I like this idea of surrounding oneself with "no ladies" rather than "yes men."
What It’s Like to Grow Up With More Money Than You’ll Ever Spend
Did you have a moment in your life when things started getting lavish and you realized, “Oh, I’m super rich”?
When I went off to college, Michael Eisner came in and reinvigorated the company, and then the stock price, which was basically my family’s entire net worth, was ten times, 20 times, 50 times what it had been when I was growing up. So all of the sudden, we went from being comfortable, upper-middle-class people to suddenly my dad had a private jet. That’s when I feel that my dad really lost his way in life. And that’s why I feel hyperconscious about what wealth does to people. I lived in one family as a child, and then I didn’t even recognize the family as I got older.
In what ways did your dad change, other than having a jet?
Actually, having a jet is a really big deal. If I were queen of the world, I would pass a law against private jets, because they enable you to get around a certain reality. You don’t have to go through an airport terminal, you don’t have to interact, you don’t have to be patient, you don’t have to be uncomfortable. These are the things that remind us we’re human.
My dad’s plane was a 737, and it was insane to have a 737 as a private airplane. It had a queen-sized bed with one big long seatbelt across it, and a shower, and it was ridiculous. We would use the plane occasionally because I have four kids, so it was much easier, obviously, to ride on my dad’s plane with them. Then, at a certain point, I just said, “No, I think this is really bad for everybody.”
How did the jet change your dad?
It wasn’t just the plane, but it’s not a small thing when you don’t have to be patient or be around other people. It creates this notion that you’re a little bit better than they are. And for the past 40 years, everything in American culture has been reinforcing that belief. We say, “Job creators, entrepreneurs, these are the people who make America great.” So there are people walking around with substantial wealth who think that they have it because they’re better. It’s fundamental to remember that you’re just a member of the human race, like everybody else, and there’s nothing about your money that makes you better than anyone else. If you don’t know that and you have money, it’s the road to hell, no matter how much stuff you have around you. [...]
What lessons did your parents teach you about money?
My mom was somebody who really liked having nice things, like Chanel suits. She would spend money on things that she really, really loved. But she also dressed like a slob, and she would be more delighted by a deal on toilet paper at the supermarket than any Chanel suit.
This is often true of rich people, isn’t it?
Yes. A lot of people go back and forth between these identities. My parents’ financial life changed in the ’80s, and I was an adult by then and I watched them kind of relax into it. I think of it as slouching into money. They were in their 50s and they liked the shortcuts that wealth gave them. It’s very hard to say no to things like that. But what ends up happening is you end up being surrounded by people who don’t tell “no,” ever. And as my father’s drinking problem grew, he was surrounded by people who wouldn’t say, “You have a terrible drinking problem. You need to go get some help.”
You don’t have to answer this, but I’m trying figure out how much you inherited, or a ballpark if you’re not comfortable talking about it.
Well, and the number has changed over the years. I’ll tell you this: I could be a billionaire if I wanted to be a billionaire, and I’m not because I don’t want to be a billionaire. That’s an insane amount of money. But it’s the easiest thing in the world to make money if you start with money. And then people give themselves credit for being that smart when they’re not. [...]
Has the way you spend money changed?
I think that people who grow up in this kind of life go one of two ways. They either go the Kim Kardashian route, which is spending, spending, spending, completely absorbing the idea that, “Yes, you are that special,” and wanting everyone to look at you. Or, and I know a lot of people who’ve gone this way — especially my women friends — you do the opposite. I wore shitty clothes around. I didn’t want anyone to know what I had but money is morally neutral. It does not, in and of itself, make you a bad person. It also does not, in and of itself, makes you a good person. You are who you are and the least important thing about you is what you have. That was not, “You haven’t earned it,” you know. So my philosophy is you try to earn it in reverse.
What’s that dynamic like? Do you see other wealthy people and think, “Oh, you earned your money, whereas I was given it”?
I certainly have an inferiority complex around people who have actually earned their money. I did grow up with this doubt about myself. Like, did Yale really say yes because I was that good, or did Yale say yes because of my last name? I’ll never know. I’ve spent a lot of time earning things like post graduate degrees that make me feel legitimate. And those feelings have started to go away. But that’s outsourcing your sense of self. That is handing your self-esteem to the world to tell you whether or not you’re allowed to have any. And that’s a dangerous game.
I’m curious if you have any friends that aren’t wealthy, and how you found them.
Oh yeah. That’s actually a hard thing to find. The way I did start to form really strong relationships was when I went on the board of the New York Women’s Foundation in 1992. They described themselves as a cross-class alliance of women helping women across New York City, which sounds very canned, but honestly it’s exactly that. And that’s where I began to form relationships with people who were very different to me.
I remember this wonderful Korean lady came over for a meeting at my house, and the next day she called me and she said, “You didn’t offer me a glass of water.” And that never crossed my mind, but I have to be conscious of the fact that people who come into my home are coming into a place that feels daunting and intimidating, and I need to go to the extra mile to make them feel welcome. And I didn’t know about that until someone just came out and said it to me. Just like I watched my father increasingly surround himself with yes men, I started to deliberately surround myself with no ladies. And so they would, a lot of the time, really jerk my chain, and that was important.
Is it hard to trust that someone is interested in you for you, if there’s an inequality there?
That is the worst. And I have gotten a really good radar about that. There are people where you can practically see dollar bills in their eyeballs when they’re talking to you. And they are not bad people. How you feel about money is greatly related to how you were raised, so I don’t hold that against you, but I will keep you at arm’s length. I can’t be an idiot, but I would rather be duped from time to time — and pay that price — than become a person who lives in mistrust. When I get duped, I just chalk it up to the rent I’m paying for not living on Planet Suspicious.
They did a study at the Chronicle of Philanthropy years ago where they asked people who inherited money, “What amount of money would you need to feel totally secure?” And every single one of them, no matter what they had, named a number that was roughly twice what they inherited. So that’s what you need to know about money, right? If that is your primary measure of success or value in life, then good luck with that, because it will never feel good.
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