Building Wealth Through Every “Era” of Your Life (SB1671)

Some people master reinvention. They move from one stage of life to the next with confidence, purpose, and an eye on long-term success. What if your financial plan could do the same?

In today’s roundtable, Joe is joined by Alyssa Maes, Roger Whitney (The Retirement Answer Man), and OG to talk about what it takes to build wealth that lasts—not just through one season of life, but through all of them.

🎯 Inside the episode:

• What starting strong in your 20s and 30s really looks like
• How to fight lifestyle creep and sharpen your personal brand mid-career
• Why simplifying cash flow in retirement can be a game-changer
• The power of habits, automation, and adaptability across all stages
• And what consistent, thoughtful choices can do for your long-term success

The thread running through it all? Knowing who you are, where you’re going—and letting your financial decisions reflect that.

We also sneak in a bit of trivia involving the most expensive comic book ever sold and a certain pop icon with a track record of breaking records (you can probably guess who).

This episode is about more than music or money—it’s about making every era of your life count.

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

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Our Topic: How to notch your money victories through all eras of your career

During our conversation, you’ll hear us mention:

• Career longevity
• Investing eras
• Starting out
• Mid-career
• Pre-retirement
• Retirement mindset
• Lifestyle creep
• Career capital
• Automation
• Emergency funds
• Fun budgeting
• Income control
• Habits
• Savings strategy
• Debt management
• Compounding
• Peer pressure
• Financial comparison
• Risk tolerance
• Deaccumulation
• Asset allocation
• Cashflow planning
• Simplification
• Emotional preparation
• Legacy planning

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Our Contributors

A big thanks to our contributors! You can check out more links for our guests below.

Alissa Krasner Maizes

Another thanks to Alissa Krasner Maizes for joining our contributors this week! Learn more about Alissa by visiting Fiduciary Fee-only financial Planning

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 on Apple Podcasts.

Learn more about Roger at Rock Retirement Club.

OG

For more on OG and his firm’s page, click here.

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Doug’s Game Show Trivia

• Back in 2014 the best kept copy of the iconic comic Action Comics #1 was sold at auction….for how much money?

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Mentioned in today’s show

• Building Habits That Stick (with James Clear)
• So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love

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Join Us on Monday!

Tune in on Monday when we discuss how do you put your best foot forward to score the deal, notch the raise, meet the right people, or make a good impression.

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Miss our last show? Check it out here: Harvard Business Review’s Kevin Evers on the Genius of Taylor Swift (SB1671).

Written by: Kevin Bailey

Episode transcript

[00:00:00] OG: Is this your place? No, 

[00:00:01] Doug: no, no, no, no, no, no. I live with my mom. Oh yeah. You hungry. Hey 

[00:00:07] Roger: Ma, can we get some meatloaf

[00:00:13] Doug: live from the basement of the YouTube headquarters? It’s the Stacking Benjamin Show.

I am Joe’s mom’s neighbor, Doug, and all this week we’ve been diving into the career of Taylor Swift. To help you make better financial and career decisions today. Let’s talk about the sheer longevity of Swift’s Reign at the top of the music industry like Swift. You wanna win through all of your eras, don’t you?

What does it take to notch those money victories? We’ll answer that question today, but that’s not all. Of course. We’ll also share a trivia question to see if we can’t narrow the gap in our year long challenge. And now a guy who, when you say challenge, he says, you’ve got this. He’s never once said that to me.

It’s Joe Saw. See all.

[00:01:17] Joe: Go to Doug. We just go challenge. Correct? Absolutely. Everybody, happy Friday. I am Joe Sulci. Hi. Ever show money on uh Twitter. Super happy that you’re here with us, man. Are we about to have some fun? It was fun actually getting here. We won’t describe how that happened, but we are all here and we’re ready to roll.

Let’s meet the team across the card table from me. Mr. OG is here. How are you man? Cheers. I put up my glasses so I can see. What are you pouring? 

[00:01:46] OG: Uh, apple juice. 

[00:01:48] Joe: Gotcha. Uh, 

[00:01:49] OG: in a blue can into a little mug. Little foamy apple juice. 

[00:01:53] Joe: Cleverly dis. You don’t want anybody thinking that you’re actually drinking apple juice.

So you disguise it as a nickel thread. Disguised 

[00:01:58] OG: it as a beer. Yeah. I Everybody knows you can’t drink beer on camera. So this is, that’s that Shane Gillis bit, you know, with, uh, when they’re doing the Bud Light commercial. Have you seen that? Yes. Him and Post Malone, they’re like, you can’t drink, you can’t do it.

You can’t, you just can’t do it. The 3, 2, 1 2. And then like, and then they’re done. So, and it’s done. This is, uh, in celebration of, uh, master’s tournament. These are my master’s mugs. Oh, look at those. Yeah. Nice 

[00:02:20] Joe: masters happened, uh, last Friday. Last weekend, or it’s happening right now depending on, 

[00:02:26] OG: depending on how you think about time and the construct of.

Of the, um, human experiment, 

[00:02:32] Joe: the miracle of the miracle of the recording, and the woman who’s like, man, I should have been on my third mic Ultra, based on just trying to get this rolling from Amplify my wealth. Alyssa Mes uh, financial planner is here. How are you? 

[00:02:46] Alissa: I’m great. I’m so happy to be here and it’s always worth the wait.

I always have fun talking about finances with you, so I’m in. 

[00:02:53] Joe: Yeah, we were having a good time backstage, but tell everybody about what you do there in South Florida. 

[00:02:59] Alissa: I’m guessing you’re thinking financially, but I’ll also talk about, you know, I’m thinking like, what’d I do in Florida? I don’t have a beer.

Yes. Water 

[00:03:06] Joe: ski. I 

[00:03:06] Alissa: enjoy the weather when it’s nice out. We still have some great weather. I like some good food, but truthfully, I’m a city girl, so I love getting up north and being in New York, um, I have lots of family up there. And also Boston. I know. We’re both gonna be in the same neck of the woods soon, so maybe we’ll get to see each other, then we’ll be Yeah.

[00:03:25] Joe: Graduation season up in Boston. Yeah, 

[00:03:27] Alissa: exactly. 

[00:03:28] Joe: And the gentleman who woke up from his nap to join us. It’s the retirement answer, man. Roger Whitney’s here. How are 

[00:03:35] Roger: you brother? This is what’s wrong with America. Men don’t drink beer anymore. What is that? Is That’s like wa. That’s colored water. Make a little al get a good IPA buddy.

Come on, og. Uh, it’s good to be here now that I’m awake. There we go. They, there we go. That’s, that’s what I’m talking about, Doug. Yeah. 

[00:03:54] Joe: Yeah. Doug’s drink. Those aren’t 

[00:03:55] Roger: beers. 

[00:03:56] Joe: Little Scooch. Yeah. Doug’s drink isn’t a beer. It’s his sample. He did for his doctor that he showed was a beer. That’s what I was thinking.

[00:04:03] Alissa: Looks like one of those little cups from.

[00:04:09] Roger: He 

[00:04:10] Joe: did pull it up from down there, 

[00:04:11] Alissa: so I’m happy someone said that. 

