Clay Cockrell always knew he wanted to be a therapist. But growing up in small-town Kentucky, raised by a father who made a living salvaging auto parts, he never imagined that he’d specialize in treating the superrich — or “ultra-high-net-worth individuals,” as he calls them. That changed after he set up his practice in Manhattan and started seeing a wealthy entrepreneur who passed Cockrell’s name around his inner circle. Eventually, Cockrell embraced his niche, and today all of his clients are part of the one percent.
While Cockrell now has a unique understanding of what the rest of us might consider “Champagne problems,” he tries to keep a healthy distance. “I’m in their world, but I’m not of their world,” he says. “In some ways, I’m a reality check for my clients, and I think they like that.” Here, he discusses dealing with entitlement, teaching his clients how to make non-rich friends, and the right way to talk about your private jet.
Why do you think very wealthy people like to work with you?
I started my practice about 20 years ago. And about five years in, I had a client who was a very successful entrepreneur, and he wanted to work on issues of how money had complicated his life. That was my first time being exposed to this world, and I had to check my own biases. He had been to therapists in the past who didn’t get it, and who had a lot of negative judgments toward him because of his financial success. The attitude was basically, “Why do you have these problems? They should be solved.” And obviously they weren’t. They were real for him, and I respected that. He liked working with me, and then he passed my name to other people around him. These are people you can’t really market to directly. They’re very guarded because they’re used to people wanting things from them. But through word of mouth, more and more utra-high-net-worth individuals started coming to me, and I got to know the specific issues that they were facing.
Tell me about your own background relating to money.
My father owned an auto-parts salvage business, and I watched him expand that so he was able to put my brother and me through college. But we were very middle class, blue collar, from a small town in Kentucky. Then I moved to New York in my 20s, right after grad school. My wife is an actress and we need to be near theaters. So I started and built my practice in Manhattan. Most of my early clients were white-collar professionals, but not on the level that I eventually worked with. There’s not a lot of men in my field, so I’ve always had a lot of male patients. I was seeing a lot of anxiety, a lot of depression, a lot of job issues, relationship issues — the basic things you could imagine a therapist deals with.
What are some of the biases you had about wealthy people that you had to get past to work with them?
Like many people, I had operated under the fallacy that money is going to solve all your problems. And I was shocked to find out that not only does it not solve your problems, it causes a lot of problems. It also makes things more extreme — it turns up the volume.
You’re probably familiar with the idea that once you get to a certain level of income, your happiness kind of levels off. If you go from $35,000 to $70,000, you’re going to feel great. But going from $70,000 to $140,000 doesn’t have the same effect — you’ll be a little happier, but not in the same way. Once I learned that, I could start to understand why someone could have $100 million and still not feel like it was enough. There were also a lot of challenges I just hadn’t thought about before. Like, how do you raise a kid in a moneyed environment and instill character and ambition and purpose? These were issues I’d never encountered, and I had to keep an open mind.
What are some other problems that your clients face that are totally alien to the rest of us?
Well, I should preface this by saying that there’s a lot of people out there who are very wealthy, who love it, and who are enjoying it. Those people don’t come see me. So I have a skewed view of this world. But one of the biggest problems I see is isolation. A lot of my clients have difficulty relating to someone who does not have their resources. For example, if you wanted to talk about your weekend, when you took your private jet to Paris to try out a new restaurant, how are you going to explain that to a doctor, a lawyer, or a plumber or whatever? So you’re constantly monitoring what you say and what you do, knowing that you don’t relate to the common man.
To try to solve that problem, a lot of very wealthy people hang out with other very wealthy people because it feels more natural. They don’t have to worry about picking up the check or raising eyebrows about their lifestyle. And then they get very isolated in that world. Eventually they realize, My money is either fucking me up or fucking my kids up, and I don’t have the tools to deal with it, and I need to talk about it because money has complicated my life to a point to where it’s not fun anymore.
Do you find that a lot of wealthy people are paranoid about other people taking advantage of them?
I see a lot of caution around new people. It’s hard to make friends. There’s a lot of, Does this person want to get to know me because I’m interesting, or is it because I’ve got a lot of money, a lot of access, a lot of fame?
I coach people to have some rules and some phrases in your back pocket so that if someone asks for a loan, or a donation, or an investment in their business, you know how you’re going to respond. You can say something like, “I’m sorry, I’ve allocated all my charity for the year already,” or whatever feels natural to you. You have to construct a sort of net around yourself so that you don’t have to worry, If this comes up, what do I say? What do I do?
How do wealthy people decide whether or not to broadcast their money? Not everyone wants to hear about your private jet.
Well, it depends on the person. But here’s an important distinction: There’s a difference between private and secret. Secret is dirty, right? It’s shameful. Whereas private is appropriate. You want to embrace that difference. If someone asks about your weekend, you can say, “I tried out this great restaurant,” but you don’t have to give all the details because you want to keep them private. Or you can be loud and open and say, “I’ve got this great jet and we took it to Paris and we came right back, and it was amazing.” Every person has to find their level of comfort in what they disclose. It takes some experimentation.
Once you begin to accept your own story and your own resources, others will either get onboard or they won’t — that’s not your responsibility. Everybody’s got their issues with money and that’s their business. So you have to deal with your own issues, not try to compensate for other people’s.
Do you find that your clients with inherited wealth have different problems from those who didn’t?
There are two buckets of people that I deal with: people who have generational wealth and grew up in it, and people who came into it suddenly — maybe there was a liquidity event, they founded a company, won the lottery, whatever. They don’t have the same tools to deal with it that the people with generational wealth do. It’s two very different populations.
