Before you charge into a new year with fresh goals, shiny spreadsheets, and unrealistic optimism, it’s worth doing the one thing most people skip. Looking back honestly at what just happened.
Joe Saul-Sehy, OG, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) gather for an end-of-year roundtable to unpack the financial, personal, and behavioral lessons that 2025 handed us. Sometimes those lessons arrived gently. Sometimes they shoved us face-first into reality. Either way, this episode isn’t about predictions for what’s coming. It’s about understanding the patterns from what already happened.
The team digs into what diversification actually meant this year when some of the old rules stopped working the way they used to. They explore why emotional reactions to headlines still cost investors real money, even when everyone knows better. And they examine how policy noise (tariffs, political drama, market freakouts) reminded us once again that short-term chaos rarely deserves long-term decisions.
Along the way, the conversation touches on housing lessons learned, family priorities that got re-examined, and AI’s quiet but growing influence on work, productivity, and opportunity. The thread running through it all? Financial planning only works when it serves the life you’re trying to build, not the other way around.
This episode balances big-picture thinking with real-life reflection. It’s the kind of honest look back that actually helps you move forward smarter instead of just louder.
What You’ll Walk Away With:
- The most important financial lessons 2025 taught investors, whether they actually listened or not
- How AI quietly changed work, productivity, and opportunity in ways that matter for your money decisions
- Why diversification looked different this year and what investment principles still held up under pressure
- How market volatility exposed emotional blind spots you might not have known you had (and how to fix them)
- What the housing market taught us about patience, expectations, and timing
- Why year-end reflection beats year-end predictions every single time
- How family dynamics, personal values, and money planning intersect more than anyone likes to admit
This Episode Is For You If:
- You want to learn from 2025 before setting goals you’ll abandon by February
- You made some money decisions you’re proud of and some you’d rather forget
- Market headlines changed your behavior this year and you’re wondering if that was smart
- You’re tired of prediction content and want actual reflection on what already happened
- You believe getting smarter about money means being honest about what you got wrong
Before You Hit Play, Think About This:
What money decision in 2025 are you most proud of, and which one taught you the biggest lesson? Going into 2026, what one financial habit would make the biggest difference if you actually stuck with it? Bring those thoughts into the Facebook group or drop a comment because your reflections might help another Stacker avoid learning the same lesson the hard way.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Our Topic: Our Biggest Money Lessons of 2025
During our conversation, you’ll hear us mention:
- 2025 year end lessons
- Holiday season banter
- OG birthday confusion
- Identity theft jokes
- Porn name gag
- AI job disruption
- Human connection skills
- Skillset diversification
- AI hallucinations
- Unreliable narrator
- Legal advice warnings
- Medical advice warnings
- Black Friday deals
- Google AI summaries
- Banana Ball tickets
- AI as starting point
- Diversification matters
- International stocks rebound
- Nvidia concentration risk
- Reversion to mean
- Crypto volatility
- Emergency fund basics
- Tariff tantrum drop
- Dollar cost averaging
- Ignore market headlines
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
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 Apple Podcasts.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
Paula Pant
Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paula on Twitter: @AffordAnything
OG
For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- What is Clark Griswold’s bonus specifically in National Lampoon’s Christmas Vacation?
Join Us on Monday!
Tune in on Monday when we welcome the hosts of the How to Money podcast, Joel Larsgaard and Matt Altmix.
Miss our last show? Check it out here: How to Give Back Without Being Rich + Building a Smarter Retirement Plan (SB1775).
Written by: Kevin Bailey
Episode transcript
[00:00:00] bit: Can I refill your eggnog for you? Get you something to eat? Drive you out to the middle of nowhere. Leave you for dead. No, I’m doing just fine, Clark.[00:00:12] Doug: Live from the basement of the YouTube headquarters. It’s the Stacking Benjamin Show.
[00:00:27] Doug: I am Joe’s mom’s neighbor, Doug. And as we wind down 2025, it’s important to ask what could we have learned from the events of this year? Today we’ll ask that question of our round table contributors so you can manage your money better next year. By learning from history and now a guy who’s wrapped up all the holiday cheer and placed it right into today’s podcast.
[00:00:51] Doug: It’s Joe Saul Sea,
[00:00:56] Joe: and of course, it’s one first time. Of course, it’s the one that the fewest number of people are going are gonna hear. Hey there, stackers. Happy holiday season. Happy Hanukkah. We’re right in the middle of it. Happy, pre happy. Whatever you’re doing this holiday season, we’re so happy to be here with you with one of my favorite episodes of the year, which is, as Doug so succinctly said, 2025 lessons for a better 2026.
[00:01:24] Joe: Now, if you had interpreted that as 2025 lessons, they’re just lessons from 2025, so to be clear there, but we have a group of Roundtable participants who are helping us. Say goodbye to 2025 and let’s start off with the gentleman across the card table from me. Mr. OG is here. How are you man? I’m full of Christmas.
[00:01:49] Joe: Joy,
[00:01:50] OG: obviously you are absolutely full of Christmas joy because of the fact, as you can tell in my
[00:01:57] Joe: demeanor.
[00:01:57] OG: Glowing, glowing commentary.
[00:02:00] Joe: Well, seeing how it is the day before your birthday.
[00:02:03] OG: It is not the day before my birthday, but that’s cool. It’s
[00:02:06] Doug: not, it’s four days before his birthday, four days that before your birthday that
[00:02:08] OG: it’s not four days before my birthday either.
[00:02:10] OG: But you guys are good. It’s, you’re in the ballpark and that’s all that counts ish. Is it two days before? I’m not gonna tell you it’s gonna be a surprise happen this
[00:02:18] Joe: year.
[00:02:19] OG: Has it already happened?
[00:02:21] Joe: Have you, have you stopped having them? Or is it still
[00:02:23] OG: yet to happen? That is the question. What’s the over under on OGs birthday?
[00:02:27] OG: I picked December 19th.
[00:02:29] Joe: This is what happens when a bunch of dudes decide to, to figure out like somebody else’s birthday. Like I, I could, could we even figure out her own birthday?
[00:02:36] OG: All I know is that I could have 10 more birthdays and still not catch you guys. So that’s all that matters. Easy.
[00:02:42] Joe: Somebody who it feels like it’s our birthday.
[00:02:44] Joe: Every time we get to spend a podcast with her, Paula Panta is here.
[00:02:49] Paula: Well, you know, once we have OGs birthday, we’ll be that much closer to stealing his identity.
[00:02:53] OG: That’s right.
[00:02:54] Paula: I’m just gonna need your mother’s maiden name. Uh, last four digits of your social.
[00:02:58] OG: Interestingly enough, it’s Snuffleupagus
[00:03:03] Joe: OG for today’s trivia question, what was the name of your elementary school?
[00:03:08] OG: And the last four of my social are? Yeah. Six seven. Six seven. Your,
[00:03:13] Doug: your, your porn name is your childhood pet’s name and the street you grew up on. Go. And how are
[00:03:20] Joe: we making all the jokes without this guy here? Actually,
[00:03:23] OG: that’s a really good porn name. Bosco McKinley.
[00:03:26] Joe: It’s,
[00:03:26] OG: wow. Is that not awesome?
[00:03:29] Joe: That is good.
[00:03:30] Joe: And the Bosco McKinley of this podcast is here could be
[00:03:33] OG: my new, my new Twitter handle. Find me at bosco McKinley and subscribe to my only chance, Jesse
[00:03:38] Joe: Kramer.
[00:03:39] OG: Call me Bosco. Right? I mean, come on,
[00:03:42] Jesse: just call me
[00:03:43] Joe: Bosco. What would that make your poor name, Jesse?
[00:03:46] Jesse: Um, what would it, uh, Harry Longwood, no, it’s not my dog’s name and then the street I grew up on.
[00:03:55] Jesse: Harry Longwood.
[00:03:58] Joe: That is, there’s no way that’s real. I’m sorry. I’m sorry. Harold.
[00:04:01] Jesse: Longwood Avenue, if we’re being Longwood Avenue would be my last name. But
[00:04:05] Joe: to you, it’s Harold. Yes.
[00:04:07] Jesse: Correct. Correct. Right. Mr.
[00:04:09] OG: Longwood.
[00:04:10] Joe: Well guys, we got a great show today because as you can see we are fired up because it getting any better than
[00:04:14] OG: that.
[00:04:15] OG: Just so everybody knows,
[00:04:17] Joe: it is our last round table of 2025. We always have a tradition here at Stacking Benjamins in mom’s basement. We look back on the year we go, what were some of the events, either personal events or events that were global, maybe events just in the city where each of our contributors lived, whatever it might be, and how can our stackers all learn from those events?
