“Is our relationship going to end on air?”

On today's episode.

Is this going to be the end of my relationship on air?

Meet Justin and Maggie.

We're freelancers. We're really good at making money, not necessarily planning on how to spend it. I'm the responsible one right now.

And who's he?

Maybe the irresponsible one.

Justin is 38. Maggie's 34. They've been dating for a couple of years, and Maggie does not want to combine finances with Justin.

I just want some similar priorities and some similar game plan.

Maggie spent her 20s traveling the world.

I was traveling for six years out of a backpack and working from my laptop. My goal was to make good money.

And now she's focused on the future.

I want to save a bunch of money, and that's the mindset I'm in.

Justin also loves to travel, and he wants a future with Maggie.

I definitely put experiences and living life before anything else.

Now that Maggie is making life plans that might not include him, Justin feels hurt.

I just really didn't feel like there was a we or us. I was like, where do I fit in on this?

I think it's safe to say that we're at a point where it's like, if it doesn't change, it's not going to last.

Now let's meet Justin and Maggie. I've got Justin and Maggie's CSP in front of me getting ready for our conversation. Check out what I noticed. All right, let's take a look. Maggie and Justin. Maggie spent her 20s backpacking through different countries. She has big financial dreams. She wants stability. Justin grew up wealthy. He's run his own business, but never really paid attention. Money comes, money goes. They started an LLC together for their YouTube channel on motorcycles. Justin wants to combine finances and their lives. Maggie doesn't want to get caught up in the financial mess. On the flip side, he feels like he supported Maggie financially, and she's not willing to reciprocate that. Trust is an issue. She doesn't trust that he'll get his financial life together. Wow, there's a lot going on here. All right, I'm looking now at their csp. Looks like they have not combined their finances. That's fine. Her net worth is 45,000. His net worth is negative $63,000. She has 1,000 bucks invested. He has $7,000. She has $16,000 saved. He has $1,000, and wow. She has 15k of debt. He has 92k of debt. All right, let's go to the income. They make a pretty healthy income. 120 for her, 100 to 250k for him, that's a lot of income. $267,000 a year. Let's keep going. I gotta say there's something fishy about these numbers. I wonder if there's some mixing of business in here. I've seen this before where sometimes numbers don't add up and it's usually one or both people are in a business and they're counting some of their business expenses and things like that. So maybe that's what's going on here. Let's keep going. 36% going towards guilt free spending, which is $7,444. I doubt that that number is true. I think it just kind of flowed down to the bottom. My guess is that they could probably put more towards debt and pay that off aggressively. My overall assessment, one, they make a lot of money. That part is good. Two, they have separate finances. That's okay. I'd like to understand more. Three, there's a bit of a disparity not just in their spending, but certainly in their debt levels. And four, the way they treat money and they treat each other. There are little clues showing up here on the csp, but it's really probably going to come out when I talk to them. So I'm very interested to speak to them and see what's going on here.

We are going to be moving next year and the question is, what can we afford? We're freelancers. I don't know anything about your situation. Just kind of wanted to get on.

The same page of all. Do you talk about money?

No. Money's been a weird thing for me, but I was like, if I feel like I had somebody that I could tackle life with, like, this is her. But we just couldn't get there. It just, it didn't happen. But finally it was like, hey, I'm going to put us on public display. We're going to talk about all the things that most people never talk about.

Have you tried to talk about money in this relationship?

Kind of, yeah.

How did it go?

I set up a spreadsheet that I've been working off of last year and I was like, what are your fixed costs a month? What are our goals? Hey, put your numbers in here. Look at mine.

Do you realize my question was how did you talk about money? And your answer was, I created a spreadsheet. Exactly. Anybody find that a little odd? Okay, well, that's what we're here today for.

Yeah.

Talking about money, especially first few conversations probably should not involve a spreadsheet okay. What was your reaction when you saw that spreadsheet, by the way?

I was like, great, here we go. I already hate doing money. I feel like I have an overwhelming situation in general. And then, you know, on top of that, it was just like, we never talked about really anything. Debt goals.

