My Two Cents

Personal-finance columnist Charlotte Cowles asks the nosy, revealing, sometimes uncomfortable questions about money so you don’t have to.

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Iris Brilliant is a money coach who works with a niche clientele: “high-net-wealth” individuals — usually those with “access to $50 million and more in liquid resources” —  who feel conflicted about the money at their disposal. More specifically, she helps these people determine how to give that money away. 

And she would know how these clients feel: Brilliant was raised in a wealthy enclave of San Francisco during the ’90s and inherited money in her early 20s from her great-uncle. She thought about keeping her surprise windfall a secret, but instead she got involved in philanthropy — and eventually made talking about money her career. 

Below, Brilliant discusses the conflicts her ultrawealthy clients struggle with most, why even rich kids should have jobs, and how she coaches people to give away the money they don’t need.

You grew up in pretty wealthy circles and inherited money at a young age. How did that steer you toward this career?

I was raised wealthy in the San Francisco Bay Area during the ’90s tech boom, and my family was new money. I noticed our life changing as my father’s career grew. And as we became part of a more affluent culture, I was aware of this competitiveness in the air. It only grew more intense as my family became wealthier.

In my early 20s, I inherited money unexpectedly from my mom’s uncle. It wasn’t enough to live off of, but it was enough to make me feel extremely alienated from my peers who had debt from college. I could have kept it a secret and avoided it, like many of us inheritors do, out of shame and concern for my friendships. But thankfully, I found an organization called Resource Generation, which is a national nonprofit that helps young people with access to wealth or class privilege get involved in social justice work. It showed me how to reconcile these different parts of myself — and taught me that I didn’t have to keep my wealth a secret. Ultimately, I redistributed half of the wealth I inherited. And at present, I live off of what I earn.

I wound up working at Resource Generation as the national organizer for high-net-wealth people. Since then, I’ve become a money coach specializing in high-net-wealth couples and individuals who want support in figuring out what to do with their money, as well as how to talk to each other as partners about resources, power, class dynamics, in-laws, and the endless list of topics that come with access to wealth. More recently, I’ve also started to focus on parenting and some of the fears that the ultrawealthy have around not wanting to raise entitled children.

When you say you grew up wealthy, what did that look like?

One of my earliest memories was in kindergarten. We were basically auditioning for spots at this very competitive school, and we were being observed. I remember the adults watching me in a way that was different from how I was supervised normally, and I knew that something was expected of me. Whatever it was, I managed to deliver, because I got into that kindergarten. But it was the beginning of a kind of self-consciousness, a feeling of pressure.

What parents sometimes forget, and what I really try to teach my clients, is that children are constantly comparing themselves to their peers to make sense of the world. I started to notice at a young age whose house is bigger. I had one friend who had a fountain in front of her house, with a roundabout driveway, and I got the feeling of, Okay, this is kind of a “bad” level of wealth. This is too much, too ostentatious. I noticed who had a house to go skiing, and who skied and who didn’t. There were so many class signifiers that I understood to mean that some people were doing life “correctly” and some were not.

As my father started to acquire a certain kind of Bay Area status, we started socializing with the tech elite. When you’re spending time with billionaires, there’s almost a manic energy. You’re with people who know that they could enact whatever they wanted, so watching them get excited about ideas can be very intense. When I was a teenager, I accompanied my father to a philanthropic conference. When we showed up, they had these buttons laid out on a table where the name tags were. The different buttons had different colors, and you had to choose up to three buttons that you would wear next to your name tag. And the buttons signified different philanthropic causes — there was Africa, women and girls, climate, all these categories. And I could feel how dehumanizing and weird it was, and performative to put these buttons on. And I remember thinking, I never want to participate in something like this again, but there’s so much wealth and possibility here, so I have to engage with it somehow. 

Let’s say a new client comes to you. What concerns do they typically bring in?

A typical client might be a couple, and one of them inherited tens of millions of dollars and the other one came from a middle-class background. A lot of people are in cross-class relationships. But for the person who married into or partnered into wealth, having access to money doesn’t magically dissolve their own history. It takes a while to catch up with their present-day reality. They might be stuck in their childhood scarcity. Meanwhile, the wealthy partner is ordering all this stuff. They’re living on different planets in the same house. And when you have kids, you have to get aligned: Do we want to be the family that orders takeout every day of the week? Do we want to be the family who cooks? At the end of the day, what matters most is what you’re doing in your day-to-day normal life. What is the quality of your relationships, and what are you prioritizing? It’s not about what buttons you’re wearing at the philanthropy conference.

