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Fifty thousand dollars. That’s what guests paid to visit Fantasy Island, the mythical retreat and namesake of the late 1970s-early 1980s TV show. The money bought visitors fulfillment of their dreams, though Mr. Roarke, the island’s host, eventually decreed that everyone should be able to have fantasies come true on the isle, regardless of how much he or she could pay.

There was no Mr. Roarke on Greenaway, the real-life island outside of Stamford, Connecticut where Sue Gilbert grew up. Gilbert didn’t need one; her family enjoyed extreme wealth. Cadillacs, furs, jewels, servants: all this and more played a part in a childhood where no one whispered a word about money. The veil of silence around just how wealthy they were caused Gilbert, later in life, to examine the pros and cons of financial abundance.

Part of her analysis of family and money led Gilbert, a filmmaker, to release “Greenaway” in 1982, a documentary that featured interviews with her parents discussing life on the family estate. Time’s passage led to more questions: How did her siblings feel about class? Along with their monetary wealth, what values had her brothers and sisters inherited? Gilbert realized another film was in order. A sequel of sorts, “Beyond Greenaway: The Legacy” came out in 2009, featuring sit-downs with her siblings talking about abundance, family and what it means to be rich.

These days Gilbert lives on the Eastside, on Yarrow Point, which, while not an island, is still exclusive. Along with filmmaking and creating art, she conducts “The Legacy Workshop: Exploring the Intersection of Money, Family and Inherited Values,” where participants examine their belief systems about wealth. Amid the bustle of an Eastside Tully’s Coffee, Gilbert recalled her childhood, the difficult situations her wealth created for friends, the need to tax the rich and the guilt some wealthy people experience over their financial bounty.

What was your childhood like?

In many ways, my childhood was absolutely idyllic in that we had enough money to be able to have beautiful surroundings. My parents had a beautiful home and great gardens and they could afford art. I grew up in what appeared to me to be a fairy tale castle.

On the other hand, there was the element that they could afford to have people raise us. And so we didn’t have a huge amount of parental contact. We weren’t even allowed to eat with them until we were 13. So there was quite a separation in terms of the kids and the parents. And I think that was in some ways difficult: You felt—and there were six of us—you kind of felt like you were a number.

Where did you eat and where did they eat?

Well, they ate in the formal dining room and we ate in the little breakfast room. And when we were really little, we ate up in our rooms, in the nursery. We weren’t to be brought downstairs until we could properly sit up at the table without a highchair.

How big was this house?

Huge. It probably had 20 rooms and had a staff of about six full-time people. It was huge. Just huge. Part of my work has been to accept that part of my upbringing. I went through a time where I was really ashamed about it—my parents, the excess—during the sixties. How popular was it to be wealthy in the sixties?

So when did you realize that you had this excess, that you had access to it?

I realized it when I was in high school. People would come over to my house and it was their reactions. I began to have to prepare them for coming over, for what to do in certain situations and the fact that, when we did eat with my parents during the teenage years, you couldn’t bring up anything personal. And by all means, it shouldn’t be anything left-wing politically, because that could set heads rolling. I realized that other homes were not like that, there was a lot more freedom. And a lot more interest in the kids. Not that our parents weren’t interested, it was sort of a remote “How is that section of my kingdom doing?” rather than “How is this part of me doing?”

So tell me about Greenaway.

Well, it was an island—it is an island. It has a different name now. Three and a half acres at low tide. It had a main house and it had several outbuildings. It had beautiful gardens. And it was surrounded, of course, by the water and that was the most beautiful part about it. It was also a metaphor, in a way, for being wealthy and unlike other people. But we were connected to the mainland by a bridge. So we went to school and had playmates across the bridge. It was pretty idyllic. The bridge was really—I’m really not good with distances—half the length of a football field. So not that far. From the windows, the views were quite far away.

All right. [Laughs.]

What are you thinking?

What I’m thinking is that it’s so beguiling that someone lived on an island.

