Your Money Problems Aren’t Math Problems (They’re People Problems) SB1751

Here’s the secret nobody tells you: your money problems probably aren’t math problems.

Joe Saul-Sehy and OG sit down with Carl Richards—financial planner, New York Times columnist, and the guy behind those brilliant “Sketch Guy” drawings that make money actually make sense. Carl’s spent his career helping people untangle their relationship with money, and his big insight? Most of us are overthinking it.

Your financial plan shouldn’t feel like a calculus final. It should feel like a map you can actually follow. Carl breaks down why emotions (not spreadsheets) drive most money mistakes, how to cut through the noise that keeps you paralyzed, and why the simplest plan is usually the one you’ll actually stick to. If you’ve ever felt like you’re “doing it wrong” because your strategy doesn’t involve leveraged ETFs or cryptocurrency mining, this conversation will be a relief.

Then Joe and OG dive into the options trading debate. Is it a legitimate tool for managing concentrated stock risk, or just financial cosplay for people who watch too much CNBC? They break down when options might make sense, when they’re just expensive complexity, and how everyday investors should think about them (if at all).

Plus: travel stories, Neighbor Doug’s trivia (where he definitely brags about something), and proof that you can get smarter about money without wanting to take a nap.

What You’ll Walk Away With:

• Carl Richards’ framework for simplifying your financial life—and why “The Behavior Gap” matters more than your rate of return
• Why the emotions behind your money decisions matter more than the math (and how to work with them, not against them)
• How to filter out financial noise and focus on the handful of things that actually move the needle
• The truth about options trading: when it’s a smart risk management tool and when it’s just expensive gambling
• Permission to keep your plan simple—even if it feels like everyone else is doing something fancier

This Episode Is For You If:

• You feel like everyone else has figured out money except you
• Financial jargon makes you want to hide under a blanket
• You’ve got a solid income but still feel anxious about your money decisions
• You’d rather learn through real stories than get lectured by a guy in a suit
• You want to finally understand why you make the money choices you do (good and bad)

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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Our Headline

• Advisors weigh in on the benefits of options as a hedge against concentrated stock risk (InvestmentNews)

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Doug’s Trivia

• What is the name you and I know the Haloid company as today?

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• Check out The 201, our email that comes with every Monday and Wednesday episode, PLUS a list of more than 19 of the top money lessons Joe’s learned over his own life about money. From credit to cash reserves, and insurance to investing, we’ll tackle all of these. Head to StackingBenjamins.com/the201 to sign up (it’s free and we will never give away your email to others).

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Join Us Friday!

Tune in on Friday when we’re asking our panel of financial enthusiasts about “Reverse FIRE”

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Written by: Kevin Bailey

Miss our last show? Listen here: Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750

Episode transcript

[00:00:00] OG: All right, here we go. Hold your ears folks. It’s showtime.

[00:00:12] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show.

[00:00:26] Doug: I’m Joe’s Momster neighbor Duggan. Today we simplify, saving, investing and financial planning with a legend in the space, New York Times columnist and financial planner. Carl Richards joins us for a wide ranging discussion about how to manage your money, goals, and life in a simple and effective way. In our headline segment, advisors are wondering about options.

[00:00:49] Doug: How exactly do options work should you add them to your strategy? We’ll chime in and you know it. I’m also gonna swoop in halfway through the show with my mind bending trivia that you can totally show off to all your friends or both of them like me. And now two guys who are the best friends your money could have.

[00:01:09] Doug: It’s Joe and oh g.

[00:01:17] Joe: That’s right. Welcome to your Money Mentors show. I am Joe Sulci. Hi. I’m so happy that you’re here. It’s another Wednesday and that means, oh geez, on the money. How are you buddy? I 

[00:01:30] OG: am, 

[00:01:30] Joe: uh, 

[00:01:31] OG: live 

[00:01:32] Joe: in 

[00:01:32] OG: living color. 

[00:01:33] Joe: It is a fantastic day here in Texas. We got beautiful blue skies, late fall, or as we call it, summer.

[00:01:41] Joe: I am about to head out for, uh, the beauty of West Virginia, and I think we might’ve missed the peak of fall color there, but I can’t wait to, it’s a little 

[00:01:49] OG: bit, I mean, it’s close. I bet you’re close. 

[00:01:52] Joe: New River Gorge Dollywood. We’re gonna go to Dollywood, obviously gonna go visit a coal mine. We’ll actually go see some of the old coal mines in the national park.

[00:02:02] OG: Yeah, you drive around, you see ’em. 

[00:02:03] Joe: Looking forward to all of that. 

[00:02:04] OG: But today, cool state, not a cool border. You go, really? That’s the design. That’s what the map guy decided. That’s 

[00:02:12] Joe: it. The squiggly lined. Like he was drunk when he made West Virginia. Like Oh. Like a little 

[00:02:17] OG: point at the very top. Like what’s the point thing for, 

[00:02:19] Joe: well, his hand Snee got all sneeze.

[00:02:21] Joe: Could 

[00:02:21] OG: you? 

[00:02:22] Joe: Oh, sorry, Marilyn. We had to, my bad. Had to take part of that. We get a great show today. You know why? Because the guest talking upstairs. Uh oh. Gee. You walk right by him. I don’t even know if you recognize him. Carl Richards is here. Oh. Right. Carl Richards, Mr. Behavior Gap. The guy that that 

[00:02:39] OG: Oh, was a guy that was drawing all that stuff.

[00:02:41] Joe: That’s right. Yeah. For many, many years. 

[00:02:43] OG: That’s why I didn’t notice him. I thought he was a, I thought he, I thought we commissioned him on a project. 

[00:02:49] Joe: We, for so many years, all got to have the fun of, you’d open up the New York Times and there was Carl Richards the sketch guy. Mm-hmm. And once a week he had a column in the New York Times.

[00:02:59] Joe: But here he’s with us. We went all tactical on Monday when Anna was here. If you didn’t have a chance to listen to that, we answered a bunch of great stacker questions. Well, today we’re gonna get much more philosophical with Carl. ’cause that’s Carl. Carl talks about, you know what, there’s all this math og all this math.

[00:03:18] Joe: And yet it’s not the math that It’s not. The math usually trips us up. Math. It’s not the 

[00:03:22] shout otu: math. 

[00:03:22] Joe: How far into your career were you when you realized that becoming like a psychologist, a money psychologist, was a big part of your role? I was today years old. 

[00:03:35] OG: Um, I, I can’t answer that. I mean, a lot of people would look at the timeframe when I started this work late nineties and say, oh my gosh, what a terrible time.

[00:03:49] OG: You know, you got the peak of the bull market in the late nineties and then just immediately into the crash kicked in for the next 11 years. And I think that because of that, we learned so much about expectations and communication and staying the course and all those things during that 10, 11 year period at the beginning of my career that anytime the market’s down now, you know, it’s like 20 people, like 20% child play, big deal, you know, been there.

[00:04:18] OG: Uh, but um, and I actually am kind of worried about the investor of today that has not seen anything but 15, basically, 15, 17 years of the market going straight up. And you know, there’s been the occasional blip and obviously COVID and that sort of deal, but I don’t think the average investor right now is equipped with the memory of how sometimes it goes for an extended period of time.

[00:04:43] OG: And so you gotta be ready for that. 

[00:04:45] Joe: Well, I worry about for the same reason I worry about the young advisor. 

[00:04:49] OG: Yeah. Who has a busy advisor or investor. Absolutely. 

[00:04:52] Joe: Yeah. You’re trying to help other people control their emotion. It truly is all about controlling your emotions. What I love about Carl Richards is his ability to take these math problems and talk about what truly is the jumble of emotions we have around money and dissect them and really take these complex arguments and these complex things and go, you know what?

[00:05:14] Joe: It’s not as complex as we make it. Which is why he was able to very simply put things into sketch form for so many years. So today we’re diving in with Carl Richards on what promises to be. I can assure you a wide ranging discussion about your money, about your emotions, about your relationships, and man, get ready to take some notes.

[00:05:35] Joe: But before Carl comes down to the basement, we got a couple sponsors to make sure we can keep on keeping on. You don’t pay any money for any of this. Goodness. So we’re gonna hear from them. And then Carl Richards coming down to Mom’s Basement.

[00:05:56] Joe: And I am so happy we have this gentleman back in mom’s basement. We gotta get him like a frequent visitor card. Carl Richards. That has been a while, Carl. 

