“We have $6.3 million. Why can’t we take a vacation?”

Every time you'd sit there and say, God, I wish I'd win the lottery. And I'm like, well, we kind of have and we still don't. We still wish we could win the lottery.

Each month I'm putting money away. That's how my mind works. It's like, that's how you get. That's how you get by shit. Yet I realize there are times that I do feel like I control things too much, and that's probably a huge downfall for me. And it's stupid. She's not doing anything wrong. But this is how I react to myself. I get worked up over stupid ass stuff.

Okay, and do you want that relationship the way it is now or do you want to change it?

I want to change it, but I worry. I worry that if I'm not in control, then.

Whoa, whoa. I didn't ask about the. But I just asked if you want to change it.

Yeah, a little bit.

And that's probably my biggest fear about retiring, is that I'm not going to have my own money anymore. We're not going to spend any money now because he feels like we don't have the double income. And by the time we can spend money, as, you know, when we're older, I won't want to travel as much. And we're saving for time to live to 100 is what we're doing. We're totally saving for Tom to live to 100. I want to do stuff now.

Meet Tommy and Caroline. Tommy's 60, Caroline's 56.

This is their second marriage, both of.

Them, and they've been married for six years. The reason they came to me is that Tommy is having trouble spending. And because Caroline is just about to retire from a very stressful job, this has become a very pressing topic. What are they going to do when he continues to work and she's retired? She wants to travel. She wants to spend some of that money. He does not. Now, for everybody listening and watching on YouTube, I want to encourage you to treat this episode like a crystal ball. You have the chance to see into your future and to see what it might look like if you accumulate a bunch of money, but you don't necessarily know how to. How to spend it. So for those of you listening to the I Will Teach youh Be Rich podcast, or for those of you watching it on YouTube, I welcome you to this episode of Tommy and Caroline.

I need to chill because I think we're in a really good position. Caroline's retiring this, this March, and I'm so excited for her because she's got a super stressful job. I know we can make it work. Yet I freak out too much. I freak out when I see all these Amazon purchases and I question why it's happening. Perfect example. Caroline decides to buy a pair of headphones that we already have, a wired pair of headphones. And I know it's stupid because it's probably like a 20 or $30 purchase, but my mind just says, hey, we already have it. I need to let go of that kind of shit. I know I do. Because she's doing nothing wrong. Nothing. But I get worked up on that.

When you say, Tommy, that you freak out. Tell me exactly what happened.

It just kind of nothing was said to her. But I just inside, I internalized by saying, why did she do that? There's no reason for that. I wouldn't have done that. So why does she do that? And it's stupid. She's not doing anything wrong. But this is how I react to myself. I get worked up over stupid ass stuff.

Mm.

Okay. Caroline, do you remember that headphone situation?

Well, yeah, I. I could tell because he kind of rolls his eyes or he tries to control the situation. He'll say, we don't need it. It's a good thing I did buy him because we would be in bad shape right now if I didn't buy, because the ones that he had didn't work.

That's one. What else?

What was something that you just bought? That's. Oh, okay. She's probably going to get mad at me on this. She was telling me on a walk that she just purchased a cool dress that she really liked, that she. For an upcoming wedding. Don't know when that wedding would be, but it'd be a cool dress. Yet she also confided by saying that, yeah, don't know if I'll really be able to wear it or fit into it, or maybe it won't work for this particular wedding. And it just blows my mind. Why would you buy something when you don't know for sure that it's doable?

It was $600.

Okay. And where did that money come from? Which account?

My account.

Your personal account?

Yes.

Okay. How long have you been married for?

Five years.

Seven years.

Well, Known each other for seven, married five. Okay.

All right. You guys want to get your story straight on how long you've been married?

Well, we met 2013. We got married in 2017.

That's nine years.

No, two. Well, okay, 2017.

We've known each other for nine years. We've been married since 2017.

Isn't that five? Am I doing my math wrong?

It's five and a half, so almost six years.

When we got married, it was my opportunity. I was like, listen, babe, let's start fresh. Let's just do our wedding anniversary and birthdays. We can't do, like, the first date and the first time our parents met. It was just too much. I said, let's just start fresh. So maybe that's what's going on here.

Yeah.

All right, so you've been married somewhere in the neighborhood of less than 10 years, whatever the number is, yes. Okay. Is this a first marriage for both? Second.

Second for both of us.

Second for both. Okay, great.

Notice a few things already. When Tommy describes himself as freaking out, I asked him to get really specific with his behavior. A lot of people use the word freaking out to describe all kinds of things. Some people use it to describe losing their temper and screaming at their partners. Other people use the same phrase for the very mundane. Like, they sit in their heads and they wonder, hmm, is that worth it? I really do not like the phrase freaking out. In my opinion, it is never descriptive. And I find that people who use this phrase tend to start to treat it almost like a comfort blanket. They'll just shrug and say, I started to freak out. I can't help it.

I don't know.

That's just me. I freak out.

No, we're not going to do that.

We're not going to use inflammatory phrases and then laugh it off as just this quirky little thing. I just freak out. No, we're going to get specific with the attitudes and behaviors that we use when it comes to money. And then we're going to specifically dig to see if we can rebuild those habits so they can start to serve you.

So when you initially got married, when was the first time you talked about money in a serious way?

Caroline? I'd say the first time we talked about it was we discussed that it'd be beneficial to us to have a joint account, and each one of us have our own separate accounts that are the accounts that we had. And that way it wouldn't be, oh, I'm going to nitpick your spending and vice versa. But then again, I hardly ever spend anything, and I think that so far, that's worked out really well.

