Think your retirement plan is bulletproof? Think again. In this eye-opening episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by certified financial planner Jeremy Keil, CFP® to walk you through the steps to building a retirement plan that won’t crack under pressure. From mapping out your spending before you ever leave the workforce to crafting a tax strategy that keeps more money in your pocket, this conversation is your blueprint for making your golden years actually golden.
But just when you think you’ve got retirement handled, we throw a curveball: private equity. With giants like Goldman Sachs and T. Rowe Price trying to slip these complex investments into your 401(k), it’s time to ask whether “more opportunity” is really a good thing — or a trap for the unprepared. Joe and OG break down the risks, the realities, and what you need to know before you sign on the dotted line.
As always, we serve it all with a side of basement banter — from Doug’s trivia about the first issue of Playboy to a TikTok football moment you didn’t know you needed — plus real-life stories that prove retirement planning is as much about mindset as it is about math.
What You’ll Learn In Today’s Show:
- The five key steps to building a retirement plan that works for you, not just a generic spreadsheet.
- Why starting with your spending habits (not investments) can make or break your retirement success.
- How to prepare for the emotional side of retirement — including those pesky “what now?” questions.
- The surprising risks of private equity creeping into your 401(k) — and how to decide if it’s worth it.
- Smart tax strategies to make your retirement money last longer.
- How long-term care, market volatility, and unexpected expenses should factor into your plan.
Questions to Ponder During the Episode (and discuss with other Stackers!)
Are you planning your retirement based on your lifestyle — or someone else’s idea of “enough”?
What’s one spending habit you need to understand now to avoid retirement surprises later?
How would you react if your employer added private equity options to your 401(k)?
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
Our Mentor: Jeremy Keil, CFP®
Big thanks to Jeremy Keil for joining us today. To learn more about Jeremy, visit Milwaukee Financial Advisors & Retirement Planning | Keil Financial. Grab yourself a copy of the book Retire Today: Create Your Retirement Master Plan in 5 Simple Steps. Listen to Jeremy’s podcast, Retire Today at Retire Today – Podcast – Apple Podcasts.
Our Headline
- Goldman Sachs, T. Rowe Price to offer alternative investments for wealthy clients by 2025-end (Seeking Alpha)
Doug’s Trivia
- Who was the one-time struggling actress who appeared in issue one of Playboy?
Have a question for the show?
Want more than just the show notes? How about our newsletter with STACKS of related, deeper links?
- Check out The 201, our email that comes with every Monday and Wednesday episode, PLUS a list of more than 19 of the top money lessons Joe’s learned over his own life about money. From credit to cash reserves, and insurance to investing, we’ll tackle all of these. Head to StackingBenjamins.com/the201 to sign up (it’s free and we will never give away your email to others).
Join Us Friday!
Tune in on Friday when we’ll dive into what one author suggests your plan needs to make it shine with our roundtable panel.
Written by: Kevin Bailey
Miss our last show? Listen here: Does The American Dream REALLY Costs $5 Million? (SB1741)
Episode transcript
[00:00:00] Doug: What a filthy job could be worse. How could be raining? [00:00:16] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show. [00:00:30] Doug: I am Joe’s mom’s neighbor, Doug. And how’s your retirement plan coming along looking for a succinct step-by-step approach. We’ll outline five steps to a better plan on today’s show featuring CFP Jeremy Kyle, and in our headline segment. As Mom says, the future is now money management is a changing as t Rowe Bryce and Goldman Sachs join. [00:00:53] Doug: Forces to market. Goldman socks. Goldman socks. I, I heard that too. Goldman has some socks. Yeah. Why did I, I said the word. I keep on moving on with the rest of the sentence and in my head I’m, I’m hearing myself say, why’d you say socks? It’s not socks. OGs gonna say, why’d you say socks? Well keep bringing it, man. [00:01:11] Doug: Let’s go. Okay. I’m gonna back up and say, and Goldman Sachs join forces to Market More investments to you. But are these in your best interest? We’ll share. And speaking of share, I’ll also share a talk talk minute, and then I’ll share some incredible money themed trivia. I’m killing it today, aren’t I? And now two guys who still owe me for the last round of ice cream plus interest. [00:01:35] Doug: It’s Joe and O. [00:01:41] Joe: Hey there, stackers. Welcome back to the party. It is the Stacky Benjamin Show. We’re super happy that you’re here. Sit back and relax and get your retirement game face on because OG. We’ve got a new friend that I made at, uh, FinCon upstairs, talking to my Joe. Finally [00:01:56] OG: made a friend Doug. I finally made a friend after all these years. [00:01:59] OG: He finally got one friend at FinCon. [00:02:03] Joe: It’s weird when you go up to people at FinCon and you say, will you come down to my mom’s basement and talk to me? Like, it just, I don’t know. I don’t know what is. Uh, that sounds great. Why that doesn’t garner more of a response. But Jeremy Kyle is a certified financial planner in Milwaukee. [00:02:20] Joe: He’s also the host of the Retired Today podcast. He’s got this great simple framework to make you think about the five steps to retirement. If you’re new to retirement planning, uh, you know what? I think that his first step is going to surprise the hell outta you. It’s, uh, gonna be super fun. Can’t wait for that. [00:02:37] Joe: But let’s introduce you to the team who’s here with me. You already heard Doug’s voice, and the other voice you heard was, uh, my partner OG is here. How are you? [00:02:48] OG: When you say the team, I think of the be she beckler. The team. The team. The team. We want a Stacking Benjamins man doing the Stacking Benjamins open. [00:02:57] OG: Yeah. You probably don’t know that whole bit Joe, ’cause you’re a green and white fan. But I know Doug does. I steel absolutely do steel bow. The boat. Absolute. Absolutely. Team. The team. The [00:03:06] Joe: team. I have a TikTok minute related to that. That was sent to me. Okay. Well, yes, related to football. Might be a little respite from Financial Talk right in the middle of the show, but super great and sent to us by our friend, Steve. [00:03:22] Joe: Hey, we’re gonna have Jeremy coming up in a second. Jeremy, as I mentioned, is the host of the Retire Today Podcast. He’s also the face behind the Mr. Retirement YouTube channel. He’s been a financial planner. CFPC. F-A-C-I-M-A-C-L-T-C. He’s got ’em all, og, he’s got all, he’s all the Cs, all the stuff he practices in Milwaukee, Wisconsin, where a good friend Emily. [00:03:45] Joe: Guy Birkin lives home of the Brewers. Yeah, home of the brewers man. Brewers had a great baseball season this year too. We’re about to hear from Jeremy in a second with five steps toward your retirement plan. But before we do that, we have some sponsors Help us keep on keeping on. You don’t have to pay a dime for any of this. [00:04:01] Joe: Goodness. So we’re gonna hear from them. And then Jeremy, Kyle joins me at the card table to talk retirement planning. [00:04:19] Joe: Super happy. This gentleman’s coming down the stairs. It’s about time we got him here. I’ve been enjoying his podcast. Jeremy, Kyle joins us. How are you, man? Doing all right Joe. How you doing? I’m doing great. And it was so good to see you recently in Portland, Oregon. I’m like, I know that guy. And like, I went up to you. [00:04:33] Joe: I’m like, I, I’ve been loving your show lately, man. [00:04:36] Jeremy: Yeah, I appreciate it. And you’re telling me that one of your favorite episodes, you’re listening to it in the shower, so I’m glad it’s not a, uh, two-way media, [00:04:46] Joe: my ability to make, uh, nice to meet you. Awkward. Jeremy is phenomenal. Like, I’m very good at it. [00:04:51] Jeremy: I’ll, I’ll never forget it. And now the rest of us won’t, won’t forget [00:04:54] Joe: it either. I’m sure all of our stackers are glad they heard that part. You know, I wanna start off with this, uh, current project of yours, not the podcast, but this idea of Retire Today, which is the name of your new book and certainly stackers. [00:05:10] Joe: We’re not going to sell you on Jeremy’s book, but I do wanna use it as a backbone for our discussion. If somebody’s listening to this and they’re 35 years old, I’ve known you work for a long time, Jeremy retire today. Why today, even if it’s gonna be 20, 25 years in the future, why is the word today in the title. [00:05:29] Jeremy: Well, I say retire today because it’s all about taking control of your retirement today. And if you start early 6:00 AM you might be able to clock out at 5:00 PM and be done with it if you follow the steps. But most people, I’m guessing it’s all about, let’s just take control of our retirement today. And I share a story in the book of someone who came in just completely flustered. [00:05:49] Jeremy: They just took a job paying them $20,000 a year more. ’cause they felt like they had to, they had to take this job that they hated so they can make their retirement work down the road. I walked her through the steps that you take to, uh, control your retirement and she ended up quitting the job, kept on working for three more years because she loved what she was doing with her normal job. [00:06:10] Jeremy: But it’s all about