You might not look rich on Instagram. That doesn’t mean you’re behind. Joe, Paula Pant, Jesse Cramer, and Anthony Weaver from About That Wallet work through eight real signs that your financial life is on track — covering stability, behavior, and mindset — and spend just as much time on why we’re all so bad at recognizing the wins we’ve already had.
What You’ll Walk Away With
- Why a $1,000 emergency fund puts you in the top 40% of Americans — and what Jesse’s registered nurse versus Uzbek architecture professor framework tells you about how big yours actually needs to be
- The debt-to-income ratio question nobody asks: would you rather have a 10% DTI and zero savings, or $1 million invested and a 45% DTI? Paula and Anthony work out their actual answers live
- Why someone making $250,000 and living paycheck to paycheck is less financially trustworthy than someone making $60,000 with a two-month buffer — and what that reveals about the real game
- Anthony’s dream walk framework: the questions he asks clients to make sure their day-to-day financial habits are actually pointed toward what they say they want
- Why the trend matters more than the number — and the one thing Jesse tracks monthly that most people miss when they’re focused only on net worth
- The peace of mind problem Paula names that most personal finance conversations skip entirely: there is very little correlation between the numbers in your accounts and your actual anxiety level
- Why Jesse thinks prioritizing stress reduction over optimization might actually produce better long-term outcomes than squeezing every percentage point
- The Instagram tell that almost none of the visible wealth you’re comparing yourself to is real — and the Tai Lopez rental strategy that proves it
- Anthony’s story about the client who needed permission to sell investments to feed her kids — and why money as a tool looks completely different at every income level
- Why money is the easiest possible scorecard — and how that ease is exactly what makes it so dangerous as a proxy for self-worth
Why This Matters Now
The comparison pressure has never been higher and the metrics have never been more visible. This episode is a reminder that the signs of real financial health are mostly invisible on the internet — and that you might already be further along than you think.
From the Basement
Joe, Paula Pant, Jesse Cramer, and Anthony Weaver from About That Wallet work through eight signs of financial progress from a wisdom.com piece while talking about drone footage FOMO, Tai Lopez’s rental Lamborghinis, and why somebody in Florida held a half-eaten grilled cheese sandwich for ten years before selling it on eBay.
Resources Mentioned
Stacking Benjamins BAD Groups — stackingbenjamins.com/bad
About That Wallet podcast — Anthony Weaver; available wherever you listen to podcasts
Afford Anything podcast — Paula Pant; recent episode with Dr. John La Puma on why going outside improves health and productivity
Personal Finance for Long-Term Investors (FILTI) — Jesse Cramer; recent AMA episode on retirement planning questions
Freedom app — referenced by Paula for blocking Instagram; freedom.to
Surfshark VPN — surfshark.com/stackingbee; code stackingbee for four extra months
Stacking Benjamins Vault — stackingbenjamins.com/vault
Stacking Benjamins Newsletter (The 201) — stackingbenjamins.com/201
Stacking Benjamins Community — stackingbenjamins.com/basement



Our Topic:
8 Signs You’re Winning With Money (… (2026) | @WhiteboardFinance (Wisdom.com)
During our conversation, you’ll hear us mention:
- Emergency funds
- $1,000 cushion
- Financial foundations
- Debt-to-income ratio
- Mortgage debt
- Good debt
- High-yield savings
- Job security
- Career risk
- Living paycheck-to-paycheck
- Cash flow gaps
- Retirement planning
- Dream walk exercise
- Lifestyle inflation
- Social media FOMO
- Instagram comparisons
- Highlight reels
- Private jet flexing
- Wealth signaling
- Status symbols
- Financial habits
- Automation systems
- Automated investing
- Retirement contributions
- Financial stress
- Peace of mind
- Net worth tracking
- Savings rate
- Income growth
- Money mindset
- Financial identity
- Money as a tool
- Values-based spending
- Financial progress
- Long-term trends
- Financial confidence
- Financial independence
- Financial education
- Building wealth
- Delayed gratification
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Anthony Weaver

Another thanks to Anthony Weaver for joining our contributors this week! Hear more from Anthony on his show, About That Wallet at ABOUT THAT WALLET – Podcast – Apple Podcasts.
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 visitingย The Best Interest โ Invest in Knowledge.
Paula Pant

Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paulaย on Twitter: @AffordAnything
Doug’s Game Show Trivia
- A woman in Florida sold a 10-year-old grilled cheese sandwich on eBay because she believed it contained an image of the Virgin Mary. What was the final selling price of the sandwich?
Mentioned in todayโs show
- Stacking Benjamins – Surfshark (promo code: stackingb to get 4 extra months of Surfshark VPN service)
- Freedom | Block Websites, Apps, and the Internet (Not an affiliate. Paula mentioned she uses it)
Join Us on Monday!
Tune in on Monday when we help you solve problems resulting from summertime credit card spending.
Miss our last show? Check it out here: Helping Mom With Money Before It’s Too Late (SB1853).
Written by: Kevin Bailey
Episode transcript
[00:00:00] Doug: Uh, hey everyone, just a reminder to tell Joe’s mom she looks like she lost weight, ’cause I accidentally parked
[00:00:09] Doug: on the grass again.
[00:00:11] opener: Hey guys, mics are hot. Quiet on the set
[00:00:22] Doug: And from the basement of the YouTube headquarters, it’s The Stacking Benjamins Show
[00:00:37] Doug: I’m Joe’s mom’s neighbor, Doug, and what are the signs you’re actually winning with your money? Today, we’ll detail eight ways you’ll know you’re on the right track. But that’s not all. Halfway through this extravaganza, we’ll have some fun seeing which of our contributors will win this week’s trivia question.
[00:00:55] Doug: And now, a guy who’s excited to help you win with money eight days a week, it’s Joe Saul-Sehy. Eight days, Joe.
[00:01:08] Joe: Hey there, Stackers, and happy, happy, happy Friday. So happy that you’re here with us, that we’re actually doing this. Doug, uh, happy Friday to you, my friend. How are you doing?
[00:01:20] Doug: Thanks, Joe. Thanks, Joe.
[00:01:21] Doug: Lovely of you to say so. I am enjoying this afternoon, and I hope you are, too. Hope you are well and everybody in your home is happy.
[00:01:29] Joe: God bless us, each and every one Who the heck are you?
[00:01:35] Doug: Birds are singing. Butterflies are flitting about. Children are playing and, oh, there’s a warm feeling of love embracing us all.
[00:01:43] Joe: Are the birds singing in New York City right now, Paula Pant?
[00:01:47] Paula: I don’t think I’ve ever heard a bird here. I’m sure in Central Park there must be some.
[00:01:51] Joe: I’ve never heard a bird in New York City. There are, like, too many people, I’m out of here.
[00:01:56] Paula: Well, I’d say it’s just, it’s, there’s a lot of traffic and a lot of people, and, I mean, again, in Central Park I’m sure it’s different.
[00:02:02] Paula: It’s just, you know, outside of my window I don’t exactly get birds. It’s
[00:02:05] Joe: just not right there. A place where there’s lots of birds, uh, flitting about. Mr. Jesse Kraber is here. How are you, man?
[00:02:12] Jesse: Hey. I’m doing well. I’m looking out a window right now, beautiful blue sky, a bluebird day. I think they call it a bluebird day, actually, not a cloud in the sky.
[00:02:21] Joe: Is it a bluebird day? I don’t know. It’s a bluebird day for us. You know why, guys? Because a friend of mine who I’ve… Every time I see him I’m like, “We gotta get you on the show. We gotta get you on the show,” and then for whatever reason our paths go different ways and he’s not on the show. He’s finally on the show today from About That Wallet, Mr.
[00:02:39] Joe: Anthony Weaver joins us. How are you, man?
[00:02:42] Anthony: Hey, I’m doing good. I mean, y’all talking about birds, home of the O’s and the Ravens over here, so it’s actually pretty fun. Th- th-
[00:02:48] Joe: that’s right. You are bird capital of Baltimore.
[00:02:52] Anthony: Oh, yeah.
[00:02:52] Joe: Absolutely. I’m coming to see you, by the way, uh, you don’t even know this, but in, uh, uh, just after 4th of July.
[00:02:58] Joe: I’m gonna finally get Camden Yards. I’m a baseball fan. I’m finally gonna see Camden Yards for the first time.
[00:03:04] Anthony: Nice. Well, make sure you get ready for the squeegee boys, that’s all I gotta say.
[00:03:07] Joe: Perfect. Fantastic. Well, tell everybody about About That Wallet. I love what you do, and, um, you have a great show.
[00:03:14] Anthony: Oh, yeah.
[00:03:14] Anthony: Thank you. So about my show, it’s really to help the Sandwich Generation build strong financial habits so that they can talk about money, spend money, and really enjoy their money with confidence, so just try to give them practical exercises that they can use every day after every episode.
[00:03:28] Joe: It is super, and you can find it on YouTube, you can find it wherever you find finer podcast.
[00:03:34] Joe: So super happy you’re here, and we’re gonna be talking about eight signs you’re doing very well with money. I’ve got four signs for doing well with money. Doug, Paula, Anthony, and Jesse. There’s four right there that you’re hanging out with us, and we have many more because we’re doing this live on YouTube, so we’re super happy that you’re here, and we’re gonna surf into today’s discussion, sponsored by, wait for it…
[00:03:58] Joe: Jesse, guess who today’s discussion is sponsored by?