[00:04:39] Joe: So that’s what we’re gonna cover today. So grab a piece of paper, think about whatever your events are. If you’re hanging out with us on YouTube today, give us some of your events as well. We’d love to cover as many as we can do in the next hour at halfway point, because of the fact that Mr. Jesse Kramer is the winner of our year long trivia competition between our three contributors.
[00:05:02] Joe: You know what we’re doing today. We are involving our YouTube audience in today’s trivia question. So we’re gonna ask everyone a question. Our contributors a question, and we’re gonna have one of our YouTube stackers that each of our contributors will pick, and they’ll play for a chance to win a huge prize, a huge prize, Doug, that we will we’ll share later.
[00:05:23] Joe: But first, we have a couple sponsors who help us keep on keeping on. We’re gonna hear from them. And then Paula, OG and Jesse are gonna dive into the events of 2025 that we can learn from and maybe have a better 2026 because of it.
[00:05:45] Joe: Alright, let’s start off with, uh, let’s go to Paula. Let’s go ladies first. So Paula, either from your own experience or from just the news, what’s an event in 2025 that maybe we can all learn from?
[00:06:00] Paula: I think one of the major stories of 2025 is seeing how AI played a bigger and bigger role in the world. And in doing so, encroached upon many more jobs in a more threatening way than, uh, a lot of people had, I think anticipated even as compared to what people were thinking in 2023 or 2024.
[00:06:20] Paula: Diversifying your skillset at work and prioritizing the human connection, human relationships, things that a machine cannot or AI cannot replicate. I think that is a major lesson of this past year.
[00:06:37] Joe: It’s funny, Paula, because I made a list and I had to fold it over so I don’t show everybody on YouTube. My second one, but my first one, if you could read my sloppy handwriting, says AI advancements.
[00:06:48] Joe: Ooh. That was like the top of my list too. ’cause that truly was a huge thing this year that I think, Jesse, there’s a bunch of lessons there, even beyond what Paula was talking about.
[00:06:58] Jesse: I don’t know if I’m nervous or more nervous or more excited about all the changes that AI is bringing to the workplace.
[00:07:05] Jesse: Just a second. Paul’s thoughts. I mean, certain things that we all do at work are likely going to become so much easier that you could just say, oh, AI’s gonna replace me in that aspect of what I do. So, um, I’ve heard a lot of, a lot of people talking about identifying those things that are, are either unique to us or just uniquely human and trying to double down or just make sure that we are bringing value to the workplace in those areas.
[00:07:29] Jesse: And then, you know, kind of adopting AI where we can just to become more efficient in, in the other areas.
[00:07:35] Joe: Yeah, it’s funny ’cause this was, it’s been a lesson with any advancement OG that I know you and I have gotten a lot of coaching from this group called Strategic Coach and everybody’s always afraid of the next thing, right?
[00:07:45] Joe: And this is clearly something where a lot of people have lost their jobs. You on board with fear and excitement or just excitement.
[00:07:54] OG: I don’t have any fear of AI except for the like downfall of all mankind and just about everything everywhere. So other than that, I think it’s gonna be okay.
[00:08:05] Doug: Yeah. If you don’t mind, planes dropping outta the sky.
[00:08:07] Doug: I’m sure it’s fine.
[00:08:09] OG: Yeah. As long as we’ve learned to teleport and we can come back from the future to shut down Skynet before it takes over and launches the nukes, that would be fantastic. Yeah. I mean, this is not a new thing. There has been advancement in the job market and, and industrial and medical and everything since the beginning of time.
[00:08:32] OG: Many, many, many years ago. Used to just take a piece of metal and dig in the ground and plant your own stuff, and then you hooked it up to a bunch of animals and then they did it, and then you got rid of the animals and you had. Tractors that did it, and you know, and now we have faster, bigger tractors that do it, and now we can, this has been going on since the beginning of time.
[00:08:54] OG: Everybody tries to improve the efficiency of different things.
[00:08:58] Jesse: I think I remember, yeah, episode one you guys were talking about using the wheel, right? Well, they were. Wow. How, how do you use
[00:09:05] OG: the wheel in your day job? Wow. They, they started it. They were there when it was created. I was a kind of a second generation wheel.
[00:09:12] Joe: Well, I apologize, I could take a second to rename today’s podcast. Jesse’s last appearance.
[00:09:18] OG: Yes. It’s been very nice knowing you, Mr. Kramer. You know, and so people poo poo this and say like, oh, it’s gonna take jobs. It’s like, well, but that’s what everything has been trying to do since the beginning of time.
[00:09:28] OG: If you own a business and you have the opportunity to make more widgets for a lower price, you know, you wanna figure out how to do that. Whether that’s improving the efficiency that people who make the widgets, or if it’s investing in a machine, look at what. Uh, McDonald’s. I went to McDonald’s a couple of weeks ago, a month ago.
[00:09:46] OG: For the first time in a long time, there was nothing there. It was like a little counter. There was no people. There was one person who would like go to the back and get the bag and put it up front. There wasn’t like the whole cadre of people. You went in, you ordered on a screen and you stood there and somebody would walk up with a bag and go 81 and you’d grab it and walk away.
[00:10:07] OG: I don’t know how the food was being made. I don’t know what happened there. I didn’t probably save any money, but I bet McDonald’s is making some more money doing it, you know? And if you’re a shareholder at McDonald’s, you’re happy that they’re doing that because you’re gonna live bit more profit, you know?
[00:10:20] OG: So there’s a balance, obviously, between people’s jobs and that sort of stuff. But if you’re stuck in that, or if you’re at the spot where you’re like, oh crap, my job might go away, you should probably get after it. Which
[00:10:31] Joe: of the consulting companies this year, this is another related headline. Said publicly about how much money they were able to save by using ai, and then their clients started coming to them going, well, we hired you, so really shouldn’t we be the ones getting the savings?
[00:10:48] Joe: I don’t remember which, which company that was. Was it McKinsey? I don’t know. I thought I remember
[00:10:54] Doug: KPMG, but I, I, yeah, it could have been KPMG, but it, it was, it was one of the bigger ones,
[00:10:58] Joe: but I thought that was great. The consultants needed to shut up and go. Yeah. Oh man, not as much.
[00:11:03] OG: Look at how easy my job is now with ai.
[00:11:05] OG: I don’t have to like, do anything.
[00:11:06] Doug: I just paid $225 an hour for that kid who just graduated from college last week, and all he did was use Chad GPT
[00:11:15] Joe: Us Ossie is hanging out with us and said they had the same experience, uh, OG at a movie theater where there, there is now, you know, just everything mechanized.
[00:11:24] Joe: Paul, another thing that I saw this year, I was surprised to see how many different ways people used ai, some incredibly creatively that we would’ve never thought about, but other ways I think that are just a huge mistake because I get the feeling a lot of people using AI don’t understand how large language models even work.
[00:11:43] Joe: And so they’re asking AI to do a ton of stuff and coming out with these horrible results because they really don’t get what’s behind the machine.
[00:11:51] Paula: Well, AI can sometimes give outputs that seem so confident and seem so well formed that you forget that it might be hallucinating, just like Doug might be hallucinating.
[00:12:07] Joe: Wait, is that Doug? You’re hallucinating or you got results where it was hallucinating?
[00:12:11] Doug: No, no. That’s pretty much how I’ve lived my whole adult life. Which hallucinating just sound like you know what you’re talking about. Everything’s kind of foggy all the time anyways. But if you can just put up a good front, be very confident about it.
[00:12:24] Paula: Yeah, it’s important to have those occasional reminders. Like don’t get legal advice from ai. Don’t get medical advice from ai. You can try to have some educational conversations with it, but know that this is a, um, what’s the word, uh, for a narrator? Ir, not ir, reliable. Morgan
[00:12:43] Doug: Freeman.
[00:12:44] Paula: Un
[00:12:44] Doug: It’s the unreliable.
[00:12:45] Doug: Un unreliable. Unreliable, yeah,
[00:12:47] Paula: unreliable. Know that it’s an unreliable narrator. Prone to hallucination.
[00:12:51] Joe: Well, and we had Robert Farrington on earlier this year. Robert was talking about how often it gives bad financial advice because when it’s looking at the world of personal finance, it’s gonna look at the web and go, okay, 95% of the answers are X.