[00:04:14] Joe: We have been talking, uh, Taylor Swift all week. We had, uh, Kevin Evers from Harvard Business Review on Wednesday, Monday. We did a deep dive into the strategic genius of Taylor Swift, and it’s been a great year. Today, we’re just gonna use Taylor is our muse because it got me thinking.

Just like Swift throughout her career has had to emphasize different things. If you’re an investor, you need to emphasize different things during your career, early on in your twenties or teens or just starting out whatever age you’re starting out at. What is it you need to focus on? And then maybe mid-career, mid portfolio, what is the things that you need to focus on?

And then pre-retirement, maybe the five years before you retire into retirement, what do you need to think about? We’re gonna talk about the three eras. Of investing today, we’re gonna do our own ERAS tour, but ours is gonna take about 45 minutes. Before we get to that exciting discussion, we got a couple of sponsors that have made sure that we can keep on keeping on.

You don’t have to pay a dime for all of this goodness, with Alyssa and Roger and OG and neighbor, Doug and I. So we’re gonna hear from them and then we’re gonna talk eras of investing. So let’s get the party started.

All right. Let’s begin from the beginning, guys. You’re just starting out as an investor. I don’t think the age is, well, maybe the age is important. We’ll find out from you, but Alyssa, let’s go ladies first. If we are thinking like Taylor Swift when she’s just starting her career, but it’s your career as an investor, what do you think the number one thing is?

I should be really thinking about. 

[00:05:48] Alissa: I love one of the things that she deals with, which is stickiness and it’s kind of. Counter post, ’cause I’m gonna also use the lyric to go with that. So when you think about what’s going on in the market now, and which Josh just spoke to, is the idea of shake it off, don’t let everything get to you, but also have a plan that’s sticky.

So definitely it’s important to do something that resonates with you just because. One person does it one way and another person does another, it has to work for you. So make sure you have your own plan and your own way of implementing things. That of course, works, not just some random plan. And if you’re just starting out and yes, I’m gonna say another lyric.

Sorry, Joe, but you put the Taylor Swift out there, so bring it, you’re on your own. The twenties and thirties, right? For the people just starting out. That it’s important to target what’s untapped, so don’t do what everyone else is doing, because most people in their twenties and thirties, they’re not necessarily thinking about automating and maxing out their retirement instead.

Figure something out that works for you and use the advantage of time that you have on your side to compound and grow your wealth because the earlier you start, the much easier it is to grow and then not be bothered, because this way you’ll experience the ups and downs and the people who’ve done it sooner are usually much more comfortable in the past week or so because we’ve been through it before.

[00:07:22] Joe: Yeah, you’ve already had a few bats. That’s the great thing about Taylor Swift starting at 13. We talked about that on Monday, that she had so many times writing songs, she’d written so many songs. It became. Very easy. Roger, I’m assuming that you agree with Alyssa. It’s funny. She said you can do it your own way.

I remember we had the discussion with the former Wall Street Journal personal finance columnist, uh, Jonathan Clements. And Jonathan was saying, you really have two roads. You can go down, you can, number one, you can play in your twenties, and that’s fine and not save much money and really take advantage of this time of life.

Or you can really put the pedal to the metal and save as much as you possibly can, be as frugal as you possibly can. When Wes Moss joined us, Wes was like, I kind of prefer option two. I kind of prefer the get used to being frugal, get used to working hard. If you’re gonna give people advice in their twenties, which of those options do you think is the one they should probably take?

I actually think option three is the best option, 

[00:08:20] Roger: Joe, which is there is, we’re all standing on a teeter-totter trying to have a great life today and be, have a great life later in life. And I don’t think you have to choose one or the other. I think you can have a little bit of both if you’re intentional about it, ’cause it’s all a matter of moderation.

I would disagree with the framing of those two options. I do think early on it is about, as Alyssa said, building the habits of saving. I think that’s when we have to instill the habits of saving. Probably in early career, it’s doing what Taylor Swift did, which was really build career capital, which is a concept that I learned from from Cal Newport’s book.

So good. They can’t ignore you of being so good. They can’t ignore you in what your profession is. That is the time in the twenties is to put, build your reputation. I think that’s an area of investing that in early career we forget about because we’re thinking about 4 0 1 Ks and Roth IRAs and all of those other things.

[00:09:25] Joe: That is interesting. Og, I mean, we talk about investing. You know, I thought initially in this topic that we’re talking about just investing in investments. And, uh, Alyssa said, you know, hey, decide which way you’re gonna go. But really what Roger said is interesting. This might be a time to invest in yourself.

[00:09:42] OG: I mean, no different than your diversification within your investment portfolio. I think, I think it’s important to set the, you know, set the foundation and start building the pyramid the right way. It’s really fun to invest in all the fun things, right? Like all the esoteric, you know, whatever things you think are at the top of the pyramid that you think are gonna just really catapult you to the next level.

But the reality is, is that you can’t build it the right way unless you do. The foundational stuff first and some of the foundational stuff is the really boring automation of, you know, living within your means, like Roger was talking about and automating and kind of building the self-confidence that Alyssa was talking about in terms of your personal life.

It’s, it’s making sure that you don’t go too far into debt. It’s you’re. Gonna have some, it’s like, there’s no way. I, I just don’t, I just, I disagree with the Dave Ramseys of the world of like, you can just live your life without having any debt. I think, I think being smart about it is important. I think making sure that you automate the things that you can automate in terms of your retirement plan savings.

We’d all love to start day one and max out your 401k. But maybe that’s not realistic in your budget or in your cash flow. So set it up so that it increases automatically over time, right? Set it up so that you have that automatic escalation. You know, every six months or every year, make sure that you’re building a cash reserve.

The real boring things. I also think that you have to invest in yourself. I think you have to find out what sparks the joy in your life and what do you find interesting? ’cause in your twenties you might not know what that looks like. And so I think it’s important to experience a bunch of different things.

You don’t want to have all the experiences and then be 30 and have, you know, a hundred thousand dollars worth of debt because you’re like, I was ex, I was finding myself in doing experiences and I went and got three degrees and you know, I got all this stuff. It’s like, okay, you dug yourself a big hole.

When I look back on my life and I think. I started financial planning just after the Roth IRA started, and for the people who don’t remember this, the limit was $2,000. That was the limit. It hasn’t really gone up very much at all. Now it’s only 7,000, but at $2,000, $166 and 67 cents a month, right?

Everybody remembers that, who’s been around for a while, and it’s, and I think back and I go, what was I doing? That I didn’t have 160 bucks or a hundred or 75 or 50 or five, you know, like how did I make it through the year 2000 with not a dollar in Roth contributions? It’s because I had a lot of stuff going on and I went, I’ll just do that later.

But we know now, 20 years later, the power of compounding and we get to experience with people and with our community. Just doing a little bit of that stuff early on builds that right habit. So it’s building the foundation, it’s building the right habits, uh, and I think it’s a little bit of fun too in moderation.

So all of those things. 

