
Smart money strategies that evolve as your life—and goals—change.
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Joe Saul-Sehy
This episode is brought to you by.
Navy Federal Credit Union
Navy Federal Credit Union. We know how fast life moves. That's why we have all in one banking to let you keep on banking on by saving time and money and getting a full picture of all your finances plus whether you have credit or not, you can build your credit score with the new ability to report on time bill payments. Learn how you can keep on banking on@navy federal.org Navy Federal Credit Union. Our members are the mission. Insured by NCUA Small business owners State.
Joe Saul-Sehy
Farms there with small business insurance to fit your specific needs. Whether you're starting a new venture or growing an existing one, State Farm helps you choose the right coverage to protect what matters most. Working with a local state farm agent helps you understand your coverage options. Offering local support to help you achieve your goals. Focused on turning your passion into a thriving business. Knowing your insurance can change as your business grows. Stay Farm here to help you succeed with your business. Like a good neighbor. Stay Farm is there. This your place?
Doug
No, no, no, no, no, no, no.
OG
I live with my mom.
Doug
Oh, yeah. You hungry?
OG
Hey ma. We get some meatloaf.
Joe's Mom's Neighbor Doug
Live from the basement of the YouTube headquarters, it's the ST Show. I'm 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 want to 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 Jo Saul. Sehist.
Joe Saul-Sehy
Go to Doug. We just go challenge, correct? Absolutely. Everybody, Happy Friday. I am Joe Salsi. Hi. Average Joe. Money on 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?
OG
Cheers.
Joe Saul-Sehy
Put on my glasses so I can see. What are you pouring?
OG
Apple juice.
Joe Saul-Sehy
Gotcha.
OG
In a blue can into a little mug, little foamy apple juice.
Joe Saul-Sehy
Cleverly, you know Anybody thinking that you're actually drinking apple juice, so you disguise it as a nickel.
OG
Disguise it as a beer. Yeah. Everybody knows you can't drink beer on camera. So this is. That says Shane Gillispet, you know, with. When they're doing the Bud Light commercial. Have you seen that?
Roger Whitney
Yes.
OG
Him and Post Malone, they're like, you can't drink. You can't do it.
Joe Saul-Sehy
You can't.
OG
You just can't do it.
Joe Saul-Sehy
The three, two, one, two.
OG
And then, like. And then they're done. So this is in celebration of Masters tournament. These are my masters mugs.
Joe Saul-Sehy
Oh, look at those. Yeah, nice. Masters happened last Friday, last weekend, or.
OG
It'S happening right now, depending on. Depending on how you think about time and the construct of. Of the human experiment.
Joe Saul-Sehy
The miracle of. The miracle of the recording. And the woman who's like, man, I should have been on my third Mick Ultra based on just trying to get this rolling from, amplify my wealth. Alyssa Mays, financial planner is here. How are you?
Alyssa Mays
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.
Joe Saul-Sehy
Yeah, we were having a good time backstage. But tell everybody about what you do there in South Florida.
Alyssa Mays
I'm guessing you're thinking financially, but I'll also talk about. I'm thinking, like, what I do in Florida. I don't have a beer.
Joe Saul-Sehy
Water ski.
Alyssa Mays
I 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. I have lots of family up there. And also Boston. I know we're both going to be in the same neck of the woods.
Joe Saul-Sehy
Soon, so maybe we'll get graduation season up in Boston.
Alyssa Mays
Yeah, exactly.
Joe Saul-Sehy
And the gentleman who woke up from his nap to join us, it's the retirement answer man. Roger Whitney's here. How are you, brother?
Roger Whitney
This is what's wrong with America. Men don't drink beer anymore. What is that? Is that colored water? Make a little. Get a good ipa, buddy. Come on, og. It's good to be here. Now that I'm awake. There we go. There we go. That's what I'm talking about. Doug. Yeah.
Joe's Mom's Neighbor Doug
Yeah.
Joe Saul-Sehy
Doug's drink.
Joe's Mom's Neighbor Doug
Those aren't beers, little scooch.
Joe Saul-Sehy
Yeah. Doug's drink isn't a beer. It's a sample he did for his doctor that he shot.
Alyssa Mays
I thought it was like, a little.
Roger Whitney
Cups from down there. He did pull it up from down there.
Alyssa Mays
So I'm happy someone said that.
Joe Saul-Sehy
We have been talking Taylor Swift all week. We had 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 going to use Taylor as 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 20s 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 going to talk about the three eras of investing today. We're going to do our own eras tour, but ours is going to 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 going to hear from them and then we're going to talk eras of investing. So let's get the party started. This episode is brought to you by.