When you felt all these things overwhelm and there's complexity in your financial lives. What was your reaction with the spreadsheet? Did you fill it out?

Yeah.

Okay.

For one month, and then it stopped.

Now your finances are separate, correct?

Kind of. We have a partnership with the YouTube channel.

So you have separate finances, but you have a joint venture, and you make money through that, but you also make money independently?

Yes.

Okay, let's.

I can see why it feels confusing, but it's quite common. The good news is there are solutions for this situation. All right, so you both live together. How do you pay the rent or mortgage?

One of us manages the rent and everybody. Because we have three adults in our household, Justin currently is taking care of rent, so we send him rent, but I'm managing the bills. There was a period of time where I was managing the rent and Justin was managing the bills, and we weren't able to get a number.

I wasn't every month being like, okay, it was $250 for all the things we have to split it. I just threw it on the credit card and stocked up a bunch of bills.

Oh, why'd you do that?

Honestly, it was just sort of a set it and forget it. I screwed myself. Honestly.

What's a time in the last six months where the two of you really disagreed about money?

She doesn't like the way I spend my money on sunglasses.

That's it. I don't think you guys flew across the country to talk about $100 sunglasses.

I'm in the dark, I feel like, about his financial situation, but I can do simple math in my head sometimes, and I'm like, this is not adding up that you spent $400 on sunglasses this month. I think there's certain things where I'm just like, I don't spend money like that, and I'm really on top of my expenses.

One thing that's been contentious and difficult, and it's a really complicated situation overall, is that our roommate is Maggie's best friend, and she had a brain tumor a few years ago and had it removed. But it's the type of thing that eventually will come back.

It is coming back.

Is coming back. And so she's going on medication now, but more or less all the disposable income or whatever Maggie's setting aside is going to taking care of her and her kids.

She has two kids that live with us.

It's a tough situation to be in because I kind of feel like that's the priority, and I'm not necessarily in that bubble.

Meaning Maggie's friend and her children are the financial priority for Maggie.

Right.

And you feel your maybe second priority.

Or not a priority at all in that regard.

And what is the financial resources that you're putting behind your friend? Are you her caretaker?

Not right now. There's things where I'll plan trips with them and I'll take care of everything.

And does your friend, does she earn money?

Yes, she does. One of my goals for all of us is that this, financially, we're splitting a house between three adults. This is a chance for all of us to, like, catch up on some finance things. But we weren't necessarily on the same page with that as well, too.

Why not?

I mean, I had it as my goal.

Did you ever talk about that? Hey, it's going to be three of us splitting expenses, so this is a chance for us to pay off debt and get ahead.

Honestly, her and Ashley talked way more about finances and getting ahead than Maggie and I did.

Have you ever talked about that?

Maggie was trying to convince me why we should have another adult and two children living in her house. And as part of that, it should be because we get to save more money.

And your reaction was?

Sure.

How would you characterize the dynamic of money in your household?

I'm the responsible one right now.

Okay. And who's he?

Maybe the irresponsible one by default.

Okay. What do you think about that?

Pretty accurate.

Oh, okay. That makes my job easier.

There was a time, though, in the beginning of our relationship where it was very flipped. Like I was paying all the bills and some, you know, and, you know, I helped out considerably when it came to finances.

Were you making more?

I was making a lot more.

Okay, you're making more. So you were paying the majority of the bills and when you say and more, what's that?

So for the first year that we were together, Maggie was doing this influencer thing, and I wanted to help her out. So I was like, how about I put you on payroll and, you know, you can help me with some stuff. I need to redo my website and, you know, maybe you can help me come up with some strategy for business.

It kept me afloat. And at the time he was making money, he was paying another full time employee and had an office, and I didn't know his situation. And I think right off the bat, I haven't known exactly what his situation was. And that was where it started. And then a lot of that, it felt like, was getting held over my head. And I was like, okay, we need to move away from this dynamic. I don't want that to be a part of our relationship. And I went and started finding work and found jobs and started holding my own. And then I was like, okay, cool. Like, I still didn't know what his situation was. I'm like, you should be in a much better place now that I'm not such a strain on it.