[00:04:02] Jesse: Uh, State Farm Uh, a bird. Uh, Doug’s wallpaper
[00:04:07] Joe: Surfing into it’s Surfshark. Stop.
[00:04:10] Jesse: Surfshark. That was gonna be my fourth guess.
[00:04:12] Joe: Yes, if you’re like us, you’re spending a lot of time online right now watching the financial markets bubble. You need to turn that stuff off.
[00:04:18] Joe: Watching talking heads, turn that stuff off. Maybe talking yourself into the Lions winning 11 games this fall, Anthony, instead of the Ravens. We don’t need the Ravens to win 11. How about the Lions? Much better to focus on that. But while you’re doing that, your data’s basically out there for anybody to grab, and that’s where Surfshark comes in.
[00:04:38] Joe: Uh, Surfshark’s 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 brokerage account on airport Wi-Fi… I just, I, I can’t imagine doing that. But with Surfshark, I can’t imagine doing that, because your info stays private.
[00:04:55] Joe: Think of it like having an insurance policy before you step onto the internet. You’re protected. And 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 the people at Surfshark aren’t tracking what you’re doing either.
[00:05:11] Joe: Plus, features like CleanWeb block ad to malware before they even hit your screen. So if you wanna browse smarter, maybe even find better deals on travel or online marketplaces by changing your virtual location, go to surfshark.com/stackingbee or use code stackingbee at checkout to get four extra months of Surfshark VPN.
[00:05:31] Joe: That’s surfshark.com/stackingbee, code stackingbee. Jesse, you got that?
[00:05:38] Jesse: Got it.
[00:05:39] Joe: All right. Well, we got a great show. We got a couple more sponsors who help us keep on keeping on. We’re gonna hear from them, and then Anthony, Jesse, Paula, Doug, and I, we’re gonna help you guys make sure that you are doing great with money by checking eight different ways
[00:06:05] Joe: Our inspiration for today came to us from a piece that I found, Eight Signs You’re Winning With Money from wisdom.com, even if it doesn’t feel like it. Says, “You might not look rich on Instagram. That doesn’t mean you’re behind. Small wins add up to real financial strength.” And I guess, Paula, what I like about that statement is it’s ear- easier than ever for us to get FOMO, right?
[00:06:25] Joe: Because we compare ourselves with everybody else’s best moments, and I don’t know about you, but sometimes you’ll scroll, and that just depresses you.
[00:06:31] Paula: Yeah. I think the number one thing to do is block yourself from Instagram for a little while. I installed the Freedom app on my phone, and initially I blocked myself from Instagram just from 8:00 PM to 9:00 P- uh, uh, 8:00 PM to 9:00 PM was the only window of opportunity.
[00:06:45] Paula: And what that- I was
[00:06:46] Joe: gonna… I thought you were gonna say it’s the only time you’re blocked. From 8:00 to 9:00, I’m not on Instagram, but the rest of the
[00:06:52] Paula: day… 23 hours a day. That was my only window of opportunity. But what that meant was that I would look at the clock, and it would be, like, 9:17 PM, and I’m like, “Oh, darn, I missed my window for today.”
[00:07:05] Paula: ‘Cause, you know, it’s not like I’ve, I have a calendar reminder at 7:55. Oh, but that’s great,
[00:07:08] Joe: though.
[00:07:09] Paula: Yeah, exactly. And so that was how I initially did it, and then eventually that just led to- Just being off for several months. So anyways, to go back to your point about sometimes you think that you’re not doing as well ’cause you’re comparing yourself to people at Instagram, I mean, selection bias, sampling bias, like the way to get away from that is, uh, remove yourself from the distorted pool by just removing yourself from Insta.
[00:07:33] Joe: Well, there’s things when you go to Instagram, Anthony, that make people think, make all of us think, “Well, you’re wealthy because you look wealthy.” Let’s walk through with everybody, and I’ll start with you first. What are some of these signs that are ostentatious displays of wealth that maybe aren’t real?
[00:07:50] Joe: Like y- y- you, you might not be really wealthy even though you’re trying to brag that you’re wealthy.
[00:07:55] Anthony: Oh, yeah. One of the things that I always see, ’cause I like to travel, and you know when you see, like, those nice, uh, drone footage of, like, the greenery, and you see the water is blue, and you’re just sitting home on your couch and just be like, “Man, I wish I could be there.”
[00:08:11] Joe: Yes.
[00:08:11] Anthony: That is one of those moments where you’d be like, “Well then, how did you do it?” They never explain how they did it, and you think like, “Man, I really need to spend some money right now and buy my plane ticket,” and then you do not get the same experience. And that is one of the things that gets me every time.
[00:08:26] Joe: Yeah, they’re c- th- they’re coloring the viewpoint. They’re, they’re getting this perfect shot. You can’t see the landfill behind them. Right. It’s, uh… Yeah, yeah, something different. Jesse, what’s another Instagram groaner, ostentatious display of wealth that might not be real?
[00:08:41] Jesse: Oh, I feel like there’s so many.
[00:08:42] Jesse: It’s just like, it’s a, it’s a highlight reel, right? It’s just a nonstop highlight reel of all the best things, all the coolest things, all the prettiest places, the prettiest people. Makeup is on. Muscles are pumped. Windows out of the private jet are extra shiny. It’s like watching the top 10 on SportsCenter.
[00:08:58] Jesse: If all you do is watch the top 10 on SportsCenter, you will get a false understanding of what sports look like. And I don’t know, I, I don’t spend much time on Instagram and but when I’m there it’s like all you see is, uh, versions of everybody’s individual SportsCenter top 10.
[00:09:14] Joe: Doug?
[00:09:14] Doug: I, when he said private jet, I just…
[00:09:16] Doug: I groan and roll my eyes every time I see the 23-year-old walking onto a private jet like- Yeah … they f- like it’s theirs and like they own it. Come on.
[00:09:24] Joe: Well, and is that, isn’t that, uh, there’s a jet in Los Angeles, isn’t there, that you can rent- Yes … for not very much money to make it look like you have a private jet?
[00:09:32] Joe: It’s like in a studio. Yeah. In
[00:09:33] Jesse: the chat, they’re asking me where I am right now ’cause it looks different. I’m in a private jet.
[00:09:37] Joe: You’re in a private jet?
[00:09:38] Jesse: I’m
[00:09:38] Joe: recording. You have a, a private jet with a drop ceiling.
[00:09:40] Jesse: That’s correct.
[00:09:42] Joe: It’s pretty- That’s correct. It’s pretty amazing.
[00:09:43] Jesse: This is the kitchen. This is the kitchenette.
[00:09:45] Joe: But I remember, uh, that guy, you guys remember that guy Tai Lopez? Oh, yeah. Tai Lopez-
[00:09:48] Jesse: Oh, yeah …
[00:09:49] Joe: by the way, who’s… We did a story, Doug, just a few weeks ago, under investigation with the SEC right now, yeah, for some- Yeah … pretty serious stuff. But- Shocking … when Tai was starting out, he would rent, uh, Lamborghinis, Ferraris, and expensive mansions to do his videos.
[00:10:04] Joe: You know, he’d rent it for an hour just so he could stand in front of it, and you would assume that it was his place. Like, that’s awesome. So those are not the ways that we’re gonna be talking about wealth. Let’s do number one. Number one is you can handle $1,000 emergency. That is sign number one that you’re doing really well.
[00:10:22] Joe: How come, Anthony?
[00:10:23] Anthony: First off, you gotta think about it that it’s not such of a burden, and realizing that almost 60% of Americans can’t even handle $1,000 emergency fund right now. And if you think about it, $1,000 can really go a long way. I mean, when you really… Even with the inflation and still, like, you can still get a, a tire replaced, you can get, um, your kid that actually come to you for that last minute when they say, “Oh, I got a field trip around the corner.”
[00:10:50] Anthony: You’d be like, “Yo, why didn’t you tell me- … last week-
[00:10:53] Joe: No, it’s tomorrow, Anthony … when we could’ve had that $1,000?” It’s tomorrow.
[00:10:54] Anthony: Yeah, it’s tomorrow, right, and you gotta find your last $20. But it’s okay. You’re gonna make it work.
[00:10:59] Joe: Yeah, it, it is interesting, Paula, that 1,000 bucks gets you in the top top 40 percentile.
[00:11:06] Joe: Like, that’s all you gotta do. Like, that’s a huge win.
[00:11:08] Paula: I think this is where people, people who can cover $1,000 emergency, even if you might feel financially stressed in other areas of your life, like, take some time to appreciate how far you’ve come because the stats are that the majority of Americans could not cover a $400 emergency.
[00:11:26] Paula: So if the majority can’t cover even $400, then if you have enough money to be able to cover 1,000, you are doing better than most Americans.
[00:11:35] Joe: Jesse, but $1,000, I mean, it is a good start, and that’s what we’re talking about today are s- some of these motivational baby steps, right? These little things that we can do.
[00:11:45] Joe: But where do we really want that emergency fund to be?
[00:11:48] Jesse: Uh, where do we want it to end up being? Uh, different strokes for different folks. I’ve heard, you know, pretty consistently I feel like you hear three to six months’ worth of expenses. So if your household spends $8,000 a month, right, three months of that is 24 grand, six months of that is 48 grand, which is a big number, and it’s a lot a bigger of number than the $1,000 kind of starter emergency fund.
