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This episode is brought to you by Lifelock.
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It's Cybersecurity awareness month and Lifelock has.
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Stay smart, safe and protected with a 30 day free trial@lifelock.com podcast terms apply. Hey kids, how many people you think are dead in that cemetery?
C
Not again.
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All of them.
D
Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor, Doug. And gather round, stackers, while we share ghoulish tales of financial horror. What goes bump in the night in your wallet portfolio or worse, your credit? We've packed a silver bullet for each of them. And of course, nothing could be darker than a dose of incredible Halloween themed trivia. And now, a guy who was nearly buried alive in debt. It's Joe Saul Sehi.
A
That was a horror story, Doug. I was super happy that I lived through to be here with all of you today. Happy Halloween, everyone. Welcome back to the Stacky Benjamin Show. I am Joe Saul Sehi. And do we have a treat for you. This is going to be like the virtual campfire where we sit around and we tell just ghoulish money stories and maybe we'll even get one from Doug. You think? Doug, do you got a. Do you got a ghoulish story?
D
I've just got to figure out which one to pick. Joe, that's going to be my challenge.
A
And they're all about me, I'm sure. Actually, it's not going to be all about me today. We've got a fantastic panel. Let's introduce you to them. First of all, the guy we collaborate with consistently each and every week. Just back from Bali so we could make this recording doc g from earning investors here. How are you, Jordan?
E
Oh, I'm doing well. Joe and I first wanted to compliment You. That is mighty scary Halloween outfit you have on.
A
Thank you. Are you talking about my face? You're talking about my face. Thank you. It starts already. We've gone three minutes.
D
Let's.
E
We don't pull any punches here on the Stacking Benjamin show.
A
Let's see if we can do better. If we go north of you. Well, not north east of you in Rochester, New York, where our friend from the Better Interest blog. Better Interest. It's like the old days.
B
That's spooky.
A
The Better Interest, that's a callback. The Best Interest blog and long term investing for long term something personal finance.
B
In the spirit of Halloween, you are butchering this intro.
D
Wow, this is like a slasher movie.
A
Wherever he's from, Jesse Kramer's here. How are you, man?
B
I am doing great. I'm excited to be back. It's been a couple of weeks since I've been here on a recording. Really excited for this one. And you know, in the spirit of Stacking Benjamin's, I got to meet a Stacking Benjamin celebrity yesterday in person.
A
Wait, what?
B
I got to meet. Do we tell them?
D
We tell him neighbor.
B
Doug and I got to meet in person yesterday.
A
No way.
B
Essentially at a interstate rest stop, which is where all good meetings take place.
A
Yeah, that's where Doug meets everybody in the restroom.
B
It was outside of a Panera Bread, so the bread wasn't the only thing that was stale. But it was worthwhile.
D
It was worthwhile.
B
Doug went out of his way.
D
Positively swooning.
A
So good. Well, you know what? I'm suiting Jesse. You know why?
B
Why is that?
A
Because we have a very special guest with us today. Oh, we're super happy she's here. She is a star of Tick Tock and Instagram. She also is one of the people I was geeked to meet at fincon this year. Emily Agashira from Hey friend, it's M. AKA M is here. How are you?
C
Hello. Thank you so much for having me. I am so excited to jump into this fire chat and talk about all these scary money stories because have my own to contribute to this because we all start somewhere with money. So I can't wait to see what everyone else thinks about the crazy thing that I did many years ago.
A
Which is by the way, funny, Em, because and you've said this before on your TikTok channel, which I love, and we'll have links to your TikTok channel and Instagram and everybody's work on our show notes page is Stacky Benjamin's. But people think that for you to get as far as you have with your money, like you've just done everything perfect. M. Everything's perfect for Em and her family all the time.
C
Yeah, well, we sometimes have to make those really big mistakes that rock us and bring us to a rock bottom. And you're like, wow, something's got to change. And well, when you throw some zeros on the end of it, that'll get you motivated, that'll get you changing.
A
And I said, as far as you've come, our stackers might not know how far you've come. So tell everybody about your channel and about your story.
C
My name, I go by M and I am a personal finance content creator. I'm also a certified money coach and I talk about my journey from poverty to becoming a self made millionaire in my 30s, completely debt free, including our home. It's a pretty incredible journey that my husband and I took to get here. And there was no like overnight bitcoin lotto. There was no trust fund. It was just good old common sense, wealth building tips and strategies. So.
A
Oh, that's crazy talk. That is crazy talk.
C
Yeah. So I share my frugal life and I share how rich it is and how I can help other people, you know, learn about money and inspire them to hopefully be de influenced in a world that is like so influencing when it comes to like over consumption. So.
A
Well, maybe he'll be a good influence on Doug because he needs all the help that he can get. So. I can't wait to hear everyone.
C
I'm clicking on Doug today. I see. All right.
A
Oh, no. This is just another episode.
D
We have a role to play in this world.
A
You notice how Doc G started it off by talking about my Halloween costume and it was downhill from there. We're going to be telling our best or maybe our worst. Doug. I think it's our worst. Isn't it our scariest money Halloween stories.
D
If it's going to be a good episode, they better be the worst.
A
We gotta, gotta, gotta bring it. I can't wait. We've got M here, we got Jesse here, we got Doc G here. We're gonna hear their stories in just a moment. But first we have a couple sponsors who make sure that we can keep on keeping on. You don't pay any money for any of this goodness today. So we're going to hear from them and then it's time to gather around the campfire. Kids, we are the musers on the pod. So far we've discussed people we love. I didn't tell you Guys, Cuban emailed. What are you wearing? Well, no, that's not. Things we love. Got way into typewriters. How many typewriters do you own?
D
Let's not podcast anymore.
A
Guesstimate.
B
It's time to get really down and dirty. These are great ideas.
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Start a podcast and then forget to promote it on social media. So what is our podcast about? Whatever we feel like. The musers the podcast. Follow and listen on your favorite platform. Everyone knows the legend of D.B. cooper, but what if I told you there's an even better story out there? One with multiple aircraft hijackings, prison escapes.
E
And so many twists and turns.
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I'm talking about the hit podcast American Skyjacker, which is now an action packed documentary coming to theaters and streaming this fall. Find out more at www.americanskyjacker.com and listen.
E
To our bonus episode of the podcast.
A
Coming soon, American Skyjacker. Follow and listen on your favorite platform. All right, Doc G, do you mind going first, stepping up to the fire and making the spooky face and tell us the scariest money story in the Earn Invest repertoire?