Navy Federal Credit Union
Navy Federal Credit Union. We know just how fast your life moves. You've bills to pay, mouths to feed and not a lot of free time. That's why we created an all in one banking experience that lets you keep on banking on. It can save you time and money with new lightning fast direct deposit setup and it offers checking accounts with ATM refunds and no service fees. Plus, whether you've credit or not, you can build your credit score with the new ability to report on time bill payments and with personalized financial insights on my making sense, the ability to view all your accounts in one place, custom notifications and 247 fraud protection, you can get a full picture of your finances. So if you want an all in one banking experience that lets you keep on banking on, sign up today. Learn more@navy federal.org Navy Federal Credit Union Our members are the mission insured by NCUA Small business Owners.
Joe Saul-Sehy
State Farm's there with small business insurance to fit your specific needs. Whether you're starting a new venture or growing an existing one, State Farm helps you choose the right coverage to protect what matters most. Working with a local State Farm agent helps you Understand your coverage options, offering local support to help you achieve your goals. Focus on turning your passion into a thriving business. Knowing your insurance can change as your business grows. Stay Farm here to help you succeed with your business. Like a good neighbor, Stay Farm is there. 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?
Alyssa Mays
I love one of the things that she deals with, which is stickiness. And it's kind of counterposed because I'm going to also use the lyric to go with that. So when you think about what's going on 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 going to say another lyric, sorry, Joe, but you put the Taylor Swift out there, so bring it. You're on your own. The 20s and 30s, 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 20s and 30s, they're not necessarily thinking about automating and maxing out their retirement. Instead, 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.
Joe Saul-Sehy
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 Jonathan Clements, and Jonathan was saying, you really have two roads you can go down. You can. Number one, you can play in your 20s 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 of 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 going to give people advice in their 20s, which of those options do you think is the one they should probably take?
Roger Whitney
I actually think option three is the best option, 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, because 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 is 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 401s and Roth IRAs and all of those other things.
Joe Saul-Sehy
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 Alyssa said, you know, hey, decide which way you're going to go. But really what Roger said is interesting. This might be a time to invest in yourself. Yeah.
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 going to 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 Ramsey's 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? Because in your 20s, you might not know what that looks like. And so I think it's important to experience a bunch of different things. But you don't want to have all the experiences and then be 30 and have $100,000 worth of debt because you're like, I was finding myself and doing experiences, and I went and got three degrees and 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, $166.67 a month, right? Everybody remembers that who's been around for a while. 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 5? 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. And I think it's a little bit of fun, too, in moderation. So all of those things.
Joe Saul-Sehy
I like what you said about automating, because 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 around a specific one specific tactic you think somebody starting out should have?
OG
I pick automation.
Joe Saul-Sehy
That they do.
Roger Whitney
I was going to pick that.
Joe Saul-Sehy
You already took that one. So, Alyssa, what is another tactic, a specific one tactic that somebody just starting out should learn and begin doing?
Alyssa Mays
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 going to end up with great success. Either you're not going to 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.
Joe Saul-Sehy
I like the idea of budgeting in your fund because, I mean, too often in my 20s, 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.
Roger Whitney
I think 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 want to 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 going to be disciplined to make the Roth contribution or to spend money on fun. I think that's 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 got to do that.
Joe Saul-Sehy
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, 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 maybe a tactic that you could have Learned in your 20s or maybe, maybe did in your 20s. That was good stuff.
Joe's Mom's Neighbor Doug
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 experiences. Instagram is ruining a generation because everybody feels like they've got to 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? How about you just. Just really focus on getting good at an early age at a specific skill set 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 20s is kind of infuriating.
Joe Saul-Sehy
I don't think it's inferior at all. I really do agree, like I opened this up with, with Jonathan Clements, is you have a choice. I mean, you do have a choice. Just realize that you have a choice and you're going to pay for it. You're going to pay for it either way.
OG
Well, I 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.
Joe's Mom's Neighbor Doug
Right?
OG
You know, they don't recognize the choice. Prefrontal cortex isn't fully developed yet.
Roger Whitney
Be great at what you do. And just for the record, Doug, I actually said that one too. So I just want to mention that.
Joe's Mom's Neighbor Doug
I know I just, I started to get dizzy when you were saying all of the words and I just couldn't keep them all straight.