I know. It was magical. Beautiful.

Did you feel removed from most people?

No. I didn’t feel removed because of the island. I began to feel removed because of the extreme wealth. I began to feel there was a huge difference between my parents’ lifestyle and other parents’ lifestyles. A quantitative difference. Both my parents were born in 1907. They were Edwardian and in their generation, wealth just flowed. You didn’t question it. You were happy that it was there and there was no—How do I put this?—you were never taught how to handle it, how to be wealthy or not be wealthy.

When you say “wealth,” what do you mean? Is there a number?

I mean extreme wealth. I don’t know the number. That was back then, so the numbers would be skewed, but it was extreme wealth. Not a [Bill] Gates situation, but there are categories in wealth and it was up in the higher categories. Millions and millions of dollars.

Where did this wealth come from?

Through my mother’s side of the family. It was acquired in the Industrial Era through smart investing on the part of my great-grandfather who grew up very poor, and needed to really support his mother at a young age. He discovered the whole process of leveraging money, that you could actually lend somebody money and make money on it.

So, extreme wealth. I mean, you’re living on this island, but did you own a Rolls Royce? What were markers of it?

My mother was really showy, I thought, in terms of her clothing. She would change clothes everyday for dinner. She looked stunning. I think what was embarrassing to me was her penchant for fur coats. So even when it was mild in the spring, she would show up in a school conference, the only mother in all these furs. And I was embarrassed because I thought that was ostentatious. I let myself be embarrassed because she wasn’t like the other moms, dressing quietly and conservatively. She was just wearing honking jewelry, because she loved it. She was the same way at home. But as a kid, that was embarrassing.

Did you find that people treated you differently when they found that you had this background?

I did. I think this was the hardest thing. I went to boarding school at 14, which was my choice, and I loved the camaraderie. The other thing I enjoyed was there was an anonymity to it, nobody knew each other’s backgrounds. You were just whoever you were. No one was ever aware of who was on scholarship or who wasn’t on scholarship. We all wore the same clothes.

When the sixties hit us in college, I had my friends turn on me and say, “You’re really bourgie, you’re really wealthy. You need to give it all away.” It was very confusing for me, because I’m also a humanitarian, so I could see their point. On the other hand, I wasn’t sure that I should give it all away. I had to really wrestle with it. And my parents were no help. We never discussed money. I was very hurt that some of my friends, in following their values, shunned mine or shunned me. So I was really caught between two worlds.

You never spoke about money?

No. It never occurred to me. See, the other thing was I didn’t have a closeness with them. My dad and I never really had a relationship. He was the guy who came home, patted us on the head, then went away the next morning. He would have been the person to have talked to about money because, in a traditional way, my mother passed all the thinking over to him. That’s a big change now: People are really opening up about it. Part of my work is to help people open up about money, not to be so afraid to discuss the advantages and disadvantages.

It must be at least once a week I hear about how the gap between the poor and the rich continually widens. What do you think when you hear that?

Here’s the deal. I’m not an economist, so I don’t know what statistics they’re basing all that on. What I generally think is, I’m sad, because I think more people should be in the middle. I think it’s important for the rich to pay more taxes and even if Washington were to institute a state [income] tax, I think it should begin only for people earning over a certain amount and then really hit them. Taxation is a way of equalizing things. People don’t like to pay taxes because people don’t like where it’s going. But we elect the government, we are the ones that have a say.

[She looks at me.] You are grinning over there. What are you thinking?

We have a concept of people who are wealthy. And to be pretty frank about it, it is that people who are wealthy are uptight, they are prigs, they’re selfish.

And ostentatious.

Totally. And they’re only looking out for themselves, because that’s how they got rich.

That last part, I wonder if that’s true. I wonder if you have to be greedy to be rich, I wonder if you have to be unethical to make money. I wouldn’t know if Bill Gates is greedy or not. I wouldn’t know if he’s unethical or not. Nobody tells you that. So in my Pollyanna way, I want to think that it’s possible [to] become successful without in any way being unethical.

