Attorney James Sexton on How to Get Divorced Without Going Broke

17 Aug 2026 · 51 min · 25 chapters

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In short

Advice on divorce strategy to avoid financial ruin, including asset protection, mediation vs litigation, spotting money “willful blindness,” and how alimony/spousal support is calculated (with New York factors and “detrimental reliance”).

Guest background

James Sexton, “America’s divorce attorney,” a trial-focused matrimonial lawyer who also does forensic/accounting-heavy divorce planning; he’s known for settlement strategy when it avoids waste.

Key claims

“Fair” is defined differently by each side; preventing alimony is often unrealistic when applicable—focus is on duration/amount and structuring (e.g., front-loading, asset-in-lieu). Divorce planning can be done legally by making advantageous financial choices before filing. Willful blindness about money is dangerous and can enable hidden assets. Mediation is encouraged when no domestic violence/control exists because mediation statements aren’t admissible, but it clarifies positions before counsel review.

Notable examples

A $20M negotiation derailed by a toaster oven; hiding cash via a backyard jacuzzi lined with tennis-ball cans of $100 bills; social media/DMs and Venmo/Zelle/crypto frequently surface; TikTok gifting burned $300k–$400k in marital assets.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Understanding Divorce Fairness

0:21 to 1:06

James explains differing perceptions of fairness during divorce negotiations.

“They're not like traditional banks that love to gatekeep the best rewards and pile on hidden fees unless you have a massive balance.”

Understanding Divorce Fairness

3:56 to 4:46

James explains differing perceptions of fairness during divorce negotiations.

“Now, today you're going to hear his advice for people thinking about getting divorced.”

Financial Habits Impacting Divorce

4:46 to 8:31

James discusses how financial awareness affects divorce outcomes.

“Are you the kind of investor who likes to pick their stocks and ETFs?”

Hiding Money Before Divorce

8:31 to 12:50

Exploration of tactics used to hide assets in divorce cases.

“And it can be used nefariously to hide money.”

Red Flags in Financial Moves

12:50 to 14:01

James identifies warning signs in a partner's financial behavior.

“So what are some red flags that people should be aware of with money moves that their significant other is making that could signal they're planning for divorce?”

Understanding Complex Financial Moves in Divorce

14:01 to 15:08

Learn about the financial complexities people encounter during divorce.

“dollars a year apiece or even a couple of million.”

Preparing for Divorce: Key Steps

15:09 to 17:25

Discover practical steps to take before initiating a divorce.

“They should try to get copies of all of their important financial paperwork.”

The Emotional and Financial Costs of Divorce

17:26 to 19:21

Understand the various costs associated with divorce and emotional implications.

“sitting at the kitchen table with a yellow pad and a pen can't resolve.”

Setting Divorce Goals: Keeping Family in Mind

19:22 to 20:46

Learn how to approach divorce while considering family relationships.

“It wasn't a failure to produce two wonderful children who are now wonderful adults.”

The Role of Mediation in Divorce

20:47 to 21:48

Explore the benefits of mediation in resolving divorce disputes.

“Yeah, I always if I believe that there's no domestic violence happening, no course of control.”
Show all 25 chapters

Best Practices for Asking for a Divorce

21:49 to 23:15

Get tips on how to communicate the decision to divorce compassionately and clearly.

“Where two lawyers are advocating for some.”

Understanding Alimony and Spousal Support

23:16 to 28:00

Gain insight into how alimony is determined and its purpose in divorce.

“Gosh, Esther Perel would give you a better answer than me.”

Understanding Alimony in Marriage

28:00 to 29:10

Learn about the purpose of alimony and its implications in divorce.

“But now, you know, maybe you need a few extra years because the kids are school age or you don't have, you know, or you've lost some opportunities when it came to the kind of placement you would have.”

Gender Dynamics in Financial Relationships

29:10 to 31:00

Explore how gender roles affect financial expectations in marriages.

“Women, women, I think, you know, again, I don't know the gender dynamic of it perfectly.”

The Reality of Alimony Payments

31:00 to 32:50

Discussion on the challenges and realities women face when paying alimony.

“And it turns out that gay and lesbian individuals aren't that much better than us heterosexuals at marriage.”

The Role of Divorce Lawyers

32:50 to 36:00

Discover the complex role of divorce lawyers in negotiations and asset distribution.

“But a lot of what I do is like, you know, kind of wonky dorky stuff.”

Equitable Distribution vs. Community Property

36:00 to 38:20

Understand the differences between equitable distribution and community property laws.

“Well, it's one of the factors a court considers when they're talking about things like alimony.”

The Art of Storytelling in Divorce Cases

38:20 to 40:00

Learn how lawyers use storytelling to present their cases favorably.

“The version of the truth that's most favorable to the outcome my client would like to achieve.”

The Cost of Hiring the Wrong Lawyer

40:00 to 40:40

Hiring the wrong lawyer can be the most expensive mistake in a divorce.

“No, the most expensive mistake in a divorce.”

Common Mistakes in Divorce Negotiations

40:40 to 42:00

Discuss the pitfalls that can derail divorce negotiations, including personal grievances.

“Like, it's better to have a trial lawyer and not need it than to need a trial lawyer and not have it.”

The Cost of Impulsiveness in Divorce

42:00 to 43:35

Learn about the emotional costs and impulsive decisions made during divorce negotiations.

“We've got all these other deal points done.”

Digital Footprints and Divorce Proceedings

43:36 to 45:08

Explore how digital communications impact divorce cases and evidence collection.

“And this guy had burned like three, $400 ,000 in marital assets that way.”

The 'Asshole Tax' in Divorce

45:09 to 47:00

Understand the concept of the 'asshole tax' and its implications in divorce settlements.

“and understand them really, really well to do our job well.”

The Importance of Character in Court

47:01 to 49:14

Discover how a person's character affects their divorce proceedings and outcomes.

“What's the biggest asshole tax paid and why?”

Final Financial Advice on Wealth Building

49:15 to 50:26

Gain valuable financial tips on avoiding unnecessary spending and prioritizing safety.

