You’re making more money than you ever have. Your net worth on paper looks great. And yet somehow, there’s still too much month left at the end of the money. Joe, OG, Paula Pant, and Jesse Cramer dig into why high earners feel financially squeezed — and why the answer is almost never what you think it is. Spoiler: it’s usually not the lattes, it’s not too many accounts, and it might not even be a spending problem at all.
What You’ll Walk Away With
- Why lifestyle inflation doesn’t feel like inflation — it feels like deserved progress, and why that’s exactly what makes it so hard to catch
- The crucial difference between feeling like you didn’t save enough and actually not saving enough — and why OG’s take on this is the most useful thing in the episode
- Paula’s one big fixed cost audit: why making a single large decision beats constantly making small DoorDash decisions
- Why tracking your spending is the calorie counting of personal finance — only useful short-term, but powerful for getting an honest snapshot before you make any changes
- The paper wealth trap: why a high net worth and strong portfolio can coexist with genuinely tight monthly cashflow and why people conflate them
- Jesse’s one-line-item challenge: find one thing on last month’s credit card statement you wish you hadn’t spent, cut it, and see what happens to your motivation
- Why OG’s advice to “just decide not to feel squeezed anymore” is less dismissive than it sounds — and the number of times the actual math completely contradicted a client’s feelings
- The boats conversation: why a good financial advisor’s job isn’t to tell you whether to buy the boat but to show you what it costs in terms of your actual goals
- Why comparing your savings rate to the FIRE community can make you feel terrible about saving an objectively impressive amount of money
- The goal clarity test: if you can’t articulate what you’re saving toward in specific, time-bound, dollar-denominated terms, the squeezed feeling probably has nothing to do with your budget
Why This Matters Now
Housing, food, and transportation costs are genuinely higher. That part is real. But for a meaningful chunk of the people who feel financially squeezed, the math and the feeling are pointing in different directions. This episode is about figuring out which one you’re actually dealing with — and what to do differently once you know.
From the Basement
Joe, OG, Paula Pant, and Jesse Cramer work through the Wall Street Journal’s reporting on why so many Americans feel financially squeezed even at high income levels — and whether the problem is real, psychological, or both. OG is recording from a conference adjacent to Disney World and has opinions about wood delivery, boats, and people who feel bad about saving $87,000 a year. Paula gets the giggles. The trivia competition features a man who mowed Steve Wozniak’s lawn and had the license plate to prove it. OG wins with suspicious precision. Ronald Wayne, who sold his 10% of Apple for $800 twelve days after founding the company, has a worse story than anyone on this podcast.
Resources Mentioned
Stacking Benjamins Community — stackingbenjamins.com/basement
Financial Samurai — referenced for the lifestyle inflation quote; financialsamurai.com
Afford Anything podcast — Paula Pant; Joe joins most Tuesdays for listener Q&A
Personal Finance for Long-Term Investors — Jesse Cramer; current series: 14 risks in retirement, Charlie Munger inversion framework; two-part series now complete
Stacking Benjamins Vault — stackingbenjamins.com/vault
Stacking Benjamins Newsletter (The 201) — stackingbenjamins.com/201
OG financial planning calendar — stackingbenjamins.com/og
Our Topic: Why High Earners Feel Broke
The Stock Market Has Never Been So Good When People Have Felt So Bad
During our conversation, you’ll hear us mention:
- Feeling Broke
- High Earners
- Stock Market Gains
- Financial Anxiety
- Lifestyle Inflation
- Lifestyle Creep
- Income vs Wealth
- Comparison Culture
- Keeping Up
- Country Clubs
- Luxury Cars
- Private Schools
- Housing Costs
- Grocery Inflation
- Transportation Costs
- Mortgage Rates
- Golden Handcuffs
- Cash Flow
- Net Worth
- Convenience Spending
- DoorDash Habits
- Time Compensation
- Outsourcing Chores
- Emotional Spending
- Saving Goals
- Financial Independence
- Budget Tracking
- Spending Audits
- Financial Complexity
- Margin Creation
- Subscription Overload
- Too Many Accounts
- Opportunity Cost
- Wealth Perception
- Asset Growth
- Retirement Planning
- Fixed Expenses
- Discretionary Spending
- Utility Maximization
- Lifestyle Design
- Goal Clarity
- Money Scripts
- Financial Flexibility
- Social Media Comparison
- Spending Priorities
- Joy Audit
- Value Alignment
- Wealth Building
- Financial Confidence
- Creating Optionality
Our Contributors
Jesse Cramer
Another thanks to Jesse Cramer for joining our contributors this week! Hear more from Jesse on his show, Personal Finance for Long-Term Investors – The Best Interest, on Spotify.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
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
- Apple co-founder Steve Wozniak famously sold much of his Apple stock early. What percentage of Apple did Wozniak originally own when the company was founded?
Mentioned in today’s show
- Of Course $10 Million Is Enough To Retire Early, Don’t Be Crazy – Financial Samurai
- 🔒 Your financial life deserves protection too. See why Stackers are checking out Surfshark (use promo code STACKINGB at checkout to get an extra four months of Surfshark VPN)
Join Us on Monday!
Tune in on Monday when share the findings of a study that show how millions of people could retire earlier than they planned, plus our plan to help you prep.
Miss our last show? Check it out here: Retire by 30: Cody Berman on Building Financial Freedom Faster Than You Think (SB1850).
Written by: Kevin Bailey
Episode transcript
[00:00:00] opener: I’ve got a four-bedroom house in a great community. Like my car? It’s new. I even belong to the local golf club. How do I do it? I’m in debt up to my eyeballs
[00:00:20] Doug: From the basement of the YouTube headquarters, it’s The Stacking Benjamins Show
[00:00:35] Doug: Joe’s mom’s neighbor, Doug, and you know the drill. You’ll feel rich once you get just a little bit more money. And yet, more than ever, high earners are reporting that they still feel broke. So how do you break free from feeling strapped all the time? We’ll answer that on today’s show. But that’s not all.
[00:00:54] Doug: We have the regulars here, which means we might just see a margin call during my trivia question. And now, a guy who’s always into leveraging a good time, it’s Joe Saul-Sehy
[00:01:14] Joe: What better time can you have than spending your Friday with us? Hey, everybody. Welcome back. We’re super happy you found your way to the greatest money show on Earth. This is our Friday episode, where we take something that I saw in the news, and we decide to discuss it and hopefully, uh, send you on your weekend with some, uh, uh, better, better financial livelihood than you had before you got to us.
[00:01:41] Joe: How come I can’t make a sentence, Doug? Why can’t I make a sentence?
[00:01:44] Doug: Because we just said you’re, you’re willing to leverage fun. That means you’re sucking the fun out of this- … to take it someplace else, and your brain is too focused on sucking the fun out of this.
[00:01:56] Joe: Yes, and this is gonna be fun, isn’t it?
[00:01:58] Joe: We’re gonna have a good time.
[00:01:59] Doug: So much fun.
[00:02:00] Joe: Yes, talking about this because the fun meisters are here. Speaking of fun, the guy who for 14 years has been looking at portfolios and, uh, with helping people- … uh, hear the voice of doom.
[00:02:12] OG: 14 years? Like 29 years, but close enough. Well,
[00:02:15] Joe: the past 14 years of podcasting, I mean.
[00:02:17] OG: Oh, I see. Yes. Yeah.
[00:02:19] Joe: Yes. Mr. OG’s here. How are you, man?
[00:02:21] OG: Excited to be here. Thanks for having me, Joe.
[00:02:24] Joe: It’s …
[00:02:25] Doug: We are- The, the Bill Belichick of personal finance- … happy to be here.
[00:02:29] Joe: That’s what we should’ve said.
[00:02:30] OG: I kinda have that vibe right now, I’ll be honest. You caught me at that time. It’s that time of the day
[00:02:35] Joe: Well, we’re about to spice it up, OG, because we’re gonna have a lot of fun.
[00:02:39] Joe: You know why? Because a woman who’s outside of her, uh, the swimming pool in her- … in her building, we just saw somebody walk by in a towel and a bikini. Paula Pant is here.
[00:02:53] Paula: Well, okay, my gym is also a co-working space, which is also the entrance to the outdoor pool. When you live in New York, everything becomes very multifunctional and multipurpose.
[00:03:04] Paula: So I’m in my gym/co-working/pool entrance/yoga studio.
[00:03:09] OG: Otherwise known as a hallway. And pool table, I see in the background.
[00:03:12] Paula: Oh, yes, and pool table. Yes, so we’ve got double pools.
[00:03:15] Joe: Yes, and by the way, the guy who’s the pool shark on this podcast from the Personal Finance for Long-Term Investors show, Jesse Cramer’s here.
[00:03:23] Joe: Are you pool shark, Jesse?
[00:03:24] Jesse: I’m, I’m pretty bad at pool. But, uh, I, I kind of want to combine… So if OG is, uh, the Bill Belichick, and where Paula is right now in the swimsuits, we had… I think Bill Belichick is currently dating, like, a 25-year-old? Okay. So I just want to ask, like, OG, kind of who’s… I think her, her name’s Jordan Hudson.
