Episode #100: Episode 100 Celebration: Top 5 Can’t-Miss Moments

Celebrating 100 episodes of the I Will Teach You To Be Rich Podcast, we look and listen back to five of Ramit’s favorite, most shocking, episodes, covering: Disparate incomes, Credit card debt, Living beyond one’s means, Reverse gender roles, and High income problems. 

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Show Transcript

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[00:00:00] Ramit: Connie, if you paid for dinner with the two of you, how would you feel about it?

[00:00:03] Connie: I feel like I’m not getting what I want out of the relationship. And then I also feel like it’s irresponsible of me to let him take me out to dinner.

[00:00:14] Ramit: So you make 2.4 million a year, income.

[00:00:17] Connie: Yes. Yeah, that sounds horrible, but yes.

[00:00:21] Ramit: You make too much money to be behaving this way.

[00:00:24] Wes: So the question simply asked is, are we setting ourselves a failure?

[00:00:28] Ramit: Well, what’s the worst case for you two, financially speaking?

[00:00:33] Sarah: Um, continuing down the path we’re on.

[00:00:36] Wes: This slope. Yeah, for sure. The path that we’re on is the worst case.

[00:00:40] Sarah: There are sacrifices that are going to have to be made. That is a struggle. That will definitely be a struggle. Mm-hmm.

[00:00:52] Thomas: We want to live the way we’re still living. 

[00:00:55] Kristine: I don’t care about cars. We could drive less expensive cars, and that’s fine with me. This is our forever home. I mean, we don’t– yeah.

[00:01:07] Thomas: We don’t ever want to move again. Our jobs are our jobs and our income is what our income is. 

[00:01:13] Ramit: But I think you two are living above your means.

[00:01:17] Thomas: Yeah.

[00:01:18] Kristine: Yeah.

[00:01:20] Ramit: Have you ever acknowledged that to each other?

[00:01:23] Thomas: No.

[00:01:26] Serena: Sometimes now when we talk about money, I feel like I’m stepping into a landmine. I’m making more than Nate is now, but he’s going to be making a lot more than me. And it’s like, I love Nate. He’s my person. We’re engaged, and I’m thrilled. So why is it so hard for me to do this?

[00:01:47] Charles: She would love if I said, honey, you have a blank checkbook. Do what you want.

[00:01:55] Michelle: I didn’t even know how much we made. You’re netting 80,000 a month and you’re questioning my Audible $12 subscription every day? I had to sign $175,000 per month. When we fly, we fly as basic economy as we can. When we stay in hotels, it’s the cheapest. My yard is in shambles. There is no reason for this. There’s a problem here.


[00:02:21] Ramit: Big news that I want to celebrate with you today. We are at our 100th episode of this podcast. Almost two years ago, I started talking to couples about their money challenges on Instagram. It was COVID, a couple reached out to me on Instagram, they said, hey, Ramit, can you help me? I said, ah, all right, if you do it live on Instagram. They were like, okay. I said, and you have to share all of your numbers. They were like, fine. I said, what? And within five minutes of speaking to them on Instagram Live, I knew this is what I should create a podcast about. And here we are a hundred episodes later, getting to celebrate. 

Now think about all the things that have happened in the time since the podcast started. Number one, we now have a Netflix show called How To Get Rich, which made the top 10 shows in Netflix. This podcast hit the top five podcasts in all of Apple podcasts, and we launched a video version of the podcast so you can actually see the couples and you can feel what they are feeling by observing their body language and their eye contact.

Recently, we’ve added a second weekly episode, so you can listen on Tuesdays and Thursdays. Make sure you subscribe on Apple Podcasts, Spotify, and our YouTube channel. Now, one thing my wife taught me is that we’ve got to celebrate these things because we don’t know when it’s going to happen again. And so whether you are celebrating a small win, like paying off 200 bucks of debt, or whether you’re celebrating huge wins, I want to celebrate. And that’s exactly what we are going to do today. Let’s celebrate the first 100 episodes of I Will Teach You to Be Rich, the podcast, with five of the most memorable episodes so far.