Caroline, what do you recall about the first time you talked seriously about money?

Yeah, same thing. We were going to do a joint account, and we were going to contribute a certain amount of money, and then if we could afford Trips. We'd take trips or, you know, stuff like that. So, yeah, we definitely had our separate. Which I would definitely need. And that's probably my biggest fear about retiring, is that I'm not going to have my own money anymore. I'm gonna have to sort of rely on, like, going into, I guess, our money, but it's more Tom contributing than me contributing. So, yeah, it's going to be uncomfortable, probably.

And how far off is retirement for you?

March 31.

In a few months. Okay. Wow. Early. Congratulations. That's cool.

Yes. Thank you.

All right, so when you describe your feelings about retirement, are they positive or negative?

I'm negative only in the sense that I planned on working longer. It's just my job's too stressful. I work for a company that was bought, and they got rid of people and just made other people do more than they normally have to do, and it's just too stressful. I can't do it anymore. Yeah, Gotcha.

All right. How would you describe the two of you in terms of money? Like, Caroline, if you had to describe Tommy in a word or two. When it comes to money, what words come to mind for you?

Conservative.

What else?

I don't want to be mean. I mean, I think he's kind of. I think he's kind of cheap, I think. Yeah. I mean, I know that if I want to. Like, we. If we look at boats and we bought a boat for our lake house, I knew, you know, it had to be reasonable. There was no way. Like, there's some boats out there that are, you know, 60, $100,000. There was no way. There was. Even though we probably could afford it. There's no way. It's not even an option.

How much did your boat end up costing?

Bought a used boat for $18,000. Okay.

In the. I don't know anything about boats. In the grand scheme, is that cheap, expensive for your area and your place of living?

I'd say it's cheap, yeah.

All right, here's something I want to throw by you or me.

Okay.

Here's a perfect example of how my mind works. I'm always, like, competing with myself. We got gas. I filled up the car the other day. I was so pissed at myself. Couple miles down the road, I got it. I could have gotten it for $0.12 less per gallon.

Tommy, this cannot be really happening right now.

Another incident.

Come on. Did it involve strawberries?

Tell me we're getting Yellowstone. Okay. We want to get the fifth season of Yellowstone.

Okay.

It's a good show.

I went Ahead and bought it.

You bought the HD version? No.

Hell no.

Okay? I never do that either. That's a waste of money. I'm never gonna.

And then I find out my son said, hey, Daddy O. We got. You already have it on YouTube TV. Why don't you ask me?

I'm pissed at myself for $40. I mean, it's not even worth it.

I mean, how come he didn't say something? How come I didn't check it out? I thought I did. It's not funny.

How much sleep did you lose over that one, Tommy?

I probably did. I know it's stupid, but I'm just. That's how I deal with stupid. Like that.

Tommy is doing this interesting thing here where he's pre apologizing. Have you noticed it? It's like walking into the room after you've done something and going over the top with your apologies. I know I shouldn't have done that. I'm terrible. I just can't do anything right. I'm sorry.

One apology is good.

Two is better. Ten starts to feel disingenuous. I want you to be aware of this because it might be a real acknowledgment of contrition or it might be a strategy. Sometimes it's actually an unconscious strategy that people use, but it is a strategy nonetheless. Personally, I find Tommy really likable. But. But I'm starting to get a little suspicious of the number of times he's apologized in just the first few minutes of talking. But really, I have no idea. It's just a guess. Right now, let's pay attention to what he says and how he says it.

And the other thing that may seem whacked, but I just have this feeling I'm going to live a long time to at least 100. And I'm not saying this as bragging. I just feel I'm going to live a long time. I want to make sure that I don't have to be a burden to anyone. Never do I want it. My kids or anyone to worry about me.

How many kids do you have, Tommy?

Three.

All right. How old are they?

Oh, they're all. They're 34, 33 and 30.

All right. And how are they doing?

Successful. They're all fine.

Okay, great. Do you anticipate them needing your financial help in their lives?

No.

Tommy, we spoke on the money coaching call. That was a lot of fun. So you raised your hand and we had a conversation in our money coaching group. Tommy, do you recall the conversation that we had that.

I don't believe a lot what you had to say in terms of kind of convincing me that we are good financially and that if I wanted to. I remember talking about we want to take. I want to take a trip to New Zealand.

All right, you got to hear this clip.

I was doing a Q and A with my money coaching group members and I saw Tommy's question and I knew I had to take it. Listen in.

All right, Tommy, if you are here, Tommy, please unmute because I really want to talk to you about this question. It's so good. Tommy says, I just turned 60. My wife is retiring this April. I've been self employed for over 34 years. I will continue to work because I enjoy it. My wife has worked her ass off and she wants to spend. I would love to know how much I need to budget each month so I can chill. Can you help me?

Two question marks.

Okay, Tommy, please. Are you on this call?

I'm here.

Oh, okay. Tommy, my man, first of all, I love that you put save in all caps. It must really be on your mind. Why do you like to save?

I don't know, it just, it's, it's like competitive. It's like the more I save, the better I'll be and more prepared. My financial guy says we're good, you know, and I don't believe him. And he, he shows me facts that, you know, each year it's going to be worth more.

You see it here, you see the math. Here you trust your guy, but here.

You don't really believe it.

Is that correct?

Hell no.

But I did notice you said this thing about my wife has worked her ass off and she wants to spend and what does she want to spend on?

And you know what? She does not spend a lot of time. She really doesn't. She's very good. But I just.

Oh, wait, not spending a lot means you're good. Did I catch that?

Well, no, she really. I know, I know. But what if she starts doing that?