[00:03:42] Jesse: So, like, who’s the Jordan Hudson to OG’s Bill Belichick in this, in this- Ooh, ooh, pick me … weird convoluted situation that we find ourselves… Is, is it Doug? Is it Doug in the bikini?
[00:03:52] Joe: Yes.
[00:03:54] Doug: I wanna be in charge of all of his media.
[00:03:56] Joe: Wait, I didn’t know where we’re going with any of that, so I’m gonna just quickly change the topic.
[00:04:03] Joe: So you ever meet somebody making great money who still acts like every trip to Costco requires a payment plan? Well, that’s what we’re gonna, that’s what we’re gonna talk about today, because the Wall Street Journal just featured a piece that I read over the weekend, and here’s the headline, guys: The Stock Market’s Never Been So Good When People Have Felt So Bad.
[00:04:20] Joe: And just this general difference between the way people feel about their money and the, you know, the great success that we’ve had in the stock market. So people with a six-figure salary still stress eating. You’ve got the Amazon boxes. That sound familiar, OG?
[00:04:37] OG: Mm-hmm
[00:04:38] Joe: No idea where, no idea where the money went.
[00:04:40] Joe: Retirement contri- people making retirement contributions on time, right? But you still feel this little sense of panic. So things are going okay, just doesn’t really feel okay. We’re gonna help you with that on today’s show. So can’t wait to get this discussion started and, uh, dive into all that. But first, guess what, guys?
[00:05:00] Joe: We have a brand new sponsor for today’s show. So we’re going to surf into today’s discussion. Like what I did there? Huh? Huh?
[00:05:08] Doug: Doug’s getting paid.
[00:05:09] Joe: Yes. Sponsored by Surfshark. If you’re like us, you’re spending a lot of time online right now watching the financial markets bubble. You wanna turn that stuff off.
[00:05:21] Joe: You also want to, uh, stop watching all those talking heads on CNBC and Fox Business. Turn that stuff off. I may have been doing a bunch of that. Maybe talking yourself into our Detroit Lions winning 11 games this fall. Much better to focus on that. But while you’re doing all that, your data’s basically out there for anyone to grab, and that’s where Surfshark comes in.
[00:05:41] Joe: Surfshark’s a VPN that encrypts everything you do online, so whether you’re working on stacking your Benjamins at home, at a coffee shop, or scrolling your brokerage accounts 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.
[00:05:56] Joe: Here’s one thing I really like, one account covers unlimited devices, so your phone, your laptop, your smart TV, everything’s locked down. They also have a strict no logs policy, so even the Surfshark people, they can’t track what you’re doing either. Plus, features like CleanWeb block ads and malware before they even hit your screen.
[00:06:13] Joe: So if you wanna browse smarter, maybe even find better deals on travel or online marketplaces by switching up your virtual location, check it out. Go to surfshark.com/stackingbee, and guess what you get when you do that, Paula?
[00:06:26] Paula: What do you get?
[00:06:27] Joe: Oh, I’ll tell you. If you use code stackingbee at checkout, you’ll get an extra four months of Surfshark VPN.
[00:06:36] Joe: That’s surfshark.com/stackingbee, code stackingbee. All right. We’ve got a couple more sponsors who help us keep on keeping on because Stacking Benjamins is always free and worth every penny. So we’re gonna hear from those sponsors who make it free, and then Jesse, Paula, OG, Doug, and I, we’re gonna talk about maybe helping you feel a bit better about where your money’s at in this particular economy
[00:07:10] Joe: All right, guys, let’s surf into this issue. Why doesn’t higher income feel safe? Shouldn’t more money solve this problem, Jesse Cramer?
[00:07:21] Jesse: It should. It really should. There are probably different reasons. The most common reason I see simply comes down to, you know, there are so many things in this world we can spend money on, and there are, there are probably more things today, I mean, I’m, I’m almost positive in this statement, there are more things today that we can spend money on than ever before in history.
[00:07:38] Jesse: We can get anything delivered to our house, like, overnight. There are all these cool services out there in the world or fun things to do, places to see, places to travel, activities to participate in, things to get our kids involved in. And like some of the stories that I’ve seen firsthand and, like, talked to the people firsthand, it’s simply lifestyle inflation.
[00:07:58] Jesse: Now we’re earning $100,000 more, and that gets spent on a nicer golf course to be a member of, a better summer camp to send our, our kids to, dining out at fancier restaurants more often. And, and, uh, from a, just zooming out to the, the furthest out we can zoom, it just comes down to making that active decision to spend less.
[00:08:17] Jesse: I think there’s probably someone on this panel right now who has an amazing motto about exactly- … this topic, and, uh, I, I’m interested to hear what she has to say.
[00:08:25] Joe: Who, Doug? Is it Doug?
[00:08:28] Jesse: It is. It’s, it’s spend more money on tartan wallpaper. Neighbor Doug.
[00:08:33] Joe: Paula, I think, uh, Jesse’s talking about you, but I wanna take just one side of that equation.
[00:08:38] Joe: And, and let’s get rid of the quote, “this economy,” ’cause as you know, there’s always something for us to worry about, right?
[00:08:43] Paula: Right.
[00:08:43] Joe: But, but I also feel like just as you earn more money, people think more money solves the problem. I feel like more money often comes with more anxiety. True or false?
[00:08:53] Paula: False. Mm.
[00:08:55] Paula: More money creates more optionality. I do not see how earning more money could be a bad thing. When you have not a lot of money at your disposal, at a certain point you can’t shrink down any further. Like, rent can only go so low. Uh, the cheapest rice and beans from Costco bought, bought in bulk- But you don’t think
[00:09:12] Joe: income and anxiety rise together?
[00:09:14] Joe: Like, more income just makes me worried that, “Hey, now I’m away from this minimal lifestyle- Mm-hmm … and it’s all gonna go away. That balloon’s gonna pop at any second, and I gotta go back.”
[00:09:25] Paula: I think that anxie- if, if that worry translates to a higher savings rate, then that is a positive worry, and that’s not the same as anxiety.
[00:09:33] Paula: Anxiety is often a, a disposition that a person has regardless of circumstance. But if a person has income and they’re worried about losing it, the obvious solution is save more. Save more and invest more, because that’s the antidote to losing it.
[00:09:50] Joe: Well, OG, let’s bring you into this discussion. I think there might be something else going on, too, which is, you know, there’s this phrase, Wherever you go, there you are.
[00:10:00] Joe: And I think some people feel like, “Hey, if I make more money, all of a sudden I’m gonna be happier.” But you show up, and you’re like, “Maybe success- Success should feel better than it does. Financial success should feel better than it does
[00:10:15] OG: Well, I mean, I think, you know, both Jesse and Paul have already talked about this in terms of kind of increasing obligations as your life also expands.
[00:10:27] OG: You have to be really cognizant of this because at the end of the day, it’s very easy to, you know, have that, have that desire or… You know, and it’s cliché to say like keeping up with the Joneses, but it’s very easy to kind of fall into that trap a little bit, and it’s the rich dad, poor dad type of concept or something, where every time you get something else, you’re like, “Okay, now that means I can finally do this other thing.”
[00:10:50] OG: And at some point in time, you have to decide whether or not, like, the next thing is worth all of the energy to do. Like, you know, Jesse, I think you said, like, the fancier country club, right? It’s like, is it worth it? Like, like, what, what is the difference? Yeah. It’s already a private golf club. Is, is it worth the extra 1,000 bucks a month?
[00:11:07] OG: You know, or is it worth the extra $100,000 sign-up fee? The same thing with a car. Like, if you’re buying a $75,000 Yukon, that’s cool. Is it worth the extra 50 to upgrade to the Mercedes? I’m not sure. But, like, there’s always something above it, you know? There’s always another thing until you get to, like, I don’t know, I guess Elon probably the number one guy right now.
[00:11:27] OG: There’s always somebody that has more than you, and if your comparison is against other people, it’s just a bad comparison because you’ll never win that. Because there’s always somebody else that’s gonna have, you know, just the next, the, the fancier house, the, the better car, the, the cooler watch. The kids go to a better school.
[00:11:48] OG: There’s always something. Some of those things are a good thing to do or a good thing to have, but at some point you just gotta go, “Okay, enough is enough.”
[00:11:55] Joe: What do you mean some of those things are, are good? It, it is
[00:11:57] OG: good to compare yourself? Like paying for, paying for education. Oh, okay. Yeah, paying for education, for example.
[00:12:01] OG: If you’re in a community that has a notoriously bad school system and now you have the wherewithal to send your kids to a better school, whether that’s, you know, you can move into a better school district or you can send your kids to a private school and there’s better attention or harder classes or whatever the case may be, however you would evaluate that, there’s a good ROI on that generally speaking.
[00:12:23] OG: But once you have a little bit of escape velocity in that spot, like is it better to go to the next best school? Like, does that curve flatten out in terms of utility? I think it does after a while. You know, like going from Costco rice and beans to name brand rice and beans, big improvement, but it’s still rice and beans.
[00:12:42] OG: You know? Like, now you gotta go to like ribeye. ‘Cause- But, like, once you get to ribeye, you’re like, “Okay, I got ribeye. Is it that much better to have Wagyu ribeye?” I mean, it’s better, but is it that mu- is it 10X better? I don’t think so.