I mean, I absolutely know how the rich are perceived and a lot of that comes from television. But no one gets into these rich households that are quiet, because they won’t let you through the gates. Even getting my brother in the film was tricky. He was very suspicious. And I worked on him. I sent him a list of issues and he said, “I’m in,” because he wants to help do good in the world.

The other thing is the rich are beginning to wake up. This is the good news. This film has pushed me to know more rich people. I know my family, but we’re all anomalies. We don’t hang out with a lot of rich people. I’m much more interested in values, because your money means nothing unless you have values.

I’m trying to be nonjudgmental because I think that’s where we’re hurting each other so badly ... the rich are a great resource to harness. There are so many big hearts. So many of us feel guilty. So when offers come in, “Can you help with this? Can you help with that?” or friends come, “Can you help with this? Can you help with that?” it’s a real privilege and an honor to be able to say, “Yeah, I can help you.”

This man I went to grad school with was so wealthy, he had his Rolls Royce shipped across the country. I was broke and I asked him for money and he wouldn’t lend me money. I remember being furious. So that was years ago, and now I realize, “I imagine a lot of people must ask him for money.” Do a lot of people ask you for money?

There are times when people are down and out that they ask me for money. But that is not an upper class thing, because anyone who has more than anyone can be asked for something. And what does it cost you to say yes? If you have this feeling of wanting to help people, that’s one benefit.

I had a friend recently who asked me to help her with a divorce. She started gambling the money she had and then she was in bankruptcy. Then she wanted to borrow money. To me, if you want to borrow money, what’s the exchange? Nobody likes to feel beholden. Interest is a form of exchange. She offered none of that. She said, “Oh, if we can get some money out of my ex-husband, who’s also in bankruptcy…” People need to learn how to ask for money and give it, both, graciously.

She was my best friend at the time and I lost her over the way it was handled. I said, “I’ll give you half, and as soon as I get a letter from your attorney stating that half of your retainer has been paid, I will send him the other half. That’s all I can lend you.” I did use the word “lend,” but I knew it was “give.” She was just furious. She claimed that I had betrayed our friendship.

Another woman, she was great. She said, “I will pay you back.” In the request, there was a plan how. I never asked for any documentation, because that’s her side of the bargain. Instead of interest, she said, “Can I come work for you once a week?” She worked for me for the better part of a year and when her divorce went through, she refinanced, she paid me back. It empowered us both and strengthened our friendship.

So tell me about these workshops.

It’s a way for people to massage their wealth. One of the questions I ask is, “How many of you want abundance?” Every hand goes up. I say, “How many of you want prosperity?” Every hand goes up. I say, “How many of you want to be wealthy?” they sit on their hands and they shrink. So I write on the blackboard, “Wealth=abundance.” You can be abundant monetarily, financially, you can have abundant good looks, you can have abundant singing talent, you can have an abundance of love in your life. And that is a kind of wealth.

So the point of view in my workshops is, “Why be afraid of too much?” If you get to the point where you feel you have too much, you know, the world needs that. There are a million organizations that need that, a million people. So why would you be afraid?

When’s the last time you’ve been to Greenaway?

Years ago when I was filming and I stood outside of the bridge with my film crew. Now they have gates across the island and I watched a truck go through and then we filmed the gates closing. My film is called “Beyond Greenaway” and you can never go back. I have moved beyond Greenaway. The family that owns it doesn’t use it much. They live in New York and they use it as a weekend place.

My workshops are for everybody, that’s the fun part of it. I don’t enjoy working with just the so-called wealthy. You wouldn’t believe it. Many of them won’t admit they’re wealthy. They may have two homes and I’ll say, “How many of you in here feel wealthy?” “God forbid you call me wealthy. That’s a dirty word.” But it’s only a word.

To learn more about the documentary "Beyond Greenaway" or to find out about The Legacy Workshop, visit: BeyondGreenaway.com

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