Why Smart People Struggle with Money Conversations – Episode #709

On this episode of The Dentist Money Show, Carl Richards, CFP®, author of Your Money, joins Ryan to explore the emotional side of money and why even smart, successful people struggle to talk about it. They discuss how emotions influence financial decisions, why simplicity often beats complexity, and how understanding your values can lead to more meaningful money choices. Carl shares insights from his new book, “Your Money: Reimagining Wealth in 101 Simple Sketches,” which uses simple sketches to inspire deeper human conversations about money.

You can order Carl’s new book here! If you would like to order in bulk, you can receive a 5% discount by using the code YourMoney5 at checkout here!

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Podcast Transcript

Ryan Isaac: And welcome to another episode of the Dentist Money Show where we help dentists make smart financial decisions. I’m your host. They’ve called me Sir Ryan Isaac:. That’s fine. I am Ryan and I’m here with a friend and longtime friend of the show and dentist advisors and many, many other things very familiar to all of you, Carl Richards:. Hey Carl, thanks for being here, man. How you doing?

Carl Richards: Hmm. Yeah, right. Super excited to have you. I’m glad to hear that they’ve called you Sir. I, I sometimes make people refer to me as my full name is David Caro Richards the third. So yeah, so yeah, exactly.

Ryan Isaac: really? Okay, S-Quaren. The Sir actually, so the podcast turns 10 years old maybe this month, maybe next month. And the Sir comes from something that I didn’t ask for, if it sounds familiar, from Reese Harper, if that sounds like a Reese thing at all. It comes from Reese. He would just call me Sir Ryan Isaac: and make jokes. I don’t know why. There’s nothing nightly about me, or regal.

Carl Richards: Yeah. Yeah. Right. Right. Yeah.

Ryan Isaac: And then it stuck. that’s where that comes from. Thanks for being here, man. You’re joining us from Park City, your beloved home. if people attended or even just saw some of our advertising for our last Dentist Money Summit, and I don’t want to give too many spoilers, but maybe some future ones, then they will have seen your face and maybe seen you present. But Carl, would you give, for those of…
If anyone is even remotely adjacent to the financial industry, you’ll know Carl from a lot of things. ⁓ Some dentists might not. So Carl, you mind giving a little, who’s Carl Richards:? David, the third.

Carl Richards: Yeah, yeah, I would assume most dentists don’t. So I started in the financial services industry speaking sort of really broadly 25 years ago at Fidelity Investments ⁓ and then moved to a big brokerage firm and then started my own independent RIA firm and ran that for years and
And at a certain point in a client meeting, remember, fact, I remember who the clients were actually. I was trying to explain a concept to some, he was an ER doctor and she was a technology sales rep. So super, super smart, super successful, both of them. And I was trying to explain a concept that I thought was really important for them to understand for the decision we were about to make.

Ryan Isaac: Hmm. Yeah.

Carl Richards: And I was just getting blank stares. And this has happened before, the blank stares had happened before with other clients, but this is the first time it dawned on me that I just had this sudden realization, these are very smart people. If they’re giving me blank stares, it’s not their fault, it’s mine. And so I thought I was good at explaining things, but so in an act of desperation, I stood up the first time ever I’d ever done this. I wasn’t a doodler in high school, I have no art background.

Ryan Isaac: Mm-hmm. Mm-mm. Mm-hmm. Okay.

Carl Richards: I stood up and sort of tried to just draw, like explain it, diagram it. And I drew some circles and some squares and an arrow or something and they said, oh, we get it now. And I didn’t make any grand conclusion other than like, that’s kind of cool. And I thought, I’ll do this again. I’ll just do it next time. I could do this next time a client asks. So that led to, you know, a couple of years later, the New York Times asked me to…

Ryan Isaac: Yeah. Mmm.

Carl Richards: To draw those sketches for them in a column that ran for every week for 10 years. And somewhere along the line there, I decided to sell my investment business and just focus on writing books and talking and podcasting about how to think about money. so there’s two books, the third actually on the day we’re recording this is publication day at October 21st. so two or three books later and a

Ryan Isaac: Mm-hmm. Yeah.

Carl Richards: Thousands of conversations about money. still sort of fascinated, endlessly fascinated by this thing we call money and how we can get our hands around it. So that’s the background.

Ryan Isaac: Yeah. huh. Yeah, thanks man. Well, we’re going to jump into a lot of this. I want to go back to some of that story. What do you think? where’s the deficiency? What’s the, I think the, the experience you had with your clients, very highly intelligent people, clearly very successful have, you know, a lot of education and experience, kind of having like the blank look during financial money conversations. There’s probably nuanced. It’s not something we’re taught a lot about. It could be, sorry, it could be the person delivering the information, the teacher.

Carl Richards: For sure.

Ryan Isaac: It’s most certainly is the industry. What do you think it is about that conversation and the disconnect that happens? Are there like emotional barriers? We just can’t access some things about money. Like what do think that is? Because that’s a very common thing with a lot of people and you know and also with very intelligent highly successful people too. What do you think is going on there?

Carl Richards: Yeah, I mean, think two things. One is just that the industry, the financial industry has often seen complexity as some sort of sign of intellectual prowess or nefariously uses complexity as a sales tool.

Ryan Isaac: was just gonna say like a weapon, complexity like a weapon.

Carl Richards: Yeah, like sort of dig a hole, throw the client into it and look down and say, I’m the only one with a rope. And that’s no good, right? not, clients don’t like that, humans don’t like that. It doesn’t need to be that way. And that’s a confused…

Ryan Isaac: Hmm.