Joe Saul-Sehy
My point would be, because I really like Alyssa's to put a number on your fun. 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 20s to get caught up in what everybody else was doing and whether I really truly enjoyed spending that money or not. Because you know 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.
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 back end. 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 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 saw an article about, 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. And it was expensive when, you know, when we're. We all had that emotion of like, how the hell am I going to 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 whatnot. That doesn't make our way right or wrong. But I'm just saying, 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 is really cool. I should be doing that. It's like, dude, you need a cash reserve, man. Like, you need to be saving 250amonth 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 get through it, but I guess just don't be in such a hurry, maybe, is the good way to summarize that.
Joe Saul-Sehy
Yeah, we talked about.
OG
It'll come. Don't worry.
Joe Saul-Sehy
I like that callback to earlier in the week where he talked about enjoying the process, about. It becomes clear Taylor Swift really likes writing songs.
OG
You know, like, you're not going to get the best job right away. Your boss is going to be a jerk. Maybe you're going to get passed over for promotions. You're going to be overqualified or under qualified. Like, that stuff happens. Like, that's just. That's just life.
Joe Saul-Sehy
Alyssa. What's another thing people starting out worry.
Alyssa Mays
About too much, what other people think. I think that there's so much of that, whether it's you are friends with people or relationships with people because of what other people might. What you think they're going to 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 was going out all the time. I mean, I used to like going out in my 20s, and I probably didn't put a lot of. But 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 want to do. Don't do it because 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 want to be a part of a group and feel accepted, but just because 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 want to be.
Joe Saul-Sehy
Yeah, everybody has debt. I mean, come on. Everybody's got debt and everybody whips out their credit card and you think that they probably.
OG
Water's warm. Jump on in, Roger.
Roger Whitney
I actually had a podcast. I. I recorded a couple pilot episodes called I Love Debt, and it was going to be a parody. We had the. We had the debt rules. I think I still have the T shirt for it, but it never.
Joe Saul-Sehy
I remember what you and our friend Vincent Puglisi at a conference had brainstormed that. I think after a couple of those MC Ultras.
Roger Whitney
Yes, maybe I. I'm gonna agree with Alyssa here on. It's that Jim Rome quote.
Joe Saul-Sehy
Right.
Roger Whitney
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. And you, Joe, is that there are so many counterfeit experts out there that 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.
Joe Saul-Sehy
I wanted to spend a little extra time with people just starting out because I think that's really important. Obviously it's going to be important for people that are in the middle of their journey. We're going to spend a little time on that. But also of course, for people that are in retirement. We're gonna do that after the break. But at the near halfway point, this would 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 contributors, OG Jesse Kramer and Paula pant fighting over this year long worthless. Well, dollar store trophy that is not worthless. Is that it back there? There it is. There's the dollar store. Dollar store trophy. Just to keep things really easy. Well, of 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?
Alyssa Mays
Yes.
Joe Saul-Sehy
All the above. Well, the I guess the good news is, is that this is the same place. Cause you've played for Paula before. Paula's in last place, which is no change, no different. 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 you're team Jesse, you get your guessing second. OG Is guessing first. And 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.
OG
What's the score? Sorry, I wasn't score for all that.
Joe Saul-Sehy
Yeah, he just wants me to say it again. OG is 5. Jesse 3.5. Paula 1.5 points. Doug's got this week's trivia. Does it have anything to do with Taylor Swift?
Joe's Mom's Neighbor 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. Because it is not easy. Hey there, Stackers. I'm Joe's mom's neighbor, Doug, and what a Superman Taylor Swift is. I mean, superwoman. Well, I don't need to tell you because you've been learning from her career all week. So while we're 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 2020 14, 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 underoos. Should be wearing those for this.
Joe Saul-Sehy
Absolutely. Doug's gonna go get those. OG 2014 Action Comics number one. What did it sell for?
OG
Is that the one with Spider Man?
Joe Saul-Sehy
He just said it's with Superman.
Joe's Mom's Neighbor Doug
He literally just said Superman.
Roger Whitney
Dude, Superman, where are you?
OG
Okay, Superman. All right, well, that's different. Then I heard man, and I heard a word that started with an S. I just want clarification. And when was the comic first produced? Is that a known? Known.
Joe Saul-Sehy
I don't think we gave you that information.
Joe's Mom's Neighbor Doug
We did not give you that information. It's not necessary for you to provide an answer.
OG
False.
Roger Whitney
Are you going to ask him to use it in a sentence now?
OG
So a really good comic with Superman and this was sold at auction and it was like a mint copy.
Joe Saul-Sehy
Mint copy.