[00:12:08] Jesse: And- For what it’s worth, if there are just some, maybe some, a practical takeaway that listeners might help is one of my tidbits that I’ll tell people is to evaluate your own personal job security and, and your own personal ease with which you could find a replacement job if you needed it. So for example, if you’re, like, a registered nurse, which is, you can work in a lot of different places, they’re pretty highly in demand, you’ve probably got some good job security, and you could relatively easily replace your job if, for some reason, you lost it.
[00:12:36] Jesse: You could probably get away with a smaller emergency fund. But if you’re one of the 20 professors in the United States who’s studying Uzbekistani architecture, there might be only so many professorial positions in the world where you could go find your replacement job, and you might need more time to replace your job if you need it, which you might need to have a, a bigger emergency fund in that place.
[00:12:57] Doug: Did Uzbekistani architecture, did that just roll off your brain?
[00:13:02] Paula: I think it would be Uzbek. Uzbek architecture. Uzbek
[00:13:05] Jesse: architecture. Well, see, that’s actually a very hot topic in the Uzbek, Uzbekistani architecture scene, Paula. If you were one of the 20 professors, you would know that.
[00:13:16] Paula: Well, well, but if that professor had tenure, then they’re covered.
[00:13:20] Jesse: It’s true.
[00:13:21] Paula: Then they can spend down that emergency fund. I
[00:13:23] Jesse: believe it’s tenure.
[00:13:28] Joe: Let’s talk emergency funds, because if you get to Anthony, that larger emergency fund that Jesse’s talking about, that’s a lot of money sitting at no interest rate. How do we get that interest rate up a little bit?
[00:13:37] Anthony: Uh, yeah, so I wanted to go back ’cause Jesse talked about just having that six months, but really you gotta think about your profession as well.
[00:13:44] Anthony: Because definitely in a tech field, it’s always tough to find that job within that next three to six months if you’re out of a job because of high demand and AI that’s coming through.
[00:13:52] Joe: Where you’re in Uzbek tech. Uzbek. Oh, Uzbek tech. Yeah.
[00:13:56] Anthony: You can make it happen. And on top of that, a place to actually put it was, one of the things is a high yield savings account.
[00:14:04] Anthony: We gotta definitely lean into those. There are so many out there, and you just don’t wanna put it in the big banks where you’re only getting 0.01%, uh, so that it can actually grow a little faster, um, really have that moment so it can actually be a true emergency fund if things really hit a rye depending on your career.
[00:14:23] Joe: Yeah, I like that, having it separated away from your day-to-day spending money. And it’s funny that, uh, Bank of America in a recent uh, quarterly earnings report said the part out loud, they don’t pay more on their savings accounts ’cause nobody asks for it. Like, they, they said the quiet part out loud. Like, “No, we, we don’t care ’cause people don’t demand it.”
[00:14:42] Joe: So I would be all over the high yield savings account. Sign number two on this list, your debt to income ratio is under 36%. Jesse, when you saw that one, what was the first thing that came into your mind?
[00:14:54] Jesse: I know that the 36% number is widely cited. I know it’s, like, part of the CFP curriculum is like, all right, we draw, we draw this one line at 36%, we draw another important line at 28%, another one at 20%.
[00:15:06] Jesse: So that’s well and good. I still think those rules of thumb are… Well, they’re just rules of thumb, right? They’re very broad, generic, kind of one size fits all, and I think it’s very possible to have, uh, less debt and still kind of be in a precarious position. It’s probably possible to also have more debt than that and find yourself in a reasonably okay position.
[00:15:26] Jesse: That one might be a little less likely. But I guess my, my point is that, you know, it- it’s hard to just take that one rule of thumb and be like, “Oh, I’m, I’m only at 35%. I’m golden. I’m great.” I, I wouldn’t necessarily draw that conclusion.
[00:15:40] Joe: So you’re saying that somebody could have a great debt-to-income ratio and still be a hot mess?
[00:15:45] Jesse: Yeah, yeah. Or at least, like… Okay, well, you just said great, Joe. Like, if someone’s got, like, no debt, wonderful. But what… I guess what I’m saying is, like, if you draw the number 36 and you say below 36 you’re okay, and someone’s out there at 35.5- Right. I see what you- I, I still would want to know more about their situation- Yeah, yeah
[00:16:03] Jesse: to see if they’re okay. That’s what I’m saying.
[00:16:04] Joe: All right, Paula, so here’s kind of a fun question. Would you rather have a 10% debt-to-income ratio, right? Mm-hmm. Very low debt, but no savings, or a 45% debt-to-income ratio and a huge investment portfolio?
[00:16:17] Paula: Ooh, how big is the investment portfolio?
[00:16:21] Joe: Uh, let’s say, uh, you’re 35 years old and…
[00:16:25] Joe: $1 million.
[00:16:28] Paula: And you said 45%
[00:16:30] Joe: debt-to-income ratio? 45% debt-to-income ratio.
[00:16:32] Paula: Oh, man. I think I’d rather go the opposite. I think I’d rather do the 10% DTI.
[00:16:37] Joe: 35 years old. Well- No savings …
[00:16:39] Paula: oh, geez. Okay. Hmm. Oh, that’s a tough one. You know what? I would need to math this out. Think I need to math this out depending on what my income is.
[00:16:48] Paula: I need, I need, like, 10 minutes with a spreadsheet.
[00:16:50] Joe: But that is the question, right? I mean, one big question on that spreadsheet would be, I think, what type of debt is it?
[00:16:55] Paula: Yeah, uh, ’cause we’re talking zero net worth? 10% DTI and zero net worth? Okay, I change my answer. I think I’d rather have the one mil-
[00:17:02] Joe: And the 45%
[00:17:02] Paula: I’d rather have the one mil with the 45, yeah. Yeah. Final answer, one mil with 45.
[00:17:07] Joe: Well, what type of debt it is, I think brings up something, Anthony. You know, a lot of people look at mortgage debt differently. Do you look at mortgage debt as, quote-unquote, “good debt”?
[00:17:17] Anthony: Debt is debt, whether which way you look at it.
[00:17:19] Anthony: It depends on the game plan. Um, if your systems are set up properly to actually pay it off if things go awry, sure, have it as all you need to. But honestly, it… Like I say, it’s still an asset, or an also a liability if you’re living in that house. If it’s an investment property, it’s another thing because it depends on location, if you can sell it, if the bank even want it when you’re trying to sell it.
[00:17:41] Anthony: If nobody wants it, then what you gonna sit here with a empty house? Uh, I’ve heard so many different stories about when it comes to real estate, so- Eh, it depends. That’s probably
[00:17:55] Joe: right Just like, I swear to God, just like everything in personal finance, it totally depends. Number three on this list, you’re not living paycheck to paycheck.
[00:18:03] Joe: We’re talking about foundations, Paula, and for me this actually took quite a long time ’cause I was so bad with money that getting out of that paycheck to paycheck lifestyle changed everything for me. But what was the first thing you thought when you saw this as number three on our list?
[00:18:18] Paula: At the lower end of income it is almost inevitable for paycheck to paycheck living to emerge because you can only shrink s- you, you, you can only shrink down so far.
[00:18:30] Paula: Like, there’s a certain base under which, like, your food cannot get any cheaper. Like, rice and beans from Costco, still it has a certain floor And so I think a lot of times this needs to be contextual to how much you’re making, because it is one thing to be not making very much and be paycheck to paycheck.
[00:18:50] Paula: It’s another thing to be making a lot, but spending in a discretionary way a lot.
[00:18:56] Joe: I feel like this couples nicely, you know, like, like I’m thinking of a good wine with a nice meal, Jesse. Like, this couples well with that $1,000. You got $1,000 in the bank and you’re not living paycheck to paycheck, you’ve got a nice little foundation to begin from.
[00:19:10] Jesse: Definitely. And foundation, I think, is the perfect word for it, ’cause again, it’s having these things doesn’t necessarily mean that you’ve built a skyscraper yet. It doesn’t even mean that you’ve built a, a one-story house yet. But it does mean that you’ve got a solid foundation from which to build from.
[00:19:27] Jesse: And especially it’s just like not having these things in place is a precarious, it’s a scary place to be, right? Mm-hmm. Living paycheck to paycheck is a scary place to be. So it’s almost like, uh, was, is it Maslow? Is it the hierarchy of needs? Yeah, hierarchy of needs. Where it’s like- Right … right? And I, I almost feel like in, in a financial sense, like some of your hierarchy of needs are get past the point where you’re paycheck to paycheck.
[00:19:48] Jesse: Get to the point where you have a s- $1,000 emergency fund just to get by. Like there’s, there’s a similar tone to these things, just because what you’re doing is you’re eliminating some of these like lowest hanging emergencies that can strike you in a way, where it’s like, “Okay, if I have shelter, and I have heat, and I have some food, at least I’m, I’m, I’m okay a little bit.”
[00:20:06] Jesse: I think is, that, there’s some Maslow in there. So I, I kinda see some similarities between the two.
[00:20:10] Joe: I got those two things in order in my life, Anthony, and life just started picking up. A, I felt really empowered, but B, it was such a solid foundation. Let’s say you’re coaching somebody. They have the 1,000 bucks in the, in the bank.
