Most people don’t start thinking seriously about retirement until their forties. If that’s you, the good news is you’re not behind. You’re normal. And this week three CFPs, Jackie Cummings Koski, Roger Whitney, and OG break down exactly what to do, in what order, starting right now.
In this episode:
Why panic is the enemy of a good retirement plan, the first place your money should go before anything else, why your savings rate matters more than finding the perfect investment, and the one investing mistake people make when they feel behind.
Biggest takeaways:
Give yourself grace first. This stuff isn’t taught in school. The two years Jackie spent just processing her situation before taking action weren’t wasted. That clarity is what made everything else stick.
Increase your savings rate by 1% every six months. Going from 3% to 13% over five years feels like a non-event the entire time. Automation makes it invisible.
Simple beats clever. Index funds, low cost, diversified, and boring. When you feel behind, the temptation is to swing for the fences. That’s exactly when boring saves you.
Real estate and dividend strategies are tactics. Tactics come after you have a strategy. For a 40-year-old starting from zero, the strategy is build the habit and save more.
Resources mentioned:
Jackie Cummings Koski’s book Fire for Dummies and podcast Catching Up to FI at catchinguptofi.com Roger Whitney’s Retirement Answer Man podcast at rogerwhitney.com
The Stacking Benjamins scorecard: stackingbenjamins.com/scorecard
The Vault: stackingbenjamins.com/vault
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Our Topic: how to start investing for retirement at 40 with no savings
During our conversation, you’ll hear us mention:
- Starting at 40
- Retirement catch-up
- Late starters
- No savings
- Retirement panic
- Grace over guilt
- Knowing your numbers
- Debt assessment
- High-interest debt
- Employer match
- 401(k) contributions
- Savings rate
- Automated increases
- Behavioral compounding
- Financial hope
- Sustainable habits
- Micro adjustments
- Spending awareness
- Income growth
- Big shovel
- Index funds
- Dividend investing
- Capital appreciation
- Risk tolerance
- Market downturns
- Real estate leverage
- Simple investing
- Diversification
- Financial independence
- Action over perfection
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Jackie Cummings Koski
Another thanks to Jackie Cummings Koski for joining our contributors this week! Hear more from Jackie on her and Bill Yount’s show, Catching Up to FI at Catching Up to FI – Podcast – Apple Podcasts.
Check out her hit book F.I.R.E. For Dummies.
Roger Whitney
Another thanks to Roger Whitney for joining our contributors this week! Hear more from Roger on his show, Retirement Answer Man, at Retirement Answer Man – Podcast – Apple Podcasts.
Grab your copy of his book Rock Retirement: A Simple Guide to Help You Take Control and Be More Optimistic About the Future
OG
For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- In what year were bananas first sold in London?
Mentioned in today’s show
Join Us on Monday!
Tune in on Monday when we dive into the topic of geopolitical pressures and we’re going to help you steer your ship through treacherous waters and trying times.
Miss our last show? Check it out here: Most People Retire Differently Than They Planned. Here’s How to Prepare (SB1826).
Written by: Kevin Bailey
Episode transcript
[00:00:00] OG: Is this your place? No, no, no, no, no, no, no. I live with my mom. Oh yeah. You hungry? Hey Ma, can we get some meatloaf? [00:00:15] Doug: Live from the basement of the YouTube headquarters. It’s the Stacking Benjamin Show. [00:00:28] Doug: I’m Joe’s mom’s neighbor, Doug, and let’s set the stage. It’s your 40th birthday party. No retirement savings, no plan. Just a vague memory of buying Dogecoin once and maybe a strong desire not to eat cat food at 75 years old. How would you begin to invest for retirement? We’ll tackle the good, bad, and ugly on today’s show, but that’s not all. [00:00:52] Doug: Halfway through this shindig. We’ll roll out to our contributors another episode in our year long trivia competition. And now a guy who’s gonna help you compete when it comes to setting up a great retirement portfolio. It’s Joe Saw. See? Hi. [00:01:12] Joe: Hey, thanks Doug. We’re super happy that you’re here with us Stackers. Welcome to Friday. And man, we do have a great show today, Doug. So many times people wake up and go, oh wait, I’m supposed to do what? [00:01:25] Doug: There’s this thing that’s been like nagging at me. I can’t remember what it is [00:01:29] Joe: like, in fact, gets funny when we talk about, we talk about, and a lot of people start at 40. [00:01:34] Joe: In fact, one of our guests was a late starter and is done incredibly well. You’ve heard her on the show before. We’re gonna get to her in a second. But let me show you the person who thought that he was about to have a bad day. And, uh, you and I know Doug, it can get worse than what this person said. This is, uh, comedian Brian Reagan. [00:01:54] bit: I think the worst day. That was the day the science project was due. Waking up that morning. That was fun. Huh? Your head had pop off your pillow. Oh no. [00:02:02] bit: Oh no. [00:02:04] bit: That’s due today. [00:02:06] Joe: This is like the adult equivalent, I think, Doug, of that. Oh no. Oh [00:02:10] Doug: no. [00:02:10] Joe: I’m 40 years old. I’ve done nothing. [00:02:12] Doug: It’s the worst feeling in the world. [00:02:13] Joe: Too many people have had that. A guy who helps people make sure they don’t end up on the right foot. Everybody, I think starts on a different foot, but Mr. OG is here across the cart table from me. How are you man? [00:02:25] OG: We make sure people don’t end up on the right foot. We want them. [00:02:27] Joe: Don’t end up on the wrong foot. [00:02:28] Joe: Didn’t I say wrong? Wrong foot? [00:02:29] OG: No. Yeah, you said right foot. [00:02:31] Joe: I hope I, [00:02:32] OG: I mean, I guess left foot’s okay too. If you [00:02:35] Joe: wanna end up on that, if you end up on the left foot, the left foot’s very comfortable in the right shoe. It’s great. It [00:02:39] OG: works for everybody. [00:02:40] Joe: Were you the kid with the science project going, oh no. [00:02:42] Joe: It’s due today. [00:02:45] OG: No, no, I was, I’m a firstborn man. I’m a rule follower. I, uh, I’m a people pleaser. I’m all those things wrapped up. I, [00:02:54] Doug: yeah, you are a people pleaser. We all know that. You [00:02:56] Joe: almost pulled that off almost. [00:02:57] Doug: I was the youngest, so I would wake up that day, have that feeling and say, well, guess I’m sick today. [00:03:04] Doug: And then I would start heating up the forehead, you know, getting my nose all stuffed up to talk to mom. [00:03:11] Joe: Hmm. And a woman who actually, the woman who I referenced earlier who started late is here. She is the cohost of the Catching up to five podcasts. She’s the woman. Behind a great book about the fire movement. [00:03:22] Joe: Fire for Dummies. Jackie Kosky Cummings is here. How are you Jackie? [00:03:26] Jackie: Hello. I am doing great. How are you guys? [00:03:29] Joe: Were you the person with the science project and said, oh God, it’s today. [00:03:33] Jackie: You know what? I wasn’t, but I’m finding myself as an adult. It’s almost tax time. I haven’t even started, so that person today, [00:03:41] Joe: I like how Fire for Dummies is just kind of casually there behind you. [00:03:45] Jackie: Yeah, I need to move that. It’s over a year old now, so it’s a time to like scoot that to the side. [00:03:49] Joe: I don’t think so at all, because those lessons are timeless and we’re gonna talk about some of them today. You are by the way, not just somebody who really appreciates the fire movement and talk about it with your co-host. [00:04:00] Joe: Bill. You’re somebody who actually talks a lot about how you started late. You talked about it on this show. [00:04:05] Jackie: I do. I talk about it all the time because a lot of the fire movement, the way that it started, you had a bunch of 30 year olds and I was 38 when I woke up and got started. So just under 40 and I wanted, and as well as my Kohls, I wanted represent that piece of it because to the general public, anything before 65 is considered early. [00:04:25] Joe: Yeah, it is wild that inside the movement that like what? You’re 40, but to the average person, I bet there’s a lot of people that saw this title of this episode and they’re like, oh good, perfect. I’m getting started right now. [00:04:37] Jackie: That’s right. That’s right. Most people have almost nothing for retirement. You know, you see all the statistics out there and all the research and things like that. [00:04:44] Jackie: So 40, you know, some people will consider that late. I was a little bit younger than 40, but. Most people, that’s when they’re starting to think about retirement. Maybe they have a little something. Maybe not. [00:04:56] Joe: Jackie Forty’s the new 30 now, right? [00:04:58] Jackie: That’s right, baby 40 [00:05:00] Joe: 30, the new 30. And a guy who is hoping that very soon he has his 40th birthday. [00:05:06] Joe: He is the guy behind the retirement Answer man podcast. Our good friend Roger Whitney is back. Roger, you turned 40, what? A year or two? [00:05:14] Roger: Exactly. I’m 59. I had a month and a half period when my wife just turned 60. I’ll just say that on air, and she was two years