In Search Of Excellence - James Sexton: What 25 Years as a Divorce Lawyer Taught Jim Sexton About Life and Love | E191

Episode Date: August 4, 2026

Jim Sexton has spent more than 25 years watching more than 1,000 couples who once loved each other divide their families, fortunes and futures – but the experiences that shaped him most happened long before he entered a courtroom. One of America’s most successful divorce lawyers opens up about growing up with an alcoholic father, nearly losing his mother throughout childhood, confronting fear, dealing with anticipatory grief, being overweight, rebuilding his body, and learning how extraordinary communication can transform relationships, negotiations and careers.James “Jim” Sexton is one of America’s most prominent divorce lawyers, a bestselling author and one of the internet’s most widely watched voices on love, marriage and why relationships fall apart.But before exploring the courtroom lessons that made him famous, Randall Kaplan takes Jim back to the experiences that created the man behind the reputation and incredible success.The conversation also explores Jim’s struggle with weight, isolation and bullying. After reaching college, he made the decision to change his physical condition one difficult step at a time—eventually becoming a marathon runner, weightlifter and longtime Brazilian Jiu-Jitsu practitioner.Jim then recounts his time as a hospice volunteer, including sitting with people who had no family present during their final hours and reading them stories.  He shares why he would read Winnie-the-Pooh aloud to dying patients and how those experiences taught him to keep death in his peripheral vision without allowing it to diminish his appreciation for life.He also reveals the practice he developed of telling the people he loves how he feels before every goodbye. For Jim, it is not enough to tell someone that you love them. He believes they should also know that you fully recognize and feel their love for you.Timestamps:00:00 — Why a lawyer who has watched 1,000 marriages collapse still believes in love01:44 — The chaotic childhood that trained Jim to read people instantly08:15 — What happens when a child is repeatedly told his mother may die14:05 — The moment Jim decided he could no longer remain the “fat kid”20:00 — Why he volunteered to sit beside strangers as they died24:57 — The two things Jim wants everyone he loves to know before he dies29:43 — The letter to his late mother that uncovered a lifelong emotional wound37:30 — Why Jim kept a tarantula beside his bed for more than 20 years40:45 — When fear creates success—and when it begins destroying it50:40 — The unglamorous job experience Jim requires from potential employees57:31 — The communication skill that separates Jim from other elite lawyers1:03:00 — Why authenticity matters more than sounding impressive1:04:40 — What Jim learned from FBI hostage negotiator Chris Voss1:07:00 — The storytelling secret behind Jim’s extraordinary audience retentionAbout Jim SextonJames Sexton is one of the country’s most prominent and successful divorce and matrimonial attorneys. During a legal career spanning more than 25 years, he has handled over 1,000 matrimonial cases and represented high-profile individuals, business leaders and ultra-high-net-worth clients in complex family-law matters.He is also the bestselling author of:• If You’re in My Office, It’s Already Too Late• How to Stay in LoveAbout Randall KaplanRandall Kaplan is a serial entrepreneur, investor, professional coach, and the host of In Search of Excellence. He is the co-founder of Akamai Technologies, a global leader in cloud services and cybersecurity, and was an early investor in Google.Over the last 25+ years, Randall has advised more than 50 companies, invested in nearly 100 companies, and worked with founders, CEOs, executives, and business owners to help them reach higher levels of success. Through his Extreme Preparation™ methodology, Randall teaches high performers how to prepare better, think bigger, build stronger relationships, and execute at the highest level.Want to Work One-on-One with Me?I privately coach a limited number of high achievers through personalized one-on-one coaching focused on elevating careers, scaling businesses, and reaching higher levels of success both professionally and personally.If you're ready to change your life and achieve your goals, apply here:www.randallkaplan.com Listen to my Extreme Preparation TEDx Talk here: https://www.youtube.com/watch?v=MIvlFpoLfgs Listen to this episode on the go!Apple Podcasts: https://podcasts.apple.com/us/podcast...Spotify: https://open.spotify.com/show/23q0XIC... For more information about this episode, visit https://www.randallkaplan.com/ Follow Randall!Instagram: @randallkaplan LinkedIn:  @randallkaplan TikTok:  @randall_kaplan Twitter / X: https://x.com/RandallKaplanWebsite:  www.randallkaplan.com1-on-1 Coaching: www.randallkaplan.comCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn 

Every marriage ends in death or divorce. You're playing a game you can't win. Is a pre-nup unromantic? I don't think it's unromantic at all. I think there's something extremely romantic about a pre-num. How do you define cheating? And at what point has someone crossed that line? Gosh, there's a lot there to unpack.

I've represented the cheater and the cheated on. I can tell you, it's just hurt people, hurting people. It's all it is. It's just human beings, human emotional complexity, people trying to figure it out. That's all. Is it your advice that people should have multiple sexual partners before they get married? Wow, those are some really big questions.

My guest today has spent 25 years in the most intimate courtrooms in America, not criminal courts, not corporate boardrooms, but the room were two people who once chose and loved each other above everyone else on earth, sit on opposite sides of a table, divide their lives,

and often end up hating each other. James Sexton is one of the country's top and most successful divorce lawyers. He's handled over a thousand matrimonial cases, written two best-selling books. If you're in my office, it's already too late and how to stay on love and has become one of the most watched voices on the internet when it comes to love relationships and why they fall apart. Here's what makes him different. He's not just cynical.

After 25 years of watching marriages, he is one of the greatest advocates you'll ever meet for love. He just happens to know exactly where it goes wrong and today's going to share it with us. James, welcome to The Search of Excellence. Thanks. It's great to be here. I really appreciate you having me. I was excited for this. Awesome.

Well, first I just want to say, when I announced on Instagram months ago, that you're going to be on the show, I got more DMs about you than any guest I've ever had on my show. That's a lot. That's a lot because you've got some people on there. I'm talking about people who are married, single. My mom was blowing up text yesterday. You got to ask them about this.

You got to ask about it. And she's 83 years old. Super, super pumped to be here. I always start with family because our family helps shape our personalities, our future and the rest of our lives. I want to talk about your mom and dad separately. You were born in New Bedford, Massachusetts. You grew up without money.

Your dad was in the Naval Academy. He was a Vietnam vet. Four and a five people in his wedding party died. And he never talked about becoming an alcoholic. What did your dad do for a living? And how old were you when you first noticed and understood he had a drinking problem? Gosh, you know, my dad was a salesman. My dad came out of Vietnam.

Everyone he knew was dead. It was not a time where people were giving. any real support. Veterans were really given any support. And so, you know, he did what every veteran did, which is he poured whiskey and cigarette smoke on it and hoped it wouldn't feel it. And, you know, he had a hard time. He had a really hard time. But he also was a charismatic Southern boy. He'd grown up in the back hills of Virginia. He went to the Naval Academy, not out of any real sense of, like, you know, patriotic duty, but out of the fact that he could get a college education for free. And he had that Southern charm. You know, he said, sir and ma'am. And he,

In Boston and that area, which is where he was a salesman for Johnson and Johnson, he just went like door to door to hospitals because back then there weren't really purchasing departments. He would just go in and he would, you know, he sold gauze and cotton balls and all the products that Jay and Jay sold back then. And he would just go in and, you know, go up to the front nurse's desk and be like, hey, darling, how you doing? You know, is there somebody I can talk to about, you know, and he would just charm people. And he was really good at that. So that was his job. And he built that into a successful business. He end up relocating to New York because he got an opportunity to sell what was at that time a

brand new, unknown technology that came out of Israel, the pacemaker, the actual pacemaker. At the time, it had been created in Israel and they needed, because back then there were Jewish hospitals like Mount Sinai, and then there were Catholic hospitals like St. Vincent, St. Francis. And you, like, Jewish salesmen weren't particularly welcome in Catholic hospitals. And so my dad, as like a southern non-Jewish guy, could get into those hospitals and could like walk around them freely. And so this Israeli company approached him and caught him in an elevator, basically, and said, hey, we've heard good things about you as a salesman. Would you be interested in working for us? And he came home that night and apparently said, before I was born.