E
I actually have a really scary story and it's no joke because the consequences were actually profound. So most of you guys know that I am a physician and I'm a hospice physician, so I take care of people at the end of life. I had this guy Dan come in town because we were having a family meeting because his mom had really end stage bad Alzheimer's. And this guy Dan was really, really thankful because his dad had done everything right. Like he had organized the care and he had all the medical powers of attorney and the financial power of attorney, and everything was settled. And so when we had our family meeting, I met Dan, his mom, his dad, his dad was totally with it. His mom was getting to end stage dementia, and Dan was just so happy. And I felt good as the doctor because I'm like, you can go back to California. We're in Illinois. He lived in California. I'm like, you can be rest assured when things go bad, we have everything in place. Well, this was right around Covid, and he goes back to California, and two weeks later, not his mother, but his dad gets Covid and gets put on a ventilator. And Dan comes to town and guess what the problem is. Well, his dad had the financial power of attorney. Dan didn't have any financial power of attorney. But now his dad was on a ventilator and couldn't speak for himself. And Dan had to not only figure out what to do for his dad, but who was going to pay all the bills for his mom who had around the clock care at home. Their finances were completely frozen.
A
Oh no.
E
It was really scary. And here's the really sad thing that happened. It resolved. But the only reason it resolved because dad Stan died of COVID And then all of the contingent will and everything kicked in. And then he was able to take over the finances and pay the caregivers for his mom, et cetera. But it was really, really sad. But if his dad had remained alive but on the ventilator and incapacitated, he would have had to go to the court systems and try to take over their financial control. And that can cost lots of money and a lot of time. And poor mom had very expensive care at home that they had to make sure that they could keep supporting. But not only that, he would had to do that while his dad was critically ill in the icu. It was just a really sad story. And it reminds us how important that financial power of attorney is if something goes wrong and your family member lives. They haven't died yet, but they're incapacitated. You need to be able to make financial decisions for them.
A
A story goes from horrible to worse when the best thing that could happen was he died.
E
Yeah, it was really sad. I mean, the whole thing was sad. But I hate to say it, as the physician, I had a moment of relief for him that at least he could get his mom the financial care she needed and that we weren't facing down him going to court and trying to wrestle control of their finances.
A
Yeah, this is always so hard, Em. I mean, I just think, especially when people are younger, they think, well, death is something that happens later on. Right. But for our stackers that are in their, let's say their 30s, I mean, now's the time to get all this stuff done.
C
Yeah, no, absolutely. And like, it's funny that that was brought up because just the other day I was talking about like term life insurance and we always. It's always something that's like, it's on the list, but it's so low on the list and like, I'll get to it one day. But one day is never. We all know that. And sure enough, like, I actually, my husband has a policy and I was like, you know what? I think I'm get a policy. So I started walking like people through the process of me actually applying for. And something else that I'm going to be doing too is like, we're talking about, like you said, estate planning and like getting those directives and things in place. That is something that. I really feel like we need to teach that in school, because that's something that we need to get set up, and we need to get it set up as young adults. And I think people just think that, like, oh, I have time. I'm healthy. I. Oh, maybe I. Not until I have more money. But to Dr. Yi's point, we don't know what's going to happen, and we don't want to put ourselves in a place like that where now you're scrambling and you have to go deal with courts, or. I mean, it just makes the situation 100 times worse than it already is. And so it is so, so important. And I think one last thing I'll say, too, is that it's not complicated. There is, actually. We are spoiled now with the Internet and that there's so many different websites and tools that you can use to set up these wills, these trusts, and these different documents. Documents within, like, minutes online.
A
Yeah.
C
And they're very affordable. Like, you don't have to go old school and go work with, like, an attorney. This is something that you can do on your lunch break and be like, hey, honey, I thought, I'm. I'm just gonna go ahead and start working on our will. Or, I don't know.
B
You know what I mean?
C
It doesn't have to be, like, as scary as it sounds.
A
But it's funny. When my kids were 2 years old, I think you have a young child at home. I remember just feeling so vulnerable. I'm a financial planner. My kids are 2, and I don't have a will. I don't have that done. I remember it still took until they were, like, four for us to get all that stuff done. And it shocked me how much better I felt. I was blown away by how all of a sudden we walked out of. We did work with an attorney, and I walked out of his office, and I felt so good. I was like, I never thought I'd feel this good. I thought I'd feel morbidly bad because I was acknowledging death, you know? But instead, I felt great.
C
Yeah. I think for some of us, we don't want to think about it because it makes it more real. It makes us feel like we're not invincible and we don't want to face it. And, like, I'm not going to lie, I even feel that way thinking about this planning, and you have to ask yourself really hard questions about what would happen if. And it's overwhelming sometimes, but it's absolutely critical.
A
Mine's super hard. I always think about, how do I make sure I just exclude Doug from everything? Like, how do we? How do we. You have to write it in. I don't know if you know this, but if you want to specifically exclude somebody, you have to write. Doug gets nothing. So that's letter for letter in my will.
C
It's like, he works pretty hard. He might be entitled to his fair share.
A
Oh, but don't start him, please, God, no. No. Jesse, you also have a young one at home. This is a big area for you, too.
B
It is. We're a little bit tardy. I might have even shared it here on the podcast before. We're tardy because we're the guardians. Conversation for us has just taken longer than we are.
A
It's so hard.
D
Terms of I'm right.
B
Yeah, like, exactly. Doug. Doug had a tryout yesterday, and the baby was not impressed. The baby was not impressed. If you haven't seen the picture on the stacking Benjamin's Facebook group, you need to go check it out because she's one of the happiest babies I've ever encountered. Unless she's within, like, six inches of Doug. Apparently.
D
She tried running away from me at least 11 times. Just kept sprinting the parking lot, through.
B
The parking lot, through traffic, toward the stale bread of Panera instead of being close to Doug.
D
That's how bad she wanted away from me.
B
But no, it's funny. In the spirit of Halloween, right? Brains. Is it the zombies brains? Our brains. Exactly. Like Em was saying, the thought of death, that concept of death, planning around death, having to face our own mortality is not something that we necessarily want to dive into headfirst. And also, it's this kind of thing. It's very real. There's this very binary series of things that can happen in your life where either you're totally healthy, in which case, why do you even need an estate plan, or you are so incapacitated that you wish you had your powers of attorney, like Doc G pointed out, or you're dead, in which case you wish you had your estate plan. And none of us want to think about the way that the light switch can flip in those directions. So the easier thing is just to let inertia continue on and not get it in order. But so many of the horror stories that I've encountered firsthand through client work are related to someone at some point in time not getting their estate planning docs in.
A
Over and over. You see it over and over. Yeah.
B
Correct.