[00:12:54] Joe: It’s funny talking to a couple chefs that I know. They’re like, “Most people have no idea the difference.”
[00:13:00] Joe: I could sell them whatever. I could t- I could call it Wagyu and p- m- most people would be like, “Eh.”
[00:13:04] OG: Yeah, you can still cook it like . I mean- … you c- you can still grill the hell out of it and make it well done, and it’s still gonna suck. There it is. It’s just as bad as the Costco version.
[00:13:14] Joe: Doug?
[00:13:15] Doug: I just wondered if his logic also translates to a set of irons and maybe a rescue four wood.
[00:13:22] OG: Well, nobody has rescue four woods. That, that would be a complete utter waste of energy and money. But one might be okay with a seven wood, for example. Seven, okay. Uh, and maybe a five wood to replace a five iron. Um, absolutely a good use of excess capital, for sure.
[00:13:37] Doug: Asking for a
[00:13:37] Joe: friend. Not even sure what they’re talking about, Jesse, so we’ll move on.
[00:13:42] OG: You wouldn’t know.
[00:13:43] Joe: I would not know. It’s very
[00:13:44] OG: obvious.
[00:13:45] Joe: Absolutely. Jesse, you mentioned lifestyle creep. How easy is it and, and how much of a culprit is lifestyle creep when it comes to feeling this, uh, pinch when you’re making, uh, well over six figures?
[00:13:57] Jesse: Yeah, I’m, I’m not sure. I mean, you could always point the finger at, of course, inflation, and then just some of these like, yes, the necessities of life are more expensive than they ever have been before, like no doubt about it.
[00:14:08] Jesse: But once we get into some of the numbers that we’ve been talking about here on this episode, like some of those income numbers, the, the only logical explanation is lifestyle creep. And a, a little anecdote that I recently went through with someone was, you know, this is a family. So here we are in Upstate New York, Rochester, New York.
[00:14:25] Jesse: We’re near the Finger Lakes. Beautiful countryside, beautiful water. Uh, lots of- Don’t get Doug
[00:14:30] OG: started …
[00:14:30] Jesse: you know, lots of nice houses on the water, and there are plenty of people in Upstate New York who say, like, “Oh, we love to go away to a little cottage on the Finger Lakes.” Now, there comes a point where some people might say, like, “We’re gonna buy one of those cottages,” like, right?
[00:14:43] Jesse: “That’s gonna become our, our place.” And one of my thoughts is that might be a really logical thing to do if you plan on spending every extra weekend, every day off, especially during, like, the summer season. If that’s your go-to place, if that’s, like, your number one leisure activity, I bet your ROI on buying that cottage might be really good.
[00:15:03] Jesse: But the problem is that some of these people, once they start earning the kind of money they were earning, they’re like, “Well, we spread ourselves too thin across too many activities.” Hmm. “We buy the cottage in the Finger Lakes. We’re only there four weekends a year,” and it ends up being this huge part of their balance sheet or this huge expense on their cash flow, and they’re really not getting that much utility out of it, to borrow one of OG’s terms.
[00:15:26] Jesse: And, and that’s just the lifestyle creep issue. So the, the problem that I see most often is people think that, “Oh, people like us, right, we, we, we own a lake house. We travel all over the world. We do all these, you know, relatively fancy things,” and they end up doing too many of those different fancy things such that their time is just spread way too thin.
[00:15:46] Jesse: And at the end of the day, they look at themselves and they’re like, “We barely have any money. We’re spending it all.” And I just… I don’t see the ROI that they’re really getting on that. So it is a lifestyle creep issue.
[00:15:55] Joe: Is it wild how buying more things not only clutters your budget, the time that you devote to whatever this thing is that you buy, whether it’s a house or a boat or, heck, even a board game, like, the, just the, the time that comes with it, the time commitment ends up making more stress in your life?
[00:16:13] Jesse: Definitely.
[00:16:13] Joe: Obviously, a lot of this anxiety starts, and people don’t know where it comes from. Part of it might have been that you had lifestyle creep in your life. But how many of us, especially early on, do you think confuse income with wealth? I get this higher income. So I’m making well over six figures.
[00:16:30] Joe: That must mean that I’m rich.
[00:16:32] Paula: Right. Well, I, I think there are, there are, are a couple of things going on, and I actually disagree that it’s all lifestyle creep. Partially, yes. There is the conflation of income with wealth, particularly when you’re early in your career. Let’s say you’ve, you’ve just come out of college or grad school.
[00:16:47] Paula: You’re making real money for the first time in your life. Because you have gone from making nothing as a student to making a lot straight out of school, um, you know, for many people that, that can feel… You suddenly feel rich because the, you haven’t normalized to it yet. So I mean, sure, that’s part of it.
[00:17:06] Paula: But I also do wanna raise the point that over the last five years, costs have, have doubled. I mean, you look at the cost of gas, you look at the cost of groceries, you look at just the cost of housing, mortgage interest rates. Like, you look at just basic, like, housing, food, transportation, those are the three biggest spending categories, and a lot of those costs have gone up significantly in the last five years with a, you know, a level of inflation that we’re not used to seeing.
[00:17:30] Paula: And I think that that, no matter how much you earn, it affects you
[00:17:35] Joe: It is interesting, OG. I mean, on one side we got fixed costs, but, but when we look at where the money disappears, how much of this is, uh, is convenience spending that is a culprit?
[00:17:48] OG: I mean, not only is there probably some, Jesse’s avocation here is, uh, it’s all discretionary lifestyle creep.
[00:17:56] OG: There’s the fixed cost component of it. I’d say there’s another hidden component of this, which is taxes. When you think of, like, this big giant income, or I got a bonus, I’ve, you know, such and such a thing happened and I’ve got this big $200,000 bonus or whatever I should finally be making, it’s like, well, yeah, dude, but you’re gonna owe 40% of that back at least in taxes.
[00:18:16] OG: And God forbid you live in a state that actually charges it too, or a city that charges on top of the state, and it very easily could be well over half. You know, in your mind, you’re like, “I’ve got 200 grand,” let’s say, “to spend,” but after it hits my bank account, I’ve got 97. And maybe if your income is low and you live on your bonus because, you know, that’s how you’re paid, now you’re really not even getting anything extra in your life.
[00:18:44] OG: It’s just like you’re filling your savings account back up to drain it back down to zero over the next 12 months. And so I can see how this can feel as, like, a very, like I’m spinning my wheels a lot. I would offer the other side of this too, which is it doesn’t take a lot over a long period of time to stay ahead.
[00:19:01] OG: You know, you don’t have to, like, be saving 70% of your income to fund your retirement if you start relatively at a good age. You know, a little bit of money goes a long way. I know you like to save all the what fors on the back end, Joe, but it’s like probably a lot of this is self-inflicted. I can use myself as an example.
[00:19:23] OG: I, I don’t feel any materially different than I did 10 years ago when our income was 10% of what it is today, or 20% of what it is today. I just have different things to deal with now. You know what I mean? Like, we’re able to give stuff away, which is cool, and our- we’re able to spend more on people that we care about, which is cool.
[00:19:43] OG: And yeah, we save a little bit more money. And yeah, we spend money like drunken sailors on occasion. See upcoming Disney trip. Yeah. Planned, like, 10 days in advance. You know that’s cheap when you go- … “Hey, screw it. Let’s go to Disney in 10 days,” you know? In 10 days. You know, with five people. So it’s a blessing, but it’s also, you know, you gotta be able to rein it in and recognize that, like Jesse said, there’s, there’s a fair- fairly decent amount of, uh, excess BS that I think we all justify to ourselves as, as in, you know, I gotta have this.
[00:20:15] OG: I got, or I gotta keep it.
[00:20:16] Joe: Well, and this is actually a question that I have because Jesse, when you were talking about people that only spend four weeks a year out at the Finger Lakes. Now that they’re making more money, they feel like, “Okay, I can afford this thing,” and yet time-wise- The company expects more of them, their career demands more of them, they spend more time doing it.
[00:20:36] Joe: Paula, you and I have joked before that entrepreneurs are people that will work 80 hours for themselves to avoid working 40 hours for somebody else, right?
[00:20:42] Paula: Yep. Absolutely.
[00:20:44] Joe: How much of this spending, Jesse, do you think is emotional compensation? I’m exhausted, so because I’m exhausted, I’m getting DoorDash.
[00:20:53] Joe: Right. Or I’m going out to dinner because, you know what, I just don’t feel like making dinner. Or a little bit of, “You know what? I’ve been working my ass off. Damn it, I deserve this.”
[00:21:01] Jesse: Right. You, you, you just said there, Joe, like emotional compensation, which I could certainly see that, and I also think on the topic of time.
[00:21:08] Jesse: Like some of it definitely is time compensation. Don’t get me wrong, Mike. I still mow my own lawn. I’m not sure I should actually, right? Like, if it takes me 75 minutes to mow my own lawn, especially this time of year where I’m doing it more than once a week, it’s like, could I take that 75 minutes a week and actually use it in a better way, whether it’s spending time with family or working to earn the money?