Keep going. What if she starts doing it and then what happens? Like, what if she starts spending a little bit and then she trips and falls and starts spending $5,50,000amonth? Any concern about that happening?

Oh, yeah, no, not that much.

But how much then?

I don't know. I'm embarrassed to say that, you know, I like, I got to keep saving.

I talked to so many people who are in this same situation and they have 500,000, 5 million, 13 million, and they still cannot bring themselves to spend.

I told my group I'd like to go To New Zealand.

Oh, what's there?

The world's highest bungee jump.

Oh, my God. Okay. Amazing. That is terrifying to me. You are healthy. You have the money, you have the time because you work, and you seem to have a flexible schedule. Is there anything stopping you from doing these things?

I can't afford it.

The fact of the matter is you're 60 years old. You're healthy. You want to go bungee jumping in New Zealand, and you can afford it with the money that you probably have in your checking account or savings account, or if not, after two months, you would be able to afford it. What would that feel like if you did that?

I think it'd be cool.

Have you ever done something like that?

No.

I'm the worst. I analyze everything.

Just a quick question again. You're 60 years old. Do you have to wait until next winter to go?

Yeah, because I need to save up.

Okay, so, like, how much is in all your accounts? Just, like. Are we talking, like, $10? 10,000, 100,000? Just a ballpark. If I were to open up all your accounts together was 3 million. 3 million, plus the house, 2 million, plus the cash flow. Right. I'm not sure. You need to save up 500 bucks a month for a year. Anybody agree with me? Like, could you just go and then pay yourself back?

No, because you got to work for it. You gotta, like, save.

Tommy, Tommy, listen to me closely. There is no virtue in living a smaller life than you have to. You already have the money. You have the health. You have a loving partner.

You have kids.

You won't.

It's time to cash it in. That was a live Q and A from my money coaching program where I show you new ways to apply my material to your finances.

And I answer your money questions right.

There on the spot. You can join@iwt.com moneycoaching. That's iwt.com moneycoaching. Now back to my conversation with Tommy and Caroline.

I. Each month, I'm putting money away because that's how my mind works. It's like, that's how you. You get. That's how you get by shit you get. You don't just say, okay, I'm gonna buy it. I gotta make sure that I have the money, and if I don't, I'm gonna save up for it. I'm gonna earmark this amount of money, and that's how I'm gonna do it.

Sounds pretty reasonable the way you say it, but I also remember that you. I had to pull teeth to get you to talk about New Zealand. And then when you finally said, oh, that would be cool, it was like, yeah, we'll go on that like a year from now or 18 months or some long time from now. That sound familiar?

Yes.

I was like, why don't you just go next month? In fact, why don't you go next week?

Can't afford it.

Oh, you can't? I guess I'm looking at these numbers in your conscious spending plan with all those zeros. Oh, that must be a very expensive trip to New Zealand.

My gosh, we're going to live a long time. We got to take care of that.

Not that long. I mean, got a lot of zeros in this conscious spending plan. What's up with that nod, Caroline, you think so too?

Well, I mean, we talk about a place in Florida, and I knew if we would get a place, it had to be reasonable. So we do some Airbnbs. And this one place that we stayed at, the condos were going for 200,000. I thought, oh, he might entertain that. And it was on water. So I said something to him and he said, sure. Boom. He changed his mind completely. He was like, I don't think we need to spend the money.

So how do you two come to agreements on spending money? How does it go?

I think ideally we come to a.

I don't want to know ideally. I want to know real. Give me a scenario.

That was a mistake on my part. I violated my own rule, which is ask a vague question, get a vague answer. And that's exactly what started to happen. If I hear people going into vague language, ideally we do this or we usually do that. I never let them continue. I don't care about their answer because it's always fake. In vague language, when we are talking about ourselves vaguely, we're perfect. We always try to work out.

We try to eat right.

We try to manage our money. In real life, we haven't opened up a sub savings account in five years because our kid keeps waking up at 5am and we lost the password.

And if we roll it all back.

It'S because my mom didn't love me because I got a B on my math test in fourth grade. Those are the details that I'm looking for because those are the details that actually matter. So remember, ask a vague question, get.

A vague answer, give me a scenario.

But we don't have the condo. I'll tell you that. I get told no, and I say, what about my money?

You know, we're going to travel. I'm not going to wait. That's why I want to go to New Zealand next year. She's like, thinking, is this going to happen? I've already put it in the works with the travel agent, so it's going to happen. Not sure what month. It's probably going to be January or February of 2024, because I got to save up for it. But I'm sure I will have enough saved up for it.

How much do you need to save up for that trip?

I'm thinking probably about $20,000.

Okay. How long is the trip going to be?

A month. I'm already taking money. I'm putting money aside.

Okay, Caroline, do you agree with that?

Yeah, I would think that would be a good amount of money for a month. When you rent something for a month, it's more reasonable than, like, a hotel for a month or whatever.

Okay, you're about to be retired. Tommy says he doesn't want to retire for a long time. What's that going to mean for the two of you?

Meaning about spending money?

Yeah, or traveling? Spending money. That kind of thing.

I want to keep at the same income level I'm at, which is pretty low, and I do that for tax reasons. So I don't want to be pulling a boatload out of our savings. And I just. I would like to keep it at that. And I'm not working just because, oh, I'm nervous.

I do.

I really enjoy what I do. It's a lot of fun, and I think I'm pretty good at it. And it. It excites me. I think guys who retire early die early, and I'm not going to do that.

Okay, Caroline, what does it mean for you that one is going to be retired and one is not?