[00:13:06] Joe: And if something just changed last week, you’re gonna get the wrong answer. I know we did during Black Friday week, we had, uh, guests telling us that people were trying to use AI to find Black Friday deals. And maybe you can create a prompt that gets you there, but the chance that you’re gonna hallucinate on that, trying to find a deal that is only for a couple days is gonna be so like you’re asking it to make mistakes.
[00:13:29] OG: My favorite was, ’cause I put AI on here too, I tried to cheat because I don’t like doing homework. And I was like, I’ll just put this into Chet GBT. But I was thinking about it and I thought, okay, well what, what are the themes of 2025? And then I said, when is your last. Updated narrative like memory, like where are you current to, it was like, oh, I can talk about anything till October of 2024.
[00:13:56] OG: Like, oh hell, like you’re way off, bro. It’s an unreliable narrator who has hallucinations that’s been in a coma for 12 months. Yeah, this is, there’s nothing good about, like, you can’t use contemporary information
[00:14:10] Paula: like the Legend of Sleep. It’s a Rip Van Winkle. Mm-hmm. Exactly. It’s like Rip Van Winkle hallucinating.
[00:14:15] Paula: Yes.
[00:14:15] Joe: Well, and I’m wondering too, I mean, look at the number of, uh, things we saw in the news about ai, just getting it wrong. Paula, you brought up, don’t ask it for legal advice. I mean, there was a famous headline about that legal team that clearly used chat, GPT or one of the AI systems, and it was making up case law.
[00:14:33] Joe: Like it just, it just made, yeah, made, made up all this stuff that didn’t even exist. In fact, I was wondering OG, if when you looked up chat, GPT, if it said number one was ai, like I’d be super confident for AI to tell you. I didn’t put it in
[00:14:47] OG: there because the first, my, my first question was where are you?
[00:14:50] OG: Yeah, current till.
[00:14:51] Joe: Yeah.
[00:14:51] OG: But I went to a couple of ’em and they’re all like late 20, 24. So anything that’s happened literally this year is not current in terms of its information I mentioned in the preamble to this that I got selected for tickets for Banana Ball at, uh, Kyle Field. Excellent. In May. So I get to like, try to get some tickets.
[00:15:13] OG: I got selected to try to get some tickets. I, I don’t. Maybe I’m over excited, but it used to be you might might get tickets now. You might get tickets. Now I might get to buy tickets. Yeah, right. But when I put it in Google, ’cause I was like, you know, is this a real email or whatever? It literally the, you know how Google has an AI summary it, it literally was like, there is no confirmed information about the bananas playing at Kyle Field and College Station anytime in the future.
[00:15:35] OG: And I’m like, the link above it was from Texas a and M’s. Athletic department that said, great news, banana ball at Kyle Field, May 2nd, 2026. Yeah. Like Google hadn’t even got to that yet. It hadn’t indexed it enough or there hadn’t been enough searches or however the hell that works behind the scenes to make that a relevant outcome.
[00:15:53] OG: Google still thinks now there’s nothing. So my lesson for AI is. It’s a starting point, not at ending point.
[00:16:01] Joe: I think that’s great advice. I’d subscribe to masterclass and I took the masterclass on this. It was really good. So if you have masterclass, take the masterclass because the, the thing you talk about OG is nowhere the, they call it the jagged edge.
[00:16:13] Joe: The more I’ve used ai, which is now a bunch in 2025, it’s amazing how much more, how much I’ve used it this year. You truly know when you hear some of the searches people are doing, some of the prompts they’re using, you’re like, oh, you’re asking it to be wrong. There is no way that that’s gonna work well for you.
[00:16:28] Joe: Let’s keep you here OG and hear what your big event of 2025 might be. That can help us with a better 2026.
[00:16:36] OG: Mine was ai. Do I have to have more?
[00:16:42] OG: No, I’m just kidding. That’s it. Everybody onto Jesse and scene. So I’ve got a personal one that I, I’m gonna use that one last, got two tied for two. There’s an easy one. There’s, I think they’re both easy layups. I’m gonna say diversification still matters. From an investment standpoint, you know, at the beginning of the year, and I would say even for the last probably 10 years, it’s been really hard for an investor to rebalance into areas outside of large US tech, whether you mean that as the s and p, your s and p fund or whatever, but specifically in international and emerging market, going like, Hey, this is an area of the economy that we still should participate in.
[00:17:23] OG: And even though NVIDIA’s kicking everybody’s butt right now, we should still rebalance. And at least as of when we’re recording this, international is beating the stocks off of the US market. And the beginning of the year, if you would’ve said, Hey, I got a great idea. Let’s put all our money in international, or let’s up our international allocation.
[00:17:41] OG: People look at you like you had three heads, you know, or I got a bonus, I think I wanna put this all in the market. What should I do? Oh, let’s put 30% international. Be like, eh, nah, I don’t think so. I have 30% in Nvidia call options. 200 for November of 2025 maybe. Let’s do that. I think it’s just another great example in conjunction with the other layup that I’m sure somebody’s gonna have of diversification matters and time in the market is the most important thing, so keep it simple.
[00:18:11] Joe: Jesse, you talk about investing quite a bit and we had to do two shows this year reminding people not to sell off your international Yeah. Like when you start seeing at the end of 2024, is international dead forever? Yeah. That to me represents a buying opportunity in whatever the dead asset class might be.
[00:18:29] Jesse: Yeah, I mean, it is just funny, I was just talking to someone today about sometimes the, the hardest times to make an investment decision also in, in hindsight end up being the best times to have made a particular investment decision. And this was in reference to the tariff tantrum, which maybe we can come back to later.
[00:18:46] Jesse: But yeah, there, there are so many times where, uh, I mean, John Bogle would say that an iron law of investing is reversion to the mean, which would mean that when a particular asset class is kind of like at its worst, at its ugliest at the time when you’d think yourself, ugh. Like, why would I ever wanna buy that thing?
[00:19:02] Jesse: That’s probably about the same time as when it’s going to start reverting back to its long-term average and end up being an out performer in the future years. And vice versa can be true too, which is that. When certain stocks or asset classes or whatever are at their sexiest, that might be the time when they’re also overvalued and are about to revert back down to their long-term average.
[00:19:24] Jesse: So, uh, you know, I totally support everything OG just said about maintaining a diversified portfolio is accepting the fact that at any given time some of the things you own are going to be losers, and yet when you zoom out to the long run, it’s one of, if not the smartest way to approach your investing.
[00:19:40] Joe: Paula, you know, at the end of 2024, we had the international thing that we just talked about, but on the other side you call it for crypto this year, look at the rundown in Bitcoin. I mean, all the people going just load up back the truck up and this thing’s going to the moon.
[00:19:55] Paula: Yeah, and I mean really the story with crypto this year was a story of volatility.
[00:19:59] Paula: Like we saw huge gains and then, and then you’re like, man, why didn’t I short it? I mean, you can confirmation bias that in either direction, depending on where you stand on crypto. The fact that you can confirmation bias it no matter where you stand, shows that the true story is simply one of volatility.
[00:20:18] Paula: And I think that’s another lesson of 2025 is like volatile asset classes are, are going to stay volatile. And often when a volatile asset class is really skyrocketing, it’s tempting to believe that it is safer than it actually is because you want to believe in the optimistic narrative.
[00:20:38] Joe: All these numbers OG on increasing debt in the country.
[00:20:42] Joe: And we just covered AI and you know, innovations. Julie here talking about the innovations like we talked about earlier with movie theaters and, and companies and all kinds of AI business reforms that have happened. All of that. Does that mean that 2026 also means cash is an asset class more important than ever?
[00:21:03] OG: I mean, for what?
[00:21:04] Joe: Just because you don’t know if you’re gonna lose your job. You don’t know what’s coming around the next corner.
[00:21:10] OG: I mean, no, I don’t think it’s any different than any other period of time. Why would you all of a sudden start suddenly piling up cash? Because you have a feeling that the market’s gonna take a crap.
[00:21:23] OG: I mean, listen, if you think that you’re gonna lose your job and you’ve got some pretty good indications that that’s the case, then yeah, you probably should scroll away a little bit.
[00:21:32] Joe: So you’re not saying the cash isn’t important, you’re just saying there’s no difference this year versus
[00:21:35] OG: other years. I mean, you could keep your emergency fund.
[00:21:38] OG: If I gave you the bullet headlines of Q4 2011 and said, based on this, like how do you feel about the beginning parts of 2012? You’d be like, oh crap. Economy’s going to crap. The world’s going to hell in a hand basket. We got all this crazy going on. The politicians are nuts. The stock market’s stupid high.