[00:21:29] Jesse: And like, I think at some point, as people’s incomes increase, they start doing a lot more of that calculus, where they outsource their lawn care. Maybe they have someone to come in and help cleaning with their house, uh, is, or their living space or something like that. And there are all these, like, little incidentals where at one point in my life I never would have outsourced any of that stuff, and now all of a sudden I’m looking at my quote, unquote, “income per hour,” if I wanna think about it that way, and it’s like, why am I still folding my own clothes, right?
[00:21:57] Jesse: I, I know some people who don’t do their own laundry. They, they outsource it all. That, of course, leads to a more expensive lifestyle. So some of it is that, but I would just wager the average person in this predicament might not be thinking of it that way, the way a financial planner or an accountant or almost an engineer would, which is like, “What is my hourly income?”
[00:22:17] Jesse: “What, what does it cost me to do my laundry? Therefore I will outsource.” But I, I would wager, yeah, the DoorDash example is another really good one, Joe, which is like, yeah, you know, I’m busy. I just put in an 80-hour week. I’m gonna spend 30 bucks on a burrito. I bet you that happens more often.
[00:22:31] OG: Jesse, the only way that that calculus works is ac- if you actually use the time to go do the other thing.
[00:22:37] OG: If you say, like, you know, and I think that’s what you were saying before, but if you say, “Well, you know, I, my, my hourly wage is $200 an hour. If it takes me three hours a week to mow my grass and I pay somebody $100 to do it, I saved 5…” You’re like, “That’s making 500 bucks.” Yeah, if you go make $600.
[00:22:54] Jesse: Right.
[00:22:54] OG: If you don’t, you just spent $100 to, like, sit on the couch, which by the way, also could be a good investment- Yeah
[00:23:01] OG: you know, in your R&R. Like, that’s n- I’m not saying that you shouldn’t do that, but there’s
[00:23:05] Joe: two sides to that. It’s funny you say that, OG, because I was thinking, you know, mowing the lawn for me is just a great time. Strap on some, some headphones.
[00:23:14] OG: Oh.
[00:23:14] Joe: Either listen to some music or Li- Thought that sentence was going a different way.
[00:23:20] OG: Paula, Paula picked it up.
[00:23:21] Paula: Yeah. Yeah, yeah. I, I, I had the same thought.
[00:23:25] OG: All I can think about is that Allstate commercial. I see Joe mowing the grass, like, with his headphones on, like, mowing the grass, and, like, rocks are shooting everywhere, and he’s like, “Sorry, Robert. $5 doesn’t buy my undivided attention.”
[00:23:37] OG: You know, he’s, like, shooting rocks against his house and out into the street as cars blow by. You calling me
[00:23:41] Joe: Mayhem? Are you… Is that what you’re calling me, is Mayhem?
[00:23:43] OG: That’s just a really good part. I just wanna learn more about what you’re strapping on- … to mow the grass in Texarkana.
[00:23:49] Paula: I enjoyed the earlier conversation between OG and Doug about their wood.
[00:23:54] Joe: Just, oh,
[00:23:55] Paula: man. The seven wood and the five wood and the- And we
[00:23:58] Joe: are officially off the rails now.
[00:24:00] OG: For the record, mine is the, mine is the seven. His is the five.
[00:24:05] Joe: I want to- I would not
[00:24:08] OG: have-
[00:24:08] Paula: Compared- How, how would you know that?
[00:24:10] OG: Sword fighting, obviously.
[00:24:13] Joe: Okay. I just wanna get back, get this back. You know, what’s funny, Paula, is that you were talking about the cost of groceries, the cost of living, and, and you know, we spent a, a, a fair amount of time so far today talking about discretionary expenses, right- Mm-hmm
[00:24:28] Joe: and controlling those and lifestyle creep. But you were talking about fixed expenses. Like, how much of this just is maybe we bought too much house?
[00:24:36] Paula: Right. Yeah, and you see a lot of people with that predicament right now because they’ve got the h- the golden handcuff situation of, you know, they’ve locked in a mortgage interest rate that’s 3%.
[00:24:46] Paula: Their house is no longer adequate for their needs, but in order to move to a different house, or, or maybe they have a better job opportunity elsewhere, or they need to handle elderly care responsibilities elsewhere. But to move to a different home, even if they downsized, it would be just as expensive because of the home price, the, the increase in home prices as well as the new mortgage interest rates.
[00:25:12] Paula: And, and so you, you kind of see that level of stuckness, and I think part of the frustration that people feel right now is lack of mobility. And generally speaking, when people feel a lack of mobility, then regardless of what their income is, um, that necessarily feels, uh, very frustrating. I think that’s why there’s…
[00:25:28] Paula: one of the reasons why there’s such a delta between how the stock market is doing and how people are feeling.
[00:25:33] Joe: Well, and I think that’s where real wealth is, right, is the, the real wealth is not the amount you make, it’s that margin between the two. Mm-hmm. When you feel like you’ve got some margin that you can take the family to Disney 10 days before, whatever it might be, then you feel this, the, a little bit more sense of safety.
[00:25:48] Joe: By the way, I remember a discussion on another channel quite a while ago, somebody talking about two people with a Lamborghini, and one person has a Lamborghini and it is maybe 1/1000 of their wealth, right? It’s just a thing. It’s just a little car. Somebody else spending nearly all the money they have to buy the Lamborghini.
[00:26:09] Joe: Sometimes purchases can tell you that somebody feels richer than they truly are- I wanna walk through just very quick rapid fire before we go to our break. OG, what’s a purchase you’ll see somebody have where it’s clear the person maybe feels richer than they, than they maybe are?
[00:26:28] OG: Airplane. Oh. Um, too soon?
[00:26:33] OG: What’s a purchase that somebody makes that makes, makes them feel… What was your quest- say your question again so I get it right.
[00:26:42] Joe: When, when you see somebody who, you know, this, this might be a little judgey, but somebody who-
[00:26:47] OG: Yeah …
[00:26:47] Joe: who very well might feel richer than they, than they are. Kind of o- Like, I’m thinking of-
[00:26:51] OG: over their skis. Yeah. I mean, certainly any sort of what I would consider ostentatious, uh, vehicle purchase probably is up there. I have a hard time arguing with real estate purchases, despite being a little over their skis maybe, because it’s just kinda transferring money from one side of the balance sheet to the other, you know, in my opinion.
[00:27:13] OG: Notwithstanding the payment and upkeep and that sort of deal. I mean, honestly, don’t we all kinda go through that very f- I mean, maybe not everybody, but aren’t there periods of time where you’re, like, a little stretched just a skosh thin and that, and then you’re like, “Oh, man, I don’t know”? I mean, I, I distinctly remember having this conversation with my grandfather when he was still alive about his, you know, his house purchase and that sort of thing, and he has this great story where he said, “You know, we, we, we built this house, we got the money from the bank to do it, and, um, you know, the house was done, and now we gotta sign the paperwork.”
[00:27:43] OG: And I said, “How did you feel?” And I don’t remember what he said the payment was. $29 a month or some, you know, like- … whatever the mortgage was. It was some pocket change to everybody here. And I said, “How’d you feel about it?” He said, “Well, I was pretty, pretty convinced that we were gonna be looking for a new place to rent a month from now.”
[00:27:58] Joe: Oh.
[00:27:58] OG: He’s like, “I knew I could make this month’s payment. I wasn’t sure about making next month’s payment.” Wow,
[00:28:01] Joe: that’s tight.
[00:28:02] OG: Well, I mean, but I felt that way when we bought our first house. We were like, you know, you did all the math, and despite it maybe not being exactly perfect, it was like, “Yeah, it’s a little snug, but I think we can pull it off.”
[00:28:12] OG: I mean, when we bought this house, it felt the same way. You know, every single time you do something that s- stretches your confidence, you know. I mean, the bike race that I’m doing, like, like I don’t think I’m gonna do th- I’m six weeks away, and I’m like, “I’m not sure I’m gonna be able to pull this off.” But then last weekend, I sat and did a five-and-a-half-hour bike ride.
[00:28:31] OG: It’s like, okay, well- That’s not nothing. I gotta do that twice. I gotta do 11 hours, but- Yeah … at least I demonstrated I could do five and ha- You know what I mean? So, like, any time you do something, there’s gonna be a little fear factor moment, whether it’s money or anything. So I don’t know that it’s inherently bad to have that feeling, I guess.
[00:28:49] OG: I don’t know. For me, it’s a motivation piece sometimes, as long as it’s in bounds, right? If it’s like, bought a lake house and I really can’t make the next payment- Yeah … like, that’s stupid. But if it’s a stretch, like- Well, you and
[00:28:57] Joe: I both know a guy, we first started in financial planning, who bought a Porsche on payment specifically so that he would have to work really hard, which is ridiculous.
[00:29:05] Joe: Oh,
[00:29:05] OG: yeah. I was like, no, it was a different car. But w- I was thinking of a different person who also did the same thing. Who did- But I was thinking of a different car.
[00:29:12] Joe: Just not a, not a- But
[00:29:13] OG: I know who you’re talking about,
[00:29:14] Joe: yeah. Yeah, yeah, not a great reason to, uh-
[00:29:15] OG: But that was a sales, that was a sales culture thing at Ameriprise.