[00:20:24] Joe: They’re not living paycheck to paycheck, which means now they have some discretionary income to start saving. What’s the first thing that you do to build on this platform?
[00:20:34] Anthony: All right. So you say they don’t have debt?
[00:20:36] Joe: They got a great debt to income ratio. Okay. So let’s just take the three things that we’ve got.
[00:20:40] Joe: Debt to income ratio looks solid. They’ve got $1,000 emergency fund, and now they have, they also have, uh, not living paycheck to paycheck.
[00:20:49] Anthony: Okay. So with the Because their debt-to-income ratio is still kind of there, even though you say healthy, I still would like to know what that debt is, going back to what Paula was mentioning.
[00:20:58] Anthony: Mm. Mm-hmm. It’s like really the layout of their foundation. Then really I will start looking into the habits, and I’ll talk… I walk them through what I call is like a dream walk. I call it the dream walk, where they say, “What does retirement look like? What are you doing now that actually can align to your future needs that would actually help fund that?
[00:21:15] Anthony: Are you taking action now? Are you investing in yourself? Are you taking an education to learn what it takes to do what you wanna do in your future? Are you having a separate account in your high-yield savings account to make sure that you are saving for those actual fun events so it doesn’t impact you?
[00:21:32] Anthony: And then also, what are the mitigations that you’re missing or overlooking so you don’t go into a higher debt-to-income ratio?” Those are the things I’ll kind of talk to them for, just kind of even though they have the foundation right, but still set up those barriers and rules for their friends and family that will kind of sneak in when they start talking about the vacations that they’re having.
[00:21:51] Joe: I like that, because then we’re setting actual parameters on what we’re saving toward, and not just saving it into some random bucket, which would be much easier, much easier to stop. Uh, we played a game earlier with Paula about would you rather have this or that. Anthony, how about this one? Who would you trust more financially, somebody making 60,000 bucks and they have a two-month buffer between them and paycheck to paycheck, or somebody making $250,000 and they’re living paycheck to paycheck?
[00:22:21] Anthony: I’ll trust the $60,000 person any day, ’cause they, they know what they wanna do with their money, and they pretty solid, which means that I can… If I were to give them the same paycheck as a $200,000 person, best believe they will still probably live the same lifestyle as if they had that 60,000, and maybe they might splurge and get, like, a nice, uh, cashmere sweater or something.
[00:22:40] Anthony: Uh, uh, from
[00:22:42] Joe: Quint, Paula.
[00:22:43] Anthony: Yes.
[00:22:44] Paula: Wow, who
[00:22:47] Joe: knew? When we talk about this stuff, you know, the person with $250,000 and no emergency fund, they’re living paycheck to paycheck, it would be easy for me to believe that person might not be thinking about their values when they’re spending. True, false?
[00:23:05] Anthony: True. Paula?
[00:23:06] Joe: Paula. That’s all right. We got Anthony’s.
[00:23:08] Joe: Anthony says true.
[00:23:10] Paula: So the question is might not be thinking about… This is, this is again with the negative. Yeah. Okay, so it’s true that they’re not thinking about their values. Is it true that they are not thinking about their
[00:23:17] Joe: values? Is it
[00:23:19] Paula: true it, okay, yes. True that they are not, yes.
[00:23:22] Joe: Yeah.
[00:23:24] Paula: The negative and sometimes the double negatives that they can…
[00:23:27] Joe: I, I have a habit of that, don’t I? I, I totally do. By the way, for people not here live, Andrea hanging out with us on YouTube says, “Kind of distracted by the workout class going on behind Paula right now as we record.”
[00:23:41] Paula: I’m just trying to inspire people to get to the gym.
[00:23:43] Joe: That’s right. Fit- fitness and finance go hand-in-hand.
[00:23:47] Paula: Exactly. N-
[00:23:48] Joe: number four here, we started off, Jesse, with Instagram, but number four is you stop comparing yourself to others. I think psychologically this is a big one.
[00:23:55] Jesse: Yeah, and I’m, I’m reading through it right now. Build the life you want, not someone else’s highlight reel. It’s so true. It’s, um… I, I just, I, I see it in my own life, and sometimes I feel it myself certainly, which is like, “Why do I want to buy that thing?
[00:24:11] Jesse: Why do I want to go to that place? Why do I feel the need to spend money on this or that or the other thing?” And a lot of times there is that comparison, you know. It’s so human. It’s part of our psychological makeup. It’s part of the whole social primate thing, is comparison. And in a lot of ways, we, we want to fit in.
[00:24:27] Jesse: We need to fit in. It’s not like you wanna make yourself a total social outcast via your personal finance choices. Doug, I feel like you can back me up on this one. But at the same time, there are certainly ways where your desire to not be a social outcast via personal finance choices can get yourself into personal finance trouble.
[00:24:47] Jesse: And so it’s kind of about finding that happy medium where, um, you’re still making really smart, even, like, you know, optimal… You’re making 98th percentile personal finance choices while still being a normal social primate.
[00:24:59] Joe: What do you mean that that can lead you into trouble? You mean you become such an outcast ’cause you just do nothing?
[00:25:04] Joe: Yeah. ‘Cause you do absolutely nothing, it leads to… Like, you become a curmudgeon who’s never doing anything?
[00:25:09] Jesse: Correct. You become a curmudgeon. You’re wearing old, crusty clothes. Uh, not only are you eating rice and beans, but you’re being outwardly critical of others who choose not to eat rice and beans. I mean, I’m painting a very, um, kind of-
[00:25:22] Joe: Stark
[00:25:22] Jesse: goofy picture here. Yeah, and then, like, probably an unrealistic picture. But yeah, there, there are ways where, like, curmu- I mean L- Scrooge. The whole story of, uh, what is it? A Christmas Carol. Charles Dickens and Scrooge is like, here’s a wealthy guy who didn’t spend any money and, and became a total social outcast because of his, it’s not even frugal, but yeah, like, curmudgeonly attitude.
[00:25:42] Jesse: So I don’t think that’s an outcome that we necessarily want.
[00:25:44] Joe: How the hell do we have no Dickens references for 10 years, and then we have two in the same episode? Like, what are we what are we doing with the Charles Dickens stuff today? I got no idea. But Anthony, what Jesse’s talking about, you know, you mentioned the drone footage earlier, right?
[00:25:59] Joe: The FOMO that you get from Instagram, watching somebody in this beautiful location that you wanna fly to. Like, asking yourself why I wanna do that is, is huge.
[00:26:08] Anthony: Yeah, I can say even with the… Just because of the scenery that you see, it’s like almost like how can you recreate that with your budget? And sometimes people just go in to increase their debt-to-income ratio just to kind of feel like they doing something.
[00:26:22] Anthony: And ultimately, when you look back at it, is it really worth it?
[00:26:26] Joe: I thought you were talking about buying, like, a couple ferns for your apartment to make it look like you’re in the tropics.
[00:26:32] Anthony: Well, actually, I did buy two extra lamps from the thrift store to make it look like I have a antique
[00:26:37] Joe: Perfect.
[00:26:40] Anthony: But I was like, “I’m not going out and buying them fresh.”
[00:26:42] Anthony: But I was like, “Let me check the value of it on, uh…” As if I were buying it fresh. I was like, “Oh, these are $300 lamps. Let me go and get two of these for $5- … and I’m gonna be okay.” They don’t need to know.
[00:26:52] Joe: Perfect. No, nobody knows what it costs. It’s just what the value is, right? Oh, yeah. And cost versus value, two totally different things.
[00:26:59] Joe: Paula, is comparison always bad?
[00:27:02] Paula: No, I think comparison can be very motivating. If you use comparison as a method of inspiring yourself to achieve greater, greater heights, it… W- whatever that may be, maybe professional success, maybe, maybe fitness, comparison can be very healthy if it’s handled the right way
[00:27:21] Joe: Something else that’s very healthy is, uh, the fact that we take a break halfway through this show for this incredible trivia competition that’s been going on all year.
[00:27:31] Joe: Anthony, it’s your first time playing our trivia. You get to play on behalf of OG, my co-host who’s not here today, and that means some good news and bad news. Anthony, you want the good news or the bad news?
[00:27:43] Anthony: I always go with bad news first.
[00:27:44] Joe: Well, and the bad news, speaking of first, the bad news is you’re gonna have to guess first, and I really don’t like our guest having to guess first.
[00:27:50] Joe: But that’s because you guys are in the lead. In fact, OG is, uh, well, uh, bordering on record-breaking territory. The record for the year is 18 trivia wins, and Doug, what’s the score here with more than half the year to go?
[00:28:04] Doug: Well, with just a little more than half of the year to go, OG/Anthony by proxy has, uh, already reached the halfway mark at nine wins.
[00:28:14] Doug: Jesse not far behind at five. Paula is, might as well be in South Dakota, ’cause she’s got three wins, and, uh, she’s got a long road ahead of her. But,
[00:28:25] Paula: uh- I’ve always wanted to go to South Dakota, actually.
[00:28:27] Joe: And everybody in South Dakota’s like, “It’s beautiful here. I’ll take
[00:28:30] Doug: it.” It kinda is. It actually is pretty there.
[00:28:31] Paula: I’ve heard it’s beautiful. I’ve always wanted to go.
[00:28:34] Joe: Well, super.
[00:28:35] Paula: It’s, it’s, like, high on my list. It’s one of the st- one of the four states I have not yet been to.