Did you say that?

No, not necessarily.

Did you not talk about this kind.

Of stuff at all?

We kind of talk about it. There was just a lot of, like, struggle with relationship stuff that we were working through. And to have money tied into it, like, I think that's also added to the maybe the aversion to talk about it.

Who's aversion?

Both of us. Finance is always the tricky thing. It can cause a lot of trouble in a relationship. It's sometimes subjective. I mean, whether I'm spending $200 on a pair of glasses, for me, that makes sense, and that doesn't make sense for somebody else.

It's interesting you say that with the sunglass example. I agree. It might make sense for you. Your partner might think it doesn't make sense. But it seems to me that you both don't have a way of deciding if that's a good decision or not. How would you decide right now if buying $200 sunglasses is a good decision or not?

I think that Maggie would feel much more confident in my choice of spending $200 on sunglasses if she knew that I had my finances handled. Do you? Absolutely not.

Okay.

I shouldn't have been buying $200 sunglasses. Okay, that's all right.

So, Maggie, your concern is probably warranted.

Yeah.

But when you express the concern, how's it received?

It just doesn't come off right. I just know that there's been a bit of a blind eye turned to them, it feels like, because it was happening when we split bills last year to the point where I was like, how about I manage that? Because it seems like it's a lot. Anytime rent was paid, we asked, what do we owe for bills? And he's like, I need to take a look at it, was the answer. And then it wouldn't get taken a look at. And I mean, there's a lot going on no, we probably should have hounded him, but it got to the point where we hadn't paid anything in a couple months. And I was just. I did say, like, I know this is stacking up and we can't back pay, so let me manage that. And you just handle the rent part. Because it's a flat rate every month, we divide it three ways. We always know what it is. It's all the same.

And is that where you are now?

Yeah, that's where we're at now.

Any different opinion on what happened?

They asked a couple of times, and then what happened is later on when we started doing spreadsheets and looking at the bills, I was like, I've been paying for the bills the whole time and it's been going on my credit card and it's stacked up a couple thousand dollars worth of bills at this point. And then she was like, oh, well, we asked, you know, and you never gave us an answer. So we're not going to back pay you now. And you're going to have to take care of that. And then moving forward, we'll switch over. I'll take care of the utilities and then you can take the rent.

Is that what happened? You did not get the back pay?

No, I did not get the back pay.

Why is that?

It had just stacked up a lot. Like it was, to a point where it was like it hit a tipping point where it was like, I don't even know where we stand on this because he had been managing it.

Justin, it sounds like you were probably not as forthcoming communicating about what's owed every single month. I agree. Probably owed back pay.

Right.

Even though it might be difficult. You can't write a check all at once. I can understand that. Are you frustrated by the back pay still? Kind of.

How much is owed?

That's a great question. Like, I need to go back and figure that out.

You mentioned you're responsible in this dynamic and you called him irresponsible. What are we talking about?

Just being aware. I wouldn't say, like, I'm on top of everything, but I definitely have a lot more awareness. And that's all it is. I'm setting aside my savings. I should be saving more, but I'm hitting what I set out to save every single month.

So that. Is that what you want from Justin?

Yeah.

Have you told him that?

No.

I don't want him to be not going to Starbucks when he wants to or not buying sunglasses he wants to. I just think he's been doing that without consciously making a Plan to pay off the debt that he's got.

What if he doesn't? Because some people are aware, but they.

Choose to make different decisions than you might.

It's not that he doesn't get to do those things. I don't want those things stripped away. I just want it to come after the okay, I put the chunk that I need to towards debt. I have a plan for it. Because there's things that we've discussed recently when I was like, eventually I want to build a mini farm and have an a frame house on a piece of property in southern Utah. He's like, well, where do I fit into that plan? I'm like, this is my plan because I don't know where you sit and I need to be met halfway to even think of a plan with you on this. It's my dream right now because I'm saving for it.

She was like, I just don't trust you and how can I put my name and our names together on anything?

You said that.