[00:06:06] Carl: It. Ha I would not even like to figure out how long it’s been because I’m always, I’m like, it’s been a decade, it feels like yesterday. I know, 

[00:06:14] Joe: I know.

[00:06:14] Joe: And yet, when I said hello to you, just while we were upstairs talking to mom, it was like three days have passed since we talked. I always feel like three days have passed since we spoke last. 

[00:06:24] Carl: It’s exactly right. I, I have this unrealistic expectation that everybody’s my best friend and it gets me in trouble a lot, but it often serves me really well.

[00:06:33] Carl: So it’s, that’s good. I’m, I felt the same way. 

[00:06:35] Joe: I do like the idea though, and this is a whole different podcast of beginning with people are inherently good versus people are inherently bad. Like just going in and thinking they’re gonna be my buddy. 

[00:06:46] Carl: Yeah, for sure. I, I guess I don’t care whether it’s true or not in the inherent question.

[00:06:52] Carl: I, I, I have an opinion, but I don’t even care. I would much rather live as if it was true. People are inherently good. 

[00:06:58] Joe: A hundred percent. 

[00:06:59] Carl: Yeah. 

[00:07:00] Joe: You write, as I think all of our stackers know about the intersection of behavior and finance. Finance at its heart is a math problem. And yet we try to fix these problems with calculators.

[00:07:16] Joe: And you’ve been doing this for a long time. I’ve been doing this for a long time. Why do we keep trying to solve these emotional issues with calculators, Carl? 

[00:07:26] Carl: Yeah. It’s funny, Joe. I mean, I have a very big calculator and I know how to use it. 

[00:07:30] Joe: You don’t wanna brag, but 

[00:07:31] Carl: no, I, I’m, I’m bragging. I have the biggest calculator and I know how to use it.

[00:07:35] Carl: And yet, you know, this took me a decade or so. I mean, I’m 25 years into this and it, for the first decade, I thought that calculator would solve everything. And here, here’s the dilemma. I kept running into, if money is a math problem, how come I end up in a fight? Right? Like two plus two always equals four.

[00:07:55] Carl: Two plus two never equals envy. And how come I’d end up in a fight with a spouse, a partner, a child, a friend over money if it’s a math problem. And it, it turns out that indeed it probably should be a math problem. Like in the end, like maybe in our most enlightened relationship with money, money is purely neutral and it’s a tool ’cause it is like it’s a zero and one in a cloud.

[00:08:18] Carl: But between here and enlightenment, it turns out money is just a series of stories. And so I think the reason we keep getting hung up by this is money and money conversations end up being like an electric fence that you didn’t expect or didn’t know was electric. You thought it was just a fence and then you touch it and suddenly there’s all this energy and hello.

[00:08:42] Carl: Yeah. That energy comes from the stories we’ve layered on top of it. 

[00:08:46] Joe: Well, and it’s interesting because when you talk about the stories, you know, you also like to point out that two of us can look at the same story. We can look at the same. It is funny. I have this uh, friend who taught me that a negotiation’s like a cube or discussions like a cube.

[00:09:01] Joe: I’m looking at a cube. You’re looking at a cube, but you’re looking at one side of the cube. I’m looking at the other side of the cube. I feel like Carl money’s also a cube. How can we have the same thing? And you look at it completely differently than I do. 

[00:09:12] Carl: Yeah, it’s astonishing. I remember coming home one day from a tough day of work in the coal mines.

[00:09:17] Carl: I was feeling that way, sort of like beast of burden. And I walked in, I’m sure I was using this voice and making this face and I was like, oh, it’s so hard. And I’m sure I groaned a few times and my wife was like, I mean there was a little bit of like get over yourself in her voice, which I appreciate. But there was also this, like, she said this crazy thing and it was astonishing to me and I love this language around like, this thought had never crossed my mind.

[00:09:46] Carl: ’cause I was like, making money is so hard, it’s so tough. And she was like, Hey, what if it was fun and easy? And I remember, this is a a hundred percent metaphor, but I remember wanting like, actually, I won’t even use the metaphor, but I just remember being angry. Sort of like, what? What do you mean? Because that thought had never crossed my mind and she was viewing it from a completely different perspective.

[00:10:09] Carl: At least in that moment. She was viewing it from a completely different perspective. She was thinking something that had never even occurred to me. Not only do I not know how to think that way, I didn’t even know you were allowed to think that way. That to me is such an important piece. That’s why travel is important.

[00:10:27] Carl: It’s why conversations, we were talking about regional differences. It’s while hearing from people who are different from you, who bring different perspectives, different traditions, like some of the stories, I mean, I’ve traveled all over the world. We lived in New Zealand for four years, in London for a year, and some of the stories you hear from people about their relationship with money, you’re suddenly like, whoa, there’s a different way of thinking about this.

[00:10:52] Carl: I think that’s how it all happens. I mean, we get into the science of standing at a, at the corner and seeing a car accident. You’re standing shoulder to shoulder with somebody and you have police reports taken, and the police reports. You’re just like, I don’t even know what that guy was watching. I mean, you could go to a movie with your spouse, come out of the movie, see your best friends.

[00:11:14] Carl: You, you hear your spouse describe the movie and you’re like, you were in a different movie. 

[00:11:18] Joe: You see this right now online with politics. 

[00:11:21] Carl: Oh, don’t even, yeah, we can’t, 

[00:11:22] Joe: you know what I mean? No, we won’t pitch. I know, but it’s a hundred percent what you see, you and another person looking at the same exact thing and you’re like, what the hell are you looking at?

[00:11:30] Joe: Are you kidding me? No, 

[00:11:31] Carl: it, it’s clear that I think politics is a really good lens for this because there are people in my life that I have conversations with that I, it’s become very apparent they live in a different world and like, I’m not saying that metaphorically, they actually live in a different reality than me.

[00:11:52] Carl: I’m not saying it’s bad or good in any way. I’m just saying we both live in different realities because of the stories and mainly the lens through which we’re viewing the world. And that absolutely applies to money. I mean, scarcity and abundance, hard, easy, like we go through the whole list. Fear or greed.

[00:12:13] Carl: There’s a whole list of lenses through which we’re viewing the world that mean that, I mean, I think you and I live in closer realities, but they’re definitely different. 

[00:12:21] Joe: I love how we open this conversation with strategic talk, right? This high level stuff of money is, emotion calculators are good, but if it was just a calculator problem, then we’d all be on the same page and yet we can look at things from these, these different aspects.

[00:12:38] Joe: I wanna get a little tactical for a second. Like how do we start to bridge these gaps with people? Like what’s the point here? Because what I heard was probably travel more. Talk to more people. Is it be open more about having these money conversations. Yeah. What’s the tactic? 

[00:12:52] Carl: Yeah, let’s get like super tactical on a very, like, like a close level.

[00:12:57] Carl: I, I love the idea of starting. There’s a great David White poem called Start Close In, like start close in. ’cause it’s fun to think about, you know, the things we’ve already mentioned, travel, but what’s even closer and what’s even closer is the person you’re sitting next to at dinner or a client or a colleague, or a child or a friend.

[00:13:19] Carl: What if we just started learning to talk about money in a layered, in nuanced way? Let’s use Stephen Covey’s statement about like the last thing you’d want to do. I’m paraphrasing. The last thing you’d wanna do is spend your whole life climbing a ladder only to find out it’s leaning against the wrong wall.

[00:13:40] Carl: And we spend a lot of time talking about ladders and walls. Like which investment, which budgeting app, which credit card. Those conversations are useful and good, but not if they’re leaning against the wrong wall. Not if we haven’t had a co and like one more terrible analogy, like if we’re gonna go on a trip.

[00:14:01] Carl: The way we approach personal finance right now feels to me like an endless debate. And again, valuable, an endless debate about whether to take a plane, a train, or an automobile on a trip. If we’ve decided to take a car, which car? What type of car? What’s the gas mileage? But what I’m saying is, could we have some conversation about where we’re going, or at least in conjunction with what form of transportation you wanna take on your trip?

[00:14:26] Carl: Could we get clear about where you want to go first? And, and also realizing that where you want to go will change mid journey. Mid trip you might see a store you wanna stop at, or a mountain you wanna climb, or a river you wanna swim in. And so start by having these conversations close at home. Like, here’s one.

[00:14:44] Carl: I’ve been having with everybody I can corner. What’s your first memory of, in fact, Joe, I’m actually curious about this. What’s your first memory of money? 

[00:14:56] Joe: My first memory of money. 