[00:28:39] Joe: Well, the good news is, uh, Doug put you there metaphorically already, Paula, so you’re halfway, you’re halfway there. It is funny, when I went to North Dakota for the first time, we stopped in this little shop, and they had stickers, and this is how well the Dakotans know themselves.
[00:28:53] Joe: Think about when you make stickers, you know you’re gonna sell the sticker, right? So you know there’s gonna be market for this. The sticker said, “North Dakota: I saved the best for last.” They know. They know.
[00:29:04] Doug: Yeah. And honestly, they’re probably happy about it. Like, who among us want more people coming to our state?
[00:29:10] Doug: We want more. Like, sure, we like the tourism dollars, but nobody in northern Michigan says, “Come on over. We’re
[00:29:16] Joe: lovely.” Yeah, please. Everybody in the Dakotas right now is like, “Shut up about it.” Right?
[00:29:19] Doug: Right.
[00:29:20] Joe: All right. Uh, we’re not gonna shut up about this week’s trivia, though. Doug, you’ve got the question.
[00:29:25] Doug: Sure do, Joe. Hey there, Stackers. I’m Joe’s mom’s neighbor, Doug, and I know what you’re hungry for, my trivia question. Let’s get right to it. It was on today’s date in 2004 that a woman in Florida, definitely not OG’s hometown, sold a 10-year-old grilled cheese sandwich on eBay because she believed it contained an image of the Virgin Mary.
[00:29:48] Doug: Now, the real question should probably be something like, why in the hell did this lady hold onto a half-eaten grilled cheese sammy for 10 years? But here at Stacking Benjamins, we don’t go for the obvious, do we? No. What we’re interested in is the final selling price of this miracle food. So my question to today’s roundtable is, how much did this holy lunch sell for?
[00:30:13] Joe: All right. At auction, a half-eaten grilled cheese sandwich looked like the Virgin Mary, Anthony
[00:30:20] Anthony: Um, let’s see. Well, I’m going with… Let’s see. This is 10 years ago? Well, she held it for 10 years.
[00:30:26] Joe: She held it for 10 years, and it was in what year, Doug? 2004 you said?
[00:30:30] Doug: 2004.
[00:30:32] Anthony: Did she use Wonder Bread? I mean, ’cause you know it doesn’t mold.
[00:30:35] Anthony: So let’s see. And we know cheese is already mold, so we’re gonna have to go with, I’m thinking of a solid 900 bucks.
[00:30:46] Joe: $900. Well, Jesse, what are you gonna do with that number?
[00:30:50] Jesse: I’m gonna go higher. I’m gonna go higher, but I don’t know how high. How many people climb Mount Everest? 70- What, what was it, 70… Was it 7,300?
[00:31:00] Joe: Wow, taking a dig at Paula.
[00:31:02] Jesse: I think it was 7,300. I’ll go with 7,300.
[00:31:05] Paula: I, I can tell you the height of Mount Everest in both feet and meters.
[00:31:11] Joe: That’s such a weird flex. So how much money, Jesse?
[00:31:16] Jesse: Uh, $7,300
[00:31:20] Joe: for a grilled cheese. 7,300. So we’ve got 900 and 7,300 for a half-eaten grilled cheese sandwich.
[00:31:31] Paula: Man. Okay.
[00:31:33] Joe: 10-year-old half-eaten grilled cheese sandwich.
[00:31:36] Paula: I’m gonna take the middle, but I’m gonna flank the lower side, so I’m gonna go 901.
[00:31:43] Joe: Oh my goodness.
[00:31:48] Anthony: Price is right.
[00:31:48] Joe: That’s the pain you have to go in first, Anthony, right there.
[00:31:51] Anthony: Right.
[00:31:52] Joe: Nice job, Paula. Just run our guest off on- … his first episode. All right. Anthony’s got 900, Jesse 7,300, Paula 901, but what’s your, what’s your real guess? What do you think it really is?
[00:32:05] Paula: I’m thinking maybe two grand or
[00:32:06] Joe: 2,500.
[00:32:09] Joe: $2,000. Is that person on the floor behind you okay?
[00:32:12] Paula: I think so. I think, uh… Oh, I think he’s doing a plank.
[00:32:15] Joe: Oh, is he? Okay.
[00:32:16] Paula: Yeah. All right. Is
[00:32:19] Doug: that what the kids call it these days?
[00:32:22] Joe: We’ll be- We’ll be, we’ll be right back All right, Anthony, you started at 900. It looked pretty good until, uh, Paula went 901. How you feeling now?
[00:32:34] Anthony: Uh, I’m, I’m feeling like I, I should have just went higher just to kind of bump her out, I guess.
[00:32:41] Joe: And Jesse, you got the high end. If it went for a million dollars, I mean, grilled cheese sandwich like the Virgin Mary could have went for a lot.
[00:32:48] Jesse: Well, that’s what I’m thinking. You know, there’s a lot of Christians in the world who maybe they see that Virgin Mary as well in the sandwich, and they think to themselves like, “I, I need that for my mantle.
[00:33:00] Jesse: I need to donate that to my church. That is, uh, we’re gonna build a shrine around it.” You know, you don’t build a shrine around a $900 sandwich. Do you build a shrine around a $7,300 sandwich? Maybe. And so that’s where I’m thinking from the shrine, and I’m working backwards to the cost, and- … I, I like my odds. I like my odds.
[00:33:19] Joe: Uh, Paula, 90- 901. Do you build a shrine around $900- … $901 sandwich?
[00:33:25] Paula: I think you’d build a shrine around maybe like a $2,000 sandwich.
[00:33:30] Joe: Do you then feed it to the person behind you doing planks?
[00:33:35] Paula: I mean, he probably needs some, some carbs, some fats, and some proteins- … all of which would be contained in a grilled cheese sandwich, so.
[00:33:44] Joe: All right, our answers are locked in, 900 for Anthony, 901 for Paula, 7,300 for Jesse. Who’s taking this home, Doug?
[00:33:55] Doug: Hey there, Stackers. I’m aged cheese connoisseur and fraternity brother of the Holy Trinity, Joe’s mom’s neighbor, Doug. Before the break, we asked our esteemed panel of ne’er-do-wells, who does well, they ne’er do well, about the selling price of a miracle. And not just any miracle, we’re talking about a sandwich that had been preserved for a decade without any visible mold, which means either it was divine intervention or it was mostly preservatives.
[00:34:23] Doug: Either way, one of those explanations is significantly more on brand for American cheese. The winning bidder wasn’t a church, an art collector, or a hungry college student, it was goldenpalace.com, an online casino. This is the same casino that also bought a french fry that supposedly resembled Abraham Lincoln for over $75,000.
[00:34:44] Doug: They bought naming rights to a newly discovered monkey species. Uh, they paid advertising revenue for tattoos on people’s foreheads. And here’s my personal favorite, honestly. They bought a kidney stone from William Shatner. I mean, if you wanna build a shrine around something- … it’s Shatner’s kidney stone But anyway, how much did the casino pay for this grilled piece of orange polymer, allegedly?
[00:35:12] Doug: Well, I can tell you that it was $27,100 more than what Anthony guessed, $27,099- Wow. … more than what Paula guessed, and just 20,700 more than what Jesse guessed, because the correct answer is $28,000, making Jesse our winner.
[00:35:33] Paula: Wow.
[00:35:37] Paula: That’s Mount Everest in feet. Mount Everest is actually 29,028 feet.
[00:35:41] Jesse: That’s a great guess right there. That, that’s a winning guess.
[00:35:44] Joe: That’s good. Do you put the shrine on Mount Everest, Paula, to this grilled cheese sandwich?
[00:35:49] Paula: No. No, the shrine is, um… Th- there are a couple of other, like, holier mountains that you can’t climb.
[00:35:55] Paula: Those are where the shrines are.
[00:35:57] Joe: And Anthony, all that, uh, all that Wonder Bread, preserving it for a decade.
[00:36:01] Anthony: Yep. It’s still holding up. I mean, I’m sure. I’m sure it’s somewhere.
[00:36:05] Joe: Kept the, kept the value. The
[00:36:06] Jesse: shrine’s in Uzbekistan.
[00:36:08] Joe: Of course. Of course. Uh, let’s get back to our eight signs that you’re on the right path with money.
[00:36:15] Joe: You might not be finished with your journey, you might be starting out, but these are some great ways to know that you are checking the boxes. So the first four that we had, just f- for people with short-term memory problems, you can handle a $1,000 emergency was number one. Your debt-to-income ratio is under 36%, so you keep the debt low.
[00:36:34] Joe: Number three is you’re not living paycheck to paycheck, and then number four, you stop comparing yourself to others. Let’s kick this half off with sign number five, Jesse. You have good financial habits. You pay bills on time, you automate savings, y- you review your statements regularly. So now that you’ve got that, that foundation, you are now creating a machine it looks like.
[00:36:57] Jesse: Yeah, super smart. Create a system, create a habit, make it automated. Try to remove your fallible human self out of the system as much as you reasonably can. Not to say that it’s mandatory in order to achieve financial success to follow those steps, but, like, it’s so, so helpful. And I think more often than not, when you talk to people who seem to really know what they’re doing or just have a good handle on their finances and have built financial success over time, these systems, these automations, you know, we, we forget stuff all the time, so if you can set up your personal finances in such a way that forgetting stuff doesn’t punish you as much, I think you’ll be better off for it.