Different words, but kind of. I don't feel like I can trust that you've got things handled.

Why didn't you trust him?

Because he was. Seemed to be struggling quite a bit and I just didn't know. I should have asked more.

Is the goal that the two of you stay together for the long term?

Hope so. Okay.

And is the goal that you get married or no?

No.

No. Okay, wait, that was interesting. She says no. What do you say?

There's a part of me that wants to get married and we've had this conversation and this is a step in the right direction of being able to be trusted enough for her to marry me one day.

I guess what I'm trying to understand is what does your future together look like? Because maybe it involves marriage, maybe not. That's fine. But when I hear about things like building a house in southern Utah and then Justin, you very pointedly say, where do I fit in? And I hear this answer that is, well, this is my plan as part.

Of this farm conversation. Honestly, it was pretty tough. I was pretty hurt because I just felt like she's like, I'm going off and, you know, she had property for her best friend that she was including on this land. And there wasn't any conversation of me even having a room there and definitely not being a part of helping build it. I just really didn't feel like there was a we or us or I was part of the conversation. And I brought it up. I was like, you know, where do I fit in on this? And she's like, well, you don't. I need to build something so I have some sort of passive income. And then she looked at me and said, what's yours? This is my dream. What's yours? And that was the kind of like, damn it, this is why I like this girl so much, you know, because it really did light a fire under my following. Her dream of building a farm in Utah doesn't need to be my dream, you know, and so I can go over here and start doing something else, you know, and I have my own ways of potentially making passive income.

Was that a satisfying answer to you?

Yeah. It wasn't like, I'm going to go live on this farm in homestead for 10 years is not the plan. It was like, how do I pick a piece of land that's in a corridor to national parks? And I could short term rental it and we can be traveling wherever we want and stuff like that.

So it seems like the two of you have talked about it. Yeah, seems like you have a plan.

What's the problem?

I think the big one has been like making plans together.

Hold on. You both just spent five minutes telling me how you have concluded you're going to make separate plans and you don't.

Need to be together.

What am I missing?

A lot of double talk here. And that's okay. This is common in relationships. This is what a third party can help us point out. These murky alleyways that we tend to get stuck in in our relationship and how to shine a light and find our way out of them. Did you notice that they both started the episode by using jokes to avoid uncomfortable conversations? Out of respect for my guests, I don't let them get away with that. My guests take a lot of time in preparation to see me. In this case, they flew across the country to be here. So I won't let them use the usual evasion techniques to get out of a substantive conversation, even if they are employing them unconsciously. That's why I'm going to occasionally bring them back on track, even if it feels a little uncomfortable. Now Maggie sees herself as responsible and Justin as irresponsible. Justin is resentful that Maggie won't reimburse him for those utility bills that he covered. They don't talk about money. She's making plans for building a farm in Utah without him. And they say the problem is making plans together. More after a short break from our sponsors. The first time my nieces and nephews came to visit, my wife and I looked at each other and realized we have no food that kids like to eat in our house. I called my sisters, I'm like what do they eat? They're like are you stupid? They like pizza, they like chicken nuggets, they like all this stuff. I'm like disgusting. They eat that. They want the sugar laced cereal. Anyway, I bought it, they came over, they loved it, it was great. Then I sent them back home. I'm like good luck now. That was just one day. But if you are a parent looking for healthier food options, I would use Thrive Market, the sponsor of this week's episode. Thrive Market makes it simple to find trusted, family friendly brands without spending hours in the grocery store and they have great options for snacks, school lunches and so much more. You can filter on their website and shop based on what makes sense for your family. Low sugar, gluten free, organic, high protein. Just click and you will see. Plus Thrive Market's smart cart feature is pretty cool. When you create an account, they ask about your family's needs and they automatically build a cart full of of cleaner versions of your favorite brands. You can tweak it before checking out, but it's an easy way to get started. If you're ready for a junk free start to 2025, head to thrive market.com ramit and get 30% off your first order plus a free $60 gift.

