Everyone inherited financial wisdom from somewhere — a parent who clipped coupons at three different grocery stores, a first job, a financial guru, or just the culture you grew up in. Some of those beliefs serve you. Some of them quietly hold you back. Chris Hill of Money Unplugged joins Joe, Paula Pant, and OG to share the money habits they’ve had to unlearn — and then the whole group plays a round of In or Out on some of personal finance’s most popular rules.
What You’ll Walk Away With
- Why Paula’s childhood coupon-clipping ritual wasn’t really about frugality — it was about an unstated belief that your time is worth nothing, and how that belief shapes everything
- Chris Hill’s 20-year belief that dividend-paying stocks are for old people — and the specific Apple moment in 2012 that finally broke it
- OG’s admission that despite the math argument, he’s never once seen someone actually execute the “invest the difference” 30-year vs. 15-year mortgage strategy in real life
- Why “more money will fix this” is the belief most people never fully unlearn — and OG’s honest accounting of what he thought at $17,000, $170,000, and beyond
- The In or Out verdict on five popular financial rules: everyone should own a home, pay off debt before investing, never carry a mortgage into retirement, you need a budget to build wealth, and whether financial independence is mostly behavior or math
- Paula’s anti-budget framework — why it works when there’s a wide enough gap between income and spending, and the one scenario where a real budget actually becomes necessary
- Chris Hill on why surrounding yourself with people who aren’t impressed by your success might be the most underrated risk management tool in your financial life
- The Isaac Newton problem applied to successful people: why brilliance in one area creates a false confidence in all areas — and why guardrails matter more the more successful you get
- Why OG argues that if the leverage-your-mortgage math truly worked reliably, you’d be using the same logic in your Schwab account — and why almost nobody does
- What Melissa from Detroit did this week that every Stacker listening should know about
Why This Matters Now
The most expensive financial decisions are often the ones you’ve never questioned because someone you trusted taught them to you early. This episode is the permission slip to stress-test those beliefs.
From the Basement
Chris Hill joins Joe, Paula Pant, and OG to dig into the money habits and inherited beliefs they’ve each had to unlearn — before the whole group debates whether five of personal finance’s most popular rules actually survive contact with real life. Doug arrives with Lou Gehrig trivia and makes everyone do inflation math from 1939. Chris plays for Team Jesse Cramer. The gap between first and second place closes considerably.
Resources Mentioned
Stacking Benjamins Community — stackingbenjamins.com/basement
Money Unplugged podcast — Chris Hill; recent episodes featuring Joe Saul-Sehy and Paula Pant; available wherever you listen to podcasts
Afford Anything podcast — Paula Pant; upcoming episode on how to think through business decisions with a Harvard professor and longtime practitioner
Surfshark VPN — surfshark.com/stackingb; code stackingb for four extra months
Stacking Benjamins Newsletter (The 201) — stackingbenjamins.com/201
OG financial planning calendar — stackingbenjamins.com/og
Our Topic: Money beliefs and habits to unlearn
During our conversation, you’ll hear us mention:
- Inherited money beliefs
- Cheap vs. frugal
- Hyper-frugal childhood
- Coupon-clipping lessons
- Grocery-store savings
- Time-value tradeoffs
- Salary mentality
- Ceiling mindset
- Entrepreneurial role models
- Scarcity thinking
- Lifestyle creep
- Self-reliance
- Success and ego
- Truth-teller friends
- Leverage risk
- Slow wealth building
- Financial independence myths
- Enjoying the journey
- Dividend-stock bias
- Apple’s dividend
- Individual stock guardrails
- Mortgage payoff math
- 15-year mortgages
- Homeownership pressure
- Debt before investing
- 401(k) matches
- High-interest debt
- Mortgages in retirement
- Budgeting vs. planning
- Behavior over math
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Chris Hill
Another thanks to Chris Hill for joining our contributors this week! Hear more from Chris on his show, Money Unplugged with Chris Hill at Money Unplugged with Chris Hill – Podcast – Apple Podcasts.
Paula Pant
Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paula on Twitter: @AffordAnything
OG
For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- When Lou Gehrig’s 2,130 consecutive-game streak ended in 1939, Americans were still climbing out of the Great Depression. Adjusted for inflation, if you earned Lou Gehrig’s 1939 salary today, how much would it be worth in today’s dollars?
Mentioned in today’s show
- Stacking Benjamins – Surfshark use code “Stackingb” at checkout to get 4 months free.
- How to Create an Investment Policy Statement | Stacking Benjamins
Join Us on Monday!
Tune in on Monday when we jump into the topic of the red-hot SpaceX IPO. Did you miss out on the world’s greatest investment? How do IPOs work anyway?
Miss our last show? Check it out here: Isaac Newton Lost 80% of His Fortune in a Bubble — What That Teaches Every Investor (SB1856) | Stacking Benjamins
Written by: Kevin Bailey
Episode transcript
[00:00:00] opener: All right, here we go. Hold your ears, folks. It’s showtime
[00:00:11] Doug: Live from the basement of the YouTube headquarters, it’s The Stacking Benjamins Show
[00:00:26] Doug: I’m Joe’s mom’s neighbor, Doug, and even the best of the best have had some bad money habits. What are some that they’ve had to unlearn? We’ll ask them so you can build your habits better and stronger. But that’s not all. After today, I’m sure you’ll be better and stronger at answering one of my trivia questions, and we’ll see if one of our contributors can even come close.
[00:00:51] Doug: And now, a guy who’s nowhere near close to unlearning his love of ice cream, it’s Joe. Joe Saul-Sehy.
[00:01:03] Joe: Hey there, Stackers, and happy Friday to you. I am Joe Saul-Sehy. And you know what, Doug? You never wanna get rid of your love of ice cream. I mean, who wants to get rid of that?
[00:01:12] Doug: No. No, no, no, no. Joe, today I’m operating purely on momentum and bad decisions, and one of those is already half a gallon of ice cream today
[00:01:23] Joe: How could it be wrong when it feels so right?
[00:01:23] Joe: Feels so right. Well, we’ve got a great- She loves you
[00:01:27] Doug: all the time.
[00:01:28] Joe: We’ve got a great show for you, Stackers. We’ve got some phenomenal people on the show today who may have made some bad money moves that they had to unlearn, and we’re gonna hear all about those. Let’s start off with the gentleman across the card table from me, Mr.
[00:01:44] Joe: OG. And speaking of, speaking of food, and not ice cream, he’s on- Well- … is it a burrito or a Pop-Tart?
[00:01:52] OG: Well, well, it’s, it’s kind of a little bit of both here. So what we have here, m- my wife will make a cake, you know, for whatever, a birthday or something, but we just don’t go through it. We just can’t eat the whole thing.
[00:02:03] OG: So she cuts it up in little bite-sized pieces like this and, uh, freezes them, individually wrapped. So I have frozen cake that I’m eating- Frozen cake? … right now. So-
[00:02:12] Doug: Crunchy cake?
[00:02:14] OG: I mean, it kinda thaws pretty quick as you sit here and hold it. But-
[00:02:17] Joe: Welcome to the, uh, Martha Stewart, uh-
[00:02:20] OG: This is… Don’t knock it until you try
[00:02:22] Doug: it.
[00:02:22] Doug: A little- You’re not eating fast enough.
[00:02:23] Joe: I’m not knocking it. I’m just, uh… Y- yeah, we’ve become a food preparation show very quickly. And a woman, oh my God, she’s eating too. I can see her backstage already. And Manhattan Paula Pant, what is the deal? Did you guys decide that this is, like, our community, uh, eating- Well, I think-
[00:02:40] Joe: fest? Get together …
[00:02:41] Doug: Paula’s just drinking cake batter, is what
[00:02:43] Joe: it looks like. She is drinking cac- uh, cake batter, and she’s on mute, thank goodness. ‘Cause while we can hear OG chowing away-
[00:02:49] Paula: Ah …
[00:02:50] Joe: we, uh… OG maybe should be on mute.
[00:02:52] Paula: Well, this is, this is what happens when you host a show at lunchtime. This is macadamia milk, arugula, peanut butter, and banana.