But he came home and said to my mom, I got a new job. And she said, what are you doing? And he says, I'm selling pacemakers. And she said, what is it? And he said, I'm not sure. But I hope there's money in it. And that's what ended up happening. And he became one of the most successful salesman manufacturers, representatives for a company at the time called Pace Seder, which was later bought by St. Jude worldwide.

But it was one of the largest implantable pacemaker companies in the world that grew into. So that was what he did. My first memories of his drinking, you know, whoever discovered water, it wasn't a fish. Like my father's drinking was just part of my life. It was part of the ecosystem of our household. one of my earliest memories of my father is like him very glassy-eyed drinking out of his coffee mug and the coffee mug had cutty sark in it and he was just always had the coffee mug and I think I was too young to know it didn't have coffee in it I just knew that dad wasn't in my sister is six years

older than me we had sort of a shorthand of like dad's not in the right frame of mind right now like and we would I remember one of my earliest memories as a child was going into my parents' liquor cabinet and dump with my sister and dumping out like three quarters of what was in it and filling it with water because as a child like thinking, oh, they won't notice, you know, my mom didn't drink at all, but she kind of full time was taking care of my alcoholic father. And my father was not a mean drunk. He was not an abusive man. Like, he was a very charming drunk and a very kind of fun, silly drunk. But when you're a kid, having a parent who's like emotional state vacillates why.

wildly between like silly outrageous and it was just this feeling of like oh my god this is out of control and so i think it was very formative of my personality that i a learned how to be very very sensitive to what's going on around me and notice very small shifts in people's demeanor like you do when you're a child growing up in an alcoholic household and also i learned a desire for control i wanted to have a lot of control because like you you grow up in a chaotic alcoholic household where you just don't know what one hour to the next it's going to look like his dad going to be crying in the garage or mom locking him out or is he going to be like boisterous and silly and happy and trying to like start a project and then fall asleep pathway through it it was it was a

really strange environment to grow up and my father now is in his 80s he's been sober for over 10 years he only got sober in his 80s and our late 70s after my mom passed away I'm very proud of him for that but you know part of his recovery, and I've talked about this before with his permission, was like trying to make amends and sort of apologize for the things that he got wrong. And I think he carried a lot of guilt, you know, and I just remember saying to him like, Dad, I wouldn't want anything but the father I have. Like all those things that were very hard to navigate built in me these traits that gave me this extraordinary, wonderful life I'm blessed to have. Like I love what I do for a living. I have two wonderful sons who are adults and are very successful on their own right. And I have deep relationships

that are meaningful to me. So I'm very blessed. I wouldn't want to be anything other than who I am and what I am. So I would say to them, like, I wouldn't trade you for a non-alcoholic version. You know, I wouldn't recommend to anybody like, hey, if you want to have a really successful kid, you should go be an alcoholic. I didn't thankfully take that playbook in raising my own sons. But I got a lot from the experience of my father. My mom, was the opposite of my father. My father was a Reagan conservative. My father was, you know, a military, ex-military man, very disciplined in some aspects of his life. The drinking, no, but everything else. He made his bed, sir and ma'am, very reliable. You show up 15 minutes early

for everything or else you were late. And those habits he instilled in me. I still show up at the airport two hours before the flight, three hours before the flight. And my mom was the opposite. My mom was like a hippie. My mom was a nurse. She met my dad on Fleet Week. He was just in New York City for Fleet Week, and he was drunk in a bar. And she was there with her nursing school friends. There were teenagers, late teens. And he came up to her. He was in his dress uniform like they always are in Fleet Week. And he said, you're the most beautiful woman I've ever met, and I'm going to marry you. That was his first words to her. And she said, you look like you're in the military. And he said, I am. And she said, of what country? And he said, whatever one you're from, that was their start. And they were married

for over 50 years until my mom passed away from cancer about 10 years ago. So they had a long partnership. I hope you're enjoying this video so far. But before we jump back in, I want to know if you've ever thought about what you need to do to reach a nice level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lift and Seagate. And I also co-founded a company that today is worth more than $15 billion. I've been incredibly blessed in my journey. And at this stage of my life, I want to give back. I want to share the lessons I've learned so you can reach incredible success way faster than I did.

In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link where you can, apply to work with me. All you need to do is answer a few simple questions and if you're a good fit, my team will reach out so we can build a game plan together. All right, now let's get back to the video. Let's talk about your mom. Let's go back. You were six years old. She was diagnosed with

Lyomeyer's sarcoma, which is a rare and aggressive form of soft tissue cancer. She was treated at Memorial Sloan Kettering in New York, one of leading cancer centers. Her doctor, Murray Brennan told her she had six months to live that the tumor was the size of a dime, three weeks before they operated and three weeks grown to the size of a grapefruit. She had the six-month prognosis over and over 15 years before she passed away. And you've used this metaphor of a cow standing in the road. What does that mean? And how did this chronic anticipatory grief of always half-expecting her to die within the next six months affect you as a five-year-old kid and then for the rest of your life? Yeah, that's a big question that my therapist would be

very well suited to answer. I spent a lot of time talking about that in therapy. The metaphor of the cow in the road was how Leo myosarcoma works, which is leo myosarcoma is not a medicine. kind of a tumor. It just grows and then it essentially grows so quickly that it starts to move the things around it. And your body is a somewhat fragile ecosystem in the sense that if something grows from the size of a dime to the size of a grapefruit, if it presses against your abdomen or your intestines, it can cause blockages. And of course, these are the things that ultimately could lead to your death or those blockages. It also has the possibility of touching tissue and creating like necrosis in that tissue. So my mom, unfortunately, you know, every time she'd have a

recurrence, you never knew if it was just going to be something that they could just cut it out, that it had been encapsulated by white blood cells that were attacking it, or if it had become invasive and she would need a bowel resection or she would need, you know, a radical hysterectomy, which she had to have in her early 30s. It was always something. And ultimately, like I said, the tumor that killed her was it was a leomyosar socoma, but it was a bunch of them that all came up at once. And they went in to do this very complicated surgery. They were supposed to, it was supposed to be like a 15-hour surgery because there were all of these tumors and they were micro-tumers. And we were tucked in to just wait, the waiting room for about 15 hours. My dad and I, and Murray came out,

I think, 45 minutes into the surgery. And he just said, yeah, we opened her up. It's like a bomb exploded. And there's just no way we're getting them all out. So they just closed her back up. And they said, you know, palliative care is the right approach. And she was on hospice for two years before she passed. So she died very peacefully with all of us around her. What effect did that have? I mean, I think the two most formative aspects of my youth were my father's alcoholism and my mother's illness.

I think they were really the two things that were the most formative. I never really knew what it was like to not know your mother as something you were about to potentially lose. From one of my earliest memories as a child is my mother crying in the bathroom and hearing it through the door and she was talking to her sister, my aunt Doddy,

and talking about the fact that like what's going to happen if she dies that like will know my father be able to like what will happen to kids like what's this going to be? And I remember my sister is six years older explaining to me that mom you know mom was dying.

And I knew what that meant I had a hamsterile named Cudy and he had died. But I also was raised very Catholic. So it was like, oh, you get to go hang out with Jesus and go to heaven. So that's pretty good. It's not bad, you know. So it was just part of the ecosystem of our home, death. And I think it had a lot of effects on me.

I mean, being told repeatedly that your mom's going to die from a very young age and then she doesn't, you start to sort of, you know, not believe when people tell you something's going to happen. when you piggyback that on the chaos of an alcoholic household, too, it really, really does a number on you. But it also created in me the sense that we're just always losing things, like that you're from the minute you have something, you're losing it. The finite nature of my connection to my mother was from the beginning. And I think it also impacted the way that she would relate to us

because I think she was always trying to prepare us for her loss, even though it didn't come for many, many years, thankfully. So I think it had a tremendous impact on me, but I would again say that it was overall a positive one in the sense that I, I think I like Epicatus encouraged people to do. I think I learned to keep death in my peripheral vision all the time and therefore not allow myself to get too caught up in anything particularly frivolous because if death is in your line of sight and you acknowledge that death is the only inevitability, you tend to not get so caught up in it when people cut up. you off in traffic or, you know, the other ridiculous things that people get very worked up about. So it was a big piece of my life. And I still, I think I still am someone who, in my therapy and in my life, wrestle with the aftershocks of that anticipatory grief, as you put it very well. Or, and also the combination of that and the lack of control and desire for control that a lot of

adult children of alcoholics experience. So all those things were very formative. You know, as a kid, you're sitting there every six months experience sort of a living loss, which has to be just tough. You know, is my mom going to die soon. And then as a result of that, at some point, you gain 30 pounds, which is you, as a lot of people do today, they manifest their on happiness and food. Some people do it shopping. So how old were you when you got that weight gain? And did you realize at some point, you know what? I'm getting heavy. This isn't healthy. for me and I need to lose it and I really need to change and get my shit together.