There’s a very popular opinion that wealthy people who inherit a lot of money and are conflicted about it should just give it away. Like, “Oh, if you just give it away, then your struggles and class anxiety would disappear, and you could get a job like the rest of us. Problem solved, and the world is better for it!” Please share your thoughts on this perspective.

There’s a kernel of wisdom and truth in that statement. That’s an attitude I also used to have when I was younger. And it’s worth holding onto, especially since there’s a big industry — it’s known as the wealth defense industry — that’s designed to keep wealth in place, especially for inheritors. Family offices, wealth-management firms, investment managers, all of that type of stuff. Their jobs are designed to keep wealth within families. If you are someone like me and you inherited a couple hundred thousand bucks, it’s a much different situation than if you inherit $20 million with a family office and shares in a family company. Maybe you’re going to inherit five different $20 million properties in the future that you’ll have to negotiate with your siblings, and your money came with a whole financial team that you didn’t choose. Sometimes inheritance is extremely complex. I think sometimes we overestimate the wealth holder’s level of agency in deploying resources.

Of course, sometimes we underestimate it as well. There’s always more that wealth holders can do. If you’re an inheritor, maybe you need to have a hard conversation with your parents and stick to your values when you’re working with your financial team. And I strongly believe that everybody should have a job if they can. It’s not out of a moralistic place; I don’t think having a job will cleanse you of your sins of coming from wealth or anything like that. But if you are able-bodied enough to work, it’s really important to try to work for a living and see what it’s like, and figure out what type of work you can offer, and have the experience of working with other people who are living off of what they earn. It’s an important part of participating in the world. For inheritors who don’t work, the level of isolation is extreme. It can take a long time to bring them back to reality.

You work with a nonprofit called the Enough Project, which explicitly helps ultrawealthy people give money away. Tell me how that works.

In the Enough Project, we work with eight ultra-high-net-worth people at a time over a six-month period to help them figure out their lifetime financial needs — how much money is “enough” for them? — and then help them give away the surplus. We support them in understanding how much money they want to move every year and make sure they have the right connections to philanthropic advisers and such. It’s enabled us to move quite a lot of money into the world, which is really exciting. Our cohorts tend to be a mix of Americans and Europeans. We also do one-on-one work with those who have access to about $100 million and up.

Do people ever give all their inheritance away and just live off of their regular earned income?

It is very rare. I don’t think any of my clients have given away all of their inheritance during our work together. Which isn’t to say they won’t at some point in the future. A lot of people are scared that if they give away too much, they’re not going to have enough money to meet their needs for the rest of their lives. And I’m often telling them that they’re going to be okay, and that they will probably feel better if they give away more.

I know you’ve also been part of a group that helps families whose wealth has Nazi connections reckon with that fact. That sounds extremely challenging. 

The Hour Before Dawn is a project I started for my own personal understanding, being a Jewish person who moved to Germany a year and a half ago and who’s partnered to someone with Nazi heritage. I have Holocaust history in my ancestry. The program is for European wealth holders who suspect or know that their family wealth is in some way connected to either the Nazi regime specifically or — we’ve broadened it recently — to fascism and European colonialism. We offer support in doing family research and family business research, as well as in creating a reparative giving plan. We’re moving money to address histories of forced labor. We’re also moving money into Jewish culture-building across Europe, and Jewish-Palestinian alliances, and toward organizations that preserve and fight for democracy across Europe.

How do you help young people at odds with their parents — or parents at odds with their adult children — about how to use their money?

I try to support parents in building trust with their kids. If you fundamentally don’t trust your children, you’re in for a lifetime of struggles. As with any conflict, you have to try to understand what it’s really about. For example, your adult daughter is getting married and you want her to sign a prenup. Is it because you fundamentally don’t trust her fiancé? Is it because you don’t want to lose control of her? Is it because you carry your own history of being exploited by people for your wealth? Is it because she’s never had a job and you’re worried about the gender dynamics in the relationship? When you boil it down, there is always some valid issue. Parents want their kids to lead healthy, happy, meaningful lives. And adult children want to be trusted. They want independence. They want to lead a happy, healthy, fulfilling life as well. Ultimately, we have the same goals, but we have really different ideas of how to get there.