It means, like he just said that we're not going to have as much income. And I worry because we're young. I want to do stuff now. I don't want to do anything because we feel like we don't have money. And then when we're 75, because he's going to live to 100, we're going to do stuff. And I'm like, yeah, I don't see it that way at all. I had a mother that did everything. She always was going and going and going. Then she got sick, and she didn't do anything. She ended up still giving us money because later on in her life, she didn't do much. My greatest fear is that we're not going to spend any money now because he feels like we don't have the double income and by the time we can spend money, as, you know, when we're older, I won't want to travel as much. And we're saving for Tom to live to 100 is what we're doing. We're totally saving for Tom to live to 100.

I see. Tommy, what do you think about what Carolyn said? She had some pretty important things there.

I believe we need to be on the same page. And then I do believe it's pretty smooth, because Caroline's going to speak her mind, and she knows that I'm going to speak my mind. Yet I realize there are times that I do feel like I control things too much, and. And that's probably a huge downfall for me, but huge attribute because, you know, I own my own business. And I guess I've had to go with that mindset that, you know, the buck stops with me. If things screw up, it's my fault. And hopefully they. They go well and, you know, collectively, we'll do well. But I know I control way too much.

All right, you want to change that or no?

Yes. Put it this way. I love playing sports, and when I'm on a team sport, I am never, ever the coach or the manager. For once, I don't have to worry about this or that. It's just I got to worry about how well I perform.

Okay, so you like being the individual contributor when it comes to sports at work. You're the person in charge. The buck stops with you. But it sounds like you have also adopted that mentality when it comes to money in your relationship. Would that be fair? Yes. Okay. And do you want that relationship the way it is now, or do you want to change it?

I want to change it, but I worry. I worry that if I'm not in control, then.

Well, I didn't ask about the. But I just asked if you want to change it.

Yeah, a little bit.

You really should watch Tommy's facial expressions as I ask these questions. He's quite expressive, and it tells you a lot. Check out the YouTube video.

You could say, no, I'm not trying to lead you with a. If you don't want to change it.

Tell me, then I will answer a little bit. I feel like moving forward. This is. This is a big thing about how we spend our money, and I get worried about it. And even our financial guy has said, hey, you're good. You guys are good. Well, I don't know. I don't know how much we can spend each month. That's what I want to feel comfortable with. Because if I know that. Then I can chill. I can relax.

So you believe that. That if you have a certain number in front of you, that suddenly you're going to relax about money?

Yes.

Okay, here's a little pop quiz for you. If you were in my chair, how would you approach the rest of your conversation with Tommy and Caroline? What route would you take? Think about it. Some people are tempted to emphasize the numbers, Tommy, you're a millionaire. But what if I told you Tommy already knows that, and he hasn't actually changed anything because of it? What else would you do? See, one of the things I'm trying to do here is to get as many of the details out of couples that I speak to, but I'm also evaluating the details that they give me. Most of it, candidly, is noise. Some of it is interesting, but it's a route with a dead end or a bad end. You'll sometimes hear me wave couples off of a certain conversation route. They're going, if I can tell it's not going to be good. Other times I will hear something, and it's really important. But it's not as important as the burning issue. I'll give you an example from this conversation right now. Tommy has mentioned his finance guy. Now, I haven't gone down that route intentionally, but I'm willing to bet he's paying somebody a 1% AUM fee, which is a total waste of money, especially at their net worth. Now, ordinarily, I would spend time talking about that, but I don't want to do that. Just like for any soccer referees out there, you know, the advantage clause, just let it go. Same thing here. I can see this mistake happening, but there are bigger things that I need to talk about. And frankly, if I were to bring up that AUM fee, he's probably paying a financial advisor. Tommy would welcome it because he wants to do anything except tackle the real issue here. Ah, the real issue. The burning pain. That is what I'm always looking for. Because if we can solve that, the $30,000 question, or in their case, the $10 million question, then the rest of their concerns are mere trivialities. So this is what I mean by focusing on the big wins. There's usually one main issue that is more important and meaningful than all the next nine issues combined. We want to search for it and take as long as we need to do to find it. But when we find it, we want to go full head on to confront that issue.

You mentioned that you never want to be a burden on your family. I can understand that completely. And you mentioned that. You don't want to have to worry. You want to know that there's enough, right? How much is enough? Look at that smile. I like this. Have you talked about this before? I'm going to go out a little bit less here.

I don't know, 12,000amonth.

Is that enough?

Not really.

How much is enough?

I would think 15,000amonth.

Okay, Tommy.

If we can afford it.

Well, I'm not asking if you can afford. I'm just asking how much is enough.

I don't know.

How much did the two of you make together? Like how much the two of you make right now every month together? Gross.

So I think mine's kind of tricky because I'm self employed.

So how much do you pay yourself.

Net? 3,750 every two weeks. Hold on.

Every time people give me these weird.

It's like 7,500.

7,500Amonth gross.

No net.

Oh, that's net. Okay. Okay.

So gross, I think, was about 7,300.

Every two weeks would be higher. Gross would be higher.

I know, but the accountant takes out to the 401k to do other things. So.

Yeah, that's why I like to see gross. But whatever. All right, you basically make like 10, 12,000amonth gross. But you could pay yourself more, you could pay yourself less. You choose to pay yourself that much. Right, right. All right, fine. And Caroline, you make approximately 7,000amonth. Fair enough.

Yeah, probably mine's going into 401k and medical bill.

Gross. You make more than that, Caroline. You're about 160 a year.