Yeah, I took comfort in food from a very early age and I didn't, I think my mother and father were so occupied with the things that they were dealing with, the alcoholism, the illness, that I didn't really get an education on nutrition. So, like, I would ride my bike down to the store and get, like, giant bag of Cool Ranch burritos and a big thing of Dr. Pepper,

and that was like, to me, that was like a perfectly acceptable snack or lunch. And so I got very heavy as a kid. I was a fat kid. And that exacerbated some of my isolation because when you're a fat kid, you know, you're not good at sports. And back then, kids were cruel.

You could be cruel. Bullying was tolerated. It was boys will be boys. I got picked on by being a fat kid. And really that shaped a lot of my life and isolation until college. I think when I got to college, the summer of my freshman year of college, I just remember thinking, like, this is enough. Like, this weight, this extra weight has, like, really weighed me down. It's held me down. It's held me back.

And I remember going jogging with, like, converse on. And I just remember I walk, ran. Like, when I say ran, I mean, like, I walk jogged around the block. And I could only, like, jog for a few seconds. And then I would walk. And then I would jog for a few seconds, then I would walk. But, you know, when you're that young, when you're like 19, 20 years old, your body is so adaptive and you have so much testosterone running through your body and growth hormone that within, I think two months, three months, I could run a couple of miles. And then within six months to a year of that, I was running half marathons. Eventually, I ended up running a bunch of marathons.

I mean, I became a runner, like a dedicated runner. And I was real into running. I ran, you know, a lot. And I dropped the weight flew off of me. I still ate, I didn't understand nutrition, so I ate like a runner, I ate just like pasta and rice and like I just eat whatever. I didn't really understand macronutrients and things like that. This is the 90s, early 90s, so it's really before the proliferation of the internet and the easy accessibility of nutritional information. It was when Susan Powder was trying to like tell people you could eat 36 baked potatoes instead of a pat of butter.

And it was like, yeah, but before we understood how that actually works in the brain and satiety and all that stuff. But yeah, I got real lean and then I figured out like, okay, if I get skinny like this, like suddenly I had female attention, suddenly I had female attention. So guys wanted to hang out with me because I had girls around me. And I turned a lot of things around. And from then on, athleticism and fitness was a huge piece of my life. I was a marathoner for many, many years. And then after I kind of felt like I'd accomplished what I could accomplish as a runner,

I'd gone as fast as I could go. I did the Vermont City Marathon in like three and change. I sort of went, you know, I don't want to go further. I did one 35 mile race and I hated it. So I said, well, I'll take up something else. And that's when I got into Brazilian jiu-jitsu about 20 years ago. And since then, Brazilian jiu-jitsu, weight training. And, you know, I still run for cardio sometimes, but mostly on a treadmill.

I'm 53. So I'm, you know, I'm more prone to doing the elliptical or the Peloton bike. I don't really have a lot of pride about it. I'm not, you know, like, you know, I'd rather. have my back and my knees feel good and be able to do, you know, good, like I use my cardio now as like a warm up for my strength training or for my jiu-jitsu. But it became part of my fitness, you know, I think it was good to be out of shape. I think when you've been out of shape and you get in shape, I feel like you'll never get that far from shore because you remember what it

feels like to be in shape. So even, I remember when my mom died or when she was imminently dying, I gained a lot of weight again. I gained like probably 20, 30 pounds because I, you know, I'm not a drinker. I'm not a drunk person. I just needed comfort. Like I was just so sad every day when my mom was dying. And I would make myself really elaborate meals

and just enjoy them. Like I would just eat whatever I wanted to with no thought for anything. And, you know, eventually none of my suits fit and I felt awful and sluggish and tired all the time. It was hard because, you know, people are merciless. Like my male friends would be like,

oh, you're getting a little tubby, you know? Like, and it didn't recognize that like, this is like what I'm doing so I don't put a gun in my mouth. Like, this is like, you know, I'm so sad right now that like I'm not going to make it through the day without weeping if I don't have like a pizza to look forward to at the end of the day, you know? But again, like when she passed, you know, I gave myself a little bit of time to just sort of figure it out

and feel that grief. And then I was like, all right, it's time to get back and share. And I did, and I've stayed in it since, you know, and fitness is a huge part of my life, as I know it is yours. You know, it's having a healthy body, having the instrument, you know, really aligned the right way is such a big part of my life. And everything comes from that. But I think having been out of shape, having been, you know, a fat kid, like I think it's a tremendous teacher. It taught me a lot. I don't look at people who struggle with obesity or struggle with managing their weight as like a character default, like a defect. I don't look at them as weak. I don't look at them as people without discipline.

Like, I understand that sometimes there's a lot of pain going on in somebody and that the sensory pleasure of food is just such a comfort. And I also don't torture myself, you know? I work out so I can enjoy good food. When I was a junior at University of Michigan, I volunteered at Mont's Children's Hospital. I just saw some things that were just very tough to take. I'd go home to my apartment in my dorm,

and I'd say, oh, my God, I just can't believe. I've seen these kids with cancer and bald heads and stuffed animals. Tell us about your experience as a hospice volunteer and reading the book Winnie the Pooh that we all loved as a kid when our parents read it to us. I hope you're enjoying this video so far, but before we jump back in, I want to know if you've ever thought about what you need to do to reach a nice level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lift and C.E. and I also co-founded a company that today is worth more than $15 billion. I've been incredibly blessed in my journey and at this stage of my life, I want to give back.

I want to share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs or excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link with you. where you can apply to work with me. All you need to do is answer a few simple questions.

And if you're a good fit, my team will reach out so we can build a game plan together. All right, now let's get back to the video. Yeah, yeah. So I became a hospice volunteer right when I got out of college. And I just was so impressed with the role of hospice, the idea that you weren't trying to add days to someone's life. You were trying to add life to the remaining days they had.

And I thought that was a really beautiful mission. And it was also a really beautiful way to keep in my own mind the importance of remembering death, you know. There's a Zen Buddhist morning chant that they do at certain Soto Zen Monastery is that basically is that just remember that you're going to die. Like remember that today is one of the days of your life and that there is a finite number of them, you know, that life and death are of supreme importance. Hospice was amazing because you would just get injected into a life of a stranger at the time

that they were imminently dying. It's a moment in someone's life where everything they own, what they've accomplished professionally, like isn't really that important or definitional. Like they really want to like be able to keep a meal down or have some ice chips or like be free from pain for another few hours. It just strips people down to like a real essential core humanity. I would walk out of every hospice visit. You just are there to be of service. Like you just, you know, can I help with the dishes? Can I sometimes? you just sit and talk with people. They rarely want to talk about death. They usually wanted to talk about their life, what they did for a living, their kids, their grandkids, whatever was going on,

you know, what their hobbies were. I would watch baseball games with somebody. I would play checkers or chess. But most often I'd just be of service. Like, how can I help? You know, you just walk in and say, how can I help? And that's really, hospice is a very pure expression of that, you know, that you don't need any particular skill set. You don't need, you're just going into a critically difficult situation that people are navigating and you're saying to this person and their family, how can I be of service? Like, how can I help you? And it's a, it's a beautiful role to get to play. But when you walk out of a hospice visit, you have a reward in the sense that the volume on everything in your life is turned down. Like I just felt like a Zen monk. I would walk out just, the world just felt

beautiful because like, yeah, I didn't have a lot of money in the bank. And yeah, I had finals coming up but it was stressful or I had law school admissions exams to study for, but I didn't have bowel cancer. Like I didn't have someone I love in a bed about to die. I end up coming what's called a vigil volunteer after a certain period of time. And a vigil volunteer is when someone is imminently dying, like they're going to die within the next 24 to 48 hours, and they don't have family.