When you’ve got this type of conflict, it’s about helping the opposite sides understand each other. And then it’s about making sure the financial systems themselves support that vision. If you’re telling your 25-year-old daughter that you trust her, but then you’ve created a trust fund that micromanages what she’s allowed to spend that money on and when she’s allowed to get it, then you’re communicating to her financially that you don’t trust her. You’re giving her mixed messages. I’m not saying the answer is to give every child unlimited access to resources. But consistency is key. I also encourage inheritors to demonstrate to their parents that they are working on their financial literacy so that they can gain their parents’ trust.

Can you give me some examples of mistakes that parents make when they pass along wealth to their children? 

I think the most common mistake is pretending your family is middle-class when you’re not. That is gaslighting. That’s misinformation. It is profoundly confusing. Of course, don’t go telling your 10-year-old your net worth. But once your kids are teenagers, telling them about your financial status is not going to create entitlement. It’s actually not telling them that creates entitlement. Because if you don’t acknowledge that your family is extremely wealthy, your children might assume everyone can afford to go on international trips every year and fly business class. That level of ignorance and naïveté will negatively affect their peer relationships.

Another mistake is rewarding children behaviorally with gifts. That’s something I personally experienced, and it is a guaranteed shopping addiction waiting to happen. I got a Beanie Baby for every little good thing that I did when I was a child. And let me tell you, I had a lot of Beanie Babies, and a lot of shopping-addiction issues I had to work through. A lot of rewards are well intended, but as children get older, it can become a form of financial manipulation. Like, “I will pay for your college, but only if you go to this college and not that one.” Or, “I’ll pay for your wedding, but only if you let me invite all of my business buddies.” Again, that instills a sense of mistrust that will be really harmful to your relationship long-term.

The last mistake is not talking about money in general. Every person should understand how to budget and how to invest. Even if you know your kids won’t ever need to budget because they are that wealthy, it’s important to teach them anyway, because budgeting is also about delayed gratification and moving toward a goal.

On the flip side, what are some mistakes that you see young inheritors make with their money? 

A big mistake inheritors make is keeping their wealth a secret from the people they’re in serious relationships with and from their friends. That secrecy creates shame. Everyone can have their own personal policies about how to talk about money and when, but you do need to talk about it.

Another mistake that young inheritors make is only being friends with other wealthy people. I think life is much richer and more valuable when we have a diversity of perspectives in our lives. And people really miss out on amazing relationships by limiting themselves to only being friends with people similar to them. Sometimes this was never modeled for them — their parents only hung out with people at the country club or whatever — but the majority of the world is working-class, so it’s actually very easy to meet people who aren’t wealthy. I also encourage people to widen their hobbies. If you’re only friends with people who ski or people who like going wine tasting, maybe get involved in another local organization. Broaden your interests, meet people who share them, talk to them, and work on those relationships.

What if people don’t feel like they can relate to you because they think you’re too rich to understand their problems?

I think the best way to have people not want to be your friend, as a wealth holder, is to lie about your wealth. First of all, it’s really obvious. I promise you, they already know. They know because you order appetizers every time you go out to eat and you don’t even think about it. They know because you take Ubers home. They just know. If you can talk about it and become someone who’s trustworthy in having conversations about money and about differences, that’s how you can make and keep friends who aren’t exactly like you.

Okay, speaking of appetizers, who pays for dinner? Where is the line between being generous and treating people in a way that might offend them?

I could write a book of all the mistakes I’ve made eating out with friends. Paying the bill at a restaurant is one of the most complex social dynamics imaginable. I think it boils down to consent. It’s about direct communication and transparency. Assuming someone always wants you to pay for them is not great. Sometimes you just have to have an awkward conversation: “Hey, obviously you know that I have money. I see that you’re working two jobs while we’re in school and it’s difficult. I would love for us to just have a policy that anytime we go out to eat, I pay for it, but I want to know how you feel about it, and I don’t want that to negatively impact our friendship. What do you think?” It’s also important to stress that you do not look down on the person who can’t pay. Sometimes there’s shame on the receiving end, which is something that took me a really long time to learn.

But please, if I could just leave you with one thing, it’s this: If you are wealthy, do not ever send a Venmo request for something that costs under $50, minimum. Don’t nickel-and-dime people. It’s obnoxious. I knew someone who would send me these Venmo requests for $2 coffees. And I was like, “I know you’re wealthy. This is just rude. What are you trying to prove?”

Email your money conundrums to mytwocents@nymag.com (and read our submission terms here.)

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