[00:15:01] Carl: Let me just pause while you’re thinking about this, everybody listening. This is shocking and it’s not shocking to me anymore.

[00:15:08] Joe: You talk about this for a living? Yeah. Over 30 years between the time I was a financial planner and now financial media. 

[00:15:15] Carl: Yeah. And do you, your listeners would be familiar with Josh Brown talks more than anybody about money? I asked him same 

[00:15:22] Joe: response. We had a great time with Josh on the show. This would be a fun three person discussion 

[00:15:27] Carl: by the way.

[00:15:28] Carl: But the fact that you haven’t ever been asked or thought about, so now what is it? 

[00:15:31] Joe: Yeah, so I can’t think of the earliest one, but the one that strikes me is the first time where I got the difference, where I started to figure out value was actually kinda late Carl. It was in eighth grade. Hmm. In eighth grade I was working in this cornfield job, doing this job called detasseling.

[00:15:48] Joe: You take the tops off of corn and I remember I spent the entire time I was out there dreaming about this 12 speed bicycle I wanted to buy, and it was this amazing bicycle. I was gonna start training to travel across the United States when I was older and I could do it. I always saw these rides across America, you know, I thought it was really cool.

[00:16:06] Joe: So I save the entire time that I’m out there. I save up some ridiculous, to me at the time, amount of money, I think like $450. 

[00:16:15] Carl: Right? Right. 

[00:16:16] Joe: And I, and I go to the store, my mom takes me to the store and with my own money, I buy this 12 speed bike. And the second week I had it, I’m riding very quickly. I hit the wrong brake, right, which was the front brake instead of the back brake.

[00:16:31] Joe: My back wheel comes across the front. I go down in a heap, blood all over the place, but it snapped off, uh, the gear shifter and I didn’t have the money to get it replaced. And then I realized then that I spent my whole summer, like for the next 6, 7, 8 months when I didn’t have time to work because my, my mom said I need to focus on school.

[00:16:54] Joe: School became my job. Focus on, you know, all the other stuff. Didn’t have time or money to replace it. The thing sat. I remember thinking about was that the right use of money at that time, if I hadn’t thought through the ability to be able to maintain the bike, to actually have the, like the ability, I’d even thought through the fact that I probably wouldn’t be able to ride it much during the school year.

[00:17:16] Joe: You know? 

[00:17:17] Carl: See, I would be tempted to hijack the, it’s all that I can do to not hijack this entire show and ask you more about that. What did that feel like? And then the next question I would, episode 

[00:17:27] Joe: two or of Carl Richardson. 

[00:17:28] Carl: Yeah. The next question I would wanna ask, like how many of your listeners couldn’t answer that question for their spouse or partner of 10, 20, 30 years?

[00:17:39] Carl: I couldn’t. I would think 

[00:17:39] Joe: if I had trouble with it and Josh Brown had trouble with it. Yeah, I bet 95% of us had problems with that. 

[00:17:45] Carl: Yeah. Josh had no problem with the story, but I asked him, I’m like, how come you’ve ever talked about that? And he is like, I haven’t talked about that in 25 years or 30 years.

[00:17:53] Carl: How come you haven’t? He’s like, no one ever asked, which is ama So tactically. I didn’t know that about my wife of 27 years at the time when I asked her publicly on the show, I didn’t know the answer. I’ve been having that conversation with my kids. Here’s another interesting one, sort of like what I would’ve asked you at the end, ’cause that’s such a great story.

[00:18:13] Carl: I would’ve loved to have said like, what do you make of that now? And I would’ve loved to have said like, Hey, can you go back there for a minute? Like, what did that feel like when you had that realization that you spent your whole summer? What was the feel? I would be really curious about the feeling and then, then I’d probably move on to like, Hey, in junior high, were you one of the rich kids or the poor kids?

[00:18:32] Carl: And then you would probably tell me some story and then I’d remember to ask and you’d say something like, oh, we didn’t have a lot. People say that all the time. Oh, we were middle class, or, oh, we didn’t have a lot. Favorite question there. And again, this is all tactical, start close in. These are the kind of conversations, this isn’t about a budgeting app is my favorite question around anybody saying something like.

[00:18:53] Carl: We, we didn’t have a lot, but we were fine. Or any like statement favorite question is to say, Hey, how did you know? And then you get to this super, like, one day I was at school and I, I didn’t realize it, but I only had one pair of tough skin jeans and I was at, this is a real story for my friend Aaron. I was at school and there was this girl I really liked and she was showing some interest in me.

[00:19:17] Carl: You know, like teenage sort of stuff. We were playing football after school and I got grass stains on my jeans and I didn’t even think about it. I wore it the next day. And this girl was from a more well todo family. And she said, why didn’t you wash your jeans? And I told her I only had one pair and she never talked to me again.

[00:19:36] Carl: And you’re like, come on. How is that informing Josh’s story is informing Josh’s life, his story about losing a hundred dollars at sleepaway camp. You know, my friend Aaron’s story. I could go on and on, but that tactically, that’s what I’m talking about. What if we had some of those conversations gently with deep empathy, just to understand, not to teach anybody anything, but just to, I mean, I, I get soci, like I could barely contain myself about how badly I wanna ask you more questions.

[00:20:09] Carl: So it becomes an addiction of giving people space. That to me is how we solve this problem. 

[00:20:17] Joe: Do you think that, this was not on my sheet either, so you guys we’re throwing out my prep sheet, but do you think this is an issue in financial planning? Is that I feel like the financial planners who really get it, realize how much they are having to become much more of a psychologist and maybe even a sociologist.

[00:20:41] Joe: And how important that is to really connecting with your client and helping to guide them toward better decisions. I feel like there’s this gulf right now in, in the financial planning world between the people who are becoming Taylor Swift’s agent. You know where your client is a badass and your job is to understand their feelings, their needs, the things going on to sometimes be the tough person going, no, you know what, Taylor, get back out on that damn stage.

[00:21:11] Joe: This is what you do. Taylor gets back on the stage and goes, oh yeah, I love it. You know what I mean? Yeah. I’m not, I’m fighting with Taylor for Taylor’s own good. Yeah. But our client is rockstar and then we still have the world of people that think. That they have some control over the financial markets or they’re the Wizard of Oz.

[00:21:29] Joe: You come to me, Carl, and I’m gonna put together this portfolio. You can’t get down the street, which is a bunch of bullshit, you know? Yeah. Or, or I’m gonna, I feel like there’s bigger golf than ever between the haves and the have nots and the financial planning space. 

[00:21:42] Carl: I completely agree. I think there’s also a gulf between even the, I’m gonna use this word in an old definitional sense, not in a layered cultural sense.

[00:21:53] Carl: Even the privilege of having these sorts of conversations, like there’s a little bit of time and space that’s required to even have the, you’re just like, I don’t know what you’re on about, bro. I’m trying to pay my bills. I, I get that. But even at that level, ’cause I’ve had those conversations with people who are just like, I don’t even know what you’re talk.

[00:22:13] Carl: Even at that level, there’s some idea of like. Why, like what’s it for? What’s the like, even to be seen and heard in a spot where you’re like, I don’t even have time for that. I’m paying my bills. Oh my gosh, I can make room for that. And you’re right about the planning piece and I, I’ve been really thinking a lot about what is uniquely human.

[00:22:37] Carl: ’cause AI is really good at doing, humans have the potential of being really good at being. And I think what we’re talking about here is the need for more presence, the need for more listening, the need for more curiosity at all levels of income and, and financial struggles. Like, I mean, if I’m barely scraping by and I’m angry about it, which is reasonable just to have somebody go, yeah, man, there’s a reason you’re feeling that way.

[00:23:10] Carl: There’s a reason you’re bare. There’s a systematic reason. It’s not just you. There’s a systemic reason you’re feeling that way, and let’s get it out and let’s throw some things in the backyard and let’s do whatever. And then let’s, when it’s time, let’s think about like, are there some things we could do?

[00:23:27] Carl: And I think planners are becoming more and more aware of this. The job, the calculator side of the job is incredibly important as a technical skill, but it’s also, and you can, and this, it’s incredibly important and it’s worthless in the long term if we don’t know where we’re going. And so both of those become true.

[00:23:50] Carl: And last analogy, like I was in a self-driving car recently, and I’m, I’m a huge fan of self-driving money. Like I can’t wait for it in that Waymo ride, I’ll tell you, it was, it felt much safer than the Uber ride right before it really? Oh. Honestly, I was like, this is the most amazing cool. It felt much. I rode a couple different times and I would ride Ubers in between.

