How to Divorce Proof Your Marriage: Advice from Celebrity Divorce Attorney James Sexton
21 Nov 2025 · 93 min
Celebrity divorce attorney James Sexton talks through what actually breaks marriages: disconnection, fear of conflict, infidelity, substance use. He's handled billion-dollar settlements and argues prenups matter, clear communication saves money, and admitting your own mistakes beats fighting in court.
Questions this episode answers
$3 million (paid to Sexton over four years).
About $5 million (across multiple lawyers/firms).
Around $12 million (including his fees, opposing counsel, and expert fees).
About $800 million in assets (as stated).
Around $4 billion to one spouse; he said the husband had ~ $9 billion net worth and the spouse received around half.
Chapters
James, what's the most expensive divorce you've ever seen or been involved in?
I got paid $3 million from one of my clients over the course of four years. That's the most expensive one I've ever personally been involved in. The other side in that case paid 5 million across three lawyer or four lawyers, four law firms. Because I, I, I just kept picking them off like one at a time. And every time she would get a negative outcome, she would fire her lawyers and hire new ones. I was on it from the beginning all the way to the end. But yeah, she, she spent 5 million. I, my client spent 3 million, plus another million or so each in expert fees. So it was probably like, by the time it was all said and done, about a $12 million divorce, but for a couple that had $800 million worth of assets, you know, that wasn't as much money to them. He actually said to me with a straight face, that client, early in the case, we were talking about settlement concepts, and he said, well, look, I'm not going to argue with her over a couple of million bucks. I remember thinking, really? Okay, Because I, I argue a lot for a couple of million bucks. That's actually my job description. So, you know, that's, but he was very sincere. He was like, yeah, I'm not going to, I'm not. Who's going to quibble over what's a few million among former lovers? You know, wow.
And what's the most you've seen one side have to give away to another side in a divorce settlement.
Somewhere in the neighborhood, assets wise of about $4 billion. Yeah, 4 billion. Yeah, yeah. But that was, you know, a marriage of long duration. The guy had a net worth of about 9 billion. And, you know, he, she got around half of it because they, when they, when they got together, he didn't really have much and, and she had really, you know, raised their kids. And, you know, this is all New York is, is, you know, it's very funny. My colleague in, Laura Wasser represents, like, people you've heard of, you know, like, she represents celebrities. And anytime a celebrity is getting divorced, Laura's usually represents one of the celebrities in the, in the transaction. Phenomenal lawyer, Great, great talent in the courtroom and out, and a great, you know, great human being. The people I represent, you've never heard of. And they could buy those celebrities 10 times over. Like, they're, they're the ones who, you know, I, I had a client once say to me that, you know, when you go to an actor's House. There's pictures of that actor with other actors. And when you go to a producer's house, there's Picassos hanging up. And that's kind of like my clients. Some of them have a level of wealth that you couldn't even imagine. And I couldn't even imagine. But they are the most unostentatious. Like, they're just not ostentatious. They're very sedate. They drive a Jeep Grand Cherokee. They wear a Timex watch. They're not posh. They're just people who, they look like they're no one. And they could walk around in public and not have anyone recognize who they are. And yet they have a level of financial power that most of us couldn't even fathom. They can move markets with their trades.
Wow. So I want to get into all of this and your story in a moment, but I need to get a few of the fun questions out the way first.
Sure, sure. I love it. You're starting right with the juicy stuff. Yeah. But usually people want to work into that. And I kind of love that you skip the foreplay, Rob. Like, you're right there. I love it.
Straight in. So what about the longest or messiest or both divorce you've been involved with?
I mean, that 3 million one. That would, that would, that pops right to mind. I mean, because that was about a five year divorce. And it was, it was messy on every level. I mean, it, it, you know, what you, what you really look at as a divorce lawyer is you think a lot about what are. Somebody comes into my office. Like, very rarely does anybody come into my office and say, you know, Jim, I would really like this to be expensive and protracted and just awful. I would like it to just consume my life for the next several years. No one says that. They all say the same thing. I want to be fair. I want to be fair. And their spouse is probably in another lawyer's office saying the same thing. The problem is they have very different definitions of what's fair. Right. So this is, this case, you know, would have been like if you wanted to teach in law school. Every complicated thing that could make a divorce ugly and protracted. It was like a perfect storm of all of those. There were substance use issues, There were closely held assets. There were complex ownership structures of, of their, you know, because, look, super wealthy, you know, the ultra wealthy do not function the way that normal people function. They don't own very much. They, they have an interest in a trust, and the trust owns an, and the LLC owns a Percentage of ownership of a piece of real property, like their, their structures are very complicated. Like, you know, I've had cases where people have generation skipping trusts where their grandchildren who haven't been born yet have a net worth of in the billions because they've put all of their assets into these complex trust structures again for wealth preservation and tax avoidance. So when you get into that sphere, that ultra high net worth sphere, divorce, those things you do to preserve wealth and to avoid taxation, make a divorce extremely complicated because you don't own those assets anymore. Your grandchild who hasn't been born yet, owns those, those assets. So now it turns into a very complicated, you know, transaction. So that, that was the, the, the ugliest, most protracted are the ones that have complex issues that require levels of nuance and a very kind of competitive storytelling. And the problem is, like Joseph Stalin said, like, the death of one is a tragedy and the death of a million is a statistic. You know, if, if you only have a certain amount of money, if you have a couple of million dollars, you're not going to want to spend a half a million dollars in legal fees because it's a significant portion of your net worth. If I said to you right now, Rob, you're never gonna believe it, I just heard you've won $27 million. And then I went, I'm sorry, I'm sorry, I got it wrong. 25 million. You wouldn't go, oh, I was excited for a minute There, you know, 25 million, 27 million, are you kidding me? It's a massive amount of money. I mean, this is great. This is great. The first million's the hardest. So the truth is, like a lot of these people, you know, the money doesn't mean anything anymore. It's numbers on a page and it's a weapon to hit your head, your spouse over the head with, you know, and, and that's really all it turns into. So those are the cases that get very protracted. But divorce is so emotional that without question, like there are people who would spend, you know, ten thousand dollars fighting over, over a five thousand dollar bank account just because, like, just because you, that's why, you know, just because they, they want to stick it to this person so bad. And I've had people who I like, listen man, you're going to spend $20,000 arguing over this, you might as well just give her the 10,000 she wants and they'll go, no, I'd rather pay you. I like you better than her.
So there's loads of this I want to get into. But one thing I'm really fascinated in is what do you perceive that you do? So you're a divorce lawyer. Do you perceive that, you know, you're a lawyer or that you save people or what do you Definitely don't save people.
Yeah, I would say what do you perceive? Yeah, I, I'm a full contact storyteller. I manipulate people's emotional state for a living. That's what I do. I, I and I think that's true of a lot of professions. Like, I think a salesman manipulates a person's emotional state. But, but mine is a very specific kind of manipulation. I want the judge to feel good about my client and bad about the other side. I want my adversary to feel scared. I want opposing client to feel afraid or greedy. I want my client to feel safe. So I'm trying to manipulate a lot of people's emotional state in a very high stakes chess game where all of the pieces have different values and that, you know, I can only control some of the variables. So I would say I'm, that. I've also described myself as a weapon. You know, I think a good lawyer is a weapon. A trial lawyer, a good trial lawyer is a weapon. We, a weapon in the hands of a good person can protect things, and a weapon in the hands of a villain can cause chaos. And I'm hired to do both of those things at differing times. And sometimes I don't even know until I'm kind of halfway through, oh, okay, I'm representing the villain. You know, because no one comes in and says, oh, I'm the villain. People come in and they say, oh, no, this is the facts of my story. And then when you start to get to the bottom of it, you go, okay. But the way our adversarial system works is that each person is entitled to the most vigorous defense within the bounds of advocacy. And, you know, sometimes the truth has a way of coming out, sometimes despite my best efforts. And I take a lot of comfort in knowing that the truth tends to come out even sometimes despite my best efforts.
And so have you ever had any moral conflicts? Then when you're halfway through a case, you're like, shit, I'm representing the villain. What do I do here?
Well, I know what I do. I never have that last part. I never have the what do I do here? What I do here is my job. Like, that's my job. You know, my, my, my. There's a line from Rissus Sardonicus that I've, I'VE read and reread so many times that I have it by memory. And that is, I have resigned myself to temporary complicity with evil in order to accomplish certain strategic objectives for people whose suffering is more important than my need to maintain moral purity. And I. I take a lot of comfort in that. Like, my job, I. I'm not like, the world needs bad men. We keep the other bad men from the door. Like. And so my job is, Is sometimes to protect people and to facilitate, you know, the goals of a person who's a good parent who wants to take care of their children and wants to, you know. And sometimes my job is to represent an agent of chaos and help them, you know, leverage their children for financial benefit in the context of a divorce proceeding. Like, and, and the way our system works is that I am not supposed to be the one to judge. The judge is the one who's supposed to judge. You know, my job is to advocate on behalf of my client. And I, I don't. I represent my client and I represent the system. I don't always believe in my client, but I always believe in the system. And so I. I have times where it is painful emotionally on the inside for me to represent a person and vigorously advocate for them because I. I believe that they're not a good person or that they don't have noble goals. But I. It doesn't stop me from doing my job because I. I know I take my job seriously. I take the oath that I took very seriously. I. I think there is probably a African American heart surgeon who probably has had to do surgery on someone with a swastika tattoo, and they probably go, no, my job is to save this person. I don't care if I'm going to save them. And they're going to go on to hate me and to be a horrible person. My job is to save them. I took an oath and I treat it the same way. My job is to play the role I play within the system, which is to represent my client to the best of my ability. And I do that. I don't cheat. I don't break the rules. I want to win or lose a fair fight, but I'm going to fight very hard. Wow.