A
I used to, when I was giving speeches a lot. When I was with American Express, I would always. I would always just point out that if you don't have a will, the state has a will for you. You do have a will. And then I would point. Do you really want the state you live in to be in charge of your estate plan?
B
It's.
A
It's absolutely horrible. The guardian thing was tough for me as well. Doc, how old were you when you got your estate plan done?
E
We did it when the kids were young, so it must have been, what, 10, 15 years ago. And then we just revisited it again about a year ago just to make.
A
Sure Doug is named.
E
Just to make sure that Doug is named as. Not a recipient. But, you know, my kids. So my. My son is turning 21. My daughter's turning 18. So, you know, it's not a bad time to revisit it because they're older. So guardianship is no longer an issue. But you have to start kind of thinking about how things change as. As their life cycles change as well as your own.
A
Yeah. It's a big thing. And I just can't believe how that horror story could all be taken away.
E
Yeah. And you. You don't want to deal with conservatorship. You want to avoid conservatorship at all costs. You do not want to have to deal with financial conservatorship.
B
Yeah.
A
I just can't believe the guy's name was Dan. Dan. Trying to petition the court to help out his mom to get the finances moving. Like, that is just a. That's a horror story on its own. So nice job, Doc. Starting off with death at our Halloween. Good work. Understand the assignment.
C
M. Yeah. Okay. Are you guys ready for this one?
A
No.
C
This is not a moment I'm proud of. But you know what? This was a learning moment, and I'm curious to hear what everyone thinks. So before my finance journey, I was. I was 24, and I was dating someone who was really into cars. I was like, oh, yeah, I want to go get a new car, too. I had a totally fine car. My current car, I had bought new. I almost paid it off, but we walk up and we pull into an Audi. I'm 24. We pull into an Audi, and I'm like, I want this show floor model. Better yet, I was like, I want to lease it.
B
I don't want to buy.
C
I want to lease it. I remember sitting down with the representative. I was making 60,000 a year at the time. Pretty good for 24. And the car was $60,000. I was going to lease a car worth my salary. I actually Emily, now I wish I could have told her I had like $12,000 of equity of value in this other car I had. And I was like, let's just roll it over. And then I also made like $2,000 towards the lease agreement to lower the payment. So my lowered payment was $550. And this was almost 10 years ago.
A
Just on the lease, which is the depreciation and interest on the car.
C
I end up paying about $35,000 over the course of that three year lease to just rent a vehicle. Yeah, that was a really tough driving that.
A
I was about to ask you that. Did you feel like a badass the whole three years you were broke driving that car around?
C
I mean, it was a nice car, but my budget was saying otherwise, you.
B
Know, I mean, it was my budget a little extra.
C
I had the mentality of if I can afford the payments, I can afford the car. And that is such a common theme that we. I see and hear a lot nowadays with people. But the reality is you don't take into account everything else. You don't take into account all the maintenance in the insurance. And I had to change out my tires on this car. I had to pay for OEM parts, so I couldn't get aftermarket. I couldn't get. I had to get Audi name brand parts.
A
And those are inexpensive. Those are really inexpensive.
C
My tires alone to replace them were twelve hundred dollars for tires, which, I mean, this again, ten years ago. It's like inflation just. I mean, we're talking crazy money. And I'm 24. So that is my really scary horror story. Thankfully, after that I got on my personal finance journey.
A
That is a. That's a frightening one, Jesse. Why is it, why is it that we. We all think in terms of payments like we do? Oh, I'm going to do this third subscription. I only have one set of eyes. I'm do a third subscription because it's only 12 doll or whatever it is.
B
Yeah, I mean, it's so much easier to stomach. I mean that, I mean, m. That car, right? That wasn't a $60,000 car. That was a $550 car. Like, what are we talking about? Yeah, I'm just saying facetious, of course.
C
But like, right.
B
I think so many of us, it is so easy. It's so alluring just to think a little bit shorter term. Right. Like, why do we have to think about 5 years and 10 years and 20 years down the line? Like, that's too hard. Why not Just think about the next three months, in which case your payments M was what, three times 550 and like, it's pretty easy to stomach. Or it's very easy to say like, okay, you were making $60,000 a year, you were making $5,000 a month gross, 550, what is that, 11%? 11% seems like a smallish number. 11% of your gross pay went towards that car. That's not that bad. We have these totally understandable, very human ways of rationalizing these financial decisions, of minimizing certain numbers. Especially when, I mean, have you seen the way a new Audi looks? It's totally understandable. But yeah, it's cool that you've reached this point. So many of us, we learn from these mistakes and 10 years later we're like, oh, damn it.
C
Yeah. And I think especially with these younger generations, we FOMO and not FO and like, sorry, YOLO too. FOMO and yolo, we like our abbreviations all together and we're living in the moment and it's, it's going to be impossible to retire anyway, so I might as well enjoy life. I might as well buy the car. I might as well do this and that. And we don't think about opportunity cost. And if Emily now knew what I knew back then and I invested $550 every month, I mean, we're talking serious money.
A
And so, you know what's funny is you could have then later on, easily, easily bought an Audi later, you know what I mean? Later on had all the Audis you want because your net worth is fine.
C
We don't know what we don't know. Right. And that's why I made my channels too, is being able to enjoy your money now while also still, to Jesse's point, breaking out of that short term view and start to see past that and like, okay, how can I balance my budget to enjoy both?
A
I had a mentor once who said, you got to look past the short term and obvious to the long term and not so obvious. And I think for a lot of people leasing over the short term, Jordan seems like the best thing to do. But long term, not so obvious. It can get kind of ugly.
E
You have to put your hand on the stove once to know to avoid the stove later on in life. You want to make these kind of bad decisions when you're young and they're recoverable. And so thank God this was a very recoverable mistake and the opportunity cost you missed was worth the lesson you learned. Yeah, it's hard, right, because we grew up. We work really hard, we get our first adult job. And you know, I went to medical school, right? So a lot of times you get out of residency and you're like, I've worked so hard, it's time to enjoy the fruits of my labor. And so many doctors do this too. So many doctors.
C
I deserve it. Disease.
A
Yeah.
E
And so we. And so you're like, I work so hard, other people have this stuff and so I should have it too. But we also know that there's such thing as hedonic adaption. I mean, cars generally don't also make you happy in the long term. So if you can, you can start thinking about happiness, you know, and what.
A
Really makes us happy. Doug's like, I'll challenge you on that.
D
What is he saying?
A
Actually, my roommate in college loves cars, like, loves Corvettes specifically. And they make him very happy. Jordan.