I just want to point out, as you two dig through your pay stubs and stuff, I just want to point out, for everyone watching and listening, like, here we have a multi millionaire couple who doesn't even know how much they make. It's because I don't.

I don't look at the bank account.

It's awesome.

He should look at the bank account.

I do look at the bank account.

Yeah, it's like 13,000amonth. Yeah, I probably make 13,000amonth. I did 160 by 12.

Whatever. It doesn't matter to me. You all make a lot of money. Fine with me. Your money. Your income's about to disappear, Caroline. Fine. And Tommy, you can basically pay yourself whatever you want to pay yourself. You choose to pay yourself that much.

Could you pay yourself more?

Theoretically, you have the cash flow for it.

Yes.

So, Tommy, can I ask you a couple of questions? So you're 60 years old. Yes. You're a multimillionaire, successful entrepreneur. Do you accept those things?

Yeah, the multimillionaire.

No, I mean, I'm looking at the numbers. There's a. There's multiple commas. Let's put it that way. You are a multi million.

You look at it that way? Yes, I guess.

Yeah, the way. Like facts. Okay, so you are a multimillionaire, successful entrepreneur.

How long you've been running your business?

Little over 30 years.

Fantastic.

All right.

How many businesses do we know that even last that long? That's amazing. Okay, you're telling me that in 30 years and millions of dollars of accumulation, you have never been able to figure out how much money you can safely spend every month?

We've been told about figure on $12,000 a month and you should be fine.

Okay. And do you accept that number?

I think so. I think. I think we can do that.

You told me a second ago, I need to know the number because then I'm just going to hand over financial control to Caroline. Well, you know the number.

I don't know if that's the right number. I think it is.

I see, I see, I see. Okay.

I've never been in a position like this. It doesn't seem real.

It seems.

I mean, I'm proud of what we've done. We've. We've saved a shitload.

Yeah.

And we've done it, I want to say, kind of the hard way. It's like making smart choices, you know, not over spending on stupid shit. And that's, you know, knowing our means.

Okay. And if we go back to you, you saved a lot. You're proud of what you did. You never thought you'd be in this position. And therefore, to think about spending more means what.

Man, if you don't follow the course, Tommy, you're going to fuck it up. So you better keep, you know, saving. Yeah, that's. I'm just being honest.

I appreciate it. I think that's real. What got you here could work. It would work with the mentality of where you were at 30 years old when you started this business. And at that point, probably you were actually about 30 years old right. When you started this business.

Yeah.

Hustling, trying to get your first client, et cetera. Every entrepreneur goes through that stage. I get that. But every entrepreneur is, in a way, trying to get to where you are. And what a shame if you still act the exact same way you did as when you were 30 years old, just starting out.

I guess I don't look at as being, you know, A shame. It's like, I got to keep hustling. I got it. I got to keep having that edge. I got to keep doing this.

Can you hustle and still enjoy some of the benefits of what you've worked for?

I guess I know I should enjoy it more, and, you know, Caroline pushes me to do that, and I know I'm. I'm kind of a dick.

Tommy is showing you what happens to successful people who wrap frugality and saving into their identity. When they finally succeed, it is virtually impossible for them to change their identity. And you will see that successful people like this display a complete inability to get off the hamster wheel. Because when you've always lived for the future, telling yourself that someday you'll spend your money, you have actually let the skill of spending money meaningfully deteriorate. Now, if you are listening or you're watching this, Tommy's actually giving you a huge gift. He's giving you the gift of a crystal ball into your future. Many of you, especially the ones who have read my book and joined my earnable program and money coaching, you're going to end up with a lot of money. But if you don't learn how to meaningfully save as well as spend it, it's very likely you will end up with more money than you can use and no real ability or willingness to spend it.

Caroline will tell you this. That two things that I love to spend money on and I don't. She said traveling. I do. But when it comes to sporting events and concerts, don't care. I will go to as many as possible, and I'll try to get the best seats if I can, and I love doing that. That's my indulgence.

Okay. You don't worry that you're spending too much on it?

No, because I feel I deserve it.

Oh, you deserve it. Where did that come from?

Cause I wore a card. I mean, to me, that's pretty minor. Just saying, hey, I'm gonna spend it on concerts and sporting events.

Okay, good answer. What else is best case for you? Concerts. You want to go to one every year? Quarter. What are we talking about?

Oh, at least I'd like to go once a month, minimum.

Wow. Okay. What kind of seats you want to get there?

Oh, that'd be cool to have, like, really good seats.

You ever done that? Yeah, I got you. So concerts, maybe once in a while, get some great seats. Go every month. Fantastic. What else?

Sporting events. Yeah, I think it'd be cool. You know, I. I know so little about soccer, but I Think it'd be cool to check out a World Cup?

Sounds good to me. Do you think we might be able to apply that to some other parts of your life?

Caroline's laughing. I know I. I guess I should, but.

Caroline, what does it. What does it mean to you to hear Tommy sharing these things? Any surprises?

No. And I mean eventually, like your 401k, they make you take it out. So then I'm thinking, okay, when they make us take it out, Tom's probably going to put in another savings account. He's not going to spend it.

Yeah.

I mean, I can just hear it.

I know. I know from him. Now I know what retired men do. Like optimizers like you, Tommy. I know it because I talk to them and they take their RMD and then they literally put it right back in to they invested again. I go, what the fuck are you doing? And they go, whoa, I don't even know what to spend it on. And. And this is where it goes from funny to haunting. They go, what would I spend it on anyway? And I go, let me get this straight. I don't say this to him because I'm not trying to psychologically devastate a 72 year old man, but I go, let me get this straight. You worked your ass off for basically 45 plus years to accumulate a bunch of money, provided for your family. You did all that, but along the way, you forgot what you actually wanted to spend it on. Maybe you never even built the muscle of knowing how to spend it meaningfully. What's the point of all that money?