[00:21:59] OG: It’s at an all time high, you know, probably gonna crash. You’d say that every time. So if you have some personal. Knowledge around something, right? My company is going through massive layoffs at this level and below, and I’m at that level, and I’m a, you know, middle of the road employee. Should I have more cash?
[00:22:18] OG: Yeah, you probably should. Like, if that’s where you are, right? But if it’s like, I feel that the economy is gonna take a crap in the next year, like, I mean, it might, and somebody says something about confirmation bias, it may come true and you’d be like, I knew it. But that doesn’t make it true. That doesn’t make it’s gonna happen.
[00:22:35] OG: And if you do that all the time, the downside of this is that every single time you think that you’ve known something, you’re gonna do the thing that cost you more in the long run. You know, what was it? Uh, Peter Lynch’s favorite thing of, you know, more people lose money preparing for bear markets than actually in bear markets, you know?
[00:22:53] OG: So it’s gonna happen. That’s part of the deal. So I wouldn’t have any extra cash just because. Stock market’s at an all time high and politics are crazy and the world economy is, you know,
[00:23:05] Joe: it’s funny, I saw a headline recently from the late 18 hundreds and somebody said that if you took out the names. It looks, you know, and the, in the
[00:23:12] OG: president’s shot, right.
[00:23:13] OG: You know Right. America to go to war. Right. You know, uprising in the West, it’s like, you’re like, oh crap. So many reason to
[00:23:20] Joe: worry. Right. The only difference was there were no references to cars yet. Jesse, let’s have yours. What’s a good lesson from 2025 that could help us with a better 2026?
[00:23:30] Jesse: Yeah, so the one that I put down that’s not AI related, I, how about, let’s talk about the tariff tantrum.
[00:23:36] Jesse: ’cause I think there it is and, and maybe it’s, it’s going back to, to og and one of the big lessons coming out of it was diversification. But I just thought to myself, especially kind of living through it, hearing stories from stackers and, and clients and stuff like that, it was such an interesting time.
[00:23:51] Jesse: Uh, it, you know, such a sharp decline over a few weeks and the narrative out there was so bad. And then, uh, such a sharp rally. And really the rally has more or less continued up until this recording. Last, the last couple weeks or something like that. But it was just what a, a perfect little microcosm of some of the tribulations that long-term investors have to suffer through in order to eventually get that reward that they’re all seeking.
[00:24:16] Joe: And just Jesse, for Ars Deckers that didn’t pay attention to the stock market Yeah. That closely for the
[00:24:21] OG: 11 people who didn’t know. Yeah. It
[00:24:22] Joe: went down very, very quickly. Yeah. And everybody said it was gonna be the end of the world, and this is it. The game is up. The rest of the year’s gonna suck.
[00:24:30] Jesse: Yeah.
[00:24:30] Joe: And how long did it take it before it started rebounding?
[00:24:33] Joe: Two and a half weeks. I
[00:24:34] Jesse: mean, for what it’s worth, from the top in mid-February to the very bottom in April, it was something like six weeks and it was almost a 20% drop. Sure to recover. It took about another six weeks, maybe eight weeks to recover back to a new all time high. But then if you zoom in even further, right around the moment when President Trump made his tariff announcement, that was something like, you know, a a 10% drop, 12% drop in two days, something like that.
[00:25:01] Jesse: And we had a couple days in there, if you remember, that were like an 8% down day and then a 7% up day. Right? So it was super volatile, right? Don’t, don’t get me wrong, but um, at the same time, I I, I wasn’t invested myself. You, you guys were, and you have memories. You have memories of bear markets that lasted more than a year, right?
[00:25:19] Jesse: And, and that’s, it’s just interesting that like nowadays maybe we’re all dopamine up so much that six weeks of, uh, negative stock performance really hits us. Whereas I think we ought to remind ourselves that it could last much longer in the future.
[00:25:33] Joe: Is that like the third old guy reference there, Jesse?
[00:25:35] Jesse: Um, how might have been the fourth? Your memory might be, uh, failing you.
[00:25:41] Joe: You tee it up for him. Joe Dude’s a legend. Just, uh, what strikes me, Paula, is if you did nothing, let’s say you’re saving to your 401k and you’re dollar cost averaging into your exchange trade funds for mutual funds, you did nothing.
[00:25:55] Joe: You actually made money on this deal. ’cause you just kept automatically putting money in. You actually made money while other people were panicking.
[00:26:01] Paula: Exactly. And that is a story that repeats over and over and over. Right? We could have said the same thing five years ago, 10 years ago, 15 years ago. Dollar cost averaging and not paying attention to the headlines is the strategy that over time has proven more times than not to work.
[00:26:19] Paula: Uh, as compared to market timing. I think it’s counterintuitive because in almost any other field. Effort tends to be commensurate with reward in athletics or in pursuing a, any, anything advancing
[00:26:35] Joe: in business.
[00:26:36] Paula: Yeah. Throwing a business, learning how to play chess, cooking, learning how to cook in almost anything else.
[00:26:42] Paula: Effort, reward, go in lockstep. And investing is one of those extremely rare fields where for the average investor, the average, uh, retail investor, that simply isn’t the case
[00:26:55] Joe: there. There’s two ways to look at this og, and I’m wondering which one you ascribe to. Number one is just don’t care. Don’t know, keep investing.
[00:27:03] Joe: Or number two is follow it closely so you can see the machinery running, but have the perseverance to not do anything. Which one’s better knowing and not moving, or just don’t pay any attention?
[00:27:18] OG: I think that. For 99% of the people, the battle that you don’t have to fight is the best battle. And using Jesse’s example of the tariffs, if you looked at your March 31 statement from your custodian, and then you looked at, nevermind your April one or May one, but then quarter June, one quarter, yeah.
[00:27:43] OG: Once a quarter, you would look at that and go, huh, okay, good quarter. That’s what that, that’s what your reaction would’ve been. You would’ve been like, huh, okay. Yeah, yeah. Cool. It would’ve been so blase if you looked at your statement on March 31, and then April 30th, you would’ve went, eh, kind of a crappy month.
[00:28:03] OG: You know, not the end of the world, but well, whatever. And I think that for most people, the default action is to try to do something with their money. I mean, you just have to look at every single solitary headline in all of America. All the time says the same thing in just different words. It says, how do I react to blah, blah, blah, blah, blah.
[00:28:25] OG: Oh, there’s tariffs. How do I react to tariffs? Oh, there are no tariffs. How do I react to, nor there are no tariffs. There is a peace deal in such and such a place. How do I react to it? Oh, the dollar is down in value. How do I react to it? Oh, gold is up. How do I react to it? Bitcoin has gone down 30% in three months.
[00:28:39] OG: How do I react to it? Everything is, how do I have a reaction to this thing, which is the least productive thing that you can do, which is what Paula was saying. You can’t get better at this by doing more of it. You get better at it by like literally going into a coma and having your dollar cost average work.
[00:28:56] OG: So for most people, not having to fight the demon of like every single day trying to, it’s like the addict, right? When I quit chewing tobacco, I didn’t quit chewing for the rest of my life. I quit going into gas stations because that’s where I bought it. And I was just like, if I just don’t go inside a gas station, I’m gonna eliminate 99% of the chances.
[00:29:18] OG: For the longest time, I never walked into a gas station. Now it doesn’t cross my mind. I don’t, I don’t even see it. Where do you get your beam
[00:29:24] Doug: jerky?
[00:29:25] OG: I know taking away the opportunity for you to have the emotion and doing the thing, like having to fight the battle. Don’t be an alcoholic and go to the bar every Friday night with your buddies.
[00:29:36] OG: Don’t fight the battle. Like, why would you wanna do that? Just be like, I’m, I’m, I’m gonna sit at home. And if you say, well, I’m the type of guy that would never change my investment thesis. If you get hit in the head so many times, you’re gonna frigging change it. You’re gonna do something. Well, maybe I’ll just do a little bit of Nvidia.
[00:29:53] Joe: It was always when I was a planner, my clients that told me, I never panic. The ones who were adamant that I never panic. Yeah. I always laugh when
[00:30:00] OG: people say that.
[00:30:01] Joe: Always the first ones to call me oog, they were always the first ones.
[00:30:04] OG: It cracks me up. So when I go, then you’re, you’re like, I panic. Like I don’t want, I don’t like, I’ve been doing this for almost 30 frigging years.
[00:30:12] OG: Every time it goes down 20%. You know what I think to myself, God dang it, man, I’m so tired of this. It’s so, so soul crushing. You know? I have the same emotions as everybody else. Just a bigger scale of ’em, you know, bigger responsibility maybe. And it’s like, just don’t put yourself in the thing. Like, look at your money once a year.