“You know, I was thinking about this before I came in.”
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Transcript

Automatic transcript. May contain errors.

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3:06Nicole Lapin:If you're starting a business or running one that deserves better tools, Square helps you sell, manage and grow without slowing down. Right now, you can get up to$200 off Square hardware at square.com slash go slash MNN. That's S-Q-U-A-R-E dot com slash G-O slash MNN. Run your business smarter with Square. Get started today. Like I had a$20 million divorce negotiation fall apart because of the toaster oven. James Sexton, America's divorce attorney, is back. A few weeks ago, you heard the first part of our conversation where he gave advice for engaged couples. That episode is linked in the show notes.

3:44Nicole Lapin:Do not miss it. And if you have a friend who's getting married, send them the episode. It might feel weird to send them an episode with a divorce attorney. But honestly, he has a really unique POV on staying together that I think everyone should hear. Now, today you're going to hear his advice for people thinking about getting divorced. Everyone says the same thing. I want to be fair. The problem is their spouse is in another lawyer's office saying, I want to be fair. And they have totally different definitions of what's fair. What you need to know about alimony. You're not going to be successful in like preventing alimony in a case where alimony is clearly applicable.

4:15The question is, is how long and how much? And if I front load it, can I have a shorter duration?

4:20Nicole Lapin:And how to get divorced without going broke. I'm$1 ,000 an hour. I believe that there's no domestic violence happening, no course of control. And there's a really any chance that it would be successful. I encourage people to go to mediation. I'm Nicole Lapin, the only financial expert you don't need a dictionary to understand. It's time for some money.

4:45OK,

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6:00Nicole Lapin:Which financial habits made during a marriage makes divorce more complicated? Yeah, willful blindness, I think would be the number one thing, which is, you know, I'll use a safer metaphor. I love to cook, love to cook. So if you're in a relationship with me, I enjoy cooking. Like it's my favorite thing to do on weekends. I make meal prep and I I love to like make interesting meals and I really love to cook. It relaxes me. It's very soothing. If you don't like to cook, great, right? Because if I like to cook and you like to cook, then we're both going to be like, well, who gets to cook tonight?

6:33But if you don't like to cook and I love to cook and you like my cooking, we are going to have a great time. You should still know how to make something for yourself, right? Because like if I'm away for a week, what are you going to do? Just order DoorDash every day? Like you should know how to do a little bit. Well, it's the same thing with money. Like some people really enjoy personal finance. Like you clearly enjoy it.

6:54Nicole Lapin:Right. But in a relationship. And that's fine. I believe everybody has to do exactly the same stuff. I think if one person is like, hey, I really enjoy personal finance. I enjoy making our budget. I enjoy watching where we're spending. I enjoy making adjustments to our portfolio. But we should be checking in with each other about, hey, I know you might not find this super interesting. But here's like a little snapshot of where everything is. And here's where we're making money. and here's where we're losing money and here's some things I think we should tweak because at least you're a passenger in this thing.

7:25Like we have to be participating together in this and understand if God forbid something happened to you and I don't even know where the money is or where our investments are, that's incredibly dangerous. Well, that's what happens. Listen, life is challenging, right? Most people, both people are working in the relationship. There's kids. One person is usually more of a primary caregiver to the children. most often a woman. Okay. So the truth is, is women are working and they're managing children within the home. They're doing the lion's share of the labor. Men are working as well. So everybody's got their hands very full.

8:00It's understandable to say, yeah, look, you, I got the kid stuff. You got the money stuff. Like, let's just like, like, let's stay in our lane and ever get everything done at the end of the day. But it's dangerous. It's dangerous for you to not know your kid's routine and their pediatrician and what's going on with their school and where there are issues. It's dangerous to not know where the money is and to have some general sense of things. But I have to deal with people's willful blindness all the time when it comes to custody, when it comes to finances. Those are very dangerous financial habits because what you don't know can hurt you.

8:31Nicole Lapin:And it can be used nefariously to hide money. Oh, I have people who come into my office all the time that their spouse has no idea that they are planning to divorce them. And we're doing what I would call divorce planning, which is we're starting to like deplete marital assets and use them to pay certain expenses. And we're trying to like accumulate debt that we can then make marital debt. Like we're there. If you if you have the information, listen. Wait, explain that more. So how what's the most common way people hide money before family divorce family members? I mean, there's lots of ways like gradually you can take small amounts of cash out that you could then say like, oh, I was using that for various cash expenses we have.

9:09But meanwhile, you're just accumulating a pile of cash someplace. You can transfer certain things to family members if you do it, you know, if you do it in a calculated way. I mean, it's harder and harder. Like 25 years ago when I started doing this was before, you know, it was before the Patriot Act and it was before there was such careful reporting of movement of money. And it was really before everything was so digital as it is now. Now it's very hard to move money around and not trace it. Although a hard wallet in crypto has presented unique challenges in divorce law. But even then, most people who use crypto often do it through a third party thing like Coinbase or one of those things, which essentially turns it similar to fiat currency in terms of its traceability.

9:48Nicole Lapin:And you're helping people do that? Well, I'm helping people divorce plans sometimes. Yeah. Yeah. I'm helping people in advance. Look, if you find yourself in a fair fight, your tactics suck. Like part of the job is to help people, if they come to you early enough, figure out how to gain tactical advantage in a divorce. So you can legally hide money before you get it. legally make financial decisions that will ultimately be advantageous to you in the event of a divorce. If you know a divorce is coming, you could do that now. Like you could start making financial decisions like that. The problem is in a divorce, the squirrel who saved their nuts gets penalized in a way that the squirrel who ate their nuts doesn't like the saver gets banged up in the divorce because you're one person in the eyes of the law.

10:31In the absence of a prenup title doesn't control anymore. You're one person. So if you spend all your money and the other person saves all their money, the good news is you're the money in your 401k, half of it's his. You know, you buy your spouse a Birkin bag, you bought yourself one half of a Birkin bag. You buy your spouse a Rolex, you bought yourself one half of a Rolex. So you're one person in the eyes of the law. So people are making choices about their divorce during their marriage, whether they realize it or not. But if you know you're going to potentially be getting divorced, you can make tactical decisions about that.

