Money and Business Lessons from the Career of Taylor Swift (and a BIG Roth IRA rule clarified) SB1670

Summary

Podcast Summary: The Stacking Benjamins Show – “Money and Business Lessons from the Career of Taylor Swift (and a BIG Roth IRA rule clarified) SB1670”

Release Date: April 14, 2025

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Introduction

In this episode of The Stacking Benjamins Show, hosts Joe Saul-Sehy and Doug (also known as OG) delve into the strategic business maneuvers of Taylor Swift, exploring the financial and career lessons that listeners can extract from her rise to prominence. Additionally, the hosts address a crucial listener question regarding Roth IRA rules, providing clarity and actionable advice for their audience.

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Taylor Swift’s Strategic Genius

Timestamp: [06:55] – [07:28]

The discussion kicks off with an analysis of Taylor Swift's early career, highlighting her strategic advantages and unwavering clarity of vision. Joe emphasizes Swift’s unique position, noting, “By the time she’s 13, she’s already seen as this huge talent” ([06:57]). This early recognition, combined with her parents’ modest connections in the music industry, facilitated her signing a developmental deal with RCA Records at a young age.

Clarity and Vision as Career Drivers

Timestamp: [07:26] – [12:08]

Joe and OG explore the concept of having a clear "North Star," referencing psychologist Michael Gervais’s insights that high performers thrive when they have a definitive vision guiding their actions. Joe states, “High performers are more willing to push themselves, learn more, and embrace discomfort because they can shut out the noise and listen to their own well-calibrated internal clock” ([10:30]). This clarity allows individuals to stay focused on their strengths, much like how Taylor Swift concentrated on her songwriting prowess while strategically aligning with key industry players.

Building the Right Support System

Timestamp: [31:53] – [35:10]

A pivotal moment in Swift’s career was her collaboration with Scott Borchetta, the founder of Big Machine Records. Joe highlights, “She surrounds herself with people who aren’t like her but whose goals align directly with hers” ([31:53]). This partnership was instrumental in launching her brand, combining her songwriting genius with Borchetta’s marketing acumen. OG adds, “Having competing specialties and differing opinions can guide and shape decision-making” ([33:06]).

Navigating the Sophomore Slump

Timestamp: [40:02] – [47:59]

The hosts address the common industry phenomenon known as the "sophomore slump," where an artist's second album often fails to meet the high expectations set by their debut. Drawing parallels to Taylor Swift’s sophomore album, Fearless, they discuss how Swift mitigated this risk by implementing incremental innovation. Joe explains, “On every single album, she's giving her fans exactly what they want… but she stretches just a little further” ([50:37]). This approach aligns with James Clear’s concept from Atomic Habits—making small, consistent improvements to achieve significant long-term success.

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Financial Lessons from Taylor Swift’s Career

Consistency and Incremental Improvement

Joe connects Swift’s methodical approach to personal finance, emphasizing the importance of consistent contributions and incremental growth in investment portfolios. OG relates this to the idea of rep-accumulation in portfolios, stating, “The importance of rep, super important… The hard part is recognizing that’s the fun part” ([45:38]).

Process Over Outcome

The discussion reinforces focusing on the process rather than obsessing over immediate outcomes. Doug mentions, “The hard part is trying to make the process the fun part” ([42:12]). This mindset encourages sustained effort and resilience, key components for both career advancement and financial stability.

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Listener Question: Clarifying Roth IRA Rules

Timestamp: [55:10] – [57:54]

Listener Eric reaches out with a question about Roth IRAs: “If I roll over a Roth TSP or Roth 401k into a Roth IRA upon retirement, does the five-year waiting period start then?” The hosts provide a comprehensive answer:

• Understanding the Five-Year Rule: OG explains that the five-year rule begins on January 1st of the tax year in which the first Roth contribution was made, regardless of when the rollover occurs. “The five-year clock has already started” if contributions were initiated earlier ([57:37]).

• Implications for Rollovers: As long as Eric has been contributing to his Roth 401k for at least five years prior to retirement, the rollover to a Roth IRA would not require an additional waiting period for the earnings to be withdrawn tax-free ([57:54]).

• Encouraging Early Contributions: Joe advises listeners who haven’t started a Roth IRA yet to “put a dollar in, man, and get that clock ticking” ([57:37]).