 The first episode that I want to highlight is when couples have highly disparate incomes. Think about this. If one partner comes into a relationship and they make twice as much as the other partner, what does it mean? What if it’s three times, 10 times? What if it’s even more than that? What’s interesting to me is that a lot of us believe that we’ll just celebrate. Oh, that’s fantastic. My partner makes more than me. That’s awesome. We’re all in this together. But what you often see is that things are not that simple when there’s a huge disparity. 

And one of my most memorable examples of this is Connie and Wes from Episodes 64 and 65. Now, he recently started a business. He makes $2,000 a month. She makes $200,000 per month, not per year. She makes $200,000 per month. In other words, she makes a 100 times what he makes. How do you think that affects their dynamic? How would it affect yours? I want to reintroduce you to this fascinating couple. And as a quick reminder, this episode took place a while ago before we were sharing video of our podcast. So let’s listen in on an audio clip of them talking about this dynamic.

[00:05:34] Ramit: When it came to eating out, is that important to the two of you to do it once a month? 

[00:05:42] Wes: Uh, so I asked her if I could just even once a year take her out somewhere nice. And that was a hard commitment.

[00:05:53] Ramit: Once a year. Connie, why? What? Are you too busy for that? 

[00:05:58] Connie: It’s not a time thing. If I knew that he had X amount that was going to retirement savings every month, then with what’s left over, I would be comfortable with him taking me out.

[00:06:10] Ramit: Well, who’s picking up these checks? What checks are we talking about?

[00:06:14] Connie: That’s where the problem is.

[00:06:15] Ramit: Tell me.

[00:06:18] Connie: And not to say we don’t go out, but I mean, we had our first real dinner date in the last month. 

[00:06:25] Ramit: What? How long have you two been together? 

[00:06:28] Wes: Over a year.

[00:06:30] Ramit: Okay. So you went to that salad place the first time. Okay. And then–

[00:06:35] Connie: It was a nice place. We just only got salad because I didn’t think it was fair for me to buy an actual meal. So I just got an entree because I feel like it’s irresponsible for Wes to be spending money cultivating this relationship when I think it’s more responsible for money to be going into savings for him.

[00:06:59] Ramit: You feel that way about his finances? 

[00:07:04] Connie: Yeah, because I have control issues and I want to– yes. 

[00:07:08] Ramit: Okay. And Wes, what do you feel about, for example, going out to dinner?

[00:07:14] Wes: What I grew up staying is my dad would take the family out occasionally, once every other Friday, like I said, and he would pick up the check. And so when I have told Connie repeatedly that I would love to take her out to dinner, let’s go do that, but when we do go to dinner, I would like to pick up the tab, but I get the, I’m not going to call it a scolding, but I get the little bit of a lecture that’s like, hey, you shouldn’t be paying for this.

So one, we shouldn’t go out to dinner. And two, when we do go out to dinner, she’s going to pay for it, not me. And it’s like, well, I really just want to take you out, you order whatever you want on the menu, and let me pick up a tab. And she thinks that’s a bad financial decision.

[00:08:02] Ramit: You want him to do exactly what you do with money. Is that fair to say? 

[00:08:09] Connie: Yeah. That sounds horrible, but yes.

[00:08:14] Ramit: But he’s not you. 

[00:08:16] Connie: Yeah.


[00:08:20] Ramit: Connie wants Wes to take her to dinner. Wes agrees he wants to take Connie out. He wants to pay, but when he reaches out for his credit card and tries to pay, she would rather that he saved the money. Let’s listen into one more clip. Before you listen, keep in mind again that Connie is worth 6 million. She makes $200,000 per month. Wes, who’s just started his own business, makes $2,000 per month 


[00:08:52] Ramit: What would it look like if the two of you said we are going to go out to eat once a month? Would it be possible? A lot of silence on this call. Got really quiet 

[00:09:11] Connie: So would be possible.

[00:09:14] Ramit: Mm-hmm. What’s caveat? Go ahead.