So you said at times you feel very emotional. You know, if you face the villain, what are those emotions and how do you deal with them?
It's a great question. I try in my real life, in my personal life, to maintain a real level of calm and simplicity for someone who works in such a high conflict, high communication, fast Paced environment in my private life, I'm, I'm very calm. I'm very quiet. Quiet. I'm, I, I don't, I don't, I don't allow a lot of chaos in. I, I'm not, I don't like, take pleasure in debating politics. I'm not a guy who's going to get worked up if you cut me off in traffic. Like, all right, you're probably more of a rush than me. I fight for a living. So I think when you fight for a living, you tend to not do a lot of it in your private life. So that's a piece. Another piece of it is that I, I, I, I just understand my place within the context of the system, so I, I'm very comfortable with that. I mean, I think it's, look, it's hard to do the job sometimes. There are days where, where it's heavy on me. It's heavy on my heart to do what I do. But, but I'm usually not doing one case at a time. There's usually like five or six cases all happening at a time. And so at least one or two of those, I'm representing someone I really believe in. And in some ways, by the way, that's much scarier. Like, it's much scarier when you represent a person who, you know you're right and, like, you really want to win for them, you know, in an emotional way. Like, I want to win for all my clients, but some of them I know don't deserve to win. Like, what's scary is the person that you really know, they deserve to win. And you just need this judge to get it. Like, you just need this judge to hear you. And that's, that's much more frightening to me. And how do I do that? You know, I, I really just try to, like, you know, take it one task at a time. I, I don't, you know, I'm very clean in the way I live. You know, I, I, I exercise. I, I do, you know, I, maybe I'm a bit of a cliche in that I do, like, the saunas and the cold plunge and stuff like that. Because I do think, like, facing those extremes has been always very helpful for me. I do Brazilian jiu jitsu. That helps a lot with stress and, and on the jiu jitsu mat, you're really not. No one cares what you do for a living. Like, no one cares how much money you have or who you represent or what, you know, they just want to know, do you know how to do that joke and do you do it well, and if you're good at it. All right, let me see you do it, you know, so I love that. And in my private life, I take a lot of comfort in, you know, I have dogs, I love my dogs. I have deep friendships. I have a very rewarding relationship. I. I'm very grateful, you know, I'm very grateful for the life I have. I really try to be who I am at work, when I'm at work, and I try the rest of the time to. To not be that person. I'm. I'm at work most of the time, so I'm this person most of the time. But I enjoy when I get to.
Step out of that character as a divorce lawyer. Have you ever been divorced yourself? I am.
I am divorced. I am. I describe myself as happily divorced, but if. If anyone's divorce is like mine, if everyone's divorce was like mine, I would be out of a job. I would have to go do something else. Because my ex wife and I were college sweethearts. We met when we were 18. We got married at 22. We had kids at 24, and we divorced, you know, when the kids were 5 and 7 in a very friendly way. And we've remained very dear friends. Our sons are 25 and 27 now, and one's a lawyer, he's an assistant district attorney in the Bronx, and the other one is a sound engineer. And, you know, they love their mom. She's been remarried for, I don't know, 15 years, something like that, and to a great guy who I consider a friend. And, you know, we're very lucky. Like, we're very fortunate. We love our children. We've always loved our children more than any negativity between the two of us. We've never set foot in the courtroom. And I don't think it's because she was afraid to be in a courtroom with me. I think it's because we just are both people that, you know, we. There's a lot of people I love I wouldn't want to be married to. You know, I. I think that she loved me, and I loved her, and I still love her, and I think she still loves me, but not in the way that. That you're meant to love someone. I mean, the way we explained it to our kids when they were 5 and 7 was, you know, mom and I don't love each other the very special way that married people are supposed to, but we both love you, and we were always going to be a family. And, and we made good on that promise. You know, my, my older son just got engaged and she and I were chatting about, you know, being excited for the wedding. And I have so many clients that like, their kids getting married is such a trauma because it's like, I can't, I can't be in a room with this person, much less standing next to them in a picture. And I just don't have that. You know, I'm very blessed that my ex wife is a friend to me and someone who I love and admire and her husband is a great person who I admire and care for deeply. So, you know, I'm very lucky. But, you know, listen, I, I, I never, I'm a good ex husband. I don't think I was a great husband. I'm impatient. I love my work. I don't think I love anything as much as I love my work. So I don't know what that says. You know, that's just, I, I have the gift of, of being able to do a job that I'm really passionate about. So I think it's hard for, it's a hard act for any woman to follow.
So I want to come to the loving, you work bit because I'm an entrepreneur and I work every day, no days off ever. And you know, I have a massive entrepreneur community. So I want to pick into the entrepreneur specifically. But I do want to ask you, because I think this is a nice way to approach a difficult subject, but how do you have a happy divorce? Like, give us some steps that people can take to have what you call a happy divorce.
Yeah, yeah. I mean, it's not possible for everybody. I always say that a divorce is like a table with four legs. You've got you and your lawyer and her and her lawyer. And if one leg is off, it doesn't matter how nice and straight those other three legs are, the table's gonna fall down. So, you know, whenever people would say to me, like, oh, how do you and your ex wife do it? I'm like, she's a really reasonable person and I'm a really reasonable person. And we both concede the possibility of our own error. And we both consider that, oh, well, where's my culpability in what disagreement we have? And am I hearing this other person's perspective and am I letting my ego get in the way? I mean, all of the things I would tell anybody to do to try to have as reasonable of a divorce as possible are very basic interpersonal communication. Things like, you know, listen to what the other person is saying, and really try to get out of your own ego and get out of your own way and understand where they're coming from. Credit the things they're saying as coming from a place of, of love or intelligence. If they're wrong, rather than try to point out why they're wrong, like, help them come to that by, by, by asking questions of it. Straw man, steel man, like all the classic things that anybody should do. So I think the, the most reasonable thing you can do is figure out how to be reasonable yourself. You know, there's a, there's an old Zen parable I don't know if you've ever heard, where a woman goes to a, a monastery where there's a very renowned, you know, monk and, and thinker. And she brings her son, who's a little overw. I want you to tell my son to stop eating candy. And the monk looks at the boy and he says, okay, come back in a week. So she's a little confused because she took a long trip to get there. But she leaves. She comes back in a week. She waits on the line again and she gets to the front of the line and he looks at the boy and he says, stop eating so much candy. And the mother says, I'm sorry, what. Why did you make me go away for a week before you just came back and said the thing I asked you to say. And he said, because a week ago I was still eating candy. And so I think that the lesson of that for me is look at yourself. Like, look at how you're interacting with your co parent. I think that you have tremendous control over your own emotional state and your own communications. We're much more powerful in that regard than we think. And the mind is a great servant and a terrible master. So I think you have to approach it that way. And Schopenhauer said that we make the mistake of thinking that humans are, are, you know, thinking machines that sometimes feel. I think we're feeling machines that sometimes think. I think we're mostly emotional. So I think you have to get that in check about yourself. And then, and then you can figure out how to navigate the emotional state of your partner, of your co parent, of your soon to be ex.
You don't come across as someone who's like, skeptical and beat down about humanity where, when you must have seen pretty much every dirty and evil thing about humanity.
So how.
Yeah, just talk about that.
I think those things are a natural segue to each other, to be honest. I, I think, I think when you spend enough Time, like, I, I represent the abused and I represent the abuser and I represent the person who's married to someone with substance use issues, and I represent people with substance use issues. I, I represent great parents and I represent absolutely awful parents by any objective metric. And you come to figure out that, you know, the world, like, there's human emotional complexity. Like, I just, I don't like, hurt people. Hurt people. You know, if someone's a perpetrator of abuse, they usually grew up in an environment where there was abuse, you know, like, so I, my experience of people has been, it doesn't make me love them less. Like, I, I'm not cynical, you know, I, I really believe that, that, that, you know, the, the parts of our hearts that are weighed down with hatred and that are, with, you know, anger and things like that are, are the parts that are broken and hurt, you know, and, and, and there's plenty to break and hurt anybody in the world, you know, So I, and I see a lot of it, I have my hands in it a lot of the time. I facilitate some of it, as you know, but I, it hasn't changed my look of. On humanity. It hasn't changed my view of love. It hasn't. I, I think there's something really shocking to me that 56% of marriages end in divorce, and yet it's assumed that it's something you should do. And to add to that, that 86% of people who get divorced are remarried within five years of their divorce. Now that statistics, even more shocking to me, but also indicative of the fact that, like, we, there's something to this. There's something in us that wants it. Like, there's something in us that goes, yeah, no, but I want that. Like, if I told you there's a 56 chance you're gonna hit in the head with a bow when you walk out of the door. You're not going to walk out or you're going to wear a helmet. But marriage, like, of course, like, oh, of course you're going to get married. Everyone's going to get married. Why wouldn't you get married? You're not going to get married. You must have intimacy issues. And what are you, 56% guys? That's crazy. You know, there's people that go, I won't go skydiving because there's a one in whatever tens of thousands chance, okay, this is a 56% chance that it's going to fail. Fail to the level that you quit, Forget another, what, 10, 20% that stay together. Miserable for the kids because they don't want to give away half their shit. So now you got a technology fail 76% of the time. That's crazy. And yet I get it. I get it. I go to weddings. I get misty eyed at weddings. I love it. I love cheering for them. Like, yeah, of course. Yeah, of course you try. Give it a try.