[00:24:18] Carl: Like one time we went down this alley and there was a dumpster in the way, and it, like the whole thing was incredible. Self-driving cars felt safer than a human driven car, but I still had to tell it where I wanted to go. And I also had to tell it more importantly, mid journey if I was like, oh, that’s, wait.

[00:24:37] Carl: I wanna stop there. And that to me requires a level of curiosity and presence that isn’t gonna ever be built in to the self-driving car. And it’s also never gonna be built into the self-driving money. 

[00:24:51] Joe: But I think that clarity is what we have trouble getting to because we’re this jumble of feelings, emotions, I gotta pay the bills, right?

[00:25:00] Joe: I’m trying to get ahead, my neighbor’s doing this thing, I wanna keep up with them. Like I’ve got this jumble of stuff. I love a story that you tell in your new project about this woman, Maxine. I don’t know if you remember Maxine’s story, but, but, but just this power of order. Can we talk about Maxine for a moment?

[00:25:17] Carl: Yeah. That it’s such a real story because there’s this huge metaphor. Maxine got referred to me when I was running my financial planning firm. Her husband had recently passed away. It had been weeks, right? They had taken care of all the stuff you do. And she was coming out of the really intense morning phase and saying, okay, I got some stuff I gotta deal with.

[00:25:44] Carl: And some of the stuff was this pile of mail. That it arrived. And in Maxine’s relationship, her husband was the one that took care of most of the financial matters because she took care of a bunch of other stuff, incredibly important stuff. So Maxine didn’t know much about the money as often is the case with one spouse or the other.

[00:26:04] Carl: And she came in with this literally like a banker’s box, like it looked heavy when she walked in. There was open mail and half open mail, and then a whole bunch of completely unopened mail. And I remember the emotional, but the very real physical feeling of saying, Hey, could I carry that box? Could I carry that weight for you?

[00:26:29] Carl: And we sat down and I said, Hey, what if we just took this meeting and talk a bit? We talked and then I said, Hey, would it be okay if between now and the next meeting, I’ll go through all this mail? I won’t throw anything away. I’ll open it all. I’ll organize it in a binder and I’ll put the stuff I think you should throw away in the back and we can, we’ll just go through it.

[00:26:47] Carl: And she was like, yeah, of course. And I, I remember when she came back, it was a, you know, a half inch, three ring binder, you know, that whole box, that entire weight. A nicely organized half inch, three ring binder, everything hole punched, no more envelopes. And we went through it together. And I, the, the, both, the sense when I first took the box took is not even the right, really the word I like when I first was able to help her with the box, the sense of relief.

[00:27:19] Carl: And then when she came back, this three ring binder, just, and what, what that points to me is like, there’s a very specific application, but I think the broader application too is like anytime I’m worried. Or stressed or weighed down with anything but financial. Like for instance, if I’ve been reading the news lately, which is just not a good idea, and I feel overwhelmed, I found it helps a lot to organize the garage or weed the garden.

[00:27:50] Carl: This isn’t some woo woo goofball thing. It’s not some California drum circle idea. It’s you go from feeling out of control, right? The news, the markets, the concern, your budget, like you go from feeling out of control to getting some small sense of control. If I just organize my desk, I feel a little better.

[00:28:12] Carl: And then what happens is that sense of control expands just a little bit. And again, we’re back to where we started the start close in, what’s the next smallest thing I can expand my sense? And then suddenly I’m like calling the bank. I got, or I’m doing the thing I’ve been avoiding and suddenly you’re like, why?

[00:28:29] Carl: Well, because this sense of control grew. That’s Maxine’s story. 

[00:28:33] Joe: What resonated with me from my old job of financial planning, Carl, was that my favorite part of the financial plan was setting up these milestones toward the big goal. And so we would meet every six months, my client would come in with the news, the economy, all this stuff going on.

[00:28:53] Joe: I wonder what policy is there gonna be? What’s gonna happen with the tax code? What’s gonna inflation is blah, blah, blah, blah, blah. What’s the market gonna do? It looks difficult. And I would go to, okay, in your financial plan right here, it says on the milestone, we need to be at $65,000 today, and let’s take a look at where we’re at.

[00:29:14] Joe: My client goes from all this stuff to, yeah, oh look, we’re $2,000 ahead. So we have some choices now, Carl, we can either slow down saving for this and have some fun today. We can keep the gas on and do more, or we could speed up the goal and do this sooner. Which one would you rather do? And all the sudden, guess what happens?

[00:29:33] Joe: All this 

[00:29:34] Carl: control 

[00:29:35] Joe: outside BS just evaporated. And it was, it was so phenomenal. Just seeing the power of a little organization. And, and I think this also speaks to the idea of getting out. I know that I think it’s you, you, you like having these conversations where people come. Is it a retreat at at your house or some place?

[00:29:56] Joe: My, yep. Just the idea of getting on a plane and getting out of your current mess by itself just puts you at 30,000 feet and it’s so good for your life to do that from time to time, I think. 

[00:30:10] Carl: Totally. Uh, two things I really wanna point out. One of my favorite things to do is to take these things that feel, I hinted earlier, I, I’m a big fan of California, right?

[00:30:17] Carl: But I hinted earlier about like the drums. Like it feels ethereal. I think it’s part of my job to take things that feel complex and crazy and ethereal and reduce them down. ’cause what you are talking about with your client story, there’s a framework for that. And I just think it’s so helpful when people understand what’s going on in their minds.

[00:30:37] Carl: The framework is at the top of a pyramid. If you imagine products, like if we had a pyramid, you imagine products or of the foundation of a house, the very, very, very, very top is this product idea. And in product you could put news, market economy, investments, you know, credit card budgeting out like whatever tactical product.

[00:30:57] Carl: And your concerns are almost always at that level. And when you’re talking about concerns at that level, you’re way out in the branches of the tree. So your idea of like, you know, it feels cra Yeah, there’s a storm blowing and the branches move a lot. And all you’re doing is saying, look, you had intuitively figured out that if I could pull them back to the roots of the tree and that roots is plan.

[00:31:20] Carl: And I think there’s one root foundation underneath plan, which is purpose, a sense of purpose. But I think largely we’re all thinking the embedded in the plan as a sense of purpose. If we can get out of those branches, I would just like start to set up habitually. If you feel like you’re, whoa unmoored, concerned, worried, to your point, you don’t even have to get on a plane.

[00:31:45] Carl: I love getting on a plane, but you don’t even have to get on a plane. Like go on a walk. And if you can rewire your brain that way so that when you feel that way and you can start noticing like I, I promise you, you will feel that way every time. Right now you read the news, when you feel that way, you think go someplace higher.

[00:32:05] Carl: And I like the higher metaphor, like even if you’re in like the, wherever the you are, I had a buddy in, I think he was in Iowa, and he was like, yeah, it’s a bridge. Like just somewhere where you get perspective. Suddenly you feel a little bit like, oh man, get outside, get your hands in the dirt, touch a tree.

[00:32:24] Carl: And, and again, not woo woo, it’s just like, it has this ability to go, oh, oh, I was out in the branch of the tree. I’m here now. Guess what? What you were dealing with out in the branches didn’t go away, right? Like that decision about which credit card or which investment or what to do is still there. You just have a different perspective than when you’re looking at it now.

[00:32:46] Joe: Well, there’s another facet of this that people would worry about my office all the time too, and I know. When you were working with people that was the same I’m sure for you, Carl, which is coming in and regretting the past. Hmm. You’ve got this wonderful line in your new project that says you can’t hedge yesterday.

[00:33:03] Joe: I’m like, we should all get that tattoo. ’cause yeah. How much time have I wasted just, and I’m a guy that I think knows better going, oh, IF that up. I shouldn’t have done that. 

[00:33:14] Carl: Yeah. One of my new favorite lines that will be in the next project, whenever that is, is there will never be enough money to pay for all your fears.

[00:33:23] Carl: So I think we have both sides of now we got the past, you can’t head yesterday, and I think a lot of shame and blame shows up from yesterday. And you can’t pay off for all your fears in the future. And that’s like worrying about problems that aren’t even problems yet. Right. Like, was that Mark Twain? I can’t remember what it was, but it was something like, I’ve had a million problems and some of them happened and a few of them happened.

[00:33:49] Carl: I think 

[00:33:50] Joe: we were joking a couple weeks ago about, uh, Robert Kiyosaki, about how he’s called 47 of the last two downturns. That’s exactly right. 