taking control of your retirement today. [00:06:13] Joe: It’s funny, have you seen the statistics that the average person spends more time planning their vacation than they do planning retirement? [00:06:20] Jeremy: I’ve seen that. I’ve got, uh, quoted, uh, and the book blur. So you and I are reading the same, uh, resources. [00:06:26] Jeremy: That’s exactly it. And I, and I’ll butcher the exact numbers, but it’s something like, uh, lemme take a look at my 401k for less than an hour a year, but let me plan out my car purchases and my vacation for hours upon hours per year. A little more impactful to figure out what you’re gonna do for the last 30 years of your life. [00:06:41] Jeremy: Perhaps worth putting some time into it. [00:06:43] Joe: Well, and it is, and you love this. You can tell your enthusiasm for financial planning. I love financial planning, which is why we do the podcast. Even for somebody that’s not a money geek like you or me, Jeremy and I haven’t been a financial planner in a long time, but it was really fun to sit down with somebody and to have them start dreaming about what could my life be when I take control? [00:07:04] Joe: Like what are the cool things that I could do that I’m not doing right now? Like it truly is a lot more fun than planning the next car purchase. I think. [00:07:12] Jeremy: Yeah, and that’s exactly it. It’s, uh, controlling the things you can control. I think a lot of people try to control the things they can’t control, like the stock market or the, uh, next election. [00:07:20] Jeremy: But you can control your dreams. You can control whether you have planned or not. You can control how much you’re gonna spend and how much you save. I mean, you focus on the things you can control. I think you got have a lot better outcomes and a lot more fun doing it. [00:07:33] Joe: Well, you see a lot of people when they dig into retirement planning, you by the way, have a five simple step process. [00:07:39] Joe: We’re gonna go over this stackers, Jeremy and I, so that you get an idea of the five steps. But most people think, when I first opened this book, I’m like, okay, he’s gonna start with investing, right? Because you gotta invest for retirement. You don’t start there at all. Your first step is spend. Why do you start with spend? [00:07:59] Joe: I mean, don’t get me wrong. I’m a spender at heart, dude. Why do you start with spending money and not investing money? [00:08:05] Jeremy: We gotta figure out what you’re solving for. I’m kind of a math geek. I’m an Excel spreadsheet geek, and a lot of times you, you hit the solve for button. What are you solving for? Are you solving for a million bucks? [00:08:16] Jeremy: No, you’re solving for how much money do you need coming into your checking account? And there’s really two parts of it. One is the how much and the other part is the how long. So as you read through the book, you say, these are the five steps Jeremy put together. The next chapter says, well actually you ought start with step zero, which is figuring out how long you might be living. [00:08:35] Jeremy: Retirement, that’s a a number. That’s probably the most important number to your retirement math equation is how long will you be spending retirement. So getting that number correct is a big key part of it. But I start with number one of spending because that’s what you’re solving for. You’re trying to make sure you have the money that you either want to spend in retirement or maybe that you can only afford to spend in retirement. [00:08:56] Jeremy: You should know that ahead of time. [00:08:57] Joe: Can we start off with this how long idea, ’cause you said you need to get that number right, obviously. I mean, if I had a hotline where I could find out what that number is, but how do I kind of get in the ballpark, Jeremy, of scoping out the right. Timeframe ish toward how long I’m gonna live. [00:09:15] Jeremy: Yeah, so I call it the retirement longevity number instead of your life expectancy, because there’s two parts of it. It’s the beginning of your retirement, it’s the end of your retirement, and it’s easier to figure out the beginning of your retirement. On average, somebody retires three years earlier than they expected. [00:09:29] Jeremy: So if you’ve got your spreadsheet going right now, go ahead and make your retirement date three years earlier. On average, that’s when people retire. But the end of retirement, part of it is you don’t want to think about it. The other part is you think about it incorrectly. A lot of people feel like, okay, my life expectancy is a certain age, and that is like a certainty. [00:09:49] Jeremy: They think of life expectancy, like death certainty. That’s not the case. That is just the midpoint of all the probabilities that you might be out there for how long you might live. So number one, get that correct. Most people get that wrong, so go to a place like longevity illustrator.org to get the correct number. [00:10:07] Jeremy: Then have the correct understanding of this is just the midpoint. This is not the exact certainty time of it. And as you’re doing your planning, think about what happens if I don’t make it to that number? Well, how does that affect me? How does that affect my family? And then think about what happens if I do make it past that number? [00:10:22] Jeremy: Because half the time you’ll make it past half the time it’ll die beforehand. And you wanna think of the whole spectrum of how do my decisions affect me and my family if I’m before or after that number, that, uh, life expectancy number. [00:10:35] Joe: I love these what ifs, pondering these what ifs. Just because I feel like the longer we ponder it, the stickier our plan gets, the more we’re gonna stick to it. [00:10:42] Joe: Because we have thought of all the worst case scenarios. But I love this idea of just a getting a little thoughtful around what’s the timeframe, by the way, three years earlier? Why is that? Is it we’re not healthy enough disabilities? [00:10:55] Jeremy: It’s a lot of reasons. Center for Retirement Research in Boston College, they do these uh, numbers all the time. [00:11:00] Jeremy: Employee Benefit Research Institute, they do these studies all the time and just on average, you retire three years earlier than you expect. If you ask a 55-year-old, when do you think you’ll retire? They’ll tell you 65. But when you ask a 65-year-old, when did you retire? They’ll tell you 62. And I think a lot of it has to do a bit with your health bit with your parents’ health. [00:11:20] Jeremy: You’re 62, your parents might be 90 and you’re thinking, I’m gonna take the time to, uh, help them out. Also, social security kicks in at 62 if you want to, and that’s a big temptation. Another thing I find lately is you lose your job at 62 and you think, you know, I’d rather be retired instead of unemployed. [00:11:36] Jeremy: Or you get a new boss who’s younger than your kids and you say, that’s it. I can retire. I don’t wanna deal with this anymore. So you go ahead. Lots of reasons, but quite often, on average, you retire three years earlier. Than you expect. So you gotta be ready for it three years earlier than you expect. And if you do the math, you might figure out, wait a second, why do I need this extra three years? [00:11:55] Jeremy: I’ve made myself ready to retire three years early. Let’s go ahead and do it. [00:12:00] Joe: I love that thing about the bad boss and just the ability through savings to say, you know what? I’m done. I, I’m sorry, I’m not gonna play this game. You know, you were talking about starting off with spending. So we’re solving for how much are you gonna spend every year, which drives everything. [00:12:14] Joe: I like this approach so much better than the 4% rule. Now, what the 5.2% rule, Jamie, because I feel like Jeremy, that everybody starts off with how much can I spend? But if I start off with what I truly wanna spend, we go back to thoughtfulness in your financial plan again. Which I think again, makes your plan a ton stickier. [00:12:33] Joe: If I’m not just mindlessly spending money, I don’t know. Do you feel the same about the 4% rule that we shouldn’t be spending so much time on this number? [00:12:42] Jeremy: I like the 4% rule. And then it gives you a target like, uh, you’re 35, like I mentioned earlier. Okay, how much do I think I need to retire? Of course, the 4% rule ignores all kinds of things like social security and taxes. [00:12:54] Jeremy: And also I’ve just read the recent book, like you said, it’s a 4.7% rule, right? Right. And right in the book, uh, bill Bang and the, the author, the founder, discover of the 4.7% rule now says this is an ongoing thing. And that’s the whole point of what I set the planning together of. This is an ongoing thing where you should figure out ahead of time what is it you might be spending in retirement. [00:13:16] Jeremy: But then every year, take a look, what did I spend in retirement? What am I planning to spend the next year? You got a course correct along the way. I mentioned I’m a math guy. I’m kinda a cash flow corporate finance geek in a way. A lot of people think of it like, oh, I just need a hundred grand a year, whatever the number is. [00:13:32] Jeremy: No, you need different specific things like you need your lifestyle spending amount. What is it you’re, you’re spending on restaurants and having fun, and every year you need to figure out what your vacation budget’s gonna be. You need to take a look, what your tax might cost. You gotta take a look at your health insurance and your health insurance costs. [00:13:48] Jeremy: That’ll change over time, right before 65. After 65, your health insurance costs are wildly different, so you gotta really have some different budget line items