[00:09:17] Connie: So it goes back to the trust of finances. And so, for example, Wes and I went out to Vegas. I had a business meeting out there, and then Wes and I were going on vacation for two or three days. And what, Wes, it was a $300 credit that we had at the dinner place?

[00:09:34] Wes: Yes.

[00:09:35] Connie: So we had a $300 credit for– it was a nice dinner place. So we went, I had drinks with my business partner ahead of time, and I knew that we were getting close to that $300 mark. And I love the thought of Wes just being the man and just making decisions. I love the theoretical thought of that.

And I had a glass of wine, and the waiter asked if we wanted the whole bottle. And again, I love the notion of Wes just taking charge, but I was more on the, I’m just going to have a glass of wine, and Wes said, let’s get the whole bottle. So next thing you know, dinner cost $400 instead of $300. And we didn’t drink the bottle of wine. And a $100 is such a minuscule rounding error. It doesn’t count anywhere in regards to my net worth, but it was the trust issue of I have to pick up that extra a $100.


[00:10:44] Ramit: As you hear, that there’s so many different layers going on. There’s gender roles and expectations. There’s different incomes, highly disparate incomes. There’s a new relationship that’s about a year old. There’s a lot. Can Connie and Wes ever get aligned on money? Well, you have to listen to the full episode to find out. Check out Part 1 of their story in Episode 64 and Part 2 in Episode 65.

 The next theme that I noticed in our first hundred episodes is couples getting themselves into debt. And what’s most concerning is when they get into credit card debt. One of the most mind-blowing examples of this was Sarah and Kevin in Episode 80. Let’s listen.


[00:11:39] Ramit: Did you take the money from the house and pay off all the student loans as well?

[00:11:44] Sarah: Um, no. Uh, because we were– the goal was to take the additional. We sat down and we decided we were going to pay off the credit card debt. And then the additional amount that we had left over, we were going to invest some of it, save some of it to have cash available for whatever reason, and then, um, utilize that for a down payment on land.

[00:12:08] Ramit: Okay.

[00:12:09] Sarah: So we didn’t pay everything off, no. 

[00:12:11] Ramit: Uh, that student loan that you had, which you did not pay off, how much was it at the time?

[00:12:17] Sarah: Um, right around 30,000.

[00:12:20] Ramit: Okay. What was the interest rate? Do you remember?

[00:12:22] Sarah: It’s nothing. 

[00:12:24] Ramit: It’s low?

[00:12:25] Sarah: It’s zero right now, I mean 

[00:12:28] Ramit: But back then?

[00:12:29] Sarah: This was six months ago.

[00:12:30] Ramit: Oh. What?

[00:12:32] Sarah: Yeah.

[00:12:33] Ramit: Hold on. Let me get this straight. What the hell? I didn’t know about these timelines.

[00:12:36] Sarah: Yeah.

[00:12:37] Ramit: Hold on. I’m speechless. You paid off $130,000 of credit card debt six months ago, and now you have $50,000 of credit card debt just six months later?

[00:12:56] Sarah: Yeah. 

[00:12:58] Ramit: Whoa. So what happened?

[00:13:06] Sarah: Um, life.

[00:13:08] Ramit: Wait. Okay. This is like, if this was five years, I would be like, all right. Yeah, life happens. But six months? We could figure this out in 25 seconds. Let’s just do it right now. Life happens. All right. Not that much life happens in six months. So let’s break it down. What vacations did you take in the last six months?


[00:13:29] Ramit: I was speechless. That almost never happens on this show, to go back into tens of thousands of dollars in debt in just six months and have no clue what happened to it. I actually didn’t believe it. I didn’t accept it. So I said, let’s figure it out right now. And we did a quick back of the napkin calculation on where the money all went.


[00:13:56] Sarah: Well, we paid for a cruise that we have coming up. 

[00:13:59] Ramit: How much is that? Ballpark.