[00:02:59] Paula: You lost me at arugula. Arugula? Why? Peanut butter and banana?
[00:03:05] Joe: What?
[00:03:06] Paula: Uh, well- Who would do that? I ran out of spinach, so, you know. Where is
[00:03:10] OG: the nipple on the macadamia to come up with, uh- … macadamia milk?
[00:03:14] Paula: I, I think they just soak it for a long time and then squeeze it.
[00:03:17] Joe: Oh, damn. I don’t…
[00:03:19] Paula: We just-
[00:03:19] Joe: Oh, we’ve devolved already. Come on. The guy who’s wondering- Come on … what the heck, w- w- what the heck he’s- How am I supposed to
[00:03:26] Doug: let that go?
[00:03:28] Joe: I’m, I’m trying to, Doug. We’re trying to. Guy that wonders what the hell he’s doing here, he is the longtime host of a show that you know very, very well if you’ve been a money fan for a long time. That is Motley Fool Money. But now he’s got bigger, better, cooler things. He’s the host of Money Unplugged.
[00:03:48] Joe: Chris Hill joins us. How are you, man?
[00:03:51] Chris: I’m well. I’m loving the spectrum of health that we’ve already hit here. We’ve gone from a- arugula to cake and, uh, and, and really it’s, uh, it’s what makes America great. And tequila.
[00:04:03] Joe: Don’t forget that.
[00:04:04] Chris: And the tequila. We’d never forget the tequila. And- Meanwhile, I’m just-
[00:04:07] Chris: and, and
[00:04:07] Paula: electrolyte water.
[00:04:08] Joe: Oh my goodness.
[00:04:08] Chris: I’m just here with a, a boring can of seltzer.
[00:04:11] Joe: Oh my goodness. What type of seltzer is that?
[00:04:13] Chris: Uh, I, I don’t know if this is an official plug, but it’s Waterloo. Uh, is the brand
[00:04:19] Joe: Oh, Paul, Waterloo’s not the one we were talking about before. That was Spindrift
[00:04:22] Paula: It, uh, uh, begins with an S and- Yeah, Spindrift
[00:04:25] Paula: rhymes with Mindrift
[00:04:26] Joe: Yes, right. Right. And I’ve got Basic Water. But Chris, for the four people that don’t know about your awesome show, Money Unplugged, let’s call it Money Plugged. Let’s plug the Money Unplugged show. What’s it all about? What do you do?
[00:04:40] Chris: As you said, for a long time I was the host of Motley Fool Money and, uh, MarketFoolery, which was a daily podcast at The Motley Fool for many years.
[00:04:47] Chris: I loved digging into the stock market every day and, and the news that, uh, was coming out of Wall Street. But when I left The Motley Fool a few years ago, I, I got more interested in the psychology of money, sort of the emotional side of money. And so Money Unplugged is a show where I talk to people about their relationship with money, starting with what do they remember about it as a kid, what was the first job they had as a kid, and how that relationship with money changes as we get older.
[00:05:14] Chris: Because one of the things that I’ve discovered as I’ve had these conversations over the past year and a half of doing Money Unplugged is that- Money leaves an indelible print on our lives when we are kids. Sometimes that’s a very positive thing, sometimes it’s a negative thing. Uh, whether it’s positive or negative, it, it, that imprint never fully goes away.
[00:05:38] Chris: So it’s really been great to talk with people about sort of what their relationship with money has been like over the years, mistakes that they’ve made, and the end of every interview is a speed round of lighter questions, uh, about fun things, like splurging. ‘Cause come on, who doesn’t love to splurge every once in a while?
[00:05:56] Joe: And it’s fun to hear some of your favorite money personalities and how they like to splurge.
[00:06:01] Chris: How they like to splurge, and regrettable purchases that they have made. There have been some pretty epic answers, uh, in terms of what, what’s a purchase you’ve made in your adult life that you regret?
[00:06:11] Joe: Well, I thought, Chris, we would take a page out of your playbook, ’cause I wanna talk about that today.
[00:06:15] Joe: I’ve heard on your show so many of my favorite personalities talk about money mistakes they’ve made, and I thought today we’d use that as our theme. What are some of the things, what are some of the money habits that we have to unlearn? And I can’t wait to hear all of your answers to that. So that is the topic, everybody, for today.
[00:06:34] Joe: We’re gonna surf on into today’s discussion, today’s show sponsored by Surfshark. If you’re like us, you’re spending a lotta time online right now watching, uh, SpaceX stock. Paula, are you watching SpaceX stock?
[00:06:46] Paula: Uh, I checked in on it the day after the IPO, and since then I’ve totally ignored it.
[00:06:51] Joe: Well, good, ’cause my next line was gonna be, “Turn that stuff off.”
[00:06:54] Joe: Like, stop that. Watching talking heads talk about SpaceX stock, or maybe, uh, hopefully instead looking at, uh, the Detroit Tigers maybe beginning to win some baseball games again. It’s much better to focus on that. But while you’re doing all that, your data’s basically out there for anybody to grab, and that’s where Surfshark comes in.
[00:07:11] Joe: Surfshark is a VPN that encrypts everything you do online, so whether you’re working on Stacking Benjamins at home, at a coffee shop, or scrolling your broker’s account on airport Wi-Fi, your info stays private. Think of it like having an insurance policy before you step onto the internet. You’re protected.
[00:07:27] Joe: Here’s one thing I really like. One account covers unlimited devices, so your phone, your laptop, and your smart TV, everything is locked down. Hate all the pop-up ads on web pages? Features like CleanWeb block ads and malware before they even hit your screen. So if you wanna browse smarter and maybe even find better deals on travel or online marketplaces by changing your v- virtual location, check it out.
[00:07:47] Joe: Go to surfshark.com/stackingbee, or use code stackingbee at checkout and you’ll get four extra months of Surfshark VPN. That’s surfshark.com/stackingbee, code stackingbee. All right, we have another sponsor who helps us keep on keeping on. We’re gonna hear from them, and then Chris, Paula, OG, Doug, and I, we’re gonna get into, uh, some money mistakes that we had to unlearn.
[00:08:19] Joe: Let’s set this up. Talking about money beliefs we have to unlearn, all of us, and Chris, you said this pretty eloquently, right? We all inherited financial wisdom from somewhere. You talk about the early days, but also there’s our parents, our first boss, financial gurus, maybe even that weird uncle who always had opinions about gold.
[00:08:37] Joe: I think we all have or, or, or your cousin who loves, uh, crypto, whoever. We’ve all got these beliefs. Some of them serve us, some of us don’t. So Chris, I’m gonna start with you ’cause you asked me this question. You ask people every week this question on your show. What’s the first money lesson you remember learning?
[00:08:55] Chris: The first money lesson I remember is, um, learning about the concept of being cheap, and I don’t mean frugal. I’m talking about being cheap. It was something that my dad imparted to me. I was a kid, maybe I was eight years old, nine years old or something like that, and he just sort of sat me down and explained there’s a difference between saving money, being smart with money, and just being cheap.
[00:09:23] Chris: That was something that just sort of always stuck with me, and there’s certainly been times in my life when I’ve been smarter about money, saving and investing, a- and spending, than others, but I’ve tried very hard. That’s, that’s a lesson that I had when I was a kid that stuck with me, just like, j- just, just don’t be cheap.
[00:09:42] Chris: Just don’t- … just don’t be a s- any of the other, you know, terms that go along with that. I’m not gonna break out the thesaurus, but I think everyone knows, like, when you’re being cheap and when you’re not, and that’s one. Like, most of the other lessons that my dad tried to impart to me about money, yeah, they went in one ear and out the other, but that one stuck with me.
[00:10:00] Joe: It is wild that that one’s the one that stuck with you. My roommate in college w- we had some incredible discussions about how he grew up with that same thing, and he was always fighting that. I gotta try not to be cheap. Paula, you and I have talked a little bit about your background and this. Did you grow up with any of that, having to fight being cheap?
[00:10:19] Paula: Well, first I was gonna ask Chris, what’s another word for thesaurus?