in there. Then you can see, okay, how did I do on this budget for what I’m spending in general and what I’m spending on health insurance, travel house renovations, on taxes, things like that. [00:14:06] Joe: The people that were really good at saving and planning, do you find that they spend less money or more money than they thought they were going to when they were doing their planning? [00:14:16] Jeremy: In general, you spend a whole lot more. The first year you’re sitting around. The first year, you’re either taking all the vacations you’ve been planning to take, but you haven’t had the time to do it. [00:14:24] Jeremy: Or you’re sitting around your house and you’re looking around thinking, okay, I gotta update that. I’ve got the time to go do this project, that project. So you often spend more, I’d say everyone, virtually everyone spends more the first year. So that’s a bit of a shock. Like, wait a second, I’m spending more than I expected. [00:14:39] Jeremy: But what’s interesting too is that the people who are worried about, will I have enough? The answer is usually yes. If you had taken the time and you’re actually saving, the big problem oftentimes is you hit retirement and you realize you have more money than you needed. And it’s like, wait a second, what do I do with all this kind of money? [00:14:56] Jeremy: And, uh, that’s what the research rules, uh, shows, especially if you’re following this 4% rule. 4% rule is based off the absolute worst time in history outta the last hundred years. Okay, well, 99 times you did better than that. And so a lot of times if you’re trying to do like a Monte Carlo approach and you’re saying, I wanna get this 99% certainty that I’ll have enough. [00:15:17] Jeremy: Well, what that really means is 99% of the time you didn’t spend enough. You could have spent more. And I think that’s more of a failure than maybe it didn’t have enough throughout your retirement. [00:15:26] Joe: The second spot that you talk about, once we know what the target is, how much we’re gonna spend in retirement, step two, you call make. [00:15:35] Joe: What does make mean? What? [00:15:37] Jeremy: Yeah, just ’cause you stop working doesn’t mean you stop making money. And most everyone, nearly a hundred percent of Americans will have social security. I’m in Milwaukee, Wisconsin. There’s a lot of old line type of firms that still have pensions and so you might still even have a pension and you get these decisions, right? [00:15:53] Jeremy: You get to show up one time quite often to, uh, social Security or online and make that decision about social security and you never get to change it again the rest of your life. So it is not just a throwaway decision, it’s there to figure out how do I get the most out of Social Security? And especially with couples, a lot of people get that wrong. [00:16:09] Jeremy: There’s a lot of research that Dr. Larry Kotlikoff talks about how people in general, couples in general lose out on $180,000, uh, over the lifetime. Wow. Yeah. It’s a huge dollar amount, right? So these decisions, it’s like, uh, you got a hundred grand in your one account over there, your social security. Like you check a box, you could lose a hundred grand or 200 grand ’cause you check the wrong box at the wrong time. [00:16:30] Jeremy: So being thoughtful and thinking through what’s the best choice. With my social security is a huge part of it. That’s what you wanna do ahead of time. You wanna figure this out ahead of time and you don’t go with what your brother told you or the person who retired from your company about a month before. [00:16:46] Jeremy: He tells you. Those are all myths. I think you ought to base things off of math. I said, do math based retirement planning. Don’t do myth based retirement planning. Figure this out for yourself. [00:16:56] Joe: It’s funny, I’ve seen contradictory advice on when to take social security, so let’s go through a couple of these. [00:17:02] Joe: Number one is most of the CFPs, Jeremy, that you and I know say take it later because the fact that the math, the compounding on that number if you wait, is a much bigger number. So if you can, but then there’s this incredibly popular woman on TikTok. Immediately my eyes try not to roll, but she says, and I think she makes a good point. [00:17:21] Joe: She’s like, you don’t know how long you’re gonna live and when you delay, delay, delay, delay. She’s like, I say, take less and take it at age 62 because then you’ve got the bird in the hand. You know what you have and sure it’s a smaller number, but now it’s yours and you can pocket it. How do we begin to parse whether we should wait and go with that math-based approach because it’s more, or the woman on TikTok approach, A bird in the hand beats nothing later on. [00:17:45] Jeremy: Yeah. Well, it’s, uh, math will win. In my mind. I say, you ought to learn the math. Do the math and follow the math. Uh, but most people don’t even bother learning the math. How can you make this decision? You got actuaries involved, you got, uh, finance geeks involved. Like there’s a lot of stuff that goes into it. [00:18:00] Jeremy: I think you ought to break it down, make it a little bit more simpler, but before you make a decision, actually do some math. And the first step is to figure out what is your life expectancy. Most everyone gets that wrong, so go out and get it the correct number. Go to longevity illustrator.org. Going back to that same spot, you just go right there, figure out, uh, how long you might live. [00:18:18] Jeremy: A lot of people will take their social security early ’cause they say, well, you know, what are the odds? I’ll actually make it to this breakeven point. A lot of people actually have done the, the math and they figured out what they think is their breakeven point. A lot of times they hear 80. They say, uh, you know, what are the odds? [00:18:31] Jeremy: They throw their hands up in the air, like, what are the odds? Great, I’ll show you the odds. Go to that website and you’ll see the odds that you can make it to 80 or if you’re a couple and it’s the higher benefit that’s sitting around paying into your checking account, whether you’re here or your spouse is here. [00:18:46] Jeremy: So it’s not the odds of how long you live, it’s the odds of how long one of you might live. And when you run the numbers, quite often those odds are like 70%, 80%, 90%. So don’t just throw your hands up in the air, like what are the odds? I’ll never be able to figure it out. You can figure that out in about two minutes and then you’ll know the odds. [00:19:02] Jeremy: And those odds might be 80%, 90% for a couple. It’s like going into casino where you win 90% of the time. You would never walk out. But oftentimes people are going into social security, they’re walking in saying, well, I’m worried about if I don’t make this uh, thing work and it’s only gonna happen 10% of the time. [00:19:19] Jeremy: And then they file for social security too early. And you might wanna file for social security, but actually. Do the math first. Figure out if it’s the right thing for you. [00:19:27] Joe: I’m, uh, stacker’s going to link to when Ted Dig Smith was on the show and Ted Jeremy was a guy who’s really passionate about how we should teach math and the subjects we should teach. [00:19:38] Joe: And one is probabilities. Like there’s a bunch of stuff we learned in math that we don’t need, but understanding probability better. To your point earlier about what’s the math that we can figure it out fairly quickly with just a couple websites. That’s the math around social security. You mentioned that in some legacy cities, you’re a Milwaukee guy. [00:19:57] Joe: I’m originally a Detroit guy, lots of pensions still in Detroit. For somebody that has a pension available and hasn’t yet looked into the different pension options they have available, how do I start to parse out what the best pension option might be for me? [00:20:10] Jeremy: Yeah. The first step is to actually just get the info. [00:20:12] Jeremy: Most people when they come to me, they say, I figured out my pension. I looked at the info of what if I take it today or what if I wait one year and then take it a year from now? That’s not all the info. I’ve got several clients at, uh, some big name firms in Wisconsin where you could retire today at 55 and you could wait to take your pension to age 70. [00:20:34] Jeremy: I’m not saying you should wait to take your pension to age 70, but if there’s 15 years of options, I’d want you to look at all 15 years of options before you make a decision and you might go through and say, yep, it’s the right choice. I’m taking the pension right here at 55. But quite often you’ll see, wait a second, there’s some weird things that happen with this pension. [00:20:52] Jeremy: If I wait this extra year, I make 10% more. I’ve seen it where you wait one extra year, you make 16% more. Right? That’s double what Social security is gonna increase you over one year and until you know the math, you don’t know what the best thing is for you to do. So it’s not with the pension. A lot of people, I, I say they make two mistakes. [00:21:09] Jeremy: The first is what I just mentioned, where they just think the only options is I, I quit today on ticket today. Or I work one more year and I take it immediately. The option is you stop today or whenever you wanna stop. But what if you wait a year? Wait a year, wait another year, keep on going with your pension. [00:21:24] Joe: Could be a whole separate income stream than when you retire. [00:21:27] Jeremy: Yep. That’s exactly it. And until you figure out all your options, you don’t know which one’s gonna be the best for you. The other thing that happens with the pensions, it’s