Joe's Mom's Neighbor Doug
Most expensive copy in existence.
Joe Saul-Sehy
Most expensive sale ever of a comic book.
OG
Okay, so this is like a Babe ruth baseball card. $4 million.
Joe Saul-Sehy
$4 million. Roger, what do you think about that?
Roger Whitney
2.4 million.
OG
No, he just went right to it.
Joe Saul-Sehy
He just thinks 2.4 million. So you think he's a little north of where he should be?
Roger Whitney
Josh is always high.
Joe Saul-Sehy
Interpretations. Alyssa, you've got 4 million and 2.4 million. What do you think?
Alyssa Mays
3.6.
Joe Saul-Sehy
3.6. So you're going to kick a field goal right between the two of them. All right, we've got OG at 4 million. Alyssa, 3.6. Roger at 2.4. Who's right? Is Alyssa going to help team Paula get closer to team Jesse? And Roger, Is Roger gonna help Jesse Put pressure on og. We'll find out in a second.
Doug
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Joe Saul-Sehy
Oh gee. You kicked it off with $4 million and both Alyssa and Roger said no. I think that might be a skosh too much money. What do you think?
OG
No idea.
Joe Saul-Sehy
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?
Roger Whitney
I feel great. And I'm horrible at this trivia. I'm so glad that I can contribute this time.
Joe Saul-Sehy
And Alyssa, you're right up the middle there with 3.6. Feeling good?
Alyssa Mays
No, but I figure, I mean, Paul will be happy if I won and if not, well, that's right, the same place as before.
Joe Saul-Sehy
Paul's already in last. Well, let's see if Melissa is going to maybe give Paul a big win. Roger gonna get a big win. Oh gee, Doug, what's our answer?
Joe's Mom's Neighbor 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. Tim. 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 value 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 winner here.
Joe Saul-Sehy
How about that? Alyssa bringing home the win. Nice job.
Roger Whitney
You gonna make an acceptance speech?
Joe Saul-Sehy
Victory speech. Wow.
Alyssa Mays
I'm happy to help Paula, and I'm shocked that I won.
Joe Saul-Sehy
Roger, would you say you'd never win?
Roger Whitney
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, because I think she was the one that I didn't help last time.
Joe Saul-Sehy
Well, this time you helped 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 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 starting?
Roger Whitney
I'm ready, man. Two things. Number one is you're starting to finally make some money because you're. You have a reputation that you know you can actually work well. So you need to control your lifestyle creep. Just because you're starting to make some money doesn't mean it's going to go up forever. Life will hit you in the face.
Joe Saul-Sehy
Our lifestyle creep, Doug is the creep. Doug is that we're talking about. Got to keep him controlled.
Roger Whitney
I was looking at him, but. And that second is now is the time to start positioning yourself to maximize income. Because 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 want to start working on 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.
Joe Saul-Sehy
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'm positioning for max income. We've got Lorraine Lee joining us next week. We're going to 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 her 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 because you haven't thought about it at all.
OG
Sucks.
Roger Whitney
And just never use the phrase thought leader, please.
Joe Saul-Sehy
Inside the box, outside the box, planning, win, win. Oh, gee. What would you like to add to what Roger said about mid career, mid portfolio growth? Things we need to think about?
OG
Well, I guess I'm thinking, is this person done the right stuff? Up to this point, you got to give me some little context. So this person, I don't know, is.
Joe Saul-Sehy
It time for a checkup? If we haven't. I mean, what's the ying yang there?
OG
I think it depends. So two things. I'm thinking about a person who maybe just kind of wakes up and goes, oh, crap. Oh, I party, too. 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 maybe he 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 20s, I didn't do this stuff. 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. Are you going to 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 that you don't have to swing for the fences. And I think the problem is people think, oh, crap, I don't have any time at all. So I'm going to make all these radical things. I'm going to try to do all this aggressive stuff. I'm going to day trade penny stocks. I'm going to try to do all these things to get caught up. And you don't need to. You have so much time still.
Roger Whitney
Join Gamway representative. Right. All these extras, you're going to be.
OG
A little behind the gal who started when she was 20, but 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, oh, 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. You know, sometimes you look at your budget as a great example. Roger says, anti budget. 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.
Roger Whitney
That is so well said, Josh. I literally lived what you talked about in terms of partying too much, thinking I was all that, and then having to clean up my mess. Yeah, there is enough time.