[00:12:38] Joe: I like what you said about automating ’cause I think that is a skill if you get comfortable by creating that. Automatic investing stream, and then by setting that automatic so that it goes up every six months, I think that’s a great tactic for people starting out. Let’s talk that.

Let’s do a round, a specific one. Specific tactic. You think somebody starting out should have I pick automation that they do? I was gonna pick that. You already took that one. Uh, so Alyssa, what is another tactic? A specific one tactic that somebody just starting out should. And begin doing. 

[00:13:18] Alissa: I think it’s also important to automate having money transfer into a savings account.

For an emergency fund, of course I would be negligent, not to mention, but also to have a separate account for fun, and I have my clients do that because it’s not about depriving yourself. That’s not gonna end up with great success either. You’re not gonna be as happy. Or you won’t have as many friends, or there’s always something that is negative, in my opinion at least.

So I think having a separate account where yes, your money is going to saving for retirement or whatever other places to take care of your future self, but also an account that is within your budget that you could take that money and do something fun that you value, like Josh was mentioning, there are things you value and make sure you are doing those things.

[00:14:07] Joe: I like the idea of budgeting in your fund because. I mean, too often in my twenties, fun was an unlimited number until it was too late. Right? And that’s where a lot of my credit card debt came from. So locking down that number I think is great. Roger, what’s another thing? Somebody starting out, a tactic that they should have in their quiver.

I think 

[00:14:25] Roger: we’re all hitting on the same theme here. Mine is similar to Alyssa’s, but it’s opposite. One thing that I did early on, because I am allergic to the B word, which is budgeting. Was I had all of my income come into a income account, and then once a month I transferred over money to my checking account, and that’s what I lived on, fun and everything.

So I would suggest that have some system in place, so the money that you don’t need to live on or have fun with doesn’t get into your purview in terms of looking at it when you log into your bank account. Automation, what Alyssa was talking about in this strategy all have a similar theme, which is you can’t, well, you wanna buy discipline at the grocery store.

Like if you’re trying to lose weight or manage your nutrition, you plan ahead of time. Don’t trust that you’re gonna be disciplined to make the Roth contribution or to spend money on fun. I think that’s the, the common thread that we all have here. One other example there, Joe, to go to the comedy world of, think of what Jerry Seinfeld did.

He has a habit of not breaking the chain. I don’t know how old he was when he started it, but he writes a joke every single day and he puts a dot on the calendar. The idea of building that habit of not breaking a chain is a lot of what we’re talking about here and early on is when you gotta do that. 

[00:15:50] Joe: I think this idea of just Roger learning about habit building.

About how, I mean, this is a great time to read a book like Atomic Habits. We talked about him earlier in the week with another Taylor Swift example. Like, um, we’ll link to our interview with James Clear, the author of Atomic Habits, because I, I think, man, if you can start working that muscle, to your point, Roger, I think that’s great.

Doug, what’s another one that, um, maybe a tactic that you could have learned in your twenties or. Maybe, uh, maybe did in your twenties. It was good stuff. Yeah, 

[00:16:19] Doug: I, Roger just kept on talking and talking and talking and he took like five of mine all at once. So. You’re a very smart man. I’ll say this. Focus on your career.

How about that? We keep talking about automating savings and, and experiences. Instagram is ruining a generation because everybody feels like they’ve gotta show up in the Greek islands when they’re 22 and experience all of this stuff when they’re looking hot in a bathing suit. How about we just buckle down and work?

Love it. How about you? Love it? Just, just really focus on getting good. At an early age, at a specific skillset so that you can get the momentum rolling on your career, and then maybe you’ll still look hot in a bathing suit when you’re 32 and you can go on vacation. But, but all of this notion that we have to do all of the experiences when we’re young and in our twenties is kind of infuriating.

Mm. I don’t think it’s infuriating at 

[00:17:16] Joe: all. I really do agree. Like I opened this up with, with Jonathan Clement says, you have a choice. I mean, you do have a choice. Just realize that you have a choice and you’re gonna pay for it. You’re gonna pay for it either way. Well, I 

[00:17:24] OG: think Doug’s point is, is that no offense to the fine 20 year olds that are listening, but they don’t know what the hell they’re choosing.

Right. You know, they don’t, they recognize the choice. I. Prefrontal cortex isn’t fully 

[00:17:36] Roger: developed yet. Be great at what you do. And just for the record, Doug, I actually said that one too, so I just wanna mention that. 

[00:17:41] Doug: I know, I just, I started to get dizzy when you were saying all of the words 

[00:17:45] Joe: and I just couldn’t keep ’em all straight.

My point would be, ’cause I really like Alyssa, is to put a number on your phone. I would even think hard about what fun really is. Is this fun or is this just me spending money like everybody else’s? Because it was very easy for me during my twenties to get caught up in what everybody else was doing and whether I really truly enjoyed spending that money or not.

’cause I. Something. I think another thing you learn later on is that spending money on the things you love is great and but beyond that, you see people wasting so much money on stuff that they truly don’t, don’t care about that much. Speaking of, don’t care about that much. What is a thing that 20 year olds, oh gee, you brought up this topic that they waste their time thinking about, that they truly shouldn’t be worried about.

Like, worry about that. You’re worried too much about this now, worry about it later. 

[00:18:32] OG: I think trying to fast forward too much. Compounding, whether it’s learning or money or whatever, it takes a while to do, you know, and you just don’t see the results of it right away. In fact, you don’t even, you don’t see it ever, like you see the witnesses of it on the backend.

Like when you look backward, you can see compounding in learning and in terms of your money and all that sort of stuff. But in real time you don’t see compounding. I hear a lot of, uh, people with anxiety around. The thing that they think they should be doing at this age, based on like what Doug said, maybe what was on Instagram, you know, like, I don’t know.

I, I, I saw an article about, um, you know, housing and prices and stuff like that, and people were like. I’ll never be able to afford a house. And don’t get me wrong, housing prices and that sort of stuff, it’s, it’s a sensitive subject and there’s, you know, it’s expensive. Yeah. I mean, it is expensive, but it was expensive when I was a kid too.

Yes. And it was expensive when, you know, when we were, we all had that emotion of like, how the hell am I gonna pull this off? You know? And how did we do it? We saved a bunch of money. Like that’s the, you know, you don’t have to get the white picket fence type deal when you’re 26. I didn’t move into the house.

That’s our quote unquote forever house until I was 40 and from 38 to 40 I lived in an apartment. You know, trust me, it felt really uninspiring and and whatnot. That doesn’t make our way right or wrong, but I’m just saying like, I feel like, I feel like a lot of times people want to fast forward to the end.

They just like go, well, I should be, you know, I should be investing in the, in the IPOs. I heard that private equity’s really cool. I should be doing that. It’s like, dude, you need a cash reserve, man. Like you need to be saving two 50 a month into your freaking savings account for a while. Or how do I pay off my student loans 200 bucks a month at a time?

I mean, sure. Work hard to to get through it, but I guess just don’t be in such a hurry. Maybe is the good way to summarize that. Yeah. We talked about it’ll come, don’t worry. I like 

[00:20:28] Joe: that callback too. Earlier in the week where we talked about enjoying the process about it becomes clear. Taylor Swift really likes writing songs, you know?