[00:37:33] Joe: Let’s walk through some of these systems, because, you know, we don’t have any da- there might be data on this, I don’t know. But let’s take somebody in their 20s, and we now can project 30 years in the future. What single habit, what single system that somebody built, or a habit that they built is a, maybe the best predictor of future wealth?
[00:37:52] Jesse: Me? Um- Yeah … single habit in their 20s that over 30 years is the best predictor of future wealth. I- I’m gonna go with automated investment, uh, contributions
[00:38:05] Joe: Automated investing. Anthony, you’re nodding your head.
[00:38:07] Anthony: Yeah, and I was going through that, thinking about it, growing up in impoverished environment, and really it would’ve been nice to even know about how to invest or even know where to begin.
[00:38:18] Anthony: So it would’ve been great to even know that I could even put away $10, like $5 even, if I could find $5 to think about investing. But it really depends on, you know, the neighborhood that you’re in and also the mindset and the knowledge and the access. And so if you’re coming up and you didn’t know about it or nobody’s around you and your circle is talking about it, it’s just kind of how do you get to that knowledge?
[00:38:41] Anthony: And I’m thinking that by finding people that can actually introduce a podcast such as this and really trying to introduce that little nugget that they can actually start investing. And like, like, “Hey, it’s so simple, just open up the app, set it on, set it and forget it, and go into a nice low-cost ETF and just kind of let it ride.”
[00:39:01] Joe: That is sadly, though, a predictor is access to information
[00:39:06] Anthony: Yeah. Um, I didn’t know all this stuff till I got to college, so, you know, this stuff wasn’t really available. Like, I heard about it in high school, but my teachers never said, like, “Hey, you can actually go in and log into this account and actually get your own.”
[00:39:19] Anthony: They knew about it, but we experienced it, what a trade looks like, but we never were walked through to actually say, like, “Hey, go to this website. Go ahead on and get your parents to sign up as a guardian or a parent for your account so that you can start investing.” That was never taught in class.
[00:39:36] Joe: Who was it in college?
[00:39:37] Joe: Was it a class you took? Was it a, a bookstore you went into? Was it a friend?
[00:39:42] Anthony: It was my old teacher, actually. W- I just happened to go by his office during office hours, and he was just talking about investing and how to create seed money, and then start with the seed money that you create, which is, like, saving a dollar a paycheck or saving $5 a paycheck, and just having that money regardless of where you’re putting it at.
[00:40:00] Anthony: And then take that pool of money once you’re at the end of the month, and then start your investments that way. So that’s what he kind of helped me out with, the seed money process, because I never was even taught about that. And then take that to invest, and that’s when I started learning more and more about finance from that point.
[00:40:15] Joe: I love that analogy because, you know, think of it as seed money. You’re not done, but much like these tips today, you’re on the right path. Paula, we talked about access to information, we talked about automation. What’s another predictor- Mm-hmm … of an early habit that can help you get to future wealth?
[00:40:31] Paula: Related to automated investing, but a, a little bit different, is specifically retirement investing. Since, like, automated investing could be taxable brokerage account, could be any possible container. But specifically automating a portion of your paycheck to go into a 401k, a 403b, any type of a workplace retirement plan, or if you don’t have one, into a Roth IRA.
[00:40:53] Paula: I think that locking that away from yourself into something that you realistically cannot touch, as opposed to a taxable brokerage account, particularly in your 20s, is, uh, very important.
[00:41:05] Joe: Building some friction.
[00:41:06] Paula: Right. Exactly. Building friction, building the guardrail so it does two things. Number one, y- it prohibits you from touching it until you, you know, reach retirement age.
[00:41:16] Paula: I mean, there, technically, there are ways to do it, but if you’re at the point where you’re figuring out those ways, like 72t, you’ve already won the game at that point.
[00:41:24] Joe: Yeah. Yeah The sixth one on this list, you prioritize less stress over looking rich. At first I thought this was about comparison that they were talking about in the piece, but I really like where they take this.
[00:41:36] Joe: It says, “Lower stress, better sleep, and fewer money worries are legitimate financial wins.” And when you realize that, I start thinking, Jesse, that it might be about more than math, right? I mean, is paying off a 3% mortgage a good idea if it helps you sleep at night?
[00:41:53] Jesse: Uh, yes. Is paying off a 3% mortgage a good idea if it helps you sleep at night?
[00:41:57] Jesse: It certainly is from one way of looking at it, and that’s where… I, I just find it so interesting. I feel like I’ve kind of come full circle. Like, my background was engineering, and at one point in life I really did approach all my own finances like an engineer, and just like the hard math. All math. What are the numbers?
[00:42:12] Jesse: What is… Correct. I, I’m a spreadsheet with legs, right? It’s that kind of approach.
[00:42:15] Joe: That’s the way we describe you, by the way. People are like, “Who is Jesse?”
[00:42:18] Jesse: I appreciate that.
[00:42:19] Joe: Spreadsheet with legs. Oh, my God. There’s four
[00:42:21] Jesse: jokes there. How many columns wide am I? ‘Cause I have a feeling you guys talk about me behind my back, and I do not appreciate it.
[00:42:26] Paula: Yeah, I’d say to, to column E.
[00:42:29] Jesse: Yeah. Not bad. I’ll take it. I’ll take it. How many
[00:42:31] Joe: meters tall is Jesse Spreadsheet?
[00:42:34] Jesse: Yeah, how many Himalayas tall am I? But where was I? Uh, oh, both in my own finances, but then also just the, the wonderful conversations I get to have with other people, that’s when you realize, like, there are a lot of people out there who, getting back to the way this article is structured, they’d say, “Well, I’ve got enough good things going in my finances right now that I’m gonna prioritize something that the spreadsheet might not prioritize, but I’m gonna prioritize it because it’s gonna help me sleep better at night.”
[00:43:00] Jesse: You know, like, if I was just starting on day one, and I didn’t have any long term savings, and I, I didn’t have that much put away for investment, uh, like long term investing, would I prioritize my 3% mortgage? Like, maybe, maybe not. I probably wouldn’t. But once I get to the point where maybe I’m coast fire, let’s say, maybe all of a sudden prioritizing that mortgage payment makes a lot more sense.
[00:43:19] Jesse: Mm. I’ve got kids at home that I’m worried about. Prioritizing the mortgage makes a lot more sense. It’s just interesting how these, these feelings ebb and flow, and there certainly comes a time where the spreadsheet might not be the, the dominant, uh, factor in what you decide to do anymore.
[00:43:33] Joe: Do, do you agree with that take, Anthony?
[00:43:34] Joe: That I, I think what Jesse’s kind of saying is that math is better when you start out, but the closer you get to financial freedom the math means less.
[00:43:43] Anthony: Yes. Uh, especially in a relationship. Um, if you let’s go like the partner that you have is a spender, and you really have this goal that you’re trying to pay off the debt, and the other person is like, “Well, we are so close.
[00:43:57] Anthony: We are already there. Like, just let the 3% be there,” that can cause some, some clashing there, and I think that’s where the communication, right, to sit down and actually really get back in alignment with each other. I think that would really help out from the emotional standpoint, and that’s where it becomes beyond the dollars at that point.
[00:44:15] Joe: Paula, this reminds me of a call that we took over on the Afford Anything show where this woman was really worried about her peace of mind and, and, uh, she keeps refreshing her app over and over and over. Do you think peace of mind is underrated in personal finance?
[00:44:30] Paula: I wouldn’t say it’s underrated. I do think that many people discuss peace of mind, but I think that perhaps one aspect of the discussion that is under-acknowledged is that there is a very low correlation between the numbers in your bank account or in your portfolio and your actual peace of mind.
[00:44:51] Paula: I think peace of mind as a concept is discussed, but I think many people erroneously believe that that peace of mind comes about through debt payoff, adequate retirement savings, et cetera, when in fact it might be that objectively your numbers are great, but subjectively you’re still anxious, you’re still worried, you’re still hypervigilant because you have some early childhood trauma or some memories or some deeply embedded lessons that your body still remembers that cause worry that exceeds what the spreadsheet would, would warrant.
[00:45:27] Joe: The seventh sign on our list, and I really like this one, your trend is positive. I feel like we get, we get caught up, Anthony, in reaching the top of the mountain, right? About reaching the, the place. But really the trend and the journey is so important. But that also means that you’re tracking, right? That you’re tracking the trend.
[00:45:45] Joe: What are some of the numbers that you track and that would be important for our stackers to track to make sure that trend’s positive?
[00:45:53] Anthony: Ah, is the trend positive? Well, for me, I would say one of the things that I track mostly is not so much the debt to income ratio, but zero is on a credit card. So as long as it’s zero, I don’t care what the debt to income ratio is.
[00:46:10] Anthony: And that’s one of the things that I track the most, as well as my income. And one of the things that I try to do is try to figure out how can I increase my income, but by maintaining what I have in my day-to-day. And whether it’s to kind of work overtime or if I need to pick up a second job. And so those are the things that I’m tracking right now with this kind of like- So you’re
[00:46:30] Joe: focused on the gap between income and spending, like building as big a gap as possible.
[00:46:34] Joe: Oh,
[00:46:34] Anthony: yes.
[00:46:35] Joe: Yeah.