OG
You have a ton of time. Yeah. I mean, do you get to retire at 50 and also party all your 20s and 30s? No, you don't. You just don't. I mean, that's not going to be you. Can you do it at 65? Absolutely. Plenty of time. 25 years is a long time.
Joe Saul-Sehy
Yeah. I like the idea of just taking a breath. You know, you guys have both said that you're anti budget, 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.
Alyssa Mays
Okay, Just along those lines. First of all, a Taylor Swift line, because that's why you got to do it.
Joe Saul-Sehy
You got to do it.
Alyssa Mays
I just have to 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 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 going to have enough for ret 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 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 going to have enough for retirement, it might look a little different now. Maybe you just need to adjust your way of living so you could still retire when you wanted to. So I definitely think a little paranoia is good, or maybe cautiousness, whatever you want to call it, and make sure that you're staying on track so you don't wake up one day wishing, because 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.
Joe Saul-Sehy
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 going to ask you guys what they shouldn't do because, oh, gee, I really like your. Your kind of got this question all the time, you guys. All three of you must get this question all the time. My head or behind? Am I ahead of other people? My 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 to pivot, though, to people those last five years of retirement into their retirement years. Oh, gee, let's have you start this round. We're at retirement.
OG
We're landing the plane.
Joe Saul-Sehy
We're landing the plane. What is the thing? What is one thing we really need to focus on that we didn't need to focus on during those other two.
OG
Areas is, well, again, I'm just going to try to create a person in my brain here that's five years out, that's maybe done an okay job of this stuff. I think now is a good time to start thinking about where the cash flow is going to come from if you've been a really good saver for your entire life. In my experience, anyway, good savers don't turn into good spenders. I'm a great spender. So the opposite is also true. I have. No, no, no, not, no.
Joe Saul-Sehy
I have a great scoreboard. Scoreboard. I'm a great spender.
OG
No, no, I'm an expert spender, especially of other people's money. 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 spender is not super easy to do. So I think starting to think about, like, where that cash flow is going to come from and starting to see how you build that cash flow out for the first few years of your financial independence. Time, 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 want to retire at 57. Uh, oh, you know, now we have a little problem to solve. How am I, you know, do I save? Do I stop doing 401 contributions for the next five years and just put it in brokerage so that I've got some flex? 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 Going to pay myself five years from now. From a cash flow standpoint, if you build that out, it gives you an opportunity to kind of see where the pitfalls might be.
Alyssa Mays
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 for people who are near retirement or in retirement except 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 60s and they were determined, they realized that they were not going to be prepared to ever stop working. And, and they've even said inspirational things that you can do something. These are people who initially had no hope and turned it around. And you know, it might be reframing, but the other thing is, and of course my last Taylor Swift thing, because I get it out there, I'm not even a swiftie, but I'm like you told me, I just follow directions.
Joe Saul-Sehy
Okay, you understood the homework?
Alyssa Mays
Yeah, I did. This one is I come back stronger than a 90s 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. Because that's how people end up not being where they want to be is they see what other people are doing. Are they yet nervous? So you're like, if you're invested in the market, like Josh said, it's good if you want to 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 want to do that. But also make sure you consider your risk tolerance before you invest in 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.
Joe Saul-Sehy
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. Super aggressive. I'm super aggressive and I'm like, you don't come across super aggressive. No, I'm great. I'm great. They were always the first people on the phone to me when the market started going down. What are we gonna do? 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. Roger, give us one for the other side. Both Alyssa and OG Talk to the, you know, five years before you retire. What's something people need to really focus on when they're in retirement with their money that they didn't need to focus on before that?
Roger Whitney
Before I share my word salad, Doug, would you. Do you have anything you'd like to say first?
Joe's Mom's Neighbor Doug
I appreciate that opportunity. That was very considerate of you, Roger. And I will.
OG
It's Ro.
Joe's Mom's Neighbor Doug
I will cede my time to the senator from the mountain time zone.
Roger Whitney
Overcoming frugality is definitely a big one of them, 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 50s 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 as well.
Joe Saul-Sehy
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 spent a lot of time, Roger, talking about how we're going to build up our portfolio, but not nearly enough think about how we're going to. How we're gonna. I was gonna say deconstruct, but you know what I mean, how I'm gonna start de.
OG
Accumulate decumulate yeah.
Roger Whitney
And literally the strategy is very different than accumulation decumulation. Investment decisions are very different than accumulation decisions. And many of us aren't aware of that. And for those of us that have been blessed to be good accumulators because we built the habits. It's like those guys 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?
Joe Saul-Sehy
Yeah, how, how is it different? Because people are screaming that to their device right now, Roger.