Have divorce rates gone up in your career since you started?
They've gone up and down. I mean, I've been doing it 25 years, so when I started, they were at a high because the economy was at a high. And. And it's very interesting, like, moderation is. Is actually good for marriage. Like, boredom is in. In like a societal way. Boredom is really good for marriage. Like, when. When things go really badly, you know, there. There's. There's a spike in the divorce rate because it's like people lose their jobs and people. You know, but there's also the counterbalance of nothing unites like a common enemy. So, like, in the early months of COVID there was filings happening because everyone was like, oh, my God, you know, we got to keep it together and, and like, the kids are home, and we got to figure that out. And, you know, but then there was, of course, after Covid, you know, restrictions change. There was a massive spike in the divorce rate. And some of that is that people were like, hey, I said for better or for worse. I didn't say for lunch. But, you know, some of that is also that there was economic stress that were placed on things. And when the economy is in a boom. When I started in the early 2000s, the economy was in a boom. It was before the subprime crisis hit. The real estate market was going through the roof. Everybody's house was worth more money than you could imagine. And you could go into a bank with a. With a piece of crayon and say, I need a loan. And they'd be like, here's a million dollars against your house. Here's a third home equity line against your house. And so money was going crazy. So people were like, hey, listen, I can afford to leave. I can afford to give you half. Okay, I'm going. Or they're running around having affairs, having a good time because they had money to pay for the hotels or pay for the girlfriend's jewelry. So, you know, I am in a recession proof industry. It's fascinating. When the economy is good, we're busy. When the economy's bad, we're bus. When the economy kind of stays mellow, then we're we're still busy, but we're not as crazy busy, let's say.
Wow. And what are the main triggers and causes of divorce? And maybe are there a couple of silent ones in there that catch people off guard?
Yeah, I mean, the big things that people talk a lot about are the sort of nail in the coffin, final marriage killers, like adultery, infidelity, you know, financial impropriety and financial stress. Those are the. The big marriage killers. But I. I've always said that. That those are a symptom, not the underlying illness. The underlying illness, in my opinion, is disconnection. That people just. We fall in love really fast, and it's like an instant connection, attraction, all those wonderful things, and then we fall out of love. You know, it's kind of like, you know, how do people go bankrupt very slowly and then all at once, you know, and that's kind of how people fall out of love, is they. They go very slowly, they disconnect and they start to fall apart. And then at some point, something just pushes it, and it's like, that's that final. You know, like, it's the final raindrop responsible for the flood. It's the final. Like, there is a snowflake that lands on the branch that snaps the branch. That snowflake is no heavier than any other snowflake. It was just the final one that was heavy enough so you could point at that snowflake and go, man, that snowflake broke the branch. No, all the snowflakes broke the branch. That was the last one. So I genuinely believe that it's disconnection. And I think that's caused primarily by two things that we don't. We don't know what we want, clearly, and we don't know how to say to our partner what we want. And we're afraid of little conflicts, so we avoid them and in the process, cause giant conflicts. You know, I. Look, you're an entrepreneur, and I've enjoyed your show, and I know that you are someone who leans into difficult things, right? Like, you're not someone, you know, you're like a, you know, a David Goggins in the sense that it's like, look, I lean into things that are hard. I trade what I want now for what I want most. You know, that's the nature of an entrepreneur. Is. Is. Is to say, okay, yeah, I know what would be fun right now, but I also know what I can invest in right now, what risk I can tolerate, what challenges I can tolerate in order to have the thing I want Most marriage is very much an example of that. It's about like, what do you want right now is going to be different than what you want long term? You know, you want depth of connection. So sometimes to have that, you have to have temporary disconnection. You have to upset your spouse from time to time in order to be your authentic self, you know, so that you can really be in the marriage and present in the marriage. So I think that people's fear of that is what leads them into my office. There's a straight line from when you start lying to yourself and then also by proxy lying to your spouse because you're not being honest with your spouse, because not being honest with yourself. And there's a straight line from that right into my office.
Wow. So onto us crazy entrepreneurs, are we more susceptible to divorce? Let me spit that out and say again, are entrepreneurs more susceptible to divorce? Are we nightmares to be married to? I mean, I think my wife needs an MBE in the uk, you know, some kind of badge of honor for staying with me for nearly 20 years.
Yeah, yeah, yeah. If she'd killed you should have been out of jail by now. I mean, you know, 20 years, a long sentence. You know, entrepreneurs are unique. I represent a lot of, of of entrepreneurs and business owners. And what I'll tell you is the thing that makes them most, their, their superpower is also the thing that makes them challenging as spouses and challenging as clients, and that is that they have to have a risk tolerance. Like, you cannot, like, if you want, safe, you're not going to be an entrepreneur. Like, entrepreneurs leverage risk in exchange for opportunity. Like, that's all it comes down to. You know, and I represent a lot of, of people with a level of risk tolerance that I do not have in my personal life at all. You know, and, and it is sometimes shocking to me how much risk they're willing to take and therefore the rewards that they're able to receive. And every entrepreneur has a relationship with risk. And so divorce, you know, marriage, if marriage is about stability, consistency, reliability, showing up for someone, you know, those are great traits for an entrepreneur to have, but they have to be hedged against a risk tolerance, a willingness to think outside the box, a willingness to be creative, to have a big imagination. You know, the old saying of, of, you know, talent is hitting a target nobody else can hit. Genius is hitting a target nobody else can see. And that's what an entrepreneur, entrepreneur has a vision, and they believe in that vision. And very often they believe in that vision more than they believe in anything, like, more than they believe in, in they have a relationship with that vision, you know, and that vision, like the entrepreneur mindset, is about purpose, passion, and profit. And it's. It's usually purpose and passion. And the profit's like the side effect. Like most successful entrepreneurs, the money's how you keep score. It's not. You're not doing it for the money. How many watches can you own? How many cars can you own? How big can your house be? You know, it really is at a certain point about, you know, achieving something, building something, creating something, turning a vision into something real and tangible. So, you know, again, those are some skills that, if used the right way, can make you a phenomenal parent, a phenomenal partner in a romantic relationship. You know, if you're an entrepreneur, you're used to delegation of responsibility. If you're doing it right, you're used to putting management in place if you're doing it right, so you know how to incentivize people. You know how. So, like, entrepreneurs can be phenomenal if you view your marriage as one of your entrepreneurial enterprises. You know, like, I'm going to commit time to this. I'm going to be disciplined about it. I'm going to make sacrifices for it. I'm going to accept certain risks in exchange for potential rewards. I'm going to listen to the customer. I'm going to look at the market. I'm going to change as conditions require me to change. I'm not going to stagnate and lock in. Right. Like an entrepreneur locks into a vision, but they don't get married to, like, the specific way. When market conditions change, when competitors change, when. Then they go, okay, we got to shift on the fly. I got to recognize and adapt. That's. That's the recipe for a good marriage. So I will tell you, I don't think I see as many entrepreneurs in my office as I do company men and company women. People who work for a big financial institution, people who work for a big company. C suite executives. I see a lot of those. You know, they're. They're. I think they have a level. I mean, this is speculation. I'm gonna sound like I'm trying to be Freud here, but I think they have a different level of control. There's something about the entrepreneurial mindset that is very much like, I'm gonna eat what I kill. Like, I'm gonna rely on myself, and I'm gonna go out and build a thing and rely on myself. And. And. And as someone who started a Law firm with a $5,000 loan, you know, and, and some money I'd put away by waiting tables for a long time. I, I had nothing, you know, and I built it into a multi million dollar firm with multiple locations and I represent some of the wealthiest people in the world and I'm, I'm possibly the best known divorce lawyer in the world. And I wouldn't say I'm the best one, but I'm, I'm well known. And you know, that just came from being hungry, you know, and wanting to be passionate about doing my work and, and doing it well. I wanted to do it well every day and I still every day want to do it really well. And so, you know, I think entrepreneurs have a certain mindset that is very conducive to marriage, but when they get divorced, it's a complete train wreck because, you know, a, they often have very hard to value assets. You know, they often have what we call a key man discount applicable, which is like, I couldn't sell my business to someone. My, I am my business. Like I can't say, oh, thanks for hiring Jim Sexton as your lawyer. By the way. This is Bob Smith. He's going to actually be doing the trial. No, there's only one of me and I can train people. I've taught a lot of lawyers and I have great people who work for me. I'm very blessed in that regard. But like when it comes to the actual hands on courtroom stuff, they want me, you know, so it's, it's, there's limitations to that. It's scalable only to a certain degree. And when people divorce, I think who are entrepreneurs, that risk tolerance that's made them a good entrepreneur can make them a challenging client because they're willing to roll the dice with big things and, and divorce is, is big stuff.
Is there a type of job or career or place in the world where the divorce rates are really high?
The divorce rates are pretty high in America. They're fairly high in the uk. The, the Asia does not have the level of divorce that the European countries have. The more religious the underlying nature of a culture is, the more divorce is often frowned upon. So like Ireland had, you know, almost no div. It was impossible to get divorced for a period of time. And the divorce rate's still quite low. UAE very low divorce rates partly because it's a very religious based society. You know, divorce rates are, are complicated in the sense that it's a statistic of how many marriages end in the very specific legal thing of A divorce. There's also people that just go out for milk and never come back. Like, there's also people that just. Just leave their marriage. They just split and then they, like when people remarry.