I agree.

I sort of agree.

How about the way that the two of you deal with money together? Best case?

Not me bitching. That would be the best case scenario. Not me worrying about stuff because I slowly am believing that we do have enough to. So I can just relax more.

Okay, that's good. Maybe another 30 years and you'll believe it. What do you think?

I think 10 years. I think I'll be good. Okay, so.

So What? What changes 10 years from now that you don't already have?

I'll have more.

Mm. You'll have millions, compound.

Yeah, but I think it'll help. It'll help us.

Have the two of you ever considered just a legitimate question, Is there a point at which the two of you have invested too much money? Has that question ever come up between the two of you?

No.

That's what I thought.

Yeah.

Never.

Because. Because that's not a question that middle class people ever really confront. It is, you save, you invest, you Kind of scrap and scrape it all together, and hopefully by the time you retire, you've got enough to live a comfortable life and maybe travel fair.

Fair.

That's the archetype for how we live in America in the middle class. But first of all, I'm looking at that very nice tree behind you, Tommy. Now, I don't know if that's a middle class tree or not, but I'm going to tell you something. I bought my first Christmas tree this year with my wife, okay? We went to the little tree lot. We got a little tree. I'm talking, like, it's like, three feet tall, okay? So we have no idea. Does this tree cost, like, $10 or 150? We have no clue. So we get the tree, and then we're like, oh, man, we got to get some lights for this thing. We go to Target, we get the light. We don't know how many lights to get. So we get one strand, and then we come home and we. We have to wrap, and we're like, in a budget way, let's just stretch this strand out. You know, it doesn't even go to the top. And I'm looking at your tree. I'm going, that is a very nice tree.

Lot of ornaments.

Probably took you 20 years to collect that. Plus the fact that I'm looking at many millions of dollars in your bank account, I'm going, maybe some of the old middle class rules don't apply to YouTube. Have you considered that?

Hell, no.

All right. Is it time to consider that now?

I don't know.

I mean, you're talking to a guy who grew up middle class, and now some of the rules don't apply to me. That used to. Maybe this is a good conversation for us all to have. What do you think?

Maybe a little bit I should chill a little bit more?

I mean, that's what you told me you wanted to do on this call. I'm giving you the option here, Tommy.

Caroline's like, yeah, keep talking.

Yeah, yeah, she's loving it. Yeah, go ahead.

Definitely. I don't want to be upset about money.

All right, let's talk about it. There is a point where when you accumulate enough, it actually starts not making sense for you to continue saving and investing at the rate you were. Now, this really only applies to people with a considerable amount of money, okay? The vast majority of people, they need to save more and they need to invest more. And it's very difficult for a lot of people, especially housing costs, all that stuff. You know, in your case, you're mentioning to me, Tommy, that you still put a ton of Money in your 401k, Caroline. Same thing for you. And all that is great. I love a good 401k. I love all these tax advantaged retirement accounts. But the fact of the matter is, Caroline, you're about to retire. Tommy, you're 60. And when I look at how much money you've got and the fact that you're going to continue working, et cetera, et cetera, I start to ask myself, what if you took, let's just say, $5,000 a month, just a round number, and instead of putting it in a 401k or whatever savings vehicle, you just used it for cash flow and you used it for traveling and used it to not have to go two miles down the road for cheaper gas, and you used it for whatever it is you wanted to use it for. What would happen?

I'd have to work harder.

Okay. Because.

Get more jobs.

Huh? Because what?

Because that's. I. Because I need to keep, you know, invest. I need to go, you know, invest in the 401k and other things and.

Why?

Because it's like, I don't. I don't believe I'll have enough or we'll have enough. Yeah, you gotta keep doing that.

Good answer.

And Caroline, you disagree?

I totally disagree. I think, like I said, my mom, I mean, not to use her as an example, it's probably not the best example, but she didn't have that much money, not anywhere close to what we have, and she still gave money to her kids when she passed. And the same thing with my dad. He didn't have a whole lot of money. And, you know, well, everyone, his, Tommy's kids will tell him, like, dad, go have fun. Go spend your money. We don't want any money.

What do you say to that, Tommy?

I tell them to mind their own business.

You know, I. I told the same thing to my parents. Did you know that?

What?

I. I sat down with them and I. Because my dad was telling me, you know, he. He called me and he told me some bad deal, he got on something. And I said, you know, dad, you don't have to go for all the deals anymore. You have enough. And he and my mom, they didn't believe it. And so I sat down with them and I made their finances really simple. Even though my dad is. He's quite savvy with money. But being savvy with money versus knowing if you have enough, those are two very, very, very different skills. Very different. I said, we don't want any money. We want you to spend every last cent. And I even put them on like a travel budget, but not the kind you think. It's a budget where you have to spend this much every single month. And that actually has proven it's, you know, it's taken a little bit of work, but it's proven to be a different way of looking at money. What do you think about that?

I think your dad should be instructing me right now.

Probably true.

This is a very interesting and advanced topic. And this is really only applicable for people who have enough money but have an inability or unwillingness to spend it. In this case, we do a bit of a reverse budget. In many ways, it's what the conscious spending plan is for. That's why if you download the free conscious spending plan, I put the link in the show notes, you will start to automatically build this skill of spending money in areas that are meaningful to you. I'll give you an example. Let's say that you want to become a better photographer.

Okay, great.