ahead of me for about a month and a half. It was awesome. [00:05:25] Joe: Because you had an older woman you were married to? [00:05:28] Roger: Yes, by a month and a half, and I was totally like Doug, except I didn’t even go try to explain it to my mom. I didn’t care that [00:05:35] Joe: much. Roger. I don’t, Roger, I don’t know that we’ve ever talked about this. Were you an early starter, a late starter? How did you start your retirement journey? [00:05:45] Roger: Oh, I was a late starter. I was a late starter in, in my twenties. I made way too much money and was way too cocky about my trajectory and spent future earnings, and I took all of my thirties cleaning up my twenties, so I started relatively late from a traditional retirement savings. The difference is I was investing in a business that could really compound my income quickly. [00:06:09] Roger: Oh, and that was what ultimately. Save me, and maybe we’ll talk about building a shovel a little bit in this conversation. [00:06:15] Joe: That is interesting. Yeah. Talking about income streams and how those work together. Well, you can see we’ve set the stage, everybody. I’m gonna give the three of you, Jackie, og and Roger. [00:06:24] Joe: I’m gonna give you like a fictitious person here in just a moment. We’re gonna help that person get retired. Maybe you see yourself in that person if you’re hanging out with us, maybe there’s little pieces of it. So grab wherever you take notes, whatever you take notes with. And we’re gonna dive in in just a moment to this topic. [00:06:40] Joe: But first we got a couple sponsors who make sure that we can do all this live on YouTube, and then on the podcast for absolutely nothing. We’re gonna hear from them as, uh, our friend Paula Pant always says It’s absolutely free and worth every penny. We’re gonna, we’re gonna hear from them and then Roger, Jackie, and OG are gonna help you even if you started late, even if it’s way past 40. [00:07:05] Joe: Get moving. [00:07:15] Joe: I often write, here is where I say, today’s discussion is based on this thing that I read. It was actually just a need that we get questions all the time. Jackie, on your show, you get questions all the time. Roger, on your show, you get questions all the time. Hey, I’m starting late, what do I do? And I’m like, what a perfect panel of people to dive into this topic. [00:07:37] Joe: So let me give you just this person that I made up. This person 40 years old, as I’ve mentioned, wants to retire at age 65. Their income, well, let’s say they’re middle class, maybe they make 75, a hundred thousand dollars, no savings. And let’s do this too, guys. We’re just gonna take the pension today out of the game. [00:07:59] Joe: They have absolutely no pension. All right, Jackie. How does this relate to where you are? Is this a crisis or is this totally fixable? [00:08:09] Jackie: It’s absolutely fixable, but it can feel like it’s not. I think when people finally wake up, let’s say in their forties and they’re like, I have not saved me enough, or I’ve saved nothing, it feels like it is the end. [00:08:23] Jackie: But if you realize that you need to do something different, that could change the whole game. So it definitely fixable. I was close to my forties when I woke up. I had a little something but felt like I didn’t have much of anything, and it’s usually because people don’t know their numbers, and that’s usually a great starting place. [00:08:44] Joe: Just know how far behind you might be. [00:08:46] Jackie: Well, I don’t put it like that. I don’t put it like that, but I guess even before then, it’s a psychological part. You know, give yourself a little grace. The stuff is not taught in schools, and if you didn’t grow up around good role models where you were exposed to financial education, why would you know? [00:09:05] Joe: Yeah. [00:09:06] Jackie: So when you do wake up and your coworkers all starting to talk about it, Hey, I’m five years from retirement, 10 years away from retirement, you’re thinking, oh my gosh. When you just pause for a moment, you start to realize, I know I haven’t been doing everything right. You let that sink in, you give yourself a little grace, and then you start to say. [00:09:23] Jackie: And it, and it could be a while, it could be months for me, it was almost two years before I realized that and I actually started doing something. And you kind of need that time to figure out, okay, what have I been doing wrong? What have I been doing right? And how can I start to fix it? Sometimes they think people kind of rush immediately to give me the best portfolio, right? [00:09:44] Jackie: Gimme the thing that I can get the biggest return. You know? So that’s the natural response. But if you take a moment and kind of digest it all, see where you’re at, that makes all the difference, and then you can start heading in the right direction. [00:09:57] Joe: I wanna chat in a second about this sense of panic that people have, but Roger, Roger, you’re already chatting it up with all our stackers hanging out on YouTube. [00:10:06] Joe: Our friend b Wayne says, after I described the scenario, said totally brutal scenario. You said, not necessarily. This is very common. You see this all the time as well. [00:10:16] Roger: Oh, it’s crazy. It’s totally common. You look at the statistics of 60 year olds and how much they have for retirement. I don’t have the number off the top of my head, but it’s not, not much. [00:10:25] Joe: Mm-hmm. [00:10:25] Roger: And it’s normal. Some of the areas of the scenarios, we don’t know how much debt they have. They likely a normal person would probably have debt as well as what you just described. But you have to start where you start. And I can hear it already in how we’re talking about it, Joe, how we frame it, you know, like, uh, be Wayne. [00:10:44] Roger: Totally brutal scenario. They’re so far behind these framing the way, even the way we frame the problem can really influence how someone might address it. You know, just throw your hands up. Well, well, well, dang it then. I guess I don’t have to worry about it. You know, if you think of the, the Science of Hope, uh, the Science of Hope has three pieces to it. [00:11:05] Roger: You have to see a better future for yourself. You have to be able to identify agency where you can do something to get to that better self. And you have to find different pathways. And I think that’s where someone needs to live when they have this aha moment. Otherwise you’re just gonna put your head in the sand. [00:11:21] Joe: Yeah. Oh, a hundred percent. Well, I might as well do nothing. I’m screwed either way. [00:11:25] Doug: Yeah, I think that’s really common actually. I have a relative who did exactly that. They probably got to late forties, early fifties in this same scenario and thought, you know what? I might as well have fun ’cause I’m gonna work till the day I die. [00:11:36] Doug: And never made an attempt to get any roots or anything growing in their, in a, in a portfolio. So [00:11:43] Joe: yeah, [00:11:43] Doug: I think that’s probably pretty common. [00:11:45] Joe: How many time have those early retirees around us told us the tale of, they tell people that they’ve retired a X Age and, and they hear must be nice. Right, right. [00:11:54] Joe: Must be nice. Jackie, Roger talked about debt. I think I remember when you and I chatted, uh, more deeply and I’ll link to it in our show notes at Stacking Benjamins dot com, our longer conversation about your, your whole journey. I think I remember you had debt, didn’t you at first when you were starting out? [00:12:10] Jackie: I did. I had just a little bit, but it was manageable even though I grew up poor, raised by a single dad with six kids. The one good lesson he did teach us, or that I took away was that debt was bad. So I didn’t have a lot of debt, but I did have student loans and I did have some credit card debt. Luckily, they were manageable. [00:12:30] Jackie: They didn’t hold me behind. But the typical person probably does have a lot of debt, and that’s a piece of the puzzle as well. That’s why I say, you know, you kind of need to pause and kind of look at where you’re at if you got a lot of debt, that’s, [00:12:41] Joe: that’s the numbers you’re talking about? [00:12:42] Jackie: Yeah. Yeah. [00:12:43] Jackie: That’s the numbers, yeah. [00:12:44] Joe: Mm-hmm. [00:12:44] Jackie: All of those numbers, [00:12:46] Joe: oh gee, you know, Roger brought this up earlier. You hear this kind of sense of panic. People have. Even the way I presented it, I might’ve done that a little on purpose, but I think this also clouds the way people invest. If they feel like at 40 I’m behind, they may get into some investments that might not be the right thing. [00:13:05] OG: I think that there’s two, two great crimes in financial planning, and most people focus on the first one, which is what we’re talking about today, which is undersaving, and it causes a whole series of dominoes to fall. And, and one of those is that sensation of being behind and then that the, the next thing of like, I need to do something to catch up. [00:13:25] OG: That’s the next phrase that happens, and the right way to catch up is by saving money and investing it appropriately and living within your means. And, uh, stop digging a hole, you know, in credit card debt. Like those are the right ways to catch up. The wrong way to catch up is to jump on Reddit and go like, what is the hottest stock right