[00:29:19] OG: I was in that meeting when the regional vice president went, “Go buy something you can’t afford on payments, because it will force you to be a better salesperson by the end of the month.” ‘Cause you can’t have any bad marks on your credit, you get fired. So you wanna sell $1,000 of mutual fund commissions?
[00:29:37] OG: Have a $1,000 car payment due at the end of the month. That’ll motivate you. It’s so
[00:29:41] Joe: crazy.
[00:29:41] OG: It’s dumb.
[00:29:42] Joe: So dumb.
[00:29:42] OG: It’s ridiculously nuts, but it’s a sales culture.
[00:29:45] Joe: So absolutely dumb. Jesse Cramer, my first question for you is, did I say that I wanted these rapid fire out loud, or did, uh- … did I say that in my head- Sorry
[00:29:54] Joe: and OG just ignored it?
[00:29:56] Jesse: Sorry. Well, rapid is a relative term. I mean- I know … you know, i- in terms of the full time expanse- The entire expanse of all of
[00:30:03] OG: human time …
[00:30:04] Jesse: of the universe. Exactly.
[00:30:05] OG: That’s right.
[00:30:05] Joe: I
[00:30:05] OG: was pretty quick.
[00:30:07] Jesse: OG’s answer was just a flash in a pan.
[00:30:09] Joe: Yeah, I agree with the luxury car, but again, sometimes a luxury car isn’t that big a deal.
[00:30:15] Joe: Mm. It’s a luxury car with bald tires, where you can tell the person can barely afford it. Mm. Or I actually know somebody who is really irresponsible with money, has a beautiful luxury car, the Check Engine light’s always on, and hasn’t had an oil change in forever because they can’t afford it. Like, that’s over their skis.
[00:30:33] Joe: Jesse, you got another one?
[00:30:35] Jesse: Well, I, I grew up pretty rural, and again, y- in your intro, Joe, you did admit that some of our answers might be a little bit judgy here. Okay? Is
[00:30:43] Joe: it somebody with a really nice tractor?
[00:30:46] Jesse: Close. But, uh, I just remember sometimes you would see… It’s, it’s almost like this ratio. So you add up someone’s cars and their boats, and then you compare it to their house.
[00:30:57] Jesse: Oh. And there’s sometimes where you’re like, “Hey, we, I kinda know what’s goin’ on in your financial situation loosely,” and that’s $120,000 boat. Like, that’s w- might be the most valuable single asset you own, and the saying with boat ownership is, like, the two… Do you know this one? The two happiest days in a boat owner’s life?
[00:31:15] Jesse: Yeah. Yeah, yeah. The day they, the day they buy, the day they sell. So that’s one that always stuck out to me, which is, like, sure, if you’ve got, if you’ve already got more money, the, the 1/1000th fract- uh, fraction that you used earlier, Joe, like, if your boat is 1/1000th of your balance sheet, good for you.
[00:31:30] Jesse: But if your boat is, uh, you know, 25% of your balance sheet, you, you might-
[00:31:34] Joe: If your depreciating assets outweigh your appreciating assets-
[00:31:37] Jesse: Correct. Correct …
[00:31:38] Joe: yeah, it might be too far. Paula, you got one?
[00:31:42] Paula: Yeah, I… Well, in, in New York you often see people who they live in apartments that are nicer than what they can really swing.
[00:31:50] Paula: Yeah, it, it comes down to housing
[00:31:51] Joe: You mean they’re like 600 square feet instead of the 400 square feet?
[00:31:55] Paula: Yeah, exactly. Like- Or, you know- … what
[00:31:57] Joe: are you, Mr. Wealthy?
[00:31:58] Paula: A place with a doorman, an elevator building instead of a walk-up, a place with an in-unit washer, dryer rather than, you know, just going to the laundromat, that sort of a thing.
[00:32:06] Joe: Right, a place that doesn’t have like a pool table in the background- … with, uh, the, uh, snack bar and the pool and everything else in one place. All right. When we come back, we are going to dive into what do we do about it. What are the things that we do to actually, maybe if you’re feeling very tight, how do we relieve some of that?
[00:32:26] Joe: We’re gonna have that in a moment, but on our Friday show, we pause halfway through to dive into our year-long trivia competition. Doug, Mr. OG, is very close to record-breaking territory, but after his margin call last week, might be a little further away.
[00:32:43] Doug: Right. Right. Last week was a pretty exciting week on a number of levels, but our current champion, our current reigning champion, is this correct, Jesse?
[00:32:52] Doug: He, uh, he called a margin call and made things just a skosh less comfortable for OG. Right now as the scores sit, we have OG eight- Well, to be fair, I called
[00:33:02] OG: the margin call.
[00:33:03] Jesse: I think I, I defended myself from OG’s
[00:33:05] OG: blatant- Jesse defended the margin call …
[00:33:07] Jesse: blatant attack.
[00:33:08] Doug: Gotcha.
[00:33:08] OG: That is correct.
[00:33:09] Doug: That’s what it was.
[00:33:10] Doug: That’s what it was. A blatantly
[00:33:11] OG: telegraphed attack, no thanks to our esteemed announcer, but carry on.
[00:33:15] Doug: Uh-
[00:33:16] OG: Uh, but who’s remembering the facts? I don’t
[00:33:18] Doug: know, just- Uh, hmm …
[00:33:19] OG: whatever.
[00:33:20] Doug: Interesting. I don’t remember it quite that clearly.
[00:33:22] OG: You wouldn’t.
[00:33:23] Doug: Anyway, score is eight to five to three. That’s eight for OG, five to Jesse, and three for Paula.
[00:33:30] Joe: And as you just heard, my favorite part of the show, which is new this year, is the margin call because what’s a competition between longtime friends without a little dagger in your back? Here is the way this works. Each of our good-looking contestants gets one margin call per quarter. Much like a real margin call where your broker calls you, and they’re like, “Hey, guess what?
[00:33:49] Joe: You don’t have any money,” well, it, it takes you by surprise. So one contestant is going to yell, “Margin call,” but only if they have a little margin of their own to gamble. They have to have at least a point to gamble because here is the gamble. The person who gets called must get the point right, or they lose a point, and that’s the bad news for the margin caller.
[00:34:09] Joe: If they do successfully answer the question, the person who tried to lay the trap, well, they get trapped and lose a point. So can get, uh, pretty ugly if you don’t call the margin call on the right person at the right time. So a little fun, a little messiness, a little convolution to our show, but that’s what makes our Friday trivia fun.
[00:34:30] Joe: You know what makes it the most fun, though? Doug has a question for us every week. What’s the question, Doug?
[00:34:39] Doug: Hey there, Stackers. I’m Joe’s mom’s neighbor, Doug, and way back in 1977, the little computer that could, the Apple II, was released, and I have it on good authority that just 15 minutes later, the first hacker was furiously working to steal users’ identities. But today, no pessimism allowed. No way. It’s my job to counter this everything is bad even for the people who make a lot of money stuff.
[00:35:03] Doug: I get that we’re here on YouTube helping you through it all, but let’s grab you a little sunshine. Co-founder Steve Wozniak, or as we called him at our weekly pickup hoops game, the Woz, was just in the news after speaking at Grand Valley State University, where he told graduating Lakers that they already possessed AI.
[00:35:22] Doug: That’s actual intelligence. Wozniak is not the world’s first trillionaire for one reason. He sold much of his Apple stock back in the early days. Does he regret it? Believe it or not, he doesn’t. Here’s today’s question: What percentage of the company did Wozniak originally own as a co-founder? I’ll be back right after I find out just how much of my El Camino I own.
[00:35:47] Doug: I mean, you know, split between me and the bank
[00:35:52] Joe: All right, OG. We’ve got, uh, Steve Wozniak as a founder of Apple. What percentage of the company did he own back at the beginning? Uh, Wozniak’s from your hometown, isn’t he?
[00:36:03] OG: It’s so funny that you knew that. As a matter of fact, uh, not only is he from our hometown, but he was…
[00:36:09] OG: You guys were talking about mowing grass. I actually mowed his grass when, uh, he was my neighbor. And he always bragged all the time about this stupid computer company, and nobody really bought any of their computers anyway. So I think at the time he was probably pretty happy that he sold out of his position, but he didn’t sell out without making a fairly decent amount of money, so that’s good.
[00:36:30] OG: Compared to the other guy that was a founder, he was a total dumb A dollar sign dollar sign, as you know. Because he sold out, like, you know, kinda right away. So, um, this is not fair to these other guys because I’m dragging this out hoping somebody will margin call me because- … this guy lived next door to me, I know the exact number, and it’s really unfair.
[00:36:56] OG: But he is from my hometown. I knew him personally. He bragged about it all the time. He actually had a license plate on his car that said 45, and everybody thought, “What does that mean?” It’s, uh, the percentage of Apple that he originally owned. So he owned 45% originally.
[00:37:12] Joe: 45%. Jesse Cramer, what are you gonna do with that number?
[00:37:16] Jesse: I mean, it is unfair. OG literally strapped on himself- … to a mower in Steve Wozniak’s long, tall shrubbery, bushes, grass, et cetera. It is an unfair advantage. Uh, I j- I have no idea. I have no idea. You’re like, “Is it, is, was it Jobs and Wozniak, 50/50? Were there other people involved who you’ve never heard of?”