like, oh, I had this old pension from way back when, so they just. It’s kinda like throwaway money. [00:21:39] Jeremy: They just click a box, whichever it is. Oh, let me take the monthly amount or, or let me take the lump sum, big payment upfront out of it. ’cause they, they think it’s kinda like throwaway money. I wasn’t expecting that. Well, I’ve seen them worth 50 grand, a hundred grand, 200 grand of this pension. And if you can check a box and make it worth more or worth less, I’m guessing you’d rather take a few minutes, do the math and check the right box to give you. [00:22:02] Jeremy: 50 grand, a hundred grand more instead of doing the opposite. [00:22:05] Joe: And it’s funny stackers because in the past when I would do this way back when, Jeremy, and it sounds like based on your answer, it’s still the same. You and I would love to tell people, Hey, this option’s right all the time. But the math from company to company was grossly different. [00:22:20] Joe: It sounds like it’s still the case. [00:22:21] Jeremy: Yeah, it’s different from company to company. It’s different from year to year. A lot of the pension math is based on current year interest rates. It’s like they calculate it in a negotiation a couple years ago, but then they’re applying a formula based on uh, this year’s interest rate. [00:22:35] Jeremy: So you’ve gotta take a look to see is it worthwhile to take it now or take it later? Is it worthwhile to take the monthly amount or take the lump sum amount? You don’t know until you do the math. I think you ought to do the math part of it. And there’s also one thing to keep in mind. When a financial advisor is telling you to take the lump sum pension, they usually get paid on that. [00:22:53] Jeremy: There’s perhaps an annuity or they’re managing more of your money. When the financial advisor says, yeah, I’ve done the math and take this pension as a monthly amount, then. If they’re not making any money off of that. And so just keep in mind, there’s often an incentive if the financial advisor is telling you to take the lump sum and invest it, that could be the right case. [00:23:11] Jeremy: But know that there’s a financial incentive for them to suggest you take the money out as a lump sum and invest it with them. [00:23:17] Joe: I think a great piece to start with this math and whether your advisor is just trying to manage more of your money, Jeremy, and is like, Hey, bring over the lump sum. That’d be great. [00:23:27] Joe: Is what rate of return do I need to get on that money to equal this monthly payout? And if it seems fairly easy to beat, then certainly take the lump sum. If it would be a stretch to beat it, well then why would I risk money in the financial markets? At least that’s the way I see it, that I would need to know at the very least, that calculation. [00:23:50] Jeremy: Hey, figure out what’s that return calculation. But it’s also been a preference. You might be someone that wants to take a chance at beating what the pension might be promising to you. Maybe you just say, I like that solid monthly amount coming in. There’s a, it’s really a preference of what you, uh, prefer. [00:24:06] Jeremy: It’s funny though, I talk to some people sometimes and they say, I want that lump sum, uh, of money. And I say, what are you gonna do with it? I’m like, I’m gonna go put it into the market and, uh, do like a 60 40 portfolio and see how it goes. Well, if you look into the pension, they’re invested in like a 60 40 portfolio without any management fees. [00:24:22] Jeremy: So they’re kind of doing it already for you on your behalf. So it is interesting, uh, what are you gonna do with the money? And it, it comes down to the preference, but also you gotta do the math first. You don’t know whether you’re making a good decision or not till you’ve thought things through and, and you see those numbers in front of you. [00:24:37] Joe: I think though, part of evaluating that advice though is to begin with that number. What’s the rate of return that I would need? I like it because then I’m getting a little bit of a, of an idea about whether this advice makes sense or not. Step three, so we, we went through, we start off with how much money we spend. [00:24:52] Joe: Second, we look at our stream of incomes coming in. Third is the word keep. What does keep mean? [00:24:57] Jeremy: Yeah. You wanna keep more of your hard-earned money and you’ll be paying taxes in retirement. You’re paying taxes right now, most likely. And what most people don’t realize is you hit retirement. You have far more control over your tax situation than needed beforehand. [00:25:12] Jeremy: You’re working, you get your W2, you give it to your tax person, you plug it in yourself. And there’s maybe some little things you can do on the margins. HSAs or IRA contributions, there’s like a little bit you can do. You hit retirement and everything just opens up. You’ve got all these different accounts and you’re not being forced to take out an account from one or another. [00:25:30] Jeremy: You could take money from your traditional account or your Roth account or your brokerage account or your savings account. Those are four different accounts and four different tax situations, and you get to choose which accounts you take out the money from. When you get to choose, do I take money out in December or January, and that’s two different tax years, there’s all these levers you get to pull where if you are thoughtful on when do you take the money out and when do you pay the taxes on it? [00:25:54] Jeremy: I found quite often you can lower your lifetime tax bill and hey, if you’re paying less in taxes over your retirement, that’s just more money that you get to keep. [00:26:02] Joe: I feel like this is a spot, Jeremy, where for our younger stackers you can set yourself up really well with a little bit of tax diversification ahead of time. [00:26:12] Joe: Like what kind of an account as a CFP do you wanna see people have? What type of tax diversification do you wanna see people have if they’re doing this the right way to give themself the most flexibility in retirement to maximize those tax brackets? [00:26:25] Jeremy: Yeah, I like what you’re calling it, tax diversification. [00:26:28] Jeremy: It’s not just about different stocks and bonds, it’s how will you save or pay taxes now and how do you save or pay taxes later on? ’cause you don’t know what the next political tax law is gonna show up as. And I see so many people that hit retirement. They’re 62 years old, they’ve got 99% of their money in a traditional 401k, and they loved paying less taxes back in the day. [00:26:48] Jeremy: But they’re saying, I’ve got a huge problem. I wish I’d done the Roth IRA earlier. So as you’re saving, quite often it’s the Roth IRA, the Roth 401k. If you can put money into it, it’s helpful. To have this ability to take money out later on. You’re 60 plus years old. You’re in retirement. You wanna take out. [00:27:05] Jeremy: 30 grand for a new car, a new Windows, new driveway, and all you take out is 30 grand from the Roth ira. You don’t have to take out like 50 grand extra or whatever the number is to pay the taxes on it. So having Roth IRA accounts gives you the most flexibility later on. Of course, you have to pay the taxes right now, and so that’s why you maybe have that tax diversification. [00:27:25] Jeremy: Maybe you do a traditional 401k and then you do the Roth IRA. Outside of that, just to have some diversification, some different options. [00:27:32] Joe: Alright, let’s talk for a second to our 25-year-old stackers listening. Is your bias then toward Roth if possible? [00:27:40] Jeremy: That’s the bias. Theoretically, as a 25-year-old, you’re making less money in your income than as a 55-year-old. [00:27:45] Jeremy: So theoretically your tax rates are lower now than they are later on. That might not always be the case, right? And you might be on the, on the coast and you just strike it rich with an internet startup. Uh, so it’s not always the case. The nice thing about rules of thumb is that it kind of gets you pointing the right direction, but you gotta wanna think about how it applies to you specifically. [00:28:02] Jeremy: But that’s the theory is you’re younger, you haven’t grown as much into your career, so your income’s got room to grow. Your taxes are likely to gonna grow in the future, and you’d rather have the tax free money later on. You don’t mind paying what’s likely a, a lower tax rate now by putting the money into the, the Roth IRA. [00:28:19] Joe: How much do you worry about tax on Medicare or tax on our Social security or Irma? [00:28:27] Jeremy: You’ve gotta include that in your planning. So many people, uh, don’t even bother to do the tax planning, but they do the tax planning as if, like, lemme just look at the bracket. All right, I’m the 22% bracket, I’m the 24% tax bracket, I’m the 12% tax bracket. [00:28:42] Jeremy: But there’s so many other things that come into play. If you’re below 65 and you’re not working, you need health insurance. And usually that’s coming from the Affordable Care Act. That’s a tax cost if you have more income, but it’s not gonna show up in your tax bracket. And when you’re past, uh, 65 and you’re on Medicare or you’re past 62 or whatever age that you file for Social security, your decisions, uh, which of one of those accounts do I take the money out from will affect how much your social security gets taxed. [00:29:10] Jeremy: It’ll affect whether you pay extra. Parts of your Medicare costs with that Irma surcharge, they call it. So you’ve, you’ve gotta plan it out. And oftentimes you look at it and say, eh, it’s not too big of a deal. The Affordable Care Act, though, that is often a, a big deal. ’cause