E
I mean, there are cases in which a specific thing which you find a real sense of excitement, joy and purpose in. So if, like, if that's your hobby and you love that thing. But I'm going to guess for Em that she wasn't like a real Audi enthusiast, that it was more the fomo and she probably suffered from the hedonic adaption. She probably had some buyer's remorse eventually and realized that this money spent didn't really give me that much pleasure compared to buying a used car for something I could afford and then using it for what it was meant to be, which is to get me from place.
A
A to place B. Em, did you have buyer's remorse or in this case, leasers remorse?
C
You know, I think I wasn't really aware of how bad of the decision was until I started to learn about money because I'm like, oh, people just, this is what people do. They get new cars and oh, it's leasing is just a flexible option. But I didn't realize I'm paying to just rent something and then after this, I don't have anything. I have no car. It's a lack of knowledge and awareness of what I was even doing. And like I said, I had really bad peer pressure from someone I was dating at the time. And so I was like, well, yeah, like, yeah, new, everyone deserves new cars. And like I, I'm making grown up money now and like you get into this lifestyle creep, lifestyle inflation and I mean, it felt cool to be like, look at me, I made it.
A
But it could have been worse.
C
No one cares what you drive.
E
You could have got a tattoo. It could have been worse.
C
I, oh, I might have done that too. Well, that's another, that's another live stream.
E
Thomas could be like somewhere in your body, like this is like at least, you know.
B
No names though.
C
I didn't get names.
E
You paid your dues with the car and it was gone. Yeah.
A
No regrets. Yeah.
D
Doug M. Said something a couple of minutes ago that I want to touch on a little bit more. I'd love to hear your guys's thoughts on it, which was I think there's a considerable number of people in their 20s and early 30s who are feeling like I can't afford those life goal financial achievements anyway. So I might as well do a whole bunch of the smaller, more luxury types of things, notably houses. It's that, you know, I'm never going to be able to do what my parents did or what my grandparents did because I think that messaging is being crammed down their throats through social media. Yes. Our houses at a greater premium now than they were maybe in the early to mid-90s. Yes, they are. But I'm worried that they just take themselves out of the game entirely and choose to, to do a whole bunch of the smaller luxuries. Not realizing it's not just the maybe $550 payment now, but what that money represents 10 years later and how that could turn into a home that they could very much possibly.
A
Yeah, yeah, yeah. You take the possibility just right off the table.
D
You do. And the messaging that is coming through the mainstream media even is driving me crazy because it was never easy for any generation. You can go back 150 years. It was never easy.
A
Well, yeah, but I mean it is so much harder today. I just had a discussion with a stacker in Southern California. He needed a ten thousand dollar down payment he had to come up with now a house that he would have bought where he lives in the same general area. $1.1 million for that house. He's like, my daughter is 30 years old. She's never going to be able. I mean she's got to save over a hundred thousand dollars to get 10% down. I think it is a whole different world. But I love the idea of why take yourself out of the game? Why just go, yeah, screw it, I'm done. Not going that way. By the way, it also strikes me that for you, you said you paid your house off already.
C
We did, yes.
A
You know, they talk about, quote, good debt and a mortgage is good debt. You went from leasing a car to now I'm not even going to have, quote, good debt.
C
Yeah. Now it's so funny because we were just on the money Guy show. Our episode comes out soon and this was one of the things that got a little bit of a wrist slap of paying off our, our mortgage. But I know it wasn't the right thing to do for us on paper, mathematically because we had a low interest rate. Like I knew it. And we talked about the trade offs, but our whole goal was being debt free. Like I wanted freedom, total freedom. I didn't want to owe anything to anyone. I hate the feeling of owing something. We still balanced it out with some investing, but we just aggressively paid it off and we were earning the most that we had in our careers and it was gone and three years.
A
That's why we had to have you on, because we actually have talked about this a lot. That's not a mathematical decision. And Brian and Bo, they're just morons. I mean, come on. Really?
E
Honest.
C
I totally forgot to say hello for you. I thought. And give. And say hugs and kisses or something.
B
Hugs and kisses.
A
I do love those guys. And when they say they're total morons, but I'm being facetious. But we do often talk about how wealthy people. They're not wealthy because they're dumb. They're wealthy because they're intelligent. Yet you. Do you see all these studies that show wealthy people pay off their debt? They pay, including the mortgage, including the ones where the math is. Is bad. By the way, whenever. Whenever you have somebody at the auto dealership who is telling you about the car payment and about how all the things that you need to add and how cool you look. I mean, Even back in 2009, Budweiser was telling us how intelligent and on our team, these guys are. Let's have a listen.
D
Bud Light presents Real Men of genius.
A
Real men of genius.
D
Today we salute you, Mr. Used Car Lot Auto Salesman.
A
Mr. Used Car Lot Auto Salesman. Slick back hair, a shark skin suit, alligator boots.
D
You cultivate a look that oozes.
C
Trust me.
A
I think you stand behind every car you sell.
D
Because if you stood in front and.
A
The brakes failed, you'd be crushed. You better watch out now.
D
Oil leak. What oil leak. That puddle under the car is just sweat from all that horsepower.
A
Let the horses out now.
D
So crack open a nice cold Bud Light, Mr. Peddler of the Sheet Metal. Because when life hands you lemons, you sell them.
C
I love that.
A
That's one of my favorite. That whole series was great, but that was one of the. One of the top ones. We're gonna pause right here. We got two more Stories to go. Well, three stories to go. We got a story from Doug, we got a story from Jesse, and I have a short story as well for this special Halloween episode. But at the halfway point of every Friday episode, we have this year long competition between our three frequent contributors. Jesse's the only guy from that crew who's here representing himself today. And you're going to be representing the Paula Pant from Afford Anything. And Doc G. You are representing OG so we're going to keep the GS together, have the ladies on a team and have Jesse play for himself. M, we've got some good news for you and some bad news. Which one would you like?
C
Soften the blow here, let's. How about the good news first?
A
Well, the good news is there's no pressure because Paula is failing like she does every year at the trivia contest. Which also means it's also the good news that you get to go last because of that. See, you will have the final guess. Yeah. Jesse is in first with 12 and a half points. OG has 12 and Paula has nine and a half. So if somehow you're able to help Paula win one, she's still a long way away. So there's no pressure. Zero, zero pressure. But there is some pressure on Doc G to try to help OG Always retain his title. Yeah, it's, it's going to be tough. As we, as we are last day of October. We only have a few more of these left, everybody. We need a question though. Doug, Special Halloween episode. I'm sure you've got some special trivia on tap.