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Key Takeaways

1. Clarity and Focus: Having a clear vision or "North Star" is crucial for sustained success, both in career and personal finances.
2. Strategic Partnerships: Aligning with individuals who complement your strengths can significantly enhance growth opportunities.
3. Incremental Improvement: Small, consistent actions compound over time, leading to substantial achievements.
4. Process Orientation: Emphasizing the importance of the process over immediate outcomes fosters resilience and long-term success.
5. Roth IRA Insights: Understanding the five-year rule is essential for maximizing the benefits of Roth IRAs and planning effective retirement strategies.

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Upcoming Episodes

• Wednesday: Interview with Kevin Evers, author of “The Strategic Genius of Taylor Swift”, where he delves deeper into Swift’s business strategies.
• Thursday: The hosts will release their 201 newsletter, focusing on career and investment strategies.
• Friday: A roundtable discussion with financial planners Alyssa Mazes and Roger Whitney on the "eras" of life and corresponding investment focuses.

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Conclusion

This episode masterfully intertwines the success story of Taylor Swift with practical financial advice, offering listeners valuable lessons on career strategy and personal finance management. By highlighting the importance of clarity, strategic partnerships, and consistent effort, Joe and OG provide a roadmap for achieving sustained success in various facets of life.

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For more insights and detailed show notes, visit StackingBenjamins.com.

Transcript

[Joe Saul-Sehy]

This episode is brought to you by 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 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. State Farm is there. I just found out that there's this company in town that makes yardsticks and they're not making them any longer.

[Doug]

God be better. Look. Oh, gee. Left because of that.

[Joe Saul-Sehy]

It just literally got up and left.

[Doug]

That was it. We found the last straw.

[Joe Saul-Sehy]

That was the one that did it. All the jokes over all the years and that's the one that ended it. Oh, look at he's. He is back. Let's raise our mugs, everybody, and kick off this fantastic week of shows on behalf of the men and women at Navy Federal Credit Union and the men and women making podcast in mom's basement. Big salute like we do every Monday. To our troops keeping us safe. While we played all weekend watching the Masters, having some fun, I was wandering around Michigan State University. Ghost party. Here's to our troops.

[Doug]

Trying to see if they would give you a degree.

[Joe Saul-Sehy]

Finally.

[Doug]

Please.

[Joe Saul-Sehy]

I went here for seven years.

[Doug]

I know it's here somewhere.

[Joe Saul-Sehy]

Here's to our troops.

[Doug]

Thanks, everybody. This is my third double espresso this week.

[Joe Saul-Sehy]

Oh, my God. And fuego. Here it comes.

[Doug]

It's the fastest intro ever. Here we go. Live from Joe's mom's basement, it's the Stacking Benjamin show. I'm Joe's mom's neighbor, Doug. And this week let's focus on things you can control, like your creativity, your business sense, ways to make smarter decisions and juggling all of your financial responsibilities. That's right. It's time for a deep dive case analysis. And today we're. We're diving into the strategic genius of perhaps the Greatest business person of our time, Taylor Swift. But we've also received lots of questions from our stacker family. So we'll answer a question from one stacker who thought, you know, I'd better call Saul. See?

[Joe Saul-Sehy]

Hi.

[Doug]

And OG Today, Eric wants to know about some specific Roth IRA rules. And of course, we have a great answer. Wait, all that plus my trivia. Yes, it's just like heaven, isn't it? And now two guys who are the angels on this podcast proclaiming the glory of better money management. Oh my God. I just threw open my mouth a little bit. It's Joe and. Oh, Juju. Jj.

[Joe Saul-Sehy]

Hey there everybody. Welcome to Good Money Management in a Box podcast. I am Joe Sal Sehei and we have a great week of shows for you. So sit back, relax, you found us. We're gonna have a bunch of fun diving into the career of the Taylor Swift with a man across card table from me. Mr. OG's here. How are you, brother?

[OG]

Great, yeah, thanks for asking.

[Joe Saul-Sehy]

You have a good time with the Masters last week? Thinking about how next year you're gonna be there on the course.

[OG]

I've applied for tickets every year since I was 19 and next year will be my 30th year of applications.