a lot of times, and we’ll see how the tax laws come about right now, but, uh, currently at the end of 25, you starting to 2026, there is now this Affordable Care Act cliff, which they used to have where you, you hop over by $1 and your subsidy went from, uh, 15 grand to zero. [00:29:41] Jeremy: Right? Wow. That’s a big deal. The, uh, the Irma and the social securities, you wanna know about that. You wanna plan for it, but it’s kind of a, a marginal cost. That’s a huge cost right away if you didn’t think about the Affordable Care Act. So you, you wanna plan these things out. It’s, it’s not just your tax bracket. [00:29:55] Jeremy: There’s all these things that come into play, like the Affordable Care Act, subsidies and Irma and Social Security. That’s a big cliff. Yeah, it’s a big cliff. It, that’s, that’s why they call it the cliff. You, you know, you make a little bit more and you lose a little bit of subsidy, it, it’s natural. Then boom, there goes 15 grand just by making $1 extra. [00:30:11] Joe: It’s funny because we started off with spending and then streams of income and then tech strategy. We haven’t talked yet about investments, and I led off by saying, of course we’re gonna start with investments. Investing is number four. Earlier in this project, I wanna read everybody just a piece that I like from the book you write. [00:30:29] Joe: I remember it like it was yesterday, Monday, March 9th, 2009. I was getting calls all day from worried clients. The stock market had been dropping for the past year and a half that day. The market wasn’t down that much, only 1% at its worth only 1% that day, living the dream. I remember those days. By the way, this was the end of my career in financial planning, but it was just another down day and a seemingly endless series of down days. [00:30:53] Joe: The s and p 500 had dropped 12% over the past. Two weeks. The US stock market was now down a total of 57% since the October 10th, 2000 seventh high point. So you get this call, you’ve been calling a bunch of people, you’ve been talking people day after day off cliffs, by the way, I started shaking ’cause I remember these days reminding people they had a financial plan. [00:31:16] Joe: But a guy named Gary called you. Can we talk about Gary for a minute? Jeremy? [00:31:20] Jeremy: Yeah. Gary’s, uh, interesting. He’s like several people I’ve, uh, talked to over time, but he’s the one that, that just really sticks out to me. ’cause a year earlier he said, I wanna retire in a few years. Let’s set up my investments. [00:31:33] Jeremy: I’m a big fan of this idea. They call a bucket strategy. Let’s have short term money, let’s have some long-term money. And of course the market down then. So, you know, spring of 2008, the market’s down like 10%, 15%. It was down a little bit. And I said, we like to do income buckets. Let’s set up some money for the short term. [00:31:48] Jeremy: Let’s set up some money for the the long term. And he said, that’s a great idea, but I’ll wait till the market comes back. A year later, the market didn’t come back up. It’s down like 40% now, down 50% from the absolute top point. And so he was calling every day saying, I can’t let my money drop further. I can’t let my money drop further. [00:32:08] Jeremy: And I was saying, well, when do you need the money? Well, it’s like a year from now. You know, it’s down the road. Well, if you don’t need the money today, why are you getting outta the market today? And then finally he just couldn’t take it anymore. The market was down. He said, uh, I gotta get out, sell everything to cash. [00:32:22] Jeremy: And I did. You know, that’s his instruction. Sold everything to cash. I tried for weeks to convince him not to tried that day to convince him not to. He sold everything to cash. I hung up the phone, I turned to my business partner at the time. I said, this is probably the bottom, Gary, uh, threw in the towel. [00:32:37] Jeremy: And unfortunately I was correct. And years later, Gary still had his money in cash. He didn’t invest the money back into the market. He didn’t even take the money out ’cause he, he didn’t need it. And it’s all about when it comes to investing, knowing when do you need the money and setting things up if you need money in the short term. [00:32:53] Jeremy: Use short-term investments if you need money, long-term use, long-term investments. And he was conflating it too. Like so many people do. They think I need some money soon. So it’s, it’s in the, the long-term stock market type money or I need money way down the road, but I can’t afford to lose it. So lemme put it into the bank. [00:33:08] Jeremy: It’s all about your time horizons. When do you need the money? That’s the first thing you think of with, with investing. [00:33:13] Joe: How many times have you heard, yeah, Jeremy, but this time’s different. [00:33:18] Jeremy: Yeah, it’s too often. Unfortunately. I’ve got a similar story with somebody in, in COVID where the market’s dropping, you know, 5%, 10%, 30% eventually. [00:33:26] Jeremy: It’s funny and bad that it was exactly the same thing, where a different person, he called on that Monday of, uh, COVID in late March. He said, I just can’t take it anymore. I’ve gotta pull out, uh, move it to cash. And I did. ’cause that’s what he instructed me to do after weeks. And, you know, trying so long that day to, to convince him otherwise. [00:33:45] Jeremy: And I called another business department my time. I said, guess what it, this guy pulled out of the market. It’s. Probably the bottom and the next three days, the stock market went up 20% fast a year. Yeah, very fast. Three days it went up 20%. And two, three years later, uh, this individual around COVID time still hadn’t taken the money out because he kind of conflated the short-term market moves with what am I gonna do? [00:34:09] Jeremy: It’s like, oh, the market drop 10% yesterday, last week. It’s gonna do that every day for the rest of the time. No, that’s, that’s not how it works. [00:34:16] Joe: This goes back again though, to number one, which is start off with spending. How much are you gonna spend? Because now I know how much I need in that short term bucket. [00:34:26] Jeremy: Oh, you need a 30 grand out next year. Well, why are we taking the whole half a million dollars and throwing into cash? Well, maybe you move 30 grand to cash and say, okay, I’m, I’m good for the next year. Let’s leave the money invested and, and see how it grows. But if you don’t know what you’re solving for, if you’re solving for, I need this number to say a certain thing on my statement, uh, then yeah, every single up and down, which happens milliseconds all day long is gonna affect you. [00:34:49] Jeremy: But if you know what you’re, you’re solvent for. Then, you know, okay, I need this X amount set aside for the short term. And when the stock market drops, it’s no fun. But then you look and say, oh, I wanted three years of money set aside, uh, in cash. And there you go. I’ve got it. It’s no fun with the market up and down, but I can afford to let it come back up again. [00:35:08] Joe: I did like, as an advisor, you tried to find a middle ground, which also was absurd because if you start off with when you need the money and work backward, you still wouldn’t do this. But you even tried to tell Gary, Hey Gary, you’re not gonna need this money right away. He wouldn’t listen. But then you said, why don’t you just take, then half of it, it’s way more than you’re gonna need over the short run, but why don’t you just move half of it to cash instead of all of it? [00:35:30] Joe: And Gary still wouldn’t do it. Jeremy, this story hit home with me. ’cause I had this with a family member, which I was always told during my career, don’t work with family members. And it was always true. By the way, guys do not work with family members. And I had this family member that was like, what do he keep saying? [00:35:45] Joe: The horse has left the barn. No, the horse has left the barn. We gotta move it all. We gotta move it all. I’m like, you’re about to put the horse out of the barn. It will go out of the barn if you move at all. And he moved at all. And he locked in all these losses. And I still, I’ve been a financial planner and forever. [00:35:58] Joe: And I still get angry, Jerry, I still get angry about that. Oh, it’s so frustrating. So begin with the end of mind. Begin with the amount of money that you’re gonna spend. That’s exactly it. What’s the fifth step? [00:36:10] Jeremy: Fifth step is what is it you leave behind? And sometimes you leave behind some money. Oftentimes you leave behind a mess because you haven’t planned for things ahead of time. [00:36:18] Jeremy: And it’s not just the idea of the estate planning and how much money you’re gonna leave behind, it’s also where the risks that could derail your retirement, right? You do your Excel spreadsheet, everything looks great when every single box shows the exact amount of inflation and stock market returns. Uh, but what if inflation in the stock market doesn’t do what you thought? [00:36:36] Jeremy: What if your health changes in a way you didn’t thought, uh, you didn’t think was gonna happen? And so as you do your planning, yes, set things up, it’s gonna work out pretty well. Let’s start thinking of the things that might not go so well. Uh, one thing that might derail the train there for your retirement is, uh, you live longer than you expected. [00:36:53] Jeremy: Or what if you. Don’t live as long as you expect. How did your decisions with social security and how much money you’re gonna spend, how did that change if you didn’t make it to the exact number? A lot of people think like, I’m hitting this exact number and that’s it. And they plan out, I got the 