For those who come into wealth suddenly, it’s particularly jarring because they have resources that are often very different from their friends and family. It’s like, “I want to take our friends to Madrid for this wonderful weekend, and I’ll pay for it, but is that going to make them feel awkward?” They have to learn how to talk about these issues, and gauge other people’s comfort levels too. It’s a skill set. Money changes people’s lives, and talking about it helps other people navigate it too, because they don’t know how to bring it up.
Is there any lifestyle stuff that makes you blink now? Do you really feel like you’ve heard it all?
I’ve heard a lot. It’s been a long time since I’ve been, “Whoa. You did what? With what? And you crashed what kind of Ferrari?” But if I’m ever shocked, I don’t have a very good poker face. In some ways, I’m a reality check for my clients, and I think they like that.
I imagine that very rich people might worry that people only like them because of what they can afford to do. How do you deal with that?
A lot of people wonder, If this were to all go away, would I have any friends? It can make them have really low self-esteem and a lot of self-doubt. They struggle with the fear of, People don’t like me for me; they laugh at my jokes because I’m paying for dinner. A lot of them keep their old friends very, very close for that reason and have trouble making new ones. Sometimes they have to learn how to have those uncomfortable conversations of, “I’m happy to pick up the check, but sometimes I want you to pay.” Or, “Let’s do something that doesn’t involve paying for anything.”
How do people go about that when they’ve become so insulated?
I often encourage people to get involved in charity work. A lot of people write a check; they don’t go build a house. So I say, “If you’re going to be involved in a charity, get involved. Not just board meetings. Go and ladle out some soup. You need the benefit of having contact with other people who are different from you.” A big part of my job is helping people get uncomfortable.
How do you manage entitlement? It’s such an unattractive trait.
I definitely see a sense of, I deserve this. If someone built a company and made all this money, they might say, “I did this. Why, homeless person, didn’t you just work harder, too? I don’t need to feel sorry for you.” Even people who inherited their money, they often feel like they’re special in a way.
When I hear that, I encourage them to break it down. What is it about you that makes you so special that you do deserve this? Give me the proof. Having money can lead to certain opinions and outlooks that aren’t based in reality. So it’s about holding up a mirror. Sometimes that works, sometimes it doesn’t. And of course, sometimes you have to be delicate.
There’s a lot of shifting attitudes toward rich people, depending on what’s going on in the world — sometimes they’re admired, sometimes they’re hated. Do your clients seem to be aware of this?
Oh yes. They know it. When I first got into this, it was 2006, 2007, when the wealthy were very much admired. People aspired to be like them. And they were used to that. Then, very quickly, after 2008, I was hearing a lot of, “I’m demonized. People don’t like me. They’re out to get me. What’s with this Occupy Wall Street?” A similar attitude shift happened again during the pandemic. Now the tide is turning back to admiring wealthy people again, but they have that scar tissue of worrying that people hate them. There’s some tenuousness. Like, “Can I show off my diamond bracelet again, or do I still need to keep it in the vault?”
That’s probably not a bad thing.
No, it’s not. It’s important for people to take accountability for their money. I hear a lot of, “Why do people hate me for having success, or for something that was out of my control? So my grandfather created this oil company; so what?” And I try to get them to dig into that more.
Do you see people who keep their money almost entirely secret?
Yeah. Absolutely. And there can be so much shame around it. Many with over $100 million are still thinking, One day I’ll have enough to where I’ll feel safe. There is a fear it could go away and they won’t have any skills to take care of themselves. There’s this helplessness — “I couldn’t possibly get a job. I don’t have any skills.”
Your rate, $600 a session, is listed publicly on your website, which I appreciate. And that is high, but in the range of New York City therapists, it’s not astronomical. How did you determine your rate, and why don’t you make it higher if your clients can afford to pay it?
One, I look at my own need. And two, the fee is part of the therapy. When I was first starting out, I was charging people $25 a session or even nothing at all. And what I noticed — and I’m not the only therapist who will say this — is that if you charge too little, people don’t value it and they don’t participate. If there’s a small pain point in the cost, then people are going to show up and commit. So it seemed to me like $600 was enough. For a lot of my clients, they don’t care. But I hope it’s enough for them to say, “Okay, this is an investment. I’m going to do this on a regular basis. I’m going to do the exercises he gives me, try to make some changes.” I don’t know if I’ve got it right or not, but for now it seems to be working.
Does being exposed to so much wealth ever make you envious or mess with your own spending choices?
Yes, definitely. I have to remember that I am in their world, but not of their world. At the end of the day, I have routines to get back into my own life. I write up my notes and play with my dogs and go for a walk.
I’ve definitely done stupid things, though. Like, once I bought my wife a diamond bracelet that I thought was $4,000 — which would be a push for me already — and then it turned out to be $9,000. I had misread the nine as a four. I stood there, went through the whole process of feeling shame that I couldn’t afford it, followed by, “Well, that’s not that big of a number. My client spent that on dinner just the other night.” So I went ahead and bought this stupid bracelet because I had a temporarily skewed sense of reality. It took me a while to pay off, but lesson learned. It’s a very nice bracelet.
Have you ever dealt with someone who came by their wealth through something nefarious, like a Sackler or something? And if so, how did you cope with that?
I haven’t had any arms dealers or anything. Now I’m worried about it because you brought it up, but I suppose I’ll cross that bridge when I have to.
There are definitely people who have guilt and shame about the source of their wealth, and that’s a big part of their therapy — coming to terms with it. Accepting that this is not something that they did, but something that has happened to them, especially if they’ve inherited this money. The question is, do you want to do something about it? Do you want to give back to people who were impacted by the aggregation of this wealth? Do you feel a responsibility to that? Most people who come to me understand that giving away all their money wouldn’t solve all their problems. But there’s this perception that wealthy people should do that: “If you have a problem with it, just get rid of it. Give it to me.” That’s a simplistic view. Nobody’s going to do that.