Yeah. 

[00:20:35] OG: Like, you’re not gonna get the best job right away. Your boss is gonna be a jerk. Maybe you’re gonna get passed over for promotions. You’re gonna be overqualified or underqualified. Like that stuff happens. Like that’s just, that’s just life. Alyssa, 

[00:20:48] Joe: what’s another thing? Uh, people starting out worry about too much.

[00:20:51] Alissa: What other people think. I think that there’s so much of that, whether it’s you are friends with people or in relationships with people because of what other people might, what you think they’re gonna think about you rather than what you think is best for you. I think sometimes when we’re younger, you know, maybe it’s the person who’s going out all the time.

I mean, I used to like going out in my twenties. I probably didn’t put a lot of butts sometimes into the people I hung out with. I mean, I know who my close friends were and I distinguished them, but I still looking back like, yeah, some of the people we hung out with maybe, I mean, they wouldn’t be my lifelong friends, and it’s fine to do that, but do it because that’s.

What you wanna do, don’t do it ’cause your friends are doing it. Just like investing. When I’ve had people discuss with me some of the decisions they made with investing and they’re like, their brother told them to do it, or they saw it on Instagram or it’s just like. Make sure you increase your own financial literacy.

If you don’t understand something, just don’t do it. It doesn’t matter if all your friends are doing it. Same thing with anything your friends are doing. I understand people wanna be a part of a group and feel accepted, but just ’cause they’re doing it doesn’t mean it’s right. I’ve had people share with me that they’re in their groups of friends, that they’ve normalized debt.

It’s just, you know, like we’re having this discussion. They talk about that like it’s okay instead of trying to help each other and lift each other up. So just think about who you’re hanging out with and what’s best for you and where you wanna be. 

[00:22:27] Joe: Yeah. Everybody has debt. I mean, come on, everybody’s got debt and everybody whips out credit card and you think that they probably have water’s 

[00:22:32] OG: warm.

Jump on in 

[00:22:36] Roger: Roger. I actually had a podcast. I, I recorded a couple pilot episodes called I Love Debt, and it was gonna be a par. We had the, we had the debt rules. I think I still have the t-shirt for it, but it never, I remember you Vincent Psi 

[00:22:49] Joe: at a conference. Yes. And brainstorm that, I think after a couple of those Mick Ultras.

Yes. Maybe. 

[00:22:55] Roger: I, I’m gonna agree with Alyssa here on, it’s that Jim Rome quote, right? You look around at your circle of friends and that’s who you’re going to be. So pick them carefully. I would argue nowadays that Josh and I didn’t have to deal with, uh, and you, Joe, is that there are so many counterfeit experts out there.

On the internet and on podcasts, it’s very easy to sound like you know what you’re talking about with zero experience and we all live online and it’s very hard to remember that the internet is essentially a sales funnel. That’s really all it is. If you look for a review of a camera, it’s because they have an affiliate link.

It’s the same thing in the financial world, so you have to be very careful. On who you even allow into your head from a, what you’re listening to, because there are so many counterfeit experts that have never actually done what they’re talking about, they’re aspiring to. And that’s where, going back to the boring stuff, there’s a reason I have the daily stoic that I read every day.

There’s a reason that you go back to tried and true wisdom that isn’t sexy. It’s not the bling of planning that gets us excited. It’s chop wood, carry water, do the work, work, be good at what you do. 

[00:24:08] Joe: I wanna spend a little extra time with people just starting out. ’cause I think that’s really important.

Obviously it’s gonna be important for people that are in the middle of their journey. We’re gonna spend a little time on that. But, uh, also, of course, for people that are in retirement, we’re gonna do that after the break. But at the. Near halfway point. This will be a little before the halfway point of our podcast on Friday, we have this gigantic, exciting and amazing trivia competition where our three frequent, uh, contributors OG Jesse Kramer and Paula Pant, uh, fighting over this, uh, year long worthless well dollar store trophy.

That, uh, is it, it’s not worthless, is it? Is that it back there? There it is. There’s the dollar star. Dollar star trophy. Just to keep things really easy, we’ll have Alyssa, you’ll be Team Paula. We’ll just keep women with women today, which means that you are team Jesse, Roger, Alyssa, would you like the good news or the bad news?

[00:25:04] Alissa: Yes.

[00:25:07] Joe: All the above. Well, the, the, I guess the good news is, is that, uh, this is the same place ’cause you played for Paula before Paula’s in last place, which is no change, no different. Uh, Paula has one and a half points. Jesse has three and a half points. OG has five points, and that means Alyssa, you get to guess last Roger, because your team, Jesse, you get your guessing second.

OG is guessing first, and uh, man, we’re really looking for either Paula to tighten up things on Jesse or Jesse to finally start putting some pressure on og. So it’s an exciting week. What’s the score? Sorry I wasn’t for all that. Yeah, he just wants me to say it again. OG is five. Jesse, 3.5. Paula 1.5 points.

Doug’s got this week’s trivia. Does it have anything to do with Taylor Swift? 

[00:25:56] Doug: A little bit, but I gotta say I did not like how Roger was looking right at me when he said counterfeit experts. I mean, I caught, I caught what was happening there. Roger. We’re gonna see how you feel after I throw this trivia question out there.

’cause it is not easy. Hey there stackers. I’m Joe’s mom’s neighbor. Duggan. What a superman. Taylor Swift is how I mean superwoman. Well, I don’t, I don’t need to tell you because. You’ve been learning from her career all week. So while we are talking about superheroes, let’s go there. The most expensive comic ever sold actually first debuted on today’s date in history.

Action comics number one, featuring the Taylor Swift. Of superheroes, Superman. Back in 2014, the best kept copy of this iconic comic was sold at auction For how much money? Retirement. Answer, man. I’ll be back right after I go grab my Superman. Under Ruse should be wearing those for this. 

[00:26:58] Joe: Absolutely. Uh, Doug’s gonna go get those OG 2014 action comics number one.

What did it sell for?

[00:27:10] OG: Is that the one with Spider-Man? He just said this with Superman. He literally 

[00:27:13] Doug: just said, Superman, dude. Superman. Where 

[00:27:17] OG: are you? Okay. Superman. All right, well that’s different then. I, I heard, man, and I heard a word that started with the nasa. I just want clarification. And when was the comic first produced?

Is that, is that a known, known. I don’t think we gave you that information. 

[00:27:31] Doug: We did not give you that information is not necessary for you to provide an answer. 

[00:27:35] Roger: False. Are you gonna ask him to use it in a sentence now? Yes. 

[00:27:40] OG: Uh, so a really good comic with Superman, and, and this was sold at auction and it was a, like a mint copy.

[00:27:50] Joe: Mint copy. Most expensive. The best copy in existence. Most expensive sale ever of a comic book. 

[00:27:56] OG: Uh, okay. So this is like a Babe Ruth. Baseball card. 

[00:28:02] Joe: $4 million. $4 million. Roger, what do you think about that? 2.4 million? 