In your conscious spending plan, specifically the fourth category, guilt free spending, you can allocate 200 bucks a month for photography classes or equipment, whatever you want. And you can look at your conscious spending plan and you can see what is important to you. Now guess what? Maybe you try for six months. You go, I'm not into this. Let me put it aside.

Cool.

You just change your conscious spending plan and you shift it to something else. Your conscious spending plan and your calendar really reflect your season of life.

Life.

And that concept of a season of life is really important. When I was in my 20s, I was very aggressive at saving and investing. And even though my income was relatively low to what it would become, just as almost everybody's income in their 20s is low compared to what it will become, I wanted to get my habits right. I was aggressively investing a larger percentage of income because I wanted those habits and I wanted that compounding to kick in. I was also spending a lot, going out Taco Tuesdays. I was living in San Francisco, then New York. I was having a great time. Now I couldn't do it all. There were things I couldn't afford then that I can afford now, but I was spending as consciously as I could have. Looking back, I think I could have done things a little differently. I would have probably spent more on having fun. But at least I gave it some thought. If you get to the point where you have more money than you actually need, this happens to a surprising number of people. It's just not talked about in the press, you start to encounter some very unconventional decisions that you may have to make. For example, for the vast majority of people to be able to max out their 401k is a dream. To be able to max out XYZ account is a dream. There may actually be a point where.

You go, I'm not going to max it out.

That money has higher utility to me now than to save it for retirement later. So, again, this applies to, like, less than 3% of people. But on this podcast, I like to show you all Gamuts. Whether you're $800,000 in debt or you have over $10 million in net worth, I want you to know how to play the game of money, no matter what level you are at.

I'll tell you a scenario that, okay, you're going to yell at me, but I feel justified. This past summer, Caroline's son and girlfriend came up, and of course, Caroline said, let's go to the best, most expensive restaurant, which is we love. We both love. And I'm like, why can't we just grill here and just chill? And long story short, it was at least 500 bucks for all of us to, you know, eat, drink.

How often do you see these kids?

Once a year?

Well, no, we see them more than that, but this occasion was once a year.

Was it worth it, Tommy?

It was fun. It really was fun.

Do you think 10 years from now, when you have millions more, just purely based on compound interest, do you think you would feel differently about that type of meal?

I guess I look at it this way. I wouldn't have expected my parents to do that, and nor would Caroline expect her parents to do that.

Did either of your parents have millions of dollars?

No.

No.

Did either of your parents have their own business that they ran for 30 years to this level of success and Caroline's income as well?

Never.

No.

It's hard to take an identity that's not our parents because in a way, deep down, it might even feel like we're rejecting what they taught us. They would never take us to eat at a place that's $125 a person. I get that. And you don't have to do it every day. It doesn't sound like you're doing that. But if you had the ability to ask your parents, mom, dad, if you had the money, would you have taken us out to a nice meal once in a year? What do you think they would say?

Yeah, I think he would.

You have the means. What's really more important Than the amount spent on this one time dinner. Is the fact that you have kids coming home, still a great relationship with them? To me, that's way more meaningful than how much you're spending. You could go to a pizza place for 20 bucks. It doesn't matter to me. But the fact that you all chose to go to this place and you created a memorable dinner, to me, that's way more meaningful than the amount you spent. And I actually think that the two of you have earned the right to focus more on meaning than on money. Most of us go our whole lives only thinking about money. By necessity. We gotta save.

We.

I gotta buy clothes for the kids. We don't have enough. But you won that game. You won and you can keep playing. Tommy, you never heard me once say anything about I need you to retire tomorrow. That's your decision. You won that game of money, and now you get the chance to focus on meaning. And if you don't do that and you just keep playing the same game for the next 10 or 20 or 30 years, you're leaving so much on the field. That's how I look at it.

That's a good. That's a good analogy. I like that.

Meaning over money. Think about that phrase. It's not something that would have resonated with me at 20. At 20, I was willing to work unlimited hours. I wanted to grow everything, grow my skills, grow my friend group, grow my net worth. Meaning over money would not have made sense to me in that season of life. And there's another example I want to give you. If you take someone who is struggling to pay their bills, this concept also makes no sense. It's just words. Meaning over money does not make sense, nor is it relevant to someone who's struggling to just pay their bills. But I'm not talking to those two groups right now. I'm talking to Tommy and Caroline, who are multimillionaires. And Tommy's in his 60s. It is a tragedy to live a smaller life than you have to. And for someone worth millions of dollars to even think about the price of a $500 he has once a year with his kids, that is too small for Tommy. Excuse me for being direct, but that is the truth. Focus on the menu, Focus on the ambiance. Focus on the stories you shared over dinner. Focus on anything, but not the price. You are too successful to fixate on the price of one dinner. Yes, there are situations where the price of something is totally and completely irrelevant. And this is one of them.

Let's open up that conscious spending plan. All right, fantastic. Okay, let's. Before we. Before you look at all that, Caroline, just. Just ballpark. Just looking at me without looking at the spreadsheet, how much money do you think you both have?

Okay, so I don't look at our cars and houses income. So I would say we. We have probably 3 million.

Okay. All right. And how does that make you feel?

I think that's a good amount.

Okay, great. All right. And your understanding of how much income you make per month, total. Ballpark it for me.

Okay, so I made last year, like, 165.

Mm. And, Tom.

I'm going to say 180 or 200.

Let's say 200. And then we got the house, which generated 60k. Fair. Or even 100k, let's say, because it was grow. Let's gross it up.

Okay.

All right, so that's 465,000 last year. How's that gross? How's that sound? Ballpark.

Sounds like a lot.