Roger Whitney
It's 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 going to pay your life. Then we have an allocation that's more traditional trying to battle inflation long term.
Joe Saul-Sehy
Still getting realizing you're not going to spend all the money today. Yeah.
Alyssa Mays
I love what you touched upon and I think along those lines I'm always someone who focuses on simplifying the finances. 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 going to 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. That'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 want to live on your own. How do you get there? Because if you don't want to 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 that right now, you know, you don't want to do. So why not look towards that? Because we're so, 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.
Joe Saul-Sehy
Yeah, the emotional piece is the one that gets me. And all the studies showing that the more your retirement is like a, a job, like a job that you love often creates 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 Alyssa. I'm going to 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 this was quite a love story with all of you. How about that? No, maybe not.
Alyssa Mays
Yes, absolutely.
Joe Saul-Sehy
All right, on that note, let's. Let's do one thing that we didn't do here, Doug.
Alyssa Mays
Oh, we need a bracelet from you, Joe. One of those friendship bracelets.
Joe Saul-Sehy
We totally do.
Joe's Mom's Neighbor Doug
If we're almost wrapping up here, Joe, I think the appropriate Taylor's song would be out of the Woods.
Joe Saul-Sehy
Very well. Very well might be. 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 well. 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 OG Is going to be spending some time here in the near future. And Rocky is here. Rocky says Doug Peak bod was. Was in your 20s, so you had to, you had to be good in the swimsuit then.
Joe's Mom's Neighbor Doug
Was he scoping me out in my 20s? I don't understand.
Joe Saul-Sehy
Going way back, you had Talked about you might look good in a bathing suit.
OG
That is right now.
Joe's Mom's Neighbor Doug
Yeah, I mean, I'll go topless if you want me to.
Joe Saul-Sehy
Peter's here, says great lineup here. Matt was cheering for Team Paula. So Alyssa, nice job 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 want to hang out with us normally we're Here at about 4:00pm Eastern Time on Wednesdays recording shows. Ish. I should say for. For today. All right, let's find out what 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 of your house.
OG
I'm glad you noticed.
Joe Saul-Sehy
To simulate the masters. That box was full of a bunch of stuff.
OG
Holy.
Joe Saul-Sehy
What?
OG
It's getting worse.
Joe Saul-Sehy
I know. I can't. I can't undig the hole. What's. What's going on in your life?
OG
OG oh, this weekend is absolutely jam packed. I leave on Wednesday. I am out of town. Wednesday, Thursday, Friday, a little 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.
Joe Saul-Sehy
Yeah.
OG
And traveling to Louisiana and then Houston and then back to Fort Worth and kind of doing a round robin after school activity type of weekend. But I'll be home by noon on Friday, so it works out.
Joe Saul-Sehy
That's not bad. Yeah, that's fantastic.
OG
I might stop by your house on the way to Louisiana.
Joe Saul-Sehy
Fantastic. Come on down. That'll be fun. We'll go get some barbecue over.
OG
I don't get a barbecue. I live in Dallas.
Joe Saul-Sehy
That naming's you've had naming, it's pretty darn good.
OG
It's not that great.
Joe Saul-Sehy
Whatever. Alyssa. Alyssa, thanks for hanging out with us and by the way, for taking it seriously. The, the Taylor Swift piece of this. Seriously. Nice work. What's going on? Amplify my wealth right now.
Alyssa Mays
Well, I'm going to share what I'm doing personally since Josh did, 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 apartment sip 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.
Joe Saul-Sehy
Oh, oh. I got, I was like, there's got to be something going on there. Oh, in Manhattan. Yes. Making sure everything's okay.
Alyssa Mays
Yeah, I want to make sure, you know, his apartment's not empty. Like, who knows what happens. So while he's gone, I. All of a sudden it hit me that he'd be gone the week after the graduation and I'm going to 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 you want to stay in the apartment. I said, I guess. And then I said, I'd also like write a first refusal moving forward and wherein.
Joe Saul-Sehy
Sounds like you're negotiating contracts, Alyssa. The Somebody's got to make sure that those restaurants keep moving while he's out of town. I mean, somebody has to.
Alyssa Mays
And the sidewalks, someone's walking on them. I've got covered.
Joe Saul-Sehy
Somebody's got to. That's incredible. Roger, what's going on at the retirement Answer man podcast, man?
Roger Whitney
Right now we're hanging out talking about the basics because it's easy to get geeked out on things. We're talking about the basics of asset allocation and. 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.