[00:34:00] Carl: That’s exactly right. Uh, a broken clock will be right twice a day. Yeah. I love that. So I, I do think one of the very core, most important things you can do and the never ending process of making good decisions with money that we often call financial planning is get really clear about where you are today.

[00:34:19] Carl: It’s, it’s kind of the first step. I used to think that should be easy. ’cause it’s just facts, right? They’re just numbers on a page. It’s just a balance sheet. It turns out that balance sheet is a nonfictional document woven with fictional stories. Like, I wish I would’ve bought more of that. I told you that was a dumb idea.

[00:34:40] Carl: Right? Like just every line on the balance sheet’s got a story. Sometimes they’re good stories, sometimes they’re bad. And even the good stories are often like, we should have done twice as much I told you. Like especially when there’s a spouse or partner involved. And what often comes up is shame or blame.

[00:34:53] Carl: And you just have to remember that responsibility says that was a dumb idea. Shame says, I am dumb. There’s a very big difference. And so shame serves no useful purpose. There’s no useful purpose for shame. Responsibility. Yeah, sure. And maybe even guilt. Okay. So if we can transform those a bit to turn them into like instead of losses, we turn them into lessons.

[00:35:22] Carl: Then we can start to move on. And sometimes that process of healing from that involves some, some process, some yelling, some some throwing things around, some running really hard in the mountains, like whatever it is for you. Get that all out. Find somebody who’s there for it, somebody who can take it. You probably have to pay them.

[00:35:39] Carl: They’re called a therapist. Right. And then, then you can move on to turning it into a lesson. I’ve got so many of those. I’m sure you do too. So many. There’s a, there’s a piece of property we drive by a couple times a week that, that we had an offer in for something like, I can’t remember what the number was.

[00:35:57] Carl: Um, but it was like $90,000, which was a lot of money. It’s still a lot of money, but it was a lot of money back then for us. We backed out of the offer because we didn’t, it wasn’t, we weren’t able to do it. Like we went and looked at our budget and we were like, we can’t do it. Well, that piece of property just sold for 1,000,004.

[00:36:14] Joe: Oh my. Yeah, but I’m at the point now. And even my response to that, by the way, is That’s 

[00:36:19] Carl: exactly right. That’s what I was just gonna point to. I’m at the point now where I don’t do that anymore. Right. That to me. But I was 10 years of that. Yeah. And guess what? The kids’ soccer field backed up to that property.

[00:36:30] Carl: So I was there, I got the chance to do what you just did to myself for 10 years, a couple times a week. And I did it every time. I was like, gosh, I can’t believe. ’cause it sold three different times between now and then, and I’ve seen each one. The first one was like seven 50. Now I can honestly say I feel it a little bit, a teeny bit, but I largely feel, hey, that was a good decision.

[00:36:54] Carl: You know? But quote unquote, I don’t even know if I call it a bad out. I used to say it was a good decision with a bad outcome. I’m not even sure it’s a bad outcome anymore. ’cause the overall outcome of our lives have been fine. But man, the first tendency is exactly what you felt. 

[00:37:07] Joe: Yeah. 

[00:37:07] Carl: And I felt for 10 plus years, and I’ve got fresher ones that I’m still working through.

[00:37:11] Carl: You know, where I’m like, gosh, again. Yeah. 

[00:37:15] Joe: That’s interesting because you know, I have two reactions. Number one is look at your life without that property. Big fricking deal. It doesn’t matter. The second one is, I heard this wisdom when I was maybe in my twenties, and I try to remind myself all the time, but it’s still hard, Carl.

[00:37:30] Joe: I mean, still I’m 57 years old. It’s still hard. I keep reminding myself the past does not equal the future, which is just a way to think about, hey, that happened yesterday. I can’t do anything about it. The future’s what I’m doing right now, and I can’t. 

[00:37:42] Carl: Yeah. Well, so far this entire conversation has been largely about kind of rewiring our response to certain stimulus.

[00:37:50] Carl: Just learning that, okay, great. When I feel nervous, I’m not gonna try to stop feeling nervous. ’cause by the way, that what you resist persists. So if I try not thinking about a beautiful ice cream cone right now, right? Like it just, it’s called the white bear problem in psychology. Like there’s no way if I tell you to not think, pink elephant, right?

[00:38:08] Carl: Yeah. Purple elephant, whatever. It’s there. So I’m not gonna try and resist the stimulus. The news, the nervous, this conversation, I’m just gonna try and rewire my response. And my response can go from shame to responsibility. My response can go, my response could go from shame to a great gratitude like you did, like look at your life now.

[00:38:31] Carl: So my response to feeling nervous about the markets, instead of like trying to figure out which stock I should trade, I’m gonna say, oh, that’s interesting. I’m feeling that. I’m gonna say, Hey, what does my plan say? We’re not trying to get rid of the stimulus ’cause it’s, there’s things we can do, but it’s largely impossible in the world we live in.

[00:38:49] Carl: We’re gonna just try and rewire the response. 

[00:38:52] Joe: If only somebody had written a book, which kind of encapsulated all this stuff, which took these wild, disparate, not desperate, disparate ideas and built them together in a simple way. Uh, if only someone had done that, and it turns out right that you were able to do this.

[00:39:15] Joe: It is called Your Money Reimagining Wealth in 10 simple sketches. 101. What’s that? 101 simple sketches. Hun? I said 10, 

[00:39:22] Carl: didn’t I? That’s just the first chapter. But wait, 

[00:39:26] Joe: but wait, there’s what you forgot. I was gonna do the, but wait, there’s more. Oh, sorry. Like the old Kaytel records case. Alright. Yes. I’ll tell you what, if you buy 10, Carl’s gonna throw in 91 more for free.

[00:39:38] Joe: Exactly right. Are you sitting down? 101 Simple sketches. By the way, I feel like you and another friend of mine are kind of blood brothers who don’t know each other. I look at your work and our friend Austin Cleon, who’s been on the show a few times, uh, he very similarly when he talks about the creative process.

[00:40:00] Joe: Do you know Austin at all? 

[00:40:01] Carl: Yeah, I interviewed Austin for 50 fires, but I, I stole like an artist from Austin ’cause the Sure. The physical frame of this book. Oh, 

[00:40:11] Joe: it’s, there’s 

[00:40:11] Carl: supposed to be a, an acknowledgement of that. It didn’t get in the first printing, which they’re already doing the second printing, so it’ll be in there.

[00:40:17] Carl: But yeah, his books are six by six and these are seven by seven and they’re Matt Finnish. Austin’s had a huge impact on me despite just having one conversation with him. 

[00:40:27] Joe: Monster impact on me as well. And, um, just both of you have, and thank you so much for mentoring our stackers today, Carl, I appreciate it so much.

[00:40:36] Carl: Cheers, Joe, that was so fun. Thanks for doing it.

[00:40:43] Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and I love how Carl Richards is able to take what seems complicated and boil it down to the core, don’t you? Well, let’s take a page on a Carl’s book and do the same with today’s trivia back in 1938. On today’s date, two men. Chester f Carlson and Otto Corny figured out how to move a message from a glass slide to a sheet of wax paper.

[00:41:08] Doug: Corny was not impressed with the results and left the partnership. 10 years later to the day, Carlson revealed the invention to the world. He approached IBM, who passed on the technology finally selling it to the Halloid company. Here’s today’s question. What is the name you and I know the Halloid company as today?

[00:41:28] Doug: I’ll be back right after I go. Simplify the idea of Joe’s mom making dinner for all of us. It’s really easy. You just triple the portion Seism Ma for the rest of the crew, and then double it again for me.

[00:41:49] Doug: Hey there stackers on Copy Lover and the guy whose third grade teacher called an original Joe’s mom’s neighbor, Doug. The term Xerography is from the Greek words, zeros meaning dry and graphene, meaning writing. That’s the technology that Carlson and Corny invented on today’s date back in 1938, and is why the Halloid company who bought the technology renamed themselves Xerox, and now two guys who copy all my best dance moves.

[00:42:20] Doug: It’s Joe, NOG. 

[00:42:24] shout otu: Hey, this is John in Seattle, and when I’m not telling terrible dad jokes to anyone who will listen, I’m Stacking Benjamins. 

[00:42:31] Joe: Big thanks to Carl again for spending time in the basement. And it’s funny, og, like Carl said, we treat money like it’s a math problem, so we bring out the calculator.

[00:42:42] Joe: Yet we really need to just, we need to check our, our emotions at the door. So, so important. Let’s do a headline. 