Yeah, it does. It does. When you add it all up. Three numbers.

Yeah.

I mean, you guys see something? Look at this discomfort on your faces, by the way. I love it. What did you, both of you think you make together? Like, let me guess, like, 180 to 200. Is that what you thought you make?

Well, no, I knew I made 165, but I didn't know.

I thought maybe 300 total.

That's. And do you know why there's such a disparity?

I have no clue.

What are the reasons that I like people to give me their gross number is that when you take the net, you're actually taking out, like, 20k here, 20k there for your 401k and all these other things. And you just don't count that mentally. That's one of the reasons the two of you have been so successful at investing, because you're just taking out 20k at a time and throwing it into your 401k and letting it compound.

Amazing.

For investing, growth. Horrible. For understanding how much you're actually making every year. So when you hear 465, hey, look, maybe I'm off by 30k. Who the hell knows? But I'm in the ballpark. Would you say that's fair? I'm in the ballpark, Right?

I guess. I guess so.

All right, I'm right. I'm in the ballpark. That's a lot of money, right? 465,000.

Even if it's 430,000, that's a lot.

In fact, it's Over a hundred and.

$30,000 more than you thought you were making.

So it's important to be fluent in the basic language of finance. Now, Caroline, you mentioned earlier that you don't see the house as income. I agree. But I do see it as part of your net worth because it's paid off.

Right.

Would you agree with that?

Yes.

Okay, so you have $2,700,000. No plans to liquidate it. Fine. But it is there, and it's worth 2 million. 7 million. Fair?

Fair.

All right. All right.

Very good.

How about your investments?

Where? We're at 3.5.

That's a lot.

Yep.

What do you feel about that, Tommy?

We did good. I think we did really good. I'm proud of that.

That's awesome. Solid work. All right. Your savings. How much is in there?

Mean in our bank? We. I think about $14,000.

Yeah, that's what I see. Why is that number so low?

Low. That's the way it should be. Uh, why would I want to put money that's earning nothing in savings?

You're a classic optimizer, Tommy. You're always optimizing. But if you only have $14,000 in your savings account, which for a multimillionaire is low, then guess what it means. What are the ramifications of that?

Means I'm doing good. No, I'm putting money in a good source. Making interest.

Tommy, you have to wait over one year and three months to take a fucking trip to New Zealand when you have a net worth of over $6 million. It makes no sense.

You gotta save for stuff. You can't just, like, boom.

Yes, you can. Okay, let's flip this. Take me. If I want to take a trip to New Zealand, do you think I'm going to wait 15 months to save up money to go to New Zealand?

I'm going to say no.

Why?

Because you're. You're way more of an optimist than I am when it comes to money.

What's the implication? Like, neither of us is running out of money anytime soon.

I'm doing it a smarter way than you are.

I like the confidence. Okay, maybe you are. Who knows? Maybe not, though.

Yeah, I mean, definitely not. That's a smart way of doing it.

Saving.

And because you know what? Here's a great way of looking at it.

Okay?

If I do it my way, it's.

Like.

I am set now. I don't have to worry because I put that money aside and I'm. We can both totally relax and we have a lot of money. It's like, I don't care what we spend now because I saved it.

I agree with that philosophy. All of it. When you go on your vacation, I don't want you worrying about eating out, ordering an extra drink, taking a little tour. I don't want any of that. I want you to be able to be comfortable. My question is, you casually mentioned that, oops, I Forgot to include $5,000 a month in net income from this property you've got. Fine, we added it. No big deal. But, like, where's that money going? Couldn't that money be applied directly to the trip so you would, quote, have enough within four months? I.

Yeah, I guess. I know I act like I'm uncomfortable, because I am, because what if I need that money for work? Like, because it's kind of been staying in the company.

I know, but, Tommy, you know and I know every entrepreneur knows they need to also take some of that money out of their business, or it will just get sucked up.

Yeah. I mean, I. I. Let me do it my way for a little bit. Okay.

Okay.

Maybe.

Maybe 10 more years.

Yeah. All right.

No, I mean, this. This is helping because the one thing so far. Not so far, I mean, a lot has. Has hit me. Your comment about looking back and saying, hey, the memory of going out to eat, the memory of doing something with the kids, that's huge. I mean, that's. That's everything to me. I love that.

Yeah.

Yeah. Let's create a little bit more of those. The fortunate thing is you've actually got the right ingredients here. You have the money, you have a pretty high income. You've been consistently investing for decades, and so everything overall looks great. I am very happy to be able to work with these kinds of ingredients. The tricky part here is the psychology. And for everybody watching and listening, you can hear that it is real. You could have millions of dollars, Tommy. You have it. And it's still often hard to really feel like it's enough to really feel like you hit where you need to be. All right, you have zero debt again. You have only $14,000 in savings. I just want to point out it's a little bit irregular. It's not that big of a deal, because we could fill that up with $150,000 like that. But. Okay, what's your total net worth? Tommy, could you say that number out loud for me, please?

I believe it's a little over $6 million.

Caroline, what do you think about that number? Can you say it out loud for me?

Million.

Yeah. What do you both think about.

I mean, it's funny. It's like every time you sit there and say, God, I wish I'd win the lottery, and I'm like, well, we kind of have, and we still don't. We still wish we could win the lottery. It's kind of goofy.

Maybe it's not about the actual dollar amount, but it's also about the way you feel about money. And maybe we can use some of the money to help you connect that feeling and build the skill of spending it. I know how your finance guy, I know where he came up with that 144,000 or 12,000amonth. He basically took 3.5 million. How much you've got invested, and he calculated.