[00:10:27] Joe: She’s here all week, folks
[00:10:28] Chris: No idea Here all week I’m stumped. I’m out. If the trivia question is any harder than that, I’m out.
[00:10:34] Paula: We didn’t really talk about cheap versus frugal, but we were just always hyper frugal. Like, my earliest childhood memory is being with my mom going to these three different grocery stores because bread was cheaper at one, and milk was cheaper at the second, and bananas were cheaper at the third. And she’d sit at the kitchen table, and she’d clip coupons out of the, the newspaper.
[00:10:57] Paula: Like, you know, the big Sunday edition has all the coupons. Oh, yeah. Right. Right? So she would sit there, and she’d clip all of the coupons, and that would take a few hours. And she’d have these different stacks on the table of different coupons for different stores. And then we’d spend the whole day, I mean, it was an all-day thing, just buying groceries.
[00:11:14] Paula: ‘Cause it w- it would require going to so many different stores with specific lists for specific things and then specific coupons for each one, and it was… So I learned that to be good money management. There wasn’t any discussion around is that frugal versus cheap. That was just, that was just the norm.
[00:11:34] Joe: There was no real difference. I mean, it was frugal is-
[00:11:37] Paula: I mean, we didn’t even really think of ourselves as frugal per se because, I mean- It was
[00:11:41] Joe: just what you did …
[00:11:42] Paula: yeah, ’cause to identify as frugal kinda assumes that there are other people who are spending more than you, and we never really had that assumption ’cause we just didn’t have that frame of reference.
[00:11:51] Paula: We didn’t know people who spent a lot of money. So this was just, like, how you bought groceries
[00:11:57] Joe: OG, what about for you? Earliest money memory?
[00:12:00] OG: It’s funny. It sounds like Paula’s mom and my mom went to the same school of how to get groceries. But the lesson that I got out of that wasn’t the same as yours.
[00:12:09] OG: Mine was, “This absolutely sucks, and I need to do whatever it takes to not have to do this.” Because the- Well, it’s funny
[00:12:15] Joe: because Paula, you’re, you’re very famously- Yeah … like against that activity.
[00:12:18] Paula: Yeah, yeah, yeah. But it took me a long time to get there. By the time I got to my late 20s, early 30s, I figured out exactly what OG just said.
[00:12:28] Paula: Yeah.
[00:12:28] OG: Yeah. That sucks. That’s a awful waste of time. Um, that was a little strong. It’s not a huge waste of time ’cause you can get some value out of it, but time value
[00:12:37] Paula: of- It’s, it’s
[00:12:37] OG: a big waste of time … you know, experience- Yeah … is-
[00:12:39] Paula: Yeah …
[00:12:40] OG: is not what I would wanna do. You know, my financial childhood was a little two-sided in the sense that everything that I experienced in my close home, like my mom and dad always struggled with money.
[00:12:52] OG: There was never enough. Didn’t matter how many hours Dad worked. Somebody was getting screwed somehow because the boss was a jerk or so- There’s always some story that went with that, and that just was kind of that side of the family. And then my grandparents on the other hand, were entrepreneurs, and Grandma and Grandpa always had money.
[00:13:10] OG: They always were the ones that if you needed something, you could… You know, they’re, the stories from, you know, the cousins and whatever would cycle down, and it’s like, “Well, you know, Grandma and Grandpa helped me get my first car. They helped us get our first computer. They helped…” You know, there was always something at Grandma’s house that you could go back to.
[00:13:27] OG: And I don’t know if that set the stage for be in control of your own life and be in control of your own money because that gives you flexibility, and you can, you know, you can do what you want and help people that way, or if it was the lesson like, “This way of doing things kind of sucks. I should probably see something different.”
[00:13:42] OG: But I very early started working. I was 11 when I started my paper route. I think the bad lessons that I had out of that were that the money that I got, while I, I saved some, and I certainly saved enough to purchase my car when I was 16, you know, a used car when I was 16. I spent a lot of the time and energy on improving my own personal lifestyle, you know?
[00:14:08] OG: Like in the sense of like, well, I wanted the better clothes. The only way to get that was if I paid for it.
[00:14:13] Chris: Hmm.
[00:14:13] OG: If I wanted the new Nikes that were out, I had to pay for them because there was no way that I was getting the new stuff, you know, at the department store So I think I maybe learned very early to kind of like look after myself and like if I want something, I gotta do it on my own.
[00:14:29] OG: Maybe that was the lesson.
[00:14:30] Joe: It’s interesting how
[00:14:31] OG: you- But there’s a big downside for that. There, there has been. Yeah.
[00:14:34] Joe: Right. Right. I mean, you just look at entrepreneurship as success, and look at how many entrepreneurs have gone out of business, have learned, you know, have, have really struggled. I wanna talk about some of these money stories that we inherited, and Chris, again, we’ll start with you because you’ve spent years interviewing successful investors and business leaders.
[00:14:52] Joe: What’s a money belief that you’ve seen really successful people hold that really isn’t true?
[00:14:58] Chris: That really isn’t true? Oh. You know, particularly when it comes to Highly successful entrepreneurs, I think, um, a mistake that is made by the financial media and a lot of people, and I’ll, I’ll include myself in that, is there’s a tendency to want to attribute brilliance that has been earned in one area to all things.
[00:15:24] Joe: Oh,
[00:15:24] Chris: yeah. Um, so it’s like, hey, this person started this company, um, took them public. This person’s a billionaire. Every idea they have must be brilliant, and it’s like maybe or maybe… L-like to, to me, a, a better example is, like, Mark Cuban, where, like, Mark Cuban is, is pretty willing to admit that he kind of caught lightning in a bottle and that’s how he got to be a billionaire.
[00:15:48] Chris: He, like, he made some smart decisions early on, but he doesn’t strike me as someone who’s like, “Every idea I have is brilliant,” even though he gets asked about sort of all different things. The example I always use is Albert Einstein. It’s like, yeah, Albert Einstein is a genius. Um, you wouldn’t want him performing heart surgery.
[00:16:04] Chris: He’s not that type of genius. I don’t know that that actually answers your question, Joe. I mean, maybe it has more to do with just sort of like people who are hyper successful having a, an extreme level of confidence, which you kind of have to do if you’re an entrepreneur. There is absolutely a fake it till you, you make it mentality that Thomas Edison had and, and sort of every entrepreneur since him.
[00:16:26] Chris: Yeah. So you need that. I think where people get into trouble is to just… when they don’t have guardrails around them, whether that’s family members or executives who are willing to stand up to them. I think that’s where they get into trouble.
[00:16:41] Joe: Well, and that’s interesting. So maybe it’s not the most successful people, but maybe the next tier ’cause I’ve seen, Chris, a lot of people who were moderately successful, fairly successful, and that success became an ego that got in their way ’cause they thought, “Because I was smart in this one area, I was smart about everything.”
[00:16:56] Joe: Yeah. As you’re talking, I’m… I, I started thinking of specific times, which means that it’s so important to surround ourself with, you know, not yes people, but people that are gonna kind of be Gordon Ramsay in our corner, don’t you think?
[00:17:09] Chris: Absolutely. Absolutely. Um, the example that leaps to mind is a video I saw recently of, of Bill Hader who was on SNL- Oh, sure.
[00:17:16] Chris: Yeah … all those years and, and created the show Barry and, and, uh, on the show Barry where he is the writer, director, executive producer. You know, it’s his show. He’s the star of the show. He’s also the showrunner, and he talked about how when he would show up on set, there would be this, like, murmur just like, “Oh my God,” like, you know, “Bill’s here.”
[00:17:34] Chris: You know, “Everybody be on your best behavior.” But one of the people who worked on the show is a friend of Bill Hader’s that he’s had since they were teenagers together growing up in Tulsa, Oklahoma. And that was the guy who would just tell him like, “No, you didn’t.” You know, so there was an episode where Hader is directing it, but he’s also acting in it, and he does his first take, and he thinks, “Oh, I’ve totally nailed this.”