Divorce, you mean?
They just don't get divorced. They just move on. They just leave, you know, and, and, and that's, that's a pretty common thing. So if you create too many barriers to exit, people just do that, you know. But there are countries like, like Poland, for example, still has a fairly substantial Catholic underpinning within the country. So divorce is frowned upon. But the question I have to ask myself, and there is no way to answer it, is, you know, what's the marriage satisfaction rate? Because I'm not really interested in, like, you know, guess what? You managed to stay married and absolutely miserable for 50 years. Great job. Like, I don't. I don't know. I just don't think that's good. I understand that there's, you know, people that would say, well, the Bible says otherwise, the Quran says otherwise, and okay, I get it. But, you know, I don't believe that, you know, the purpose, like, the, the goal of life is to tiptoe through life and arrive safely at death. Like, I, I tend to think that life is meant to be lived and you're meant to find joy. And, and I'm not suggesting that we should be hedonists and that the only thing that should be our pursuit is pleasure, but I, I definitely don't think if, I think if you're miserable in a relationship that there are 8 billion people in the world, you know, the chances are you, you may have someone else in that other 8 billion that might give you joy and that you might give them joy. So it's just kind of a weird if there's 8 billion people in the world and you happen to find your soulmate at the college you went to, like, that's a hell of a coincidence, you know, So I tend to think that, you know, divorce statistics, although they're interesting and anecdotal, and they do tell us something about our level of, like, the triumph of faith over reason that we keep trying at this thing even though we suck at it as a system species, you know, I, I don't think that they're that important.
How do you deal with a really toxic, difficult ex?
You know, rules. I think rules are good. I think that you have to train a difficult ex like you would a puppy. You know, I, I say this to clients at the risk of being disrespectful. To their ex spouse. Because by the time you get your divorce settlement or by the time you finish your trial, you've been in my office for six months, a year, two years going through it. And so you never really want to see lawyers again. Like, you've spent so much money on lawyers, you've been in court or negotiating tables so many times that you're just like, oh my God, I don't want to do anything. So you're. If you have an obnoxious, you know, obstreperous, difficult co parent or ex spouse and they immediately start violating the rules, you know, either the rules of your agreement or of the order that was issued by the court, it's perfectly natural to go, I'm not. Whatever. Like it was, she's 30 minutes late. Who cares? Like, I'm not going to do anything. But, but that's a little bit like. And I'm a dog person. Like, you get a little puppy and you want it to sleep on its puppy bed, but then it like whines and cries and it wants to get in bed with you. So you're like, all right, it'll shut it up and we can get some sleep and you put it in Beverly, that's fine. But you're gonna have a 90 pound German shepherd sleeping in your bed. And, and let me tell you, it's a whole lot easier to train a little tiny puppy than a 90 pound German shepherd. So like, you can I get it when somebody says, you know what? I'm not going to go after her for these dumb little things. Okay? But then you're teaching a sort of lawlessness. So my feeling is you have to train them like a puppy. You have to hold them to rules. You have to tell them if you're, if you're going to play games that I'm going to take you to court. I'm good. They're going to be repercussions for it so that early on they figure out, all right, you know what, I'm not going to play games with this.
Have you noticed any major red flags in people that, you know, make them major candidates for divorce? I mean, maybe it's a green flag for, you know, your law firm, but.
That's right. That's right. I've identified my customer base. You know, I think we divorce the person we marry. And I think that, that, you know, we, there's a lid for every potential. You know, I think that it's really less about the individual character. I mean, of course I could say to you, like, people who are, who have too much narcissism or have narcissistic personality disorder, or people with borderline personality disorder, or people with serious substance use issues. Of course they have a difficult time with relationships. People who are very impatient have a hard time with relationships. People who have very poor communication skills often have, like, these are all red flags. But, you know, it's also about finding someone that's complementary to you. Because I know people that the things that attract them to someone are kind of the opposite of things that would make for a good marriage. Like, I, I, you know, you've been married a long time and I imagine you and your wife are not the same personality wise. And that's. There's a polarity that I think people need to have. Like, I'm so hard charging that I need a partner who's like, okay, let's just chill. Like, let's just, you know, and I'm so like, you know, I'm. I want to be Beyonce all the time. And someone's got to be Destiny's Child, you know, like, somebody's got to be like, you can't all be Lionel Richie. Somebody's got to be the Commodores. Like, you, you have to have someone who's the main character and people who are willing to be supporting presence. And those people are incredibly important. You know, as an entrepreneur, you, the people on your team are incredibly important, you know, So I think sometimes what would appear to be a red flag, it may be something that requires a polarity, you know, Like, I think that what's right for one type of relationship, you know, might be like, some person's trash is another person's treasure, you know, so someone who's not terribly motivated and someone who's, you know, kind of like, chilling. Yeah. If you're looking for a partner who's hard charging, yeah, you're gonna have a hard time, you know, but if you're the kind of person who's like, you might want someone like that. Like, the things that make for a good boyfriend or girlfriend might not make for a great husband or wife. Like, I know a lot of people that are like, you know, yeah, he was a musician, you know, and it was so cool. And, like, he got backstage, I would go backstage and I would meet, okay. And then he's on the road like nine months of the year, you know, and you're alone a lot of the time. And if you have a kid with that person, like, you gotta either travel with them all over God's green earth or you have to Say, okay, I'll see you in a couple of months. And then when the kids start school, like, I've represented the spouses of, of professional musicians or the professional musicians themselves. And you know, these people that sell out stadiums, but their life is a nomadic life. It's a, It's a challenging life. It's. Sure, it's sexy as hell, you know, A chef. I've represented some celebrity chefs, amazing chefs. Do you know the hours a chef works? They work every Mother's Day. Forget it. It's the busiest night ever. In, in restaurants. You know, they're, they're constantly. And what are they doing? They're in a restaurant, they're working in the nighttime surrounded by hostesses and hosts who are like young gorgeous people in their 20s think that's going to play out. And at the end of the night, they're exhausted. So what do they do? They have a couple of drinks with the other. I worked in restaurants. Couple of drinks with everybody who's in the staff. Next thing you know, people are in the broom closet. Like, this is how it works. So again, what you're looking for in a boyfriend or a girlfriend, it may not be the same as what you look for in a part. Look, you, you and I may get along wonderfully as friends, but do you want to go into business with me? You know, you do. You have those specific characteristics. There's a lot of people I love that I would not want to be married to because it's a very specific kind of relationship. You're. And we put a lot on it. Like, your spouse is supposed to be the best friend, best conversationalist, best financial partner, best roommate, best co parent, best travel. Wow. Wow. Do you have any other job in your organization that has a list of, Of. Of seeking candidate who. That reads like that? Because that's a hell of a list, you know, So I, I think, I'm sure that there are parts of your description of what you want in a person that only your wife can fit. And then there are certain ways that you are probably incompatible. You know, I like this music. She likes this music. She likes the mornings. I like the nighttime, whatever. But that polarity is, is enough polarity to keep it interesting, but not enough to make you antagonistic to each other, because that's what happens. The things that the polarity that makes us fall in love sometimes turns into the polarity that makes us resent each other and can't stand each other.
Even though you're a very successful entrepreneur, lawyer. Has it surprised you how Much. You've blown up on social media with your content.