[Doug]

When is this guy going to get the message we're not giving him tickets?

[OG]

You'd think I'd get the hint, but I have faith one of these days. So this year they started a thing, or maybe it's been around for a while, but it's the first year I noticed it where you can order from the catering company who does the master's food. You know, the master's obviously great golf, but there's a lot of things surrounding it, right? Like the egg salad sandwiches are a dollar, you know, or whatever.

[Joe Saul-Sehy]

But yeah, you thought. By the way, the Costco hot dog was iconic like the Masters food prices for such a high end tournament iconic.

[OG]

Or a $50 or something.

[Doug]

You can buy one of everything on the list for $77.

[OG]

That seems like a big list because I've seen like. Yeah, maybe, maybe, maybe the list is. Anyway, it doesn't matter.

[Doug]

There's like 30 things available. I mean it is dirt cheap.

[OG]

So anyways, the company that does the catering, you can order the Masters party kit.

[Joe Saul-Sehy]

How fun is that?

[OG]

So they send you a jug of pimento cheese to put on sandwiches, a jug of egg salad, some potato chips, little cups and stuff. So anyways, that came, we had a little master's party, played a little par three tournament on Wednesday, which was kind of fun. You know, we move, we moved the tee boxes around so that they're different shots.

[Joe Saul-Sehy]

Yeah.

[OG]

It's just kind of a fun week.

[Doug]

Just skip one across the water.

[OG]

You know, I don't actually try to do that any on any one hole, but there inevitably is a hole where I'm like, go, go, go.

[Doug]

I can blade a gap as well as anybody.

[OG]

Yeah. So plus it's just been, last week was just such great weather in Dallas. So I mean, other than that, nothing else was really going on around here. So, you know, we just, we just kind of laid low, just stayed out of the news cycle. Does anything major happening? I'm kind of unaware.

[Joe Saul-Sehy]

I truly don't know. I try not to know. Just keep my, keep my head buried all the time, you know. It is big news. We're going to be diving into the career of Taylor Swift this week. And the reason is Kevin Evers from Harvard Business Review. He's edited so many top case analysis stories for HBR and now he has his first book. There's nothing like this. The strategic genius of Taylor Swift gives us a great excuse to dive into this person's career that we could spend probably four hours going over all of the accolades. But just from her first album and before, youngest person ever to have a development deal with rca, Grammy nomination for best new artist. Amy Winehouse won the year that she was, first year she was nominated, longest charting album of the decade on the Billboard 200. That first album, Taylor Swift, first woman to write or co write every song on a platinum selling country album. And that just obviously begins this, this.

[OG]

Long on and on.

[Joe Saul-Sehy]

Yeah. And the stuff that Kevin is dissected from her career and he's brought in all of these different experts and different fields to talk about. I've grabbed some of those today and we're going to do a deep dive in anticipation of interviewing Kevin on Wednesday. So whether you like or dislike Taylor Swift, to get to that point where people know you enough, where they're like, yeah, hard pass, just the ability to get to that point. OG means she's done something big in her career.

[OG]

We are, we are swifties here.

[Joe Saul-Sehy]

You've got some swifties in the family. All right, we're going to dive into Taylor Swift's career in just a minute. Some key points from early in her career mostly. But before that, we have a couple sponsors that make sure this show is free. You don't have to pay a dime for it. So let's hear from them. And then we're deep diving into the strategic genius of the Taylor Swift. This episode is brought to you by 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 baking experience that lets you keep on baking on. It can save you time and money with new lightning fast direct deposit set up. 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. Every day when we're on the road, people around us endanger themselves and others by using their phones while driving. They think they're hiding it, but we've all seen them and we know exactly who they are. For instance, there's the sneak a peeker who darts their eyes between the road and their text. There's also the got a ticketer looking upset because they just got a ticket for using their phone while driving. And what about the fast grower who can't drive five minutes without updating their social feeds. Or the night lighter who has that mysterious glow illuminating the inside of their car after dark. Any of these sound familiar? If they remind you of yourself or someone you know, rethink your behavior before you find yourself becoming the fender benderer, the veering off the rotor, or worst of all, the driver who killed someone. Put the phone away or pay paid for by nhtsa. Right, OG let's set the stage here, guys. Early on in your career, I think it's about finding out where you fit. You think about out of college. For me, that was pretty difficult. Like, what's the thing I'm gonna end up doing? Taylor had some strategic advantages. She had parents who had connections in the music industry. Not huge connections like, you know, so and so's dad is a record executive. But she does have connections that are gonna help her ease into it and get this RCA deal at age 13. But the reason she got it was combining those connections with her ability to actually play music that by the time she's 13, she's already seen as this huge, huge, huge, huge talent. This idea OG of, of getting clarity is so, so, so hard. But as Kevin Evers points out, psychologist Michael Gervais, who works with elite athletes and CEOs, says that because of their clarity, because they have this vision, this North Star, they know where they want to go. High performers are more willing to push themselves, learn more and embrace discomfort because they can shut out the noise and the opinions of fans and media and listen to their own well calibrated internal clock. Doc. They wake up, oh, geez. They know what they're building, they know where they're going. I think this idea of trying to get clarity as soon as possible, maybe not about the whole adventure, but certainly about this is what my job is in this role. This is why I'm in this role. This is what I want my next step to be. I think that's hugely important to beginning to stack some Benjamins.