[00:28:11] OG: He just went right to it. He just 

[00:28:12] Joe: thinks 2.4 million. So you think he’s a little north of where he should be?

Josh is always high.

Interpretations. Alyssa, you’ve got 4000002.4 million. What do you think? 

[00:28:31] Alissa: 3.6. 

[00:28:34] Joe: 3.6. So you’re gonna kick a field goal right between the two of them. All right, we’ve got OG at 4 million, Alyssa at 3.6. Roger at 2.4. Who’s right? Is Alyssa going to help Dean Paula? Get closer to team Jesse and Roger. Is Roger gonna help Jesse put pressure on og?

We’ll find out in a second. Og, you kicked it off with $4 million in both. Uh, Alyssa and Roger said no. I think that might be a sco. Um, too much money. What do you think? 

[00:29:08] OG: No idea. 

[00:29:09] Joe: Roger 2.4, you’ve got, if it’s less than 2.4, you’ve got that in the bag and partway up to 3.6 million. Feeling good? I feel great, and I’m horrible at this trivia.

I’m so glad that I can contribute this time. And Alyssa, you’re right up the middle there with 3.6. Feeling good. No, 

[00:29:29] Alissa: but I figure, I mean, Paul will be happy if I won and if not, well that’s right. He’s in the same place as 

[00:29:37] Joe: before. Paul’s already in last. Well, let’s see if Melissa’s going to maybe give Paul a big win.

Roger gonna get a big win og. Doug, what’s our answer?

[00:29:52] Doug: Hey there, stackers. I’m superhero lover and guy who’s very comfortable taking your abuse about his Superman sheets. Joe’s mom’s neighbor, Doug. Today we’re talking about a comic that debuted on this day in 1938. It’s action comics, number one, featuring Superman, not Spider-Man. Superman. Superman initially was just one superhero among many others, but over time he became so popular that later he’d score his own issues all by himself.

But issue number one was sold at auction back in 2014. For how much money? Well, I’m not gonna tell you just yet, but what I will tell you is that the correct answer is $800,000 more than what Roger guessed. 800,000 less than what OG guessed, and just 200,000 less than what Alyssa guessed making. Alyssa, or shall I say, Paula, a real 

[00:30:43] Joe: winner here.

How about that, Alyssa? Bringing home the win. Nice job one. You gonna make accepted speech, victory speech. 

[00:30:57] Alissa: I am happy to help Paula, and I’m shocked that I won. 

[00:31:02] Joe: And, and Roger, 

[00:31:03] Roger: what’d you say? You’d never win. I’ve never gotten one of these. Right. I’ve always been a loser for whoever I’ve been replacing, and I apologize.

I’m just so happy it wasn’t Paula. ’cause I think she was the one that I didn’t help last time. 

[00:31:16] Joe: Well, th well, well this time you, you help Paula get it right. Nice work. Hey, let’s dive into the second half of this discussion. Let’s set the stage here. You’re in the middle of your career. You’ve done a good job of saving.

Obviously things are getting maybe a little more, uh, comfortable in your work life. Hopefully. What is the big thing middle of your career? How do you need to change that focus when you now get into mid-career? Roger, let’s start with you man. Where are 

we 

[00:31:45] Roger: starting? I’m ready man. Two things. Number one is you’re starting to finally make some money ’cause you’re pro, you have a reputation that you know it.

You can actually work well. So you need to control your lifestyle creep. Just ’cause you’re starting to make some money doesn’t mean it’s gonna go up forever. Life will hit you in the face Is our lifestyle creep. Doug is the creep. Doug, is that who we’re talking about? Gotta keep him controlled. Uh, I was looking at him.

But, uh, and that second, now is the time to start positioning yourself to maximize income. Uh, ’cause if you’ve built up this career capital and have proven yourself worthy. You have probably done it maybe at one company and my wife used to be in hr. The only way you really make more money is by moving. So you wanna start working on your, your network within your industry and start really positioning yourself to take a leap if you really are focusing on maximizing income.

And I think those are the two things you should focus on. 

[00:32:44] Joe: I love both of those, that lifestyle creep is a real thing and it’s really easy because you’re juggling so many different things in the middle of your career. I positioning for Max income. We’ve got, uh, Lorraine Lee joining us next week. We’re gonna help people do that tactically working on your career branding, and as we mentioned on Wednesday.

You say the words career branding and everybody rolls their eyes. But Lorraine changed my mind on that when she told me. She goes, if you roll your eyes at career branding, realize you have a career brand, yours just probably sucks ’cause you haven’t thought about it at all. Your sucks. And just never use the phrase thought leader.

Please don. Inside the box. Outside the box. Planning. Win-win. Og what, uh, would you like to add to what Roger said about mid-career, mid uh, portfolio growth? Things we need to think about. 

[00:33:29] OG: Well, I, I guess I’m thinking has this person done the right stuff up to this point? You gotta gimme some little context.

So, so this person’s done great things up here. Yeah. Don’t, is it time 

[00:33:37] Joe: for a checkup if we haven’t, I mean, what’s the, Hmm? What’s the ying YY there? 

[00:33:42] OG: I think it depends, like, so two things I’m thinking about a, um, a person who maybe just kind of wakes up and goes, oh crap. Oh, I, I party too. I, I pulled a Joe.

That’s what we would call, well, what I would say is I pulled a Peter, I would call it pulling a Peter. A good friend of mine likes to have a little fun and, and maybe has too much fun. You know, you get to 40 and you’re like, I had too much fun. Now I need to get after it. I think the biggest thing to recognize is you have more time than you think.

So if you’re on that side of the equation and you’re going like. Oh crap. I didn’t do, like, I didn’t do this stuff when I was my twenties. I didn’t do this stuff when I was, and, and now I’m 40. I’m making good money. Like Roger said, I’m trying to work on my career trajectory. I’ve maybe managed to do that, but I haven’t done any of this other stuff.

You don’t have to swing for the fences. I. Are you gonna be behind the person who started it at 20? Yeah, absolutely you are. That’s the trade off, like you were talking about before, Joe. But the reality is, is that you don’t have to swing for the fences. And I think the problem is, is people think, oh crap, I don’t have any time at all, so I’m gonna make all these radical things.

I’m gonna try to do all this aggressive stuff. I’m gonna day trade penny stocks, I’m gonna try to do all these things to get caught up. You don’t need to. You have so much time still join that, that Amway representative, right? Yeah. All these extras, you’re gonna be a little behind the, the gal who started when she was 20.

It just is, you know, that’s the trade, but you have more time. So if you’re in the spot, and I think this is more likely than the other side, if you’re in the spot where you’re going like, ah, crap. Like what do I do? Yes, you have to make some changes. Yes. You have to be proactive. I would encourage you to look that everything on the table counts.

Sometimes you look at your budget as a great example. Roger says, anti budgett, so am I. And it’s like, you know, you look and you go, well, you know, but I have to have the club membership. Like that’s where all my friends, you don’t, you may choose to, well my kids have to go to that school. I need a new car.