Carl Richards: Assumption about what it means to be ⁓ valuable and smart. So the financial service industry thinks the complexity makes them valuable and smart, and that’s just confused. And really good financial planners do this too. We just get a little confused about it. then the second reason that happens is because we just kind of forget. I’ve been at plenty of dinner parties where everybody else was a… In fact, I…
used to spend a lot of time around emergency room physicians because I had a bunch of them as friends and clients. And I’ve been at parties where they’re talking and I don’t understand a word they’re saying.

Ryan Isaac: So I feel going to the dentist when they show me the charts and they’re like, see on number 12 and this, I’m like, I don’t know. ⁓

Carl Richards: Yeah. Yeah, I think all professions do this where you just kind of forget that somebody doesn’t really understand exactly what it means when you say certain words. But then there’s another piece of it that I think is even more important. And that piece is we might even be talking about the wrong thing, right? Like we expect money. There’s a part of this that it feels like it’s really hard to understand, even this technical piece but we expect money to be always about calculators and spreadsheets. It belongs in the math department. Because if we were taught anything, that’s where math, like any money thing was math. It was calculators and spreadsheets. And then the really hard part to talk about is that you bump up against these weird feelings where, I just opened the American Express, but why are we suddenly fighting? And, We expect two plus two to always equal four, but two plus two never equals envy. And I think that’s, it’s unmooring when you’re like, can we talk about how to fund what we think about funding our kids’ education? And suddenly you’re in some weird land around values and feelings, because one of you says, no way. I I worked my way through school, dental school. I paid for it myself. We’re not giving them a dime. And the other one of you, was like, wait, I thought we were prepared to pay for the best school they got into. And suddenly it’s not just a conversation about a spreadsheet, it’s a deep seated value. And I think that can be confusing too.

Ryan Isaac: Mm. Yeah, I’ve always thought I’ve been doing this job in this company for 18 years now this year. And I’ve always thought in the first year of engaging a client, there’s a lot of very logistical mathematical problems to solve. You we need this insurance policy, we need this account, we need this debt pay down, whatever. But after that, it always feels like it becomes a very, it’s just like a journey and it goes through emotions and it goes, it’s like a journey through values and evolving priorities. And it feels less like a math problem to solve and much more like a human condition to just navigate over years and years. was there a second one you were gonna say before? I had a question, but okay. Yeah, it’s fine. I ⁓ won’t remember anyway. It’s fine.

Carl Richards: No, sorry, I lost track of how many numbers I was using there. But yeah, but I think particularly like, A, the math side of finance is hard to understand because we use complex language. And B, there is a whole other side to finance that we’re not even prepared to talk about.

Ryan Isaac: Yeah. Yep. Okay. So, ⁓ if anyone had the privilege of hearing you speak at our summit this, this summer, this past summer in, in park city, you did talk a lot about that. think that’s where a lot of your writing and teaching, ⁓ is about. If you want to get into that a little bit as like a preface on, you know, the kind of concepts you’re trying to get people to understand. What I was going to ask is how does the average person, you know, highly educated and successful or otherwise. Navigate or even begin to recognize that emotion is very tight and it’s not just math, that there’s a programming, a history, a conditioning, probably like a lot of unseen or unacknowledged things that live in us from our parents and the way we saw parents deal with money or things like that. How do we begin to even navigate that as humans, this like money emotion thing?

Carl Richards: Yeah. Yeah, I mean, one play, I think it generally starts with just starting, like practicing being aware of it, right? Like, if you just start paying attention, like, let me give you some examples. I noticed a little while ago, maybe a year ago, I noticed… that I’d been going to the mailbox for 20 years. And most of the places we’ve lived for some reason or another, the mail got delivered at a central box. So was always a 100-yard walk. So I’ve been walking to the mailbox and I’ve been doing this for years. I just noticed that I was doing it probably last year. The process of walking to the mailbox, was always a little tense or gripped or…

Ryan Isaac: Yeah. Yep.

Carl Richards: Locked up a bit. I was like, what? And then I remember opening, I was trying to pay attention, like, why is that? And then I remember opening the mailbox and there was a letter from, there was an envelope from the IRS and I felt just, I could feel the tension in my body. Now I’d been feeling this for 20 years. I just barely noticed it.

Ryan Isaac: Yeah, I became aware of it, yeah.

Carl Richards: Yeah. And so, I remember opening that particular letter and being like, you know, rip it. Normally, I wait till I get home to open the mail, but if it’s from the IRS or the State of Utah Tax Commission, I’m ripping it open. I have no reason for this, right? Like, I’ve never had a problem ⁓ and don’t anticipate having a problem. But for some reason, I sort of rip it open. And I remember this particular one that helped me sort of start to see this a bit. It was a change of address request. You know, so like it was was benign. And then then a couple of weeks later, same thing. It was Utah State Tax Commission and it was a refund that I had kind of forgotten about. So it was actually positive. ⁓ And even if it was a request for something, it’s not a problem. So I like paid it started paying attention to that. Let me end. Which what’s very interesting about that story is on Father’s Day, I went to breakfast with my dad.

Ryan Isaac: Gosh. The most benign, yeah.

