Married into wealth: Reflections on a life made 'easier, not necessarily happier’

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With an MBA and more than 25 years in finance marketing, Kelly Willis Green already knew a lot about wealth, investments and philanthropy. While she was chief marketing officer of a leading Toronto wealth management firm, she helped create a success story with more than $4 billion in managed assets.

But when she married real estate developer Robert Green six years ago, her role in the world of wealth stewardship became more personal. Today she is known in the family-office industry as a “married in,” someone who joins a wealthy family by marriage. She soon discovered firsthand that it’s a complex business, managing one’s own wealth and philanthropy, not to mention the emotions that come with.

Last year, she changed up her life upon retiring from her job as a marketing executive. She launched a podcast called Serious Coin, which covers the facets and responsibilities of wealth for the greater good, and, more broadly, the emotional connection that people from all backgrounds have with money.

In a broad-ranging interview, Willis Green spoke with Canadian Family Offices about the emotional impacts of living with wealth, the visit from an art dealer that led to her podcast, the myths that surround super-affluence and the all-too-human insecurities that just never go away.

On your podcast, you talk about how hard it is to marry someone with considerably more wealth when you’re a proud independent woman, and a success in your own right.

Exactly. It was especially an issue when we were dating, because I was determined to kind of match him stride for stride. We’d go out and he’d pay, and I’d want to pay for the next. We did that for some time. And he wasn’t comfortable with it, because he knew the reality of the situation. And over time, even though I had engineered that, I wasn’t comfortable either. I was even vaguely resentful because while I was trying to make things fair, I realized it wasn’t fair, given the difference in our net worth.

But I didn’t want to lose my independence or perhaps give up power. So we started to have conversations about that. Initially there was a certain level of discomfort.

Was it an awkward conversation? It seems like there is a lot of emotion around money and what it means.

Definitely. I think that’s why feelings beneath the surface can lead to resentment or the feeling that this is maybe unfair, until you talk about it. It was that interview [on the podcast] with Dr. Jamie Traeger-Muney, where she talked about how to have those conversations. You’ve got to have courage, and a certain curiosity. So, ‘What is it like for you?’ You can ask these questions, not in a threatening way, but out of curiosity.

Does it start with our parents, the way we communicate about money?

Absolutely. Our beliefs and behaviours are mostly subconscious, until someone goes through the practice of bringing them into the light, as I did. I took a money-coaching course years ago, and the most valuable thing was coming to understand how I viewed money in my life, and recognizing some of the patterns I had.

Can you share some of those patterns? Tell us about your upbringing.

On balance, I had a pretty healthy relationship with money. I grew up in a home where my parents were quite frugal. When I read The Millionaire Next Door by Thomas Stanley I recognized my parents.

My father was a third-generation business owner, and my mother was a teacher and a homemaker. I guess we were modestly affluent, you could say, but my parents were very frugal. I learned at a young age that one’s self-worth and net worth were in no way correlated. And the idea of keeping up with the Joneses was disdainful, so much so that spending on material goods was frowned upon. To the extent my parents had indulgences, it was mostly vacations, experiences and real estate. Simply put, the message I got was spending was bad, saving was good, and investing was better [laughs]. All good habits.

But on the other hand, I think even now, sometimes, my husband and I, both having grown up with middle-class values, struggle to fully enjoy the advantages that we have.

You come from a middle class background, and then you “married in.” I hear that’s a thing?

I guess it is! Until I heard that from my family office advisor. I did not know that was a term. In my case, it may have been a little different, because my husband also grew up middle class and is first-generation wealthy. So I was not marrying into a system of wealth. He was experiencing increasing affluence as the business grew. He just had more time to get used to it than I did, and he created it, which of course was different.

Dr. Traeger-Muney, whom you interviewed on the podcast, said there is shame around having money and yet there is no one to talk to about that. It’s very much a First World problem.

It’s interesting, I maybe have a different perspective coming from the wealth management industry as I have, because you talk about it every day with your clients and among your peers. Certainly it’s not something you face with your friends. And people are very reluctant to talk about it.

But at the same time, it is a life event that happens to some people. In my case, I’ve married into it. I’m not special. I’m not deserving of it. But I’m also not deserving of some of the other things that happened in my life.

Previous to meeting my husband, I had been widowed. My late husband, Skip Willis, died in January 2011, and that was a life experience I had, and I was not deserving of that either. I guess I’m intellectually curious, and in my grief I wanted to learn about it, read about it and study it. I took a course on it and trained to be a grief group facilitator, started a blog for widows, and spoke at conferences. In other words, I shared what I learned and what I was going through for the benefit of others.