D
Oh boy, do I. Joe. Hey there, Stackers. I'm Joe's mom's neighbor Doug and I can't wait for trick or treaters to arrive. But here's the thing. The thing that drives me crazy about the whole night. I've never understood why they call it trick or treat when it's all treats. It's all treats all the time. We all have that one annoying neighbor handing out full size candy bars. No wonder no kid ever picks trick. I mean, we might as well teach some of those noisy little thieves of joy to say treat or treat. So this year I'm bringing back the trick, baby. I'm gonna turn some tricks. These little anchor bite probably shouldn't say that. These little ankle biters are about to learn why Doug doesn't lose. Now don't worry, I'm not a monster or anything. I'm not handing out raisins. That would be really mean. Instead, I filled these fake candy wrappers with the 2025 tax tables. That way, when one of these kids becomes a child TikTok star or hits the lottery, they'll thank me later. Doug's always thinking ahead. He always is. Something tells me these little whiners will still howl like a werewolf at a full Halloween moon, though. And speaking of full moons on Halloween. Pause for effect. That's actually pretty rare. Like, Doug admits he's wrong about something rare, which is never, by the way, because, true story, never wrong. So here's your question. In what year will the next full moon fall directly on Halloween? I'll be back with an answer right after I finish helping Joe's mom set up skeletons in the front yard. Between you and me, I'm doing most of the heavy lifting here.
A
You call the kids whiners. Oh, my goodness. There's a slight amount going on there. Jesse, you are first Halloween full moon. When's it going to happen again?
B
It will happen.
A
What?
B
It's 2025. It's gonna happen in 2039.
A
Clarifies the year.
E
What is?
B
Well, in the spirit of OG and Paula, I had to put in some sort of clarifying statements, mental math. So all I could think of is what year it is.
D
You did it about eight minutes faster than they usually do, though.
A
2039. Doc G. You think it's going to be before that or after that?
E
Oh, It's. It's clearly 2056.
A
2050.
E
I mean, it totally is market.
A
And we got 2039 and 2056. What are you thinking?
C
You know, I'm going to go a little like, Price is Right action here because I was like, oh, I'm going to add one on the top or on the bottom. I'm going to. I think it's going to be sooner. I'm going to say 2038.
A
2038. Good play. Nice job. We call that move, by the way, M the Chelsea Brennan. Chelsea's been on the show quite a few times, and she was the first person who did those price right moves. So you just.
C
All right, you just.
A
Chelsea Brennan, Nice job. All right, we've got 2038 for M, 2039 for Jesse, 2056 for Doc G. Who's right? We'll be right back. Jesse, you start out with 2039. How you feeling?
B
I'm feeling not great because I think M took all my downside, and I think Jordan has a good amount of my upside because follow my actual OG logic here, if I may. Isn't the lunar cycle 28 days long? So I Think any given year, there's always going to be a full moon at some point between 14 days before and 14 days after Halloween. So I think on average once every 28 years, you're going to get a full moon on Halloween.
D
So.
B
So I just took the middle. I added 14 years to 2025. Boom. 2039. But M now has all my upside, and I have up till 2053. Except that's when OG starts to. Yeah, starts to infiltrate on some of my guesswork. So if I'm thinking about it the right way, my odds are not good.
A
Doc, you've got pretty good odds then though, being in the upper end of.
E
That, I've got infinity above.
A
If it never happens again, you win.
E
And hey, it's rare. Might not happen again till 2136 for all we know. But that I got that covered too.
A
And I'm 2038. You feeling good?
C
Yeah, I mean, I feel like this Price is Right move is, is gonna, I, I, I feel like Jesse used way too much math and mind power in this one. Like you gotta just like feel it, you know, you gotta just like feel the answer.
A
So we'll see when you come back. The more times that you're on, you'll see that most of the quote math that happens during our trivia segment is smoke and mirrors, dogs and ponies.
C
Oh, Jesse sounded really smart with that answer, so.
B
Well, in your defense, I am much more astrology than astronomy in most of the things I do, so me trying to dip my toe into actual astronomy is probably not a good thing.
A
Well, let's see how far Jesse got dipped into astronomy.
D
Doug. I feel like Jesse's trying to pick us up at the bar right now, talking about astral signs and stuff.
C
Hey, at the inner the interstate rest stop.
A
Yes, right next to the Panera.
D
It was a scene.
B
Man, you look like a Capricorn, Doug.
A
What can I say, Doug? Who's gonna win this?
D
Hey there, Stackers. I'm your resident tricker and the only guy in this basement who actually gets Halloween. Joe's mom's neighbor, Doug. All right, it's Halloween, which means it's time to talk about vampires and ghosts, ghouls and full moons and why I'm pretty sure I could take a werewolf in a fight. I've got the upper body strength. I mean, just look at me. The question was, when will the next full moon fall exactly? On Halloween. So let's see how our so called experts. Heavy on the air quotes there. Let's see how they did. Well, I will tell you that it's 17 years sooner than what Doc G guessed, one year sooner than what M guessed and zero years sooner than what Jesse guessed. Because the correct answer is a frightening 2039, making Jesse our improbable winner.
C
No way. Jesse, just be honest.
E
I knew it all along, you know, Em and I couldn't win. He already got it for the first guess.
A
Yeah.
C
Astrology coming through.
B
I learned that from OG. Just take a guess and hit it dead nuts on.
A
With no context, I had to control my facial expression.
B
Sorry, guys. Sorry.
C
That was impressive.
B
It's happened before, Em. I think that's the third time it's happened.
A
I think it's happened too many times, Doug. Well, it's happened too many times.
B
Yeah.
D
I mean, he waited like what, eight or nine months between the first two times he nailed it. So he's playing the long con on us, that's for sure.
B
I think it's been over a year since I nailed one.
A
I think it has. I think it was about this time last year, wasn't it?
B
Yeah. Was it the first one I think I got.
D
Was it wrong for me to give him the question in advance? Should I have not done that?
A
It's amazing the favors Doug will do for people at a rest stop.
D
Hey, look, a sandwich is a sandwich, man.
A
I'll give you the answer to the trivia. Oh, boy. Let's go to the second half of this discussion. Please, please, Jesse, get our brain off this and tell us a horror story. Jesse Kramer.