Carl Richards: And I was telling him about that and he was like, what do mean you don’t know why? I was like, I don’t know why. He’s like, what? You don’t know the story? I’m like, what story? He’s like, you don’t know about what happened to me and the tax problem that I had. You know, what would that be now? Forty five years ago. And I was like, no, I didn’t know that. I was like, I remember something in the periphery of my memory, but I don’t. And he proceeded to tell me about this mistake he had made that ended up being a big problem that he barely avoided time in jail. ⁓ But I didn’t know that, right? And I would assume those two things are related. So I could tell you, let me tell you one more quick story. I had some clients who, they were in this big like multi-month long argument that every time sort of money came up, this argument happened. And so again, there’s another, there’s another like, like if you just start noticing a pattern that is not serving you. know, like every time I open the American Express bill, we fight. Every time we talk about money or we look at the budget, we fight, okay, well, if you notice a pattern, you could say to yourself, how do we interrupt that pattern? So they were having this multi-month ⁓ sort of argument every time money came up about getting another car. And he was really frustrated because his… He was, and he even called me and told me, he’s like, look, my wife doesn’t care about, you know, brand, she dresses great, but she doesn’t care about brand name clothes. And, and our house is nice, but she’s never been particularly worried about it being the nicest house. I don’t understand what this deal is with this new car. Like, I don’t understand it. And as we talked through it, you know, and over the, over the course of a couple of conversations, he finally just asked crazy idea. Next time it came up, he, you know, they were in the middle of this argument and he just, you know, I don’t get it. I don’t get it. Like, and he said the same thing, like clothes and house and I don’t get it. Why is this so important to you to have a new car? And she was like, I’m so sorry. If I said new, didn’t mean new. Let me, let me tell you when I was 12, I remember my dad always drove old cars.

Ryan Isaac: Yeah.

Carl Richards: And when I was 12, I remember pulling up in front of the middle school and getting out and the car wouldn’t start at all. The kids were getting out of the bus. So there was like all the kids there and it backfired and everybody looked. And I remember being ⁓ stuck out on an old country road, having to walk two miles and my dad being upset about it to walk two miles to the payphone. Like she went through this litany of memories and she was like, I didn’t say new, I said reliable. Right. And so I, Every time I tell that story, I can feel empathy coming into the room. he was like, ⁓ right? So, if you understand those stories about a spouse, a partner, a child, a friend, your conversations are different, right? And one way to start that is just simply, I mean, I’ve been playing the guy who writes about money and feelings in the newspaper for a very long time, and I had never asked my wife. So a little while ago on my podcast, 50 fires, I actually had her on and interviewed her and I asked her about her first experience memory of money. that was after 27 years of marriage. So that’s a good entry place. Next time you’re with a spouse, a friend, a partner, just say, you know, I was listening to this crazy podcast and made me think like, what’s your earliest memory of money? And then if you’re feeling brave, you can say, oh, tell me more about that. Or how did that feel? Or

Ryan Isaac: Jeez, yeah. Mmm.

Carl Richards: Here’s another one you could try it. This is graduate level, but you could say, hey, in junior high, because that’s where all the angst happens, right? In junior high, were you one of the rich kids or one of the poor kids? And when somebody tells you, we were solidly middle-class, here’s the key question. How did you know? Because if you get a story about how did you know, like, ⁓ I only had one pair of jeans. This is one that somebody told me. I only had one pair of jeans and they got grass stains on them.

Ryan Isaac: Hmm. Mm.

Carl Richards: And I had to wear them the next day because I forgot to wash them. And the girl that I really liked who we were starting to be like boyfriend, girlfriend in junior high was like, you only have one pair of jeans and didn’t talk to me again. Yeah, yeah. it’s again, I think the long way to answer your question is you just start paying attention to it. Like for all the like, and this isn’t necessarily a gender thing, but

Ryan Isaac: Yeah. Core trauma forever.

Carl Richards: I find that a lot of men relate to this idea of being hypervigilant and hyper aware and worried that tomorrow’s the day everything will go away. And of course I’ve had this conversation with women, but I’m just saying from my perspective, I noticed this hypervigilance, hyperawareness. And if you notice that, like that there’s a lion in every bush in your life, right, start paying attention to it. That’s it.

Ryan Isaac: Yeah. hmm. Yeah. I’m hearing a couple of invitations, obviously for a broader audience ⁓ in their conversations at home. This would most definitely apply in the dental practice with your partners and associates, ⁓ your team, which is a whole different dynamic inside of a business. But I’m also hearing, you know, an invitation for us as financial advisors to continue to

Carl Richards: Yeah. Yeah.

Ryan Isaac: To push and explore on those things, especially as client relationships go on for years. Why are things happening and to dig into that? ⁓ Would you have any advice for how someone, no matter if they work with us or have advisors elsewhere, how they might work to explore those things with their advisors? Could be their CPA, could be their financial advisor. Is there ⁓ maybe a tip when they go into meetings, when they think they’re talking about investment performance that quarter?

Carl Richards: Yeah.

Ryan Isaac: That they can dig deeper. there anything that would be helpful?

Carl Richards: Yeah, yeah, I like I was just actually thinking about investments ⁓ because it’s so often ⁓ where some of these emotions show up like if the portfolio is down, right, there was actually a great research study done years ago where they hooked people up to brain scanners, whatever those are called, and had people open their brokerage statements.

Ryan Isaac: Really? my gosh man, no way. Yeah does sound insane.