Joe Saul-Sehy
Is there snow behind you? Is there snow there?
Roger Whitney
It is not snow. Hey, Sherlock, my dog just came downstairs. Hey, buddy.
Joe Saul-Sehy
Hey, buddy.
Roger Whitney
It is not snow, but we've got snow in the mountains over here. So hanging out here. Gonna go mountain biking this weekend.
OG
Hey, Roger, if you're trying to tell your dog not to poop somewhere, what do you say?
Roger Whitney
What do you say, Josh? I don't know.
OG
No, I'm just asking. Do you say like, no, Sherlock.
Roger Whitney
You actually came up with that on the fly, which is really impressive after those two ultras you've had over the last.
OG
Incorrect, sir. Three ultras.
Roger Whitney
Three. Josh does get funnier as he gets drunker. I do know this.
Joe Saul-Sehy
And. And scene. All right, we will link to.
OG
Pretty good, I thought. I can't believe anybody nobody else thought of that right away. That was pretty cool.
Joe Saul-Sehy
Link to all of Alyssa's amazing stuff and Rogers on our show notes page@stackingbenjamins.com. 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?
Joe's Mom's Neighbor Doug
Can you let me stop laughing about OG's joke before I get into this?
OG
I thought that was pretty clever, honestly.
Joe's Mom's Neighbor Doug
It was high quality stuff. That was good Shelf humor. We're not used to that here.
OG
Thanks, buddy.
Joe's Mom's Neighbor Doug
All right, 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 want to have any shot in hell to retire comfortably. Did I get that right, OG Is that pretty much what you were trying to say?
OG
No, I said you can build the foundation, but if you pull a Peter, you still have plenty of time in your 40s to get it done.
Joe's Mom's Neighbor Doug
Ah, okay. All right.
Joe Saul-Sehy
Sorry.
Joe's Mom's Neighbor Doug
Messed that one up. Second. Roger said three. Exactly. Three incredibly smart things today. One of them 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.
Roger Whitney
I'm like a shark. I forgot. I forgot what I said. Go back to the tape.
Joe's Mom's Neighbor Doug
Okay, thanks. You've been very helpful.
OG
We don't have to worry about welcoming him back ever again.
Joe's Mom's Neighbor Doug
Okay, well, he had a cup of coffee in the bigs. I hope you enjoyed it. But the big lesson, 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. Want to learn more about him? Check out the Retirement Answer man podcast. We'll also include links in our show notes@stackingbenjamins.com thanks to Alyssa Mazes for putting up with us today. Check her out@ampirmifymywealth.com to learn more. And finally, thanks to OG for blessing us with his presence. Looking for good financial planning help? Head to stacking benjamin's.comog for his calendar. It's getting harder and harder to say our URL in different ways.
Joe Saul-Sehy
Change the emphasis.
Joe's Mom's Neighbor Doug
This show is the property of SB Podcasts, LLC, Copyright 2025, and is created by Joe Saul Sehi. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome team@stackingbenjamins.com along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello.
Joe Saul-Sehy
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Joe's Mom's Neighbor Doug
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, Doug. And we'll see you next time back here at the Stacking Benjamin Show.
Podcast Summary: The Stacking Benjamins Show – "Building Wealth Through Every 'Era' of Your Life"
Release Date: April 18, 2025
Hosts: Joe Saul-Sehy and OG
Guests: Alyssa Mays (Financial Planner) and Roger Whitney (Retirement Answer Man)
In this engaging episode of The Stacking Benjamins Show, hosts Joe Saul-Sehy and OG delve into the concept of building wealth through the various "eras" of one’s life, drawing inspiration from Taylor Swift’s illustrious career. The episode is enriched with expert insights from financial planner Alyssa Mays and Roger Whitney, also known as the Retirement Answer Man. The hosts maintain their signature light and friendly tone, making complex financial topics accessible and entertaining.
Joe Saul-Sehy (02:22):
"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 want to win through all of your eras, don't you?"
The discussion centers around how Taylor Swift's ability to adapt and evolve her career serves as a metaphor for personal financial growth through different life stages. The hosts highlight that, much like Swift’s strategic shifts, investors must adjust their financial strategies as they transition through various phases of life.
Alyssa Mays (08:27):
"It's important to do something that resonates with you... make sure you have your own plan and your own way of implementing things that, of course, works."
Alyssa emphasizes the significance of creating a personalized financial plan that aligns with one’s values and circumstances. She advises young investors to “target what's untapped” and leverage the advantage of time to benefit from compound growth.