So they're in a nursing home or they were, this is kind of at the tail end of the AIDS crisis before the antibiotic cocktails came out. So there were a lot of displaced gay men whose families had disowned them and they were dying of, you know, some of the complications that people would get from HIV, like progressive multifocal lucoencephalopathy or some of the other, you know, viruses that you and I, our immune system would kill it instantly. But if you have no immune system because of AIDS, you would die from. And these are usually unconscious people because what most people don't know,

because we worked very hard as the culture to prevent people from having any exposure to actual death. All we really know is like TV representations of death, which are insane. Like people don't go, I loved you all, and they just die. Like, that's not how death really looks. Like, death looks different. Like, people are unconscious usually for a few days. The machine doesn't want to stop pumping blood and breathing, but it starts to fall apart.

Vigil volunteering was just about being in the room so that someone, when they die, there's someone else in the room. I got in the practice of reading Winnie the Pooh out loud because I just, it was a book my mom used to read to me when I was a little kid. It's a very, I think a very soothing story about very human things, the house of poo corner. And so I would just sit and read Winnie the Pooh out loud and hope that this person was, if they were still present, that they were hearing that and would take some comfort and the softness of that story and sort of the simplicity of the themes of the story.

And yeah, I was in the room with, you know, dozens of people when they died. And again, it was one of those things that's really life-affirming. One of the things that we always think about, or some people think about when someone dies, is, geez, life is so fragile. It could happen. We could leave today, God forbid, got hit, get hit by a car, heart attack, whatever this is. And this reminds me when I first started thinking about this 20 years ago, I have a friend named Jay, whose dad was stabbed and murdered by someone on drugs.

And he said to me, you know what? My dad always told me that he loved me, and I never had to worry about that. Those were his last words that he said, you had the same and had the same conversation with your two sons. Tell us about that. Yeah, well, I think working in hospice and also dealing with my mother's illness created in me the desire to make sure that everyone in my life that I loved do that I loved them. And ideally that the last words I said to them would be I love you.

And that the last words they would say to me is that they loved me. I think that they're two distinct concepts. And so I always made a practice of telling my sons are a good example, but really anyone I love. I always made a point of having the last thing I said to, them be I love you because that way I know that the last words I said were I love you. You know, I've lost probably about four or five close friends in the last 20 years. And every one of them, the last words I said to them was I love you.

Because I just make it a practice, you know, of just saying, all right, man, love you. Like even my male friends, like my jihitsu buddies, like tough dudes, like I'll be like, all right, bro, I love you, man. Like, because I want that last thing to be. And by the way, like, especially among men, even like really super tough dudes, one of my best friends is an FBI swat agent in LA and uh you know he's like a manly man and I'm always like love you man and he's like love you too bro like he's like he's not the kind of guy that says I love you a lot to people but like I've created a space for that to be like a still a masculine thing it's like the

bro hug you know but I I think that's one thing is telling people that you love them but also I think there's tremendous value in telling people that you know they love you so I always say to my sons, like, you know, when I die, like, know not only that I love you, but that I know how much you love me. Like, just know that. Like, know that there was never a doubt. Like, anytime we fought, we've disagreed, like, don't ever think back on a conversation we had and think, like, oh, I didn't get to tell my dad how much I love him or, oh, we had that disagreement. And, like, I wonder, you know, I wish he knew that I didn't mean that hurtful thing I said during our argument. Like, you don't have to worry about it.

that. Like, I know you love me. Like, I never doubt that I knew and felt your love. And I think that's a really important thing to do with people in your life is to not only tell them that you love them, but also to tell them that you know that you can feel their love, that you know that they love you. Because I think that's a wonderful gift to give to people to know that they knew, you know, that you knew that they loved you. Because I think we all want not only to feel love, but we want the people we love to feel our love. And so I see those as two distinct pursuits. But yeah, I've gotten in the habit of it.

It's funny because my sons will jokingly say, like even growing up, like when they were teenagers and I'd be like, well, that's unacceptable. You know, and I want you home in 15 minutes. Love you. Like, and it was always like every conversation. But I mean, humorously, like I can look at my phone right now. My sons are 29 and 26. And my last text to my son is, okay, 7.30 or so, love you, you know?

And then my last text with my other son, Billy, which was from yesterday, he said, all right, love you. Like, last thing is always love you. Like, it's just a habit that I forced them into. I hope they mirror it in their own lives. I haven't. My oldest son just got married in September. So I hope it's something he mirrors in his own life. Yeah, my kids, it's the same thing.

I mean, even I've five kids, we always do that, the 24-year-old twins, my 22-year-old son, even my six-year-old and my nine-year-old. Oh, you got a full-care. You know, they start out saying, James, you know, I know. I know. I don't want to say that anymore. Now kind of they're in the habit and they feel it. I'm unfortunately, or fortunately, it depends which way of the way you want to cut this, but a divorce expert, I know more than I should know about this.

I'm going through my second one. And when, you know, when you go through this, you have a really hard time. I went away for some mental healing at a place called the Hoffman Institute. And one of the things that has to do is write letters to our parents. And, you know, very, very hard to do. You write the letter. You don't have to give it to them, which I did not, and which most people don't. It's about all the things that they did, which is the wrong word,

but all the habits that you inherited from your parents. They call it negative love syndrome. You wrote a letter to your mom after she passed away. You never talked about the specifics. Why did you write the letter? It was you to her. She was dead. And what are the specifics of what you wrote in that letter?

Yeah, yeah. Well, I think it was a very similar thing to what you experienced when you recall that, which is it's just such a emotionally charged. thing your parents, you know? Like there's something so primal about that. Like mom is the name of God on the lips of children. Like there's just such a power there and your father is like the world. You know, there's so much there. And that's a primal mark. It doesn't go away. You know, I was laughing with my therapist the other day because I was navigating some challenge in my life. And she was like, well, it sounds like that might be reminding you of your dad and when you did that. And I said,

God, Kate, like, I'm 53. I'm probably the best known divorce lawyer in the world. I represent billionaires and celebrities, and I've still got six-year-old Jim in the back of my head running the show. And she's like, oh, yeah, oh, yeah, like 100%. You and everyone else. Like, you and everyone else. Like, this is a great equalizer for us.

But, yeah, for my mom, I was working with a therapist at the time, and same therapist. And I had said, many things I wanted to say to my mom that I never got to say. And she said, well, why don't you write her a letter? And I said, well, she's dead. You know, she said, there's value in writing it, you know, writing it and then reading it out loud, even sharing it. So I did. And I wrote about, I wrote about the fact that she was, she, she always made me feel ashamed when I needed anything from her. Like when I would, when I would ask for something or, or complain about something I was going through, it was always

met with some belittling of why why do you need that you know or if i would say oh like the kids at school were mean to me today well at least you get to go to school you know many kids don't get to go to school and it was just a way to sort of belittle my pain and then as i got older and i was less of a child and more of a something resembling a young man my mom got meaner to me and i didn't understand why she was colder to me and meaner to me and in the letter i i wrote that i understood like i wanted her to know that I understood what happened, that I was the first man she ever had power over. Like, her father was a bad alcoholic, and then she married my father, who was a bad alcoholic, and both of them had tremendous power over her. Her father, because he was her father,

and my father, because he was her husband and the breadwinner for the family, you know, I said to her, like, I thought it was something wrong with me for so long that I just couldn't get it right. But I realized now that, like, you weren't mad at me. You were mad at all of these men, and I was the first man that you ever had any power over, you know, and I understand that. Like, I understand how powerless you felt, and I understand how you had power over me, and that maybe that was a way for you to, like, get some of that anger you had and you out was with someone you have power over. So I just want you to know that, like, I loved you anyway, and I love you anyway, and that I'm okay, you know.