now? [00:13:46] OG: Or, you know, you see something on YouTube or something crazy about cryptocurrency and how come your crypto didn’t go up 7000%? And you know, you take these wild swings of bets when you have to remember the people who are having the success with that are the people that are largely the people that are investing that way, have their security all taken care of. [00:14:09] OG: They’re playing with their 5% money. Like this is the sandbox money. Not that, not largely anyway, not the corpus of the portfolio, so to speak. Uh, I think the biggest message that I have for people, you know, people say, oh, it’s a brutal scenario to wake up and be 40 and not have any saved is it’s fine. [00:14:27] OG: There is so much time. Like we do not as humans understand the power of compounding. It is impossible for our brains to, to do. If you think for a second that you’re screwed because you’re 40 and you haven’t saved anything, I think you’ve got a great opportunity. Look, you’re not gonna retire probably at 51. [00:14:45] OG: Maybe that’s not gonna be the case, but you can have a great retirement at 60 or 65 or 70. You just probably have to do things a little different. [00:14:53] Joe: Roger, you just showed a graphic, which is, uh, great for the people that are live for this on YouTube, but for the audio listeners, they’re, they’re not gonna be able to get that. [00:15:02] Joe: What’s, what’s the graphic all about? [00:15:04] Roger: Well, he mentioned compounding, and that’s what we’re talking about. If you think of someone that’s age 40, they compounded certain types of behaviors to get to where they are now. And obviously life throws you curve balls in every which way, but that’s always going to happen. [00:15:19] Roger: The issue that a 40-year-old or any of us have to deal with is, what do I, how can I influence the scope of that compounding, either positively or negatively, and a little bit of change now. If you keep doing what you’ve always done, you’re probably gonna be in the same place. But the key is how do I change the trajectory of that compounding when it comes to money? [00:15:40] Roger: And yeah, drastic is nice, but any improvement is, you know, better than nothing. [00:15:46] Joe: Jackie, I like your very thoughtful beginning. Think of where you’re at, how did you get to this point? Where are you at? What’s going on, you know, with you mentally. And then I also like then run the numbers and really, it’s almost like you’re wearing a master shirt today. [00:16:00] Joe: It’s Master’s weekend, so it’s almost like a golfer setting up their shot. I don’t golf myself, but you know, the golfer just rolls up and wax it. It’s probably not gonna, I don’t ever see pros do that. Let’s though begin to get in action. Let’s say it’s time to take action. What is the first move? Not perfect plan, but I’m sure we’re all gonna have some candidates for what maybe the first move would be. [00:16:22] Joe: What would yours be? [00:16:24] Jackie: I think my first move would be, of course, you know, like look at some important numbers. Okay. Investing certainly is a part of it, but also. If you work for a company, how much are you contributing? Some people may have stuck with the company match all of that time, or might not have it at all. [00:16:41] Jackie: So can you start there? Most people start investing through their employer sponsored plan, so if you have that, take advantage of that. [00:16:47] Joe: So that’s a fine place to start, is through your employer putting money in 401k [00:16:51] Jackie: Yeah. Or, or whatever your company sponsored retirement plan is. If you don’t have that, you know, make sure, uh, you’re looking at the debt. [00:16:58] Jackie: We talked about the debt a little bit. High interest debt, so I’m not necessarily talking about your mortgage, but if you’ve got, let, let’s start with the worst of the worst payday law, okay? Mm-hmm. Those, mm-hmm. Those need to be knocked out like as soon as possible. They deserve focus. Maybe you are living above your means and you’ve got a 28% credit card interest rate, where you’ve got thousands of dollars that you’re trying to pay off. [00:17:20] Jackie: That should be lined up. You should have a plan for that. Now, I’m a believer in the fact that we are all masters at multitasking, so you can invest. And pay off your debt at the same time. It’s just a matter of how much you go towards each. So as you pay the debt off, then maybe more should go towards the investing. [00:17:39] Jackie: The other thing, I really like people to tap into their superpowers. I mean, we have a tendency to focus on the negative things and the fact that we don’t have compound growth and things like that. Well, and I guess another thing I like to mention is that we’ve been led to believe and convinced that the trajectory to retirement is about a 40 year time horizon and why That’s because of pensions, right? [00:18:04] Jackie: Sure. Well, really when we dove into it with some late starters and track them, and including myself, it’s more like a 10 to 15 year journey. So you could have some compounding. So I started 38, woke up, and by the time I was like 49, I was to the place where I’m like, wow, this is crazy. But. Waking up and realizing that you’re far behind, that’s a hell of a motivator. [00:18:32] Joe: Yeah. [00:18:32] Jackie: So you get motivated and you are gonna surprise yourself with how fast you move. So looking at a 10 to 15 year trajectory, that changes your mindset right away. So that can help but find your, your superpower. Um, when you get a little bit older, let’s say you’re in your fifties, now, you are kind of through that bottleneck. [00:18:49] Jackie: When I say bottleneck little kids in expensive daycare, okay, you just got the big house, you just graduated. You got student loans, you got a bunch of debt. All those things are squeezing at you at one time. Well, by the time you’re 50, maybe the kids are growing outta the house. Maybe you don’t need the big house anymore. [00:19:05] Jackie: You don’t have the expensive daycare. There’s just so many things that open up in your forties and your fifties. Typically, you’re at your, a lot of people are at their peak earning years, so there’s a lot of things working for you that I think, you know, sometimes we’re too hard on ourselves and we don’t think about those things. [00:19:19] Jackie: So can any of those pieces help you move a little faster? [00:19:24] Joe: We talked about this on Monday, show OG about ways to cut your spending and Jackie’s kind of talking about, do I value this stuff anymore? Right. But she also said that putting money into this retirement plan, just the match, didn’t say this, Jackie, but insinuated, I would believe that that’s a mistake. [00:19:42] Joe: What’s the number we should shoot for? I mean, it, it, it might be individual person to person, but is there a, is there a number that I should say, Hey, let’s see if I can do this percentage and if I can, I’ll back it down. [00:19:54] Jackie: Well, [00:19:55] Joe: oh, wait a minute. That one’s for og. Oh that, [00:19:57] Jackie: okay. That’s og. Okay. [00:19:58] OG: Jackie’s on a roll, man. [00:19:59] OG: I’m just a willing participant. Don’t get [00:20:01] Jackie: og. I’m throwing it to you. [00:20:02] OG: Stay outta the way. She got it all handled. I was thinking about the scene from Austin Powers where he goes $1 billion. Like I was trying to, I was trying to think about that. [00:20:11] Jackie: Yeah. [00:20:11] OG: Yeah. I don’t know that there’s a correct number, you know, like a percentage to have or [00:20:16] Joe: Yeah, [00:20:16] OG: like shoot, whatever, [00:20:17] Joe: like shoot for 20 and if you can’t do it, go 15 [00:20:19] OG: or, well, I guess the way that I would think about it is a little bit more about progress and not like this ideal number. [00:20:24] OG: And what I was kind of encourage people to look at is, can we figure out a way to increase our savings in such a way that it doesn’t hurt? And there’s two different ways to do that. There’s the tear, the bandaid way off and you go, okay, this is just gonna suck and I need to go from nothing to, I need to be saving 20% and that’s gonna cause a lot of upheaval, you know, and maybe you’re the person that has been doing the 401k to the match and you’re getting your 3% and 3% match, and so on and so forth. [00:20:51] OG: Can you set it up so that in June you increase it to 4%? I mean, if you’re making a hundred thousand dollars and you increase your savings by 1%, that’s a thousand bucks, right? Divided by a month. That’s $83 a month. If you get paid twice a month, it’s like 40 some odd dollars a paycheck. I’m guessing that we probably don’t miss the 40 bucks. [00:21:14] OG: You know, like for some people, and I get, for other people they would, so a lot of this is trial and error and, you know. Yeah, I, I would also say for some people the right answer is. Put it at 20, find out where the pain is, and then back it down to 15. You know, like put the heavy weight on the bar and see if you can lift it and see what happens, right? [00:21:34] OG: I mean, as long as you got a spotter, you’re good. Right? You kind of know thyself there a little bit. But if I was setting this up, if I was 40 and saying, okay, hey, I have been doing the match. I, I, I do recognize I’m a little behind air quotes and I need to do a little bit more. How can I automate this? If you can say, well, every six months I’m gonna add a 1% to my