[00:18:00] Chris: And then his buddy comes up to him and just goes, “I don’t know, seemed like you were doing a lot of acting.” And he’s like, “Wait, what are you talking about?” He’s like, “Eh, it’s your show. You do what you want. I don’t, I don’t know. It just seemed like you were doing way too much acting.” And so I just think like, yeah, we all need that friend.
[00:18:14] Chris: We all need that friend who’s not impressed with us for what we’ve achieved. They’re willing to tell us the truth.
[00:18:21] Joe: Well, Chris, you were here with us backstage, and we had that murmur with Doug came in the room. I mean, the second- Yeah … you know, Doug’s here. Everybody watch out. Yeah. Um- He’s gonna
[00:18:28] Doug: tell you exactly what he thinks.
[00:18:30] Joe: He will tell you exactly what he thinks. Actually, it’s funny. In the creation of this show, Doug’s been that guy for a long time. Has, has been the guy going, “Yeah, I don’t think you should’ve had that guest on.” I remember the early days, Doug. You’re like, “Why, why you talking to that person?” Like, I don’t- Careful,
[00:18:43] Doug: Chris.
[00:18:44] Doug: I might say that after this show. I’m, I’m counting on it, Doug.
[00:18:49] Joe: He’s praying for it, right? Paula, you’ve got the coupon clipping that you inherited that you were able to shake, but were there any other inherited beliefs that you had that you’ve had to shake?
[00:19:01] Paula: This kind of goes hand-in-hand with coupon clipping, but it, it’s the unstated underlying premise behind it, which is that your time is not worth anything.
[00:19:11] Joe: Mm.
[00:19:11] Paula: Like, that, you know, the value of an hour is zero. And so if you can save money during that hour, that is better than not, regardless of the amount that you save. You know what? I, I think it was a very… I’m gonna call it like a salary mentality, and I don’t mean that as a, a dig on people who get salaries ’cause it’s not about the salary itself, it’s about the mindset.
[00:19:32] Paula: It’s like a, a fixed mindset, right? So it’s a mindset of like this is a fixed pool of money that comes in. Given that this is a fixed pool of money that comes in, the objective is to save as much of it as possible, and there’s zero thought given to how to make more because the mentality is this is the fixed pool and, and we’re, we’re just…
[00:19:55] Paula: Uh, it’s sort of a ceiling mentality,
[00:19:57] Joe: right? It’s inter- Yeah. You’d have, you’d have learned to think blue sky.
[00:20:00] Paula: Yeah, exactly. I had to learn to think blue sky instead of floor, or instead of… Yeah.
[00:20:05] Joe: Yeah. While we’re talking about this, OG, I’m, uh, I’m just thinking about these different money, quote, “rules” that people have that sound smart but don’t really survive the contact to real life.
[00:20:16] Joe: You also run into people in your meetings that maybe have these money rules in their head. Can you think of a money rule offhand that doesn’t really survive the, you know, the sniff test? Sounds great. Yeah, sounds cool, but eh.
[00:20:30] OG: Uh, well, I have two answers for this. One is the answer that, uh, to the question that you gave everybody else, which I was ready for.
[00:20:37] OG: And one answer is for a different one that I’m trying to come up with right now as I- Would you rather
[00:20:41] Joe: I answer-
[00:20:42] OG: As I- Would you
[00:20:42] Joe: rather
[00:20:43] OG: answer that one first? … you know, stretch, stretch. Um, you know, I think there’s a very big belief system around a couple of things. One is, is that in order to get ahead you have to take obscene amounts of risk or volatility, variability in your life.
[00:21:01] OG: And the, the way that that manifests itself, I’m saying this a little differently than what people will say, but you have to use a lot of leverage. You have to lever a lot of things, whether that’s borrowing a bunch of money because that’s the only way that you can, you know, deploy capital, and, you know, other people’s money, OPM, the Rich Dad Poor Dad type of concept.
[00:21:19] OG: Whether it’s on real estate, whether it’s on, uh, I mean, even kinda leveraging your life or your experience and saying, “You know, I’m gonna try to, try to go to get this job or go to go to this school to get this education. It costs three times as much as this other education, but because I got this paper, it sh- should pay off a different way than, you know, going to the community college or state college or something like that.”
[00:21:40] OG: Just making an example. Um, and sometimes that does pay off, but a lot of times it doesn’t. And for me- Um, I had to kind of go through that trial period, which lasted, I don’t know, 48 years and some change as, as I’ll be 49 later this year, of recognizing that, A, you don’t have to take unusual amounts of, of risk in your life to get a payoff.
[00:22:03] OG: Boring, slow, and steady stuff really works over a long time. The problem is, is we don’t get to see it in real time. And so since you don’t see it in real time, or God forbid, you see everyone else, especially on, uh, social media, on Reddit, on Instagram, living the life that you wish that you, or that you think that you should have, and, you know, why is it that that person gets to have that and I don’t?
[00:22:26] OG: Well, it’s because they, they did this thing. And, and whether it was luck or they, you know, used some form of, uh, chicanery to get into, you know, their success or whatever it is, there’s always some story behind it, when in reality, slow and steady really pays off over a long period of time. And the other side of that is you have to enjoy the experience of what you’re doing.
[00:22:49] OG: And so if you’re moving toward, let’s say, financial independence, we’re talking about money on Stacking Benjamins, so we’ll tie it to financial independence. Financial independence is not a number, and I don’t know how many times people have to experience this, or maybe it’s just I have to experience it through other people to get this drummed into my own skull.
[00:23:09] OG: But it’s not like as soon as I get to three million, phew, all the problems of the world disappear. It is just, just mai tais and beaches from that point forward. And that’s not what happens. And we– that’s never happened. But for whatever reason, we have these-
[00:23:25] Joe: Wait a minute … breakpoints
[00:23:26] OG: in our life.
[00:23:27] Joe: So happiness, happiness doesn’t come when you get to 25 times your annual expenses?
[00:23:31] Joe: That, that all of a sudden unicorns and rainbows don’t appear?
[00:23:33] OG: I mean, it, it sounds like it would be when you’re not there, right? It sounds like, you know, “If I could just make a little bit more money, or if I could have just a little bit more net worth, or if I could have just a little bit better school system for my kids, or maybe if I could get into that one job that I’m trying to get to, then everything else would be fine.”
[00:23:52] OG: But all of us have had this experience, and I would just challenge you to think through it. Like, all of us have earned one tenth of what we earn today. Every single person, I mean, barring a 17-year-old listening, right? My first job, when I worked as a paper boy, s- I told you I started at 11. My first year, I made $1,700.
[00:24:11] OG: I have 10 times that to 17,000, and I’ve 10 times it again to 170,000. And I can tell you that every step of the way, and I think everybody here would agree with this, there was a point somewhere in there like, “Man, I’m making 50, but if I can make 75, whew, everything is perfect in my life. I make 100, but if I could make 200, then finally I can get my lips above water.”
[00:24:32] OG: But none of that is true. If you don’t have the right systems- Mo’ money and mo’
[00:24:35] Doug: problems.
[00:24:37] OG: Doug, stop being succinct. I’m trying to fill up air time. Um- Oh, God. I’m trying to hear myself talk, damn it. You know, if you don’t enjoy the journey, if you don’t enjoy what you’re doing or who you’re doing it with, like it doesn’t matter how much frigging money you have.
[00:24:52] OG: Like, it-
[00:24:53] Joe: Well, and that is… No, and that is interesting because I think there’s some of these things that we were adamant about when we were younger that we’ve had to kind of unlearn and maybe back away from, like unicorns and rainbows appear. Like I often when I see people new to the FIRE movement, they’re so excited because there’s going to be in the future, “If I sacrifice my entire life today and it’s miserable, it’s gonna be incredible later on.”
[00:25:14] Joe: And just patently-
[00:25:15] OG: I saw
[00:25:16] Joe: this- … generally not, not true …
[00:25:17] OG: I s- I, I saw this, uh, video the other day that I thought was really interesting, kind of ties into this. It said something along the lines of, “In 30 years from now, you would give every dollar of what you have 30 years from now to go back in time to where you are today.”