You know, you can make some pretty radical changes if everything counts. So I think the biggest message for somebody who’s maybe waking up one day going, oh crap. I need to get after it is you gotta start building the foundation. You have to do the same stuff, but you have more time than you think. Even if you pulled a Peter, which is what we say.

[00:35:58] Roger: That is so well said, Josh. I, I literally lived what you talked about. Oh. In terms of partying. Too much thinking I was all that, and then having to clean up my mess. There is enough time. 

[00:36:12] OG: You have a ton of time. Yeah. I mean, do you get to retire at 50 and also party all your twenties and thirties? No, you don’t.

You just don’t. I mean, that’s not gonna be You can you do it at 65? Absolutely. Plenty of time. 25 years is a long time. I. 

[00:36:26] Joe: I like the idea of just taking a breath. You know, you guys have both said that you’re anti budgett, but I do think, especially when it comes to that lifestyle creep and knowing what’s important, tracking your expenses and looking at it so you, so you know where the out of bounds lines are.

I think it’s pretty crucial there. Alyssa, let’s add another one. 

[00:36:44] Alissa: Okay. Just along those lines. First of all, a Taylor Swift line. ’cause that’s why you gotta do it. You gotta do it. I think I’ve seen this film before. With respect to that. When you think about, you know, one of the things that she does is maintaining her productive paranoia is it’s okay to have a little paranoia.

I don’t think it should rule your life or your finances, but it’s okay to pause for a second and think, as I think Roger, you’d said this, you know, maybe you’re making a lot of money. I’ve seen a lot of people, they’re making a lot of money. They’re busy. They’re busy with their families or their job or both, and they haven’t really been checking on their finances.

Maybe their money is sitting in a checking account, making nothing. Maybe they have a few hundred thousand dollars just sitting around. Doing nothing. You know, a lot of times we just get into doing the same thing day in and day out. We’re really busy. Just because you earn a lot of money doesn’t mean you’re gonna have enough for retirement.

Actually, as was discussed, lifestyle creep. A lot of times you end up not having enough money, at least to have that lifestyle. So take the time, check in on your finances. I personally don’t budget myself. Self all the time. But that being said, I do from time to time do what Joe mentioned, which is track your expenses and see where you are.

Because especially the past few years, expenses have gone up. So if you thought you were gonna have enough for retirement, it might look a little different now. Maybe just need to adjust your way of living so you could still retire when you wanted to. So I definitely think a little paranoid is good, or maybe cautiousness, whatever you wanna call it, and make sure that you’re staying on track so you don’t wake up one day wishing ’cause.

I agree with Josh that there is something you could do now, it’s not too late. It might mean reframing certain things you’re doing now or in the future, but you can definitely have a plan and feel great about it. 

[00:38:45] Joe: Yeah, I think fear can be a good thing if it’s used well. You know, I mean, if it’s used productively, productive fear is not necessarily a bad thing.

Like fear that paralyzes you and you do nothing is absolutely horrible. But I love this idea of using it, you know, and I’m not gonna ask you guys what they shouldn’t do because, oh gee, I really like your, I. You are kind of got this question all the time. You guys, all three of you must get this question all the time.

Am I head or behind? Am I head? Other people? Am I behind? How do I compare to other people? Like, don’t, don’t do the comparison. Don’t focus on that you’re behind or ahead. It’s all about just reaching your goal. I want pivot though, to people, those last five years of retirement into their retirement years.

Og, let’s have you start this round. We’re. Retirement. We’re landing the plane. We’re landing the plane. What is the thing? 

[00:39:35] OG: What is 

[00:39:36] Joe: one thing we really need to focus on that we didn’t need to focus on during those other two eras? 

[00:39:42] OG: Well, again, I’m just gonna try to create a person in my brain here that’s five years out that’s maybe done a okay job of this stuff.

I think now is a good time to start thinking about where the cash flow’s gonna come from, if you’ve been a really good saver for your entire life. Uh, in my experience anyway. Good savers don’t turn into good spenders. I. I, I’m a great spender. So, you know, the opposite is also true. I have no, no, no. Not, no.

I have a great, what’s the thing says 

[00:40:09] Joe: Doug. Scoreboard. Scoreboard. Scoreboard. I’m a great spender. 

[00:40:12] OG: No, no. I’m an expert spender, especially of other people’s money. I can, I can tell you how to spend your money like crazy. So if you’ve been a good saver, if you’ve been a good investor your whole life, flipping that switch to turning into a, uh, spender is not super easy to do.

So I think starting to think about like where that cash flow is gonna come from and starting to see how you build that cash flow out for the first few years of, of your financial independence time, I, I think, is really helpful and sets the stage for a good transition. It also helps you identify any sort of gaps that you might have.

Like if all of a sudden you’re like, oh crap, I’m five years out and all I have is 401k money and I’m, and I wanna retire at 57. Uh oh. Now we have to solve, we have a little problem to solve, and it’s just something to think about, like, how am I, you know, do I save? Do I stop doing 401k contributions for the next five years and just put it in brokerage so that I’ve got some, you know what I mean?

Like it gives you an opportunity to start thinking about those things. So all of that stems from how am I gonna pay myself five years from now? From a cashflow standpoint, if you build that out, it gives you an opportunity to kind of see where the pitfalls might be. 

[00:41:17] Alissa: I love what you touched upon, Josh, especially when you’re thinking about the past week and the market fluctuations and because the market’s been so great for so many years with it, for the most part going up.

Obviously there are days that doesn’t, and then I. For people who are near retirement or in retirement experiencing the last week, it’s really been hard on them. And so I think it’s really a moment where we could all just pause. And while I still agree with what Josh said about mid-career, and obviously it’s always.

Easier for you to start sooner, but I still think that you can still do something. I’ve met people who literally were in debt in their sixties and they were determined. They realized that they were not gonna be prepared to ever stop working. And they’ve even said inspirational things, that you can do something.

These are people who initially had no hope and turned it around. It might be reframing, but the other thing is, and of course my last Taylor Swift thing, because I gotta get it out there. I’m not even a swifty, but I’m like, you told me, I just follow directions. Okay. You understood homework? Yeah, I did. This one is I come back stronger than a nineties trend, and that’s what it’s about.

You can come back stronger, definitely check where you are and make the shifts that you have to make because. That’s the most important thing. And once again, back to the beginning is don’t let what’s going on in the market dictate how you make your decisions. ’cause that’s how people end up not being where they wanna be, is they see what other people are doing.

Are they yet nervous? So you’re like, if you’re invested in the market. Josh said, you know, it’s good if you wanna retire earlier. You should have some money in a brokerage account, ideally, or money market something so you can access the money just in case you wanna do that. But also make sure you consider your risk tolerance before you invest and having a diversified portfolio.

Because I think people who did that and they really aligned it with their comfort level. They were also more comfortable the past week than other people. 

[00:43:28] Joe: It’s so funny. I back way, way back when I was a financial planner. It was always my clients that tried to convince me over and over, no, I’m super aggressive.

I’m super aggressive. And I’m like, huh, you don’t come across super aggress. No, I’m great. I’m great. They were always the first people on the phone to me. When the market started going down and what are we gonna, I think we gotta sell it all. I think we gotta, it’s funny how you’re aggressive as long as it goes up.