It has, yeah, it has. It, it, you know, I wrote, I wrote my book a couple of years, actually like five years ago now, and I did, you know, some press for that. It was really the first time I'd done real press and I enjoyed it, but I didn't really think much about it because my job is such a demanding job time wise and, and it requires so much dedication that I didn't really think about, you know, wanting to build any kind of a media presence. And in the last year or so it's really blown up to the point where I, I kind of can't go anywhere without a few people saying, oh my God, you're the divorce lawyer. You know, they, some of them know my name, most of them just go, you're the divorce lawyer. The other thing I will say to you, Rob, is if you're going to blow up, don't have, if you want any anonymity, don't have the outfit you are in, in the videos that millions of people have seen be the outfit you wear every single day. Like, like I wear this five days a week. And so I'm very recognizable because I always wear a three piece suit, I always have my sleeves rolled up, I happen to have the tattoos. So those are, you know, the last remaining vestiges of a way, youth. And so I, I am very recognizable. So yeah, I never saw it coming. I still don't completely understand it. I, I didn't, it's very funny, you know, like whoever discovered water, it wasn't a fish. Like I, I would sometimes, you know, be talking to a friend and, and they'd say like, oh, you know, what are you doing this week? And I'm like, oh, I have this trial and they're like, oh, what's it about? I'm like, oh, my client was, you know, sleeping with the nanny and then he convinced his wife to have a threesome with the nanny and then the nanny ended up running off with the wife and they're like, like, what, are you kidding? And I go, oh yeah, I guess that is pretty, pretty crazy. That's like a pretty crazy story. But like to me it's like, you know, that's okay. Like that's just another story. It's like another, that's Tuesday. You know, like it's, you just see really, really crazy stuff all the time and every variety of human perversion and wackiness and you just sort of go like, oh yeah, you start to see the world very Different, I imagine I had a. I had a friend when I was younger who was a. Who was a stripper, an exotic dancer. And she said to me once that she had to consciously remember when she had answer her door to put clothes on because she was so used to being naked that, like, you know, like, there would be, like, a ring at the door and she'd, like, just go to open the door and she'd be like, I would forget that I'm completely naked. Because she was like, I spent so many hours completely naked the night before the day of the. And. And it's sort of like that for me. Like, I. I sometimes don't realize how shocking the things I see and do are. And if I. I don't end up talking that much about my work except in a media context, but I sometimes don't understand. Like, and then when somebody goes, oh, that's fascinating, I'm like, is it okay, all right, I didn't know. I didn't know that was so interesting. Like, when. When I did the first Soft White Underbelly interview with Mark Liotta that Now has, like, 6 million views and was really, like, the first thing that blew up, you know, and. And brought me to. To. To a lot of the other even bigger, you know, things I've done. I didn't understand why Mark wanted to interview me. Like, he. I had been a fan of Softwood Underbelly for years, and I love it as a YouTube channel. And when they. My secretary said, yeah, there's somebody named Mark from Soft Belly on. And I was like, oh. So I picked up and he said, yeah, I'm interested in doing an interview with you. And I said, you know, I'm not a fentanyl addicted prostitute, right? Like, this is. This is a wrong number. And he's like, no, no. I'm really trying to do more of, like, interesting people that have interesting professional lives or personal lives. So I went and just did it, and I just. Literally, it's like this. Like, I went in and just talked and, you know, I was just very blunt and honest. And next thing I knew, it was like, millions and millions of views. And I'm getting emails from, you know, from Lex Friedman and from Andrew Huberman and people who I really respect and admire for years. And I really had no idea, like, why. I really had no idea why it was. And what's interesting is, of course, you know, as an entrepreneur, like, people immediately want to, like, monetize this. You know, they're like, so what are you doing with all of this. And I'm like, I, I have a job. Like, I have a. I've been offered podcast deals. I've been offered, you know, all kinds of, like, I've had a number of networks offer me, you know, programs, production companies offer me programs. I've had a lot of podcast offers. And I, I have to tell people, like, no, no, I'm, I love my job. Like, I love the, I'm still doing the job. Like, this is, you know, the job is the priority. This is just sort of a side gig, you know, that I enjoy. You know, I enjoy talking about what I do because I'm very passionate about it. I like it. It's. It's not. I'm not selling anything more. I have more clients than I could possibly service. I'm very picky now about who I represent, and I, I probably do six, seven consults a week, and I probably take two new cases a month. So I turn away a lot of business. I refer it out to. Thank God there's a lot of people who do what I do and a lot of people who do it really well. But I don't even, I haven't even really grown the firm because I don't want to dilute what it is I do. I understand that people are hiring me for me, so. But, yeah, it's been crazy. I mean, it's really, it's wild to get to meet people whose programs I enjoy. You know, I, I've listened to you, I've listened to, To Diary of a CEO. I listened to Lex Friedman for years. Like, I, I, I, I jokingly tell people that I was riding the subway from Manhattan to Queens to go to a trial listening to Lex Friedman. And I got off the subway and went to check my email, and I had an email from Lex Friedman saying, you know, hey, I'm a podcaster, and I'd like to have you on. And I was like, this is really weird. I've been listening to him for the last hour and a half. So, you know, it's really surreal. I didn't see it coming, but it's a lot of fun. You know, it's a lot of fun to. And I'm very honored. You know, people come up to me like crazy and talk to me and say they like my work and, and it makes me really happy to know that, you know, that people enjoy it and, and find it interesting. Again, I, I don't think I'm as interesting as other people apparently think I am.
Well, I do.
Thanks, Rob. I appreciate it. But You're a salesman. So I don't know, you know, who can trust you? I'm a lawyer. You're a salesman. Who can trust each other. No, no. That's great. I appreciate it. I really do. I was looking forward to this.
So a lot of people say that, you know, money doesn't make you happy. I'm not sure I agree, but I'd love your take. So are the divorces worse, therefore, were the marriages worse, the more money that's involved? Have you noticed a money, marriage, divorce correlation or not?
Yeah, I have not noticed that correlation. What I'll tell you is I think that money can't buy happiness, but it can definitely upgrade your despair. I think that money, My mentor, Neil Postman in graduate school, used to say that money. Money offered real solutions to imaginary problems and imaginary solutions to real problems. So, you know, money can't solve the problem of loneliness, but it can, you know, provide you opportunities to be around large numbers of people that might feel like it's resolving your loneliness. It doesn't necessarily resolve the underlying, you know, issue. So I think, you know, I think it's kind of an improved means to an unimproved end. But as someone who's been broke, like, really, really broke, like, used to go to the diner with friends and I would eat their pickles in coleslaw because I couldn't afford to order anything. And I didn't, you know, I wasn't the kind of person to say, hey, can you buy me a burger? It's. It's much nicer having money. Money. It's great. I mean, it's really, really nice. Like, money's really useful in. In almost any number of settings. But, you know, I do think, as many people have said before me, who are smarter than me, that there is a. Like, there's only two amounts of money. Enough and not enough. That's it. And defining enough for yourself is really important. You know, I heard someone say recently that money's like gasoline in your car, that. That you don't want to run out of gas. But life is not meant to be a tour of gas stations. You know, I. I think that money is really important. And when people get a certain amount of money, like an abundance of money, there are certain stresses that that helps take away, but there are other stresses that it creates. So I. I have found in my experience, professionally, that when people lose their job and it creates financial stress on a couple, that can be very, very toxic. It can also be very toxic on a person to lose their job. Or to make a bad investment or to have a business fail because it affects their sense of, of their own self worth, you know. You know, as an entrepreneur, like we fall in love with our vision. You know, we fall in love with our vision the way we fall in love with our spouse. Like we, we, we, we can see it, it's right there, you know, and like that's, that's what an amazing entrepreneur mind does is it can imagine this thing and then it can see it and it can find the path to it, you know, but when that thing betrays you, you know, when through no fault of your own, you know, through market forces or competition or regulation, you know, the thing falls away. Like, you know, you lose a piece of yourself and you, you know, you, you can't help but be angry at the world or yourself or whoever. And who do we take our anger out on? You know, the people around us, the people we are with. So, you know, I think that money again can be, you know, it's a, it's a, it's a great servant and a terrible master. You know, I think that, that poverty is very, very hard. The divorce rates speak to poverty as an indicator for divorce. So, so, so socioeconomic struggle very often leads to marriage instability. I mean, that's what the statistics bear out. But the ultra wealthy also have a very hard time staying married. So once again, there's like a sweet spot. You know, there's a sweet spot of wealth without it becoming just, you know, ridiculous. You know, a ridiculous amount of wealth. And all that comes with that level of wealth also too, I, I observe because now I represent different kinds of people. You know, celebrity is also a whole nother thing. You know, there's, there's. If I was to, if I was to rank order what a person would want to be, you know, being, being famous but broke is really bad. That's the worst thing to be. Being broke and unknown. It's not great. That's not something I'd wish on most people. Being rich and famous is good, but the fame, you're giving something up, like you're losing something real. Like fame is the mask that eats into the wearer. I represent a lot of people that are not famous and they're really wealthy. And I, I have to tell you, if there's something to aspire to, that's the thing to aspire to is to be rich and not famous. Like famous is famous, puts stresses on things and makes things that used to be simple very hard. And again, levels of fame, like it's Love. I'm, I have a beautiful thing going right now. Like, I'll go, if I stand at Starbucks for too long waiting for my drink, someone will come up to me and go, my gosh, you're the divorce lawyer. And hey, how you doing? That's great. Okay, blah, blah. And maybe they'll say, can I take a selfie with you? Absolutely. Take a self. And that's it. That's not the level that, you know, like Brad Pitt deals with where he just can't. Taylor Swift. You just can't go anywhere. You have no privacy. Everyone feels like they need a piece of you and you owe it to them. And if you don't give them that piece, they think you're a jerk and they'll go online and tell everybody what a jerk you are. To me, that's really. I mean, I have so many clients who get falsely accused of, of, you know, infidelities or get falsely accused. They get sued for ridiculous things because they're just, they're that tall blade of grass, you know, that the mower is going to go for. So I think that wealth and celebrity, they correlate with marital discord. But I also think economic instability is very bad for marriages, too.