[OG]

I think maybe as a larger society, maybe getting a little closer to this. But I think the more that you can focus on the things that you are really super good at and work to be great at those things and not do any of the things or as few of the things that you're not good at as possible. And there's a balancing act here, especially I think about this with our kids. We have maybe good or maybe bad. Some people will tell me, or maybe I'll find out in 40 years. My kids aren't adults.

[Joe Saul-Sehy]

Would they write their expose about dad?

[OG]

I'll take one of our kids, for example. Really great at math, not great at English. Right? Like, doesn't like it. He's, you know, he's fine. He could make it happen, but you know, not going to be the Pulitzer Prize winning author.

[Joe Saul-Sehy]

Right?

[OG]

Just not as jam. And so our communication about that with him is, look, we'll take the B in English, we'll take the middle of the road grade. You don't have to take ap. You know what I mean? Like, you can take normal, just get a B, but you have to get an A plus in math. And so you're going to take the hard. You know, if math is your thing, you're going to take the hard math. You don't get to take easy math because it's easy for you and you like it. You're going to take hard math so that you're challenged, so that you continually get better in the thing that you're really good at. And I think that the more that you can do that, and that's not true for every position. Right? Like there's certain jobs and certain Roles. I mean, even our job and our role, we do things. As much as we try to stay in our own lanes, there's still some stuff that you do that you're not an expert at. And things that I do that I'm not an expert at. It's just part of, you know, running a business. But the more that you can do that and the more that you can work to try to stay in the thing that you're excited about, the thing that gives you energy, and this is a way to test it, I think, is when you get home from work or you get home from doing that thing, do you come home with more energy or less? You know, and if you come home and you're like, every bit is energetic because you just had one of those days where you're like in the zone and like everything's great, that's the day you want to repeat. If you come home and you've had a good day but you're drained, that doesn't mean that you can't do those things. But that's not the thing that's going to provide that never ending energy.

[Doug]

It usually means I went to the bar first before I got home.

[OG]

Could be. And I suspect Taylor Swift has. I don't know anything about her, but I suspect that she has lots of days where she's like, okay, I'm exhausted and I did really good work today. And then she has days like, I'm just making it up. Maybe her tour days are. She worked her tail off, she was in the zone and she comes home with energy because you can kind of see that in the output.

[Joe Saul-Sehy]

We'll hear on Wednesday from Kevin, some stories about some of her early collaborators and how that North Star that she had from the very beginning shows itself just immediately. She's like, yeah, we're not doing that. I mean, to 50 year old men who've been in Nashville for 30 and 40 years, she's like, no, yeah, I need your help over here. I don't need your help over here. Like, it's very clear that even at that young age that she already has a ton of clarity and already has a plan and she has drive. I mean, the amount of the stuff we're going to talk about that goes back to just a couple of weeks ago, the Molly Fletcher week, where you talk about this dynamic drive because it's from within that you're continuing to produce energy. To your point, OG is huge. But I want to segue from career here for a second to your portfolio because this is also Important with your investments. I think this idea of clarity, I feel like when in the past, when I was a planner and I saw messy portfolios, it wasn't necessarily messy because I have all these positions and I just like them all. It's because I don't really have a vision of what my plan is of how I'm going to spend these things. Like, the more you have clarity around, your vision also helps you organize then investments that actually make sense for your portfolio. And you get in a time like now when the market's kind of bumpy and you're. You're not at all concerned.