[00:37:39] Jesse: I am gonna go with the second one. I’m gonna say there was one person involved who we don’t know, and I’m gonna say they were a third, a third, a third. So I’m gonna say on day one it was 33.3 repeating
[00:37:51] Joe: All right. Well, we’ve got, uh, 45 and 33 and a third, Paula Pant.
[00:37:56] Paula: Ooh. Oh, that’s tough. Do I, do I shoot for the middle or do I take the under?
[00:38:03] Paula: ‘Cause I don’t think it would be over. ‘Cause I have to assume that they had some outside investors, and the outside investors would’ve had some, some type of an ownership interest.
[00:38:14] Jesse: If Paula doesn’t think it was 50/50, then I’m, I’m toast. Then I’m toast.
[00:38:20] Paula: I mean, my… Okay, so my two options really are either to take 44 or to take 33.2.
[00:38:30] OG: Or 46.
[00:38:32] Paula: Eh, I don’t think it could be. I think, I think 45 you’ve anchored the, at the highest it could be. I’m gonna go with 33.2.
[00:38:40] Joe: 33.2, which, uh, Jesse means you, you might be half toast, so.
[00:38:46] Doug: I think so.
[00:38:48] Joe: But who knows? Well, Doug knows. That’s a scary thought, but, uh, he’ll be back with the answer in just a moment.
[00:38:57] Joe: All right, OG, you kick this off at 45%. You feeling pretty confident?
[00:39:01] OG: Uh, very much so, yeah. Yeah, this one’s, this one’s in the bag unfortunately.
[00:39:06] Joe: He sounds pretty confident, Jesse. What are you thinking? He’s a
[00:39:08] OG: neighbor, had the license
[00:39:09] Jesse: plate. I, I have no idea. It’s a black box to me, which probably means I have a 33.33% chance-
[00:39:14] Jesse: of winning.
[00:39:15] Joe: You, you do. And it could have been thirds, and he’s been confident before, Paula Pant, so could be your day.
[00:39:23] Paula: You never know. I mean, a broken clock is right twice.
[00:39:28] Joe: Yours is broken a f- fair amount- Yeah … more
[00:39:30] Paula: than that. Yeah.
[00:39:32] Joe: Yes.
[00:39:34] Paula: I mean, if, ’cause i- if this were truly random, I would be winning about one third of the time, but my, my losing streak is statistically implausible, and yet-
[00:39:44] Paula: and yet, here we are.
[00:39:45] Joe: Yet it continues, right. Well, maybe not any longer. Maybe in about two minutes you’re gonna have a point in your favor, but only Doug knows. Doug, who’s taking home the point?
[00:39:59] Doug: Hey there, Stackers. I’m El Camino fan and guy who the bank said is only a short 12 years from owning that car outright, Joe’s mom’s neighbor, Doug. Today, we celebrate the creation of the Apple II computer, which was born on today’s date back in 1977. The company originally was founded by three people, the Woz, Steve Jobs, and a guy many forget, Ronald Wayne.
[00:40:24] Doug: Wayne was brought in as an older experienced administrator who knew how to create and read legal documentation, and also how to handle the partnership agreement. In a case of clearly underpricing himself, Wayne designed Apple’s very first logo, and famously sold his equity stake in the company for just $800 12 days after the company was founded.
[00:40:47] Doug: But how much equity did Wozniak own? Well, if Jobs owned 45 and Wayne owned 10, that means the Woz owned 11.8% more than what Paula guessed, 11.67 more than what Jesse guessed, and 0% more or less than what OG guessed, ’cause finally he was telling the truth. He knew this one exactly.
[00:41:11] Joe: Yeah, might not have happened in, uh, Bay City, Michigan.
[00:41:14] Joe: However, OG, taking home the… Y- you got your point right back after last week. Good work. And how about that, Paula? Selling at, uh, th- there’s a oops. Wow. Selling… And, and you thought your losing streak was bad. Imagine being the guy that sold his shares, 10% of the company- Sold Apple
[00:41:30] Paula: shares for $800. Wow.
[00:41:32] Joe: Yeah.
[00:41:33] Joe: Well, OG back on track, and, uh, we’re still not halfway through the year, so we will see if his March continues or if, uh, Jesse or Paula can margin call him. I’m surprised neither one of them did today, even right at the beginning, so.
[00:41:48] Paula: I, I don’t want to expose myself to that level of risk.
[00:41:51] Joe: Let’s move into the second half of our discussion.
[00:41:54] Joe: Paula, we were talking about this just before the break, that part of this, you know, might be a little bit psychological, right? This feeling of being broke. We talked a little bit about comparison culture. I also feel like OG had something though in this idea of never feeling caught up. Like, it’s so easy today to compare ourselves to other people, that maybe it’s not the economy as much as it might be our addiction to social media.
[00:42:17] Paula: Uh, I, I don’t know. I think social media is an easy scapegoat, but I think that it’s beyond that. You know, right now we have a, a situation in which expenses associated with daily living have gone up. Housing, transportation, food. Those have increased. And for people who own assets, our as- our paper assets, stocks, equity, and real estate, those paper assets are also doing well, but paper assets don’t impact free cashflow, right?
[00:42:50] Paula: There’s a difference between how good your net worth is performing, um, you know, how well your portfolio is doing, and your actual day-to-day free cashflow. And so I think that there’s… You know, part of the disconnect is you might be doing really well on paper, but the amount of life that your income can provide is getting tighter and tighter.
[00:43:13] Joe: Oh, gee, there are some expenses we can control, but, you know, the ones Paul is talking about, those are locked in. If we’re just gonna live, we have to go to the grocery store. So psychologically, how do we make this easier on ourself? I’m thinking that in some ways financial complexity creates stress, and this might be a good time for people to get rid of some of that financial complexity in their life.
[00:43:35] Joe: Like, I’m thinking, you know, how many people do you know that when they come to you for the first time they’ve just got way too many accounts? They’ve just got accounts all over the place.
[00:43:43] OG: I just read a line, um, I’ll s- I’ll get around to answering your question in a second, Joe. But I just read a line in an article that I was, uh, perusing from Financial Samurai about 10 million is not enough to retire on.
[00:43:55] Joe: Sam would never write a headline like that.
[00:43:57] OG: Well, his take was, “Yeah, it is. It’s frigging plenty. Stop being an idiot,” you know? Oh, was it? Okay. Like, yeah, yeah, that’s what he was getting to. But he said, uh, and I’m just gonna quote it so I don’t screw it up, “Lifestyle inflation is insidious because it doesn’t feel like inflation, it feels like progress.”
[00:44:13] OG: I thought that was a pretty cool way to think about this, you know, just, just kind of picking back up on the thing that you can control part of it. So circling back to your ans- or your question, Joe, about complexity, I think complexity shows up in a lot of different ways. I don’t think having a bunch of accounts is complex unless, you know, they’re unnecessary.
[00:44:34] OG: I think it’s very reasonable for a two-person household to each have Roth IRAs and to each have IRAs and to each have workplace accounts, and maybe have a brokerage account, or each have a brokerage account, depending on their net worth and the, you know, estate planning stuff. And then you add to that, you know, kids’ accounts, whether it’s 529 or, or education IRAs or kid Roth IRAs.
[00:44:55] OG: It’s, you know… And then layering in some bank accounts and high-yield savings accounts and credit cards and, you know. I, I think there’s an opportunity to clean those things up for sure, especially if you’re approaching financial independence. That makes sense. But if that’s your reason for, like, feeling overwhelm is because you can’t, you know, get Google Docs to make a spreadsheet that looks comfortable for you, I think there’s more to it than just that.
[00:45:20] OG: It’s not the financial accounts that are the, is the complexity. It’s everything else that’s around it that’s the complexity. It’s the fact that you have the lake house that you never go to or the parents that you’re supporting, and you can’t really put a finger on how much that costs, or the, you know, 33-year-old kid that’s still living in your basement.
[00:45:39] OG: Looking at us. You know, it’s hard to quantify, like, what is that doing to our life in terms of financial stress, and not stress literally, budget stress, but, like, just the complexity, like you said. The biggest thing that I see is just not having clarity around what they actually wanna do. If you can articulate what your goal is, it becomes so much easier to accomplish it because now you’ve put your mind to something that is got a start and an end to it.
[00:46:09] OG: If you just say something ambiguous like, “I wanna retire,” or, “I want financial independence,” but don’t actually quantify what that looks like, you’re sailing into the unknown. You don’t have any way to know whether you’re getting close or not.
[00:46:22] Joe: It’s funny, Jesse, I wrote that one down myself. Like, too many nebulous goals.
[00:46:27] Joe: I wrote down too many nebulous goals, too many accounts, too many subscriptions. We don’t need five different budgeting apps. We need fewer moving parts.
[00:46:34] Jesse: It certainly helps. I mean, I, I know some stories where people feel overwhelmed by complexity in that way, but if we’re talking about the concerns of the high earner today, I, I don’t know.