[00:14:01] Sarah: 7,000, I think

[00:14:03] Ramit: What do you think? What number do you think I would pick to write down here? How much is your cruise going to cost? You said 7,000. What do I think the real number is?

[00:14:14] Sarah: Um, eight.

[00:14:17] Ramit: No.

[00:14:17] Sarah: 8500.

[00:14:18] Ramit: Higher. Kevin?

[00:14:21] Kevin: Um, 11. 1150. 11,500.

[00:14:26] Ramit: Okay, so let’s say 11,000. What else you spend money on the last six months?


[00:14:33] Ramit: You see what just happened right there? This false desire to always minimize how much things cost. People who get into debt often do this consciously and unconsciously. They’ll say, oh yeah, we went out to dinner last night. It was probably like 30 bucks. When you factor in tax tip transportation, everything, it was 70 bucks. 

They do this in part because they’re embarrassed of how much they spend, in part because they want to ignore it, in part because they don’t know. There’s lots of different reasons that it happens. We spent the next few minutes uncovering what they’ve spent on in the last six months trips, clothes, a surgery and post-care, business coaching for Sarah, and Christmas gifts. Let’s see what it all added up to.


[00:15:15] Ramit: Let me finish calculating these. $72,500 in the last six months. What do you think about that number?

[00:15:37] Sarah: That’s, uh, unexpected 


[00:15:46] Interview: That’s how it happens. They spent $72,000 in six months without even realizing it, putting them right back into debt. Now, if you think that this is all, the episode is about, just spending money on debt, you’re only scratching the surface. The surprises keep on coming in this episode, so please, you have to check out this two-parter with Sarah and Kevin where we talk about how their upbringing affects the way that they behave with money. We talk about how they’re going to pay off this debt, and we talk about the moment they tell me their plans for school for their three daughters.


[00:16:30] Ramit: Are there any other things that are really important for the two of you to start doing?

[00:16:35] Sarah: Saving for the girls’ school next year.

[00:16:38] Kevin: Yeah.

[00:16:39] Ramit: What? Where did that come from? We haven’t talked about that at all.

[00:16:43] Sarah: No. So they’re in private school, and so we had to switch their school. For all three, without financial aid, it’s about 55,000 a year.

[00:16:52] Ramit: What the fuck? Where did the– how are these secret expenses coming up right now?

[00:16:58] Sarah: They’re already there at the school?

[00:17:01] Ramit: What?

[00:17:02] Sarah: Yeah. I mean, they’re in the middle of their first year.

[00:17:05] Ramit: All right. What the fuck? You signed them up for this school without even knowing where the money was coming from?


Find out the whole story at Episodes 80 and 81. Next up, one of my most memorable episodes is about living beyond your means, and I want to direct you to the episode with Christine and Thomas in Episode 84. I often hear from couples who are making great money, but they are stressed out by little things like groceries or their cable bill or eating out. And I can tell you that in these situations, it is almost never the small things that are going to move the needle. The truth is often they’re quite simply living beyond their means, and often it’s the house. And the car in that order. That is how it works. 

People will fight for 15 years about the price of pickles, never realizing that pickles are irrelevant. It’s that they’re overspending on their house, they are house poor, or their car is invisibly, dragging them down with all these phantom costs, and they just have no idea. A great example of this is Christine and Thomas. They have three young children. They bought a nice house, and they make very good money, but they are stressed about money every single day. Let’s listen in on a clip when we discover they are spending 98% of what they make every single month.


[00:18:29] Ramit: How much are you both spending on your fixed costs as a percentage of your gross, excuse me, your net income?

[00:18:35] Kristine: 98%.

[00:18:38] Ramit: Is that high or low? Or what does that number mean to you?

[00:18:42] Kristine: It’s outrageously high to me.

[00:18:44] Ramit: Yeah. Thomas?

[00:18:46] Thomas: Yeah. Same.

[00:18:47] Ramit: Generally, I prefer to see 50 to 60%. There are rare exceptions but they are extremely rare, and you two are not in that rare of a situation. So with 98, what is the implication? If you have 98% of your take home income is being spent on fixed costs, how do you think that that affects your life?