Carl Richards: Yeah, and which it just sounds like a crazy experiment, but they, when the, when your brokerage statement was down or red, you process that in the same part of your brain as you do moral danger. So sort of where I’m from, like a grizzly bear breaking through the window. If your portfolio was up or green, you process that in the same part of your brain as you do security or pleasure. So if you start to understand like, okay, I go into a meeting with my finance team, my financial advisor or my CPA or both, and my portfolio is down 25%, like that feeling that you’re having, it’s just interesting to pay attention to it, right? Like is the portfolio designed in a way that was based on your long-term goals and values?
is the portfolio designed in a way that the last thing you should do is sell. know that rationally, all the facts and figures will tell you that, but you’re still feeling that way. Well, welcome to the club because there’s a reason you feel that way. You process that in the same part as your brain. Like you’re gonna run out of resources. You’re not gonna have any more food. You’re gonna die. Like that’s what’s going on. Yeah, so you just, I think if you just start noticing that and then any conversation around

Ryan Isaac: Yeah. Mm-hmm. Yeah, yeah, yeah, yeah. So the hierarchy of needs. Yeah, you can’t eat, shelter, yeah.

Carl Richards: Know, life insurance, comes up a lot because in a life insurance conversation, I mean, if you think about what you’re doing.

Ryan Isaac: Every time I have this, think this exact day.

Carl Richards: Yeah, like a spouse, you’ve got, if you’re with a spouse or partner, you are literally putting a value on people’s lives. And often the value is different just for economic reasons, right? Because as far as I’m concerned, this whole purpose of life insurance is to replace an economic loss. Well, we’ve got to be careful and calculate economic losses and they’ll be different based on the earning of one person or the other. And so, what’s that feeling like? ⁓ The kids’ education, savings. You run into this all the time where somebody’s like, no, I want to save, I want to pay down debt. No, I want to invest in the, I want to start a new office for the dental practice. And what’s that about? And that can turn into an argument that, so anytime we have these competing values, pay down debt, invest for the future by opening a new office. Those are competing values. we can just start exercising the ability to ask what’s underneath it. Because both of you, pay down debt and open a new office are probably pointing the same thing, like financial security for my family. If we can get to that, now we can have a third way conversation. Like, oh, I get it. You want the…

Ryan Isaac: Yeah. Mm-hmm. Yeah.

Carl Richards: Be in a place where you feel secure, so do I. Right? So anyway, I think that’s one way you can do it with when you’re meeting with advisors or planners is just to get really clear. One way to think about it is what are you trying to solve for? Because that presenting problem or thing you’re trying to solve, there’s always something underneath it. And if we can get clear about what’s underneath it, we can have much better conversations.

Ryan Isaac: Security, Mm. Love it. I want to get to the new book that comes out today, published today, ships today. Is that the right word? Ships. The public has it. In the past, you’ve written, speaking on this subject a lot, or you’ve drawn, written and drawn and spoken, a lot about the effects and consequences of taking action, financial action, financial decisions under the influence of these emotions without being aware of them or why they’re happening, where they come from.

Carl Richards: Published today, yeah, published today.

Ryan Isaac: Do want to speak a little bit to the impact that ⁓ that can have our behavior, the impact our behavior, sometimes subconscious behavior has on our financial outcomes?

Carl Richards: Yeah, yeah, it’s It’s so, it’s, let’s just talk about this as it relates to a really common feeling around money, which is fear. And we could also use greed either way, but with often a lot of what we’re trying to do, save more, you know, risky investment behavior, like, like the, this is slightly stereotypical, but the dentist who wants to open a restaurant, ⁓

Ryan Isaac: Yeah. Yeah, sure.

Carl Richards: Dentists and doctors are famous for that idea of opening restaurants. ⁓ But why? Well, because it’s a chance to make a bit more. Why do you need to make more money? Probably there’s some feeling underneath of like, someday we just need more, right? Someday this will go away. And I think if we start to understand the big dilemmas you pointed to is when this is subconscious. I’m going to paraphrase the quote, and I can’t even remember if it was, I believe it was Freud, who said, until we make the subconscious conscious, it will direct our lives and we will call it fate. And so, I think if you can start to understand, particularly fear, like Wait, am I making this decision out of fear? This investment decision, this spending decision, this saving decision? If I’m making out of fear, then I probably do want to create a little space between the stimulus and the response, right? Like, I see something on the financial pornography network. Somebody’s yelling and screaming about how we should all get out. I feel a little scared. My first reaction is to go hit sell. Well, can I go on a walk first?

Ryan Isaac: Yeah. Right? Mm-hmm. Mm-hmm.

Carl Richards: Could I remind myself of how I was thinking when I was thinking, can I get out of the branches of the tree and get back to the trunk? And so, think to the degree that we can just slowly start to learn, because I don’t know if, I I just discovered this the other day, that there will never be enough money to pay for all your fears. And that’s another thing we could talk about is like,

Ryan Isaac: Yeah. Mm-hmm.Mm.

Carl Richards: Jobs we’ve given money that it can’t do. But if we can just at least be aware of what’s driving our decisions. Okay, so there’s a lot of this challenge. I had some early, one of my early emergency room doc clients was he lived in a nice walkable community in Salt Lake. These were houses that were 1800 square feet. We lived next door to him.

Ryan Isaac: Yeah.