[00:42:51] headlines: Hello Darlings. And now it’s time for your favorite part of the show, our Stacking Benjamins headlines. 

[00:42:58] Joe: Our headline today comes to us from investment news. I found this really a compelling discussion on investment news.

[00:43:05] Joe: And for those of you that don’t know investment news, which is most people, I’m sure this is a resource for advisors. It’s an industry rag, as they call it, so I love. When we do a headline from investment news because of the fact that it’s life on the other side of the table, and they had this discussion on investment news, uh, I won’t link to it in the show notes, page advisors weighing in on the benefits of options as a hedge against concentrated stock risk.

[00:43:35] Joe: And it is interesting, we’ve had a market that’s gone up great. Uh, in fact, this piece starts off by saying shares of NVIDIA are up 1250% over the past five years. So if somebody was fortunate enough to have purchased Nvidia five years ago, at that time, OG it wasn’t a concentrated position in your portfolio, right?

[00:43:57] Joe: And now because of the market run, it truly could be a problem in your portfolio because your portfolio now, if you haven’t sold any office, it’s gonna go where Nvidia goes. You have a couple choices, you can, number one, you can sell it right now, or number two is you could maybe use an option strategy to hedge against the risk that it wrecks your portfolio.

[00:44:19] Joe: Clearly, if Nvidia goes up, a lot of people would want a piece of that, which is why you might have an option to sell instead of selling it. So the way this works stackers, is that instead of selling off your Nvidia or a piece of your Nvidia, you instead do an option to sell. And that option to sell says I’m gonna sell it at a predetermined price.

[00:44:40] Joe: And in this case, it would be the price that is trading at right now. And instead of selling it, I’ll wait and see if it goes up or down. If it goes down, I’ll just sell the option and get the price it’s at today. If it continues to go up, then heck, then the option expires. I paid a little bit for this quote insurance policy, and then I’m good.

[00:44:58] Joe: But what do you think about using options? Instead of selling off a piece of your portfolio that might be too concentrated og instead of using options to mitigate some of the risk in the portfolio. 

[00:45:12] OG: I, I think we have to talk about the difference between, like use the right terminology here because I think a lot of people will confuse this or could confuse this with part of your compensation, right?

[00:45:22] OG: So you’ll say, well, I get options for my pay. I get, you know, I get restricted options for my bonus, or I get non-qualified options for my bonus. It works somewhat similarly in that, you know, you have this grant that has a specific exercise price, but this is a little different. The way that an option contract works on a stock that you already own is just like you talked about, you’re making a promise in exchange for either a premium, that you’re gonna receive some cash today, or a premium that you’re gonna pay to fulfill the obligation.

[00:45:57] OG: So NVIDIA’s at $180 a share and you say. I’m okay with it bouncing around ’cause that’s what stocks do. But I don’t want it to go below one 50. And so you can buy insurance at one 50 and say, you know, if it dips below one 50 between now and the end of March next year, then I get to get out at one 50. So if it goes down to one 60, then no, nothing happens.

[00:46:19] OG: If it goes to 1 51, nothing happens. If it goes to 1 32, I’ve got this piece of paper here that says, whoa, whoa, whoa. Says here, I get to sell at one 50. I’m gonna exercise it now I’m gonna use my option to get out at one 50. And you can do it the other way too. You can say, you know, it’s at $180 and if it ever went to 2 25, I would sell that thing like a hot cake.

[00:46:41] OG: And in exchange for that promise, you can get some money today. So you can say, well, how strongly do you feel about that? I feel real strongly if that hits 2 25 between now and March, I would a hundred percent get out guaranteed. Put your money where your mouth is, write it down on a piece of paper and say, I promise to do it.

[00:46:59] OG: In exchange for that promise, they’ll give you some cash today. So you can do both sides of this transaction and you can do it with or without owning the stock, which makes it even more risky on top of it. Ultimately, from an investment standpoint, let’s talk about it that way. So you’ve got the stock, you’ve got a thousand shares, it’s $180,000 of your portfolio, it’s 85% of your portfolio, and you go, I feel like I should.

[00:47:27] OG: The right answer is to diversify, right? Oh gee, Joe, like that’s the right answer. But man, I just don’t want to, because if I do, and this thing goes from 180 to 360, I just lost out on 180 grand. I need you to take that outta your mind. You have to evaluate your investment decision based on what it is today.

[00:47:48] OG: The information that you have today, if you have $180,000 of Nvidia stock. You have a $200,000 investment portfolio, it’s overweighted, and you have to diversify that. If you wanna be smart from an investment perspective, that doesn’t mean it’s not gonna go up. That doesn’t mean you say, well, I’m not gonna do that.

[00:48:07] OG: I’m gonna keep it concentrated and it doesn’t go up 10 x from here. And you say, I told you so. I knew. I knew I was glad I didn’t, didn’t diversify that. Now I’ve got a million dollars. This is a way better deal. Absolutely that could happen. But the thing that happens with diversification is you trade away the opportunity to make a killing in exchange for never getting killed.

[00:48:28] OG: That’s the trade. I can’t tell you what’s gonna happen with any individual stock, nor can anyone, which is why buying an ETF or buying a diversified portfolio of big companies and small companies and US based ones and non-US based ones makes a lot of sense to me because it’s way easier to say, what is the overall economy gonna do over the next 30 years of my life?

[00:48:49] OG: It’s gonna grow. That’s what I believe in my soul. I’m not smart enough to say which AI chip manufacturer is gonna pull out ahead, which Raindrop is gonna hit the bottom of the, of the windowsill, the first, the fastest. I’m not smart enough to pick that. 

[00:49:05] Joe: People who are new to options may be thinking right now.

[00:49:08] Joe: They’re like, wait, I, I heard options are this risky thing. And to your point, especially when you talked about trading options without the underlying money, that’s incredibly risky. Without the 

[00:49:17] OG: underlying stock. Yeah, yeah. 

[00:49:18] Joe: Without the underlying stock. This thing we’re talking about is not risky at all because you’re willing to give up.

[00:49:25] Joe: Um, I 

[00:49:26] OG: disagree with that. Well, you’re 

[00:49:27] Joe: willing to give up the position, number one. Number two is you also covered up the risk of if it goes down by buying the option to sell it today. So where is, where is my risk then? 

[00:49:39] OG: Well, there’s two things. First, it’s the cost structure. So I, I use the example of Nvidia being at $180 a share today, and you saying, Hey, I’ll take the first 30 bucks, right?

[00:49:48] OG: I’ll go to one 50. It will cost you today as the day we record it, about $8 per share to ensure that at one 50. So number one, if you have a thousand shares, $8, that’s eight grand of insurance premiums. All you guys out there shaking your head, going, going, I can’t buy whole life insurance. It’s ridiculous.

[00:50:08] OG: And you’re gonna spend $8,000 on NVIDIA options, Nvidia insurance, basically, 

[00:50:13] Joe: I wanna bring you something up for the new stackers who aren’t familiar with the Greatest Money Show on Earth Circus and how we put this together. OG doesn’t see these pieces before we go live. He doesn’t see any of it. The very first thing an advisor says, OG, in this piece that is the wellspring from where I thought we’d have the great discussion that we’re having.

[00:50:38] Joe: The very first advisor said, most people see this strategy of, Hey, I’ll just place an option. And they think, oh great. Yeah. Why the hell wouldn’t I do that? Let’s do it. He said, but then they see the cost of this insurance ’cause that’s what it is. It’s an insurance policy. They see the cost. Most people, the, the guy uses the word appetite.

[00:51:00] Joe: Most people don’t have the appetite for the. Amount of money it’s gonna cost you, you are just, you’re paying so much money to try to stay even that you’re not staying even, you’re not staying anywhere close to even, because you’re spending so much money on this insurance policy. That’s the option. Yeah. I 

[00:51:17] OG: mean, so if the stock is 180 and you wanna insure it for one 50, so a, you’re taking a $30 per share loss to get your insurance to pay out, right?

[00:51:27] OG: And then it costs you eight bucks for the next, what, five months? So $8 on 180 is 5%. A little bit less than 5% of the, like, you have to make so much money just to offset the premium of the insurance. The option cost that it’s really hard. So I think one of the risks is this 8,000 bucks, you could be doing other things with it.

[00:51:50] OG: The second thing is, is that it ignores the volatility and the fact that generally speaking, the market goes up. And I can’t talk about Nvidia saying, I, I know it’s gonna go up. Today could be the high price, the highest price it ever has. There was a day where Kodak was at an all time high and then it went down from there and ceases to exist.