[00:46:35] Anthony: So that’s my, my goal.
[00:46:37] Joe: Jesse, what do you track?
[00:46:39] Jesse: Uh, let me just try to think here. I guess, uh, the two big things are on a monthly basis, net worth, just, you know, account balances, investment balances, cash balances. And, uh, one interesting thing is I do, I, I make an effort to separate out all the cash balances from the investment account because investment accounts…
[00:46:55] Jesse: ‘Cause sometimes, like you can see, oh, my net worth is going up month over month. If your cash balance is going down month over month- There’s probably a sign that you’re spending more than you’re earning. And so sometimes if you’re just looking at the net worth all by itself, it can kind of cloud what’s going on under the hood on a monthly basis.
[00:47:11] Jesse: And then the other big thing that we track is just what I would kind of subjectively call the big monthly expenses. So like on any given month, I’ll, I’ll sort our spending, right, in our budgeting software. I’ll sort our spending from lowest to highest, and I’ll just look at, like, what were the big things we spent money on, you know, multiple hundreds of dollars and up.
[00:47:29] Jesse: Just so sometimes in review we look backward and we’re like, “Oh, yeah, like, did we wanna spend money on that?” Like, those things kind of add up. So we track those big ticket items, too, just for review and just to see where money is going over time.
[00:47:41] Joe: Yeah. Cheryl and I talk about the big items in our weekly meeting, what are those big things.
[00:47:45] Joe: So I love the idea of tracking your net worth and, uh, looking at that ladder. I also love tracking your income. Paula, anything else you track besides those two?
[00:47:55] Paula: I’d say for… I mean, on a month-to-month basis, predominantly I’m look- I’m just looking at cash balances. Particularly, I have to move money around sometimes between accounts.
[00:48:04] Paula: So a lot of it, on a month-to-month basis, a lot of it is just cashflow management. But then twice a year I zoom out and bigger picture look at net worth. But I only do that as a manual process. I will literally log into every single account and transcribe those numbers onto a spreadsheet. And I know there’s net worth tracking.
[00:48:23] Paula: There’s lots of net worth tracking software, but I, I think that there is a moving meditation to, like, manually doing it. But because it’s so labor intensive, I on- I do that twice a year.
[00:48:33] Joe: You know, it’s funny, I listed a few just as I was prepping for this. Net worth tracking, cashflow. So we got Jesse’s, Anthony’s, uh, well, that really adds Paula’s, too, uh, debt reduction.
[00:48:47] Joe: The one that I wrote down that nobody mentioned was savings rate. Do any of you really track savings rate changes and try to be more saving this month than, than next month?
[00:48:56] Paula: I don’t because my income fluctuates so much
[00:48:59] Joe: Gotcha
[00:48:59] Paula: If anything, I’m tracking my income rate, not my savings rate
[00:49:02] Joe: Okay. Anthony?
[00:49:04] Anthony: Yeah, the same. Um, I just make sure, like, how much I can contribute, not so much the percentage Gotcha.
[00:49:10] Joe: Jesse, do you watch your savings rate? Uh, annually. What I try to do,
[00:49:14] Jesse: mainly for my wife’s benefit too, ’cause she’s not in the weeds as much as I am, so I put together this, like, brief quarterly report and then a slightly longer annual report for her just so she feels like, “Okay, I’ve got a pulse of e- all the different moving pieces.” And especially in the annual report I’ll pull out all the savings data so that we can both understand our kind of annual savings rate.
[00:49:34] Doug: Do you guys do this over, like, a Zoom call? Or do, like, is this, uh, with investors? My
[00:49:39] Jesse: people call her people. Uh,
[00:49:41] Doug: Zoom call. Okay. All right.
[00:49:42] Jesse: Agenda.
[00:49:43] Doug: All right.
[00:49:43] Jesse: Very official.
[00:49:44] Doug: Sounds romantic.
[00:49:45] Joe: The last one on this might be my favorite. I’m watching this show on Netflix, uh, this reality TV show. Ryan Serhant. It’s Owning Manhattan.
[00:49:55] Joe: You look at all these people with these… And Paula, you get a first-hand look at this every day. $9 million for this apartment, and that’s not even one of the nice ones, right? The super nice ones, 50, f- 40, $50 million to get into these places. You start looking at that, and it makes you think of this, this eighth sign.
[00:50:17] Joe: And the eighth sign is money’s a tool, not your identity. But I c- I get this strong feeling from this show how much this piece of property is their identity. And it isn’t, by the way, how beautiful the property is, it’s the fact that it costs $50 million. It’s their identity. It’s this, it’s this weird flex.
[00:50:36] Joe: I don’t know. Is this maybe, Paula, the hardest lesson in personal finance, that money is a tool and not your identity?
[00:50:43] Paula: Well, I think when you’re talking about that level of wealth, in order to obtain that level of wealth, there has to be a certain degree of obsession for most people. You know? There has to be a certain, like, all-in on typically th- the business or businesses that you are building to such an extent that all else goes to the wayside.
[00:51:06] Paula: And in fact, you may or may not even be doing that for the money per se. It might be that you’re just really interested in… You’re, you’re very, very invested in the, in growth and in seeing how far you can take this. I think that is actually more often the case because if it’s simply a means to an end, then, um-
[00:51:24] Joe: I think that definitely is the case.
[00:51:26] Joe: I think their job in a lot of ways is their identity, and when I see the people in these apartments, though, I think the apartment is like a status symbol, though. It is 100% a status symbol.
[00:51:36] Paula: Yeah. Well, I think Paulette and I were talking about this the other day. One of the things that you encounter in- The writer
[00:51:40] Joe: Paulette Perhach for people who don’t know which Paulette we’re talking
[00:51:43] Paula: about.
[00:51:43] Paula: Yeah, yeah. She was the replacement for me on the Stacking Benjamins podcast a couple years ago. I took a one-year hiatus, and so Paulette was the new Paula- … over the span of that year. But we were talking the other day about the fact that in New York, throwing a dinner party is a huge status symbol because you are implicitly saying-
[00:52:02] Joe: I got room
[00:52:03] Paula: I have enough space to have a dining table. You know? And that is such a flex. To have a dining table, any dining table, um, even if it’s a fold-out card table. Like, the fact that you’ve got enough space for that, that is a huge flex.
[00:52:19] Joe: It’s interesting, Anthony, ’cause you and I apparently, based on what you said earlier, we both grew up in the opposite side of that.
[00:52:25] Joe: I grew up in a fairly poor part of West Michigan, and I just thought- Wealth wasn’t for me. Like, it, it just, they were talking to other people. I didn’t know anything about any of this stuff. How do you teach that money is a tool and not your identity? For some people on one side, like you and I, that it is a tool and we should be using it, but on the other side, it doesn’t have to control everything.
[00:52:47] Anthony: Yeah, I had a client recently reach out to me, and they were just trying to figure out, like, they had credit card debt, but they were trying to take care of their kids at the same time, but they also had investments. And I was like, “Well, you already invested in your 401. There’s extra money that you’re just throwing around to invest, and you have some dollars that’s flexible there.”
[00:53:06] Anthony: I just throw it there as a, as a possibility. I didn’t give them advice ’cause I’m not an, their advisor. But I was just saying it’s like, if the money is there as a tool to kinda help you and your family to be comfortable, then just sell the stocks because you got what you need far as on the back end. You have your retirement set up.
[00:53:24] Anthony: You have… But your kids need food on the table, and I would rather for you to have food on the table, and you can build that up later. But again, it, each level, money as a tool will look differently. And for this moment, this is, money is there. It’s a tool. You put it as, not to look at your investment as a savings, but this is one of those options to look into and just kinda say like, “Hey, you haven’t invested.
[00:53:48] Anthony: You have the free money. You don’t have the time, and things came up as an emergency. You need this money to, to survive.” And I would- For the peace of mind, going back to using it as a tool and the mindset of this is more than the money at this point, it’s about survival and peace of mind, she went on and did it, and she said, she said, “Thank you for the option.
[00:54:10] Anthony: I hadn’t even thought about it that way.” And she was able to be able to have, like, you know, put food on the table. Wow. Still continue to invest and build that back up. So…
[00:54:19] Joe: Yeah. Yeah, pretty powerful moment.
[00:54:20] Anthony: Mm-hmm.
[00:54:21] Joe: Jesse, why do so many people tie self-worth to their income and their net worth statement?
[00:54:27] Jesse: Um, one reason why has to be that money is easy to measure.
[00:54:32] Jesse: It’s so easy to measure. You can count it. How am I supposed to count my self-worth, Joe? I, I, just think, you know, I think it’s much harder to, right, it’s obviously it’s a much harder question. It’s like- It is an easy
[00:54:41] Joe: scorecard, though. It’s an easy scorecard.
[00:54:44] Jesse: Money is. Yeah, it is. It is. I also think there’s probably a uniquely American part of this question, too.
[00:54:49] Jesse: I mean, I am swimming in American waters. I am sitting inside the American frame. I can’t speak as an outsider. But when I hear outsiders speak of American culture and American, you know, the stock market, our corporate culture and capitalism and all that, it sounds like we’re probably more money obsessed than a lot of the rest of the world, too.