[00:30:29] OG: I guarantee if you measure backward in that way, you’re gonna be way, way, way, even in 2022. If you’re an investor and you is down 20% and your dollar cost average, you put your money in, da da da da da, like you normally do. Just by doing that, you would’ve had a better experience in 2022 than if you knew every single day what was happening.
[00:30:47] Joe: First thing a diet coach tells you, just get all that crap outta your house. You know, get all the stuff. Yeah. Don’t leave it in
[00:30:52] OG: the fridge and go, I just won’t eat it.
[00:30:53] Joe: Yeah, you
[00:30:54] OG: will eat it.
[00:30:55] Joe: Like putting stacks of donuts around Doug’s house and tell ’em not to eat any,
[00:30:58] OG: like that’s the marshmallow drill from kindergarten.
[00:31:01] OG: Not gonna go
[00:31:02] Joe: well, can’t wait. By the way to hear your second ones, we’re gonna have everyone have one more in the second half of our lessons from 2025. But at that way point all year long, we had this wonderful competition won this year by the Jesse Kramer, who only, uh, Jesse, how many times did you have to cheat and get it like right on to make sure that you won?
[00:31:22] Jesse: Uh, five or six. Five or six, five and a half, I think, I think the half point Chatbots. Did you use the coalition Victory Half point? There was one as well. The,
[00:31:31] Joe: the Coalition Victory Coalition, first half point in Stacking Benjamin’s history. We are gonna do something different today though, stackers, because of the fact that that competition’s over, we can’t not have a competition.
[00:31:43] Joe: So for our friends hanging out with us as we record this. You’re gonna wanna pay attention to Doug, because we’re gonna do some audience participation on this one. Doug, what do we got for today’s episode?
[00:32:00] Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and right now we’re thinking about two things, the holidays and more money. So let’s combine both with this simple clip from a film you’ve probably seen before called National Lampoon’s Christmas Vacation. And if you are one of the stackers hanging out with us on the YouTube live, while we record this in the chat, we want you to write down which round table contributor you think will get the answer right.
[00:32:31] Doug: And if a stacker correctly predicts the name of a round table contributor, who gets today’s trivia answer, correct? Well, Joe, tell ’em what they’ll win. Well, Bob,
[00:32:44] OG: nope. You can’t do. Well, Doug, that’s for Doug to throw his voice only.
[00:32:48] Joe: Sorry. All right. Well, Doug, I have a stack of books that I’ve used to get ready for some of our amazing interviews, like The Incredible Hannah Cole’s great book, Texas for Human Sitting right here.
[00:33:01] Joe: A lot of pages I don’t have, and on the limited sized house, so I need to move these, so I barely have, have scratched it. So it’s, it’s all for you. We’ve got about 50 books on a list and you can take ’em and I don’t care. Regift ’em, give ’em to people you know that are gonna love this stuff. Tell everybody
[00:33:19] OG: it’s a brand new book.
[00:33:20] OG: And you were thinking of them.
[00:33:21] Joe: Yeah, exactly. Regift it like we’re about to
[00:33:23] Doug: do.
[00:33:23] Joe: It’s a, it’s a
[00:33:25] Doug: g, it’s a gently used book, which I know you’re all excited about stackers. So remember, you’re not writing the answer to the trivia in the chat for the thousandth time. No. You are writing the name of the contributor you think will get it right.
[00:33:41] Doug: Will you be done? Brave enough to pick Paula. Paula, have you even seen this movie?
[00:33:48] Paula: I will neither confirm nor deny.
[00:33:50] Joe: Oh, come on. Have you seen this movie?
[00:33:52] Paula: Will not. I don’t know.
[00:33:53] Joe: Margot,
[00:33:54] Paula: I plead the fifth.
[00:33:56] Doug: Alright. Will, will you pick Mr. Holiday? Cheer himself, og, or will you pick Harry Longwood? AKA, Jesse Kramer.
[00:34:06] Doug: You get one pick if you’re hanging out with us live. So pick while we play the clip. Roll it Joe.
[00:34:13] bit: I’m gonna have a wonderful Christmas.
[00:34:17] bit: I have a delivery for Clark w Gman. Uh, I was supposed to deliver it yesterday, but it fell between the seats and I didn’t see it. I’m sorry.
[00:34:33] bit: Merry Christmas. All right. Christmas.
[00:34:40] bit: I can’t believe it. What is it? A letter confirming your reservation at the nuthouse. It’s from my company. Your bonus. My bonus. Oh,
[00:34:56] bit: open it Clark. Open it. Yeah. I hope it’s a porch Clark that you do, Eddie. Oh, I was afraid. Are you gonna ball all over it or are you gonna open it? Oh, I just, I’m just gonna wait till Lamar to tell you all this, but what the heck with this bonus check I’m putting in a swimming pool.
[00:35:26] bit: That’s it. That’s the big one.
[00:35:34] bit: I am sorry if I’ve been a little short with everyone lately. It’s, I’ve been waiting for this bonus to make sure the pool goes in as soon as the ground falls. I had to lay out the money in advance and until this little miracle arrived, I didn’t have enough in my account to cover the check. I wrote. Tear this broke in.
[00:35:50] bit: Dad. Yeah. Drum roll.
[00:36:02] bit: There’s enough leftover. I’m gonna fly you all down here to help us dedicate it.
[00:36:10] bit: I can’t swim Clark. I know that. Eddie.
[00:36:21] bit: Hey.
[00:36:26] bit: Oh hey.
[00:36:29] Jesse: Clark, what’s wrong, honey?
[00:36:33] bit: It’s bigger than you expected.
[00:36:39] Doug: So is the bonus more than Clark originally thought? Today’s question, what is Clark’s bonus specifically? I’ll be back right after I find out from Joe’s mom what this year’s bonus is for helping Frost the snowman cookies.
[00:36:58] Joe: Alright, Paula, you’re going to be playing for a contributor. Which contributor would you like to play for? That said they wanna be on team Paula.
[00:37:08] Paula: I would like to, uh, first make a statement and then make a request.
[00:37:12] Joe: Okay.
[00:37:13] Paula: I would like to make the statement, as you all have seen that my hands have been in the frame the whole time, um, as you have been watching on YouTube.
[00:37:23] Paula: You’ll notice, and this is very intentional, hands up in frame, whole time that played. I just wanna make a note of that. All right.
[00:37:32] OG: Before I pick the person I was writing my card,
[00:37:37] Paula: this,
[00:37:37] Joe: this gets better for everybody who said Paula ahead of time, they’re like, oh, crap.
[00:37:42] Paula: And with that statement made, I would like to make a request because I am notoriously the dark horse candidate here.
[00:37:49] Paula: You know, the long shot. But, but there are no improved odds. And so my request is there, the two people who against all odds, have both said that they wanna be team Paula. Uh, Carlos,
[00:38:01] Joe: we did have two that that picked Paula, no matter what, what’s going on here?
[00:38:05] Paula: Yes, Carlos Espinoza and Daniel Mayen.
[00:38:10] Joe: All right, well, you know what?
[00:38:13] Joe: Because these people are Cousin Eddie in this kid. I can’t swim Clark. I know. May my favorite line of that little clip. Okay, we’ll do it for you, but we’re not doing it for the other two guys. Og, who are you going with? Out of all the people said og.
[00:38:31] OG: Uh, bu
[00:38:35] OG: I’m gonna go Patrice.
[00:38:36] Joe: Patrice is Team OG Patrice. Congratulations. Patrice and, uh, Jesse.
[00:38:44] Jesse: Yeah, it’s a tough pick. Uh, a lot of choices as I scroll through. A lot of choices gonna go with user 5, 5, 7, 1 7 though. That’s they’re, they’re calling my name.
[00:38:59] Joe: User 5, 5 7
[00:39:02] Jesse: speaking your language. They, they are, they are.
[00:39:05] Joe: It’s amazing because user five five, uh, one seven does not know that that was your parents’ first choice for your name when you were born, correct?
[00:39:14] Jesse: Correct. The dog was named Harold and I was 5 5, 7 1 7 for a little bit.
[00:39:20] Joe: It was, it was pretty wild. All right. Everybody has written their guess. Doug, what is.
[00:39:28] Joe: The answer to today’s question,
[00:39:34] Doug: Hey there, stackers. I’m Cookie Froster, but never frosting Eater Joe’s mom’s neighbor, Doug. Earlier we heard a clip from Christmas vacation featuring Clark Griswold played, of course, by Chevy Chase receiving his year end bonus. But what did he get as a bonus? Was it enough for the swimming pool? Was it enough to fly his whole family out to dedicate the pool?