And so I wrote a long letter really trying to say all of those things, but also being honest about how that left scars on me. It left me really unsuccessful in romantic relationships about allowing a woman to take care of me. I've always been very bad at that. I like to do everything for myself because I grew up in an environment where expressing need was a sign of weakness

and would be met with humiliation or rejection rather than kindness. So a lot of my own therapy in my adult life has been about, learning to frame, allowing someone to comfort me or love me differently, not as an expression of need, but instead, like, one of the biggest breakthroughs I ever had in therapy was only in the last few years where my therapist was talking to me about, you know, when I show up for, because I love showing up for people. Like, I love doing a favor. I'm always the guy who does a favor. And she said,

like, how do you feel when you show up for someone? I'm like, oh my God, amazing. Like, I feel alive and I feel like so of service. I feel so good. And she was like, when a friend is going through something and they reach out to you and they say, hey, can you help me? You like, oh, I love it. Like, I'm at my best when there's a problem to be solved and I can solve it. Like, I love that feeling. Like, when my friend Nate passed away unexpectedly, like, I got in a plane flew to Atlanta and I was like, how can I help?

You know, and I like took the dogs to the groom or the kennel, you know, so that when family came over and then I helped make sandwiches. And I was like, okay, great, I'm doing stuff. I'm helping, I'm helping, you know? And she was like, well, then why wouldn't you let the people who love you do that? Like, maybe they feel the same way. Like maybe they want to help you. It makes them feel good to help you.

It's not a burden. You're not bothering them. Like that's a voice in your head from your mom. Like that's like this is a woman you were married to who you wouldn't let do anything for you. You know, like and so I learned a lot about that from that expression, from writing that letter. The harder thing that I've talked about before was the therapist

after I wrote that letter and then read it out loud through a lot of tears, said, okay, now I want you to go and I write a letter back from your mom to you. And I was like, what do you mean? And she was like, I want you to say what you need to hear from her. Like what is it you needed her to say to you in response to your letter? And that was much harder. It was much harder to write. It was much harder to read.

I don't think I got through the first sentence of it without bawling. I'm talking about it now and I get choked up. Like just the thought of it because what it taught me was, I knew the answers. Like, I know she loved me. Like, the letter was like, yeah, I did all those things because I was scared. I did them because I was mad at your father

and I was mad at my father. Like, but I loved you. I loved you as best I could. It wasn't great, but that wasn't anything to do with you. You were a little kid. Like, and I loved you, you know. And writing it forced me to realize and confront that, no, you know.

Like, you know. Like, you know. Like, the wisdom you find on me, mountain tops is the wisdom you brought up there. You know, like you don't, you're finding things that you know are inside of you already. And so there was something really beautiful about that experience. And since then, I've really tried when I have a challenge with someone interpersonally to use that exercise to write what it is I need to say to them and then write what it is I need to hear from them. And very often I learn that there's nothing I actually need from them, but I actually

know what it is I need to heal in my own heart, in my own heart. In my own I know it. So one of the things that a lot of people don't do because they're afraid and they don't want to go there is they want to confront their fear, right? I have had a fear of sharks. I saw jaws at a young age and even to this day I go wake surfing a lot in the summer Lake, Cordois. I'm still worried about the fin coming up, even though that's irrational.

And I won't get in the ocean because I have a beach's website called Sandy and we've cataloged every shark attack in the world over the last 80 years. Where it happened, the type of shark, what happened to the person? So I'm just terrified of sharks. Then I see online all the time because Instagram knows that I'm interested in it. So I see every shark attack online. There was even a video last week on the news of a guy getting eaten by a shark. You can see the blood in the water.

You had a fear when you were younger of tarantulas. Spiders in general. Spiders in general. I was terrified of spiders. I can't look at a tarantula. I've hated tarantulas. My kids will sometimes torch me. Look at this.

I will not look at it. I have the same fear. I would never, in a million years, put a tarantula next to my bed, but that's exactly what you did. So how, why did you do it? And is there a tarantula in your life today that you're fighting in a fear that you want to get over? Yeah, those are two great questions.

Yeah, I was just afraid of spiders, and I just sort of said, okay, I've got to confront this. And I really believed in the idea of, like, confrontation therapy. And so, yeah, I got a baby tarantula, and I put him in a little round tank and put him right next to my bed. So the first thing I would see every morning was this big spider.

And nobody explained to me that tarantulas live over 20 years, by the way. So my tarantula, Nietzsche was his name. Nietzsche lived like 22 years. And he got begged. He gave this big spider. But yeah, it got me over my fear of spiders. What's the spider I'm afraid of now?

What's the thing I'm afraid of now that I would need? I don't know if the things afraid of now are things I could be as easily exposed to. I think if I had to say what my spider is right now, I think it's probably silence. I think I have a hard time doing nothing. I don't have a meditative practice of any kind. I don't, despite everyone I know who's very high performing, having some form of a contemplative or meditative practice and so many of my friends who I admire their sort of equanimity and their efficacy and sort of the combination of the two,

how they can go from like a real calmed state to a really active focus state and then revert back to that calmed state, which I really admire. I just have a very hard time doing nothing. And I think there is value. You know, Josh Waitskin writes a lot about this. Josh and I train together at Marcella Garcia Academy. He's a black belt under Marcello. And Josh wrote in The Art of Learning about the idea of like creating space, cultivating space, leaving open pockets in your schedule to just see what you want to fill it with. And yeah, that's the spider for me right now. It's something I have a hard time giving myself permission to create.

I still feel like it's wasteful. You know, that when you described like kiteboarding, you know, like cultivating the space for one's passions when you come from a scary, mindset as I did growing up, you know, the idea of, well, I could do this or I could make $10,000 doing this. You start to go, well, okay, if I've sort of won the money game, like I have the things I need and I have abundance and I'm blessed, you start to then start saying, okay, I have to trade this for how much time I'm going to lose, but I still haven't mastered that. It's still the spider. There's still there's still this, you know, poverty beast chasing me that

I can feel its breath on my neck a lot of the time. And I think it's a lot of the time. And I think, If I actually stopped and turned around, I would see it so far in the distance. You know, it's like, I'm running, like it's coming right behind me. And then if I stopped, I'd be like, oh, it's like a speck in the distance now. But my amygdala hasn't figured that out yet. We talk about things that make us successful. We're going to talk a lot more about that later in the show. But is fear a critical element of our success, no matter what we do in our personal lives

and especially our business lives that so many people have ideas to start businesses, start new careers, they're afraid of failing, they're afraid of what's out there, they're afraid of not making money. Is fear critical to our success? Fear is it a genesis for the conditions that create our success? But I think that then it becomes

like diminishing returns and almost antagonistic to success because I think you have to find ways to control your fear or overcome your fear. I think fear is a vitally important thing because bravery is vitally important and if you're not scared, it isn't brave.

Like something is only brave because you're scared and you do it anyway. If you aren't scared and you do a thing, there's nothing brave about it. You're just doing your thing. But bravery, which I think is a virtue and is a feeling of overcoming resistance and power and creates in us like this positive force and positive momentum and self-esteem, overcoming resistance, being brave and accomplishing a thing that was scary is one of the greatest feelings in the world, I think, as a man, but also as a woman. And I really think fear is vital because of that fear, fear like pain. You know, pain is a way of telling you that you're

doing something that might be wrong for you, or you're doing something wrong, or you're doing something in an inefficient manner. So I think it's a message. And messages can be positive or negative or both. And so I think fear sometimes is a way of saying, hey, pay attention. You know, this is a important. There are important things happening here. And so I think that that's useful. Just similarly, you know, I'm wearing a tie and a vest and a shirt. And this is a symbol. This is a message. The message is I take seriously what I'm doing today. Well, you also take what you're doing seriously and you're wearing a t-shirt. So, you know, when you're a young man and you're starting out in the world of business, it's good to be a little overdressed. You know, you have to earn the right to wear a

t-shirt and be taken seriously. So because the boss can wear whatever he wants to, because he's the boss. If you sign the front of the check or you sign the back of the check, it's two different rule sets apply to some degree, but you have to earn the right to wear that t-shirt and be taken serious. So you have to earn the right to not have to wear. Like the first 15 years of my career, no one knew I had tattoos because I intentionally kept my sleeves, you know, put down. And then when I rolled them up, it was with the understanding that I had earned the ability to do that. I think that's how I feel about fear. I think that fear early in your life is a very powerful motivator, the fear of failure, the fear of poverty, the fear of, of, you know, not being able to overcome the obstacles

that you've created or have been placed in your path. But I think it gets to a point where now you have to put that down and not let it govern you. I think you have to start to, and that's my challenge now in this chapter of life, is realizing that fear is still important and a motivator, but it's If I let it, you know, feelings are like little kids. You can't let them drive the car, but you can't shove them in the trunk either. You know, you have to find that balance. I do a lot of professional coaching. Appearance is one of the most underrated elements of success.