I am doing the same with wealth. I created the podcast to get people talking about it and share, and maybe in that process we will debunk some of the myths, demystify wealth, create a more balanced and maybe healthier conversation around it. I don’t think anybody wants to hear tiny violin problems from the wealthy, but at the same time, I find just talking to people at dinner parties or wherever, that people are really curious about what other people with money are doing. They are to a large degree worried about how they pass money on to their kids, their grandkids, and when I talk about a podcast on wealth they do lean in and are often willing to share their angst around some of these issues.

Did you find that your friendships changed?

No. My friends are still my friends. The challenge when you marry later in life is you have your friends, and your husband has all his friends, so you are meeting new people, and that changes how much you can see your friends. But I can’t say I’m gravitating toward people to share ideas around wealth or anything like that.

What motivated you to do the podcast?

I think people are curious about the subject. For me, that idea took hold and wouldn’t go away. It really is the culmination of my professional experience and body of knowledge I’ve developed about wealth, as well as my lived experience.

The first time the idea came to me, we had built a home a couple of hours north of Toronto and we had bought a painting. The gallery owner where we bought the painting drove up one Friday morning to hang the painting for us. (I assure you I did not grow up in a home where gallery owners were driving to hang paintings for us.) In the course of doing that, we started talking about art. I don’t have an art background, but I was so curious about who his clients were, and how they approach investment in art, and we had a very engaging conversation, and I thought, ‘This conversation shouldn’t be taking place in my hallway. It could be something that other people are interested in.’

People are curious about what other people are doing, what they can learn from them, what best practices are, both the practical issues of wealth as well as the philosophical or emotional issues.

And are you interested in real estate?

I do love real estate. In Season 1, I did an episode on buying real estate in London.

I listened to that. Was it in Chelsea that you bought?

It was. London being a global centre, it has a lot of appeal. And it’s a very different market and process for North Americans to buy into, so I thought it was interesting to explore.

Is that a hobby, real estate?

I would say it’s a hobby. My husband’s passion is art, so I told him if you keep buying more art then we need more walls [laughs]. But I don’t think either of us is interested in having more homes, quite frankly.

You also have an interest in philanthropy.

I’m exploring that as well through my podcast, and personally. I want to keep getting better at it.

We try to focus on organizations where we have some sort of personal connection, maybe someone we know and trust is on the board, or the charity is an area of focus for us, such as financial literacy.

What has been one of the bigger challenges of having significant wealth?

It feels inappropriate to discuss challenges, because I will be the first to say it’s been wonderful, full stop. It’s made life easier, not necessarily happier. I was happy before. Wealth just made it easier. You can explore new interests, and it opens you up to new experiences.

But there is a lot that it doesn’t change. Life is remarkably the same. If you were living with debilitating chronic pain, money doesn’t change that. If you or a family member has an addiction it doesn’t change that, or if you are dealing with aging parents that are a worry.

Money might be able to provide resources to deal with those problems, but you don’t always have control. I think it certainly is a challenge to manage it well and not be seduced by it, and at the same time enjoy it. To find a balance is something everybody has to come to on their own.

Has it ever made you feel guilty?

‘Uncomfortable’ is a better word. I generally don’t think guilt is very productive. I go back to what I said earlier about I am no more deserving of this wonderful life event that has occurred than I was deserving of the most tragic life event that occurred.

So why feel guilty about this? Sometimes it can be uncomfortable to have advantages that others do not. That’s why I try to remember to contribute in many different ways. I think there can be some discomfort with having resources and knowing that not everyone does.

In our culture, when you have fame or extreme wealth, people think you’re magical and you’ve got the answers.

That is the big lie. That’s what I was trying to say, that life is remarkably the same. You know that expression, ‘Wherever you go, there you are.’ And except for one guy I guess, there is always someone who has more. In some circles you might feel uncomfortable because you have more, and in other circles you have much less. I remember very early in my career, we had some clients who sold a business and came into let’s say between $30 and $50 million. They wanted to know whether they were wealthy. And I was tasked with going through the numbers around wealth because they wanted to know where they fit, because it seemed to them everyone they knew was living with tremendous wealth.

So they wanted to know where they ranked. Did that strike you as odd?

Yeah.

So no matter how much you have, they fear it’s not enough?

That’s definitely the case. I read something recently in The Atlantic about research done by Harvard Business School professor Michael Norton, and right across the wealth ladder, millionaires and even billionaires said they needed two to three times more to be happy.

Isn’t that human nature to a degree? Maybe it’s everybody’s task to try to tame that monster.

This interview has been lightly edited and condensed.

More from Canadian Family Offices:

• How to equip kids with healthy attitude toward money, a step-by-step guide
• In wealthy divorce, why bad behaviour never pays
• When money isn’t an issue, new retirement concerns bubble up
• As ‘godfather’ of family offices in Canada, Tom McCullough and his vision stand test of time

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