Carl Richards: He was always telling me about how all his doctor friends were like, when are you going to buy your doctor house? Okay, so if I’m going to go buy a big house, it’s just helpful to get clear. It’s okay if you want to do it because your colleagues all have them. That’s okay. Like, just be clear about it. It’s okay if you want to do it because you feel like it’s important for the kids to all have a walk-in closet. That’s okay too, right? ⁓ but just be clear about what it is and why you’re doing it is how I would, the unconscious parts of the problem. Like it shows it’s, you know, in spending. Like how did I, I didn’t even, I just had the thought that I wanted that thing and Amazon delivered it. Like how did that even happen? Right? So like so much of our spending and our investment decisions is just on autopilot. And this isn’t about deprivation, by the way. It’s not about budgeting. It’s about

Ryan Isaac: Mm-hmm. Mm. And it’s there. I know, yeah.

Carl Richards: Just being aligned with our use

Ryan Isaac: Intentional.

Carl Richards: of capital with what actually matters. Right? So anyway, that’s how I would think about it.

Ryan Isaac: Let me piggyback on that. There is a very common theme that we talk about with our clients. It’s very common in the dental industry, I’m sure in other industries too. I don’t know if I would call it a phenomenon, but it’s a very common thing that let’s say dentists in mid-career, they’re hitting their stride, their peak, their time and effort, money, education’s paying off. They’re as profitable as they’ve ever been making as much money as they ever have. They’ve got Savings and cars and trips. They’ve just they’re hitting a pinnacle and and They could keep going like it’s it’s going really well systems are in place. There’s teams in place like things are running well And there’s a thing that happens Where it almost feels like boredom to me? ⁓ Is is like the emotion because we’ll see people in this really ideal spot that they’ve wanted to get to for 20 years Anyone would want to be in their shoes and it’s almost like it became too easy, too predictable, they start making financial decisions that could put all of that in jeopardy. ⁓ And I don’t know what it is, it feels like boredom, it feels like stagnation, it might feel like burnout, it’s very common. There’s probably nuance, we try to name it, but does that resonate? Have you seen that? Can you speak to that or name that? What’s happening, what’s going on?

Carl Richards: Mmm. Yeah. Yeah, Yeah, I mean, I don’t know, but I’ve noticed the same thing. I’ve had hundreds and maybe thousands of conversations about it. I think what happens in somebody’s… This happens in the entrepreneurship world as well and certainly in physicians, but there’s a unique version of it where early in your career, you don’t have any extra capital, right? Like not time, money, energy, and attention. So, four sources of capital, you’re pouring all of that back into the career.

Ryan Isaac: Okay. No, yeah.

Carl Richards: And then you wake up one day and you have a little bit of space, right? In the form of excess margin, right? Like you have a little bit of margin of safety. There’s money that’s built up. We aren’t very good at, at that point, you’re so used to always reinvesting and always being on edge. We’re not very good. It’s interesting to think about, like, I’ve had this conversation so many times, like, are you comfortable with

Ryan Isaac: Yeah. Yeah.

Carl Richards: A pool of money just sitting there. What is it about the need to go do something? And I’m talking beyond a normal investment process, right? Like I gotta go do something more. Like I gotta buy some real estate. I gotta flip a house. And so when you start to feel that feeling, I think the question to ask again is, what am I solving for? Because if I’m solving for rate of return,

Ryan Isaac: ⁓ Yeah ⁓ Mm. Mm.

Carl Richards: That’s a reasonable thing to say. just want to, I want to be, because this will show up in all sorts of sneaky ways and language will show up like this. I want to be a wise steward of my money. Right? And I want to build for the financial future. Well, if we look at the data, taking the level of risk that we often see is not going to be helpful. That’s not being a wise steward. It might be because you’re bored. It might be because your buddies are doing it.

Ryan Isaac: Sure.

Carl Richards: It might be because you want to compete. It might be because, but if it’s because you’re bored or any of those things, I think you just say, what am I solving for? Cause if what you’re solving for is, you know, I’m a little bored. Well, there’s different ways of solving that problem. Like I often talk about like get really clear about where you’re getting your kicks from. Because if you start mixing, investing in entertainment, it’s fine. But, but it, there’s cheaper ways of getting entertainment.

Ryan Isaac: you Yes. Yes, I love that. That’s such a good one. Yeah.

Carl Richards: And so like that was the very first column I ever wrote for the Times actually was a Venn diagram that said one circle said entertainment and the other circle said investing and the overlap was labeled a bad idea. ⁓ Because it turns out like the best way to get a great rate of return is to do almost nothing over a long period of time. But like how about this? I just want to drive this point home because I know some of you who are listening are kind of like me, which is like that can’t be true. OK, Buffett.

Ryan Isaac: Mm. Yeah, long period of time, yeah. Yay.

Carl Richards: Buffett’s my favorite quote of all time, and there’s a lot of good Buffett quotes, but this is my favorite of all time. The hallmark of, and okay, just to set, like this is arguably the greatest investor to ever live. The hallmark of our investment process is benign neglect bordering on sloths.

Ryan Isaac: The hallmark of our investment process.

Carl Richards: Right, benign neglect, boring on self. And it’s like, this is language I use with myself, not with your audience. what I say to myself when I think I know that I can go out and do something that’s gonna be exciting and fun and make me a ton of money, I often, I’m trying to rewire that and just say like cute story, right? Like cute story that you think, to me, I would never say that to your audience, but like cute story, like.

Ryan Isaac: You know. Yeah. He’s ju- Totally. Yeah. Yeah. Yeah.

Carl Richards: Why not just be proud of the fact that I’m doing what the smartest people say you should do, which is have a broadly diversified portfolio that’s low cost and then leave it alone for a long, time so it can compound. And then, okay, now I’ve got this problem on board. Okay, cool. We can totally solve the boredom problem. Right? Like have you been paragliding at point of the mountain? Do you know how to ride a mountain bike? Yeah, there’s a lot of like a sprinter van can help you take a little bit of ⁓ boredom out of your life. So anyway.