It's an intangible that a lot of people don't really get. I mean, I have clients dressed up in a suit and tie. That tie has to have a perfect knot in the middle. There can't be any space. Shirt has to be pressed cleanly. And when I was 27 years old, I got a job with a company called Sun America. Eli Broad was my boss, a 4,400 person, one of only three people who started two Fortune 500 companies from scratch. And I'm in there.

And back then, I bought my suit at Marshall's, T.J. Max, half off, I could get these suits. I remember being a Bloomingdale's and thinking, God, there's a Canali suit there. And it's on sale, 40% off. I'm like, God, that's so nice. And it was still like $650. bucks and it had a vest and I said you know what there isn't a soulless son America who wears a vest and I said you know what I'm going to buy that vest and I looked so good I thought and then you get to work and you know people are like you're an asshole for wearing that three-piece suit I mean who do you

fuck do you think you are getting all dressed up looking like that it was like kind of like people didn't do that here. It was something in Britain that people did. And guess what, Jim, within like three months, the three-piece suit, the vest caught on. But, you know, that's what happened to me. It's what happened to me. I got called Elliot Ness because I didn't, I couldn't afford suits. So my father had been a salesman, and he had some old suits, and we were roughly the same size at that point. And I said, you know, Dan, can I take some of your old suits? And he said, yeah, you could take them. And they were all three-piece suits because they were from the like 60s and 70s.

And I didn't understand fashion at all. So I, and I couldn't afford suits. And so I went into the courthouse and everyone was like, oh, it's Elliot Ness. And I didn't really get it. I was like,

oh, are they saying I look like Kevin Cosner? Because the movie, the untouchables had just come out. And I just remember within, like, I think within six months or a year, in GQ, all of a sudden, there were people wearing a vest. And it just became part of my, part of my look.

Like, I was very defiant. I sort of was like, I'm just going to, this is a thing that makes me a little weird the pot. It'll be my thing. It'll be my brand. It'll be part of my signature look. And yeah, you have to like be able to flip those kinds of things. It's great.

But I see, for guys like you and I that, you know, start out with like aspiring to be able to buy a Canali suit at Bloomingdale. Like, I remember going to Macy's and they had like a one day sale once a year. And I remember they're like, I could get like a heart chaper and Mark's suit. You know, because all my suits were just the ones my dad gave me or they were really cheap ones. They got it like Today's Man

or whatever. And, uh, I just remember, like, I bought one or two really nice suits that were like three or four hundred dollars. And that was all the money in the world, you know? And I wore those suits with like real pride and real, you know, but it's very funny because now I represent, you know, billionaires and hedge fund managers and very few of them have wore suits. Like, they're all wearing t-shirts. They're all wearing, like, very few of them are slavidly looking. But, you know, they wear, but there's always other trappings that they take things seriously. Like, there's their. hair is freshly cut like yours is.

You know, they, you know, they wear jeans in a black t-shirt, but they have a nice watch, you know, like you can sort of look at them and you go, you're, you know, you still take things seriously. It's obvious you still take things seriously, you know. You know, when we're young, we look at people and we say, okay, I want to model myself after that person. I want to look at that person. You can do it by reading magazines.

And one of the things we do is we watch TV shows at a young age. And I think, you know, there are some people who you think when I was 15 years old, Chips was the number one show on TV. And it was about CHP guys on motorcycles. I'm like, man, I want to be so cool. I want to ride a motorcycle and I want to be a police officer. That didn't happen. Around 16, I realized my passion for business.

I want to have a business. I started reading profiles about CEOs of companies like GM, Ford, and T. Boone Pickens and Greenmail and corporate random. Like, that's what I want to do. When you were 15, you watched LA Law. Tell us about Victor Swentes. and one of my favorite actors of all time, Jimmy Smiths. Jimmy Smith, man.

I wanted to be Victor Sifuente so bad. That show, LA Law, which, by the way, you can now watch. It's all streaming online. It is, I loved that show. I mean, I loved Chips also. But I loved L.A. Law. It was that theme song in my head. I still hear it.

You know, I really, Victor Sifuentes, the character played by Jimmy Smith, was this young criminal defense lawyer. and he had an earring. And it was like unheard of that like a lawyer in a suit and he has an earring. And he was just so cool. And I just remember being like,

that's what I want to be. I want to be a lawyer. I don't want to be like a criminal defense lawyer. I don't want to have like an earring and be cool. I want to be Victor Sufentes. And he was a trial lawyer. Like he wasn't afraid to be in a courtroom and a cross-examine a witness.

And he was just intense. I ended up being Arnie Becker, which was the character who was played about, I forget the actor's name. but he was the divorce lawyer. And he was sort of like, I'm going to say a villain on this show. He wasn't a villain, but he was like, you know, Jimmy Smith's character, Victor Fuentes was, like, morally correct

and was always, like, fighting for underdogs and justice. And Arnie Becker was the divorce lawyer who was in it for the money, and he was always sleeping with his female clients, and he had, like, a fancy house, and he was wealthy. And he was much more, like, morally flexible. And I just remember never wanting to be that. but I actually ended up becoming kind of an amalgam of the two. You know, I ended up having the courtroom panache of the Victor Situh

character, but put to use in the context of the divorce lawyer. Let's talk about our studies. We'll talk about college first. You went to Ramapo College, which is the college in New Jersey that most people have never heard of. And while you were there, you were the student body president for two years, which says a lot about your personality, your leadership skills. I want to talk about being a waiter at state.

and now I was a waiter at Chi-Chi's, and I can tell you I learned so much about customer service and what it was like for people to shit on you and people screaming about things like 699 Prime Rib or the tacos were cold. And today you have a strict policy of only hiring people who worked in the service industry. One of the things also that comes up in my coaching,

especially with young people, is nobody wants to do the shit work. Nobody wants to put in the time, the energy of doing things that are unsexy. the everyone today coming out of school wants sexy jobs, internet, AI. No one, you know, today people don't clean the bathrooms like I did or be a paper boy or a stock boy, a Kroger in high school. How important is doing the shit work and the work nobody wants to do towards success later in life? I think it's everything for me.

I mean, it was huge and is huge. I think A, it teaches the humility and a work ethic. B, it, you learn a lot about people when you are. very low on the totem pole and can't really do much for them. Because the measure of someone's morality in my view has always been how they treat someone who can't do anything for them. You know, everyone, of course, now, like I'm around success and I'm successful and I'm, you know, I'm surrounded by celebrity and I'm a quasi-celebrity in my own right. So there's a lot of reasons why it's nice to be nice to Jim Sexton. But, you know, most of my life, there was really no

reason to be particularly, there was no profit in being nice to me. So the question, of like how do you treat someone who can't do anything for you, tells you a lot about your morality. As a waiter, the most humbling lesson was if this person has decided to come to a restaurant to abuse the wait staff, and they are there just to be abusive to you and nasty to you and short with you,

you can meet that force with force, and then you won't get a tip. And the only thing worse than being verbally berated and belittled by a person is doing it for free. So you learned, like, you've got to hold your tongue, you've got to absorb their negativity, and you have to figure out a way to get into and out of this situation that preserves your basic dignity, of course, but also accomplishes the goal, which is I'm there to make a few dollars. Like, that's the goal, and that's what I'm here to do.

And so it was very, very useful training for me. I think that I also liked being able to say to my employees that every single job, one in my office is doing, I have done. I was a good soldier so I can be a good officer. And I think you have to have been a good soldier to be a good officer. Look, I take nothing away from my colleagues, but there are a number of my colleagues who are very successful divorce lawyers whose parents, usually fathers, were very successful divorce lawyers. And so you were kind of handed the keys to the kingdom. Now, look, there's plenty of people that are handed the keys to the kingdom and proceed to squander the inheritance completely and do nothing with it and never really.