[00:46:44] Jesse: In my experience, that’s a little bit, it’s not quite hitting it on the nose Because like OG said, I think most of the conversations I’ve had before, people are reasonably comfortable, people are reasonably comfortable when they have lots of accounts. Like OG, what, what you just listed out, like what, a family might have 15 or 20 accounts between all the different types of investment accounts and bank accounts.
[00:47:05] Jesse: Mm. And I think as long as someone can see those accounts on one piece of paper, they’re like, “Okay, like I, I get it. It’s all right there.” I think it’s a lot more disconcerting when someone’s like, “Hey, our, our tax return says our top line income was $600,000 last year, and yet I really don’t feel like I saved that much money, and I can’t put my finger on why.
[00:47:27] Jesse: Like, where did it all go?” That to me is that kind of uncertainty complexity that really drives the kind of concerns we’re talking about today.
[00:47:36] Joe: Well, if we’re starting to dig into that, Paul, I make $600,000, I don’t know why I didn’t save more money, where do I look first?
[00:47:42] Paula: The first thing you do if that’s the case is track all of your spending.
[00:47:47] Paula: You know, so use some type of a program. There’s a lot of different software options that do it, but use some sort of a program that tracks. And, and you can do it retroactively as well by looking at old credit card statements. Start classifying things. You know, budgeting is often the calorie counting of personal finance, and I often talk about the anti-budget because calorie counting is not sustainable in the long term.
[00:48:08] Paula: But as a short-term maneuver, in order to get an assessment of here’s what’s currently going on, let’s take stock, you know, let’s assess, it can be very, very effective for targeted short-term assessment. So that’s where I would begin.
[00:48:23] Joe: We talked a lot about, um, you know, having stuff and actually enjoying it, OG.
[00:48:28] Joe: Is having some type of like a Marie Kondo joy audit in order? Like is this really lighting me up? Does this spark joy, as Marie Kondo says? It does, I keep it. It doesn’t, I let it go.
[00:48:39] OG: I mean, there’s so much to that. It depends on the moment, right? I can see there’s different seasons for me where spending money in different areas has better personal utility, like joy, than other areas, you know?
[00:48:53] OG: And I think that’s true for everybody. I mean, I’ll give you an example, Joe, for you, and it’s kind of a silly one. You’re probably not gonna be doing a lot of campfire sitting around, you know, with your Solo Stove in July in Texarkana. That’s just not the season for that. You don’t have a line item in your budget for wood delivery because it would be stupid, and that would be a bad use of money.
[00:49:14] OG: But if it’s 38 degrees at night in December, there’s probably not enough wood in the universe to-
[00:49:23] Joe: What
[00:49:24] OG: the… Why? Paul is laughing, not me.
[00:49:25] Joe: Why does everything have a…
[00:49:28] OG: There’s not enough wood in the universe to satisfy you, Joe.
[00:49:33] Joe: Oh, man
[00:49:33] OG: But you get what I’m saying.
[00:49:34] Joe: Well, but if our goal then, OG, so let’s give you a little p- pushback then, though. So if I … I- i- if my goal here is to build some margin, right? If my goal is to build margin, and I’m like, “Okay, well, I’m not gonna get rid of the Solo Stove to get rid of margin,” what do I get rid of?
[00:49:48] Joe: Where do I begin that journey?
[00:49:50] OG: It’s so personal. I, I don’t have a dog in the hunt here. I think you have to have a great understanding of what you’re actually doing. Using Jesse’s example of, like, “I make 600 grand, I don’t know if I saved enough,” I would flip that around i- the other way and say, like, “Are you sure you didn’t save enough?”
[00:50:05] OG: You might have. Like, if you’re on track for your goals, and this is where, like, having the goal thing identified is super important. If you’re on track, and s- on track means I’m saving $100,000 a year, and you save 100 grand, then you saved enough. Good for you. You got to go spend $300,000 on whatever the hell you wanted to spend on it.
[00:50:24] OG: And it’s not my job or any of our jobs to say, “Well, that’s stupid. You should save 150.” On the other hand, if your goals are you need to save 150 and you’re only saving 100, then I think it is our job to point … you know, put the mirror up and go, “Hey, man, you said that you wanted to do this stuff that’s gonna cost you 150 a year to save.
[00:50:43] OG: You’re only saving 100. Like, what’s, what are we doing? Are we changing the goal? Are we gonna try to make more money? You know, are we cutting some stuff?” And when you look at the stuff of what you spend your money on, I think it’s fair to, to analyze every single thing as a potential area for opportunity.
[00:51:00] OG: Just because you have the 2% mortgage and you go, “I’m, I’m landlocked, I can’t do anything,” but you’ve got a million and a half dollars of equity in your house, and you could move and have a paid-for house somewhere else, that counts. That’s, that is truly an opportunity that you have. Now, it may be a bad one because you go, “Well, I’m gonna move from the area where the money is to a area where there’s not.”
[00:51:21] OG: Like, you gotta evaluate that. I think we very quickly jump to, like, lifestyle or our personal opinions of where people spend money and say, “Well, that’s stupid. You should never have a car payment,” or, “That’s stupid. You should never have a country club membership,” or, “That’s stupid. You should never go out to eat.”
[00:51:36] OG: But, you know, what’s dumb for me to look at is normal for somebody else. Like- Well, but the issue is- … you have to evaluate this on your own sense …
[00:51:42] Joe: the issue is, is if I feel tight, right? I mean, that’s the whole basis of this discussion. Well,
[00:51:45] OG: then you owe it to yourself to evaluate yourself in the confines of yourself and go, like, “Do I really care about this stuff?”
[00:51:52] OG: And yeah, maybe you have too many subscriptions. So then
[00:51:54] Joe: it is spark joy. Then it is spark joy.
[00:51:57] OG: I mean, sure.
[00:51:58] Joe: Yes. You know. I just wanna hear you say spark joy. That’s all I was looking for.
[00:52:02] OG: I wanna go back to talking about …
[00:52:04] Jesse: Wood?
[00:52:04] OG: Woods.
[00:52:04] Joe: Oh. Can’t get there. Yeah. Uh, Jesse- Spark
[00:52:07] OG: wood … I just like … I just, I just like Paula giggling like a schoolgirl.
[00:52:12] OG: That sparks joy for me.
[00:52:17] Joe: Jesse, it’s interesting. So the case that OG’s building is start with some goals, make sure they’re what you really want, and the budget forms itself. You like that?
[00:52:27] Jesse: I, I do. I really like it, and I concur with one thing. Well, I concur with a lot of what OG just said, but one thing in particular is, like, y- you know, I’m curious if you feel the same way, OG.
[00:52:37] Jesse: If someone comes to you and they’re like, “Hey, uh, OG, I… We really think we want this boat,” what do you think about that, going back to boats? Sometimes when I get that question, I’m like, it’s not my job to tell you whether you are going to enli- enjoy owning a boat or not because now all of a sudden I’m layering on my predisposition, which listeners and you guys already know I’m anti-boat.
[00:52:58] Jesse: So you guys already know I’m
[00:52:59] OG: anti-boat, right? But you sound like… Do not ask Jesse for a boat. If you’re a client of Jesse’s, he’s gonna shoot your boat idea down.
[00:53:06] Jesse: Correct. Just do
[00:53:06] OG: the boat.
[00:53:07] Jesse: Tell him after the fact. If you want me to motorboat you, you know what my answer’s gonna be.
[00:53:10] OG: Oh,
[00:53:10] Jesse: boy. Uh, sorry. Uh, where was I?
[00:53:13] Jesse: Uh, no, motorboats would… I was talking about my job is to let you know, here are the options. Like, here are the goals you laid out to me. If you choose to buy this boat, here’s how it might affect your long-term goals. Like, I can help you understand the opportunity costs, and then you can make a more informed decision.
[00:53:28] Jesse: So I think what OG, some of what he’s getting at right here is, like, you know yourself, and you know a little bit of this subjective swirl that’s going around in your head about the trade-offs and the opportunity costs and what do you really enjoy, what do you not enjoy at all. A- and, sure, like, we can help you with some of the numbers, but we can’t really help you figure out all the subjective stuff or at least not that easily.
[00:53:50] Jesse: It kind of turns into some financial therapy, which I’m okay at, but I’m no expert. So the point is that, um, yeah, it, it has to be a bit of a two-way street where you know your own brain the best, and, uh, it might take some work to, to try to figure out what’s really gonna make you happiest spending money on in, in the long run.
[00:54:09] Joe: Let’s end this on a high note. Uh, Paula, what’s one thing Stackers can do this week to stop feeling so squeezed?
[00:54:15] Paula: Take a look at your fixed costs, those are the real needle-moving costs, and ask yourself if there is one major fixed cost that even though it’s gonna take months or maybe a year to move, is there one major fixed cost that you can reduce such that everything else becomes easier?
[00:54:35] Paula: That way you don’t have to, like, frequently make DoorDash decisions. You can make one big decision and be done.
[00:54:40] Joe: OG?
[00:54:41] OG: Well, I kinda wanna say something a little snarky, but I don’t think it’ll… I don’t, I don’t, I don’t think you’ll like it, Joe. I mean, if you’re feeling squeezed, just decide not to feel that way anymore.