11:04Nicole Lapin:And a forensic attorney isn't. Well, you're not doing anything. I'm not talking about doing anything fraudulent. I'm talking about making financial choices that looking back, they were tactically good for you in the divorce and they were tactically bad for your spouse at the divorce. You're playing the rules of the system as they're designed. like it's not it's not anything fraudulent I mean are there things people can do fraudulently of course there's tons of things people can do fraudulently you know and and they do them all the time thankfully good forensic accounting can usually reveal those things it's very hard to move money around and not leave a trace but it also depends on like one of the problems too is that if you're married to someone who conducts themselves in very shady financial ways you can't turn around later and go man I can't believe how hard it is to prove the income in this divorce.

11:52It's like, buddy, you've had, you've been married to someone who has a cash business who declares$70 ,000 in income while you guys are living a million dollar a year lifestyle. And now you're turning around saying, man, this sucks. You've been enjoying the fact that none of your income has been taxable for this entire time. You know? Yeah. Like how do you prove that the vault in your house? I once had a client who they had a jacuzzi in their backyard and they had filled tennis ball cans with rolled up a hundred dollar bills in the lining of the jacuzzi. And so they had literally over the years, like filled this lining of the jacuzzi with these tennis ball cans filled with rolled up hundred dollar bills.

12:29And I actually had to I actually had to have an expert come in and testify to how many hundred dollar bills that would be that you could fit in the tennis cans and then how many tennis cans you could fit around it. But it's hard to prove the movement of cash. Otherwise, if cash stays cash, it's hard to prove where cash went. If there was$100 on that table and now it's gone, how do you prove it was ever there?

12:51Nicole Lapin:So what are some red flags that people should be aware of with money moves that their significant other is making that could signal they're planning for divorce? Yeah. I mean, the problem is this. And again, it's a difference between ultra high net worth and non ultra high net worth. So in this space that a lot of my clients currently occupy, there are a lot of wealth preservation and tax avoidance strategies that people employ using trusts and estates and tax attorneys for very legitimate and legal reasons that make a divorce extremely messy. Because, as you know, very wealthy people don't own a lot.

13:33So that way they don't pay taxes on it. So they have an interest in a trust that owns an LLC that owns the real estate that they rent from that trust in an intentionally defective grant or trust. Like, so that's a thing people do for real legitimate tax planning and wealth preservation reasons. But if you're getting divorced, it's super messy because neither of you own it. So now the question is, is who gets more benefit from it? One or the other. How do we deal with something that's no longer in the marital estate? So that that's a level of complexity that really requires a very deep and personal dive into someone's finances for the general population, for like most normal people making, you know, W-2 wage earners or people who make a couple hundred thousand dollars a year apiece or even a couple of million.

14:18You know, large transfers of funds into trusts, purchasing big annuities instead of having large sums of money, leveraging real estate, like taking out huge encumbrances against a marital residence like a home equity line of credit or taking a big mortgage against one residence to purchase another one. but then titling that residence in the name of other family members or third parties or a trust or an LLC. Like anytime someone makes a financial move that's different than the normal status quo, it's worth going, oh, why are we doing that? Like, help me understand why we're doing that. And then the question is, is there plausible deniability?

14:57Is there some plausible alternate theory as to why this thing was done that's very innocuous when in fact it was very nefarious?

15:04Nicole Lapin:Well, somebody is thinking about getting divorced. What are some practical things they should do in advance? They should identify where assets are. They should try to get copies of all of their important financial paperwork. They should make sure that they have access to some funds, if possible, without the permission of the other party, whether it's a credit card in their sole name or whether it's family or whether it's an account in their name so that they have access to hiring counsel, even if they need to get counsel to then make an application for further counsel fees. I mean, I think they're all just basic financial decisions that anyone should make in any situation that could potentially create an emergency.

15:41Nicole Lapin:What's a divorce budget that somebody should keep in mind, like for a lawyer, forensic accounting? That could be tricky. You know, people, the two most reasonable questions anybody can ask me at a consultation is how long is this going to take and how much is it going to cost? And I always tell them those are the two questions no honest lawyer can answer. Because divorce is like a table with four legs. There's you and your lawyer and your spouse and their lawyer. if one leg is off it doesn't matter how nice and straight the other three legs are the table's going to fall down like and then the next question people say is they go well give me a range you know like what's the range like an easy divorce expense versus a really difficult divorce expense and i would say to people it's kind of like calling your friend who's a doctor and saying i have a headache what is it and they'll say well it could be anything i have to run tests and i have to know more information they say well best case worst case all right best case it's the barometric pressure and you'll be fine in 10 minutes.

16:33Worst case, it's an aneurysm. You'll be dead in 10 minutes. Like, did I help you by saying that gigantic of a range? Like simple divorce, five grand, 10 grand. If everybody's in agreement, we're writing up a stipulation of settlement. Everyone signs off on it and we file it as an uncontested divorce. High end, expensive divorce, 2 million in counsel fees, 3 million. Like it depends on how complex the marital estate is. Two W-2 wage earners, if they have custody issues and visitation issues and they litigate the issues of custody, it could be hundreds of thousands of dollars easily, easily. Like I've had cases involving billionaires that was like$20 ,000 in counsel fees total.

17:08And I've had cases with W-2 wage earners who make, you know, less than a hundred grand a piece each. And it's cost a million dollars in counsel fees. Thank God they had family members that were willing to like leverage all of their savings for their custody case. But, you know, it really is not, you know, there is no issue in a divorce that two people sitting at the kitchen table with a yellow pad and a pen can't resolve. But the problem is that that's not it. Like no one comes 25 years of practicing matrimonial law. No one has ever come into my office for a consult, sat in front of me and said, I would like this to be very protracted and awful.

17:45I would like it to scar me and my children. I would like to put your children through college instead of my own. I would like this to be just the most miserable experience of my life. Everyone says the same thing. I want to be fair. The problem is their spouse is in another lawyer's office saying, I want to be fair. And they have totally different definitions of what's fair. And that's where the challenge is. But I tell every single client in the initial consultation, as does every reputable attorney, Laura, John Teitler, Bob Cohen, all the good ones. We all tell them the same thing behind closed doors.