And I have, like John Titler, for example, is I think possibly the best divorce lawyer in the world, certainly in New York. He's the one I look up to, and he's my adversary in many cases, but he knows how highly I think of him. John's father is an incredibly successful lawyer. So John, you know, could have just skated on the laurels of his father. Instead, he took every opportunity and every door that was opened by virtue of, A, his own abilities but be the connections of his father. And he took it further and further and further. And he has built it into, you know, something even more impressive than the already impressive thing

his father did. Laura Wasser, same thing. Her father was an incredibly successful divorce attorney. And she is now, she took that ball and took it even further. Yeah. And just, you know, for the people don't know, she's here that when you're divorced, you do not want to be on the other side of Laura Wasser. That is for sure. She is a, she is a weapon. And she is a weapon. And she's, She is very good at her job. And I joke that she's sort of the West Coast equivalent of me. So she represents all celebrities, and I represent all the producers who buy and sell those celebrities.

So I think that, you know, for me, my success was born out of a hunger. And I'm very proud of the fact that I went to a very, at the time, subpar college. It was just a state school that I could get into and afford. I was very proud of being a waiter at Benegans, Pizza Hut, and then steak and ale. I mean, you really picked the more impressive place that I worked, but before that it was Pizza Hut and Benegans. But I...

The Olive Garden, I did too. I did the Olive Garden. I should have mentioned it. Kind of embarrassed about it, but I was a waiter at the Olive Garden too. Unlimited breadsticks. You can't go. Unlimited. They'd fall on the floor sometimes, Jim,

and we're back in the kitchen. They have those rubber mats, you know, with the whole... Oh, yeah. Man, I saw some bad shit there. Like stuff falling on the floor, you put it on the plate, you know, you're making it better. Oh, man. But I will tell you, I really believe that you learn more about politics working in a restaurant because the tension between the host staff and the busboys and the cook, wine cooks,

and the dishwashers and the servers and the sort of like game of thrones that has to be played of like this ecosystem where every single one of those elements can't do their job without the other. And yet, if you align too much with any of them, the others start to reject you. And there was just, it really was the greatest training ground. It's why the people who I hire, I insist that they have some service background,

ideally food service, because I really believe you learn that same ecosystem is the same as a courthouse. Like a courthouse, you've got the judges, you've got their court attorneys who are like their consigliary or their right hand, like the hand of the king. Then you've got the scheduling clerks. Then you've got the court reporters, the court officers.

And again, you might look at a court officer and be like, oh, they're just the person that protects the judge and walks them in and out of chambers. Right. But they're the first person the judge talks to every day and the last person they talk to when they walk out of the courthouse. Like, don't you think they say like, oh, Sexton did a good job today? Or, oh, yeah, I think that case was garbage or whatever. Like, they have an influence.

So you, not everybody can help you, but everybody can hurt. So you really want to make a point of like getting, figuring out what each of these components of the ecosystem has to do with the larger purpose and figuring out a way to like, you know, to have them help serve your ends and also how can you be of service to theirs? One of the things that I see is an investor, venture capitalist and my coaching practice is people come in, Jim, they'll pitch me and I'll say, what does that mean? I have no idea what you're saying. they'll give you a PowerPoint. It's 20 pages. I know a lot about technology. I know a lot about startups. I've been on 50 boards. I've helped companies raise over half a billion dollars. I started a company that says worth $22 billion. I know what I'm doing. And I am a former lawyer, so I get a lot of concepts. And one of the things people miss so many times is they can't explain what they're doing.

And I get pitched all the time, so I have a short attention span. And sometimes just have to cut people off and they say, What's the one-liner here? You went to New York University, got a master's degree, centered on persuasive speech and the mechanics of persuasion. How important is being able to communicate what you're doing in a clear, concise fashion to your success and the people's success in general? I think it's the most important thing. I think the thing that says me part from my peer is my ability to communicate

in a way that people can understand and digest. And mostly, I do that with metaphors. I'm constantly using metaphors. I'm constantly comparing a thing that they don't understand to the thing they want to understand. And I want to compare it to something they get, that they understand completely. So I'm constantly, just like I said, feelings are like little kids.

You can't stuff in the trunk, but you can't let them drive. I'm constantly trying to find the metaphor that will connect it to this person's cognition. And ideally, a metaphor that resonates for them. So if I have a client who's a sailor, I will talk about, I listen, we can't control the way. win, but we can adjust the sales. And that's what we need to do in the courtroom is we can't control what arguments the other side is going to make, but we can adjust and be proactive.

We can look for what are the conditions. So I'll just find, like, personally, professionally, what resonates with this person. So a physician, I'll use medical metaphors without explaining things to them. Someone who does jiu-jitsu, I use jihitsu metaphors. Like, I find the communication style that connects with that person. That's what good persuasive speech is all about. It's about clarity, and it's about connectivity. Brevity is good, but clarity is more important than brevity. And sometimes you can't explain a complex topic

in an extremely brief fashion. It's why I think presidential debates have gone completely off the rails. Because it used to be the Lincoln Douglas debates, which was over three full days. You'd have a two-hour thing and then a one hour of a bottle. Okay, that's a little much for most people's attention span. But how would you solve?

you know, the education crisis in the United States, you have 30 seconds. Okay, that's a, the only answer you could give in 30 seconds is that is a multivariate problem that has existed for an extended period of time and has layers of complexity having to do with socioeconomic status, race, geopolitical divides taxation. I couldn't possibly answer that in 30 seconds. That's the only honest answer to give in 30 seconds. So I think brevity is important, but I think the clarity and the ability to connect to the person's way of hearing. There are some clients of mine. They want to, you know, explain to me.

I find guys in finance tend to do this a lot. They'll straw man things. Like, they'll say to me, explain to me why we're not going to do this. So instead of saying, what are we going to do? They'll say, explain to me why we're not going to do this, because this is what my mind thinks we should do. Explain to me why that's wrong. And then I would explain to them, okay, what's the flaws in the theory?

What's the holes in the thing? Why aren't we doing that thing? So I think you just have to find how this person communicates and what resonates with them. It's the same thing I have to do with the judge. You know, I have to figure out what resonates with their communication stuff. When I got to Sun America, I got this job. And one of the things is 27 years old. And by the way, people hate you.

I'm 27 years old. We have a legal department of eight people. And how is this loser lawyer? I had three jobs in eight months coming out of Northwestern Law School after graduating the top of my class. Got fired twice in six months. And here I'm working for one of the most successful. business people on the planet. And I'm looking around.

And one of the things that we do to learn is model our behavior in certain character trades with certain people who have what we want. And there was a guy named Gary Cratt, who's a very senior person of the company, who ran our broker-dealer network. So it's a network of about 10,000 people who sell financial products. And he could explain things, Jim, so clearly. And I would look at him and say, gosh, you know, I want to speak like him. I want to be able to present ideas from him.

And in three years, there, I really did improve my ability to explain things in the clear, concise manner has been one of the most important criteria of my own success. And I have another friend named Joe Hart, one of my best friends, today's CEO of Dale Carnegie and someone I've been mentoring since we got out of law school together. And what he did is he signed up for comedy at the improv. He got up the Novi Hilton. and he just started being funnier trying to do things. I mean, Joe and I will joke, hey, man, you're not that funny.

I'm like, I'm funnier than you are. No, no, no, no. But I really respected him for what he did. He'd become a better public speaker, not only individually one-on-one and ability to communicate, but in front of a group of people, which is very critical if you're going to be running, whether it's a law firm, a company, a startup, doing public speeches,

what's your advice to people who don't have that skill today? what should they be doing? Yeah, I mean, you don't learn how to swim by reading books about swimming. You learn how to swim in a pool. So I think it's just start conversations. Just the way you get comfortable talking is by talking. Like, just start conversations. People actually are, especially in the digital moment that we're in right now,

people are eager to have conversations. But you have to just find an entry point, and you have to make it clear that you're not selling them something, like that you really are just genuinely looking to connect with them. People love questions. You know, I'll frequently be like, I love that. Ty, where did you get that? Or like, I love that color.