[OG]

Yeah, I don't know that anybody's not concerned. I mean, this is. I wrote in an email a couple of weeks ago, I think this is number six of these. For me, it's. They're still not pleasant. You know, I'm not concerned. Concerned, but it's. It's not my favorite week.

[Joe Saul-Sehy]

But you have a degree of faith that your money's going to be there when you need it, because you know roughly when you're going to need it.

[OG]

I think the biggest thing when it comes to investing, when all you do is think about the money and you don't think about what it's for, then you don't really have a measuring stick, or your only measuring stick is performance. And so your barometer for success is going to be only what did it do today? Or this month or this quarter or this year or whatever period of time you feel like searching. And what's really interesting about that, of course, is that you can manipulate that pretty good. Like if, Joe, if you're like, hey, man, how did my money do? I can show you through February 19th. And it is, mwah. Choice, you know, year ending February 19th, 2025. Glorious. Two months ending April 7th. Not so bueno. You know, it's like, you can manipulate that, but what you're trying to do with your money is make sure that your expectations of what your money's going to do is in alignment with what your money's actually doing. And as long as that's the case, then in all likelihood, you're not gonna do the big mistake, the big error that's gonna cost you a decade or two decades worth of. Worth of investment returns because of the big mistake. And the big mistake comes in two ways. It's either why the heck are my buddies growing at 25%? My portfolio is only 12. Oh, it's because I don't have Nvidia or Tesla, let me go in. Or why the heck AM I? Down 15% in four and a half trading days. That's ridiculous. I'm gonna get out. You know, those two wild extremes. And I guarantee people that are listening today have thought about the upside one, because, you know, you just go, well, man, I don't know, maybe I should. People are talking about bitcoin. I don't, I don't feel like I have any of that. You know, there's a little bit of that. There's always a little bit of that. Just a smidge. And I guarantee that there's people that have thought about and I'm almost certain people that are listening have done the. I need to make a change today because my money is behaving in a way that I didn't expect it. And when you don't have confidence in what your money is, the range of expectations, if your confidence is lacking, you're more likely to make a change.

[Joe Saul-Sehy]

And I think that confidence og begins with that clarity of vision. I know where I'm headed. I know where I'm headed. I know what I want. And because I know what I want, then it's fine to say, yeah, I don't have any bitcoin. But bitcoin doesn't fit what I want. It doesn't. It doesn't fit in. I want these people to work with me on these songs. But I need you for this. I don't need you for this. And it's amazing too how as I was reading this case study about how much better Taylor writes music In a two year period, she already has signs of genius at 13. By the time she's 15, she's writing these incredibly amazing songs. In fact, one guy said that it was like one out of every five songs or something is great. I'll ask Kevin on Wednesday. But by the time she's 15, one out of every two songs she writes has a shot to become a hit. So she gets these people in her corner and then she learns from that very, very quickly.

[OG]

And I think the other part of that just to add to that is she kept doing the thing that she was really good at. Yeah, it was like, I'm good at this and I'm going to do it. And I'm going to do it, I'm going to do it. The reason that maybe one of the reasons that that ratio is one out of two or one out of three or one, you know, whatever number you said is because she got a lot of at bats. I don't know how many songs or how many albums she Has. But my daughter is a big time Taylor Swift fan and started taking pieces of paper and writing the albums and writing all the songs on each paper and then would tape the papers together. I'll show it to you. It's taller than I am. I had no idea that this woman wrote so many songs and performed three albums. Yeah, it's this huge thing that she kept on like building. I don't know what she was doing, but she was just, you know, writing down all the songs that was on every album on a piece of paper, like. And just, you know, it's like, how many at bats is that? Those are the songs that made the albums. How many songs didn't make the albums?

[Doug]

You know, I think that's the key point.