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That. I think that exists already. I, I think you, I think it, I think it exists in the sense that you wake up every day and decide to stay married, whether people acknowledge that or not. I think. No, I, I think people wake up every day and decide to stay married. Look, I think there could be a lease with an option to buy. I think that there's ways. Marriage, yeah, we can do, we can do marriage however we want. It's a man made technology gang. Like we came up with these rules, we can change them, you know, I mean, but that being said, the core component of that is not meant to be a cop out. The core component is you're, you wake up every day, you could, you could leave. Like, you can leave, give up half your stuff. Trust me, you're still okay. Like, you'll be fine. Like, so you're not there because you don't want to give up half your stuff. I hope you're not married because you don't want to get divorced. You're married because you like being married. You're married because you look at this person and you go, man, they add value to my life. And I hope I add value to their. You know, there's this beautiful symbiosis happening here. Like that's, that's why you stay married. That's a beautiful reason to stay married. But you choose that every day. Like, every day you wake up and just, look, I, I'll take a step further. I think every day I wake up and decide to be Jim Sexton. You know, you wake up, decide to be robbed. More like you wake up tomorrow and be like, you know what? I'm not doing this anymore, doing something different. I'm gonna just move to a different town and do a different thing. So I, I tend to, if we made this prison, you know, then we have the key, you know, to getting out. So I, I don't. But yeah, look, I think people could make renewable options. The problem is there's always second order effects. You know, they, they California did this interesting thing called community property. So their idea was because, you know, when you get married, you have all the stuff you owned before you were married, and that's what they call separate property. Okay. And then anything you acquire from the day you get married on that's marital property. It's presumed to be marital property. So if you buy your, your wife a Rolex watch, you bought yourself one half of a Rolex watch. Like you buy her a Birkin bag. You bought yourself one half of a Birkin bag because you're one person in the eyes of the law. So California had this bright idea where they said if you're married for seven years now, you're like extra married. You're like super married. You've been married enough, you've like mellowed into it. You've, you've truly, you know, you've truly marry married. Right. So now we're gonna have what's called community property, which is when you hit the seven year mark, everything you had before the marriage, it's all marital now. The whole thing's a big marital sandwich now. And the goal of this was to like increase unity, to just say, look, seven, the first seven years you're practicing at the thing. And then once you hit the seven year mark now you're really married. And there's no such thing as yours and mine and ours. It's our ours. What it ended up doing in practice is spiking the divorce rate at the six and a half year mark.
Wow.
Because what happened is that about the six and a half year mark, you know, the honeymoon's over. Maybe you got a kid or two, you've definitely smelled each other's feet and you go, okay, I got six months before everything I owned before this marriage comes into play, if we ever split up. And that is a weird wager to have to make. So, you know, that's, that's. I think there are potential second order effects to creating sunset clauses or like signposts that if you hit this number that you get to re up. Or you could cancel the contract. Like, it, it creates a real weird friction there. It's like a weird, you know, competing interests. And, and I, I don't know that that's true. I think it's better to look at your marriage as a choice you make every single day.
Prenups, do they work? Do they help?
Yes, yes, yes, and yes. Yes. Prenups are important. Prenups work. I mean, again, UK is a little different than the usa but prenups are binding, prenups are enforceable. Prenups are a good idea. What I tell people, and I will sing this from the, from the mountaintops till the day I die, is everyone has a prenup. It's either one that was written by the government or it's one that was written by you and this person that you allegedly like more than the other 8 billion people in the world. So who is more qualified to create the rule set that will govern your marriage? You and your partner, or this, the government? Because I have to tell you something. You've ever been in the Department of Motor Vehicles, You've ever been to a government institution? Have you ever looked around and gone, we should put these people in charge of everything? We should put these people in charge of my marriage and family life, for sure. I've never felt that way when I went to the Department of Motor Vehicle Vehicles or when I went to the passport agency. I have always looked around and gone, how are they making this so hard? Like, why can't you get some entrepreneurial mindset in here and have some increased competition and figure out a way to make this not suck? You know? Well, you have a prenup. You have rules that govern your marriage. You don't know them, but you have them. And by the way, the time most people learn them for the first time is in my office. So you're learning how to fight when you're already in a fight. Like, you're learning, you're learning about your rights and obligations when they're about to be put right in your face. That, to me, is. Is not a great way to do things. So I like prenups because I like a rule set. I like a game where I know the rule set and I like a game where we wrote the rule set and where we actually don't know how the rules are going to apply. So, you know, when they say, when you're, when you're trying, when, when economists are trying to come up with, like, an intelligent economy, you. You come up with one that you wouldn't. You don't know where you'd land in that economy, but you'd still think it's a fair system. Right? So it's the same thing with this. A prenup is at the beginning of a marriage. So if you go, look, I don't know when I'm going to be up or when I'm going to be down in this thing, but this is a rule set I can live with. I love that. I think that that's great. And I actually think it's also, you know, and this isn't me trying to push prenups because divorce lawyers, we lose more money on prenups than we make. Getting a prenup done is not expensive, and it. It prevents hundreds of thousands, if not Millions of dollars in legal fees if it's done the right way. But what I like about prenups is I actually think it's an invitation to have some really important discussions that people who are that committed to each other should be. Should be willing to have.
So, as maybe the most famous divorce lawyer in the world, who was the biggest narcissist, Amber Heard or Johnny Depp?
I'm gonna go Amber Heard on that one. Yeah, I watched some of that trial with great interest. I mean, look, I have to tell you, in a gunfight between those two, I was cheering for the bullets. I. I really didn't. You know, I thought they both just embarrassed themselves publicly and. And neither of them walked out of that trial looking good. But I. I have to tell you, I think from what I saw of that testimony, I. I haven't met Amber Heard, but I've met Amber Heard. Like, that's. She is an A type, and it's a type I've seen before. It's the type that threatens, that uses a disparity and an inequality in how certain aspects of the system treat gender roles and weaponizes it. And I am particularly disgusted by that because I represent. I have represented genuine victims of intimate partner abuse. And so when. When someone cries wolf, it is a really horrible thing because it really devalues the plight of actual victims of intimate partner abuse and domestic violence. That being said, I don't give Johnny Depp a pass for some of the boorish, awful behavior that came out at trial. I think that, you know, some of the ways that he was recorded interacting with her and speaking to her and conducting himself, he shouldn't be proud of that. I didn't get the impression he was proud of it. I think. I think he was someone who was struggling with substance use issues. And, you know, that came out that he's not perfect, but I think there's a difference between imperfect and, like, nefarious. And I felt. I felt that there was a mask that slipped a few times. I also thought, you know, Johnny Depp's attorneys did a phenomenal job. I mean, it's hard for me to watch a trial and do anything other than pay attention to the lawyering. And I think that there was some excellent lawyering going on there, particularly on Johnny Depp's side of the table. But, yeah, I mean, that. That was my take on that.
What particular good lawyering skills happened in the depth heard case?
I think on cross examination, Johnny Depp's counsel, lead counsel. I forget what her name is. She did A very good job of. You know, the worst cross examinations are a recitation of concepts and the other person saying no. If you ever want to see really bad cross examination, just watch a Senate hearing because they do things like say, isn't it true you did this because you hate women? No. Isn't it true that you don't care about people? No. Like, it's not any. It's not useful. It's just asking. It's like giving a speech and allowing the other person to say, no, that's not true. So to me, the best cross examination, and we saw some of it on display there in the, in the Dep and Herd trial, was getting a person to commit to a principle, thinking that it's helping their case, and then weaponizing and snapping that on them. So talking about how, like. So you feel it's unfair to, you know, to, to not allow a person to leave a room when they want to leave the room. Yes. And in fact, you said that he did that on several occasions. And you consider that to be an abusive behavior, isn't that right? Yes. And this person's going, oh, my God, this lawyer is doing a terrible job. Like, they're, they're. And they're like, now that's something you've done to him, isn't it? Okay, this is a terrible. Now what do you say? Yes. Because you just said it was abusive. No. All right. They're saying they're asking you because they know they got the video or they got the audio or they're gonna have witnesses who said they saw you do it. So I kind of love watching a lawyer set it up and set it up and then snap the trap. You know, it's my favorite part of lawyering, you know, is cross examination. I mean, there's a joke among trial lawyers that cases are won on direct examination and they're lost on cross examination because cross examination is just the most fun thing to watch and to do. And so, you know, anytime I get to watch high level competitors, high level. You know, for me, watching a trial like that is like, you know, someone who likes basketball. Watching, you know, watching Michael Jordan play, you know, I love watching. There's lawyers in New York who, you know, John Titler is a great example of one. Larry Greenberg is another one. These are all great lawyers who I go against, who I have cases against, and they're just the best of the best. It's like playing basketball against Michael Jordan. It's like, you know, and for me, you know, I want to be the first among Equals, like, I wanna, I wanna go against the best. You know, it's not fun for Michael Jordan to play against the peewee league. You know, it's fun for him to play against someone. Like, everybody needs their, you know, their competitor, their equal, who they can go against. And so I love watching good lawyers, you know, it's the best. Better than tv.
What, say story you've never shared or a secret you've never told?
I killed a guy. No, I'm kidding. I didn't. No one's recording this, right?
That's the cliff.