20 years on my spreadsheet. [00:37:09] Jeremy: Well, what if it’s five? What if it’s 35? Think of those different things that could change your retirement. And of course, uh, especially if you live longer, your health might change and you’ve gotta think through what’s your plan? In case my health changes in retirement, part of that’s the health insurance you choose. [00:37:25] Jeremy: Part of that’s maybe having some sort of long-term care planning doesn’t mean you have long-term care insurance just means you have a long-term care plan. Think about where are you gonna get that care and who’s gonna provide that care for you, and how are you gonna pay for that care? You wanna plan these things out ahead of time. [00:37:40] Jeremy: That’s all the kind of the, the risks that can hit your retirement. And of course, hopefully things still go well and then you leave some money behind and you’ve got some documents you wanna put together. You wanna take care of the people you leave behind. [00:37:52] Joe: That catastrophic illness planning and that contingency planning. [00:37:56] Joe: When you get to that point in your plan, just when those things inevitably hit and you know that you already thought about it five years ago, 10 years ago, 15 years ago, you already have a plan in place. Like watching that plan spring into action with people when I was an advisor, was always, so fun’s not the right word. [00:38:11] Joe: Uh, comforting. I think comforting was the word. ’cause you’re like, you know what? We don’t have to worry about it now. ’cause we already planned, here’s what our strategy is and it’s still valid today. It’s funny because when it came to long-term care, what drove me crazy when I was a financial planner was people would go, well, yeah, I decided against the insurance. [00:38:29] Joe: And you said this earlier, Jeremy. I was like, great, what’s our plan? I don’t care about the insurance. What’s our plan? They’re like, yeah, I don’t know, but I’m not gonna buy the insurance. Great. I don’t care. What’s our plan like getting around whether you’re gonna buy the insurance or not is fine. It’s what are we gonna actually do, which is far more important. [00:38:46] Joe: I think the insurance industry doesn’t want you to think about that. They want you to think about yes or no on the insurance where you’re talking a much, much bigger rubric. [00:38:54] Jeremy: Yeah. You say what the plan is and you might go through and say, I want the insurance. Well, uh, work with an insurance broker you trust to go find the best insurance for you. [00:39:01] Jeremy: Or you might work through and say, I don’t want the insurance. Uh, in which case there’s a, uh, strategy that Christine Bins put in her book, how to Retire, where she calls a long-term care fund. Perhaps you have $1.2 million save for retirement and you decide, I don’t want it to get the insurance, but I wanna earmark 200,000 towards long-term care expenses in the future. [00:39:21] Jeremy: And then I’ll just base my planning on the million dollars that I have here. So you get this kind of extra account on this side where if you need it, you’ve got it. And if you don’t need it, well they’re just extra money that might help out. Your surviving spouse might, uh, help out your kids later on down the road. [00:39:36] Jeremy: You’ve actually put a plan in place. It’s not, I just sat against the insurance, so I’m just gonna stick my head in the sand. Uh, I don’t have a plan in place. If you say no to the insurance, fine. What’s your plan then? [00:39:46] Joe: Jeremy’s new book is called Retire Today. Create Your Retirement Master Plan in Five Simple Steps. [00:39:51] Joe: I’m so glad you could go through a couple of the strategies in each of these five sections. Obviously the book is what, 225 pages long, so we’re, there’s no way that we’re gonna do ’em all on our show, but where can people get it, Jeremy? [00:40:05] Jeremy: You can find anywhere you, you buying books, but, uh, you could also go to my website, jeremy kyle.com, J-E-R-E-M-Y-K-E-I l.com, and there’s a link there for you to get the book. [00:40:15] Joe: I would be ostracized by our stackers if you didn’t tell people what’s coming up on the podcast too, on the Retired Today Podcast. [00:40:22] Jeremy: Yeah. So retired today is a podcast I’ve had for six years, used to be called Retirement Revealed Change the Name to Retire Data to match the book. If you go to the podcast right now, you’ll see, hear me going through each of the steps and details. [00:40:36] Jeremy: But coming up pretty soon is something I call a true retirement story. I think it’s good to know what, uh, retirement looks like from somebody that’s not a financial advisor. It’s not even a podcast or somebody that’s a, a true retiree that’s telling you what retirement is life. So they got true crime stories out there. [00:40:54] Jeremy: I’m bringing it to retirement, true retirement stories. So you see, uh, what life’s like on the other side. [00:40:58] Joe: That’s awesome. We love those stories like case study time. Yeah, great stuff. We’ll link to all of that, the book and the podcast in our show notes. Jeremy, thank you for mentoring our stackers today. I super appreciate you taking the time, man. [00:41:11] Jeremy: Glad to be here, Joe. [00:41:16] Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and man, how awkward. Accidentally gave a free show to the lady next door until I realized the blinds were open in my trailer next to Joe’s mom’s house. I do believe she got an eye full because I just got a cryptic note saying she wanted to pay me some money and what you’re thinking and no, I’m not creating a spicy little page anytime soon, stackers. [00:41:40] Doug: Although you can listen to my voice and just imagine how, what? What? Okay. All right. I’ll just do the trivia, but they love my voice. These guys have no idea how hard it is being this beautiful. Weird connection coming. Just wait for it. It’s coming. Okay. Yet another beautiful person, there’s more than just me, made history today when her photos appeared all natural in the very first issue of Playboy, way back on today’s date in 1953, they were photos she’d taken back a few years earlier when she was a struggling artist, kinda like I am right now. [00:42:19] Doug: Hey, maybe I should do this trivia segment. A little stripped down, huh? Nope, not a problem. Bring him to the show. Can’t see below the desk. You don’t know. Maybe I already am. So, who was the one time struggling actress who appeared in issue number one of Playboy? I’ll be back right after I find out just how much this neighbor lady will give me if I show off my ankles. [00:42:43] OG: I got great ankles, man. More like ankles. [00:42:54] Doug: Hey there, stackers. I’m Mr. Texarkana Ankles 2025, and guy who’s more than a little confused. Joe’s mom’s neighbor, Doug. Okay, get this. The neighbor lady who saw me with the blinds open is gonna give me money, but only if I. Keep my shirt on and never take it off again. Wow. I must have really rocked her world, huh? [00:43:16] Doug: Well, to earn that five bucks, I, I just have to wear this shirt for six months. Straight. Five bucks. People are paying for anything these days, but Playboy paid one future star a lot of money to appear in issue. Numero uno of their new magazine back in 1953. Which star was it? Whose photo from just a few years earlier? [00:43:37] Doug: 1949 were used in issue one. The answer None other than Marilyn Monroe. And now here come two guys who love to get naked and intimate with their money Talk. Joe and og. [00:43:51] Joe: Yes, we do. Let’s get down to what’s real. And Doug, glad you’re gonna earn five bucks, I think for all of us. We’re happy to see that shirt. [00:43:59] Joe: Stay on. [00:44:00] Doug: I look great. And so, you know, there are times when, when clothing is sexier than not clothing. I think that’s really what that neighbor was saying. See you [00:44:06] OG: all the time. Right? [00:44:07] Doug: Every time we see you we’re like, clothing is better than done. It looks good on me, man. [00:44:12] Joe: Yeah, it is great. Thanks to Jeremy for coming down to the basement and I thank OG just to shine the spotlight a little longer. [00:44:20] Joe: Hard to invest money when you don’t know what you’re investing for. Almost goes back to John’s call from Monday when he was talking about different financial advisors to manage his money and they all had different ideas. Mm-hmm The ideas really come together better. If you start with how much money do I think I’m gonna spend? [00:44:38] OG: We look at that. As you know, there’s really four different buckets every, every year that you can put money in. You can, you can pay your income taxes, you can save it, you can spend it on debt, and then you can spend it on everything else. If you just break your spending down into those four buckets, it becomes pretty clear to see what the everything else bucket is. [00:44:54] OG: And if you still got some debt, you know, coming into retirement, you can add that. But taxes are a function of where the money comes from. So that’s the calculation on the backend. A lot of times people look at their gross income and go, well, in retirement, you know, I make 150,000, so I guess in retirement they need 150,000. [00:45:10] OG: It’s like, well, you only spend 65. The rest is savings, taxes and debt payments. So having a clear understanding of what your budget is going in makes everything else flow from there. [00:45:21] Joe: Yeah. The more you know when I’m going to spend a dollar, the easier it is to invest for that dollar, because much like in a lot of sporting events, the game is not to do the fantastic play. [00:45:34] Joe: The goal is to just not mess it up. Keep the, if