savings rate. [00:21:52] OG: Yeah, it’s gonna take you five years, but in five years you go from 3% to 13%. Like that’s a pretty profound change and it’s gonna feel it a non-event the entire time. So see if you can automate the change to make it something a little bit more, um, palatable on the lifestyle. [00:22:10] Joe: I love that idea of Jackie saving through work. [00:22:13] Joe: Roger, and this will be our last question before we take our mid session break. What if you are working for a company that doesn’t have that retirement plan? Is there a way to set up the thing that Jackie’s talking about? ’cause essentially what I love about that, Roger, you hide money from yourself, right? [00:22:28] Joe: I mean, it just, it’s automatically gone. Can you set that up on your own? [00:22:31] Roger: Yeah. Well, you can set up an individual retirement account and contribute. You’re not gonna get a company match. But can I go back to another point that I think is really important in terms of where to start? Nope. [00:22:41] Joe: Of course you can. [00:22:42] Roger: When you realize you have this moment, I’m 40, I have no money and I gotta deal with retirement. Our tendency is to want to take drastic action. And there’s a risk with getting shot out of a cannon with motivation to totally change your life. Then you slowly come back down to earth ’cause it’s not sustainable. [00:23:04] Roger: What I think is probably an approach that we should consider and I’ll, I’ll use a health approach as an example because I’ve been doing this for 15 plus weeks, is actually to go micro and start to connect dots and pay attention to every dollar you spend and every dollar you save and make micro adjustments. [00:23:22] Roger: So as an example, let’s use food as an example. If I have a target of a certain amount of calories for the, and I’m tracking every single calorie that I eat, my choices change. I’m not gonna eat mixed nuts ’cause they’re calorie dense and low protein. But I’m at the store, I’m gonna say, oh wait, do I wanna spend that much calories on? [00:23:42] Roger: You know, ravioli when it’s not going to gimme what we want. It helps to change the individual habits. I [00:23:48] Joe: thought [00:23:48] Roger: the answer and that’s what real pain. But anyway, I was [00:23:50] OG: like, ravioli is so yummy, Roger. [00:23:54] Roger: I know. It’s, but until we start connecting those dots, then ’cause you don’t diet, you get, you get healthier, you don’t become a crazy saver. [00:24:02] Roger: You become a better spender and saver of money. And those happens in the micro moments. And I think if you don’t connect those dots, there’s a risk of going out out of the cannon and then slowly coming back down to what normal is. [00:24:13] Joe: I love that. Looking at every line I’ve been going, how much do I actually enjoy this? [00:24:17] Joe: It’s almost like, Roger, you’re putting, uh, who was that? Marie Kondo on this Every single thing. Go through your, your banking app and go, does this spark joy? And if it doesn’t spark joy, then then get rid of it and add it to that IRA or that 401k [00:24:32] Roger: and ’cause it. That sustainability of whatever changes you’re gonna make is the most important thing because otherwise, oh, it doesn’t work. [00:24:38] Roger: I give up and I’m going back to what was. [00:24:40] Joe: Well, and I think that’s also a key is, is you’re gonna fall off the horse, get back on, I mean, you’re going to fall off. It’s just gonna happen at the halfway point of our Friday shows. If you’re brand new to Docu Benjamins, we have this year long, completely professional, very high stakes tournament going on all year long between our three frequent contributors, og Paula Pant from Afford Anything, and Jesse Kramer. [00:25:07] Joe: And so just to make it easy for me as the host, we’ll have Jackie, you’re gonna be Team Paula today. And then Roger, you’ll be Team Jesse, which means, guys, there’s some good news and bad news for both of you, I think Doug. Um, well, Jackie, let’s ask you, do you want the good news or the bad news first, [00:25:24] Jackie: always bad news first, [00:25:26] Joe: Doug, what’s the bad news? [00:25:27] Doug: The bad news is you are sitting squarely, firmly uncontested in last place, [00:25:34] Joe: and the score overall is bad news for Roger. [00:25:37] Doug: Uh, yeah, because he is, uh, also sitting in a very comfortable second place. [00:25:43] Joe: Yeah, [00:25:43] Doug: no one’s really challenging you for a second. So our overall score is the Prince of Darkness, og. He has seven points. [00:25:51] Doug: Jesse slash Roger has two points and Paula, Jackie clinging to life with just one point, [00:25:59] Joe: but they’re on the board. Finally. It took the em a couple weeks ago to actually get on the board, which is super exciting. So now, now the stage is set for Q2 and that means we need a trivia question. Doug. You’ve got it man. [00:26:12] Joe: What are we talking about today? [00:26:14] Doug: Did we explain that? That means that uh, because Jackie’s in last place, that she, uh, gets to go last and get the benefit of hearing everybody else’s guess [00:26:23] Joe: we did not. That does mean Jackie, thank you that you’re going last. Roger, you’ll go in the middle and og ’cause he’s in the lead is gonna have to guess first. [00:26:31] Joe: So here we go, Doug. Uh, I won’t explain margin calls to everyone. If you’re new to this show, we have a thing called Margin Calls. There will be none today ’cause we have two guests on the show. So no need for that. There will be none. So let’s do some trivia. [00:26:47] Doug: Here we go. Hey there Stackers. I’m Joe’s mom’s neighbor Doug and holy cow, I’m going bananas over here. [00:26:52] Doug: Remember how on that one show there was always money in the banana stand? Heck yeah. While that might’ve been fiction. Turns out it really occurred back in London one day. London Onan. Um, London. Hes London Knights. London Draper. Hmm. Anyway, people who live there, they woke up and found a banana stand smack D in the middle of town. [00:27:16] Doug: Here’s your big question for today. What year did London first go? Bananas for bananas. I’ll be back right after I find out if maybe I can smuggle a smuggle. I’m not gonna smuggle anything, but I’m gonna figure out if I can smuggle a couple of bananas down to the basement. Come on over if you want to try one. [00:27:35] Doug: They’re delicious. [00:27:36] Joe: Bananas are delicious and Roger, to your point, they’re healthy. Right? Got all that potassium? [00:27:42] Roger: Potassium, [00:27:43] Joe: yes. Alright. OG bananas first appeared in London for sale in what year? [00:27:51] OG: Okay. I was gonna ask a little bit of a clarifying question. In a banana stand being like a gimmick thing or like, literally the first time somebody saw a banana in London, [00:28:00] Joe: it literally was the first time a banana was for sale. [00:28:03] Joe: Yeah. [00:28:03] OG: So this is, this is more like the 1970s, not the 1990s. Okay. Right. [00:28:08] Joe: It might’ve been 83. [00:28:10] OG: Ooh, 83. I hadn’t thought about the eighties. Alright, so, um, I am going to say that a banana first appeared, interestingly enough, I actually know this, uh, because it was a monkey who brought it. So they brought the monkey, monkey carried a banana. [00:28:28] OG: They beat up the monkey and took the banana. It’s a weird story, but uh, it’s a part where Doug didn’t want to do that part of the story, but it had to do with smuggling monkeys, uh, from the rainforest. And, uh, the first person to do that was PS de. Pons did that in the year of our Lord. Famous [00:28:47] Doug: Londoner. [00:28:48] OG: Yeah. Yeah. Well, he made a pit stop on his way back to Spain. Areyou
[00:28:52] Doug: talking about on Steel Leon? He was from the south side of London. [00:28:56] OG: No, he was from Spain, but he, he, he played both sides of the alley. [00:28:59] Joe: Oh, Jackie backstage. I told you, we pontificate about the answers. [00:29:03] OG: No, this isn’t pontificating. This is, this is how it went down. [00:29:06] OG: But anyway, old Poncy, uh, that’s what we called him asthey