Ryan Isaac: Yeah. Mm-hmm. Mm-hmm. Yes, yeah. I was just gonna say there’s a lot of ways to take some risk. Oh, I love that. No, I think there’s probably a lot of thing and thank you that it really touches on I think what happens and there’s probably some other factors like, you know, an entrepreneur or a person who’s been grinding for 20 years out of school and debt and, you know, building a company that we probably get used to how hard things are that one things don’t feel as hard anymore. We need them to feel hard to feel worth it. Yeah, something’s wrong. So it’s not hard anymore. It’s kind of like, um,

Carl Richards: Yeah. Something feels wrong.

Ryan Isaac: When you meet, when you have like a runner friend who casually runs like an easy 20, you know, every morning just to, and you just get so, we just adapt so well. So, you know, we just adapt to our circumstances and then continue to look for ways to feel pain or comfort. Maybe pain is comfort sometimes.

Carl Richards: Yeah, yeah, yeah. No, and I think, but yeah, think there is, it’s very easy and very easy to trick, get tricked or trick yourself into the idea that ⁓ if something is simple and easy, it must not be working. And it needs to be more complex. And then on the other side, I think a lot about the, you know, and I… I remember writing a bit about this early on, this sort of doctors, I don’t know if dentists refer to it the same way, but medical professionals that I had conversations with often used to refer to this as the cage lion effect, that right out of residency, suddenly making first chunk of money, just go on a spending spree because they’ve been eating ramen forever. But I think this idea of when you finally get to the place where there’s a little bit of excess,

Ryan Isaac: For sure, yeah, it happens.

Carl Richards: we need to get better at being okay, right? Like being okay with a little bit of slack in the system. Because if not, you’re going to be a broken human. And we know all those stats from the dental profession, right? And so I think just being like, wait, what if I just took the foot off the gas just a teeny bit so that I can keep… By the way, what we’re most interested in is your lifetime, meeting your lifetime goals.
not your first 45 years of lifetime goals, but your lifetime goals, which will probably be, you know, 85, 90. And if in order to do that, we got to have a little rest and recovery in the system or else you’re just going to end up a broken human. And we, again, it’s cute to think that you’re immune to that when all the stats show that high driven professionals fall prey to this all the time.

Ryan Isaac: Yeah, I appreciate that man. It’s an ongoing discussion we have with clients among our team all the time. Let’s get to your book. What’s the title of the book that’s just today’s the date? It’s October 21st, 2025. Tell us about the book. How did you’ve done a few books before this? I mean, how long you’ve been writing for?

Carl Richards: Yeah. Well, yeah, mean, 20 plus years. let me, know, Ryan, just thought of one thing I just want to mention about that last topic. ⁓

Ryan Isaac: Do remember? 20 plus years? Yeah.
Okay, yeah, yeah. Okay.

Carl Richards: There’s this tendency to think that we’ll be the ones to prove the Buffett quote wrong. And that’s a beautiful thing that leads to success and winning mountain bike races and this desire to be sort far above average.

Ryan Isaac: Mm-hmm. Yeah, we like to think we’re the exception. Mm-hmm. Yeah.

Carl Richards: And I think it’s just important to understand, I almost feel like you have a fancy feelings budget. you can’t be far above average in everything you do. And investing’s a completely different animal anyway. being far, there’s some structural reasons why taking par. Like if you got to play against Tiger Woods and you could choose to take par, almost everybody would just take par. You know what I mean? Like, so.

Ryan Isaac: Yeah, or like or try to beat him.

Carl Richards: Yeah, yeah, what did you prefer? Do you wanna try to beat him or do you wanna take par? Yeah, yeah. So,

Ryan Isaac: Guaranteed par. Yeah. Yeah. Oh, yeah

Carl Richards: But here’s the other thing that’s really interesting. Almost like nearing or in retirement. dental or medical professional that I’ve talked to would gladly trade just having their money back for the broad experience of their investment experience. Like if I could just have not lost money on that spec home and if I just wouldn’t have started that car wash and I just wouldn’t have done that, like if I just had been boring, right, and built a portfolio and stuck with it.

Ryan Isaac: Yeah. Yeah. Yeah.

Carl Richards: And my business, by the way, like, so like that’s a, that’s a lot. Like you’re to run a super successful business, right? And you’re going to try and do the thing over there. Like you’re much better off taking all of that energy, super successful business and rest so that you can be your, your value. I actually wrote a paper on this once. Your, most important asset is the present value of your future earnings. In other words, you.

Ryan Isaac: Yeah. OK, yes.Yeah.

Carl Richards: Your ability to continue to earn is your most valuable asset. And the longer, if you can add five years to that of healthy, happy earning, that’s the best thing you could ever do. Like that’s worth more than any car wash would be or a restaurant success. So I think the idea of like barbell structuring your risk, like I’m going to take a bunch of risk in my practice. I’m going to build that. I’m going to rest a lot. I’m going to make sure I can do this for a long period of time and still be a great mother and spouse, right? And over there, I’m gonna be boring. I’m gonna throw that money over the wall and just let it be boring and I’m gonna not mess with it. That’s the most successful I’ve seen after thousands and thousands of these conversations.