That's the cliff story I've never told. You know, the problem with being a lawyer is that you're not allowed to tell a lot of your stories because you're not allowed to, to, to. To waive attorney client privilege. And attorney client privilege survives after the death of the client. So, like, I'm not even allowed, like, to. I have dead celebrities I represented that. I, I can't talk about the facts of their case even though they're dead, you know, so that's, that's a little challenging, you know, Stories I've never told. I mean, there's. So most of my stories I've never told, and most of them I'll never get to tell because I would be betraying a client confidence. But in terms of, of, of, you know, parts of me that no one has ever interacted with or things I've never shared in my, you know, my media work and my discussions, I, I, you know, I've tried to be kind of an open book. Like, I've tried to be very blunt. You know, the, the. I'll tell you something fun. Here's something I've never told anybody, but it'll be obvious if you, if you, if you Google me. When I first was brought into the public sphere, like the media sphere, which was around 2019 when my book came out and the New York Times Book Review loved it and it did really well. And I got to do the Steve Harvey Show. That was the first big media thing I did. And I did like, Rachael Ray and I did a bunch of, like, those things. There was a publicist with my publisher, so they lined up all these things for me, and I found myself going, okay, what would a really successful divorce lawyer who's on TV look like and what would he sound like and what would he do? So if you watch those appearances, like, they're, they're so stiff and they're so weirdly like. And, and it's not surprising to me that that they did well, but they never really caught on because I really was, like, trying to do what I thought a lawyer should do or sound like how I thought a lawyer should sound, which is what I do in a courtroom, you know, and then really, I owe a lot of it to Mark from Soft White Underbelly, because I just didn't. I was like, I'm just gonna go in and just, like, be me. Like, I didn't think anybody would really ever see it too much. And Mark is just such a cool guy. Like, we've become friends, and so I, I've gotten to know him since, and he's just a great human being, but he genuinely found me fascinating, and I found him fascinating. And that interview is just me, he and I just going like, just me, me talking, you know, And I met, you know, you figured this out in this interview. Like, you could say to me, sandwiches. And I'll just go for an hour. I'll be like, wow, you know, the thing about sandwiches, you know, so Mark kind of did that. And I didn't try to be anything. I just was me. And I, when it caught on, I went, oh, maybe that's, it's just that easy. Maybe just be you. And so I've really tried in every subsequent appearance, including this one, to just be a really raw version of myself, a really honest version of who I am, and not, not try to put on the character. Because in the courtroom, I really do have to put on a character character. I really have to put on a certain face. And, and it has to match the judge's temperament. It has to match the facts of the case. Like, you don't want to be representing a perpetrator of domestic violence. Be a hard charging, like, that's the worst. Do not be a bull in a china shop. And that. You want to be very low key, and you want to be very, you know, patient, and you want to earn the right to sort of, you know, in the cross examination, sort of spin the logic. You don't want to be abusive, you know, you don't want to be someone who's intense like that. So I, I, I really, I don't think I've ever talked about the fact that I did it wrong before I did it right. So you can go on and, and look up, you know, my first appearances, and, and they're all on the Internet, and they're just stiff. Like, they're stiff and scared. Because I really was trying to be something, you know, I was like, here's what I should sound like. I Think. And then, you know, when I didn't do that and I was just me, the whole world was like, oh, yeah, that guy. You know, because I. So. I think people can just smell. I learned a real lesson about people's ability to smell inauthenticity. And I learned a lot about people's desire for authenticity. Like. Like, I don't really read the comments anymore, but. Because you'd go crazy if you do. But that first interview got like 20,000 comments, and I remember reading a lot of them, and a lot of them were like, man, this guy's real. Like, he's just saying it like it is. And. And it was. I was. I'm saying it like I see it to be. And I'm just being very blunt and honest and, you know, whether we like the truth or not, that I'm saying, I. I think it's the truth. It's what I'm seeing. This isn't a theory. This is what I'm seeing. This is what my clients are telling me about the failure of their relationships. I don't. I'm not justifying, and I'm not saying it's a good thing, but it's reality, you know? So I. I think that that's something I never really shared with anybody.
Thank you for sharing that.
Yeah, yeah, you asked.
I want to add one more question in before we do the quick fire.
Have you.
Have you got maybe 10 minutes left to do the quick.
Yeah, let's do it.
Okay.
Yeah, let's do it. Yeah, I love it. Yeah.
Just before that, though, I want to open this thing you said about authenticity, because I want to add a couple of things in and get your take. So one is maybe what's going on in your life. So you're trying to be yourself, but you've got some going on in your life. I've done 1500 speeches, and sometimes I stand on the stage and I've got going on in my life that I can really feel nerves. You know, maybe you want to be someone or some way, but you've got nerves and anxiety, and that's getting in the way. So I think you said it like most people say, authenticity. Just be yourself. But I don't know that it's that easy. I think it's one of the hardest easy things in the world that everyone talks about. Yeah.
I mean, what I'll. What I'll say is I. I am wired a particular way. I've never been afraid to speak publicly. Like, I'm doing a TED Talk in a couple of months. I was invited and you can put me in front of five people or put me in front of 50,000 people and I won't be any more nervous. Like I'm very comfortable speaking publicly. So I have that. I know that's a superpower. I know that's a gift and I know it's also partly practiced, you know. But what I will say is when you have shit going on in your life, I've never not had some shit going on in my life. And there are times where I've had unbelievably difficult things going on in my life. My mom passed away from cancer. She was on hospice for two years. I got, got divorced. I mean all these things happened while I was a lawyer. But I found for me tremendous comfort in work. Like for me, I've always jokingly said work is my favorite opiate. You know, that anytime I'm, I'm in pain, like I understand the rules at work. Like I understand, like I'm in many ways more comfortable in a courtroom than in my living room. I don't really know the rules in my living room. I don't know what I'm supposed to do, but I know what to do at work. Like I know, I know very well what to do at work. I'm very comfortable in that environment. I have to be careful about that because work is so comfortable for me that I will just do it all the time. Like I will work all the time if left to my own devices. Because I love it, I'm passionate about it, I'm great at it, I get accolades for it and people pay me. So I have every reason to just do it forever. But you're not, you know, you're not building a life if all you do is your work, no matter how much you love your work, you know, and you will fatigue yourself. You know, if, like I love sex, but if I did it for 14 hours a day, seven days a week, I'd get tired, you know, so you, you need to remember that, you know, But I, but I, I guess my point on authenticity is just that we have this imagination. I think it's what separates us from other animals and we envision what we think, think we should behave like or sound like. We even compare other people to that. You know, I, I remember my now 24 year old son when he was in his late teens, he was, he was mad at me for something that the normal things a teenager gets mad at their dad for. I wouldn't let him do some stupid thing. He wanted to do probably that was, was incredibly self destructive, you know, and he, he was real mad at me. And I remember him saying, like, you know, dad, like you, you just like, like, you know, you don't realize how hard it is, you know, being your son, you know, and, and I said, you know what? You're, you're right, I said, but I'd ask you, like, what are you comparing me to? Are you comparing me to like other fathers, you know, or are you comparing me to your imagined ideal father? Because if you want to do that, I'll compare you to my imagined perfect son. And guess what? You're a disappointment compared to that person. Like, and I'm gonna always and, and learn this lesson because I say it with love. If, if you compare your future wife to your idealized imagined wife, she will fail you, I promise. Like, so compare me to real people. Like, don't, don't even on Instagram or whatever. Like, compare yourself to real people. Don't compare yourself to people with filters showing you their greatest hits. Like, compare yourself to people you see on the street if you're going to compare yourself to anyone at all. So I think that the, the imagined self is, is, is very dangerous in some ways.
So we have a disruptors round, quick fire round. What is the most disruptive thing anyone has ever said or done to you?
I mean, immediately I thought about getting punched in the face a few times. But I, you know, I've trained in the fighting arts for so many years. Why my nose looks like this. So I find it very disruptive to have limbs broken and get choked out in jiu jitsu and punched a few times. The most disruptive thing anyone ever said to me. I, you know, I find silence very disruptive. There was a time in my life where, where I felt the need to fill all silence and it was like the worst tell ever in poker, you know. So I think sometimes silence is actually the loudest thing to me. So that's something very disruptive. I think those would be, those would be probably the two most disruptive forces to me would be actual physical force. Like there's something about, you know, I don't. Anybody who's not trained in the fighting arts, most of what undoes you when you get hit is the surprise. Like if you've ever like hit your head on something, it's like the surprise is actually the thing, you know. So like the first time you get punched punched, you know, the first time you're like training boxing or training martial arts and somebody just clocks you it's like the shock of, like, oh, what was that? You know, and it's. It's pretty sure. But then you go like, oh, okay, I'm all right. You know, Like, I'm all right. Like, I could take more punishment than I thought. So that was the, that, you know, the first time I got hit and not in like a, you know, I want to hurt you kind of a way in like, yeah, it's here. We're here to hit each other. Let's do it, you know? And it was very disruptive. It changed my whole brain chemistry. I think it definitely changed the shape of my nose. And my nose has been broken, like, 23 times, but who's counting? And it taught me a lot about what you can endure.
What's the most disruptive thing you've ever done?
Starting my own law firm three months out of law school. That was insane. I was insane. If my son, My son's a lawyer. If my son had done that, I would have been like, are you kidding me? Are you crazy? Like, a lot of really good people in my life who really care about me and believe in me told me with great sincerity, do not do this. Like, do not do this. This is not Field of Dreams. If you build it, they might not come. Like, don't do it. And, And I, I, I'm so grateful that they loved me enough to say something I didn't want to hear, but I'm really, really glad they were wrong. But that was nuts. Only the hubris of youth. You know?
What's the biggest risk you've ever taken?
This is going to sound like a very cliche, maybe, or silly answer. I think, I think every time I've ever got a dog, think every time I ever got a dog, it was the most risky thing I've ever done. Because you're guaranteeing your heart's going to get broken. Like, you're guaranteed. You're guaranteeing you're going to fall in love with this stupid, wonderful little creature, and you're guaranteeing you're going to outlive it. And, and you're, you're just taking this thing and going, okay, I'm going to let you in in this incredibly profound, beautiful, wonderful way, and then I'm going to watch you slip out of my fingers. And, And I. Every time I've ever done it, I just can't believe I did it. You know, I. It's very present in my mind right now because I have two, Two elderly dogs that I got when they were adopted, when they were babies, and now they're both quite old. They're both 13. And I just can't believe I was ever stupid enough to love them as much as I do, you know? And I'm so glad I was. I'm so glad I am. But, man, like.
Oof.