18:16Listen, negotiating table courtroom. I'm a monster. I'll go after everybody behind closed doors. I'd rather you pay her than pay me. I'd rather you pay him than pay me. I'd rather you put your kids through college than mine. Like there is, there's going to be a wedding, you know, like you got a five-year-old, there's going to be a wedding. You can't even imagine it right now because your kid's five, but there's going to be a wedding. And what you do in this process is going to dictate if that's the wedding where you guys can't pass each other by the shrimp boat or you'll throw shit at each other.

18:47Or if it's the wedding where the wedding I just had, where you all stand around for pictures together and you have a drink and you have a dance and you go, you know what? We didn't get the marriage right, but man, we did a good job with these kids. Like, and you celebrate as a family. Like to me, that should be the goal. That should be the goal. Like from day one, that should be the goal. If the marriage is ending, sometimes happily ever after is happily ever after separately. And that's okay. Like relationships can just be chapters in a long book. You know, it doesn't have to be that, oh, well, this one ended.

19:21So it was a failure. I don't consider my marriage a failure. It wasn't a failure to produce two wonderful children who are now wonderful adults. And it made me a better man. I hope it made her a better woman. Like, I think we got real value out of that thing. Just because something ends doesn't mean it was. But by the way, every marriage ends. Your marriage will end. I hope your marriage ends in death. What a weird thing to say, right? But it does. It's going to end in death or divorce. I hope it ends in death. but, but it will end. Everything ends. It's ending right now. It's ending all the time that that's not only does that not make it beautiful.

19:55That's part of what makes it so beautiful is that it's there. Like you don't need anything. You don't need permission to take it seriously. You don't need permission to right now. Like if, if you got a phone call, God forbid, that something happened to your husband, you would suddenly drop everything else in your life. The volume would be turned down on everything else in your life other than that. You don't need that phone call for that to happen. You can just do that. You can just stop and do that and just say, this is important to me. You don't need any flair to be sent up for that to be a real thing.

20:31And that's the message I'm trying to drive home to people is that we can use divorce and the reality of it as an invitation to take love very seriously.

20:43Nicole Lapin:And do you recommend people go through some of the back and forth with a mediator versus on billable hours times? Like, what are your billable hours now? I'm a thousand dollars an hour. Yeah, I think that. Yeah, I always if I believe that there's no domestic violence happening, no course of control. And there's a really any chance that it would be successful. I encourage people to go to mediation because mediation is, you know, it's it's everything that's said in mediation is not admissible in a court of law. At best, you'll resolve your difficulties in mediation. And then before you sign anything, it'll be reviewed by counsel.

21:19At worst, you're going to at least get a sense of what the other side's perspective is on the issues. And you'll start having some understanding of where you guys might have some points of disagreement. And then you can come to counsel and we can like people have this mistaken belief that it's either we go to the mediator, we sing Kumbaya and we sign everything and it's easy or it's knock down, drag out, war, the roses, kill each other. Like those are the two extremes. And thank God, most of the time, it's not this extreme. Unfortunately, it's rarely this extreme. It's usually a negotiation between two people and their lawyers who occasionally are going to need a judge to come in and break a tie.

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21:54Where reasonable minds disagree. Where two lawyers are advocating for some. Because there's things that are black and white in the law. And then there's some gray areas. So everybody's going to argue the gray area in favor of their client. That's our job. So sometimes the judge, the person in the black robe who gets to make the decision, they'll listen to your arguments and they'll go, yeah, more like that and less like that. And then you go, OK. And then you go out and you settle your case. And that's how most divorces go. Like I've had a case. I had a case right last month with John Teitler.

22:21He is, in my opinion, the greatest divorce lawyer in the United States, definitely in the state of New York. He's also one of my main courtroom adversaries. And we had a huge case with billions of dollars on the line and we settled it in like three phone calls and two emails. and probably like 10 grand worth of council fees, 20 grand worth of council fees, because we both knew like, all right, here's what you're going to do. Here's what I'm going to do. Like, here's what it's going to be. And we've had some brawls. Like, like it's not that either of us doesn't like to fight. We're both courtroom lawyers.

22:49We have good teams. We're, we're, we're, we're, we're like, you know, like, like, uh, you know, Ali and Frazier. But the truth is like, we're also not going to waste anybody's time. We're not going to waste each other's time. We're not going to waste our clients money. So we're going to make good choices by saying, okay, look, let's just get there. This is where the judge is going to go. This is let's just get there now. And that's what you do.

23:07Nicole Lapin:Well, yes, my marriage will end in death, as crazy as that sounds. If somebody's isn't, what's the best way to ask for a divorce? Gosh, Esther Perel would give you a better answer than me. I think I'm a fan of being clear with people. I think being clear and compassionate. So I would say I would be I think people have a tendency when they're giving someone bad news to hedge a bit because they think they're softening it. But I think when you're breaking up with someone, there's no way to say it that they're going to feel good about it. So you have to just sort of reject that possibility from minute one and then just be very clear.

23:54Because if you say, you know, I've been thinking that maybe we should. OK, you're already screwing this up. like maybe implies that, but maybe not. Like, I think it turns into, I've given this some careful thought and I think this relationship needs to end. Like that's clear. It feels harsh, but what you're losing in terms of the softness, you're gaining a lot in terms of clarity. So I think clarity is really important. I would say compassionate clarity should be the mantra, which is you're, you're not like, take your share of the blame. Don't put it on this person, you know, but also don't try to be so compassionate that you're no longer clear about what it is.

24:36I've been thinking maybe we should have some time. No, like if you've decided this relationship is over, I've come to a place where this relationship no longer makes sense for me. And I feel like we need to end it.