[00:19:10] Kristine: We can’t save an emergency fund and we also can’t save to do things that we want to do.

[00:19:18] Ramit: Yeah. What else?

[00:19:21] Thomas: Can’t go on vacation. 

[00:19:23] Ramit: Mm-hmm. 

[00:19:23] Thomas: Can’t lose our jobs.

[00:19:25] Ramit: Right. That’s a good one. What else?

[00:19:29] Thomas: Can’t get sick or have any other major expenses. 

[00:19:32] Ramit: It suddenly makes a lot of sense why, Kristine, you’re waking, looking at your phone, you’re asking about– sending urgent messages about a $200 check, which I don’t do that. I don’t. And I don’t want you to have to be fixated on $200 when the two of you make $133,000. The way you have set your expenses up, it forces you to play small.


I worked with Christine and Thomas to try to get that number down, but what I learned in this episode, what you see is that they still weren’t really internalizing what it means to spend 98% of your income on your fixed costs alone.


[00:20:20] Thomas: And we also have DirecTV, which is over a $100 a month.

[00:20:28] Kristine: See, I don’t feel that bad about DirecTV. I know it’s an expense, but I’m pretty proud of the way that I’ve every year called them and said, I’m going to cancel. And I don’t think a $100 is that bad when you think about if we’re going to supplement that with all these different subscriptions that are going to equal a $100.

[00:20:48] Ramit: I think if you were making $500,000 a year, I wouldn’t even be having this conversation.

[00:20:53] Kristine: Yeah.

[00:20:53] Ramit: But you two are living above your means.

[00:20:57] Thomas: Yeah.

[00:20:58] Kristine: Yeah.

[00:21:00] Ramit: Have you ever acknowledged that to each other?

[00:21:03] Thomas: No. 

[00:21:05] Kristine: I don’t think so. Not in terms at least of these assets.

[00:21:13] Ramit: Well, every month you’re losing money.

[00:21:15] Kristine: Mm-hmm.

[00:21:18] Thomas: Yeah.


[00:21:22] Ramit: Sometimes, especially if you are trapped in a cycle of overspending and you don’t know how to get out of it, it can feel really hopeless and every time you try to make a change. It just feels like you’re rearranging deck chairs on the deck of the Titanic. It’s totally normal and common that couples will end up focusing on the smallest things. They’ll spend all kinds of energy and actually doesn’t move the needle at all. To find out what we were able to get their costs down to, check out Episode 84. I think you’ll be really surprised by the progress that they have made.

Next example, gender roles. Gender roles and money are real, but they are rarely talked about, especially shown. And one of my goals is to shine a light on our expectations of gender roles. For example, true or false, a man should pay on a date. What would you say? What if I asked you why? These are really interesting examples of how we think about gender culture, money systems, and so we’ve featured lots of different and diverse examples of gender roles on our episodes. 

One of my favorite examples of this is Serena and Nate, Episode 73 and 74. They’re both in their late 20s, and they are engaged. Serena makes almost two times what Nate makes. She makes $80,000 a year. Nate makes about 45k a year. He’s a medical resident, but in a couple of years he’s going to be a doctor, and at that point, his salary is going to increase dramatically, likely to about $300,000 plus. Now, I really like this couple. They’re clearly in love. They clearly care for each other, but Serena has some very strong opinions on how money should be spent in their relationship. Let’s listen to a clip.


[00:23:21] Ramit: Talk to me about it. So the check comes the server puts it down in the middle of the table. What goes through your mind?

[00:23:28] Serena: Well, I know just based on where we’re at, based on what we usually do we usually split the track, which I’m fine with. Nate will treat me sometimes and is really generous about, oh, let me get you a coffee. Do you want anything? He’s great about that, and it’s really sweet, especially as someone who that is not my like first way to show, uh, love in relationships, but he’s very generous in that sense. I guess what goes through my mind is I wish Nate could treat me, but one day we’ll get to that point, but tonight might not be that point, and that’s okay. 