Like, and I. And I say, oh, yeah, I'm never gonna do that again. Like, when. When I lose these guys, I've never. But I know I'm lying. Like, I know I will. I know. So I think. I think that's. I think love is the most disruptive force. Like, I think that it. You're just. It cracks your heart open. It cracks your world open. Like, to love anything is just stupid. It's insane. It's a form of insanity to let anything in because you will lose every single thing you love. Like, you will. Like, every marriage ends. It ends in death or divorce. Like, every relationship ends. You will lose everyone. And yet we do it, you know? And yet, like, what would life be without that love? Like, so to me, like, this love is such a disruption, you know, it disrupts everything and. And it reformats everything in the most amazing way.
Wow. When I. I'd been with my wife a few months, and we were just getting serious, and the first thing I ever bought her was a. A puppy. West Highland Terrier took her. She always wanted a dog. Her whole life. She'd had cats. And. Yeah, we put him down a couple of months ago. So. What? 16 years. He's. He'd been with us the whole time. I remember thinking, I should not feel like this. I'm a grown man.
How could you not? How could you not? I mean it. Because it's not just this amazing, wonderful creature that's nothing but love, but it's also this chapter. Like, there's this chapter of the three of you, you know? And it's like that chapter is ending, and it feels like the whole world is ending, you know? And yet, like, every beginning comes from some other beginning's end, you know? And. And. And that's what draws me to the work I do, is that, like, all. All of the combat piece of it aside and the intellectual puzzle of it aside, like every beginning is some other beginning's end. Like, we're constantly breaking and we're constantly figuring out, like, new ways to be. And. And so, yeah. I mean, dogs are such a perfect. I. I have to believe that. That dogs are the way they are. Like, they're so perfect and so full of love and so wonderful, and they live such a short Time I have to believe that that's for some reason, to teach us something, to teach us some lesson about how brave it is to love.
What's your most brutal life lesson?
I was maybe the dog thing again. My most brutal life lesson, that love is. Love is, you know, I, I'll. It could tie to the dog thing or can tie to marriage or can tie to romantic relationships or friendships. Love is not gifted. It's. Love is not, not permanently gifted. It's loaned. And I, I think that is a hard lesson, you know, it's a hard lesson to learn that, that the friendships you have will change and shift and priorities will change and shift. Your children will grow, and they won't be what they were, you know, that you loved so much. There'll be something different that hopefully you love just as much, but there's something very different. So I, I think that that's a very hard lesson. It's a hard lesson for me because I, I want everything I love to stay the same. I want everything beautiful to stay beautiful. You know, I want. But I, I, I'm learning as each decade of my life passes that, you know, nothing gold can stay, you know, that, that, like, sunrise can only last so long, Sunset can only last so long. Winter can only last so long. Summer can only let. Like I, I've learned that there are seasons, there are chapters, you know, and, and that's a very, very brutal lesson to learn because, of course, we want to hold on to beautiful, joyful, wonderful things, you know, but you can't, you can't hold on to it. The holding on to it is what causes you so much pain.
What's the best advice you ever remember receiving?
The hard thing to do and the right thing to do are the same thing. My father said that to me when I was very young, and it, it proved to be the truest wisdom anyone's ever said to me. That, that, that if you're, if you're faced with a quandary, that the hard thing to do and the right thing to do are almost always the same thing. You know, that it, that it's, you know, God makes you take the stairs and the devil sends a limo. You know, you, you have to do the hard thing, like lean into the hard things. And, and the, the really great things are on the other side of that.
What's the worst advice you ever remember receiving?
Worst advice? I've received a lot of bad advice. I've probably given a lot of bad advice too. I mean, again, I think I've had A lot of well intentioned bad advice. I had people who said, like, don't do it that way, you'll never make a dime. You know, don't go out on your own. You know, you need, you need to have, you know, a team in order to be successful or you need more experience to be successful. I think overall the worst advice anyone's ever given me is not to believe my gut, not to trust my gut. Anytime somebody tells me, don't, you know, don't just ignore your gut like it leads to, it leads to ruin. But yeah, I got a lot of bad advice in life. I really did. I got a lot of really bad nosebleed remedies that don't work. I got a lot of bad advice on how to cure the hiccups. I mean, I'm very blessed. I haven't been given a lot of bad advice, but I've always been the kind of man who kept his own counsel. You know, I don't ask people for advice. I, I read a lot and I listen a lot to other people's point of view and I, I pick the gems, you know, that, that resonate with me. But I keep my own counsel. I, I really don't, I know what works for me. You know, I don't, I don't. That's why I've always been very hesitant to like, tell people, here's how you should do the thing. It's like, here's how I do the thing and here's how it works for me, you know, and the people I'm most impressed by are people who, who parse it that way. Here's what works for me, here's what I did. And I, I like that. I like being around people who share that very openly and who share their successes and their failures. You know, probably the worst advice I ever got was, is being told, nobody needs therapy. You don't need, nobody should go to therapy. There's no reason to go to therapy. I grew up in a environment where there's a lot of tough guy bravado in the fight world. And there was a lot of like, you don't need to go to therapy therapies for, for wusses. And I think that's bad advice. I got into therapy in my late 20s, early 30s, and, and, and I, I, it really helped me see my blind spots and really helped me, I think, develop as a human being. I wouldn't be where I am if it wasn't for, for the therapist I worked with.
What's your biggest failure?
I won't say my divorce because I don't think it was. I think it was a different kind of success. My biggest failure. My biggest failure would be how I let my fear of failure take my eye off of things that were temporary, that I only had one chance to enjoy. And I didn't enjoy it because I was so worried about failure. I was in. I was in a Whole Foods grocery store a couple weeks ago and there was this guy in his 30s, maybe late 20s standing there and he had like a little kid, like four or five year old kid. And the kid's like, daddy, Daddy, Daddy, look at this, Daddy, Daddy, look at this Daddy. And he had that look on his face that like somebody who's just got like a little kid that wants so much of his attention. And he just had that look of like, oh my God, like, I'm just here to get the chicken fingers. Like, please, kid, just, you know. And he was like, daddy, Daddy, Daddy, Daddy. And it occurred to me that I got called Daddy by my sons for the last time at some point. Like I was Daddy for years and then I was dad, and I'm still dad, you know, Like I call my son, hey, dad, what are you doing? But there was like, I stopped being Daddy, you know, and, and if I had known when it was said that that was the last time it was ever going to be said, I would have wept. But I didn't, you know, and. And a lot of my kids, they're. They're adult men now and they have lives and they have, you know, women that they love. One of them's getting married and I'll never get back. I'll never get back the chances that I lost because I was so worried about providing for them and I wanted so bad to be successful that I just, I put myself in the office from 5:00am until 10:00 clock at night, you know, and I. It cost me a marriage. It cost me. I missed so many things. I went to all the things that were important. I never missed a piano recital. I never missed a sports game. I never missed anything important. But like, there's so many little simple things. Like I could have maybe gone home early and played Frisbee with them, you know, and now I can't, you know, now they're adults, you know, we can't go back out back and have a catch, you know. So I try with the young men who work for me, young women who work for me to like, force them. Like, I try to really say to them, like, go home, go home. Put the file in the drawer and go home. Your kids are going to grow up and you're going to have missed it. So I think that was my biggest failure, is I missed a lot of things that I'll never, ever get to do again. And, and I, I don't beat myself up over it because I know I was in part chasing this thing so I could give it to them. But, man, I regret it. I wish I'd known.
This show is called Disruptors. What does the word disruptive mean to you?
I think, you know, disruptors are, to me, iconoclasts. You know, people that recognize that tradition is just peer pressure exerted by dead people. You know, I, I think that a person. We need disruptors. The world needs disruptors. Whether it's Martin Luther or whether it's Elon Musk, you know, or whether it's me, you know, Like, I think that, I think that anytime we don't accept the status quo and we're not afraid to do something completely different and boldly be ourselves or be committed to our vision, I think that's what it means to be a disruptor. I think the world turns in the directions it turns because people are disruptors, and I love that.
And you told us about your book earlier. Could you tell us the name of it so we can go grab it and then also where we should follow you, where you're most active on, say, media.
Yeah, I'm not super active on social media. You can find me on Instagram @NYC divorce lawyer. And that's usually I, I only go on there just to, like, post when I'm doing something and then I kind of vanish. I post in Ghost, as Joe Rogan put it. But I, I, I just don't, I don't like the distraction that I get of, of, of love too much social media use. My book is called how to Stay in Love. Practical Wisdom from an Unlikely Source. You can get it wherever books are sold. You can get it on Amazon, you can get it on audible if you want to listen to me talk for eight and a half hours. And yeah, I'm working on another book that'll probably be out sometime in 2025, and that one is gonna.
Can you give us a sneak on that, what it's called?
Yeah, it's, it's about endings. It's about endings. It's, that's what I can tell you is it's. I was a hospice volunteer for many years when I first got out of college, and I've been a divorce lawyer for 25 years. And a friend of mine said to me a few months ago, what is it with you and endings? And I said, what do you mean? And he said, hospice, divorce. Like you don't see a trend here, buddy. And I was like, oh, wow, what is that about? You're right, you know, so I. I started writing a book about endings and about what we can learn from endings. And, you know, it's some of the dog stuff we just talked about. It's some of the work things, the childhood things. So it's. It's about that and it's not totally fully formed yet. I'm still in the editing phase, so I. I have great editors. Thank God.
I've had a lot of fun. I'm doing this interview. James.
Jim, thanks, Rob.
Thank you very much. Really appreciate you.
It was a blast. Thanks for having me. It's great to see you.
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