24:47Nicole Lapin:Let's talk about alimony. Sure. How does I gave up my career for you or for this family show up in an hour. Yeah. So in every state spousal support, alimony maintenance is three words for the same thing. Every state uses a different term. New York, we call it spousal maintenance or spousal support. California calls it alimony. New Jersey calls it alimony, but it's the same thing. It's a payment made by a moneyed spouse to a non-moneyed spouse when there's a disparity in incomes. There are in New York 14 factors in the domestic relations law that govern spousal support or alimony. One of them is what you just described.

25:22which we call that diminished lifetime earning capacity. So diminished lifetime earning capacity is when a person has made decisions by virtue of the marriage that their long-term earning capacity has now been impaired. So it's not just a short-term thing. It's a longer-term thing. The analogy or metaphor I give to people is if you're running a marathon and in mile 20, you stop for 10 minutes, you could still finish the marathon, but you're not going to catch up to the people you were running with before. So you'll finish, but you're not going to catch up with those people because there's a diminished capacity.

25:55Right. Those people have gone further. So the law believes in this concept called detrimental reliance. And in contracts, that becomes a very important thing, which is I detriment. I relied on a promise you made to my detriment. Right. So if I say to you, you can borrow my car tomorrow, I've made you a promise. If you now cancel the car you had and then I turn around and I say, oh, I'm sorry, you can't use my car now. OK, you've now detrimentally relied on my promise. So now I've created damages to you. So that's essentially what alimony is designed. And one of the factors that alimony is designed to address is detrimental reliance, meaning in reliance on you being the primary wage earner and us staying together.

26:38I made certain choices financially about my career, my profession, what I was going to be doing. And I've diminished my lifetime earning capacity. So if, for example, as many people do, when you have children in your 30s or 40s, there's going to be a chunk of time, even if it's just when the kids are before school age, where you might not be working as much. Right. You're going to be out of the workforce for a period of time. That's going to diminish your lifetime earning capacity because the people that didn't step out of the race for that nine months or year or three years or five years, they're getting a head start.

27:12So the people you went to business school with, they're going to have a little bit of a head start. So that's what you're arguing when you're arguing spousal maintenance. And sometimes there's a lot of other factors like future inheritances that people might be getting, what their ability to earn is. Because the idea of what we call non-durational alimony or what used to be called lifetime alimony, it really fell out of vogue quite some time ago. Now it's the idea is really what's called rehabilitative, which is essentially to get a person back to where they would have been or as close as possible.

27:42So the idea, for example, is if a person was an attorney and then they marry someone who's very wealthy and they say, OK, I'm going to step off of partner track and I'm going to be home with kids that we had or adopt during the marriage. That's you're going to step back a bit and you're going to be behind other people. So you still have a law license. You still can get a job. But now, you know, maybe you need a few extra years because the kids are school age or you don't have, you know, or you've lost some opportunities when it came to the kind of placement you would have. That's what alimony is designed to do is to sort of diminish the negative impacts of detrimental reliance that you made in reliance on the promise of the marriage.

28:21Because what is marriage other than a promise? It's a promise that we're going to walk the path together.

28:26Nicole Lapin:Just walking each other home. That's it. Are these conversations different when the woman is the breadwinner? Um, I mean, in my experience, women tend to marry laterally or up more often than men. So a lot of the very high performing women that I represent are married to men who are equally or higher performing. So like you don't often it's pretty common to have like the Goldman Sachs bro or the Black Rock bro marrying a yoga teacher. It's not as common to have like the Goldman Sachs gal or the, you know, Google exec gal marry a broke musician. Seems so cliche, but it's true. Yeah, it's true. Women, women, I think, you know, again, I don't know the gender dynamic of it perfectly.

29:18You could all speculate, probably. But I think that, you know, women find a man who's a successful person attractive. I don't think that that's a secret. And I think men very often like feeling a little more powerful, you know, in terms of the finance that they bring to a relationship or the success they bring to a relationship. I don't think that these are like I'm saying anything too controversial to say that out loud.

29:40Nicole Lapin:So you don't deal with palimony? Well, Palamone doesn't really exist in most states now. But I mean, what I will say is I've represented a couple of outlier, very successful women who are married to men who are not as successful. So I've had some women who were in finance married to a partner at a law firm and maybe he gets laid off or maybe he has issues. Like I had one case where the guy had an opiate addiction that affected his employability. And then she ended up having to pay alimony to him, even though they had both been quite successful. And then his kind of derailing was a function of, of his substance use issues.

30:14Which again, you know, if you believe in the, you know, like, like disease model of addiction, like you wouldn't get mad at someone and be like, damn it, Mike, you have lupus. Like you would say like, you know, damn it, Mike, you're an alcoholic. Like it's an illness. So I get it. And that's the argument that was made. But I will say, and again, this might not be a popular take. Women don't like paying alimony. Like they like it even less than men do from what I've seen. Like every time I tell a woman, yeah, you're going to pay alimony. She's like, what? Like you could be the most Bella Abzug feminist when you get told you're going to be paying alimony.

30:47You get a lot of like like someone who was previously very woke and like not gender is a construct. And, you know, suddenly they're like, he has a strong back. He can get a job. Are you kidding me? Like, I'm going to pay him alimony. Like, it's a very when I do like I actually just I do a lot of lesbian divorces now because, you know, marriage equality, you know, has been the law of the land. for quite some time. And it turns out that gay and lesbian individuals aren't that much better than us heterosexuals at marriage. They find it equally challenging. I don't really know, you know, we were fighting for marriage equality for so long.

31:20And I always found myself wondering that if you really did hate, you know, gay and lesbian individuals, like you should have been fighting for them to have to get married, you know, because why should, why should we have all the misery to ourselves? But one of the things that, that I've found is I, I actually just had a conversation with a lesbian client, like hearing a woman say, like, if that bitch thinks she's going to get half my business and I'm listening to her say that, I'm like, wow, that is not on my 2026 bingo card. Like I did not imagine hearing a woman say that about another woman.

31:50But, you know, listen, it becomes a very mercenary thing. It's not gendered. Like it's about the haves and the have nots. It's about what we owe each other, you know?