I love that color, you know? Is that, and then they'll just start, you know, people will engage. And I think you just get more and more comfortable by doing it. I think talking is one of those things that, you know, I try to take every opportunity I have to speak before. I've spoken before audiences of, you know, I mean, some of my things have gone to the hundreds of millions, but in terms of their viral viewing,

but I've spoken to groups of tens of thousands of people. I've spoken to groups of 10 people. I really approach all those conversations exactly the same. I really try to approach them from a place of energy, authenticity, really trying to be the most real and authentic version of myself that I can be and not really putting on a persona. If you watch my early media work when my first book came out, I made the critical error of thinking,

okay, what should I sound like on TV? And if you watch my first interviews on Steve Harvey's show, they're very stiff because I'm trying to sound like what I think a lawyer on TV should sound like. And then at some point when I did soft white underbelly, I think was the first time, I really just kind of didn't worry about it. I forgot that, you know, just like I am in this conversation,

I forget that this is a conversation that's going to be viewed by more people. It's just you and I talking. And I'm just talking to you, the manner in which I would talk to you in any context. If we were alone and there was no camera, this would be a conversation we'd be having. And so people can smell that in authenticity, and they can also smell that authenticity.

So I would just say authentically go out and be interested. Like whether it's in romantic relationships, business relationships, being interested and being interesting are two really vital skills. And I think that on a first date, be interested and be interesting. And very often, one of the best ways to be interesting is to be interested. I really think like asking questions about, you know, Chris Boss, who's a friend and a colleague. Jim was on my show. I remember that.

Great. Love him. Brilliant. Brilliant. And Chris is one of those people that's always asking questions because he's using those questions to learn more about you, what motivates you, what are your levers, what are your goals, what are your desires. And in negotiation, he really, you know, if anybody in the audience who has, anybody in the audience who hasn't read, never split the difference, like, go get it and read it 10 times.

Because you'll just, every time I reread it, I learn more and more about it. Those, you know, never split the difference and getting the yes are like, those are just the two books that it's like you can't read them too many times. Tell people who he is first who don't know who Chris Voss is. Chris Voss was the was an FBI hostage negotiator for many, many years. He ultimately was the lead hostage negotiator for the FBI. but he's just someone who now does strategic consulting, but he's just a master negotiator. He's just someone who understands negotiation.

But Chris, and I won't try to summarize the brilliance that is Chris. I mean, your episode with him is a great one. He's had some great conversations with Chris Williamson on Modern Wisdom. But his writing speaks for itself. His social media stuff, he does a lot of speaking and it's really worth watching.

He's a great follow on Instagram. But Chris really talks a lot about the power of questions. You know, instead of saying, well, here's what I can do. He's, well, how can I do that? how am I supposed to take that number off? How am I supposed to justify that number? Instead, by positing questions, and I'd say when I learned that style of negotiating

or approaching a negotiated interaction, it changed the game of my efficacy as a negotiator as a lawyer because I learned that the power of a question of, you know, well, how am I supposed to sell that to my client? Or I'm sorry, what am I offsetting that against? Why would we agree to that? I just want to understand your point of view. And it's not an insincere question.

Like, it's a genuine question. Like, help me understand the thinking behind your position. Rather than just getting up in this positional game where we both take false positions and then find a fake middle. Like, this is a real way of interacting with the principles behind what this person is trying to accomplish. Because in all of these interactions, whether it's in the business realm, the legal realm, the interpersonal realm, we're either, you know, like on the table,

or in the give, right? Like, it's really about, like, you know, we're giving something or we're taking something or some combination of the two. So it really is a seduction of the sense, like where a negotiation is a seduction. I have to convince you that the thing I want you to do serves your interests as well.

And we have to sort of get each other on board with each other's agenda. And Chris does a great job of showing that. But I think for me, you know, studying persuasive speech, learning how to communicate that way, using those basic communication and attention-keeping skills. You know, a lot of the shows I've been on Diary of a CEO, I've done three or four times, you know, Huberman Lab, you know, some of the bigger shows I've done,

they track metrics very, very carefully. You know, Steve Bartlett and his team are like data wonks. You know, they look at every like and every subscribe and every metric. And one of the metrics that's very important in the social media world and in the world that they navigate is retention, which is like when someone starts watching, how long do they stay? And I remember after I did my first diary of the CEO,

Stephen texting me and saying, your retention numbers are off the charts. And I had no idea what that meant. And he said it means that when people start listening, they stay. Like people don't get halfway through an interview with you and just turn it off. Like they stay.

And every time I've appeared since, he says your retention numbers are still like higher than I've ever seen. And I once asked him, why do you think that is? And he said, because you're a storyteller. You're a good storyteller. You keep the energy where it needs to be. And I think that whatever job task you're doing, that's really, that's a key, key thing to master the ability to do. I think it's important to be different than people. That's one of the things about my own success. When I started my podcast, Jim, I had a producer says, no wants to hear about the family

of your guests. No one wants to hear about the parents. I said, fuck all that. I'm going to do my show the way I want to do my show because I know how I grew up. I want to know what makes people. And my retention rates depend on the guests, right? Tony Robbins, everyone listened to Tony Robbins. He's my goat. He changed my life. And as I'm listening to you and I've seen every clip you've posted, hundreds of clips, I've watched your podcast on YouTube. I'm thinking to myself, are people going to tune away hearing Jim Sex and the background, because we've gotten in your background more than you have with any other podcast ever,

but I want people to know who you are. And I'm wondering, like, are we going to start, like at some point, will I launch part two of this, which is going to be talking about the cheating and reasons why people get, I mean, everyone loves talking about the cheating and the sex and relationships and the pre-ups.

So I'm sitting here thinking, like, I may, actually, because everyone knows you it a certain way, but people don't know you this way. I want people to get to know you first before we get to how successful you become. Yeah. Yeah, I have to tell you, it's one of the things that made this conversation interesting to me and also scary, because people really, most of the interviews I do, and I've done a lot of interviews, I'm a more prolific guest than host. And they really start with, okay, I was just hatched into this suit, you know. And sometimes I'll, I'll go back and

talk about my dad or talk about my mom or talk about growing up or talk about my divorce or talk, you know, and just sort of as a footnote to explaining something. But I've seen how your interviews, like there's sort of a linear path. And I respect that. I think it's something that it is a commitment to a certain way of understanding a person, you know, and understanding the trajectory, the hero's journey of a person and how they came to where they are, the good, the bad. But it's also, you know, it's a, for someone like me who spent a lot of time in therapy, it's more comfortable. But there aren't people that, like, they've never really considered their origin story. Like, in fact, they don't want you to think about it.

Like, they just want you to think, no, I was a fully formed CEO. You know, I just, I came out this brilliant person out of Harvard. And it's like, do you know how much has to go into someone getting into Harvard? Like in the habits of thought that had to go there? So that story, I agree with you is a fascinating story. And it's the one that I want to know more about with someone else. But, you know, again, for a lot of people, the unexamined life is just fine. Like they got out of poverty.

They got out of that. I don't want to talk about it ever again. You know, I was a fat kid. I don't want to talk about that ever again because that's not what I am now. And maybe if I talk to about that, you'll see some piece of that's still in me that I'm ashamed of and I don't want to embrace. Whereas I have found by being very open about those kinds of things that I think people can really connect with you because we all have things inside of us, no matter how successful we are. I mean, I represent a lot of very high achieving people who are just like me.

They're frightened. They're flawed. They have parts of themselves they understand and have learned to master. And parts of themselves, they still don't know quite how to navigate. And I think there's something really beautiful about that. My next book is coming out in 2027, Henry Holt McMillan, my same publisher. And the next one is called You Suck at Love. And when I first posited that as a title, they were like, oh, it's kind of negative and like people are going to be insulted by it.

And I said, well, no, the you is all of us. Like, you suck at love. Everybody sucks at love. Like, it's the most natural thing in the world. And yet, and it's, by the way, also a somewhat teachable skill, how to be better at loving someone and how to be better at receiving love from another person. But we spend a lot of time in school teaching people how to divide fractions. And we don't spend a lot of time teaching them how to have a conversation with an intimate

partner or how to give your intimate partner your attention and time and quality attention. So the position of the next book is really about, hey, this is a great equalizer. We should really all embrace it. And a big piece of it is our origin story. and what we learned from our parents and from our siblings and our peer group about what does it mean to be a man, what does it mean to be a woman, what is success, how do you define it, why are we here, what is our purpose? And I think there's tremendous value in getting into that backstory.