[00:39:57] Doug: Well, let’s listen smaller.
[00:40:04] bit: What is it? It’s, it’s a one year membership in the Jelly of the Month Club. Oh, good Clark. That’s the gift that keeps on giving the whole year that it is Edward. That it is Edward. It’s
[00:40:20] Joe: the Jelly of the Month Club, Doug. Which means I think we have to see what our contributor said. Let’s start off with, start off with Jesse.
[00:40:31] Joe: Jesse, you said
[00:40:33] Jesse: I, uh, I wrote down $15,000. 15. Have you
[00:40:39] Joe: never seen Chris’s vacation?
[00:40:41] Jesse: No. God no. He
[00:40:43] Joe: hasn’t
[00:40:43] Jesse: ever. I was born, uh, I was born after the year 1900. I haven’t seen it. I’m sorry,
[00:40:49] OG: Jesse. I know you say that with a lot of contempt in your heart. However, I strongly encourage you to watch it with a full attempt to all the dialogue I’ve heard.
[00:41:01] OG: It’s, I’ve heard I’m a, I’m a dummy for not having seen it. Just bang, bang, bang. It’s like arrested development. Yes. In terms of, it’s like one-liners that just keep, you can’t keep up with it. That’s really, maybe this Christmas will be the, the Christmas. I wanna hear Paula’s well. Did you think more or less than 15,000?
[00:41:16] OG: Paula?
[00:41:16] Joe: Well, we’ll see. We’ll see. Paula’s holding her, holding hers up. I can’t wait to see the big I
[00:41:22] Paula: I would like to make a note that this notebook has also been in frame since before we played the answer. So everything is fully in frame.
[00:41:31] Joe: It’s not looking good. It is not looking good.
[00:41:35] OG: All right, og. It’s a one year membership to the Jelly of the Month Club Clark.
[00:41:39] OG: That’s the gift that keeps on giving the whole year. This
[00:41:42] Doug: is absolutely OGs favorite movie as he’s quoting
[00:41:46] OG: the movie. It is a hundred percent. We’ve, I don’t think we’ve only watched it probably about twice. Well, as we’re recording this twice this year, but we will watch it no less than a hundred times between now and Christmas.
[00:41:56] Joe: It is so fun. Every year we watch this movie. All right. And uh, Paula, you’re, you’re disappointing two people here, Paula, uh, turn it around. Let’s go.
[00:42:07] Paula: It’s the Jelly of the Month Club. What?
[00:42:12] Paula: What? How did you get that? Paula? Oh, mg. I will never reveal my secrets. What? This is the one movie that she’s watched. I wouldn’t go that far. She memorized it.
[00:42:26] OG: I wouldn’t go.
[00:42:26] Paula: Paula, have you seen this movie? Thank you. Thank you to those of you who took, uh, who took the wild card bet.
[00:42:33] Doug: So that means user 5 5 7 1 7 got totally screwed on this deal.
[00:42:39] Doug: Totally did. But og, who was playing for Patricia Arquette? Patricia gets to pick some books, right? It’s Patrice. Yes. Patrice. Yo, Patrice, uh, write me and close. Put on your reading
[00:42:49] OG: goggles your Spectacles.
[00:42:51] Doug: And Paula was playing for Carlos Santana and Daniel Boone. They both,
[00:42:57] Joe: they both get to pick books, right?
[00:42:58] Joe: Patrice, Daniel, and Carlos. Uh, write me Joe at Stacking Benjamins dot com and just say hey, and I will send you the list. And if you’re able to do it today, because of the day that we’re recording, I’ll see if I can get about tomorrow before I go on a little, little trip for the next couple days. But congratulations, Paula.
[00:43:19] Joe: Your knowledge of your knowledge of pop trivia is pretty incredible.
[00:43:22] OG: Paula has a shirt that says, I don’t know, Margot. No, she doesn’t get that part of the joke.
[00:43:31] Joe: Nope. Of the movie. I guess not. I not that much pup trivia.
[00:43:34] Paula: I’m pacing myself. I’m pacing myself here.
[00:43:36] Joe: All right. Let’s deflect, let’s go in reverse order.
[00:43:38] Joe: Jesse, what’s your second, uh, lesson from 2025 that we can learn from? Uh, which one do I wanna pick? Um,
[00:43:47] Jesse: okay. Uh, financial planning, financial plans need to be dynamic and one kind of big story, but maybe kind of small story, or at least it doesn’t affect everybody was just the way this, uh, big beautiful bill came to be.
[00:44:00] Jesse: That changes to some tax rules, a CA healthcare premiums being a big one that I think maybe some stackers out there are dealing with. In fact, uh, one stacker Paul, who, who we know and, and I met for the first time at FinCon this year, wrote to me and kind of explained the way that based on his income in his kind of early retirement years, how much his a CA premiums would be changing due to the big beautiful bill.
[00:44:22] Jesse: So I just think there’s a really interesting lesson there about. You know, your financial plan. You, you might sit here today or you might sit there on day one of retirement and think, you know, the way that the next few years, decades are gonna go for you. But, uh, it’s a dynamic thing and sometimes that change is triggered by, uh, government policy.
[00:44:41] Joe: Yeah. It’s funny, OJI it strikes me in an earlier episode this quarter we talked about how, uh, kind of funny it is whenever the government says this one’s permanent.
[00:44:49] OG: I love it. I love it when people say that. It makes me smile ’cause I know I have some job security.
[00:44:56] Joe: And a hundred percent is how, how do you deal with that?
[00:44:59] Joe: We talked earlier about the emergency fund. People now are getting, you know, a government agencies are saying that we’re gonna see most probably premium increases on your health insurance for 2026. How do you not,
[00:45:11] OG: not most probably are. By this time, everybody will have already enrolled, so hopefully, uh, you’ve already seen it.
[00:45:19] OG: I think the biggest thing, by the way, I mean a CA doesn’t work like this, but in other areas, I think the biggest thing is ask for a better deal. I was talking to my kids about this. My son was recounting the car purchase story when we bought his car, and he’s like, I just don’t understand why with cars, you know, you go to the grocery store and it’s some milks, five bucks or whatever.
[00:45:40] OG: You don’t go up to the cash registers to go, eh, I thinking four. You know, there’s, you just scan it and you pay. He goes, but you, he’s like, you sit down with this guy, the sticker says, you know, 20,000, and you go, I’m not willing to pay over 17. That guy goes, ah, I can’t do, but I can do 19. Yeah. I can’t do, I can do 18, I can do 18 five.
[00:45:57] OG: He’s like, why don’t you, why don’t I just say 18 five and that’s what you’re gonna pay, and that’d be the thing. He’s like, I don’t understand that. I said, well, the funny thing is, is that everything is like that. If you just ask. Most things. I shouldn’t say everything, that’s a broad generalization, but we got our health insurance quote from our agent and the only thing I said, he said, do you have any questions?
[00:46:15] OG: And I said, I have one question. Is this the best price? He goes, yeah, it’s a big increase. Let me go back and ask. And two days later he came back and he goes, we lowered it, you know, it was a 20% increase. We got it to a 15% increase. Still an increase. It still sucks. You know,
[00:46:30] Joe: it’s still that 5%. That’s not nothing, but
[00:46:32] OG: it’s, but you know, it’s compounded, right?
[00:46:34] OG: Yeah. It’s like, it’s like your house, you know, and each your house appraisal and, and you say The first time when I get my house appraisal, I’m not gonna fight it because it’s in the ballpark, but it’s off by two or 3%. Well that off by two or 3% for a 20 year time period. It’s gonna compound into lots of money that you’re gonna pay in taxes.
[00:46:50] OG: That you could have just said, I think the number’s a little lower. Just ask. But the question was, was more about like, how do you adjust for this in your plan? And the reality is, just like Jesse said here, financial planning is we’re gonna point the boat in the right direction and we’re gonna start row.
[00:47:06] OG: Then we’re gonna make changes. So the plan that you make today is not gonna be the same plan that you have in five years from now. It’s probably not even the same plan that you have in two years from now because, you know, life happens and it comes in different ways, comes in different ways. Like, hey, surprise, you’re having a baby to, hey, surprise, you’re losing your job to, hey, surprise, you got promoted and you’re moving across the country, you know, or you’re moving back home ’cause you gotta go take care of your parents.