31:58Nicole Lapin:So is it more money, more power in these alimony conversations? I mean, certainly. I mean, the person who has the money has something to lose, though, too. And so what would you tell the other side? I mean, I think what you want to always do is find the formula and the accommodation that's going to make sense. You're not going to be successful in, like, preventing alimony in a case where alimony is clearly applicable. The question is, is how long and how much? And if I front load it, can I have a shorter duration? And, you know, the time value of money applies. Or in lieu of alimony, I'll give you this asset.

32:35And that applies certain negative contingency discounts. I mean, a lot of what I do isn't sexy. Like people think divorce lawyers are, you know, constantly like just dealing with, you know, crazy custody cases and like cross examining people. And there's a big part of my job that is that. But a lot of what I do is like, you know, kind of wonky dorky stuff. Like it's a lot about like, you know, applying negative contingency discounts and figuring out if an asset's in an intentionally defective grant or trust. Like what impact does that have on the marital estate? Like it's kind of dorky stuff, but because I'm a trial lawyer and as a trial lawyer, you have to have like a performer streak and you have to be able to like it's I call it full contact storytelling.

33:10Like you're trying to tell a story while someone's actively trying to stop you from telling that story and tell a competing story. So it's like the hardest kind of storytelling imaginable.

33:19Nicole Lapin:You do very well. Well, it's, you know, I just over talk everybody. What's the best argument if somebody wants to keep the house? There's a lot of ways to keep the house. I mean, stability for children is a big successful argument for that, which is if children are at certain ages, you can use those ages as like guideposts of, well, I should be able to stay in the house for X period of time and try to make the argument that this person doesn't need their equity out of the house right away and that they should let it ride and that you couldn't find comparable accommodations for the children in the same geographic area for a similar price or a lower price.

33:53So there's a lot of factors you can argue. the buyout on the residence. I, as I was coming in, I was like sitting in a coffee shop nearby and killing some time before I came in to talk to you. And cause I'd finished in court this morning and I just had a little bit of extra time and I didn't want to go all the way uptown. And I was on my phone returning emails. And one of them was this person just had like a massively false appraisal of the marital residence. Like this house is worth like 800 grand and they got an appraisal for 1.5 million. And so I wrote back and said, great, she can buy us out at that price.

34:25No problem. And of course, instantly now he's like, well, you know, that might not be the right place. I'm like, no, a second ago when we were buying you out, that was the right price. Like, so there are some internal mechanisms that force people to be a little bit reasonable because -

34:39Nicole Lapin:Be careful with the appraisal. Well, yeah, you want to do it in a thoughtful way because you don't want to walk into dueling experts. Like you get an irrationally high appraisal, I get an irrationally low appraisal, And then we have a false average between the two. It's better to come up with like a neutral trusted. This is one of the things that like good divorce lawyers, we have networks of trustworthy accountants, trustworthy appraisers like jewelry appraisers, art appraisers, bag appraisers, wine collection appraisers, all the car appraisers, all the things that people have. We have like the people that, you know, are neutral because the danger of the court system is, you know, there was a time in the 1980s and 1970s where the cigarette companies were getting sued.

35:18And they found doctors who would testify that cigarettes are good for you. Because if you pay an expert enough money, you can get them to say almost anything. So you don't want to get into dueling experts. What you want to do is you want to come up with neutral, fair people that are qualified and know what they're doing and give you accurate values and good, experienced lawyers. We all know who the good ones are and who the hack jobs are.

35:40Nicole Lapin:One of the sexiest divorces out there is Bunny XO and Jelly Roll. Have you heard of them? Yeah, I have. But they seem to be quite kind to each other in their public discussions. So just for clarity, so Jelly Roll is a musician. Bunny is a podcaster. Bunny has talked about how she worked as an escort to support him. That's a very, very specific case. But for entrepreneurs, athletes, if one person is supporting the other in the beginning of their relationship, if they're in the beginning of their relationship for the beginning of their career, what are they entitled to? Well, it's one of the factors a court considers when they're talking about things like alimony.

36:19It's also one of the factors in what's called equitable distribution, which is the division of assets and the division of property. In some jurisdictions, after a certain period of time, like California, you have things like community property, where after a certain period of time, all property is marital property, and there's no distinction between separate property and marital property, like premarital property and marital property. In New York, we are still a state that has separate property and marital property. So if you keep your separate property separate, the appreciation on it will remain separate property potentially in a divorce.

36:48So in a case like that, you know, courts look at that like courts in divorces are what's called equitable courts. Like there's courts of equity and then there's courts of like strict application of law. So like a judge in criminal court can't give you a life sentence for a parking ticket. That would be an abuse of their discretion. There are sentencing guidelines. They can give you this little or this much. And that's it. The legislature has spoken. Courts of divorce are courts of equity. So it's about fairness. So courts look at factors. And that's why I say, like, my job is full contact storytelling.

37:24I can tell that story in a way that makes one side look very sympathetic. And I can tell it in a way that makes the other side look more sympathetic. Like, that's the thing. Facts all come with points of view. So the job of a good trial divorce lawyer is to tell the story in a way that makes my client look most sympathetic and the other side look least sympathetic. So I could represent either of those people in a way that would be more likely to shine in a positive direction for them. Now, again, good divorce lawyers don't try to fit their client with halos and the other side with horns. That's rarely an effective strategy.

37:59The better thing to do is to show that they're both human and they're both flawed. But, you know, the best salesman doesn't seem like they're trying to sell you anything. The best advertising doesn't seem like an ad. Like the best advocacy doesn't feel like advocacy. I'm just shining a light on the truth. But in reality, it's advocacy.

38:17Nicole Lapin:Your version of the truth. Well, my client's version of the truth. The version of the truth that's most favorable to the outcome my client would like to achieve. Are you ready for a lightning round? Sure. What's your favorite legalese term? Oh, boy. My favorite legalese term? Here to forehead herein. Prior discussions here to forehead herein. There's so much good old English I also like vituperative And obstreperous What do those mean? Vituperative is like unduly hostile And obstreperous is being like obstructionist Like you're standing in the way unnecessarily And creating So your client's vituperative conduct Or your client's obstreperous conduct I feel like we have to bring those into the regular Yeah, they're fun I write a lot of nasty lawyer letters So you do a lot of like Here to four Here to four hat here in All proceedings here to forehead here and without prejudice, all claims and defenses.