[00:29:09] Joe: called him. [00:29:09] OG: He captured that, uh, Peruvian monkey and all the bananas in, um, sometime around, um, the same time that Columbus sailed the ocean blue. So 1505. [00:29:21] Joe: 1505. What do you think about that answer, Roger? [00:29:26] Roger: I love, he said, I don’t know what he was talking about, but I love that he talks with confidence. [00:29:33] Joe: Yes. [00:29:34] Roger: I love that he talks with confidence. I’m not gonna pontificate as OG did. I was spending the whole time. Did bananas come from South America, Africa, both places. I was still working on where the hell a banana comes from. [00:29:49] Joe: I actually don’t know where the bananas originally came from in London. I, I didn’t look up that part of the trivia. [00:29:53] Joe: That is interesting. [00:29:54] Roger: Walmart. [00:29:56] OG: I know. [00:29:58] Roger: I’m gonna say that it was from Africa, not South America. And obviously it had to do with colonialism and all of that. But I’m gonna go earlier. When did they have the first sail ships? I need to figure this out. Um, [00:30:11] OG: Magna Carta. [00:30:14] Roger: I’m gonna go 1476. [00:30:18] Joe: 1476. So Jackie, we’ve got 1505 and 1476. [00:30:29] Joe: We’re several hundred years ago and there’s only a 31 year delta between their answers. [00:30:36] Jackie: Look, I, I was never the best in history, but I, I feel like I need to phone a friend, but I’m thinking logically. So we’re saying in the, in the UK right? Did you say the uk? Yep. [00:30:47] Joe: Yep. In London. [00:30:47] Jackie: Okay. In London. In [00:30:48] Joe: London. [00:30:48] Joe: Not, not London, Ontario to be, to be [00:30:51] Jackie: clear, correct? Correct. Okay. So when I don’t know the answer to something, I just try to apply the logic of what I do. No, just like I did on the CFP exam. Okay. So I think, so I’m thinking about transportation things. ’cause if they couldn’t grow it in the uk, they had to bring it over here. [00:31:10] Jackie: So I’m thinking more recent. So I’m gonna go with 1850. I think that’s just closer. I feel like way back then. Oh my gosh. [00:31:23] Doug: Did you say 18 55 0 or 58? [00:31:27] Jackie: 1850. [00:31:28] Doug: 1850. Okay, [00:31:29] Jackie: well, well wait a minute. What? So were they given their Wait, wait, wait, wait. Maybe I misunderstood what they were saying. So, so were you guys given the year that [00:31:37] Joe: Yes. [00:31:37] Joe: Yes. [00:31:38] Jackie: Okay. What was, what were the an, can you repeat the answers for me? [00:31:40] Joe: Yes, yes. Think about this strategically too, Jackie. Like it’s a game. All you gotta do is be the closest person. So, uh, 1476 is Roger. [00:31:51] Jackie: That’s the year. 1476. [00:31:53] Joe: That’s right. Then 1505 is og. [00:31:56] Jackie: Okay. For my gaming strategy, I’ll say 1550. [00:32:00] Joe: 1550. [00:32:02] Jackie: Because it’s closer to what OG said, but I feel like it was more recent than that. So I’ll go up just a little bit. [00:32:09] OG: We boxed you in, og We boxed you in, buddy. [00:32:12] Joe: That’s right. [00:32:13] OG: It’s just another opportunity for the judges to have to have an overruling. [00:32:18] Joe: Team [00:32:18] OG: coaching. Coaching the witness. Your Honor, [00:32:21] Joe: we didn’t coach anybody. [00:32:22] Joe: I was just like, it’s a game. [00:32:23] OG: Think about [00:32:24] Joe: it like it’s a game. [00:32:25] OG: Yeah. [00:32:26] Joe: It’s a hundred percent a game, isn’t it, Doug? This is just a game, right? [00:32:29] OG: Yeah. [00:32:29] Joe: So [00:32:30] OG: I’m gonna stop playing. I’m done playing this game. [00:32:32] Joe: We’ve got Roger at 1476, OG at 1505. Jackie at 1550. We’ll see who’s right. We’ll be back. OG began at 1505. [00:32:44] Joe: Feel pretty confident about that number. No. [00:32:47] OG: Because [00:32:48] Joe: why not? [00:32:48] OG: You’re giving everybody a bunch of information. So [00:32:51] Joe: I didn’t give anybody any information. I just said it’s a game. Just carry on. She’s never played before. Go [00:32:55] OG: ahead. No, no, go [00:32:55] Jackie: ahead. Hey, gimme a break. I’m a little new around here. That’s [00:32:57] Joe: okay. [00:32:58] Joe: That’s right. That’s alright. She’s never played. Roger. 1476. You’ve got, if it is 1200, you got it. [00:33:05] Roger: I got it. What on [00:33:06] Jackie: earth? [00:33:07] Roger: We got the Romans that came over to London. You know they had monkeys. They probably went to Africa or wherever beforehand. I think I’m good. [00:33:14] Jackie: Oh, well that one completely threw me off. [00:33:16] Joe: No, he was saying if it is, it’s not. [00:33:18] Joe: And then, uh, and then Jackie you got 1550 feeling good? [00:33:23] Jackie: Uh, no [00:33:24] Roger: you should. [00:33:25] Jackie: Shit, they basically [00:33:26] Roger: handed it to you. [00:33:27] Jackie: Oh, I thought you said Roger’s answer was right. [00:33:31] Roger: No. [00:33:31] Jackie: Or the closest. Oh, it wasnt. No, we [00:33:33] Roger: Well, he will say that Jackie, in a moment. [00:33:36] Jackie: Yes. Okay. Okay. Gotcha. Gotcha. [00:33:37] Joe: We’re about to find out. Andrea hanging out with us says, oh gee, it’s called a handicap. [00:33:40] Joe: You ever play golf? That’s right. It’s a handicap. [00:33:42] Jackie: That’s right. That’s right. We talked about golf today. [00:33:44] Joe: Yep. Alright, Doug, you got the answer? Who’s bringing this one home? [00:33:52] Doug: Hey there stackers. I’m banana lover and guy who accidentally made it awkward. Again, Joe’s mom’s neighbor, Doug. So I sneak upstairs to grab a banana and I heard Joe’s mom’s coming around the corner. So just as I reached for the fruit basket, well, I panicked. I just shoved it in my pants. She took one look at me and said, is that a banana in your pants? [00:34:13] Doug: You know how you can never think of a clever thing to say, like right when you need to say it. All I could think of at that moment was, thank you. So I went with that. Turns out that was not the best answer I could have said. So we’re just gonna move on. What year did Londoners wake up to a banana stand that was making whatever they called their version of Benjamin’s right downtown for the first time? [00:34:37] Doug: Well, the answer is 157 years after Roger Guest, 128 years after OG Guest, and just 83 years after Jackie guessed, because the correct answer is 1633, making Jackie slash Paula our winner. It’s amazing. Hey, [00:34:58] Joe: how about [00:34:58] Jackie: that? Hey, look at that. Paula, you owe me won. Yay. Yes, [00:35:02] Doug: she does. [00:35:02] Jackie: I just thought, I thought their dates was just too far back. [00:35:05] Jackie: So I went with 18, I was gonna go with 1800 no matter what. I would’ve won. Right? [00:35:10] Joe: No matter whatyou
[00:35:11] Doug: would’ve won. Yes. Yeah, yeah, yeah. But what’s interesting here is that of how long it took a plantain to make it to London, because they actually originated Roger. You were pretty much half the globe away. [00:35:22] Doug: They originated in Southeast Asia and were sort of domesticated as it were. Apparently they were wild and uncontrollable prior to this, uh, 5,000 bc. So they looked pretty different than what the bananas look like today. But nonetheless, people were using ’em as a crop 5,000 years BC and didn’t make it to London until 1633. [00:35:44] Roger: How do you fact check that? Seriously? [00:35:46] Doug: I got a guy. I got a guy. [00:35:52] Joe: We’re gonna go bananas for the second half of our conversation about you start at age 40, you think that you’re late, what are you gonna do? And I love the conversation so far. You’re not late. And we’ve got this miracle of compounding. And we’re not just compounding returns, we’re also compounding behaviors. [00:36:09] Joe: We’re compounding the things that we do to make a difference when it comes to getting what we want for ourself, which is, in this case, the goal is a great retirement. All right? You got money to invest. Where does it go? I want to give you some types of investing, and I know Jackie, in your book, you go over all these different strategies of investments, but there’s a lot of talk. [00:36:31] Joe: From one corner of the universe about dividend investing, right? And about I want more dividends in my portfolio. For people that don’t understand dividend investing, could, do you mind just doing a very brief, here’s how that works, what that means, but then how do you like it? Let’s, let’s, let’s put your, your take on dividend investing versus maybe other ways to invest. [00:36:54] Jackie: Are you throwing that to me, Joe? No, I, I, so as far as, um, dividends, so for me, I. Also have a single stock portfolio, so that’s looked at a little bit differently. Yeah, so sometimes people do want the blue chip stocks because of their great dividends. We know that dividends isn’t really giving you more money overall. [00:37:14] Jackie: It’s just giving you a portion of their, you know, profits of the company and they pay it out to you by, you know, sending you a check every quarter. I look at dividends as a representation of other areas of strength of the company or not. So, so I keep that in mind. I think some people might be attracted to the whole idea of dividend because they don’t have to sell shares to be able to get it. [00:37:35] Jackie: But you really should be focusing on the overall, you know, return, you know, the growth of the stock or the index fund versus well, and the dividends along with it, and, and. Because most people like don’t really understand how dividends work. Sometimes an an explanation of that will start to make sense to them because some people just think that’s just a free extra bonus that I get every quarter. [00:37:58] Jackie: So, so the education piece of any type of investing is probably one of the most important things. And I suppose if you are thinking about retirement, it’s a nice way to get sort of some fixed income or cash. So that’s okay. But I think there’s some education around doing that because it could work for your strategy, whatever your strategy is. [00:38:19] Jackie: Dividends might have a place for that. I just don’t immediately discount it as in, oh yeah, dividends create. No, you know that, that’s really nothing. You shouldn’t be focused on that. I want to talk them through and walk them through here’s, you know, some benefits, some ways you can use it and things like that. [00:38:35] Jackie: But you know, it’s really not getting them much more of. [00:38:38] Joe: It could be a piece of the puzzle. [00:38:40] Jackie: Yeah, I think it could be a piece of the puzzle, but a lot of times people are confused about how that even works, so it probably warrants a little something. [00:38:47] Joe: Well, and I think my brain was ringing the bell on what