[00:47:31] OG: There’s all sorts of different things that can pop up in your life and you know, the best you can do is just take the information that you have, make a plan for it, and row the boat in that direction. And then reevaluate.
[00:47:42] Joe: It’s funny, Paula, I really like what OG said earlier in the first half of today’s show about the stock market and just, you know what, don’t pay attention, right?
[00:47:49] Joe: Just don’t pay attention at all. But if you weren’t paying attention at all to the fact that price increases might have changed with your health insurance going in 2026, like that could, that could blindside you big time. So is there a line there where, okay, I listen to the news, but when they turn on the stock market news, I shut it off.
[00:48:07] Paula: No, I mean, I wouldn’t think so. Even the news about health insurance premiums increasing, that didn’t break until very shortly before open enrollment season began. Even if you were carefully watching the news and you heard that the moment that the story broke, that still would not have given you a a good adequate amount of time to.
[00:48:28] Paula: Save up the, the cost differential. So I don’t think the answer there is necessarily paying attention to the news. I think it’s having a margin of error within your budget so that you can account for the unexpected. And sometimes the unexpected comes in the form of car repairs or veterinary bills, but sometimes the unexpected comes in the form of just higher premiums.
[00:48:49] Paula: Right now the discussion is health insurance, but um, we’ve seen this with car insurance. We’ve seen this with homeowners insurance, flood insurance, particularly for people who live in disaster prone areas. So, you know, we’ve seen the same story play out in, in many different forms.
[00:49:05] Joe: I think it’s just another reminder.
[00:49:07] Joe: The big thing I always hear from people is, I hate change. I can’t stand change. And change is the only constant. There will always be change. So learning to get comfortable with change, I think is a really important lesson from 2025. Polo, let’s stick with you. What was on your list?
[00:49:24] Paula: The story of the housing market this year was really interesting because there are a couple of lessons from it.
[00:49:30] Paula: One is that, uh, this is actually in some ways the opposite of the last lesson. Change can happen very slowly. I think people were hoping for a bigger interest rate declines this year, and we went for the bulk of the year without any interest rate decline. You know, it didn’t start, the Fed didn’t start lowering rates until relatively late in the year.
[00:49:50] Paula: And even when they did start lowering rates, I mean, that didn’t necessarily move the 10 year treasury, which means that mortgage rates didn’t move in quite the way that people were hoping. You know, even after the Fed funds rate dropped twice. And so I think that, you know, the, the, the counter lesson is that change can sometimes happen very slowly, and we saw that in mortgage rates this year.
[00:50:12] Joe: Well, and I think that the key here, Jesse, is that people were hoping for that to change and hope is not a plan.
[00:50:18] Jesse: Yeah, I mean, it’s a tough situation. Hopium, hopium, opium, I’m sure they’re all hopped up on Hopium. I mean, I consider myself one of them where I really would like interest rates to go down so I can refinance.
[00:50:30] Jesse: But we made the housing purchase upfront knowing that if interest rates never go down, we would still be fine. Right? And I think that’s one of those, like, you kind of have a little barbell strategy to these financial decisions, which is in the worst case scenario, you’re still gonna be okay. And in the best case scenarios, you’re gonna be great.
[00:50:48] Jesse: Or at least, you know, at least that’s one way of approaching, um, you know, building in conservatism into your financial plan, into your financial decisions. I do think conservatism sometimes can go way too far in the other direction, but all else being equal. Having a little bit of conservatism in there really helps.
[00:51:03] Jesse: But yeah, as far as what Paula’s comments were, I think that some people learned some interesting lessons this year about the different relationships along the interest rate curve. And that just because the short end of the curve changes doesn’t necessarily mean that your mortgage rate or that mortgage rates across the country are going to change.
[00:51:21] Joe: Can we talk for a second, guys, about this new product now? The idea of the 50 year mortgage og,
[00:51:28] OG: what would you like to talk about?
[00:51:31] Joe: Well, I mean, this was presented in 2025. What are your thoughts?
[00:51:35] OG: Um, it is an awful, awful idea. That is my thought. Which one of you guys posted something or sent me a picture of something about the grandkids having to co-sign for your housing.
[00:51:48] OG: Your housing? ’cause they’re gonna, they’re gonna inherit the loan. Like this is beyond stupid and I get. I, I think this has a lot to do with, and this is gonna be like old man yelling at cloud for a moment, you know? But I think this has a, a little bit to do with like, FOMO stuff. And for some reason everybody, everybody seems to compare their beginning to everybody else’s middles, you know?
[00:52:15] OG: And it’s like, and I, and, and I’ve seen it for two generations. So I’ve, I saw it when I was in my twenties and thirties and I see it when the next generation’s in their twenties and thirties. And I hear it just, you know, in the dialogue. And I’ll be interested to see when my kids get to that age to see what happens.
[00:52:32] OG: And, and I’m not saying that it’s not different ’cause I understand that it is, but I remember when I was like in my twenties and thirties going like, I’m never gonna be able to buy a house. These housing prices are crazy. Like, what is going on? Like, stupid boomers have all the property and they’re not selling it.
[00:52:46] OG: And like, you know what I mean? Like, that was going on when I was in my twenties and now it’s the same thing. I’ll be 48 this year, sometime between now and the end of the year. You guys don’t know when, but it’s happening and you hear the same stuff. It’s like, you know, all the old people have screwed up the housing market and you know, you guys got all the cheap money and all that sort of stuff.
[00:53:08] OG: I’ll never be able to buy a house. It’s like, well, ’cause you’re 28 years old, you don’t get to have the $2 million big giant house at 28, bro. Like, I’ve worked my ass off for 30 years to be here. But you see that and I th I don’t know if this’s a social media have having a lot to do with it or like why that is.
[00:53:25] OG: And I know that there’s other things and so I’m gonna get a bunch of hate mail. People are like, you don’t understand what it’s like to be like, you know, whatever. I get it. To some degree. Stop comparing the beginning part of your life to somebody else who’s like 50 and has been saving money their whole life and you know, and investing and that sort of thing.
[00:53:41] OG: It’s like with that attitude, you’ll never have 5 million bucks in your investment account either. You don’t start there, you start with zero and you have to do the thing for 25 years. You know. Oh yeah. Somebody said a hundred thousand. Yes. Right.
[00:53:55] Joe: Yeah. But B Wayne says, uh, people were freaking when housing prices hit a hundred thousand dollars back in 1990.
[00:54:01] OG: And I’m not saying that inflation hasn’t had a, a, a negative effect on this or interest rates. Sure. That there’s some areas like the Bay Area area where it’s just crazy, a freaking home run by the fact that I got to refinancing COVID for two and a half percent. But I, and this is on the show, I talked about this then I didn’t do 25, 2 and a half percent for 30 years.
[00:54:19] OG: I did, I told everybody, take the two and a half for 15 years, because that’s a better deal in the long run. Like you get the rate and the term and you can knock this stuff out. And so yeah, I’m sitting here seven years into it, or five years into it, having paid aggressively with seven years to go on my mortgage.
[00:54:35] OG: Well, we got you in the spotlight, og. Well, you’ve got the last
[00:54:37] Joe: one.
[00:54:39] Jesse: Oh, Jesse’s got some. I’m, I’m trying to be a better, uh, what’s the improv? Oh, we, where you say, oh, haven’t done Jesse’s yet.
[00:54:43] Joe: What am I talking about? Sorry, man. Where you say
[00:54:44] Jesse: yes and where it’s like. OG on the one hand. I see what you’re saying.
[00:54:49] Jesse: Where I think there is some sort of, whether it’s social media causing all these comparisons and accelerating people’s timelines to get to certain places in life. And when I look at the Case, Schiller Home Price Index or the all transactions House price index, all of which are indexed for inflation, they are also at all time highs.
[00:55:10] OG: Yeah. Which
[00:55:10] Jesse: I think, you know. Right. So it’s it’s it’s both. It’s both. It’s a yes. And for, for me,
[00:55:14] OG: yeah.
[00:55:15] Jesse: I think it is for all of us. Yeah.
[00:55:18] OG: Should see the prices that, nevermind. Go for it. All right. Do you got the Say it,
[00:55:22] Joe: do you got the last one here, og?
[00:55:24] OG: Yeah, I got one. Uh, this one’s a little touchy feely ’cause you guys were talking about like what happened in 2025 and you said personal.
[00:55:30] OG: So I was thinking about the stuff that’s happened to me personally. My oldest graduated high school in May, and for the better part of about 10 day period, we had. Both sets of his grandparents here. We had aunts and uncles, we had cousins. And not everybody stayed at the house. Most people were staying at hotels.