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I'm very much like, I'm not going to get involved. It's a lot of extreme independence. But I'm like, I'm just going to handle my stuff. And I think I haven't sat down and even thought about what I want for my partner. I want someone to meet me halfway. There's been some contention in the last year where I said something about helping my friend out. I was like, if she has to start chemo, like, I can pay her her way. I've saved up enough to cover her expenses for three months. And I got a weird reaction from him. He felt not prioritized and all this. And I just didn't know where it was coming from. But now understanding he was really struggling financially, so that's where he was expecting a partner to maybe help a little bit more. But I didn't know that was the expectation. So we both haven't been able to know what the other person expects of each other or haven't openly talked about, I think what we want from our partners financially. And that's probably a big reason of why we're here too.

Do you have anything that's gonna force you to make a decision coming up? Cause you could go like this for years.

There's multiple things going on. So my friend is gonna start treatment in January, and the first three months is gonna be the most toughest. So I'm wanting to stay and kind of like chill on the travel, all of that, to kind of be closer. And then the lease is going to be up, but we're gonna extend it month to month until the kids are done school, so it's not disrupting that. But then throughout that process, possibly Justin's going to move and start setting up the next place.

Right now. You live together, but you're going to move somewhere on your own. And what are you going to do there?

Sleep, eat, work out.

What else?

Make money.

What's going on right now? Like, I feel like you guys are really good at talking, but you're both avoiding talking about the reason that you're here. So do you guys want to get real with me?

Why are we here?

I'm not expecting you to pay my debt. But like, there are couples who came together where one person was making $40,000 a year and the other made significantly more. But they both worked on it together, and it wasn't just about making a Spreadsheet and helping her husband figure it out on his own. It was like, we're going to do this together. And very much so. For me, a lot of this has been like, I feel like one foot's out the door always. There's this, like, safety measure of, like, all right, if this relationship ship doesn't work, then I'm out. And then the other side of it, too, is like, I just feel like a lot of the weight on all these things. It's like we just have to stay on our own foot.

Are you guys together or not?

I think we're getting more on the same page.

How can that be? He's about to move out.

I told him I want to move into a situation that one of us can handle. Because then as soon as I move into the house, if I need to pay for everything, all our expenses, fixed costs, all of that, so that you can go aggressively tackle debt. We have a plan together and we have more resources. I've been planning and pushing towards, like, something that I know I can manage so that I can help. I mean, I like giving. I like taking care of people that I care about, and sometimes I get pretty spread thin. But we'll be able to tackle these things together next year, and that's the ultimate goal.

What is the goal specifically?

That we can live in the same place and a place that's well below our means. So he can tackle debt and I can save. Like I want to say, do you.

Agree that your goal is to live together, live beneath your means so that you can pay off debt aggressively?

My goal is to live with her, but as far as live the debt and all that stuff, like, that's something that's. That's. This is new for me. This is literally like opening up your book and getting all my numbers down on a piece of paper and then being like, holy, I really need to get myself out of this situation.

So is that your plan to pay off debt?

Absolutely. 100%.

More circular reasoning here, but I'm starting to see glimmers of what's actually going on. Both of them pride themselves on their extreme independence. That's their identity. But that identity becomes hard to reconcile with wanting to be together, especially when being together involves trade offs. It's almost like these identities are butting heads. I can understand why Maggie is frustrated about how Justin handles money, but I also find that this dynamic happens when one partner begins on a financial journey and the other doesn't. This is really common. The person who's starting their journey gets Frustrated with their partner. Why aren't you engaging? Why aren't you doing this with me? Not realizing that a few years ago, they themselves were ignoring money. Now, if you want to know how to recalibrate your relationship so that your partner also gets involved with money, I talk about this very specifically with Word for Word scripts in my new book, Money for Couples. You can get it@iwt.com moneyforcouples and now listen to this. Justin tells me about his financial journey growing up, and it's something I have never heard before.

What do you remember your parents or family saying about money when you were young?

We really didn't talk about money, but I grew up with Ferraris in the garage and.

Really?

Oh, yeah. Wow. Like a extreme wealth.

Mom or dad was the higher dad. Dad was a higher, like extreme hire.