[00:55:08] Jesse: So I think some of it might have to be… Some of it probably is uniquely American, where it’s like, well, yeah, we compare each other in a personal finance sense more than other people in the rest of the world compare one another in a personal finance sense. There’s some of that, too. I probably need to go, you know, cuddle up with some philosophy books to really start answering-
[00:55:26] Jesse: your question, Joe. But I think some of it’s probably just in that, of, uh, what other measuring sticks are there? There’s my height. There’s how far I can throw a baseball. And then there’s the, uh, that number at the very bottom of my net worth statement.
[00:55:38] Joe: We got eight of these today. It strikes me that three of these on the list are stability, that foundation.
[00:55:44] Joe: Three of them are behavior. Two of them are mindset. Of the eight, which one of these really speaks to you the most? We’ll start ladies first. Paula?
[00:55:54] Paula: You know, going back to the one about living paycheck to paycheck.
[00:55:57] Joe: Yeah.
[00:55:58] Paula: The reason that I like that one is because it’s a lesson that applies at all income levels.
[00:56:03] Paula: If you’re at a very low income level, at a certain point you can’t shrink down any further, so you’ve got to income up, right?
[00:56:11] Joe: Yeah.
[00:56:11] Paula: But if you’re at a higher income level, then it’s more a matter of adjusting your spending and adjusting your, the way that you’re managing your money. So that lesson applies no matter where you fall on the income spectrum.
[00:56:22] Joe: Yeah, Anthony, which one speaks to you the most?
[00:56:25] Anthony: Uh, for me it’s definitely the money behaviors. Mostly because growing up we didn’t have much, so that has been my focus, uh, is really trying to make sure that everybody understands their, their triggers, their habits, and their needs to kind of make sure that whatever they’re doing is actually aligned with all of that so they don’t go beyond that.
[00:56:46] Anthony: Or if there’s a way to kind of replace that need and trigger, so.
[00:56:50] Joe: Yeah. Uh, Jesse?
[00:56:52] Jesse: My initial answer was exactly what Anthony just said. It was the money behaviors one. But to mix it up, I will go with, um, prioritizing time and stress reduction over optics. Yeah. ‘Cause again, I think there, there are different races you can run, and the r- the race that says, “I want every single number to be as optimal as possible so I can get to the finish line the fastest,” also comes with other types of stress.
[00:57:15] Jesse: And so I think when people find a way to balance and say, “I actually wanna reduce my stress and buy back some of my time, even if it means my numbers aren’t perfect,” I, I bet those people actually have better long-term outcomes.
[00:57:26] Joe: That’s the one that speaks to me the most too. Many of you know that I’ve been working on this retirement project, and putting together a happier retirement.
[00:57:34] Joe: But then just, Jesse, this idea of just solving for happiness is something that gets lost in the weeds. We solve for more money, we solve for more longevity, we solve for so many different things, and we forget solving for happiness is a big part of the equation. Great discussion. I hope this helped a lot of our Stackers.
[00:57:52] Joe: You know, stop comparing yourself to other people. But also, you know, it’s funny, just also stop and measure how good it is what you’ve done. I think often we’re so busy looking at the horizon, and the horizon continues to move the more we move. And we just think, “Oh, I gotta hit that next thing. I gotta hit that next thing.”
[00:58:10] Joe: So if you’re able to sit and stop and look back and go, “You know what? I’ve started to build a pretty kickass foundation. Sure, there’s some things I’m not doing as well as I could, but I’m on the road, and I’m working on it every day,” which is pretty, pretty awesome. All right. Let’s find out, speaking of awesome, what’s going on where all you guys work.
[00:58:28] Joe: We will have our guest of honor, Anthony, go last. So let’s start off with Mr. Jesse Cramer over at the Personal Finance for Long-Term Investors podcast. Uh, what acronym did we settle on last week? Did we change it up, Doug?
[00:58:40] Doug: We did. His podcast is now FILTI.
[00:58:42] Joe: Yes. What’s going on at the FILTI podcast?
[00:58:48] Jesse: Um, I know it depends on what day today is. I still think we’ve had some recent episodes on the 14, uh, risks that you face in retirement using the Charlie Munger principle of inversion. But if we’re past that one, then we’ve got an AMA coming up. You know, just kind of a classic AMA episode, four or five questions about retirement planning that I kind of dig into some of the details and help my listeners out.
[00:59:09] Joe: You know, it’s funny, you’d have an AMA. Anthony would have an AAA, Ask Anthony Anything. It’d just be AAA. Yeah.
[00:59:16] Jesse: Triple A. Yeah, Triple A. That’s true.
[00:59:18] Joe: Paula, over there on the Afford Anything podcast, what’s cooking?
[00:59:22] Paula: On the Afford Anything podcast, we aired, uh, recently an interview with Dr. John Lapuma. He talks about the importance of going outside, touch grass.
[00:59:31] Paula: He talks about how your office is killing you. Too much time spent indoors is bad for your health, and it’s actually bad for your productivity, and he lays out the scientific and medical reasons, uh, why that’s the case and why you need some outdoor time. He
[00:59:44] Joe: doesn’t specifically talk about basements, does he?
[00:59:47] Paula: Uh, no, no, not specifically
[00:59:49] Joe: basements. Oh, thank God. Oh, good.
[00:59:50] Paula: But given that basements are indoors, I think basement is included under- Oh, crap … the indoor category.
[00:59:55] Joe: Oh, no. I thought we had the little asterisk ’cause basement really the house? I don’t know.
[01:00:01] Paula: So yeah, that’s on the Afford Anything podcast.
[01:00:03] Joe: We’re a finer podcast, like the filthy podcast.
[01:00:05] Joe: Our, our phone.
[01:00:07] Paula: Exactly.
[01:00:08] Joe: Anthony, uh, thank you so much. We finally got this done, man.
[01:00:11] Anthony: Yeah.
[01:00:12] Joe: It’s about time we finally got this done. Like
[01:00:13] Anthony: three years late.
[01:00:15] Joe: I know. Totally. Like for the last three FinConcs in a row. Yeah. “Hey, we gotta do that,” and then we don’t. And then I see you at PodFest, and then we don’t.
[01:00:23] Joe: And then, yeah, but we finally did. So what’s going on at About That Wallet? What’s coming up?
[01:00:27] Anthony: Uh, what’s coming up? I got my mom episode coming up. She’s- Oh … finally being on the show. She’s always been in the comments, um, and always giving me side comments like, “Hey, where did you know this person? Where you meet this person?”
[01:00:37] Anthony: I was like, “Well, you finally get to be on the show.” Uh, so we actually talking about her childhood, growing up, having kids and being a underage… Well, I wouldn’t say underage. You know, being a 17-year-old mom, a teen mom, and then just kind of how she’s getting ready for retirement, so it’s pretty cool.
[01:00:53] Joe: I was looking at the, uh, some statistics at Miller County, Arkansas, which is 800 yards from here, and the statistics of if somebody’s a teenage mom, how difficult life is gonna be and how much struggle you’re gonna have, and the struggle is, is, is real.
[01:01:09] Joe: Those numbers are pretty ugly, as you, you know first- your mom knows firsthand.
[01:01:13] Anthony: Yeah. Yeah. Caught the bus everywhere, so that’s what we had to do.
[01:01:17] Joe: Well, that’s good. I love those personal stories, and I can’t wait to hear mom’s story on, on the show. Thank you everybody for hanging out with us. We do these live on YouTube.
[01:01:25] Joe: The YouTube audience has been awesome. Great seeing all of you. Uh, we are here Monday afternoons reliably, so if you’d like to join us, it’s always fun pretending it’s Friday on a Monday in mom’s basement. We always end the show, though, with Doug telling us, man, what are the top three takeaways from today’s show?
[01:01:43] Doug: Well, Joe, first, take some advice from Anthony Weaver. If you’re the leading expert in Uzbeki architecture and you lose your job, make sure your emergency fund bucket is separate from your day-to-day spending bucket and that it’s earning the highest possible interest rate. Second, don’t forget when Paula said the thing about automating a portion of your paycheck to go into a retirement-specific fund.
[01:02:05] Doug: That’ll prohibit you from touching it better than mom whacking your hand with a wooden spoon. But the big lesson, when you’re looking for some decorative rocks for your turtle’s aquarium, maybe don’t grab the extra ones in Joe’s mom’s kitchen. How was I supposed to know those were your favorite kidney stones, Ma?
[01:02:24] Doug: God, put them somewhere else.
[01:02:26] Joe: Oh, man. Who needs William Shatner’s kidney stones when you can get Mom’s?
[01:02:30] Doug: Ma’s got a pile of them up on the counter.
[01:02:33] Joe: Nope. Oh, man.
[01:02:35] Doug: Thanks to Anthony Weaver for joining us today. Be sure to check out his podcast called About That Wallet on just about every platform known to modern man.
[01:02:45] Doug: Still can’t find it? You got bigger problems, but don’t worry. We’ll help by including 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 finer podcasts. And finally, thanks to Jesse Cramer for joining us today.
[01:03:04] Doug: Wanna get filthy rich? You’ll find his podcast, Personal Finance for Long-Term Investors, It’s Filthy, wherever you listen to your finest podcasts. We’ll also include links in our show notes at stackingbenjamins.com. This show is the property of SB Podcast, LLC, copyright 2026 and is created by Joe Saul-Sehy.
[01:03:27] Doug: 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. 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.
[01:03:46] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s mom’s neighbor, Doug, and we’ll see you next time back here at The Stacking Benjamins Show


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