That kind of changes. Uh, Roger, give us one for the other side. Both Alyssa and OG talk to the, you know, five years before you retire. What’s so of the people need to really focus on when they’re in retirement with their money that they didn’t need to focus on before that. Before I share my word, s 

[00:44:08] Roger: salad.

Doug, would you, do you have anything you’d like to say first? 

[00:44:13] Doug: I appreciate that opportunity. That was very considerate of you, RA and I will, uh, it’s, I’ll seed my time to the Senator from, uh, the mountain time zone. 

[00:44:23] Roger: Uh, overcoming frugality is definitely a big one of ’em, which Josh hit on, I think in retirement or right at the time of retirement.

We have to be very careful of being trapped in the cage that we’ve created for ourselves. And what I mean by that, generally we live in a certain place. We do certain things. We have certain things in our life because they were collected when we were starting a family. And then in the school district we lived in or the commute that we had to work.

In retirement life is literally a blank slate, but inertia really sets in and it’s very difficult to reimagine what life would be by right sizing your lifestyle for the season that you’re entering. So I think it’s very important that people look at things with fresh eyes from a portfolio perspective.

Generally in our fifties and going into retirement, what I see all the time is what I call cluttered closet. It’s like walking into a garage where it’s just jam packed. I have this IRA over here. I have these 20 investments for this advisor who is trying to be a stock trader, and we just have all this stuff.

I think simplifying that into one coherent plan makes sense 

[00:45:34] Joe: as well. I love that tactical approach because I do think that getting the assets in order is so important to discern how you’re going to spend your money down. I think we spend a lot of time, Roger, talking about how we’re gonna build up our portfolio, but not nearly enough thinking about how we’re gonna, how we’re gonna, uh, I was gonna say deconstruct, but you know what I mean.

Uh, how I’m gonna start Deac accumulate deaccumulation. Yes. Thank you. And literally, 

[00:45:59] Roger: the strategy is very different than accumulation deaccumulation. Investment decisions are very different than accumulation decisions. And many of us aren’t aware of that. And for those of us that, uh, have been blessed to be good accumulators, ’cause we built the habits, it’s like those guys that, that are in the gym where they’re just, they’re huge up here and they have chicken legs.

They don’t want to focus on building new muscles. And that can cause them some unnecessary grief because they never pivoted from growth to how do I get my money out? 

[00:46:32] Joe: Yeah. How, how is it different? Because people are screaming that to their device right now, Roger. It 

[00:46:37] Roger: is different because you have multiple allocations you need to have when you are accumulating assets, you’re just trying to grow wealth.

That’s one pie chart of a portfolio. When you’re in retirement, you have multiple timelines that you’re planning for. The two big ones are how am I going to create my paycheck in the near midterm? And for me that’s five years. That is going to have a very different allocation than the money that is for my five year plus year old self.

Like we’re business owners. A lot of us are business owners here. I have a payroll reserve in my business, so I can meet payroll well in retirement. We need to have that if we need money from our capital. And I would argue that the first five years of what you need to take from your money needs to be not at risk and maturing when you need it because that’s your payroll.

That’s how you’re gonna pay your life. Then we have an allocation that’s more traditional trying to battle inflation long term. Still 

[00:47:34] Joe: getting, realizing you’re not gonna spend all the money today. Yeah. 

[00:47:37] Alissa: I love what you touched upon, and I think along those lines, I’m always someone who focuses on simplifying the finances, and I think at that point of your life, like you said, your season is.

It’s really important to simplify it too, because you’re not gonna live forever. And if someone inherits it, I’ve experienced with clients who’ve inherited money that it’s overwhelming for them to, first of all just have the loss, and then on top of it, when you have things all over the place, it’s really a lot for them to deal with and it’s harder for them to think about selling things and rebalancing and just.

It’s just a lot, just between the emotions and then a lot of them don’t have the experience. So I love that idea of simplifying all the time, but especially at that point of your life. And also recently we’ve been looking for senior living. Independent senior living for my in-laws. And it made me realize that it is really important, like you said, to declutter what you have too.

And think about if you want this ideal life, whether maybe you want to be an independent living, maybe you wanna live on your own, how do you get there? Because if you don’t wanna do independent living, ideally you would live someplace where it would be easier for you to live on your own, because otherwise you can really be pushed to do something.

Right now, you know you don’t wanna do, so why not look towards that because we’re so talk, you know, talking about the financial part, which is definitely important, but there’s also the emotional part and preparing. So you’re living where you could possibly stay and live forever. 

[00:49:16] Joe: The emotional piece is the one that gets me in all the studies showing that the more your retirement is like a, uh, a job, like a job that you love often creates, uh, much more longevity.

It’s a whole fascinating topic that’s for a different day. I love this guys. Looking at the different eras. This is, uh, Alyssa. I’m gonna try to copy what you did and say you guys had a lot of style. How about style? That’s my, probably my favorite Taylor Swift song and, um. This was quite a love story with all of you.

How about that? No. No. Maybe not. 

[00:49:50] Alissa: Yes, absolutely. 

[00:49:52] Joe: Alright, on that note, 

[00:49:54] Alissa: let’s, uh, 

[00:49:55] Joe: let, let’s do one thing that we didn’t do here. Doug. 

[00:49:57] Alissa: Doug. Oh. We need a bracelet from you, Joe, one of those friendship bracelets. We totally do. 

[00:50:02] Doug: If, if we’re almost wrapping up here, Joe, I think the appropriate, uh, Taylor song would be out of the woods.

[00:50:10] Joe: Very well, very well. We did not say hi to the people hanging out with us live on YouTube. We got here a little late today. I apologize. I totally misread the time and luckily brought Roger Whitney with me as, as, as well. Uh, Carlos is here. B in California is joining us. Carlos is in North Carolina. Dan is here.

Margaret’s in Atlanta. Dan’s in Seattle. Paul is here from down in College Station where OGs gonna be spending some time here in the near future. And, uh, Rocky is here. Rocky says, uh, Doug Peak bod was, was in your twenties, so you had to, you had to be good in the swimsuit. Then I. 

[00:50:48] Doug: Was 

[00:50:48] Joe: he 

[00:50:49] Doug: scoping me out in my twenties?

I don’t understand. 

[00:50:51] Joe: Going way back, you had talked about you might look at in a bathing suit. Thought is 

[00:50:54] OG: right now. 

[00:50:55] Joe: Yeah, I mean, I’ll go topless 

[00:50:58] Doug: if you want me to. 

[00:50:59] Joe: Peter’s here says great lineup here. Uh, Matt was cheering for team Paula. So Alyssa, nice job. I. There, Margaret also gave you a high five and lots of fun.

Also, hi to Adam. Glad that you guys hung out with us today. If you wanna hang out with us, normally we’re here at about, uh, 4:00 PM Eastern Time on, uh, Wednesday’s recording shows, uh, ish I should say for, for today. Alright, uh, let’s find out what, uh, each of you are doing. Og now that you devoured a bunch of stuff.

Last week with the masters, I saw that package. You got to simulate the masters in your house. Oh.