Jackie was saying, Roger, because when I hear about dividend investing, the number one thing is you don’t ever have to sell your stock. [00:38:54] Joe: It’s like you still got the mountain of stock and now I’m just taking the dividends. Right. Is there a flaw in that argument? [00:39:01] Roger: Well, the mountain of stock never really grows as much because dividends are simply profits that are given back to the shareholders. Meaning that they didn’t have anything else better to do with the money in terms of reinvest, reinvesting it in the company separately. [00:39:13] Roger: If you’re taking the dividends, you’re not reinvesting in the company or in a say a mu, even a mutual fund, you can reinvest or take it out. I think for someone that’s 40, the key issue is I have to build wealth, I need capital appreciation, and I have a 15 year timeframe in the fact set that you gave us, we hear all these things ’cause we love to talk tactics. [00:39:34] Roger: Tactics are after you have a bigger strategy and it’s really capital appreciation, keep it as simple as possible because, and which is going to be not thinking about dividends or sectors or all of that. Buy a portfolio and focus on the things you have the most agency over. Uh, so I think it’s premature for someone at 40 thinking about retiring at 65 to even being thinking about these tactics. [00:39:57] Joe: I really like og. The other thing that Jackie mentioned too, which is it’s all kind of same, same like dividend capital gain, your stock goes up. Yeah. It might send you to panic a little bit because you’re selling some of your stocks, but a return to return, isn’t it? [00:40:11] OG: I mean it is, and the taxability of it is virtually the same too. [00:40:14] OG: So it’s like, well, I didn’t wanna sell a stock and pay taxes. It’s like, well, but you get dividends and you pay taxes. So tomato, tomato, it’s all return to shareholder like Roger was talking about. One way or the other, it’s the company made money and now they have to decide how best to use the money. And sometimes they decide to use it to buy more stuff or build more product or invest in research or whatever. [00:40:35] OG: Sometimes they use it to reward existing shareholders. Sometimes they use it to line their own pockets, right? It’s like there’s, there’s all sorts of ways you can use profit as a company. And, um, I think what’s most important, um, especially like Roger was talking about here, dividends, capital appreciation, whatever, it’s all return. [00:40:52] OG: And if you’re taking some of that return off the table every year, you’re gonna have a slower growth of your overall net worth in the time where you, you know, are trying to compound it as fast as possible. So. Dividends aren’t neither good nor bad, it’s just if you’re gonna use it to supplement your lifestyle, especially when you’re 40 or 50 or not retired yet, basically, then you’re taken a little bit off the table in terms of your compounding in the future. [00:41:19] Jackie: Fun fact, did you know that Nvidia pays a dividend? [00:41:23] Joe: Oh, [00:41:23] Jackie: they do it. Tiny little one, but you know, hey, that right. That’s something I guess their leadership, uh, get the hot company [00:41:30] Joe: and the dividend. [00:41:31] Jackie: Right, and, and that’s what I love to have both. And it also depends on where you have the money. If you have it in your retirement account at work, then the dividends are gonna get reinvested. [00:41:39] Jackie: So you don’t have a choice. But if you have a brokerage account, then you have all those things that OG was talking about. [00:41:44] Joe: We see lots of channels, Jackie, in the personal finance space that talk about real estate, the magic of real estate. Mm-hmm. This person, 40 years old, just starting out, doesn’t have anything. [00:41:53] Joe: Where does real estate fit in that portfolio? [00:41:56] Jackie: Yeah, in my way. The first thing would be if you own your own home, you’re, you’re owning real estate. Arguable, you know, some people don’t even call that an investing, but it can be beneficial to you. Mm-hmm. Like for instance, I’ve been in my house for a really long time and some people that are 40 or older, potentially they could have been in their house for a while, maybe they have a really low interest rate. [00:42:14] Jackie: So that may be something working to their benefit. But if you have not done real estate before as a wealth building tool, like, you know, you are investing in rental properties or something like that, Airbnbs, it’s probably not the time to really start something new. But if you do it, make sure something that lights you up, like real estate may not be your thing, but there’s a lot of buzz out there that says, Hey, real estate is a quick way to do it. [00:42:42] Jackie: And that could help you catch up maybe if you’re interested, but you’re not gonna stick with it if it’s not something that really interests you. And if you’ve never done real estate before, I don’t know if turning 40 and being behind. Is the right time to do it. Ifyou’ve
[00:42:57] Joe: already [00:42:57] Jackie: got experience with that, then maybe [00:42:59] Joe: might not be the right fit. [00:43:00] Joe: It certainly didn’t light me up, Roger. I don’t know if real estate lights you up, but when you see people, your wife’s [00:43:05] Roger: still trying to figure that out. Joe, [00:43:08] Joe: I just, the real estate thing is so, was so ugly. Uh, where do you stand on real estate for this person? [00:43:14] Roger: Um, I agree with Jackie real estate, and I’m assuming we’re talking about single family properties or buying a commercial building, et cetera. [00:43:22] Joe: Yeah, yeah. [00:43:22] Roger: The beauty of real estate is leverage. That’s where the magic happens. If you go into real estate, you’re going into a business. So it’s really, do you want to be in a business that happens to be real estate? And the way to get the real returns in real estate typically are with leverage. And leverage introduces a lot of risk. [00:43:43] Roger: And I think it’s, do you want to go into business? Is that really where you want to spend your time and are you willing to do it for a long period of time? And that’s a really different kind of decision. I think it’s better for, you know, the fact set that you gave us somebody to walk and build the habits before you start thinking about going into a, a business such as real estate. [00:44:03] Joe: Yeah, I think, and it’s funny, you see, we saw, we had a TikTok, minute Ochi, if you remember this guy saying not only go into real estate, but flipping houses. Roger, of all the businesses out there, you know, real estate as a business, buy a house and long term hold it, maybe have a renter is maybe low impact. [00:44:20] Joe: Business can flare up from time to time. But the flip, somebody telling somebody to do a flip right outta the gate. And I was like, what do you, you’re telling them to do a full blown business. Where do you see OG real estate in a portfolio of this person? [00:44:34] OG: From an investment standpoint, I have a hard time, unless your expertise is in real estate using individual, individual property. [00:44:42] OG: I mean, just, just conceptually from a diversification standpoint, what’s gonna be better? A real estate mutual fund or ETF or one rental property in hometown USA. Like if I’m gonna have real estate, I want it to be as diversified and as liquid as possible and not literally have one thing unless that’s my. [00:45:00] OG: Expertise if I’m a realtor or you know, I have some family connections or something like that. Your real estate story and mine are very similar. We both hated doing it. I think mine’s a little different and I got lucky on timing and so on paper it looks like I hit a home run, which I did, but it’s because I like closed my eyes as, as I had the bat in my hand and just swung and the bat hit the ball. [00:45:20] OG: You know, I didn’t actually try to hit the ball. It just happened and it looked like it was like this magical outcome. And I think it’s true. You know what Roger said about leverage, and this is really the thing that to me puts the nail in the coffin about individual real estate investing because the return only works when you use leverage. [00:45:38] OG: Like you have to put a hundred thousand dollars down to buy a $500,000 property. That’s how that works. And when that $500,000 property goes up 10%, you made 50 grand on your a hundred. And that looks like, uh, you’re a genius. I would submit to you, you can do the same thing with your stock account. You can call Schwab and say, I’ve got a hundred thousand dollars, you guys, let me buy 500,000 worth of stock. [00:45:58] OG: They’ll go, yeah, absolutely. Sure. Nobody does that because, oh, that’s risky. Wait a second. What’s riskier? The biggest, biggest, most, well run, most well capitalized companies in the entire universe. Mm-hmm. Or property in hometown, USA. [00:46:13] Joe: And to be clear, that’s not an endorsement of taking out the margin. [00:46:16] OG: I’m not saying you should do that. [00:46:17] OG: I’m just saying like, to me, that’s the trait, that’s the, when you do the math on both of those, you go, well, I would never do that. They’ll go, well, why would you do it this way then if you’re going to, you know, do it that way And you’re, that’s a great point, og, and you’re adding a lot more execution, risk [00:46:30] Roger: of vacancies and repairs and all the other