39:13Nicole Lapin:The most surprising secret that you uncovered in divorce proceedings.

39:22Gosh, I've seen a lot of stuff. There's a chapter in my book called Everyone's Fucking the Nanny. That's about a bunch of people that were having affairs with nannies. And so that's happened a lot. I don't know what it is about nannies. I have a theory of it. I talk about in the book. But so nanny stuff is always very salacious. That's always shocking. People sleeping with each other's other family members. That's always that always catches me off guard. I just feel like there's so many people in the world you could potentially sleep with. Why would you sleep with your sister-in-law? It just feels it's already like adding insult to injury, you know, and making future Thanksgiving's even more awkward.

39:56Nicole Lapin:You know, it's the most expensive mistake in a divorce. Getting married. No, the most expensive mistake in a divorce. hiring the wrong lawyer, hiring the wrong lawyer. People, people make the following mistake. They hire. It's better to have a gun and not need it than to need a gun and not have it. It's better to be a warrior in a garden than a gardener in a war. So people hire like a friendly, I never try cases. I'm very settlement minded lawyer. Cause they think that's going to protect them from having an ugly divorce. And that's like someone saying, I've got a gun, but it doesn't have any bullets.

40:39Okay, then you don't have a gun. What are you going to throw it at me? Like, it's better to have a trial lawyer and not need it than to need a trial lawyer and not have it. So hiring a friendly, warm hug of a lawyer instead of someone that ideally has the full toolkit. Like some people will describe me as a compassionate advocate and a very calming force. And some people will say, I'm the sociopath you want on your side and an unchained pit bull. I'm both of those things, depending on what the situation dictates.

41:08Nicole Lapin:What does a divorce lawyer know about love that a therapist might not say out loud? How the most dangerous lies are the ones we tell ourselves. I think people try to tell their therapist the truth, but they're usually telling them lies that they've told themselves. I think one of the things you get to see as a lawyer is people have to tell you the truth because you have one job and it's to protect them. what's something you've seen ruin a divorce negotiation in five minutes

41:41personalizing things and vilifying someone whether it's the lawyer or whether it's the other party taking it very personally and losing the plot on what's actually important like i had a 20 million dollar divorce negotiation fall apart because of a toaster oven what yeah yeah we had everything done. We were down to personal property. We were like, let's not do this. We've got all these other deal points done. And they said, no, let's just knock it out. Let's get it finished while we're here. And we got down to a Breville toaster oven and it blew up into, well, I bought you. Well, I bought that for you.

42:13Well, you never use it and turn into a whole thing. And I actually like took out my phone and went on Amazon and I said, I can order four of these and they'll be delivered tomorrow prime. And it's going to cost less than 20 minutes of my time. Like, what are we doing right now, gang? Like this is, let's everybody just take a breath, you know? And thankfully it snapped everybody. I did actually order the toaster ovens too.

42:34Nicole Lapin:One for each of the lawyers. Yeah. One for myself, one for opposing counsel and one for each of the parties. What's the most expensive emotion in divorce? Impulsiveness. What's one thing people should never put in writing? The number of people they slept with before they were married. What's one thing they should always put in writing? Their favorite things about the person they're married to like their top five favorite things like when you when you go to your hotel tonight or wherever it is you're gonna go if you're not with your husband write 10 things that you love about him 10 things that he does that make you feel loved like it it will take five minutes and it would be it will actually make you feel more love and when he sees it it'll make him feel more love and it doesn't cost anything you are so romantic a little bit i imagine that people's digital footprints now in divorce can turn things in both ways right how does how have you seen that play out i mean it's super fun because now it's like just all out there like we get everybody's text messages things get intercepted all the time i joke that we all divorce lawyers owe Steve Jobs a tremendous debt of gratitude because having the integration in Apple devices where iMessage comes up on like your iPad that your kid is playing on and suddenly in real time your text message conversation with your with your paramour like your the kid's like mommy what happened to my iPad and then all of a sudden they're like dad's up in the bathroom texting with his mistress and the messages are going you know on the thing and you're looking at it like it's caused more chaos I mean people's talk about how they're not drinking and then it's like oh well what about these pictures from you on instagram what about this person's story tiktok i had a case recently it was tiktok like we what happened we blew somebody's whole life up with their tiktok this guy was like giving away money to like women mostly in brazil like on tiktok he was giving lions and universes like you can gift certain amounts of money tiktok makes lots of money on this bite dance is brilliant they they charge you like a thousand dollars and then you can give seven hundred dollars to a person like each of these toys or whatever like the unicorns and universes and lions and tigers and bears.

44:47And this guy had burned like three, $400 ,000 in marital assets that way.

44:51Nicole Lapin:How often is this stuff showing up in divorce proceedings? Like DMs, Venmo transactions? Constantly, almost every case now. Yeah, all the time. Because if somebody's crying poor, that they're out spending. Yeah, Venmo, Zelle, PayPal, all of them, cryptocurrency. Like we have to be on the edge of all of these technologies and understand them really, really well to do our job well. So if somebody is going through a divorce, how should they think about what they post on social media? I tell everybody you should treat social media the way that my mother used to tell me you should treat things you write, put in writing.

45:23Don't put anything in writing you wouldn't want put up on Times Square.

45:26Nicole Lapin:Or in Wall Street Journal. Yeah. Just don't. Just don't. Assume people are recording every conversation you're participating in. Assume that every document, every text message, everything you send will be shown to everyone. Like, I think that's good advice in general, by the way. Like, I think that don't behave outside the presence of your partner in a manner you would behave if they were there. You know, like you should behave away from your partner the way you would behave if your partner was there. Like, I think that that's what integrity is about. Integrity is how you behave when no one's looking.