[00:54:52] OG: This is an emotion more than anything. And if you literally are spending more money than you make, then that’s a problem. But if you’re feeling like you’re spending more money than you make, we’ll define whether or not you really are, and if you’re not, then you can just go to work to figure that out, whether it’s fixed expenses or increasing your income or saving, pulling back your savings to keep money in your checking account if that makes you feel more comfortable.
[00:55:17] OG: But I, but I, I would, I would… I hate the word feeling, ’cause it… OG have no feeling. OG just do.
[00:55:26] Joe: I do like that, though. You know why I like it? I like it because the number of times back when I was an advisor that people felt a certain way, and then we did the actual math, and the math was far different than what was going on- Yeah
[00:55:38] Joe: in their head. It helped change their feelings by doing the math.
[00:55:41] OG: Well, I mean, I was just thinking about the example that Jesse gave about the sa- how, “I feel like I’m not saving enough.” I would be like, “Feel like it? What are you talking about? Like, you saved $87,219. What is wrong with you? That is an insane amount of money to save.
[00:55:54] OG: That’s awesome. Good job. Feel happy. Like, this is amazing.” “Well, I feel like I should have saved more.” Feel happy, you idiot. It’s like, “Yes. Yes, you dumbass. Be happy.” OG mad.
[00:56:06] Joe: I think this is, seriously can be a problem in the personal finance community. Because how many times have we been… You know, you get the surround sound of people saving 50% of their income.
[00:56:14] Joe: You’re only saving 42% of yours, so you’re like, “Oh, my God, I gotta find something else to do.”
[00:56:18] OG: Yeah. I’m saving 50% of my $20,000 income. Meanwhile, I’m saving 10% of my million-dollar income, and I’m the one that’s the idiot.
[00:56:24] Joe: Right.
[00:56:25] OG: You
[00:56:25] Joe: know? Yeah.
[00:56:26] OG: Yeah. Like, okay.
[00:56:27] Joe: Jesse. Yeah. What’s- Well- That- On, on that note, I mean, comparison- I, I don’t, I don’t know where you go with that I don’t
[00:56:33] OG: play.
[00:56:33] OG: OG no play game. OG have no feeling.
[00:56:36] Joe: Yeah.
[00:56:37] Jesse: Two uber quick thoughts. One, comparison is the thief of joy, and that’s a truism that OG just hit on. And as for a tip or a takeaway would be the average American probably has, like, 60 or 70 plus line items in their expenditures on a monthly basis. And if you review last month’s expenditures in your, from your credit card or bank account or whatever, can you find one thing where you’re like, “Wish I didn’t spend that money,” and cut that out?
[00:57:02] Jesse: And I think sometimes just taking that step, whether it’s a $10 step or a $500 step, gets you motivated to keep moving in that direction if you’re feeling squeezed.
[00:57:12] Joe: Yeah, a frustration that I always had was when someone was spending a lot of energy on looking rich versus being rich, building wealth I think the goal is to build this life where your money supports your freedom instead of stressing you out.
[00:57:27] Joe: And if you feel like you’re stressed out, those might be, those might be flipped. You’re too worried about feeling instead of building that margin. Great discussion, guys. Thank you so much for having it and helping, hopefully, quite a few stackers, who apparently, according to Wall Street Journal, a lot of people feeling that way right about now.
[00:57:45] Joe: Let’s find out how else you’re helping them though. Paula Pant, what is going on over at that place you help tons of afforders at the Afford Anything show?
[00:57:54] Paula: Oh, well, on the Afford Anything show, Joe, you and I answer questions that come from our community. Then we cover all kinds of ground, ranging from budgeting to mortgage payoff.
[00:58:05] Paula: You know, do I prioritize this versus that? Asset allocation. I mean, we, we do it all.
[00:58:11] Joe: Yep. We help lots of afforders strap on better money habits. It’s what we do over at the Afford Anything show. There
[00:58:19] OG: it is.
[00:58:20] Joe: Oh, man. OG, what do you got going on this fine, uh, w- weekend, first weekend in June?
[00:58:26] OG: Uh, well, I have a after-school activity meeting, uh, Saturday, and then a, uh, copious amount of, uh, bicycle time as I, uh, saddle my you know what around, uh, the streets of DFW, so…
[00:58:40] Joe: Thank God it’s not hot in DFW in June.
[00:58:43] OG: Well, the good news is I do it at, like, 5:00 in the morning- … because it’s so frigging hot. That
[00:58:47] Joe: is the good news.
[00:58:48] OG: That’s the- That’s the great news. Waking up at 3:45 so you can eat and have coffee and all that sort of stuff, so you can then go sit on a bicycle for seven hours sounds like a great Saturday.
[00:58:56] OG: That’s why
[00:58:56] Joe: I’m so happy I’m not training for marathons anymore, where I’m getting up at 3:30 to- I know … beat the heat. Just ugly. It’s pretty
[00:59:02] OG: wild.
[00:59:03] Joe: Yes. Speaking of heat, heat in Rochester, New York, those two things go hand-in-hand, so I won’t ask you about that, Jesse. Let’s find out what’s going on at the Personal Finance for Long-Term Investors podcast.
[00:59:15] Jesse: I mean, we do have beautiful summers here. If you’re gonna visit Rochester or the Finger Lakes, come in the summer. It’s gorgeous. Uh, but what’s going on over on… What are we calling it, Doug? PFLY? P-FLITY? Something like that?
[00:59:27] Doug: Lately, I’ve been really warming up to FILTY. FILTY. Like, it’s just FILTY, baby.
[00:59:32] Jesse: FILTY.
[00:59:32] Jesse: Yeah. FILTY with a silent A. What a
[00:59:33] Joe: FILTY podcast.
[00:59:35] Doug: Yeah.
[00:59:35] Jesse: We’ve got… Uh, I just released the second part of a two-part series, uh, the 14 risks in retirement and what you can do about them. It’s using that Charlie Munger, you know, invert, always invert. So you start with the biggest risks, and then you figure out what you need to do to combat those risks.
[00:59:50] Jesse: So just dropped the, the second of the two parts of that 14 item list.
[00:59:55] Joe: Getting through all the battles. The best battle’s the one that’s never fought. I think I gotta say that once a week, Doug, d- on the show, don’t I?
[01:00:01] Doug: You do. If you’re not talking about E-Myth, you might as well do Sun Tzu.
[01:00:04] Joe: Better do Sun Tzu, right.
[01:00:05] Doug: Better do it.
[01:00:06] Joe: That’s gonna do it for today. Thank you, everybody, for hanging out with us. Thank you for everybody who hung out this, especially on YouTube today. If you wanna join us on YouTube- Head to Stacky Benjamin’s YouTube channel Friday… Excuse me, Monday afternoons. Monday we pretend it’s Friday here.
[01:00:23] Joe: I almost got that backwards. So join us on Monday afternoons. If you don’t get the 201 newsletter, our fantastic newsletter, we also send you an email that tells you what the topic’s gonna be and what particular time it is, but generally it’s at, uh, 4:00 PM Eastern Time. Do the math on where you are across the United States or ac- across the globe.
[01:00:42] Joe: 40, 49 different countries, isn’t it? How many countries, OG, listening to Stacky Benjamins?
[01:00:48] OG: 4,900, actually.
[01:00:49] Joe: 4,900 different companies, that’s right.
[01:00:51] OG: And it’s galaxies, by the way, not countries.
[01:00:55] Joe: Well, we have a galaxy of different things that you can take away from this show, but, uh, Doug always takes it down to the top three.
[01:01:05] Joe: Doug, what should we have learned on today’s episode?
[01:01:07] Doug: Well, Joe, first, take some advice from Jesse. Right now there are more things to spend money on than at any point in history, and he says, “Don’t. Like, just don’t, don’t do that. Don’t d- don’t do it.” Second, let’s review some words that came out of Paula’s mouth.
[01:01:26] Doug: If you can’t figure out why there’s too much month left at the end of your money, it’s time to start tracking your spending at a granular level. Maybe not forever, but at least long enough for you to get a handle on your habits. But the big lesson Don’t ask Joe’s mom about playing games on the Apple II.
[01:01:44] Doug: I really don’t think she understands computers because she started talking about visiting some castle called Wolfenstein and driving wagons down the Oregon Trail. Seriously, Ma, I wasn’t asking you for childhood stories. Are we gaming or not? Thanks to Jesse Cramer for joining us today. You’ll find his podcast, Personal Finance for Long-Term Investors: It’s Filthy, wherever you listen to finer podcasts.
[01:02:10] Doug: We’ll also include links in our show notes at stackingbenjamins.com. Thanks to Paula Pant for hanging out with us today. You’ll find her fabulous podcast, Afford Anything, wherever you listen to only the finerest podcasts. Fine, yeah.
[01:02:26] Joe: I think it’s
[01:02:27] Doug: be
[01:02:27] Joe: finerest.
[01:02:28] Doug: Be finerest. Thanks also to OG for joining us today.
[01:02:31] Doug: Looking for good financial planning help? Head to stackingbenjamins.com/OG for his calendar. Sorry, we’re running out of time. This show is the property of SP 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.
[01:02:55] 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.
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