B
Well, when Doc G started this conversation on a deathbed in hospice, I thought, man, I'm going to have to go even more serious than that. My story takes place inside of a hot tub. That's a joke. But no, my horror story is probably the first really big stupid decision I made in my financial life. At least I think was pretty dumb. Involved buying a five figure hot tub. It's kind of similar in some ways to Em's story where it's like, I was young. To me this was a cool thing and I had at least in my mind, enough disposable income to make it work. But two major failings and two major lessons that I would teach to anybody and I've tried to teach to people before. When I brought up the story, the first one is that I made the decision because we were just coming off of a fun mountain retreat with friends up in the Adirondacks that involved a hot tub. And when it's a cold winter night and you're surrounded by friends and you've had a couple beers. How much fun is it to hang out inside of a hot tub? The problem is it's hard to recreate that just in everyday life. There's this great saying out there about rent your fun, but you don't buy your fun, you just rent your fun. Because it's hard to recreate those vacation vibes just everyday life. But then the second big lesson was it was my first school of hard knocks lesson in the way that hard sales tactics work. And I can still remember this sales guy sitting in my kitchen. And amongst some of the other tactics, I still remember him telling me about his daughter's student loans and how every sale is meaningful to him and how like, you know, everything he does is for his kids. And man, you know, this, you know, it would really help out his family every time someone buys a hot tub from him. And I still remember hearing that and at the time being like, oh man, what a tough. That's an interesting story. And now after I read Robert Cialdini's book Influence, I still remember reading that book and being like, oh my gosh, these are all the things that that hot tub sales guy did to me, which I fell for. Like, it's not that he did it to me, right. I take responsibility for it. But those tactics really worked on me and it made me realize that professional sales tactics do work. And if we can educate ourselves on kind of how our brains respond to them, I think it's a pretty good defense system. So that's my scary story. Wow.
A
How much was the hot tub?
B
It was like $11,000. It was the Audi of hot tubs, if I may say so.
C
Was it worth it? Was it a really nice hot tub? I'm genuinely curious now.
B
It was a really nice hot tub. It fit like eight people. It had awesome jets. It was just very high quality. It was well made.
D
I'd better need to smoke a cigarette after I got out of that hot tub. That's how good that would have to be for $11,000.
B
That's the thing. It would probably. I mean, at this point, I'm over it. When I sold my old house, the hot tub stayed and it was kind of part of the deal. It was part of the price of the house, if you will.
E
You might have gotten 11,000 more dollars for the house based on the hot tub.
C
It was an investment.
A
It was an investment. SM winks at everybody. For those of you on audio, right.
B
To take the number of times I was in that hot tub as a denominator, take $11,000 divided by X, whatever. How many times in the hot tub and just say like per. Per soaking. How much did I pay? It is not a pretty number.
A
That's ugly. Jesse was talking about some of the tactics that the salesperson used on him. Did you get any of those tactics at the car dealer m used on you?
C
No, honestly, I can't even. I can't remember exactly how they tried to sell me on the car, but I remember it was very painless. It was very VIP and yeah, like we're gonna get you in this car. They had a lot of catchphrases that you're just like, oh yeah, okay, cool. And oh, well, yeah, you can absolutely afford the payment. These people have been trained to say all the right things and make you feel a certain way. And to Jesse's point about how I would say that was a bit of an impulse purchase. Right. He's. He was buying to feel a certain way or to evoke a certain motion. That doesn't just happen with, with salesmen or saleswomen or like these one on one face interactions. That's happening every day online too. Brands and companies, I won't name them, but very large ones that maybe start with an A. They are so good about taking the friction out of buying. It is painless to buy these things. Your card's already loaded up. One click buys it. It's in your. It's at your house in two hours. So my biggest thing in terms of a tip for that, you want to add space between you and the purchase. When you add that buffer room and that time and that waiting period, it gives you time to think about it more critically. So like a common one is like the 24 hour rule. Save it to your cart for later, give it a day, sleep on it. I guarantee I've done this so many times, like 90% of what I save for later, I end up not buying because it's in the moment that we get so excited and we want these things. And so you got to give yourself some breathing room.
B
Did you guys know this? And you, you reminded me of something there because it actually applied to my situation. Some states have consumer protection laws that for certain types of sales, especially if there is that in person salesman, you actually have a short grace period that you're allowed to literally like reneg on the contract signed.
C
Yeah, yeah.
B
And especially so it could be like cars. It. It applied in my case to the hot tub. I know, I just, I was excited and I didn't want to go back on it. But Just for that reason for some people are like wait, I, I wish I had that 24 hour shopping. But the guy really wanted me to sign in person. So for all the stackers out there.
A
That'S interesting to insurance products have that 10 day free look period where after.
D
The date does too. Remember that great scene in Glengarry Glen Ross where the guy went out and bought the real estate and his wife said you gotta go get our money back. And they just slow walked him to make sure the 24 hour period expired. But real estate I think is one of those too. Yeah.
C
I believe that also applies even to like flights. If you buy a flight, you have 24 hours, you can get your money back. Refund it too. A lot of people don't know that.
A
It is interesting. I mean I found that on vacations I used to always want a momento. I'd want a coffee mug or I'd want a beer glass or a T shirt or something. And you know what's funny? I found that if I found something clever or fun or just, just something that I thought I might want to take home, if I took a picture of it, if I just took a picture of it, it went away. It was incredible because I'm like, oh, I have the photo. I can laugh at the photo whenever, you know. You know how often I look at that photo of the funny thing that I saw on vacation that I used to bring home, that I don't bring home anymore. Never. I never, never once. It's so strange how that just completely neuters that. Almost like your 24 hour rule.
C
Yeah. And you know, that's actually a really good tip for, especially for people with children because you know, kids are going in stores like I want everything right? This, this, this and that. Okay, we're going to take a picture of this and we're going to add it to our list for our birthday, for Christmas, for this. So we'll take a picture and then we'll put it on the list and then we can go through the list of all the things you want afterwards. There's something about it. I don't know, it's almost like you're still capturing the item in some way. Right. It's not like I feel like you.
A
Still get the dopamine hit.
C
Yeah, you still get to look at it and be like, oh, that was so cool. And it kind of helps you reminisce of it.
A
I don't know, it disappears.
C
There's some psychology. Someone has to know in the comments. Maybe someone has to help us figure this out.
A
Jesse in the hot tub money machine. That's what we'll call that story.
B
Yeah, it was a. I was not bobbing for apples in there, I can tell you that much.
A
Doug. I don't know what he's talking about either. Doug.
D
I just threw up in my mouth.
B
Just trying to make it Halloween related.
D
I don't know.
A
Doug, what's your scary story?