45:59Nicole Lapin:Very true. But don't go back and delete things. No, definitely do that. That's spoilation of evidence. It's still there. We're going to find it and we're going to make you look really bad for having tried to delete it. Yeah. You can even pick up additional charges because spoilation of evidence. Once there's been what's called a preservation notice sent, which is one of the first things we send in every divorce proceeding. Now you're you're destroying evidence. So in most jurisdictions, that's a felony. Is there any damages that can be claimed if the other person is just an asshole? Well, not officially, but I most divorce lawyers refer behind closed doors to what we call the asshole tax, which is if the judge perceives your clients.

46:40It's an asshole. They're going to make them pay the asshole tax. So judges have discretion on certain issues, like a range of potential outcomes. And if they decide they don't like your client, they're going to hammer your client where they can hammer them. They're going to make them pay the asshole tax. And I've had a number of cases where I could I got the other side to have to pay the asshole tax. And I've had some cases where my client has to pay the asshole tax.

47:01Nicole Lapin:What's the biggest asshole tax paid and why? A couple of million bucks. For doing what? um just for being rude and and abrupt on the stand arguing with opposing counsel during cross-examination just coming off like a dick like it's just vibes like it's just like yeah this person is just like kind of a dick you know like sometimes people when they're nervous you know they don't come off like the way they are and so they could be a really nice person and like they did a hundred things right but all you gotta do is one thing wrong like no one ever says like think about all the people jeffrey dahmer didn't eat like they're very caught up in like the ones that he did.

47:36But like most people he met, he didn't eat like in fairness, like the majority, overwhelming majority of people he met, he did not eat. Now, that's not an effective defense as a lawyer. Right. You can't go in and be like your honor. Sure. He ate five people, but like he met thousands of people. That's not even one percent of the people that he met that he ate. Come on. It's not that many. Like that's not a good argument. But if you've told a story 50 times and you've done everything right in a divorce proceeding, but you lose it on the witness stand at the critical moment, judge is just going to be like, yeah, you're an asshole.

48:09And then they're going to be able to hit you.

48:11Nicole Lapin:I'm actually quite glad that the asshole tax exists. Me too. Me too. Yeah, I weaponize it all the time and I try to mitigate against it for my clients as best I can. But sometimes, you know, if you can't teach a dog how to drive, it doesn't mean you're a bad teacher. Like, you just said about an impossible task. Like, there's times where I'm trying to make someone likable and they're just not likable. They're just not a likable person. Literally being a kind person pays. It pays to be a kind person. It pays to be a kind person. It pays to be charismatic. It pays to be humble. It pays to be. Look, we've all watched trials on TV.

48:40We watch Johnny Depp and Amber Heard. You know, we watched what it's like when someone's charming and affable on the witness stand and when someone's kind of an asshole on the witness stand. And it blows up in your face when you're an asshole on the witness stand. And again, it doesn't matter. Like the facts aren't necessarily people don't buy the steak. They buy the sizzle. So appearance is important.

49:00Nicole Lapin:James, as you know, since you've listened to our episodes, thank you so much. We end all of them by asking our guests for a final tip that listeners can take straight to the bank. We didn't talk much. We could talk forever. I love the way you are so poetic and your storytelling. You didn't come from money, but what is a financial tip that you've learned along the way to grow your wealth? You know, I was thinking about this before I came in. And my joking answer based on past relationships would be is if you're ever dating anyone and they decide they want to take up equestrian as a hobby, encourage them to take up cocaine instead because they're cheaper.

49:37That's my joking answer, but a truthful and based on life experience. I actually think the best advice I wish I'd learned earlier in life that I think is really useful is don't buy things you don't need with money you don't have to impress people you don't like. I think that right now we do a lot of that. We buy things we don't need with money we don't actually have, mostly to impress people we don't actually like. And I think that consumption will never fill the void inside of us. I think love fills the void inside of us. And so use your money as the tool that it's supposed to be, which is to make you feel safe and the people you love feel safe.

50:18And don't try to shove money at problems or consumption of products at problems that aren't going to be solved that way.

50:24Nicole Lapin:Buy money. Buy money.

From the publisher

Divorce attorney James Sexton is back for part two of his conversation with Nicole; in part one, he talked about advice for couples getting married. Today, he’s giving advice for people getting divorced. Nicole and James dig into the financial habits that sabotage marriages, the creative ways people hide money before filing, and the red flags that signal a spouse might be planning an exit. Plus, James gives simple advice on what might be the most complicated part of this process: how to tell your spouse you want a divorce.

James also breaks down how alimony actually works, the best argument for keeping the house, and the negotiating tactics he uses to fight for a bigger settlement. Then things get spicy: the digital footprint mistakes blowing up divorces in real time, the unofficial "a-hole tax" judges impose on bad behavior in court, and the wild story of a $20 million divorce that almost collapsed over a toaster oven.

Check out Part 1 of Nicole's conversation with James Sexton

Start investing investing at SoFi.com/MNN 

Check out Nicole's financial literacy course ⁠The Money School⁠ 

Find a Financial Advisor or Financial Coach from Nicole's company ⁠Private Wealth Collective⁠ 

Watch video clips from the pod on ⁠Money Rehab's Instagram⁠ and ⁠Nicole Lapin's Instagram⁠ 

Follow James’ work and check out his latest book

Here's what Nicole covers with James:

00:00 Are You Ready for Some Money Rehab?

02:31 The Financial Habit That Complicates Every Divorce

05:01 How People Hide Money Before a Divorce

09:21 Red Flags Your Partner Might Be Planning a Divorce

11:35 What To Do If You're Thinking About Divorce

12:11 How Much Does a Divorce Actually Cost?

17:13 Mediation vs. Litigation: Which Should You Choose?

19:37 The Best Way To Ask For a Divorce

21:18 How Alimony Really Works

25:00 When the Woman Is the Breadwinner

28:29 Is Alimony About Money or Power?

29:58 The Best Argument for Keeping the House

32:11 Bunnie XO, Jelly Roll, and Who's Entitled to What

34:56 Lightning Round

38:03 The $20 Million Toaster Oven Story

39:14 The Most Expensive Emotion in Divorce

39:20 What To Never (and Always) Put in Writing

40:00 How Social Media Can Blow Up Your Divorce

42:54 The "A-hole Tax" Explained

45:31 James Sexton's Tip You Can Take Straight to the Bank

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