[00:25:33] OG: You know, I was like, “Yeah, that’s probably true actually. I betcha, I betcha when I’m 79, I’d be like, ‘You know what? I would give everything to go back to being 49.'” And I bet we would say the same thing about… Well, maybe not 19. That was kind of a tumultuous year, but 30-something would be pretty sweet to kind of go back in time to.
[00:25:51] Joe: Chris brings up something hanging out with us here on YouTube. We generally record these Monday afternoons. If you get the 201 newsletter, we always, uh, send out a, a reminder of what time it’s gonna be, but come join us on Mondays. But Chris hanging out with us says, “Happiness is a lot easier though once you get the breathing room, right?
[00:26:07] Joe: At least from my standpoint. Doesn’t fix all
[00:26:09] OG: the problems- Yeah, I would agree with that completely. Yeah …
[00:26:11] Joe: yeah, but it does open up so much more flexibility, including beaches and Titos.” I like how he, he picks, picks two very specific things there, Chris. But I’m wondering if there are some of these adamant beliefs, Chris, that you might have had when you were younger that maybe, to OG’s point, you’re not as adamant anymore on.
[00:26:28] Joe: You know, maybe you didn’t need to unlearn, but you’re like, “Uh, this might not be as hard and fast rule as I thought it used to be.”
[00:26:34] Chris: Oh, absolutely, particularly in my investing life, and, uh, I started investing in the ’90s, um, and sp- more specifically in individual stocks in 1997. And a, a steadfast belief that I had at the time and held way longer than I should have is the idea that dividend-paying stocks are for old people.
[00:26:58] Chris: Hmm. That dividend-paying stocks are for people who are in retirement or about to retire. Uh, companies that pay dividends only do that because their best days are behind them. They don’t have any ideas to do… You know, for what else to do with the money, and they’re certainly not innovative. I held onto that belief for probably the first 20 years of my investing life.
[00:27:21] Chris: The big crack in that belief actually came in 2012 because one of the stories going around in the financial media in 2011 and 2012 was the amount of cash that Apple held on its balance sheet as the iPhone was taking off and Apple was just piling up all this cash. And for, I would say, 12 to 18 months Whenever Apple came up, certainly when they came out with their earnings report, a discussion that would be held on CNBC and Bloomberg, and certainly the…
[00:27:56] Chris: I’m guilty of this as well, the podcast that I was hosting at the time, was this question: Is Apple gonna pay a dividend? And if Apple does pay a dividend, what does that mean? What does it mean, Joe? Does it mean their best days are behind them?
[00:28:08] Joe: Right.
[00:28:08] Chris: They slowing
[00:28:09] Joe: down. Are they gi- They slowing… No, no longer growth
[00:28:10] Chris: company.
[00:28:11] Chris: Right. And there were- They’re out of ideas … there was, there were people pounding the table saying, “They can’t pay a dividend. It’s outrageous.” They would be giving up. It’s like they would’ve crossed this bridge to the land of dividend-paying stocks, and you can never return from that. And in early 2012, uh, new CEO Tim Cook announced that in fact, Apple would begin paying a dividend.
[00:28:31] Chris: They started paying it, I believe, in August of that year. And, uh, the world… Not only did the world not end, but that topic of, that firmly held belief, that narrative of companies that pay dividends are not innovative and, uh, dividends are just sort of for people who are about to retire, it really started to melt away.
[00:28:54] Chris: And that’s when I just started to think, “Well, wait a minute.” Um, should I be buying some of these co- You know. And I j- I checked this morning. Of the 10 biggest holdings I have now in 2026 in terms of individual stocks, eight of them are companies that pay dividends. And I try very hard to be grateful for where I am in my life and how I’m doing and my health and all those things because if I wasn’t doing that, Joe, I would look back and I would actually spend time trying to calculate how much money, how much more money would I have had if I had bought some of these amazing companies that also just happen to pay dividends sooner rather than later.
[00:29:39] Joe: It’s interesting, Chris, ’cause as you’re talking, I’m thinking, you know, the past 15 years, really what you’re talking about is also what venture capitalists have been doing. ‘Cause they go into these staid, older industries, these quote dividend-paying backlot industries, and they c- they clean ’em up. They find efficiency where there may not have been efficiency.
[00:29:56] Joe: They find growth in these areas by, you know, bringing them to the current times instead of being behind the times. It’s, it’s really interesting. Paula, is there a similar belief that you’ve reversed yourself on or maybe backed down from?
[00:30:15] Joe: That’s a no
[00:30:15] Paula: I, but You know, on the topic of individual stocks, I used to be all like avoid individual stocks, only mutual funds and index funds. Or initially I was thinking only mutual funds and index funds, and then later refined it to only index funds. And now I have an openness to a contained portion of a portfolio containing individual stocks if you do proper due diligence on it and understand how to look at publicly traded companies, and you have s- guardrails and parameters and all of that around it.
[00:30:54] Joe: I, I think it’s funny because for me, having a few individual stocks helps me with my investment policy statement to stay in place. It keeps the excitement up in investing. I don’t know. Oh. I’m a guy that, y- you know, and I know that boring is generally better, but just going into my Schwab account and looking at my few individual stocks just makes me, you know, get excited about the investing train.
[00:31:17] Joe: OG, how about you? Something that you were adamant about early in your career that maybe isn’t the big hard and fast rule you thought it was early on?
[00:31:25] OG: No, I can’t think of any. Pass.
[00:31:28] Joe: You do have one. I know- Then tell me … I know one working with you for the last, um- Busy. I’m out of ideas … don’t pay off your mor- uh, uh, don’t go with a 15-year mortgage.
[00:31:36] Joe: There’s one
[00:31:36] OG: you’ve changed on. Yeah, I mean, I do think that I, I personally have changed it, but I’m not sure. I don’t re- I was thinking about that one, but I don’t remember what I used to tell people or believe in myself. I probably believed the, you know, invest the difference of the 15 and that sort of thing, and…
[00:31:54] OG: But I think just dealing with it on my own, what we’re talking about here is should you have a 30-year mortgage and have a low interest, low payment for, you know, 30 years, or should you have a 15-year mortgage and get it paid off faster? And you’d say, “Well, you know, the math says that you should have the leverage, and even if you save the difference,” and yada, yada, yada.
[00:32:13] OG: But I just never saw that working in practice. Like, I never saw anyone save the difference, nor did they get to that 15th year and go, “Hey, so I saved the difference between the 15-year payment and the 30-year payment, and now I’m 15 years into my mortgage, and I’ve accumulated this pile of money. I’d like to pay off my house now.”
[00:32:31] OG: No one has ever done that, to my knowledge. I’ve never met anybody. I’ve never talked to anybody who’s done it that way. Um, I’ve never- It actually is interesting … witnessed
[00:32:39] Joe: it. Uh, people that have been fans of the show for a long time haven’t heard this before ’cause you and I haven’t talked about this in a long time, but I used to help people do that.
[00:32:47] Joe: We’d figure out the pay off the house early number, take out the 30 year. Sure. We’d invest the difference, but every single person, to your point, OG, when they got to the point that there was enough money there in that fund to pay off the mortgage, nobody ever did it. But it was also just the freedom. They wanted to know they could do it at any point.
[00:33:04] Joe: It wasn’t necessarily the, you know, “I need to pay it off now.” They felt so much more comfortable that they could pay it off now because they had this separate pot of money sitting there.
[00:33:15] OG: I mean, I, I get the math argument, and I guess if you can execute it perfectly, it would work out amazingly across the board.
[00:33:23] OG: But then I would just ask you the same question, and I’d just spin it on its head and say, “Then why don’t you continually refinance your house and top off the loan?” Yeah. Like, why would you make any progress on it ever? And furthermore, why would you continue to do that only with your mortgage and not do that with your investment account?
[00:33:39] OG: Schwab will let you buy… You know, if you have a million dollars in your brokerage account, they’ll let you buy $2 million worth of stock. Hell, sometimes they might let you buy six or seven million, depending on your status and, like, you know, and how, if you can pass an options test or go online to figure out the answers and then pass it.