[00:24:06] Nate: But you just said that I do treat you more often than you treat me, so that’s interesting.

[00:24:10] Serena: No. Yeah, I know.

[00:24:12] Nate: Okay.

[00:24:14] Ramit: Do you wish he treated you every time?

[00:24:17] Serena: Um, no, but I think when the check arrives, of course, I want to feel taken care of. 

[00:24:30] Ramit: So Nate, what would you say if you were more generous when that check came? 

[00:24:33] Nate: It would probably be, uh, do you want me to cover this? Would probably do it. Um, the problem being if Serena were to apply, yeah, that would be great. I can’t really afford it. 

[00:24:47] Ramit: That’s a problem.

[00:24:49] Nate: Yeah, absolutely.

[00:24:50] Ramit: That’s like someone saying to their partner, uh, would you like to fly in that private jet? And they’re like, yeah.

[00:24:55] Serena: I would love to.

[00:24:56] Ramit: Uh, well, I can’t actually afford that. So that’s cool. I’m glad you want to, but we’re not going so, so how can you be generous, Nate, if you can’t afford the dinner?


Now, this went on for a while. It was extremely fascinating to hear both of their perspectives on who should pay until I flipped it.


[00:25:19] Ramit: Why don’t we just invert the whole thing and see what happens. Nate says to Serena, Serena, it would be really nice if you would offer to pick up the check a lot more of the time because actually I can’t recall you ever offering. And by the way, you make a lot more money than I do, so don’t you think it would be fair? Look at that big smile on Nate’s face right now. Nate’s got the biggest smile.


[00:25:41] Ramit: I love this technique of inversion, especially when there is a cultural norm or a gender norm or some other expectation that is not spoken. It’s never written down. It’s never, uh, articulated clearly, but everyone just gets it. That’s where this technique of inversion can become extremely helpful. I love this episode. I think they were so honest in what they said to each other in bringing their hidden expectations to the surface, and I want you to hear this whole story, especially what they decide to do about the rent.


[00:26:21] Ramit: Let me make sure I understand. So you’re each paying a $1,000. Your rent went up. That made it very difficult for you, Nate, to afford it. Um, Serena, you wanted to stay in this particular area, so you had a back and forth and you concluded with Serena you’re paying a little bit more, $160 more per month for this apartment.

[00:26:41] Serena: Yeah.

[00:26:42] Ramit: How much more do you make than Nate?

[00:26:45] Serena: I would say significantly more.

[00:26:48] Ramit: Great. All right. Can I just say, um, Nate, you’re making way less than Serena and you’re paying, essentially 50/50. That’s the problem. That’s the reason that when you go out to dinner– the two seem totally unconnected, don’t they? The amount you pay for your apartment and then going out to dinner and all this drama happening around the check coming, but it’s actually directly connected.

Nate, you are spending too much for your portion of housing, and therefore you have nothing left over, no wiggle room. You can’t even give Serena a straight answer on when you can pay her back $50 a month, and that’s causing stress. Do you see how it all rolls back to one thing that is seemingly invisible in your finances?

[00:27:46] Nate: Yeah.

[00:27:46] Ramit: It’s this. So Serena, let’s say that my wife and I were dating and I was like, hey, move in with me and I make twice as much as you, but we should split it 50/50. What would you say to that?

[00:28:05] Serena: Um, I don’t think I would love it if it were me.

[00:28:11] Ramit: Okay. Would you love it if it were Nate?

[00:28:14] Serena: Uh, no.

[00:28:16] Ramit: Okay, good. Great. So we could meet there. The most successful couples I see, especially in situations like this where you have separate incomes, etc, is proportional. So proportional means if you’re making 65% of the income, you pay 65% of the joint expenses. And that would probably suggest that you pay more for this rent and that Nate pay less. How would you feel about that?

[00:28:45] Serena: It’s like talking about the check. I think it would be really hard for me at first just because it’s not something I’ve done ever before and not something I think would’ve considered.