stuff that comes [00:46:34] OG: with it. [00:46:34] OG: You would never do that with your stock account, right? You’d never take a million dollar brokerage account and go buy 5 million a stock on margin at 7% go, oh, that’s just leverage. It’s great, you know? But we deal with commercial property all day long. I like real estate as an investment publicly held, very liquid diversified as an ETF or mutual fund. [00:46:52] Joe: Well, and let’s talk about that. ’cause Jackie, you’re nodding your head like there’s this wide world of investments. We said dividends only. Probably not. Even though you’re gonna read about that a lot, you’re also gonna read, as a newbie, you’re gonna see people getting rich off real estate. We just said, yeah, it can be great, but probably not a place to start. [00:47:09] Joe: If I’m this 40-year-old person and I got this wide world of investments. What types of investments, maybe what type of packaging am I looking at first to start to get comfortable with where I’m probably more likely to invest? [00:47:24] Jackie: Yeah. I think for most people it’s back to the employer sponsored retirement plan, just like an index fund. [00:47:29] Jackie: And I think just a little bit of education around how the mar stock market performs. I guess the bond market as well, but mostly the stock market. For instance, the stock market will have years where it goes down. No need to take all your money out, no need to panic sell, or anything like that. Look at market history. [00:47:49] Jackie: Um, I’ve gone all the way back to 60 years even, even further, but on average, the stock market is up about 80% of the time. That will help keep you from selling when we have two or three weeks or a couple of months, or even a year of a down market, even if it’s a sharp decline like it is right now, we’re in, you know, near the first quarter of, uh, 2026. [00:48:15] Jackie: So I think that. Something that happens more often than not, they wanna go real aggressive. All stocks, you know, I want the thing that’s gonna grow the most. And then when we hit a downturn, it’s like, oh my gosh, this is too crazy. And they start to understand their real risk tolerance. So that would be where I would look at it. [00:48:36] Jackie: Know how stocks behave. Stock index funds are very common now. They’re very easy, they’re very low cost. So that’s probably the low hanging fruit for most people. But make sure you understand how that performs and that a market downturn is a normal part of the cycle. [00:48:53] Joe: Roger, all these places to look at, Jackie says, this index fund is a great thing to look at first. [00:49:02] Joe: Do you agree? And if so, what’s the attractiveness for you of, of starting to, uh, dig into index funds and begin your research there? [00:49:10] Roger: You want to do as little as possible because. The more you make it something you have to think about, like real estate, the more you have a chance of screwing it up, the more complicated the system is. [00:49:21] Roger: One is, I want to go to your point a little bit earlier related to this, Joe, is, you know this 40-year-old, oh my goodness, I have no savings. You’re like a person that’s dead in the water, feeling like they’re just trying to keep their head above and now they want to swim a direction. And it’s easy when you’re in that mental state to grab for the the easy button. [00:49:41] Roger: The risk is becoming more susceptible to man go on the internet. You find it all over the place. Everybody has a strategy, real estate millionaires and people sitting outside in front of their Rolls Royces. You could potentially be a sucker for a lot of these things that are just really bad for you because it’s the boring stuff that is the right stuff to do. [00:50:00] Joe: That actually is funny, Roger. ’cause as you’re talking, I’m going back through the three things we talked about. If we go with the index fund guys, it’s uh, okay. Do you have dividends, Jackie? To your point earlier about Nvidia and some of these companies, Coca-Cola, whatever, you’re like, yeah, you got some of that. [00:50:13] Joe: It’s not all, but yeah, you got some And then real estate. Yeah. All these companies own some real estate. Maybe not all of ’em, but a bunch of ’em. Yeah. You got a little bit of real estate. Yeah. So, Roger, it’s, you’re saying it’s not the winner to research first because you’re gonna win. It’s because you’re less likely to lose. [00:50:28] Joe: Is that what you’re saying? [00:50:29] Roger: I’m saying that you should keep it really simple. I do think just invest in the current of the economy. And that’s essentially what you know, the economy is this current, it has a current that is going to growth and there are rapids, periodically of bear markets and corrections. [00:50:45] Roger: And that’s the price for being on the river. For this 40-year-old build the habit of saving in the most efficient way. And you wanna be on Tom Sawyer’s raft in the river. Something that costs not much to build. You don’t have to think about navigating it. You’re just trusting that every now and then you’re gonna get wet when you hit the rapids. [00:51:03] Roger: But because you have the proper timeframe, you can grow with it. And I think the simpler you make it, the better at this stage. [00:51:10] Joe: But it’s funny in the comments today, man, dividend gypsy hanging out with us says, Hey, but to play devil’s advocate, historically, OG don’t, companies that grow dividends annually have a greater total return than non-dividend payers. [00:51:24] Joe: You could not only get dividends, but also be in the hottest stocks. [00:51:28] OG: Well, I think it’s just cherry picking data. It depends on how you analyze it. I mean, is the dividend paying the reason for the high long-term performance, or is the fact that most dividend payers are companies that have been around 25 years? [00:51:42] OG: And, you know, those are backward looking statistics. I don’t think you can look at a stock today and say, oh, NVI, well, NVIDIA’s a bad example ’cause it’s kicking everyone’s ass. But, but you know, this, this company pays a dividend, therefore it’s gonna outperform. There might be a trend of over the last 30 years or 50 years, if a company historically raises its dividend, it also has outperformed. [00:52:07] OG: But why did it do that? It did that because it was a great business that created a lot of value for a lot of people. The problem is, is that you don’t know what those great businesses are that are providing a lot of value for a lot of people in advance. Also, I would say you don’t know because they’ve been a great business that provided a lot of great value for a lot of people for the last 20 years, that there’s any indication that they’re gonna do that for the next 20 years. [00:52:30] OG: There’s no statistical evidence of the persistence of performance. So I think that the best solution to that is, yeah, you should, you probably will have some dividend payers in your portfolio, but you should also have some non-dividend payers in your portfolio and big and small and international and you know, US based and like a wide variety of basically all the companies in existence because then you get everything all the time. [00:52:55] OG: Like it’s the easiest way to do it. Roger said something about being on a raft with Tom Sawyer. I don’t, I didn’t really follow that, but you know, at the end of the day it’s like, just own one of everything. It takes all the guesswork out of this. [00:53:07] Roger: Well, I think the key here, Joe, is, you know, we go back to agency. [00:53:10] Roger: If you’re 40 years old, do you wanna spend your mental energy thinking about investment strategies or more important things that are like levers that can really impact your life? So a lot of this is just simply time management. [00:53:21] Joe: And that’s important Roger, because what do you need to really do? I mean, you need to grow your income if, if you really feel like you’re behind, the cool thing to do is to grow your income. [00:53:30] Joe: If you can grow your income and save more of that income, then that’s great because Jackie, as I thought through you started this cavalcade of Roger and OG saying Yes, I believe looking at the index fund, what you’re really saying is that your savings rate and a decent sale beats some complex investment strategy. [00:53:52] Jackie: Yeah, it so true. I love to show that chart. One column, it’ll show your savings rate and another column. How many years with that savings rate will it take you to get to financial independence? And that becomes very powerful. So if you only wanna save 10%, then that’s probably gonna take you about 40 years. [00:54:09] Jackie: If you wanna save 30%, then that might shave it down to 20 years. And some people that are 40, it doesn’t mean that the income was their problem, it could be higher income earners. As you know, my co-host, bill Y, he’s a physician and his wife is a doctor as well. So their problem was not income, it was other things like spending everyth, you know, more, more money, more problems. [00:54:33] Jackie: So they just life [00:54:34] Joe: today in the way, yeah, [00:54:36] Jackie: e, exactly. So they still was living paycheck to paycheck, living a big life. And when they realized that they did have a big shovel, ’cause there were just a lot of crumbs falling out of the bottom. And once he identified that, he just became smarter. With how he spent his money before he