you’re playing down golf. Yeah, if you keep, if you’re playing golf to stay outta the sand trap, stay away from the trees if you’re, yeah, if you’re a football player to not football or if Doug’s playing, [00:45:46] OG: stay outta the fairway. [00:45:48] Joe: Whatever makes you happy. I’m better from the rough. [00:45:52] Joe: Speaking of sports, [00:45:53] OG: especially putting, [00:45:55] Joe: speaking of sports, uh, stacker. Steve sent us something and said, Hey guys, football season’s here. And I know that it doesn’t have a lot to do with money, but this has a ton to do with your love in quotes of the state of Ohio, which apparently is shared by comedian Greg Warren. [00:46:13] Joe: A funny story, by the way, Steve, is that, uh, I took Cheryl to see Leanne Morgan in Shreveport a few weeks ago, and I was pleasantly surprised when Greg Warren, the guy we’re about to hear was the opening comedian, and I love this guy. So Steve, I was glad that you sent this, but Greg Warren talking about the state of Ohio. [00:46:33] Joe: I love the people of Ohio, [00:46:34] bit: but. Like the Buckeye fans, I don’t like, they’re just, they’re, they’re, they’re, you know, they’re, they’re obnoxious. I mean, anytime you’re in a room and you say anything about sports, half the people go, oh, h oh, like see, see io. See, see, it takes two of these idiots to spell their state. [00:47:05] bit: Hey, how do you spell the place where you live? Well, usually I work with a partner. Hold on one second. Jimmy, come here. They want us to spell the state. [00:47:15] OG: Takes two people for all four letters. We were driving down the road, uh, stopped at a stoplight. And you know, sometimes you hear a porn blow or like beep beep and you just kinda like go, oh, light’s still red. [00:47:27] OG: You know, it wasn’t for me. And then I hear, beep, beep, beep. Okay. Still not for me. Honk, honk Kong, honk, honk, honk, ho, honk. And finally I realized this guy next to me, I look at him, I go, what? Forgetting? I’m driving my wife’s car that’s got a Michigan plate, like a Texas plate, but it’s a block m and the guy next to me just does the big OH and uh, I gave him the IO in a single middle finger, double Bird [00:47:53] Doug: in America sign, which he got the IO [00:47:54] OG: version. [00:47:55] OG: He got the Michigan version of the IO right back to him. So we had a good chuckle. [00:47:59] Joe: That’s how Michigan, Ohio State fans say, I love you. That’s your lovely witch. That’s, we say, [00:48:03] OG: can’t wait to see you in November. Hope it’s a good game. Yeah. Good luck to you. I hope everybody has fun luck to you. [00:48:09] Joe: You’re number one in my book. [00:48:12] Joe: Steve, thanks for setting that along. The very, very funny comedian Greg Warren there. Let’s move on to our headline. [00:48:20] headlines: Hello Doling. And now it’s time for your favorite part of the show, our Stacking Benjamin’s headlines. [00:48:26] Joe: Our headline today comes to us from the website Seeking Alpha. Uh, boy, you know, in the headline all year this year, guys, we’ve been reporting on the SEC approving private investments in your 401k and it took almost, no, it took almost no time at all for this quote, goodness that we’ve been reporting on. [00:48:49] Joe: And by air quote, you gotta hear the dripping sarcasm here stackers these wealth management firms to jump on this. Seeking out for reports, Goldman Sachs t Rowe Price Plan to offer new alternative investments for wealthy clients by 2025 and M for retirement accounts starting in 2026. So they’re gonna roll it out to wealthy people in 2025, and the rest of us, they roll it out early next year. [00:49:13] Joe: This is according to Reuters. The news comes, as Goldman Sachs said earlier this month it plans to acquire up to a billion dollars in t Rowe Price. Common stock equaling a stake of 3.5% in TROW as part of a collaboration agreement. The Alliance was set to focus on offering public and private market investment products for retirement and wealth investors don’t know why. [00:49:39] Joe: I think we need private equity inside our 401k. There is nothing stackers. We don’t, there is no goal that this is going to help you reach, that you can’t already reach without private money. Private money’s gonna put more money into Goldman Sachs. They can mean [00:49:59] OG: Goldman Sachs. I mean, there’s a time and a place for illiquid investments and for what this goes after, which is smaller micro companies, you know, an aggregate type of deal. [00:50:10] OG: But that’s just not for the normal investor, you know, a regular investor. Because think of it this way, if you base everything based on the concept of treasuries or your bank account, right, the concept of risk-free rate, or if you just wanna add the s and p to the calculation and say, you know, I know with a high degree of certainty that I can get 10% a year if I invest in the 500 biggest companies in the United States now it’s not gonna be 10% linearly every year. [00:50:40] OG: You know, there’s some volatility there, and I’m willing to accept that volatility that some years it’s plus 30 some years it’s minus 30, but it’s gonna average to 10. I’m okay with that. And you base everything off of that. Now you’re gonna say, I’m gonna take some money and I want it to be crazy illiquid, or I want it to be focused on this really esoteric type of thing. [00:51:01] OG: What kind of return are you going to need to accept the fact that the volatility of that is so much more? And the way that I would think about this is you’ve got the 500 biggest companies in the world. You get 10% a year with a known range of returns, right? Plus 30. Minus 30, let’s say with the occasional outlier twice in your lifetime of a minus 40, minus 50. [00:51:25] OG: Okay? So that’s your baseline number. That’s your baseline acceptance of, of ups and downs in the market. And this is your retirement money. And so your brother-in-law shows up and says, I have this great idea. I make amazing ice cream. You know it, you’ve had it. We make the little batches in the kitchen. [00:51:41] OG: It’s fantastic. Everyone loves it. I think I should start an ice cream business. And I want you to be the first investor. I’m gonna invest some, you invest some, and I can guarantee you. Uh, 10% return. What are you gonna say about that? You’re gonna say, no way, dude. Like, if I’m investing in your company, I know I already know what I have to do to get 10% right. [00:52:01] OG: To get 10. I need to invest in the 500 biggest companies in the world. The most productively managed, the most expertly driven companies that have ever existed. And I get 10. And no offense to you in your fine ice cream making, who’s [00:52:16] Joe: gonna run, who’s gonna run a better company? Your brother-in-law. Yeah. [00:52:20] Joe: With a good idea. Who’s never run a company before, just makes good ice cream or Coca-Cola like, right? Which one is a machine. [00:52:27] OG: And not even Coca-Cola, but the aggregate of all the Coca-Colas that ever existed and ever will exist, you know, all the most well capitalized companies. Okay, so what kind of return do you have to have to accept the risk of that small, small, small company investment? [00:52:43] OG: Would you do it for 11? Probably not. Would you do it for 12? Probably not. We should do it for 15, 20, 25. Like you have to have so much higher return potential because your variability doesn’t go minus 30 to plus 30 anymore. It goes zero on one end, the ice cream shop fails and there’s no money. I think I gotta double my money. [00:53:06] OG: Well, yeah, or, or more. You know, we turn into the next Ben and Jerry’s. Right. So those are the two extremes. We’re Ben and Jerry’s in 50 years or I’m out. So what kind of annual return do you need? Somewhere in the middle. And the same thing is true with a lot of this private equity stuff. And I’m not saying that it’s not productive, I’m saying that it’s illiquid. [00:53:23] OG: It’s hard to get your fingers on how it’s being managed. And for some people, this rate of return and volatility is acceptable, but probably not for the vast majority of stackers. [00:53:34] Joe: I have, I’ve come down as longtime stackers know on liking some of these private equity investments. But I think it’s fun with your sandbox money, and I think these are compelling stories, but inside your 401k, you’ve gotta disregard the sales pitch. [00:53:49] Joe: Well, at the very least, look behind the sales pitch. So I’ll give you two that in the past I’ve said that I’ve liked. I’ve liked Masterworks in the past. This is where you buy artwork, you’re actually buying into an actual painting, and then the value of that painting hopefully goes up while you hold it and then you sell it. [00:54:06] Joe: One thing about Masterworks that when you look past the sales pitch and what they do, so the first thing is the sales pitch. I love that sales pitch. That’s great. You know what I don’t like about Masterworks og, which is why it’s a sandbox thing for me and not more than that. Look at how much it costs the people at Masterworks to do their job. [00:54:24] Joe: The huge amount of money they have to make for them before they make any money for you. And the fact that you’re investing in one painting now, they’re good at it, but you’re investing in one painting and you’re not gonna have any liquidity until that painting comes to life. Like is it really, is the juice gonna be worth the squeeze? [00:54:42] Joe: No, I just think it’s fun. I think it’s fun. Which is why it’s Sandbox Money Acre Trader. We did an episode with the creator of Acre Trader about how we created that company. These people invest in farmland. Again, your money is going into. The dirt in the