[00:29:00] Ramit: Let me ask you this before you go on.

[00:29:03] Serena: Yeah.

[00:29:05] Ramit: Um, let’s just fast forward three years and Nate’s making 300, 325k. How much should he pay for the rent?

[00:29:16] Serena: Yeah. This is something we’ve talked about. I would be super weirded out if he expected me to pay 50/50 for rent.

[00:29:24] Ramit: Wait. What are you talking about? You make more right now, and you’re paying 50/50. 

[00:29:28] Serena: I know, but I’m–

[00:29:30] Ramit: That’s a double standard. 

[00:29:31] Serena: I know, but I’m not making that much like I’m making more than Nate is now, but he’s going to be making a lot more than me.

[00:29:40] Ramit: Oh so it’s a gradation So what’s the number where, in your mind, it changes?

[00:29:47] Serena: I’ve never even thought about that, to be honest. 

[00:29:48] Ramit: Because it’s not a number.

[00:29:54] Serena: Yeah.


[00:29:56] Ramit: When you flip it, what if he is the higher earner, he picks up the check, he pays more rent, he takes the family on vacation? Suddenly, the whole thing sounds preposterous. These clips only really scratch the surface of my fascinating conversation with Nate and Serena. And you can find it in Episodes 73 and 74.

Number five, high earners. Let’s talk about the high earners that come on this show. One of the things I love is highlighting the diversity of money and couples. Now, if you pick up a newspaper or magazine, you will often see articles about people in severe debt, and I think that’s helpful. We want to talk about that. In fact, I’ve had people on this show with $800,000 of debt. Credit card debt, student loan debt, all kinds of debt. But what you almost never hear are wealthy couples talking about money that only happens behind closed doors until this show.

One of the things that you will discover is that people who make more money stop talking about it. Media does not really focus on them although even if you have a lot of money, all of your financial problems don’t vanish. Sure, some of them do, like being able to pay for dinner or keep the roof over your head. But there are still legitimate problems, and I love sharing these because I want to show you that just because you get more money, it doesn’t mean all your problems are going to vanish. You’ve got to develop other skills. 

So please know as you listen to all these episodes, if you feel nervous about money today, or anxious or fearful, you’re still going to feel that way if you have a million dollars, $5 million, $10 million. I literally cannot tell you how many millionaires I’ve spoken to who drive around town to save money on blueberries or gas.

And my favorite example of this is Charles and Michelle from Episode 20. Charles wrote me because he said, in all caps, help. My wife of 21 years is about to divorce me because I am too cheap. Their net worth is over $10 million. They make 3.1 million per year, but Charles still insists on sharing a Netflix password, and he questions Michelle’s $12 a month audible subscription. Charles is afraid that if his wife starts spending, she’s going to trip and fall and make them go bankrupt, but Michelle is so sick of his cheapness that she’s on the verge of divorce. Let’s listen in.


[00:32:32] Ramit: Clearly, you’ve probably talked about this before. I’m sure it’s been a hot topic of discussion. Charles, it sounds like Michelle wants to get some furniture. What has your approach been with this furniture that she wants to get?

[00:32:46] Charles: So my first approach was, okay. When I hear her ideas, I start to hear, see that to change. That’s okay. Let’s just outline, what do you want to do to the house for the next 12 months? And then let’s plan for that. So there’s no like big surprise. And that’s when Michelle cringes and doesn’t want to do it. And that’s what causes the strife. She would love if I said, honey, you have a blank checkbook. Do what you want.

[00:33:13] Ramit: Is that true, Michelle?

[00:33:15] Michelle: I would love him to take enough money that he needs. He said he needs 150,000. Take it. Give me the rest. I mean, literally. You only need 150. You’re netting 80,000 a month and you’re questioning my Audible $12 subscription every day? There’s a problem here. We file our taxes jointly, and I had to sign for taxes recently. Couldn’t believe my eyes. I didn’t even know how much we made. I had to sign $175,000 per month. My yard is in shambles. There is no reason for this. 