[OG]

Yeah, you know, it's like just I was doing the thing and I kept doing it and it's like, why was that person so great at that one thing? Why was that baseball player so great? Why was that? You know, there's a lot of God given talent in there, of course. But then they leaned into it and went, you know, I was watching the thing we were talking about the Masters. I was watching this thing at Augusta. Now they track how many range balls each pro hits for practice. The number one person, I don't know how he's going to finish because we're recording this a little bit beforehand. The number one range ball hitter was Bryson Dechambeauty. He hit 390 range balls on Tuesday before the Masters. For me, that would be like one normal round of golf. Like 390 shots.

[Joe Saul-Sehy]

300.

[Doug]

And I know, and we know how our body feels after those 390 shots. Imagine what he has to do.

[OG]

So you go, well, like, why is that pro golfer so good? Because he hit 390 shots on a light practice day. Like he's not going all out the two day. You know what I mean?

[Joe Saul-Sehy]

Well, and to your point, when the critics came, I'm going to fast forward a ways. We're going to go back to the beginning days.

[OG]

Turns out Taylor Swift was successful.

[Joe Saul-Sehy]

After her. Her second album comes out fearless. She makes some changes on that second album. But of course the critics come out like they do for everything that all of us do. And the Guardian, big name British publication, is wondering how the hell a country artist, Taylor Swift, has made her way to Great Britain. And this critic, Alex Petridis, I think is how you pronounce it. Alexi Pedritis, he says that Leanne Rimes and Shania Twain had done it before Swift, but they did it OG Largely by just getting rid of anything country sounding in their music. They just completely just stripped out the country. It's almost like that Gaffigan bit about how do we get kids to eat granola? We just get rid of the granola, right? Put a bunch of chocolate in it. That's what we do.

[OG]

Exactly.

[Joe Saul-Sehy]

But Swift has left some of the, you know, those country sounds in songs like Love Story. I think most of us have heard the pop song Love Story, like Romeo and Juliet.

[OG]

Give us a little bit of it, Joe.

[Joe Saul-Sehy]

Doug, can you sing it? It's a love story, not a note. But here's what he said. And I think OG he lands on something really important, which is he asked this question, what makes Swift so damn popular? And he comes to this conclusion that she does something, quote, bland and uninventive, but does it incredib incredibly well?

[OG]

Very British way of saying, yeah, nice things?

[Joe Saul-Sehy]

He is not a fan. But the point is, is that I think a lot of us think we got to reinvent the wheel, right? We got to come up with. There is some gene that somebody has where they had this brilliant idea that I didn't have, and because of that, I'm never going to get there. But this British guy is talking about, I think, what is truly the truth about what Alex R. Mosey said to us earlier in the year that Molly Fletcher said, which is that if you focus on that thing like you're talking about and you swing and you swing and you swing and you swing, or, you know, you're one of those great chefs and you cook and you cook and you cook and you cook, guess what's going to happen? You're going to make a better meal than somebody that took half of those reps. Yep, 100%. There is also, from the very beginning, I think, a lot of importance in Swift's career about knowing what the challenges are going to be. So, number one, the music industry in Nashville, very closed circuit industry, very small industry. Everybody knows each other. They all believe there is no market for teenage girls listening to country music. There is no market. Forget about that. The second thing is that young women making country music, they'd seen Leanne Rhymes do it, they'd seen a couple other people do it, but not many at that time. 80% of all the hit songs in country radio when Swift is trying to break in, are men. So she's trying to speak to a market that Nashville goes, no, isn't there, doesn't exist. She's trying to create these confessional based songs. For 13 year olds that when you got old dudes in a Ford pickup truck, are they going to listen to this crap? Really? Is this going to be it? She knows that's what she's up against from the very beginning. And I think that, that, you know, we talked last week about risk in your portfolio. I think knowing what the challenges are going to be as you're walking this path I think is really important. How many times have you seen somebody at your job that's pretty good at your job but gives up very quickly? I remember when I was a financial planner, this one guy, James, James was so upset, he was a great financial planner. James was so upset that he was going to have to prospect for new clients that it just sent him out of the business. And I'm like, James, this is like the job. This. You have to find people who become your audience, right? No matter what your, what your thing is, if you're in sales, which essentially every job to some degree is say, I got to convince my boss that I'm great at the assembly line. James let this stupid stuff because he doesn't recognize what the challenge is from the beginning get in his way. So I think laying out what the challenges are and going, you know what, these are going to be the issues that are going to come up and I'm not going to let those stop me. Huge thing when it comes to our success. And I think that's also big at a time like now OG for your portfolio.