ground, you’re not gonna get your money back until that sale is complete. [00:55:03] Joe: Which, how many years in the future is it gonna be until that happens? And imagine in your 401k the amount of money that it takes to invest in these investments. There’s often a very sizable minimum investment to get into these things. You put 25 or 35, $40,000 of your money into the ground, and it turns out that there’s some, uh, environmental issue, let’s say. [00:55:23] Joe: Who knows? But when you get specific like that, it can be awful. So I think people are gonna be enamored by the sales pitch. And listen, Goldman Sachs and t Rowe Price, they’re fantastic at sales pitch. They’re fantastic at getting you to fall in. Oh, it’s a painting. Oh, it’s farm, it’s the farmers. I mean, imagine how great this will be. [00:55:42] Joe: This’ll be fantastic. You gotta look at the fees. You have to look at the liquidity event. When will this painting be sold? Will it ever be sold? If they find out something about this painting, what’s gonna happen if they find out something about this land? I don’t, there, there’s so many variables, I just hate this. [00:56:00] Joe: Inside your four four, and I’m gonna give [00:56:01] OG: you one more here. For the average person’s 401k balance, which I think I remember reading is right at a hundred k. Does that sound right to you? Yeah. Yeah. Guys, maybe. I think it’s slightly above. Yeah. How much are you seriously gonna invest here? 10%, 20, 30? Like we’re talking about a very insignificant total sum. [00:56:26] OG: 10 grand. 20 grand. 30 grand. For the average person I get this is not zero. That I’m not saying $30,000. Not a lot of money. I’m saying that you’re gonna take 30 grand and hope to do what with it? Make 4,500, make 5,000. At the risk of that 30,000 becoming zero, instead of having 3000 compounded like. We’re not investing the sums that are like life altering. [00:56:52] OG: This isn’t Bitcoin 2011. You know, it’s like, oh dude, if I’d have put 30 grand in Bitcoin 2011, I’d be a billionaire. Yeah, okay. I get that. You wouldn’t have held it the whole time, but oh fine. This isn’t life altering returns with the sums of money that we’re talking about in your 401k either, you know what I mean? [00:57:11] OG: So why do you wanna expose 10%, 20%, 30% of your, of your 401k to a potential, um, a negative a hundred percent loss, right? Or some profoundly awful result to make six grand, to make eight grand to that, to make 10 grand. It’s just not a big enough number in aggregate to me to move it, to make me want to do this stuff. [00:57:35] Joe: This is the sad thing, OG is I feel like our stackers, you know, as we communicate with ’em, we see them around the country. They’re in our basement, uh, community on Facebook when I see them, I actually don’t think our stackers are gonna get caught up in this a lot. But the reason I wanna do this headline is you’re gonna see your brother-in-law, or your sister-in-law who doesn’t know how to do any of this due diligence. [00:57:58] Joe: Who’s gonna be at the backyard barbecue and is gonna tell somebody in our stacker family, oh, you should see what I just did with my 401k. Oh boy. I think it’s gonna be the people that fall for sales pitches. When you go into a casino, half the people in the casino are people that can’t afford to be there. [00:58:16] Joe: The other half are people that, that, you know, take their play money shouldn’t be there, well, shouldn’t be there, but they’re taking their play money and they’re having a good time. There is a significant portion of the gambling public that needs the win that needs to hit blackjack, and those people should not be in these private investments out of, ugh, yuck. [00:58:38] Joe: I’ll link to this story on our show, CLDR. Don’t do this. Don’t do this. And and encourage those people that. Are doing this or thinking about doing this in the future, don’t do this. Send them our way. Yeah, send them to this segment. We’ll slap ’em around a little bit. Just have them listen and so they can do some due diligence. [00:58:59] Joe: Stacking Benjamins dot com is where you find the show notes. Also, uh, Kevin Bailey dives into topics like this in our newsletter, the 2 0 1, which comes out every week, uh, Stacking Benjamins dot com slash 2 0 1. You know, this isn’t the last time OG we’re doing this headline. This headline is just beginning. [00:59:16] Joe: This is talk about emerging markets. This is an emerging topic that we’ve now talked about. I think this is maybe the third time we’ve talked about it. I think 2026, we’re gonna all of a sudden have cautionary tales about people that lost a ton of money doing this kind of investing. If, if you call it investing. [00:59:36] Joe: Alright, let’s move on to the, uh, back porch. Doug. Speaking of community, what’s going on in our community, buddy? [00:59:43] Doug: Joe, there’s a lot going on in the community, but I think we need to pause a little bit and talk about something and a friend of the show, uh, that I know you were close with and meant a lot to you and meant a lot to our community that we should, we should probably pay some respects to. [00:59:57] Doug: So let’s talk a little bit about the passing of Jonathan Clements. [01:00:01] Joe: Jonathan Clements was the longtime personal finance columnist at the Wall Street Journal. Had a wonderful blog that he ran called The Humble Dollar, and uh, Jonathan had this great way with words that he could take these complex subjects and just go, this is good. [01:00:21] Joe: This is bad and could, uh, I think sometimes the simplest writing is the most difficult. Um, and Jonathan was able to write very plainly and very simply, and what, what I loved was when Jonathan realized that he had stage four cancer. He wrote about it openly. Mm-hmm. And he talked about the value of estate planning, getting your affairs in order and how important that was. [01:00:47] Joe: One of my favorite times with Jonathan was one of his appearances on the show, and he talked about the value. You guys know how much I love vacation Book the vacation way, way, way ahead of time. Don’t book it the day before you go. ’cause a big part of the deliciousness of a vacation is all the dreaming about it beforehand, about how fun it’s gonna be, about how the experience is gonna be. [01:01:10] Joe: And uh, it’s funny, we’re taking my mom on a, on a Christmas markets river cruise in December, and mom’s never been outta the United States. And I, I just know she’s gonna love it. And, and we book this thing back in the early spring after I talked to Jonathan for the last time. And, and all we do, mom and I and Cheryl, we spend a lot of time talking about how fun we’re, how much fun we’re gonna have. [01:01:37] Joe: Um, so for me that’s a very personal legacy of, uh, Jonathan Clements. He always talked about how this is more than money. And his last appearance on the show, we titled, what Makes a Life Worth Living. Um. Which is really what it’s all about. Jonathan can talk about what it’s all about. So sad to hear the passing of, uh, Jonathan Clements. [01:01:59] Joe: Next time we do our greatest Hits episode, we’ll play that episode, uh, for you so you can go back and listen to it ’cause it’s a timeless, evergreen episode. Alright. I don’t know how we [01:02:08] Doug: follow that, so we won’t, um, yeah, we won’t. But, uh, Joe, if you need a, uh, I, I forgot all about the Christmas markets cruise. [01:02:17] Doug: Do you need me to submit my Christmas wishlist to you guys so you can bring it, man? Have some focus when you’re on your trip? [01:02:25] Joe: I, I would absolutely love to pick you something up in, uh, the Christmas markets. Maybe, maybe I’ll drink a glass of mold wine on your behalf. I’m sure that’s what you would want. [01:02:34] Joe: That’s gonna happen. Anyways, that’s, that doesn’t make me feel special. I, I’m not doing the chestnuts over the open fire again. I did that last time. And those chestnuts smell great. There’s, and the dude in the stove top hat, you know the, the big tall hat, uh, cooking ’em looks really cool. They taste like crap. [01:02:54] Joe: They taste orange. Yeah. Did don’t need those. Alright, uh, Doug. What’s our takeaways for today? Give us the big three [01:03:02] Doug: First, take some advice from Jeremy Kyle by starting with how much you plan to spend. It’s much easier to create a retirement plan than it is to start with your investment strategy. [01:03:12] Doug: Everything is solvable. Once you know how much you wish to spend. Second, looking into private assets and your 401k plan, remember that while your returns may vary, you’re going to guarantee lots of money into the pockets of Wall Street bankers. That’s not who should have that money, but the big lesson, don’t tell OG that you’re earning money from the neighbor for keeping your clothes on. [01:03:35] Doug: He just said, if I never take off my shoes again while recording, he’ll double that woman’s $5, five more dollars just to keep my shoes on. Incredible. It’s like raining money down here. Wait, what? [01:03:53] Doug: Thanks to CFP Jeremy Kyle for joining us today. You’ll find his new book, retire Today. Create Your Retirement Master Plan in Five Simple Steps wherever books are sold, or on Jeremy’s website, jeremy kyle.com. That’s Kyle spelled KEIL. We’ll also include links in our show notes at Stacking Benjamins dot com. [01:04:14] Doug: This show is The Property of SP podcast LLC, copyright 2025 and is created by Joe Saul-Sehy. Joe gets some 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. [01:04:34] Doug: 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. 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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