Ryan Isaac: So good, I love that you just brought that up because often again, adaptation. I think when a dentist specifically has been in a successful business for 10, 15 plus years and it’s running well, there’s systems, there’s people, there’s teams, they forget that that was actually a gigantic risk. It is a private business, small business, the most risky asset I think out of all the asset classes. And Sometimes they’re like, you know, I want to chase private equity. I’m like, well, you’ve owned private equity for 15 years. It’s 60 % of your balance sheet. There’s 25 people on payroll. You know, there’s, there’s all you’ve already taken massive amounts of risk in your investments by running, starting and running a business and you’ve, you’ve done it successfully. And now it is you as the asset, it’s paying you like this. I, and I love what you said to this relates to burnout, which we talk about with our audience a ton as well as

Carl Richards: You are private equity.

Ryan Isaac: I would rather see a client build a life in a way that allows them to work for a long period of time. They don’t have to do it five, six days a week like they do out of residency. you know, the asset of ⁓ like a potential income, of earned income of some kind is just massive. It takes so much pressure off a portfolio, even if it’s, you’ve got, dentists can earn a hundred grand a year on very few hours a week, laid into their life and still maintain a lot of sanity and free time and that kind of.

Carl Richards: Yeah, yeah, yeah.

Ryan Isaac: pressure valve release on a portfolio in any amount is just huge. I’m really glad you brought that up,

Carl Richards: For sure. Well, and keep in mind that all of this misses the plot anyway, which is like, it’s not about making more money. It’s about having a meaningful life. And so if you sort of throw that in there too of like, what if I didn’t get caught up in all this stuff? What if I, what? mean, this would be crazy. What if I didn’t buy the house? What if I decided that the…

Ryan Isaac: Mm. Mm-hmm. Yeah.

Carl Richards: you know, the wake surfing boat, why? Because I want to spend time together. Okay, I can do that and that’s a good way to spend time together. But there’s other ways, like we could go on a bike ride, we could start a garden in the backyard. So it’s just fun to start thinking about like, what is my dream? Not the dream I saw on Instagram and not the dream that my partner has at the office, but what’s mine? and you see those occasionally, they almost feel countercultural, right? The dentist that’s driving an old car because he’s like, it’s good enough. He’s like, what? Are you allowed to do that? You’re making the rest of us uncomfortable. You know, but and again, if your cars are important to you, that’s totally fine. But I’ve got a buddy who makes crazy money. He was a valet in Los Angeles when he was young.

Ryan Isaac: Yeah. I love seeing that. I love when I see that. Yeah.

Carl Richards: And so he feels like he should be a car guy and everybody tells him he should be a car guy. And he’s like, I have enough money that if I want to be a car guy, I could be a car guy. He’s like, but I every couple of years I forget that that’s other people’s dreams. And so I decide to run a little experiment. I travel a lot for work. He says he goes to the Hertz counter once every couple of years and is like, you know what? It’s costing an extra 200 bucks for the day. Give me the Porsche. And he said he doesn’t even have to get off the lot.

Ryan Isaac: Hmm Yeah, yeah.

Carl Richards: Before he’s like, dude, I can appreciate it. This is an amazing piece, but it’s just not for me. But it costs him $200 every couple of years to figure that out instead of a $150,000 mistake. And so I just think it’s interesting to just start running the, what are you doing this for in the first place? Who cares about your, what are you doing this in the first place? Like sailboat, $5 million in a sailboat. Have you ever been on a sailboat? Like go do that for a day.

Ryan Isaac: Yeah. Yeah, it’s not my thing. Mm-hmm. Yeah. Mmm. I love that, Yeah.

Carl Richards: And I look, I’m ranting a bit, but I have deep empathy for this because Instagram makes it so hard, just Instagram is a metaphor. Instagram makes it so hard to get clear about what we want. Like, what do we actually want? Because that’s what we actually care. We don’t actually care about. Nobody’s going to die being proud of their portfolio return. Right? Like what we actually care about is your ability to live a meaningful life of connection with your family and the people you love and maybe your community. We know for sure that that’s what you will value late into your life. The things you’ll remember will not be related to more work or more money. They’ll be related to the impact you made, experiences you had with people you loved, and the difference you made in your community. It’s settled doctrine. We all know it. So it’s just like, okay, why do we get off track? Well, just practice. Be gentle with yourself. Sometimes, you know, like a

Ryan Isaac: man… Yeah.

Carl Richards: Sometimes a cold bucket of water in the face is fine too, but, but, but let’s just practice asking better questions about what this is all for in the first place.

Ryan Isaac: Yeah Man, I love it. feels like ⁓ it’s rare and it feels like a huge gift when you can get to the place in life that when you know all the things that are no’s for you, even though society, friends, culture might be saying you should do this, you should be this. It feels like a gift when you can get to that place and you’re like all those things are no, these are my few hell yeses. And ⁓ that’s what life is built around. Everything else is answer there. It feels like a huge gift, man. ⁓ Wrap it up, tell me about the book that’s coming out. ⁓

Carl Richards: Yeah, for sure.

Ryan Isaac: culmination of so many years of writing and ⁓ Yeah, ⁓ the title yeah

Carl Richards: Yeah. Yeah, mean, people have asked me, yeah, how long have you been working
on it? And the answer is 27 years. ⁓ But this is the first book since my last book was 11 years ago. And I have said no almost every month since then. Like from publisher or agent, I’ve just been like, no, no, no, no, no, no, I’m not writing another book. What I started noticing, though, was this need for…

Ryan Isaac: Yeah. Yeah. really? ⁓

Carl Richards: I’ve actually referred to the book as a conversation grenade, right? Like you toss it in a room and conversations break out. So I just wanted to create a tool to just spark these kind of the kind of conversations we just had. Right. And so there’s a hundred. It’s called Your Money Reimagining Wealth Through Simple Sketches, Through 101 Simple Sketches. It’s 101 of the sketches. It’s laid out like a I spent. We talked about fancy feelings earlier. I spent my entire fancy feelings budget on that.

