or when I’m partnering with an entrepreneur on “Shark Tank,” I’m looking for one thing, which is a positive attitude. Nothing gets in the way as much as “we can’t do it.” It’s a killer for any kind of business. I learned years ago through a series of mistakes of hiring the wrong people that you can’t change attitude. I used to get someone with great talent before me and say, “they’re so talented, the sky’s the limit.” But they had a bad attitude And you think, “Oh, I’ll change them around, I’m positive, I can turn everyone around,” No. I not only hire for a positive attitude, but the minute I suspect that I’ve made a mistake — which happens — I get rid of the clunker. Because you put one negative person in a team of ten happy people and sooner or later the happy people are going to get that attitude. It’s powerful. So I stay away from negative people and only focus on attitude when I hire.

TG: It sounds like you’re a person who follows her gut. 

BC: I always follow my gut in everything and I’m going to tell you why. It’s an accumulation of everything you’ve learned in life. A kid has a gut reaction. They learn not to jump because they learn what it’s like to hit their head. Adults are the same way. We never stop learning, but it all accumulates in something we call our gut. And why wouldn’t you trust your gut? I’ll tell you why, because we’re all taught that we should be using our left brain to analyze things and to make decisions. It’s called “rationale” and it lies all the time, but your gut never lies. 

TG: You recently had your 70th birthday, and this year, I saw you celebrated a bit differently with a fake funeral. Do you live your life with death in mind?

BC: I have to congratulate you. That is the first time I’ve ever had that question in my life. And I think I’ve had them all. I’ve been afraid of dying since I was 21. For no reason. I don’t know why. I had no one in my family die early, but I’m always afraid of running out of time. So trying to get over myself, I decided to confront my death on my 70th birthday, and I threw a surprise party. I surprised my friends! As they were waiting for me to arrive to yell SURPRISE, up in my kitchen of my home in New York City, I was downstairs laying down in a coffin. They all knelt at my little kneeling station, and they said their prayers, and told me what they thought of me. Hey, it was a blast. Especially for me. How many people get to die and see what people will say about them before they’re dead? I got to hear it all. I got kisses, cheers, I got the whole shooting match, and then I jumped out with a high kick and did the tango. And a funny thing happened after that party. I don’t know if I had a rite of passage of some kind, but I’m not even counting anymore. “Oh I got 10 good years left,” I used to do that in my head all the time. Now I’m just like “whoa, let’s go.” So maybe I should have had that death party when I was 50, or 40, or 30. 

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