Q. What were your early years like?
A. I was born in Edgewater, N.J., and I was the second oldest of 10 kids. I had a phenomenally motivating mom who was a good role model for all of us, boys and girls alike.
In what way?
She was extremely efficient. She had energy to the moon. I never saw her sleep. I don’t think I ever saw her sit down except for dinner, and only for the last five minutes after everyone was served. And she had a positive attitude.
We had two bedrooms for the 10 kids, and my mother and father slept on the convertible couch in the living room. But we had the most organized household in town.
My mother would have made a great drill sergeant. She had amazing organizational systems. She had two sock drawers in the kitchen. The upper drawer had a blue label that said “Boys,” and the bottom drawer was a pink label that said “Girls.” Inside the boys’ drawer were navy socks, all one size. The girls’ socks were all white, all one size.
My mother was also great at figuring out the best qualities of her kids and only focusing on those. She never criticized us. All she did was compliment us on what we did well. It taught us to have a positive attitude about ourselves, and it also taught us to look at the light in people.
And your father?
My father worked two jobs his whole life, mostly as a printing-press foreman. On weekends, he played with us, and he was the best playmate. He taught us the joy of being in the moment and being silly.
He was a hard worker, but we also learned insubordination from my father. He hated every boss he ever worked for except one. He constantly got fired. But he was our hero. Out of my nine siblings, only one works for somebody. Everyone else has their own business.
A lot of C.E.O.s I’ve interviewed come from large families.
Growing up in a large family is like growing up in a town. Everybody takes on a role. You learn to deal with different personalities. Everybody’s got to mesh, so you get training early on for getting along with people. It’s a great advantage.
You also learn independence in a large family. You’re pretty much taking care of yourself, so you grow up fast.
What were you doing outside of class?
I had my first job when I was 11. I had 22 jobs before I started a real estate brokerage business when I was 23.
When you went to college, did you have an idea what you wanted to do for a living or for a career?
I couldn’t believe I even got into a college. My grades weren’t that good. I had dyslexia. School was like one long jail term for me. I hated every minute of it. My idea of hell on earth was being asked to read aloud, and hearing the kids giggle. I learned shame, which can take anybody down.
So I spent six hours a day daydreaming in class. I just gave up by third grade. But my mother’s response was to say: “Don’t even worry about it. You have a wonderful imagination. You’ll learn to fill in all the blanks.” That was powerful for me, and I leaned on that for the rest of my life.
Early management lessons for you, particularly as you built up your real estate agency, the Corcoran Group?
I took to management like a duck to water. It was in my blood. Every single thing I’ve done is just a business version of what my mom did on the home front.
When I hire people, I just look for the light in the person, to see what’s good about them. I can spot it a mile away. And I never read a résumé until after the interview because you never know who wrote it, and you can be fooled by it. If you read a résumé, the interview is nothing but a business small-talk session confirming stuff you just read.
So I’ll just ask: “What do you like? Tell me about your mom. Where did you grow up? What’s your hobby? What was your favorite job? Why?”
If you could ask somebody only one question in a job interview, what would it be?
Tell me about your family. If their family couldn’t give them a positive attitude, there’s nothing I can do that’s going to change it. Early on, I hired a couple of people who had all the markings of great salespeople, but they were not happy people.
I learned that if you have just one unhappy person in a pool of 30 happy people, you feel that weight. I couldn’t wait to get them in my office to tell them they had to leave. I loved firing complainers.
You’ve heard hundreds of pitches in your years on “Shark Tank,” and invested in dozens of entrepreneurs. What are you listening for?
The same thing I’ve always listened for: attitude. I’m looking for someone who, after the Hollywood of “Shark Tank” fades away, is going to stay the course, and always figure out a way to succeed.
The minute I make a deal with someone, I put a photo of them in a matted frame on my wall. They look beautiful. They’re like my kids on my walls.
But the minute I hear them sounding like a victim on the phone, I hang up, walk over to the wall and I flip their picture upside-down. They’ll never succeed. Victims don’t succeed.