[00:33:54] OG: They’ll give you the leverage y- all, all you want. But we never do that side of it, and I go, “Why is that?” Wh- why wouldn’t you do it with the biggest 500 companies in America, but you’re gonna do it with one single house in the middle of nowhere, Texas? Like, I just… It doesn’t make any sense to me that you would apply that logic in one side and not in the other.
[00:34:11] OG: I think that’s just a belief system that we, that we all have, that it’s safe to do it with your mortgage, not safe to do it with, you know, with other things. Safe to do it with a commercial property, but only once. You know, y- do it with your… Do it to get in, but as soon as you can get the tenants to pay that mortgage off, that’s a good thing.
[00:34:28] OG: I, I hear people talk about doing it. I don’t actually see it happening in reality.
[00:34:31] Joe: See it happening, yeah.
[00:34:32] OG: You know.
[00:34:33] Joe: After the break, we’re gonna play a little mini version of our game In or Out. I’m gonna give you some financial concepts, some of these ideas, and you’re gonna tell me if you’re in on this idea or out on this idea.
[00:34:44] Joe: So you guys get ready for that. But we always pause, and today it’s gonna be a little after halfway through the show, but, uh, we pause for our year-long trivia competition where, uh, frequent contributors Paula, Jesse, and OG duel it out to see who can get the most wins. Chris, you’re playing Team Jesse Cramer today.
[00:35:03] Joe: Mm-hmm. So you’re helping Jesse, which means we’ve got some good news for you, my friend, and some bad news. Which one would you like first?
[00:35:10] Chris: Always lead with the bad news.
[00:35:12] Joe: Well, the bad news is you’re not winning. You are the defending champion, so you’re on the defending championship team, but, uh, you are in second place.
[00:35:19] Joe: And Doug, what’s our score here as we creep up on the halfway point?
[00:35:23] Doug: Starting to get interesting here at the halfway point, Joe. We have OG in the lead with nine points, Jesse, or as it were Chris today, in second place with six points, and Paula with three points.
[00:35:37] Joe: We were talking about earlier about OG making a run at the top number competition, which has been- The record, yeah
[00:35:43] Joe: 18 is the record, yeah. But now, uh, Chris, no pressure, but you and Jesse are, uh, taking a run at him. And someday, maybe 2028, 2029, Paula will start taking a run too. We’ve been saying that for what, Paula, a decade?
[00:35:57] Paula: Maybe we need to open up, like, a Kalshi poly market kind of a thing on this. You know? Like, who’s-
[00:36:03] Joe: Can Paula actually- Like, which-
[00:36:04] Joe: win this Friday trivia?
[00:36:06] Paula: Right, right. I’m not sure. Well, and, and which one’s going to be the year? ‘Cause, because whoever actually bets on my winning year is gonna make out big on that one.
[00:36:14] Joe: Right. The Kalshi odds on that would be, like, 50 to 1 now. I mean, you’re just keep-
[00:36:18] Paula: Yeah.
[00:36:18] Joe: Maybe that’s what you do- maybe you should play in the long game, Doug.
[00:36:21] Joe: I don’t know. Yeah.
[00:36:23] Paula: This is how I’m gonna pay off that mortgage.
[00:36:26] Joe: All right. All right, well, here we go. Will Paula be able to pay off the mortgage this week? Is Chris gonna help Team Jesse creep up on OG, or does OG get one step closer to the record? Well, Doug, you’ve got the question.
[00:36:41] Doug: Hey there, Stackers. I’m Joe’s mom’s neighbor, Doug, and by now you all know I’m a pretty big fan of the game of baseball, and not just because one of the official rules of baseball, specifically rule 702 subsection A1C, is that a fan obligated to eat as many hot dogs as possible over the course of nine innings.
[00:37:02] Doug: And because I know you’re all wondering, my average is 22. Don’t worry, I do it the right way, mustard only. Another reason June 19th is a big day in baseball is because it’s thought to be the date the very first game was played under the modern rules, known as the Knickerbocker Rules, way back in 1846.
[00:37:20] Doug: But it’s really none of that because it’s also the birthday of the all-time great, Lou Gehrig. So here’s today’s question if you’re not already asleep. When Gehrig when Gehrig’s 2,130 consecutive game streak ended in 1939, Americans were still climbing out of the Great Depression. So adjusted for inflation, if you earned Lou Gehrig’s 1939 salary today, how much would it be worth in today’s dollars?
[00:37:52] Doug: I’ll be back with an answer right after I go tell Joe’s mom to add hot dogs to the grocery list. We’ve only got a few dozen in stock.
[00:38:02] Joe: A few dozen’s enough to last Doug about three days, so we’ve got some more work to do there, Ma. OG, it’s on you, man.
[00:38:11] OG: Is it, so the information given was 1939 and today. Those are the two data points- That is it. Yep … what we have to work with. Uh, so 1939 till present is 190, 83-ish years. Is that right? So 83, um, inflation 3%.
[00:38:37] OG: I don’t think baseball players are paid very much. So this is his 1939 contract, Doug?
[00:38:43] Doug: Yes, in
[00:38:43] OG: today’s dollars. Adjusted for inflation. His, just not, not the, not the full value of his earnings, but just the 1939 season.
[00:38:51] Doug: He did have a Malto Meal, uh, sponsorship contract. So we’re not counting that.
[00:38:56] OG: We’re not counting that.
[00:38:57] OG: This is just straight baseball pay. I’m gonna say that that would be worth the equivalent of… I got two numbers in my brain right now. I’m gonna say $319,242.71.
[00:39:14] Joe: 300- or, or roughly $319,000? Is that what you’re saying?
[00:39:18] OG: Uh, I, I said what I said.
[00:39:21] Joe: Ish. I don’t even remember the rest of that. So Chris, we got- Messing,
[00:39:24] OG: messing with Doug.
[00:39:26] Doug: We got- I know he is, but I’m way ahead of him. I have technology working for me.
[00:39:31] Joe: Chris, we got 319,000-ish as our first guess. Uh, what do you think?
[00:39:36] Joe: Lou Gehrig in today’s dollars.
[00:39:39] Chris: I’m trying to remember the money involved in the, uh, the famous quote from Babe Ruth, obviously Lou Gehrig’s teammate, when, uh, Ruth was the highest paid player in the league. I don’t remember how much he was paid, but someone said, “You know, you’re making more than the President of the United States.”
[00:39:57] Chris: And Ruth replied, “Well, I, I had a better year than he did.” Um, I’m gonna go with $843,000.
[00:40:08] Joe: 843,000. You don’t wanna put a bunch of change on that then?
[00:40:11] Chris: I don’t. I’m a fan of round numbers.
[00:40:14] Joe: Yeah. And so is Doug. He thanks you from the bottom of his heart. Paula, you’ve got, uh, 319,741, and you’ve got 843,000. Where are you going?
[00:40:28] Paula: You know-
[00:40:31] Joe: Well, I don’t know. That’s why we need you to tell us.
[00:40:35] Paula: So what are some of today’s highest paid players paid, and how popular was baseball back in 1939?
[00:40:43] Chris: If I may, those are great questions, and they work at odds with one another-
[00:40:47] Paula: Right …
[00:40:48] Chris: because players are paid so much more now, and baseball was so much more popular then.
[00:40:55] Paula: Mm.
[00:40:55] Joe: Yeah, isn’t that funny?
[00:40:56] Paula: Hm. Okay, I am going to take the upside of OG’s guess. He ended with 71 cents, so I’m gonna go with 72 cents. That’s 319,741.72.
[00:41:16] Paula: Yes.
[00:41:16] Joe: That’s the way it happens here. All right, we’ve got our guesses locked and loaded. Who’s closest? We’re gonna find out in just a moment. We’ll be right back. All right, OG, you kicked this off with 319,741 and 71 cents. How you feeling about that now, big guy?
[00:41:34] OG: Well, I feel like Paula could have just, uh, taken $1 under Chris’ and had the same effect.
[00:41:38] OG: But, um, it sounded cooler- It’s- … to say 72 cents, I guess.