D
Well, I've got several which will shock nobody. One that I don't know if it had real long term effects or not, but I was just feeling the moment very young. My wife and I were waiting. We were literally taking walks in the town we live in to try to induce delivery of our oldest son that we had been in the hospital for almost a week and he was not going to show up. So they actually sent us home. That's a whole separate story. But they sent us home and they're like, go take a walk. It's almost Thanksgiving. You know, there's a full moon coming. You know, this is going to happen. So we go, we're walking around town. It's pretty nice to nice town that we were walking around. And we happened to stop into an eyeglass store that had some pretty nice pieces and one of which were antique glasses that were at the time in the early 90s. Well, mid-90s were about $1400. I think that's roughly three grand now, maybe two, 800 bucks now. And we were just feeling great. It was this beautiful fall day and we were excited for the birth of our son and thought, yeah, that seems like a really good idea. That that's an incredibly stupid idea. And the thought of what could have happened with that, you know, 2, 800 in today's dollars. What could have happened with that? I still have buyer's remorse. I didn't at the time. It took a long time for me to have buyer's remorse about that. I wore the glasses for years. No one told me, including you, that I looked like a fat John Denver in these glasses.
A
Why are you pointing to me?
D
Because you, I knew you then that.
A
I never said, there goes fat John Denver though.
C
We need a picture now. We need a picture of these glasses.
D
When I think back on it again, there are some stories that aren't horror stories until years later when you realize what the opportunity cost was for some of those decisions. So that's an early one that come to mind. And you might have said this. I'm making adult money now. I feel like I can make adult decisions and adult purchases and I think that probably fell into that category. And I would say to our younger listeners, don't fall into that trap. It's a super easy one. I did the car thing, like so many. I'm from Detroit. You're supposed to have cool cars. It's part of the culture. It's so easy to fall into that early in your career.
A
It strikes me between M story, Jesse's story, and your story, Doug. It just reminds me of when TikTok star Buffy Purcell was on the show and said. And you. You kind of said this too, but she just said it very succinctly. The most dangerous phrase for a broke person to say is, I deserve it.
C
It.
A
The most dangerous phrase, just 100%. Speaking of, I have my own sales tactic nightmare. I went to Midas muffler when I was a. When I was a senior in high school, I had this old Monte Carlo that was just falling apart. In fact, it was so bad, you know how, like, the glue on the ceiling doesn't stick anymore, and so the. The ceiling just kind of hangs down. Yeah. I put my own stereo in the car, and I didn't understand what the ground wire was for. And so to get it to work, I had to turn on the car. I turned on the car. I didn't realize I had all these electricity running through my body. And then I turned the car off. I got shot out of the car, just fell on the ground outside the car as the electrical system was no longer running through me. But that's not my horror story. The horror story was I go into Midas with this horrible car. The guy who's working on my. Who's going to work on my car is like, you know, instead of just a muffler, I think this thing. You could really restore this car. Like, this car could be awesome. And he goes, I'm actually working on my car out back. Come on out back. And he shows me, and he's got this engine he's taken out of his car, and it is all shiny. It's so beautiful. And then he shows me his car that he's restoring, and he goes through it. He's like, you know, you could be doing this with your car. So I buy this package where I buy the sport struts and the sport shocks, and I get the upgraded muffler system. I get all this stuff. I have no idea what this guy's doing. Right. I get back to the waiting area and I sit down and the receptionist takes out the phone book. They'd have the old phone book and she goes to the back of the yellow pages where they have all of the coupons in the back. She cuts out a coupon for that place and hands it to me and just gives me this knowing look and goes, you're gonna want this, honey. You're gonna. You're gonna want this.
C
Oh, no, she's.
A
The receptionist is telling me I'm getting ripped off. I have no idea. I'm a high school kid and so I'm like, wow, that's. She's so generous and that guy's so nice. This is it. This is incredible.
D
I get home, she didn't. She didn't stop you from jumping. She just handed you a pillow to soften the land.
A
Yeah, she did. Well, I think if she would have told me I was getting ripped off, the guy would have fired her.
C
Yeah.
E
Jordan, you know, it's interesting. I find it really funny. Most of these stories are stories that really burn you because you spent when you shouldn't have spent. But if we really think about it, the really scary stories often aren't that. It's like, I didn't get the life insurance and I should have, or I didn't change the beneficiary, or I listened to that guy who said that I should put all my money in this new business and I lost everything. It's funny because most of these are really survivable and I guess in a sense it's actually, it's a blessing. Like, we walk away from these feeling burned, but hopefully we learn from them. There are these really catastrophic things that happen to people when they just make unfortunately really dumb decisions or non planned out decisions. I kind of like the fact that we can look at all these and be like, yeah, I got some egg on my face. But you're all probably better people for it. In the end.
A
I think it's a great lesson there and I think that's probably a great place to end this discussion because I do think, you know, we're all here. We all survived. Jesse survived the hot tub. M survived the Audi. I survived the mighty small floor shop. My dad gave me hell when I got home, by the way. He's like, you're a.
B
You just.
A
That car where the ceiling doesn't even stick has sport shocks and struts. Really? You can't even sit in the car yet. It cornered great. After that, it's fantastic. We'd love to hear your stories. What are your money? Horror stories. Join our Facebook group mom's basement stacking benjamin.com basement it's a good shortcut to get you there. We set up a link that takes you right to the group. Let's share some more of our stories. If you, by the way, have a question about a money story that you have, head to stackybenjamins.com voicemail and call in with that question. Love to hear those as well. If you're not sure how to get out of a money story that you just you want to make it in, we will help you there too. Speaking of help, we'll help you one more way. We're going to help you by sharing all the good places you can go to find out other stuff because all three of these awesome creators have things that you can follow. Let's go to our special guest first. Em, thank you so much for joining us. This has been a blast.
C
Thank you. I honestly, I learned a lot talking to everyone and thanks so much for having me. And hopefully I can come back and start getting those points for Paula because I was so close. I was this close.
A
Jesse, if Jesse hadn't cheated, you would have won. That's, that's your own horror story for, for Halloween. So what's coming up on your channels? What kind of stuff do you have that people can look forward to if they follow you on Tick Tock?
C
Yeah, yeah. I have a lot of great resources, especially for very beginner friendly resources because money can be really overwhelming, especially in the finance industry and all the jargon. So definitely come to my page, check out those resources. They're completely free. I think the next biggest thing for me is next Monday our episode on the Money Guy show is going to be live. So we're going to put out all of our money and we're going to talk about can we actually retire at 40? And so like that's going to be a really big, exciting update and hopefully it'll help teach some people a few things in the process.
A
Your second best podcast appearance. That's what you're trying to say?
C
Absolutely. This is first and foremost, Jesse Kramer.
A
What'S going on at at the Better Interest Blog, the Personal Finance for Long Term Investors podcast. What do we got coming up, my friend?
B
A show about money, maybe. What is going on? I think October, it's what today's October 31st. Right? October has been our best month ever on the podcast in terms of listeners. And, and I will say part of that is because we've gone to three episodes a month. So when you increase your episode count by 50%, you tend to get more downloads. But still we have math.