spent first saved last, he reversed that and said, now I’m going to save first and spend last. [00:54:59] Jackie: And in about 10 years he got to that place. So even for high income earners, unfortunately this can be a problem as well. And that’s why you kind of stop for a minute and say, wait a minute, let me see where things are at. Because the income might not be the problem. The debt might not be the problem. It could be a lot of different issues. [00:55:18] Jackie: The, the better you are at identifying the problem that caused you to be behind, the more likely you can start to close that gap and start your path in the right way, because it’s just not the same for everybody. [00:55:35] Joe: I love this guys. If you’re 40 years old and you’re hanging out with us listening, it’s not too late. [00:55:41] Joe: Savings rate matters more than be getting clever, simple beats complex. There are multiple valid paths, but some are more valid than others. So do some, do some research and I think, uh, action beats perfection. Like don’t try to, don’t try to create the perfect thing. Just get moving. Get moving. I like what you said earlier, og, that you know what, just get started and it’s gonna make it better than it was yesterday. [00:56:04] Joe: Might not be perfect, but it’ll be better than it was yesterday. I think that’s a fantastic place to leave it. It is Master’s weekend. And Jackie, you’ve been to the Masters twice. [00:56:14] Jackie: Three times actually I went to the practice times, practice rounds three times. Yeah, the practice rounds twice. And the actual Sunday tournament once when I was in college. [00:56:22] Joe: Well, the cool thing is I’m gonna ask Oh gee, what he’s doing and I bet it’s sitting on the sofa. Watch in the masters. [00:56:28] OG: You know, I’ve got a little, uh, after school activity this week, kind of, uh, middle of the spring for that. So I will, uh, try to watch as much golf as I possibly can, uh, between that and, um, pedaling my rear end up and down my, [00:56:41] Joe: I was gonna ask you about that. [00:56:42] Joe: ’cause a lot of stackers asking about how the bike is going. [00:56:45] OG: So far, so terrible. It’s uh, but [00:56:48] Joe: you’re doing it. You’re doing it. [00:56:49] OG: No, I, it’s fine. I, I enjoy being outside. It’s very structured, which is what I need. Every day. I don’t, I don’t make stuff up. I just like, literally look at the calendar and see what the coach put in there. [00:56:59] OG: It’s like, ah, four hours. Okay, here we go. I’ll see you later. I just get up, get my ass on mic and go. So [00:57:07] Joe: you’ve seen every trail in the area? [00:57:09] OG: Uh, yeah. Yeah. Trail road. I’m gonna start going to Roger’s house pretty soon. I was gonna say, you [00:57:15] Roger: need to come up for some altitude training, [00:57:16] OG: buddy. He’s in the mountains and I’m gonna go, he doesn’t, he didn’t invite me and he doesn’t know it’s coming. [00:57:20] OG: But I’m gonna show up one day with my like hat in hand and a bicycle and be like, Roger, can you ride your bike with me please? [00:57:26] Joe: From here to there. It might take longer than four hours, but uh, [00:57:28] Roger: get some climbing in. [00:57:30] Joe: Spoiler. Jackie, thank you so much for hanging out with us again. We’ve got the beautiful book behind you. [00:57:36] Joe: People can get that everywhere if they’d like Fire for Dummies, learn about the fire movement through the amazing. Jackie, I gotta ask you about two things. Number one, what’s coming up with you and Bill on catching up to fi. [00:57:48] Jackie: Yeah, so catching up to five, we focus on late starters on the journey to financial independence. [00:57:52] Jackie: So this is squarely in our space. And the other thing is I’ve been getting very frustrated about 4 0 1 Ks that are offered to employees. They’re confusing. The name of the funds are confusing. People don’t know how to do them. And most people sit with the default for a very long time. And I hate that because that is a backbone of most people’s retirement these days. [00:58:12] Jackie: So I created something called the Great 401k cleanup, where I put a guide together on how to clean up your 401k in less than an hour. [00:58:19] Joe: Awesome. And you gotta tell us where to get it. [00:58:22] Jackie: Yeah. Um, you can come on over to catching up to five. We just did an episode that walked through the whole thing and you can download the guide and just the one page checklist just from going to the podcast and it’s in the show notes there. [00:58:34] Jackie: But that’s where we’ve got it. And I just am trying to share that with everyone. Listen to the podcast, download the guide and you’ll be good to go share it with, you know, we got smart people on here, Joe, so they may not need it for themselves, but if you have younger friends, family, nieces, nephews, kids, they’re gonna be looking to you for help and that guide kind of helps you do that [00:58:54] Joe: 87 choices and there are four good ones buried in there. [00:58:58] Jackie: Exactly. I see that all the time. It’s a shame. [00:59:01] Joe: It’s great seeing you. Good. And thanks so much for helping our stackers today. [00:59:05] Jackie: Yep. [00:59:05] Joe: Mr. Whitney, what’s coming up at the retirement answer man? By the way, you are permanently now in Colorado. [00:59:11] Roger: Um, trying to be, I still have my Texas house, but I’ll be here till September anyway. [00:59:17] Joe: Awesome. [00:59:18] OG: According to the IRS, his official residency is, uh, whoa, [00:59:21] Roger: whoa. The [00:59:22] OG: state [00:59:22] Roger: of Texas, whatever those, yeah, whatever those are. Can we edit that out, please? [00:59:26] OG: Edit. [00:59:27] Roger: No. I’m officially a resident of Texas, but in Colorado currently? [00:59:31] Joe: Yes. [00:59:32] OG: Occasionally visit Colorado. Yeah. I’m with you, Roger. I’m, [00:59:35] Joe: but we gotta talk about what’s happening at, uh, the retirement answer, man. [00:59:38] Joe: The Rock Retirement Club. [00:59:39] Roger: Well, this month in April, we’re answering listeners’ questions, but I’m excited about May ’cause, may, we’re gonna have an associated Marie Kondo come on and talk about decluttering for retirement. [00:59:51] Joe: Wow. I didn’t even know that. And I brought up Marie Kondo earlier. I’m feeling [00:59:55] Roger: pretty. [00:59:55] Roger: I know. I don’t, it’s amazing. Not, you know, you can declutter obviously your home and everything else to renest, I call it, for your new phase of life. But also there’s a lot of decluttering that has to happen financially because you sort of gather old 4 0 1 Ks and IRAs and these things that you thought you were gonna do. [01:00:11] Roger: So we’re gonna have a whole month long series on decluttering. [01:00:14] Joe: And that’s at the Retirement Interband Podcast, where finer podcasts like catching up to Phi and Stacky Benjamins or Phone. We’ll link to all these great shows in our show notes at stacky Benjamins dot com. We also have a, uh, friends page and you guys are both on our friends page on Stacky Benjamins as well. [01:00:32] Joe: You can find the shows we think are pretty damn cool on that page as well. Alright, that’s gonna do it for today. Thanks to everybody hanging out with us on YouTube. We’re super happy that you’re here. Speaking of, uh, if you’ve got a friend, if you’ve got a friend who is this 40-year-old. Who’s just, uh, starting out? [01:00:48] Joe: Maybe send them to this episode because that you guys really nailed. I think a lot of the key issues to begin what’s gonna be a much, much longer journey than the one hour we took. But it’s a wonderful place to start the trip. Doug, you got it from here, man. What should we have learned on today’s show? [01:01:04] Doug: Well, Joe, first take some advice from Jackie. No matter how late you are saving for retirement, you’re never too late to start. Start slow, start simple. And before you know it, the power of compounding will make a bigger difference than you’d ever believe. Second, don’t forget what Roger said when you’re trying to get up to speed. [01:01:22] Doug: Don’t put all your eggs in one basket looking for the silver bullet that’s gonna hit a home run. You’ve got to diversify. But the big lesson, don’t rely on some pile of hidden money suddenly showing up at the last minute. Turns out there isn’t always money in the banana stand. Thanks to Roger Whitney for joining us today. [01:01:43] Doug: Wanna learn more about Roger? Just Google retirement. Answer man or head to roger whitney.com. We’ll also include links in our show notes at Stacking Benjamins dot com. Thanks to Jackie Cummings Koski for hanging out with us today. Check out her book, fire for Dummies or her incredible podcast, catching up to Phi, wherever you listen to the finest podcasts. [01:02:04] Doug: And finally, thanks also to OG for joining us. 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 2026, and is created by Joe Saul-Sehy. 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. [01:02:29] Doug: And all the usual social media spots. Come say hello and oh yeah, before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. 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. [01:03:03] ending: Oh, oh. [01:03:05] OG: What’s wrong with you? [01:03:07] ending: Oh, it’s either this show or indigestion. I hope it’s indigestion. Why? It’ll get better in a little while.
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