[00:41:43] Joe: It depends. If it’s 400,000, Chris would, uh… Oh, no, you could- No,
[00:41:47] OG: she would’ve got it, so
[00:41:49] Joe: $1
[00:41:49] OG: under. Yeah. Oh, it would’ve been closer- Chris- … for me though, I suppose, so never mind.
[00:41:52] Joe: Yeah, right. Right. Uh, Chris, 843,000 bucks. If it’s, if it’s a million dollar salary or $10 million salary, you’ve, you’ve got it.
[00:42:02] Chris: Uh, I feel like I’m either gonna horribly disappoint Jesse Cramer or he’s gonna owe me a drink.
[00:42:10] Joe: Oh, we’re hoping it’s the latter, my friend. And then, uh, Paula?
[00:42:14] Paula: I just like the fact that I’m gonna make Doug do some math- … with the 72 cents.
[00:42:20] Joe: Well, let’s hear how good that math is. Doug, who’s taking home the win today?
[00:42:27] Doug: Hey there, Stackers. I’m hot dog sommelier and lower GI tract expert, Joe’s mom’s neighbor, Doug. You may recall that before the break we were talking about America’s favorite pastime, the game of baseball. Did you know that over the course of a season, Major League parks sell about 19 million hot dogs, or as Milwaukee fans call it, breakfast?
[00:42:48] Doug: Wow, 19 million. That means there are a lot of guys who pay $9.75 for a dog in the first inning and say, “You know what? I better get three more.” Lou Gehrig signed with the Yankees in 1939 for an estimated salary of $35,000. More importantly, we asked our experts on this esteemed panel, what was baseball great Lou Gehrig’s 1939 salary in today’s dollars?
[00:43:14] Doug: Well, you know I’m not gonna give you the answer straight away, but what I will tell you is that it is $519,296.29 more than OG’s guess, $519,296.28 more than Paula’s guess, and just $4,461 less than what Chris/Jessie guessed. Wow. The correct answer is $838,539, making Chris and Jessie our winner.
[00:43:45] OG: Wow.
[00:43:46] Doug: Wow. So had Paula come in- I, I-
[00:43:48] Doug: one cent under Chris, she would have won.
[00:43:52] Paula: Wow. I
[00:43:53] OG: had the right initial number, I just figured it only doubled three times, and I rounded down a little bit. I thought the salary was 40, and my… Like, if you’d have asked the salary, I was gonna say 40K. What’s- So I was pretty close there, I just thought it, I thought it went 40, 80, 160, 320.
[00:44:08] OG: That’s how I got to it, so.
[00:44:09] Doug: Paula, to your questions earlier about, you know, what’s the average salary today, uh, it wouldn’t have helped you. In 2026, the m- league minimum is $780,000 a year, and the average is 5.3 million right now. Wow. Another interesting point here that I think is, you know, the, the sal- salaries have skyrocketed.
[00:44:30] Doug: The 2026 average batting average right now is 243. Oh. In 1939, Lou Gehrig was forced to take a pay cut by the Yankees because he had an off year the year before and batted 295. But there we go. They thought he had a bad year. So- Wow … we’re gonna give you a 40% pay cut.
[00:44:49] Joe: Chris, again proving your point, baseball- Yeah
[00:44:51] Joe: far more popular, uh, yet, uh, people paid a lot more.
[00:44:55] Chris: That’s what television money will do for you.
[00:44:57] Joe: That is what telev- When we get that big television deal- In your ears is what- … or you do at, uh, Money Unplugged or Paula does at Afford Anything, we get that big television money from podcasting.
[00:45:06] OG: Paula did get all that television money, didn’t she?
[00:45:08] Joe: She, oh, she did get the television- Right … the Netflix money.
[00:45:11] Paula: The, yeah, the, the Netflix. It was, uh- The
[00:45:13] OG: Netflix and chill money.
[00:45:17] Joe: All right, time for the second… Well, it’s, it’s a little past the second half, but we’re gonna play a game called In or Out. This is our little debate session. I will give you a financial concept, guys- Wait, what’s the, what’s the
[00:45:29] OG: game called again?
[00:45:29] OG: It’s called In
[00:45:30] Joe: or Out. Are you in- Oh, In or Out … or are you out? Okay. Yes. Uh-
[00:45:35] OG: It’s a different game altogether, forget it.
[00:45:37] Joe: This is, this is where we’re gonna debate some of these popular rules, these rules we need to unlearn, or are they rules that are rules for a reason? And Chris, as our, uh, well, as today’s trivia champ, we’ll have you go first.
[00:45:50] Joe: Are you in or out on this, Mr. Hill? Everyone should own a home, in or out?
[00:45:57] Chris: I’m out on that
[00:45:58] Joe: How come?
[00:45:59] Chris: Uh, because, uh, I vividly remember the housing crisis from earlier this century. Um, no, I think, uh, I’m a big believer in, uh, live within your means, and I think for a lot of people, owning a home is aspirational, and it should be, but, uh, not everyone should own a home.
[00:46:20] Joe: Paula, you own a home, you just don’t live in it.
[00:46:23] Paula: That is correct. I am a renter for my personal residence but a owner for my rental properties.
[00:46:30] Joe: Yeah, OG, in or out on that one?
[00:46:32] OG: I am out on having to always buy a house. Is that the right way to say that?
[00:46:36] Joe: Yep, that’s right. Yeah. Let’s start with you for round two.
[00:46:38] Joe: Paying off debt should come before investing. Are you in or out? I
[00:46:43] OG: mean, I need some more information. Uh, I would say 401contributions to the match, yes. I might even be so motivated as to say maybe a little bit of cash reserve savings or maybe just a Scotia Roth savings. But generally speaking, 401I would let you do to the match contribution, and then, uh, if it’s high-interest debt, yeah, you’re gonna wanna pay that off.
[00:47:06] Joe: Paula?
[00:47:08] Paula: Oh, if there’s a match, get the match, ’cause that is part of your compensation, right? Why would you not accept a portion of your compensation? And no matter… Even if you’ve got credit card debt, no matter what the interest rate on that debt is, even if it’s 22%, I mean, if you’re getting a even 50 cents for every dollar that you put in, that’s way higher, way worth it.
[00:47:28] Chris: Chris? Yeah, I, I, I agree with all of that. The one thing I’ll add to what Paula just said is, um, discretionary income. So yes, 401, you get a match, that’s part of your compensation. Take that, grab that. If you have high-interest credit card debt, I think y- you should pay that off before you start buying individual stocks, funds, ETFs, that sort of thing, because y- you’re probably not gonna be earning 22% a year, and paying off that 22% a year credit card debt is a way to pay yourself first.
[00:48:02] Joe: I love these ’cause these are these, some of these rules that we hear all the time, and I love how you guys are parsing into them. Let’s stick with you, Chris. In or out on this one? You should never carry a mortgage into retirement.
[00:48:14] Chris: I think I’m out on that. Even with the way mortgage interest rates have increased over the past five, 10 years, yeah, you can, you can carry a mortgage into r- uh, retirement.
[00:48:28] Chris: There are people I have talked to on my show who have said that the biggest mistake they’ve made financially is paying off their mortgage.
[00:48:35] Joe: Hmm.
[00:48:35] Chris: They did it because it helps them sleep better at night, but they know mathematically they’re better off with a mortgage even at 5, 6, 7% because they can go invest and do better than that.
[00:48:47] Joe: Chris, on the other side of that discussion, you’ve had our friend and, uh, apparently your cousin Andy Hill on- … on your show, who credits his success to the fact that he let the math go and, and, uh, paid off his mortgage early.
[00:49:00] Chris: Yeah, absolutely. You know, Dan Pink, bestselling author, talked about, like, “It, it’s by far the biggest financial mistake I’ve made, but I sleep at night.”
[00:49:09] Chris: And you know, he, he grew up in a home when he was a kid where, um, there were significant money challenges, and so sort of carrying that forward into his adult life, he was like, “No, I’m gonna be very safe and conservative. I know it’s not mathematically the right thing to do, but I’m gonna pay off my mortgage.”
[00:49:28] Joe: Paula, never carry a mortgage into retirement. In or out?