A
There too.
B
There is some math there. We're now doing one Ask Me Anything a month, which are kind of the most popular episodes. One Deep Dive. This Deep Dive, this month's Deep Dive episode was about special needs planning, planning for a special needs child, which is a really interesting topic. And for any parents out there who have a special needs child, you'll know how much, much complexity goes into that task. And then upcoming next week, I've got an episode coming out with Professor John Dinsmore. Really interesting stuff about the marketing of debt. So he talks about like credit card marketing, the marketing of loans. We even touch on like the marketing of sports gambling and stuff like that. And it kind of ties into some of the sales and poor spending decisions we are talking about today because it really is this marketing and advertising machine behind the financing industry which isn't always targeted in our best interest. So that's what's going on over on.
A
Some podcast about money, personal finance for long term investors. I can say it, right? I just apparently chose not to. Doc G. How about over at the Earn and Invest podcast?
E
At Earn and Invest, we just had Alana Golan on from the Leap Academy. We talk about portfolio careers, the world of corporate America, careers, making a living. It's all changing. We used to look at iq, then we started looking at eq. She talks a lot about aq, your ability to have agility, to move, to change, to shift, to pivot. And so how do you build a portfolio career? We talk about it on Earn and Invest.
A
Wow, you guys are all working on such cool stuff. Can I come live where all three of you live? Fantastic. And we will link to all them in the show notes@StackAndBenjamins.com all right, as always, Doug, you are wrapping up this baby for us. What should be on our to do list today?
D
I'm not working on anything cool, Joe, but I do know there were three things we should have learned today. First, take some advice from our guest, Auntie M. If you know you're gonna look like a movie star driving around in a brand new El Camino, it absolutely makes sense to lease a car. In fact, go ahead and use your emergency fund to reduce those monthly payments.
A
Oh, God no.
D
Second, don't forget the insightful lesson from Jesse. Hot tubs will absolutely enhance your home's resale value. But the big lesson, don't let those little con artists take your candy corn without breaking a sweat. Make them do a trick by like cleaning out your gutters or changing the oil on your snowblower before you hand over the good stuff. Thanks to our good friend Emily for joining us today. You'll find her channel hey friend, it's em on TikTok and Instagram. Follow her for great tips and financial fun. We'll also include links in our show notes@stackingbenjamins.com and thanks to the Jesse Kramer for hanging out with us today. You'll find his fabulous podcast Personal Finance for the Long Term Investor wherever you listen to Finer podcasts. That's the name, Joe. Remember it?
A
Long Term Investors.
D
Yeah, I mean, that could, that could work too. It sounds pretty good. Thanks also to Doc G for joining us today. You'll find the irresistible Earn and Invest podcast where I had to think about that. Like, is it irresistible?
E
Nice pause.
D
Nice pause. You'll find the irresistible Earn and Invest podcast wherever you listen to podcasts. Anywhere. This show is the property of SB Podcast, LLC, Copyright 2025 and is created by Josal Sehive. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome team@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. Oh, yeah. And before I go, not only should you not take advice from these nerds, don't take advantage of 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 Benjamin Show.
Episode: Tales of Financial Horror (and how we exorcised them) SB1755
Date: October 31, 2025
Host: Joe Saul-Sehy
Guests: Doc G (Earn & Invest), Jesse Kramer (Best Interest Blog), Emily Agashira (Hey Friend, It’s Em), and Neighbor Doug
This special Halloween episode of The Stacking Benjamins Show turns the basement card table into a virtual campfire, with Joe and his guests sharing real-life “financial horror stories” – tales of money mistakes, bad purchases, and the hard lessons learned. The panel—Doc G, Jesse Kramer, and TikTok/Instagram star Emily Agashira (“Em”)—reflect on how these financial frights taught them resilience, caution, and a dose of humor. The episode maintains Stacking Benjamins’s signature warm, teasing style, mixing laughter with meaningful money takeaways.
“For you to get as far as you have with your money, like you’ve just done everything perfect. M. Everything’s perfect for Em and her family all the time.”
— Joe Saul-Sehy [05:13]
“If his dad had remained alive but on the ventilator and incapacitated, (Dan) would have had to go to the court systems and try to take over their financial control. And that can cost lots of money and a lot of time.”
— Doc G [09:43]
“I had the mentality of if I can afford the payments, I can afford the car. And that is such a common theme that we…see and hear a lot nowadays.”
— Em [19:14]
“I made the decision because we were just coming off of a fun mountain retreat with friends… It’s hard to recreate those vacation vibes in just everyday life.”
— Jesse [39:32]
“There are some stories that aren’t horror stories until years later when you realize what the opportunity cost was…”
— Doug [48:34]
On the danger of “I deserve it”:
“The most dangerous phrase for a broke person to say is, ‘I deserve it.’”
— Joe [49:26, referencing Buffy Purcell]
On “good debt” and paying off her mortgage:
“Our whole goal was being debt free. I wanted freedom, total freedom. I didn’t want to owe anything to anyone…”
— Em [27:26]
On rationalizing payments:
“It was my first school of hard knocks lesson in the way that hard sales tactics work.”
— Jesse [39:37]
On survivable mistakes:
“Most of these stories are stories that really burn you because you spent when you shouldn’t have spent… but hopefully we learn from them.”
— Doc G [51:45]
On estate planning inertia:
“If you don’t have a will, the state has a will for you. You do have a will.”
— Joe [16:05]
On the illusion of perfection:
“People think that for you to get as far as you have with your money, like you’ve just done everything perfect. M. Everything’s perfect for Em and her family all the time.”
— Joe Saul-Sehy [05:13]
On the comfort of finally planning for the future:
“It shocked me how much better I felt. I was blown away by how all of a sudden… I felt so good. I was like, I never thought I’d feel this good. I thought I’d feel morbidly bad because I was acknowledging death…”
— Joe Saul-Sehy [13:01]
On opportunity cost:
“If Emily now knew what I knew back then and I invested $550 every month, I mean, we’re talking serious money.”
— Em [21:51]
On succumbing to sales tactics:
"It was my first school of hard knocks lesson in the way that hard sales tactics work. And I can still remember this sales guy sitting in my kitchen... telling me about his daughter's student loans and how every sale is meaningful to him..."
— Jesse [39:37]
On learning from mistakes:
“You have to put your hand on the stove once to know to avoid the stove later on in life… Thank God this was a recoverable mistake.”
— Doc G [22:31]
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Signature show elements like trivia and playful ribbing abound, but this summary focuses on the episode’s heart: candid, educational, and often hilarious stories of financial mistakes and the wisdom gathered from each scare.