Roger Whitney (10:53):
"There is no need to choose one or the other. I think you can have a little bit of both if you're intentional about it, because it's all a matter of moderation."
Roger counters the notion of extreme savings versus enjoying life by advocating for a balanced approach. He introduces the concept of career capital, urging young professionals to build their reputations and invest in their skills to maximize future income potential.
OG (15:38):
"Set up so that you have automatic escalation, you know, every six months or every year."
OG underscores the power of automation in financial planning, recommending automatic transfers to savings and retirement accounts to ensure consistent growth without the need for constant oversight.
Midway through the episode, a fun trivia segment engages the team and audience. The question posed was:
"The most expensive comic ever sold first debuted on today's date in history. Action Comics Number One, featuring Superman, was sold at auction for how much?"
Participants—OG, Roger, and Alyssa—guessed varying amounts, with Alyssa ultimately winning by correctly estimating the sale price to be closer to the actual figure.
Alyssa Mays (35:03):
"I'm happy to help Paula, and I'm shocked that I won."
This segment not only adds entertainment value but also reinforces the episode’s theme of leveraging knowledge and strategy to achieve success.
Roger Whitney (35:52):
"You need to control your lifestyle creep... start positioning yourself to maximize income."
Roger highlights two critical aspects for individuals in their mid-career:
Joe Saul-Sehy (36:14):
"Lorraine Lee joining us next week... she's going to help people do that tactically, working on your career branding."
Future episodes will delve deeper into strategies like career branding, essential for mid-career professionals aiming to maximize their income potential.
OG (37:35):
"You have more time than you think... you don't need to make all these radical things."
OG reassures listeners that even if they feel behind in their financial journey, there is ample time to adjust and optimize their strategies without resorting to drastic measures.
Roger Whitney (48:11):
"Investment decisions are very different than accumulation decisions."
Roger explains the shift from accumulation (building wealth) to decumulation (spending and preserving wealth) as one approaches retirement. This transition involves:
Alyssa Mays (46:30):
"Check in on your finances... make sure you're staying on track so you don't wake up one day wishing."
Alyssa advises retirees to regularly review their financial plans to ensure they remain aligned with their lifestyle and spending needs, especially in volatile markets.
Roger Whitney (50:02):
"Simplifying that into one coherent plan makes sense as well."
Roger stresses the importance of simplifying financial portfolios in retirement to minimize confusion and ensure efficient withdrawal strategies.
Alyssa Mays (53:20):
"Declutter what you have too, and think about if you want this ideal life."
Alyssa incorporates the emotional aspect of retirement planning, encouraging retirees to declutter both financially and emotionally to create a fulfilling retirement life.
Joe Saul-Sehy (43:38):
"Fear can be a good thing if it's used well... it's all about just reaching your goal."
The hosts conclude by reinforcing the importance of aligning financial strategies with life stages. By treating each era as a distinct phase with tailored financial plans—similar to how Taylor Swift evolves her career—listeners can achieve sustained financial success and adaptability.
Doug (59:47):
"The big lesson... build your foundation when you're in your teens if you want to have any shot in hell to retire comfortably."
Doug encapsulates the episode’s essence, emphasizing the critical nature of early financial foundations while acknowledging that it’s never too late to start preparing.
Joe Saul-Sehy (02:22):
"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."
Alyssa Mays (08:27):
"Make sure you have your own plan and your own way of implementing things that, of course, works."
Roger Whitney (10:53):
"There is no need to choose one or the other. I think you can have a little bit of both if you're intentional about it."
OG (15:38):
"Set up so that you have automatic escalation, you know, every six months or every year."
Roger Whitney (35:52):
"You need to control your lifestyle creep... start positioning yourself to maximize income."
Roger Whitney (48:11):
"Investment decisions are very different than accumulation decisions."
Alyssa Mays (46:30):
"Check in on your finances... make sure you're staying on track so you don't wake up one day wishing."
Doug (59:47):
"The big lesson... build your foundation when you're in your teens if you want to have any shot in hell to retire comfortably."
The Stacking Benjamins Show effectively intertwines financial wisdom with relatable metaphors inspired by Taylor Swift’s career, providing listeners with actionable strategies tailored to different life stages. By maintaining a conversational and humorous tone, the hosts make financial literacy both enjoyable and practical, ensuring that listeners, regardless of their financial knowledge, can benefit from the insights shared.
For more detailed discussions and resources mentioned in this episode, visit StackingBenjamins.com and follow the hosts and guests on their respective platforms.