[OG]

Well, again, I think if your expectations are aligned with what's really going on, then it's not a surprise. If you're finding out for the first time that equity prices can go down quite violently in a very short period of time, you've done yourself a disservice to not know that already. Because this is a surprise to you. It's a surprise. I think it's a surprise to everyone, but it's a surprise that's forcing you to consider changes. Whereas I think people who have confidence in their plan recognize that this is part of the game and it's just, it's not a fun part. It's like sprints on the football field before the season. It's just part of the game, but it's not a fun part.

[Joe Saul-Sehy]

I think though, do you think differently about the challenges? When you know what the challenge is and you've laid it out, then you know, okay, this is that time that differentiates the people that win from the people who lose.

[OG]

I remember I was thinking about when I was in Boot Camp. I remember the never ending pting and never like, just the never ending hikes where you throw all your crap on and you start walking this godforsaken sandy area of the country. You just never had any sense of beginning, middle or end. You were always just in the middle and it always sucked. And I remember one time thinking, all right, I just need to break this down into periods of time. Eventually, they're going to feed us lunch. This seems pretty regimented in terms of schedule. Like, we've always gone to bed at 9:30. We've always got up at 5:30. We always have breakfast, lunch, and dinner. It varies in its time by a slight amount, but there seems to there. They seem to have some contractual obligations to feed us, you know, so. So I'm pretty confident that we're going to eat. And so it was like, okay, I got up, it was chaos. Now I get breakfast. And now I know it's going to be chaos, but I know lunch is coming and there's no time. It's like Vegas, you know, it's just. There's no clocks or anything. You just have to like, use. Use like sundials to try to figure out where it is. But it's like, okay, oh, that's the 737 to Albuquerque. I've seen that plane a thousand times. For those of you who have been to San Diego, if you look out the one side of your airplane, depending which way you land, that is Marine corps recruit depot, one of the two of them. And so as a boot camp kid, freedom was just the tarmac. It was like, literally, if I could get that fence, run six miles across the tarmac, I could jump on the next plane. But you know, you see all these planes take off time after time, and you like, you'd start to get a rhythm of them, right? You're like, okay, there's a Southwest, then there's United, and there's the American jet. You know, you just like, do we.

[Joe Saul-Sehy]

Even do that running today at nowhere near boot camp. So I don't want to make a boot camp reference. But 605, the American Airlines flight, goes overhead while we're on our run. Yeah, like every day, like clockwork, the 605 different spot.

[OG]

You're like, I'm ahead of pace, I'm behind pace.

[Joe Saul-Sehy]

That's right.

[OG]

So we just kind of like sort of had to break it down. And I think when it comes to, you know, volatility in the market or, you know, that sort of thing, you have to recognize where the beginning, middle and end might be otherwise. It always seems like you're in the middle of this chaos and it's like, you know, being down, whatever it is by the time you listen to this. But as we're recording it, maybe, you know, -20 at this point, we are exponentially closer infinitely. It's a time based one. Let me get that right. We are infinitely closer to the end of this than the beginning. We've already gone 20% of the way in. Like there's only 80% to go. It's like it can only go to zero. And I was thinking about this too. It can never go to zero. Your percent return will never be minus 100 because it's statistically impossible to be minus 100. You could be minus infinity if you go to zero, but it can be 99%.

[Joe Saul-Sehy]

That's the good news, right? Stacking Benjamins, we can only go to minus infinity, not minus 100.

[OG]

That's because it will always be worth a penny. Anyways, my point is, is that if you can appreciate where this is in that cycle, you can see the daylight, you can see the horizon or whatever it is, and it provides you just that little bit of hope. As boot camp transpired, it was like, okay, there's three phases and there's three meals and there's, you know, it's like, okay, we're, we're in phase two. So I know that there's, you know, I got a little bit more of this and then we do this and then it's close to coming home and you know, it's all this stuff.

[Joe Saul-Sehy]

But what is that? That is, that is challenge plus reps. Because you've been out there enough. I know that flight going over. I know this flight going over. I know. So to the point that we made earlier rep super important. Knowing the challenge is super important and having that vision that I'm going to make it to freaking lunch.