[00:49:31] Paula: Out. I’m out on that one. Retirement is just a time period in your life in which you have a particular income. Yeah, and that income is your Social Security payment, your pension if you have one, your withdrawal from your portfolio. Like, you have a specific income just as you do at any other time in your life.
[00:49:52] Paula: So why would you not just plan to pay a portion of your mortgage from your income?
[00:49:59] OG: OG? Gun to my head, out. But I think you’ll have a better retirement if you don’t have a mortgage.
[00:50:06] Joe: We haven’t started with Paula yet, so let’s do one more round here. You need a budget to build wealth, in or out?
[00:50:14] Paula: Mm, out. I’m a believer in what I call the anti-budget, which is if budgeting is the calorie counting, then the anti-budget is the intuitive eating.
[00:50:23] Paula: So the anti-budget is pull off, uh, your savings first, and, uh, when I say savings in this context, I mean anything that improves your net worth. So decide how much you want, the portion of money that you want to dedicate towards net worth improvement, yank that off the top first, and then whatever is left over is yours to spend.
[00:50:45] Paula: It doesn’t really matter if you’re spending it on clothing versus groceries versus Taylor Swift tickets. Like, either you’re spending it or you’re saving/investing it.
[00:50:56] Joe: Let me push back just a little bit. Can you do it that way forever and never have a budget and build wealth as successfully?
[00:51:04] Paula: If there is a sufficient delta between spending and expense…
[00:51:08] Paula: Um, sorry, income and expense, uh, then yes. So the time when a budget becomes very useful is when that gap is so small that you need to really heavily scrutinize what you’re spending on in order to be able to, to increase the size of the gap by shrinking your spending. But if you have a sufficiently wide delta, then you’re good.
[00:51:30] Paula: Don’t need it. Like, yeah. Yeah. It’s not necessary.
[00:51:32] Joe: OG, need a budget to build wealth, in or out?
[00:51:35] OG: Out. Budgets suck.
[00:51:39] Joe: End of story. Chris, need a budget to build wealth?
[00:51:43] Chris: Uh, I’m out on that. Uh, you, you need a plan, but you don’t need a budget.
[00:51:48] Joe: I’m gonna do just one more, and I think this we can do this really quickly ’cause I had this on my sheet and I was like, “Uh, we’re done,” but I really wanna do this one.
[00:51:56] Joe: Chris, in or out, financial independence is mostly about behavior, not math.
[00:52:01] Chris: 100% agree.
[00:52:03] Joe: He is in. Paula, you?
[00:52:09] Paula: I have to choose one that I’m in.
[00:52:11] Joe: OG? Yeah.
[00:52:13] OG: Yeah, if information was all that’s required, we’d all be millionaires with six-pack abs. It’s, um- … it’s just, um- It’s six-pack wallets … it’s behavior that matters.
[00:52:23] Joe: Right. Yeah.
[00:52:23] OG: It’s the behavior that matters a- across the board.
[00:52:26] Joe: That’s a great place to leave it, and what a great discussion.
[00:52:29] Joe: So thank you very much, all three of you. Let’s find out before we say goodbye what’s going on at your brilliant channels. Chris, Money Unplugged, what’s coming up, man?
[00:52:40] Chris: Coincidentally, or maybe not coincidentally, uh, the latest episode of Money Unplugged is you, Joe. Um- Awesome … and coming up la-
[00:52:50] Joe: Best episode ever,
[00:52:51] Chris: I’m sure.
[00:52:52] Chris: Coming up later in the month, Paula will be on. Um, so- How about that? So yeah, these are, these are- No offense
[00:52:58] OG: taken.
[00:53:02] Chris: I thought we’d talk afterwards, OG. Um, no, and it’s very much a 180-degree switch from the shows that I was hosting at The Motley Fool, whereas those were very much about the news and had a very almost nonexistent shelf life. These are conversations that, uh, are not about the news. They’re just about people’s lives and how they feel about money, and, um, episodes from last year are just as relevant as, uh, the episode with you, Joe.
[00:53:29] Joe: Speaking of timeless lessons, lots of timeless lessons I learned listening to Money Unplugged. Paula, what’s coming up on the Afford Anything podcast?
[00:53:38] Paula: On the Afford Anything podcast, we have, uh, an interview with Jason Hill and Linda Wilde. They are- Uh, one is a Harvard- Is that other
[00:53:46] Joe: cousin? Is that Chris’s other cousin?
[00:53:49] Joe: We’re everywhere.
[00:53:50] Paula: The Hills are alive. One is a Harvard professor, the other is a longtime practitioner. They talk about the ABCs of how to think through business. So, um, that’s on the Afford Anything podcast. We’ve also got, Joe, a episode with you in which we answer three audience questions. So, uh, all of that is on the Afford Anything podcast.
[00:54:11] Joe: We have so much fun doing that. Yeah. And that’s Afford Anything. OG, what’s going on with you this fine weekend, my friend?
[00:54:18] OG: Oh, well, you and I and Doug and maybe Chris, I don’t know, m- but maybe you qualify, it’s Father’s Day weekend, right? It is. Yes, it is. So this is, this is that, uh, great weekend where, you know, like on Mother’s Day weekend or Mother’s Day, you know, they, uh, they say, “You know, for Mother’s Day you should take the kids, give your wife some time to just, you know, no kids.”
[00:54:44] OG: And then they say, “Hey, it’s Father’s Day. Don’t you want to be with your kids? It’s Father’s Day,” the whole time. It’s all a trap. And so it’s r- it’s really great. It’s really awesome. Um- So obviously US Open weekend this weekend. So watching golf, hanging out, riding a bicycle.
[00:55:00] Joe: That’s the way you spend Father’s Day.
[00:55:02] OG: Nice.
[00:55:02] Joe: Yeah. Uh, Happy Father’s Day to all the dads out there, and I hope you get to spend time with your dad. I hope so. Yep. And, uh, if you are a dad, go spend time with the kids. Make mom happy ’cause even on Father’s Day, Momma ain’t happy, nobody’s happy. By the way, I’d like to do one more shout-out. As I mentioned, we record these on Mondays.
[00:55:19] Joe: It’s always fun pretending it’s Friday on Mondays. So come join us on Monday afternoons. But this particular Monday, our friend Melissa hanging out with us. Melissa became financially independent this week. She quit her job, and she is- Sweet … out of there. So nice job, Melissa. Congrats. Yep. Friends of ours from Detroit, good friend from Detroit, and glad to see that she gets to hang out with us now during the day.
[00:55:42] Joe: So Melissa, we know what you’re doing every Monday afternoon, I’m sure. All right. That’s gonna do it for today. Doug, you’re gonna bring it home for us, man. What should we have learned on today’s show?
[00:55:53] Doug: Well, Joe, first take some advice from Chris Hill when he said, “It’s okay to be frugal. Just don’t be cheap.”
[00:56:00] Doug: You listening up there, Ma? Second, were you taking notes when OG was talking? How about when he said, “It doesn’t necessarily take money to make money”? Oh, you missed that one? Should have been taking notes. But the big lesson- Don’t forget to tell Ma to get the whole wheat hot dog buns. After all those dogs, you’re gonna need the fiber.
[00:56:22] Doug: Trust me. Thanks to Chris Hill for joining us today. You’ll find his podcast, Money Unplugged, wherever the finest podcasts are distributed. We’ll also include links in our show notes at stackingbenjamins.com. Speaking of the finest podcasts, thanks also to Paula Pant for hanging out with us today. You’ll find her San Fran-tabulous podcast, Afford Anything, wherever you listen to the fantabulous-est-est podcasts.
[00:56:52] Doug: Thanks also to OG for joining us today. Looking for good financial planning help? Head to stackingbenjamins.com/og for his calendar. This show is the property of SB Podcast LLC, copyright 2026, and is created by Joe Saul-Sehy. You’ll find out about our awesome team at stackingbenjamins.com, along with the show notes and how you can find us on YouTube and all the usual social media spots.
[00:57:18] Doug: Come say hello. And oh yeah, before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. 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, Doug, and we’ll see you next time back here at the Stacking Benjamins show.
Leave a Reply