When we fly, we fly as basic economy as we can. When we stay in hotels, like he said, it’s the cheapest. Now, we’re not in Motel 6 and we’re not– it’s an dire straights, but it’s probably the quality if we made a hundred thousand dollars a year, and there’s nothing wrong with that. The problem is we make more. The reason why I’m not giving a list is because it comes down to the words that he said before, convincing, being thoughtful, being planful, I’m all those things.

I’m analytical as well. I plan. I research. I weigh and measure. I don’t willy nilly just say, hey, I want to buy a couch today. I’m doing research, etc. But those words are unacceptable and they shut me down. And when I hear those, I’m like, I’m not giving you a list because the minute I say, let’s do this, that’s not being thoughtful. That’s not being planful. Well, I’m just saying it. Give me a chance to think it out. So these are issues that, um, everything that he’s saying is fantastic. They make sense. They’re logical, but in reality, it doesn’t play out like that. 

[00:35:02] Ramit: What I hear beneath the surface is this fear that if you take Michelle’s approach, which you’ve described as being more intuitive, more spontaneous, that somehow you will lose the core of what made you successful. And that suddenly you’re going to just lose it all, and, oh my God, I dropped $75,000 on dinner tonight. Can you see a reality where you ever spend $75,000 on one dinner, Charles?

[00:35:30] Charles: No.

[00:35:31] Ramit: No. I don’t think so. It would be very hard to do that. Can you ever see a reality where Michelle spends that much on a single dinner?

[00:35:39] Charles: Uh, for the two of us, no.

[00:35:42] Ramit: It is really, really hard for people to turn the page in their rich life. Let me explain what I mean. For highly successful people like Charles, all of their skills of saving, and investing, and planning, and optimizing got them to the top of the mountain. So from the outside, you look at them and you say you made it. Why are you agonizing over $200 jeans? 

But to them, they see the very skills that got them here as identical with themselves. They can’t separate the desire for success from themselves. So I can sit here and repeat, turn the page. What’s your rich life? It doesn’t mean anything to Charles yet. Michelle can even say, “I’m about to divorce you,” and it still doesn’t really hit home. This identity is deeper than money. It’s deeper than relationships, goes to the very core of who Charles is. 

By the way, I sometimes ask people on my newsletter what would you do if you had a $100 million? The answers are so fucking depressing. Half of them say, oh, I’m already living a great life. I wouldn’t change a thing. I know, they’re trying to signal that they’re happy, but I consider this almost a criminal lack of imagination to not know what you would do with essentially unlimited money, not even a single amazing trip, not even taking your family to create an unforgettable memory. I’m not impressed. 

Half of the people respond, pay off my house then invest the rest. For what? You fucking won the game. You have a $100 million, and now you want to invest more? These are the kinds of answers people give when they haven’t really thought through their rich life. When they haven’t given themselves room to dream. Now, there’s just one more catch with Charles here. He actually has that kind of money and yet he can’t stop making more of it. 

If someone has a net worth of $11 million and earns millions of dollars a year, that person can easily afford first class. If that person is deciding not to fly out of fear that he’ll trip and fall and spend $11 million, that’s a red flag. And if that person’s wife is threatening to divorce him for his money beliefs, that’s one of the biggest red flags of all.


[00:38:16] Ramit: Will Charles be able to finally stop being so cheap and turn the page on his spending for the sake of his marriage? You’ll have to listen to Episodes 20 and 21 to find out.

All right, that’s a wrap to our five most memorable episodes of the last 100 episodes of this podcast. We’ve really only scratched the surface, so if you are new here from watching my Netflix show, please check out these fascinating episodes to help you hear the whole story. We release new episodes every Tuesday and Thursday.

Make sure you subscribe so you can be notified as soon as a new episode comes out. You can follow us on Apple Podcast, Spotify, and of course YouTube, where you can see the actual couples, their eye contact, and their fascinating body language. Thank you for listening to, I Will Teach You to Be Rich, and I can’t wait to see you next week.