Extreme.

How much do you think he made?

A million dollars a day.

A day?

At one point. At one point? Yeah.

What'd he do?

He managed hedge fund and he had his own firm. And he also got in a lot of trouble. I kind of grew up as having the dad of Wolf of Wall street, but not a bad guy. I think that he was working in Wall street at a time when it was the wild, wild west. And when they started to put some rules down, they were making examples out of people and the government was going after his former partner and they used my dad to take him down. And it didn't quite go to my dad's advantage.

What. What happened to him?

Incarcerated. Oh, wow.

Tell me.

So he got put in a minimum security prison and decided one day that he didn't want to be there anymore. So my mom packed us up in a minivan and we went to Colorado. And my dad suddenly opens the door and gets in the minivan. And then we drove out to San Diego and hopped on our sailboat and sailed across the South Pacific for three years as fugitives.

And then when you came back because you're here in the US now, did he get rearrested?

Oh, he got arrested in New Zealand. We got busted there just to share.

How different my childhood was. We also had a minivan, but when it opened up, my dad would have handed me a spelling bee book and said, why are you not reading this?

Right.

Yeah. Mine was like, here's how we're going to be fugitives.

How much money do you think your family had when you were growing up?

Probably tens of millions.

Does your dad still have a lot of money?

The money that he had from his Wall street days kind of got squandered.

What'S his financial status, though?

He's got nothing.

Wow.

Yeah.

What messages did you take away from going from extreme wealth to not having a lot of money?

Nothing. Yeah, right. I have a funny relationship with money. I mean, I just. I don't think I value it the same as most people. When I first got started in filmmaking, I was working for this guy, and one day he goes, you grew up with money, didn't you? And I was like, how'd you know that? Because I'm not, you know, flaunting anything. And he's like, I can tell because you're just not hungry like other people are. And I was like, what do you mean by that? And he's like, well, you know, people who grew up with no money will bend over backwards. And, you know, and to me, it just seems like you always have a fallback plan. And I took that to heart and changed my work ethic quite a bit because of that. The cool thing about growing up with money is that you're not afraid to take risks. And that's very true. I feel like a lot of the reason that I've gotten as far as I have in my career and doing the things that I do is because, I mean, I'll go all in, you know? And I do believe in those lottery tickets. I do believe that, you know. Yes. I've been reading your book, and if you have a steady paycheck and you're just steady at putting away money, and 30 years down the line, you'll have a million dollars. Right. Like, I know that's true, but I also do know that sometimes if you take a big enough risk, a calculated risk, that the reward can be huge.

Maggie, what do you make of this story? What is your take hearing it?

It's made for some really interesting adult problems with money, for sure. With the money situation. It's like it just comes and it flows through Justin like water, like. Yeah, exactly. It's just as very. There's, like, not a lot of thought given to it because it's like, even when it's not an unlimited resource, it's treated as such.

Do you mean that money comes, money goes? If you're raised with millions and millions of dollars, it starts to become so abstract. You're just like, whatever, if it's not here today, there'll be another way tomorrow?

Yeah.

And I think for me, I would say money's freedom. I think when you work hard and you make money, you can free up your time. If you manage your money well, you can live really well.

What does it mean to you, Justin?

I just wish we didn't rely on it. I live a rich life, but I'm not rich for sure. I definitely put experiences and living life before anything else.

Do you agree or disagree, Maggie?

I agree.

Okay, so you're both on the same page on that.

Yeah.

Experiences above accumulation.

Well, hold on. That's shifted for you now.

Had a really different perspective shift. Prior to the pandemic. I was traveling for six years out of a backpack and working from my laptop. My goal was to eventually figure out a way to be a six figure hobo. I don't want to be tied to any destination, but I want to make good money. And then on my 30th birthday, I was on the beach in Thailand with $5 to my name, and I'm like, I have not figured out the six figure hobo thing and I'm not saving. I'm not doing anything like that. And that was when a big shift happened.

What has changed for you?

I'm prioritizing. Saving. It means a lot more what I leave.