Ryan Isaac: Cool.

Carl Richards: On the form factor of it. So it’s seven by seven. It’s soft cover. So they want to do hardback. I was like, no, I want it to be more. I don’t want it to be so pretentious. I want it to be this beautiful matte finish soft cover. There’s 101 sketches with 101 essays. Some of them are two sentences, but none of them would take you more than three minutes to read. And it’s just meant to be tossed. Leave it on the coffee table, right? Like hand it to a friend.

Ryan Isaac: Okay. Yeah, I love it. No. Uh-huh. Yeah.

Carl Richards: And see what sort of conversations break out. That’s the goal of the book.

Ryan Isaac: I love it, I’m looking at it on, can I order this? I’m seeing it on Amazon right now. That’s it. This is not a book, period. It’s a conversation grenade. I love it. It looks really good, man. Well, congratulations ⁓ on what, like what was your why? Why were you saying, it sounds like you were saying no to another book ever. How did that change for you?

Carl Richards: Today is the day that it will actually ship, yeah. Yeah. Thank you. Yeah, I here’s the story. kept getting, we’ve been getting these emails for a long time where people are like, hey, I took your sketch, I printed it out and I pinned it to the bulletin board at the office and, or I taped it to the fridge at home. And none of these emails said it’s so visually striking. None of them said this is amazing art. What they all, what they all said was I can’t believe the conversations it starts. And so,

Ryan Isaac: Okay, yeah. You sure? Interesting.

Carl Richards: This has been going on. I’ve been thinking about the sketches as a conversation grenade for a long time. I finally was like, had 11 years ago, I swore off writing any more books. And I largely wasn’t, I was like, I love conversations. And so I was like, wow, this is so fascinating. I live in a world where I can actually, I can actually build a media business around conversations. It’s called podcasting. And so I was like, this is amazing. And then, so I’ve been focused on that for the last decade. And then I realized like the

Ryan Isaac: Yeah, uh-huh, yeah. Yeah, same. Yeah, it’s great.

Carl Richards: What if I just had something that was actually kind of like a forcing function to help force me and others to have more conversations? And that’s why, my why is to start a million conversations about money. Yeah.

Ryan Isaac: Hmm. Awesome man. Your
money, reimagining wealth in 101 simple sketches. I love the format. Seven by seven you said? It looks cool. Yeah, looks good. Go pick it up. We’ll have links everywhere. So, man, thanks for spending some time here. ⁓ I think this conversation will be super valuable for our listeners and our audience. Anything you want, any parting things you want to leave us with, ⁓ anything else that hasn’t been said yet.

Carl Richards: Yeah, yeah, it’s very fun. Well, only because I know a bit about your audience having met some of the people at the… Do we call it a summit? Yeah. Yeah, and I just like… You’re in such a cool position to be able to start asking somebody… It’s not easy. Your position doesn’t make it easy, but it just might make it possible to start asking some of these questions about what’s it about, right? Like, what’s it for and…

Ryan Isaac: Yep, the summit. Yeah, yeah, Dentist Money Summit.

Carl Richards: And by the way, none of this is soft. Like you better believe you’re making smart portfolio decisions. And we want to be serious about how we’re spending and saving. And there’s a whole section of the book on spending all of this stuff. But what the real hard work, the scary work, the you want to take some risk, sit quietly in a room and try and figure out why you’re doing this. Right. You’ve all we’ve all conquered out there.

Ryan Isaac: Mm-hmm. ⁓ yeah. Yeah. Mm-hmm.

Carl Richards: We’re scared to death to go in here.

Ryan Isaac: Yeah.

Carl Richards: And in here means for some of us, like in our own homes with our own kids, with our own spouses. Like I would just like the more, this is the last metaphor for this, like just imagine being in an endless argument. And this is what the financial services industry is. The financial pornography network, otherwise known as CNBC, is just a never ending argument.
about whether to take a plane, a train, or an automobile on a trip. And then once you decide, like a which car, but the problem is you’ve got to decide where you’re going first. And why would you, like let’s just spend a little bit more time thinking about where we’re headed, where we’re headed. Because then the decision about what plane to take, like what car, what form of transportation becomes much easier if I have a sense. Otherwise I…

Ryan Isaac: Yeah, yeah.

Carl Richards: And I would imagine your listeners relate to this except the ones that are clients of yours, that otherwise it feels like a constant gerbil wheel of like, what about that? And what about that? And what about that? Crypto now, how about Bitcoin? If we get clear about what were the reason we’re doing it, we can get ourselves off of that madness, right? Turn the financial pornography network off for good. Okay, cheers Ryan.

Ryan Isaac: All the time, yeah. Yep. Yeah. Yeah. Mm-hmm. Yeah, thank you. Man, there’s so much good stuff here. Cheers to you. Thank you so much, man. We’ll see you around. Thanks everyone for tuning in. Catch you next time. Bye, everybody.

Keywords: financial conversations, money emotions, financial advisors, emotional intelligence, financial decisions, wealth management, dentist finance, Carl Richards, financial literacy, personal finance.

Behavioral Finance, Finance 101