[00:55:47] OG: In fact, I think everybody did mostly. ’cause I didn’t wanna argue about like who was sleeping on the floor versus the, you know, mattress versus the blow up bed versus why do I have to sleep on the stairs again? It’s like, get a hotel. But I think about that quite a bit in the context of a few things.
[00:56:02] OG: Number one, if you have kids and you’re like in the middle of the suck, where it’s like all the chaos is going on, and whether it’s diapers or middle school where there’s, you know, drama or it’s high school and there, there’s never ending activities going on. This ends and it ends with just an explosive ending.
[00:56:25] OG: It’s like busy, busy, busy, busy, busy, stop. There is no ramp down. It like it stops and then your kid goes away. So even though it kind of, you feel like it might suck a little bit, like embrace the suck because like this stuff ends and it ends viciously. And then the second thing was I really love the fact that we got to spend so much time with our, some nieces and nephews, our nieces and nephews that, you know, we’re not, we’re not, we don’t live close to, uh, we had a bunch of people in the house.
[00:56:52] OG: We had parties every day. You know, it was beautiful weather. The, the most exciting thing for us was our nieces and nephews. Most of them showed up not knowing how to swim and left swimming because they just spent all day, every day in the pool. And you can’t help but learn how to at least float, you know, when you’re, you know, not, they’re not Olympic class athletes, but they managed to like not die while, while they were in our care.
[00:57:15] OG: And, um, that was a little bit of a, an accomplishment, but again, more about like, just family time and like. You know, those times come by few and far between. And I know a lot of times people get stressed around the holidays like, oh my God, oh, grandma and grandpa are coming to town. It’s chaos. Or all the cousins are coming, or I don’t feel like doing this stuff.
[00:57:33] OG: Like tomorrow’s not promised everybody and there is nothing better than hanging out with people that you care most about or that care most about you. And if you could pull that off, if you can spend a day, or you could spend two days this holiday season, you know, with those people around you, like that’s the best thing in the universe.
[00:57:51] OG: So I get it. The travel sucks. You know, airplanes are awful. The weather delays, the American Airlines can kiss my butt. Rental cars screwed you. All of that sucks. But hanging out with people that you care about is the most important thing. And if you can do that one day or a day and a half more or something, super awesome.
[00:58:09] OG: So I look back on this year and I see that as a big transition for us, or at least a third of a transition for us. I love this time that I got to spend with my oldest and now he’s off to college and when he gets home, that’s cool, but I also like the time that everybody was here collectively. So anyways, I think that’s
[00:58:25] Joe: a great place to leave it.
[00:58:27] Joe: I think a, a big lesson there is that I’ve learned over time is it’s, um, saying I’ll be happy when these other conditions happen. That’s right, yeah. Is a mistake. Like I always show up me. And, uh, so em embrace where you are. Love that. I think it’s a great ending point for this end of the year round table episode.
[00:58:47] Joe: Og, let’s stick with you. It’s your birthday ish weekend. So, uh, any big plans.
[00:58:53] OG: Absolutely. Of course. It’s getting crazy. The OG house, didn’t you get your ticket? I mean we had, you got DJs and fog machines and all sort of stuff. You had to, apparently,
[00:59:02] Joe: Doug, I’m gonna use OGs line. Apparently we weren’t
[00:59:04] Doug: invited.
[00:59:05] Doug: Yeah. What? Never again this year. Weird. You know why? ’cause he likes to spend his time with people that he cares about and that care about him. So we don’t make that list.
[00:59:14] Joe: Sucks to suck. Doug. Jesse, thank you so much for being on this last time. I, uh, thought it was great. This was a great year. The one and done.
[00:59:21] Joe: It was a one and
[00:59:22] OG: done year.
[00:59:22] Jesse: I had a lot of fun.
[00:59:24] OG: It was a great year out with a bang. Jesse, nice knowing you.
[00:59:29] Joe: I gotta say, Jesse, in all seriousness, it was a fantastic year having you board the team. Thanks for all your contributions this year. What’s going on at the Personal Finance for Long-Term Investors podcast?
[00:59:40] Jesse: Well, the feeling is mutual. Thank you. Thank you all for having me. It’s been, it was a lot of fun. It was a great year. And, uh, while I’m talking about how great your podcast is, what a perfect time to tell you what’s going on at my podcast, right, Joe? No. And if stackers go over to the podcast feed right now, shots fired, they’ll see a yet to be recorded as of this recording.
[01:00:01] Jesse: But I’m looking forward to recording it. Episode, it’s my past, present, future Christmas spirit episode that I stole from either you or Charles Dickon Dickens. I’m not sure which, but, uh, I have a unique thought process in my head for how I’m gonna record it, and I think it’s gonna be a really fun episode.
[01:00:16] Jesse: So, uh, that’s what listeners can go over to and, uh, listen to right now.
[01:00:20] Joe: That’s fantastic. The more the merrier, Jesse.
[01:00:23] Jesse: Ah, it’s a great idea. Good one, good one.
[01:00:26] Joe: Paula Pant, another fantastic year hanging out with you. Thank you so much for giving us the gift of your time and expertise. What’s going on at Afford Anything to run out the year
[01:00:37] Paula: on the Afford Anything podcast earlier in the month, we had some great interviews.
[01:00:41] Paula: We, uh, aired William Vander Blumen talking about working how you’re wired. We aired David Bach. He’s best known for don’t buy lattes. But really we get deep and we get philosophical and it’s a long conversation. And one of my favorites, so all of that aired in early December around, um, the week of Christmas.
[01:00:58] Paula: We aired greatest Hits week, some of our best from the archives. And then coming up soon as we go into New Year’s, we always, every New Year’s do like a retrospective on 2025 and then a look ahead to 2026. And then we also have one tweak a week, which is our annual, how to make tiny tweaks once just a little, little, little thing that you can do one week, you know, 52 tweaks.
[01:01:24] Paula: You can do one small thing every single week. Make that your new re resolution for 2026. These are micro tweaks, but they add up.
[01:01:33] Joe: It’s fabulous. And that is, uh, all coming up and happening at the Afford Anything podcast. Thank you so much stackers for hanging out with us. Uh, our friend James in Boston says, uh, we need fewer OG travel stories this year and, uh, probably more Joe Travel.
[01:01:51] Joe: Yeah, we got Wait, what he got exactly? James. Oh gee.
[01:01:54] OG: Travel stories.
[01:01:56] Joe: James. I think he got the desired reaction. Duh. Fuck.
[01:02:00] OG: Talking about.
[01:02:03] Joe: Alright. Uh, we gotta go because I gotta go travel somewhere, which I never do.
[01:02:07] OG: Yes, Joe is busy, busy, busy.
[01:02:10] Joe: Doug, you gotta from here, man. What should we have learned
[01:02:12] Doug: on today’s show?
[01:02:14] Doug: Well, Joe, first take some advice from og. The evolution of efficiency is a wheel that just won’t stop rolling. Better figure out how not to get run over. Second, as Paula said, life is a funny way of changing very, very slowly. So take a note from Jesse. You might sit and wait for mortgage rates to be lowered or for your TGI Friday stock to go to the moon.
[01:02:40] Doug: And while Hopium is a powerful drug, hope is not a plan. But the big lesson, don’t ask Joe’s mom what her big lesson was in 2025, she said this new thing called Napster is gonna crush the recording industry. Yama, you’re right. Totally nailed that one. Go back to sleep. Thanks to Paula Pan for joining us today.
[01:03:04] Doug: You’ll find Paula’s wisdom on the Afford Anything Podcast wherever you are listening to us. Now you know what? Because it’s Hanukkah, I’ll also give you the gift of a link in our show notes at Stacking Benjamins dot com. Thanks to the Jesse Kramer for hanging out with us today. You’ll find his amazing personal finance for Long-Term Investors podcast, wherever you listen to finer podcasts, eh, what the heck?
[01:03:29] Doug: You talked me into it. I’ll also share that link on our show notes at Stacking Benjamins dot com too. And finally, thanks also to OG for joining us today. Looking for good financial planning. Help head to Stacking Benjamins dot com slash OG for his calendar. This show is the property of SP podcast LLC, copyright 2025, and is created by Joe Saul-Sehy.
[01:03:53] Doug: Joe gets help from a few of our neighborhood friends. You’ll find out about our awesome team at Stacking Benjamins dot com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. Oh yeah. And before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know.
[01:04:15] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s Mom’s neighbor, Duggan. We’ll see you next time back here at the Stacking Benjamin Show.
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