[00:51:36] OG: I’m glad you noticed. It’s a simulate, a masters show, Joe, 

[00:51:39] Joe: that box was full of a bunch of stuff. Holy, uh, what,

what? It’s getting worse. I know. I can’t, I can’t und dig the hole. What’s, uh, what’s going on in your life, og? 

[00:51:54] OG: Oh, this weekend is absolutely jam packed. I leave on Wednesday. I am out of town Wednesday, Thursday, Friday, a little af like three day after school activity this year. I’m kind of doing a whole bunch of stuff all at one time as opposed to spreading it out over the spring.

[00:52:09] Roger: Yeah. 

[00:52:09] OG: And uh, traveling to Louisiana and then Houston and then back to Fort Worth and, um, kind of doing a round robin after school activity type of, uh, weekend. But I’ll be home by, um. Noon on Friday, so it works out. No, that’s not bad. Yeah, 

[00:52:22] Joe: that’s fantastic. How might not 

[00:52:23] OG: by your house on the way to, uh, Louisiana?

[00:52:25] Joe: Fantastic. Come on down. That’ll be fun. We’ll go get some barbecue. I’m Come 

[00:52:28] OG: over, 

[00:52:30] Joe: get barbecue. 

[00:52:30] OG: Don’t get barbecue. I live in Dallas. 

[00:52:32] Joe: Naaman’s. You’ve had nayman’s. It’s pretty darn good. It’s not that great. Whatever. Alyssa. Alyssa, thanks for hanging out with us. Weird. What’s, and, and by the way, for taking it seriously, the, the Taylor Swift piece of this seriously nice work.

Uh, what’s going on? Amplify my wealth right now. 

[00:52:49] Alissa: Well, I’m gonna share what I’m doing personally since Josh did. Yeah. Um, my son is coming home for a few days, so I’m really excited for that. And then like you heading to Boston in just a few weeks for my other son’s graduation. And then I also applied to, um.

Apartment, sit for my older son while he travels for work. So I’ll be staying in his apartment, making sure it’s okay in Manhattan. So I’m really excited for that too. 

[00:53:20] Joe: Oh, oh, I got nice. I was like, there’s gotta be something going on there. Oh, in Manhattan? Yes. Making sure everything’s okay. 

[00:53:28] Alissa: Yeah. I wanna make sure, you know, his apartment’s not empty.

Like who knows what’s gonna happen. So while he’s gone, I, all of a sudden it hit me that he’d be gone. The. After the graduation and I’m gonna be in Boston, like that’s not too far. So I asked him if anyone has applied for the position yet, and he laughed and said, I guess he wants stay in the apartment. I said, I guess, and then I said, I’d also like write a first refusal moving forward.

And we’re in. 

[00:53:56] Joe: Sounds like you’re negotiating contracts, Alyssa. The uh uh, uh, somebody’s gotta make sure that those restaurants keep moving while he’s outta town. I mean, somebody has to. 

[00:54:05] Alissa: The sidewalks. Someone’s walking on them. I, I’ve got it covered. 

[00:54:09] Joe: Somebody’s got to, that’s incredible. Roger, what’s going on at the Retirement Answer Man Podcast man.

[00:54:15] Roger: Right now we’re hanging out talking about the basics ’cause it’s easy to get geeked out on things. We’re ba talking about the basics of asset allocation and fixed annuities and things like that. And I am living my. Late mid-life to the fullest. We’re the first year that we’re in Colorado for the entire summer.

Is it snow behind you? Is there snow there? It is not snow. Hey Sherlock. My dog just came downstairs. Hey buddy. Hey buddy. Uh, it is not snow, but we’ve had, I got snow in the mountains over here, so hanging out here. Gonna go mountain biking this weekend. 

[00:54:47] OG: Hey Roger, if you’re trying to tell your dog not to hoop somewhere, what do you say?

What do you say, Josh? I don’t know. No, I’m just asking. Do you say like. No Sherlock. No. 

[00:55:03] Roger: You actually came up with that on the fly, which is really impressive. After those two alters you’ve had over the last hour. Incorrect 

[00:55:09] OG: sir? Three. Ultras. Three. Three. Josh 

[00:55:14] Joe: does get 

[00:55:14] Roger: funnier 

[00:55:15] Joe: as he gets drunker. I do know this.

And uh, and scene. Alright, we’ll link to that was pretty good, I thought. Great. I can’t 

[00:55:24] OG: believe anybody, nobody else thought of that or right away. That was pretty solid. That was pretty good. We’ll 

[00:55:27] Joe: link to all of, uh, Alyssa’s amazing stuff. And Rogers on our show [email protected]. Guys, thank you so much for helping us round out Taylor Swift Week.

Doug, you got it From here, man. Bring us home. What should we, what should we have learned today? Can 

[00:55:43] Doug: you let me stop laughing about OGs joke before I Good. Get this. It was 

[00:55:48] OG: good. I thought that was pretty clever. Honestly, 

[00:55:49] Doug: that was, it was high quality stuff. That was too shelf humor. We’re not used to that 

[00:55:53] OG: here.

Thanks buddy. 

[00:55:55] Doug: All right, here’s, here’s what I think people should take away. First. Take some advice from og. You need to build your foundation when you’re in your teens, if you wanna have any shot in hell to retire comfortably. Did I get that right? Og? Is that pretty much what, what you were trying to say?

[00:56:09] OG: No, I said, uh, you can build the foundation, but if you pull a Peter. You still have plenty of time in your forties to get it done. Ah, 

[00:56:16] Doug: okay. Alright. Sorry, I messed that one up. Uh, second. Roger said three exactly three incredibly smart things today. One of ’em was about segmenting your money for different phases of your life.

Can you summarize that for us again, Roger? And like, explain it like I’m five, I’m like a shark. 

[00:56:34] Roger: I forgot, I forgot what I said. Go back to the tape. Okay, thanks. You’ve been very helpful. 

[00:56:42] OG: Well, we don’t have to worry about welcoming him back ever again.

[00:56:49] Doug: Okay, well, he had a cup of coffee in the bigs. I hope he enjoyed it. Glad the big lesson. We can all, we can all learn a lot from Superman, for instance, wearing your underpants on the outside of your pants is a great way to reduce your laundry loads. Thanks to Roger Whitney for joining us today. Wanna learn more about him?

Check out the Retirement Answer Man podcast. We’ll also include links in our show [email protected]. Thanks to Melissa Maes for putting up with us today. Check her [email protected] to learn more. And finally, thanks to OG for. Blessing us with his presence, looking for good financial planning, help head to stacking benjamins.com/og for his calendar.

It’s getting harder and harder to say our URL in different ways. Change the emphasis. This show is the Property of SP podcasts, LLC, copyright 2025, and is created by Joe Saul Sea. Hi, Joe gets help from a few of our neighborhood friends. You’ll find out about our awesome [email protected] along with the show notes and how you can find us on YouTube and all the usual social media spots.

Come say hello. Oh yeah, and before I go. Not only should you not take advice from these nerds, don’t take advice from people you don’t know. 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.