[00:52:08] OG: Today that’s happened, and it’s happened for Pan Am and it’s happened for thousands and thousands of other companies, which is why buying an ETF that’s largely diversified is such a great idea. ’cause you don’t have to play the game of which one of these tech companies is gonna be great tomorrow. Like who cares?

[00:52:25] OG: You just own everything in itself. Cleaning. When something just doesn’t do well, it falls off and it’s replaced by the thing that is, so it’s totally fine. But if you look at this purely from a volatility standpoint, so there’s some chance the stock’s at 180 right now. I got my piece of paper that says I can get out at one 50 and it goes to 1 48 and you go, ha ha, ha, ha ha.

[00:52:47] OG: I’m out at one 50 and three days later it’s back to 180. Now what happened? You lost 30 bucks a share to save $2 a share to save yourself from the volatility. That is the very thing that gets you the upside that you’re looking for. This is the thing that people have to wrap their head around. Volatility is both sides.

[00:53:07] OG: When you see a stock goes, oh my gosh, this stock goes up. You know, it’s up 10 x in the last five years. That’s one side of volatility. It’s the good side. It’s the side we like. It’s the, it’s the fun part, but it can work the other way just as easily. And so when the stock goes from one 20 to 180, what was the most recent one that went crazy?

[00:53:27] OG: Uh, a MD or something? Some, I think it was a MD, just skyrocketed one day. The people who had those other side of the options, they thought they were, Hey, we got this free money, we can get these, you know, they had a huge risk there too. So there’s no such thing as a free lunch here. This is the biggest piece.

[00:53:45] OG: If you’re worried about over concentration in your portfolio because of a stock, you have to do one of two things. You have to either sell the stock and diversify it. Or build more money around that, the stock that you have. So you say, so 

[00:54:00] Joe: it’s a lower percentage of your portfolio 

[00:54:01] OG: then? Yeah. If you look at your brokerage account and you go, man, I got lucky, I bought a thousand shares of Nvidia five years ago and now that stuff’s worth 200 grand in my account, then the rest of your money needs to not be tech.

[00:54:14] OG: You know what I mean? Like your 401k needs to be in small companies and international and your A Roth needs to be in small companies and international, because largely a large company fund is gonna be heavy tax. So you have to just offset that. Or the smart thing is you just say, okay, I, I did well. I made a killing on this stock.

[00:54:34] OG: I got lucky. Admit it, and just go, I need to take some of this off the table. Take some of these profits off the table, diversify it, pay your capital gains tax, and move on with life. And if this money is in a qualified account and there’s no tax issues, shame on you. You should be diversified. 

[00:54:49] Joe: I think for an advanced investor, so we, you know, we’ve got kind of different levels of stackers.

[00:54:54] Joe: We got people that are brick layers. You’re just building your foundation. Throw any idea of building your foundation out of options, out the window because no, yeah, there, there is no foundation. I mean, this is a three little pig story, right? Build the house a brick. Options are not, options are a 

[00:55:12] OG: financial instrument who’s intrinsic value.

[00:55:15] OG: The end value, the terminal value of the option contract is zero. All options end at the end of their term at zero. Everything else between zero and whatever you pay for it. And what you sell it for is all volatility and speculation. It doesn’t mean you can’t make money. There’s plenty to go on Wall Street bets on Reddit, and you’ll see somebody tomorrow that goes to, do you see what I, I put a hundred bucks in this, made 47,000 in three minutes.

[00:55:44] OG: It happens. Absolutely it does. I think 

[00:55:46] Joe: for the advanced Benjamin Builder that you’ve built up a sizable portfolio and it’s almost like somebody who’s a good fisherman. I’ve been going fishing a little more lately with my buddy Todd. Todd is a great fisherman, goes out all the time, og he knows exactly what lure to use in each situation.

[00:56:03] Joe: He knows exactly he, he knows the bait, he knows the depth, he knows the part of the lake. And for those people that are much more of a surgeon, knowing where to use an option can be a valuable part of your risk strategy. But the thing I wanna highlight that you said earlier is that the biggest mistake I see, and I see this 95% of the time with options when people are just starting out, is that they’re using it to get rid of the volatility in the position.

[00:56:33] Joe: You set your option way too close, way, way, way too close to the point that it’s at now and you end up neutering your portfolio. I think what I, we really need to highlight stackers is you need that volatility. You have to have that volatility because the volatility on the upside is the only thing that’s gonna make it.

[00:56:52] Joe: So you don’t need to save dollar for dollar every piece of your retirement, you want your money to do it. And using options willy nilly, as mom says, to control risk in your portfolio is just gonna be a disaster. Just an absolute, a mitigated disaster. So that’s, that’s frankly why I don’t use ’em. I think they can be good, but I think you really gotta be an expert fisherman and go, oh, guess what?

[00:57:17] Joe: I’ve got this one little case. People hear covered call strategies. I’m not gonna get into what a covered call strategy is, but when you first heard about covered calls and somebody OG explained covered calls to you, I was like, why the hell wouldn’t I do that every second of every day? Free money and money glitch just makes so much sense.

[00:57:36] Joe: And then you get in, you start looking at the call options and you see where the pros are pricing these things. It is a. Ton of work for almost no juice because these people aren’t stupid. The algorithms are using aren’t stupid. They, these people have this stuff priced so professionally that you’ve gotta man spend a ton of time to eke out just a few drips.

[00:58:01] Joe: And I don’t know, after playing the covered call game a little bit myself, I go, why would I waste my time doing this? 

[00:58:08] OG: It works when it works and then when it stops working, it stops working in a very, very fast hurry 

[00:58:15] Joe: very, very quickly. So love the idea of option stackers. I’ve seen options a lot in the market and I think that’s because we’ve had so much talk lately.

[00:58:24] Joe: Oh gee, volatility. People go start going, oh, volatility. How do I, how do I control at 

[00:58:29] OG: all time high. 

[00:58:30] Joe: How do I control downside risk? Congratulations. I’m gonna use options. I’ll link to this piece on our show notes at stack Benjamins dot com. One thing it does talk about og, that I worry about, there’s some guy throwing shade here going, you know, sometimes advisors don’t wanna use options just ’cause your advisor doesn’t understand options.

[00:58:49] Joe: When you read that, you’ll read that in the Wall Street Journal, right? Somebody just throwing shade. What do you think about that? When somebody says, well, is the problem og, that you don’t understand options, that’s why you don’t want to use them. 

[00:58:59] OG: I always think it’s interesting when I go to my semi-annual physical and I help, I will have recently read or listened to like Peter Atia or you know, somebody about something and I’ll spout out something to my physician.

[00:59:16] OG: He’s a really great doctor. He is a, he is a great bedside manner and, and is very forward thinking. And I’ll say, well, you know, uh, statistically blah, blah, blah, blah, blah. And he’ll just go, Uhhuh. Yeah, okay. And or if he’s feeling a little sporty, he’ll kind of hit me back with, you know, the kind of 2 0 1 of that, or the 3 0 1 of whatever I just said.

[00:59:36] OG: And then I look like I got hit by a bus. ’cause I don’t know any of those words. There’s so many syllables in, in the doctor words that I don’t know. It’s not that he didn’t know to talk to me about it. He just had already decided that it was so not important that he wasn’t gonna spend any amount of the time with me to talk about the thing that he didn’t need to tell me how smart he was to say, well, just so you know, I did all this research on this thing that has no material importance to you whatsoever.

[01:00:05] OG: And, but, uh, it’s, you know, I, you don’t need to know about it. So there’s a lot of that sometimes when you are working with a professional. They have already thought about that and they’ve already decided that they’re not gonna talk about that. ’cause it’s not appropriate. It’s not that they don’t know, it’s just that they don’t have any value in bringing that up.

[01:00:28] Joe: I found when I was an advisor, I loved working with engineers, but engineers were most likely the person that was going to do in my office exactly what you just said. And so I would have to go deep with them first to cure the fear that I didn’t know what I was talking about. And then I could say to them, but you know what, this doesn’t matter ’cause you haven’t saved any money.

[01:00:49] Joe: If I had said you hadn’t, you haven’t saved any money. Yeah. At first they would’ve thought it was a smokescreen. 

[01:00:54] OG: Right? 

[01:00:55] Joe: But once I went down the rabbit hole, like your doctor doing the 2 0 1 language, 2 0 1 3 0 1 doctorate level language. And then he says, yeah, but, oh gee, look at what you’re shoving in your pie hole.

[01:01:06] Joe: Yeah. 

[01:01:08] OG: Then you like my doctor’s favorite phrase the other day, this is so great. And we were talking about blood pressure and you know, whatever. And he goes, I said, do you think I should, you know, the guidance says these numbers and I’m kind of right at ’em, and do you think I should take a pill for it? And he goes, no, you should eat more or less.

[01:01:25] OG: And I was like, what? He’s like, you know how when you’re like, I should eat more? Yeah. Do that less, a lot less. Actually eat more, less, way less than you do now. Oh, that’s great. We will, 

[01:01:37] Joe: as I mentioned, link to this piece in the show notes. Uh, 

[01:01:39] OG: get all your option trades at Stacking Benjamins dot com slash options trading for the win.

[01:01:47] OG: Subscribe to our option trading course. No, don’t. 

[01:01:49] Joe: No, 

[01:01:50] OG: no. We don’t have that. There will never be, we never have that. 

[01:01:52] Joe: We’ll have some guides you can meet with og. Yeah. Uh, there’s so many things you can do. You do a 

[01:01:57] OG: lot of good stuff or, or Yolo your entire life. Savings into Nvidia options. 

[01:02:05] Joe: You know, if I was gonna do that, I’d just go to Vegas.

[01:02:08] OG: Actually, 

[01:02:08] Joe: I think 

[01:02:08] OG: Vegas would be more fun. 

[01:02:10] Joe: Have the whirlwind weekend. Get it over with. Yeah. So much more fun than watching it slowly circle the drain. 

[01:02:17] OG: I mean, it slowly circles the drain in Vegas too, but there’s a lot of hope when you’re pulling that wheel of fortune arm and it’s like, yeah, hell far, Chad, boop boop boop, boop.

[01:02:28] OG: And then you press the button, you’re like, come on, hit the thousand, and it’s like $20. You’re like, 

[01:02:33] Joe: and there it is. Or I’d lost another 20 and then another or so I’ve 

[01:02:36] OG: been told, I don’t know. Yeah. Rumor has it. Rumor has it. That’s how that sounds and goes. 

[01:02:41] Joe: Let’s mosey out on the back porch. Just a few things for you, stackers.

[01:02:44] Joe: If you’d like to help us make episodes, we take your questions. We had a great question episode on Monday. Also, by the way, if you love the q and a on YouTube, we have an entire channel of our YouTube page, which is just your questions. So to ask your questions, head to stacky Benjamins dot com slash voicemail.

[01:03:07] Joe: And if you love that, just dive into our YouTube youtube.com/stacky Benjamins. We also hang out on Instagram on TikTok increasingly, where OGs a big star. Hmm. 188,000 people in counting watched OG counting. Uh, lately I’m gonna begin doing some TikTok lives, I think, just to have some fun. You’ll never catch me, bro, over there.

[01:03:31] Joe: Nope, you won’t see OG there, but, but no, I’m just saying 

[01:03:33] OG: you’ll never catch me. I’ve got such a lead on this. I’m so viral. You’re, 

[01:03:38] Joe: yeah. I think my biggest TikTok is maybe 1500 in your, oh God, I you, I know, right? I love the discussions that we have on Spotify. I try to put up polls from time to time, so feel free to say hi to us and chat up the episode on Spotify as well.

[01:03:56] Joe: And if you wanna just join the conversation. We have local meetup groups right now in Seattle and in the Twin Cities. And we have our basement Facebook group. So if we don’t have one where you live, just go to Facebook and put in Stacky Benjamin’s basement in Facebook. You’ll get to join other stackers chatting, not just about the show, but people ask questions and generally hang out.

[01:04:17] Joe: So lots of ways to get involved in the Stacking Benjamins community. Alright, that’s gonna do it for today, Doug. Man, you got it from here. What are the three things we should learn from today’s show? 

[01:04:27] Doug: So what’s stacked up on our to-do list for today? First, take some advice from Carl Richards. Does your financial plan seem complicated?

[01:04:36] Doug: Have a bias towards simplifying? Not only will your life feel better, your financial plan will also probably be better. Zach, take some advice from our headline options. Not necessary, because again, that complicates the plan. But the big lesson explaining options to Joe’s mom is futile. She prefers Carl Richards Keep it simple approach.

[01:05:01] Doug: The only option she talks about is quote, whether to buy an option to trade us to the neighbors. Wait, what? Thanks to Carl Richards for joining us today. We’ll also include links in our show notes at Stacking Benjamins dot com. This show is the Property of S SP podcasts, LLC, copyright 2025, and is created by Joe Saul-Sehy.

[01:05:27] Doug: Joe gets help from a few of our neighborhood friends. You’ll find out about our awesome team at Stacking Benjamins dot com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. Oh yeah, and before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know.

[01:05:49] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s Mom’s Neighbor, Duggan. We’ll see you next time back here at the Stacking Benjamin Show.

[01:06:53] Joe: So I have this problem, which is that there’s a pill for that. Well, maybe not for this one. I’m headed to Dollywood. Which is a theme park. I never thought that I wanted to go to my lovely spouse because we’re headed to the National park in West Virginia. My lovely spouse said, we have a little bit of extra time before my daughter and her boyfriend join us on Friday.

[01:07:18] Joe: Let’s just see what we could do. We’re gonna have most of the day on Thursday. Well, what can we do? While we’re in the Smoky Mountains, we’ve already gone to Great Smoky Mountain National Park. We’ve done the Blue Ridge Parkway, Shenandoah National Park. All those places are beautiful, og, and all of a sudden, outta the blue, my wife, who does not love theme parks, goes, why don’t we go to Dollywood?

[01:07:40] Joe: So I find out that this park, so I start doing all this research. The number one thing to do at Dollywood is eat the cinnamon bread. Apparently there’s this bread that’s cinnamon and icing and uh, I saw a video of a dude who he’s already eaten all the cinnamon bread and he shows the bottom of the little tin.

[01:08:01] Joe: It comes in and it’s still hot. Well, of course it’s piping hot when you get it. And this loaf all of the cinnamon sugar and the icing coagulate at the bottom. Okay, go on. And he’s got his face in the tin and he looks at the camera for a second, goes stop judging me, and then shows his sho his head back in the tin.

[01:08:23] Joe: I’m trying so hard to control my weight and my impulses. Talk about what your doctor said. This is, this is why I thought of this. Yeah, eat more or less. Stop doing the thing. Stop doing that. I don’t know how the hell. I’m gonna keep myself from buying like 10 loaves of cinnamon bread. 

[01:08:41] OG: Oh, you just, no, you just do it once.

[01:08:43] OG: You know, you have, you can have one day. This is the big myth about there is no perfection. So just that’s your day off. Just have one day. Now what you can’t do is you can’t eat two loaves. Buy three, eat ’em on the road, then take one home and eat it later. You know, if you’re gonna put down five loaves, put down five loaves in one day, bro.

[01:09:05] OG: I get it. Get after it. That’s it. You know, 

[01:09:10] Joe: your doctor told you that. Your doctor said, here’s what you do. 

[01:09:15] OG: That’s what he said. There’s a guy that I follow on Instagram that is, uh, a golf person. His name is Manolo, and some people are familiar with Manolo, but recently he talked about, uh, getting in shape.

[01:09:29] OG: This might be applicable to you. This is advice for me. Okay. 

[01:09:33] bit: Hello everyone and happy Christopher Columbus Day, although he was not a very nice guy, he was a courageous Pedro and it takes courage to do some courageous shit like getting into the shape. Did you wear your shirt all summer, even though you said this was the summer that you were gonna get so nasty and so fit and you are gonna get ripped up and you are gonna have more packages than FedEx in your abdomen.

[01:09:53] bit: You didn’t do it. That’s because it starts in October of the previous year. If you want to be a nasty princess and be fit a fantastic sea, he’s about to train somebody and that is what the gymnast looks like. A lot of you don’t know what a gym looks like. You should. So I’m gonna start putting out that I’m gonna be doing nasty shit.

[01:10:11] bit: All the way until the end of the year so I can make sure that the tanky topic comes off for the pool next year. It starts right now. This is not a story, this Sell a G post. Wash it over and over again. Do some courageous, change your life, change your golf game, change your business. It starts with your new boyfriend, Jim.

[01:10:29] bit: That’s it. 

[01:10:30] OG: Starts with your new boyfriend, Jim, 

[01:10:32] bit: Joe.