[OG]

Yes, I just have to make it to lunch. I don't even have to think about dinner because, you know, I know I get a 32nd break at lunch where at least I'll get a glass of water and a two pieces of bread.

[Joe Saul-Sehy]

I want to bring up one more thing just before the break, donut. Which is that I think then the next thing we couple together is who we surround ourselves by. I talked about those early contributors. She gets paired up with these industry insiders in Nashville to help her write her songs and they're already talking about genius that she has. She also very quickly gets out of her RCA deal, just says you know what? I don't think this is going to work for me because it doesn't fit my vision. By the way, RCA paying her a ton of money on this developmental deal and she gives them the finger, which is a whole different story that people can read about. Pretty, pretty ballsy. And shows that she knows where she's going. But she gets this lifeline early in her career by working with another guy named Scott Borchetta. Now Borchetta later on, if you know anything about Taylor Swift, becomes a villain in her story, right? He's got her master, she wants her masters. But early on, these two people are geniuses in different ways. He's a genius at marketing, she's a genius at writing her song and having that vision. What's cool is, is that Swift decides at this big moment that she's going to team up with this guy who OG is nothing like her. And what's amazing is to me is that she's got these people whose goals line up directly with hers. When she's with these, these older men, they want to write a hit song, they want their name on a hit song. She wants to write a hit song. Borchetta needs a big win in his career. He's just launched this brand new record company, Big Machine, and he needs it to go really well. So he needs to market really well. She needs it to go really well too. I think we make a mistake when we align ourselves only with people. And for me, this is the genius of strategic coach. Because you and I, when we do strategic coach, we're in this room of people who are not like us. They're in different industries, they're focused on different things. But when we surround ourselves with just, yes, people exactly like us in our exact same little sphere, all of us, you know, writing music for 13 year old girls, and that's all I'm talking to, is people that write music for 13 year old girls. It doesn't create this, this genius. I think the genius is she surround herself with people who aren't like us or who aren't like her, but people whose goals align with her, which I think is a big differentiator.

[OG]

There's a really good reason to have competing specialties, have competing expertise and even differing opinions about how things should go. It's taken me a long time to be okay with other people saying I think you're doing this wrong in different things. That doesn't mean that their way is right and my way is wrong. It just means that from their perspective and that helps guide and shape, like, decision making. I think when it comes to people who have different skill sets than you, a lot of times you think, well, that's not going to work because we're going to be butting heads. And I think you can do that in a lot of settings in a good way, as long as it comes from a position of respect. And you said vision. I'd say love. Maybe even just making sure that, like, I know when you tell me something that I did wrong in the show, you're not being an ass about it. You know what I mean? Like, you're like, no, we both want this thing to do well. I just think you can't pick on Doug's mom as much. And I'm like, all right. I think it's a funny bit, but, you know, I'll let off the gas a smidge. It's cool. I'll tell her to stop calling, you.

[Doug]

Know, I knew it. I knew he couldn't make it all the way through that.

[Joe Saul-Sehy]

Just finds a way to work it back in, Doug.

[OG]

No, I just. I mean, what your mom said back in.

[Joe Saul-Sehy]

All right, I think on that note, it's time to. Time to head to the break, but I think a lot of important lessons there about vision, knowing the challenges surrounding yourself with the right people. In the second half of this discussion, we're going to dive into her second album and the sophomore slump. We're going to talk about the sophomore slump because I think people also have this in their careers. There's a ton we can learn. Also about her portfolio. There's. We're going to do that. And we're going to take a call from Stacker Eric, who has questions about Roth IRAs. Guys. So that's coming up. But first, Doug, you've got today's trivia question.

[Doug]

It's just fact packed, Joe. Hey there, Stackers. I'm Joe's mom's neighbor, Doug, and I mean, what a. What a big time, horrible day this is. First. Tomorrow's tax day. I haven't even started.

[Joe Saul-Sehy]

Oh, man.

[Doug]

You need a second? I'm looking up trivia for today. And, you know, Lincoln was shot on this day in history. That was a bad day for the nation, but arguably, it's even worse for him. Oh, no, too soon. Well, too soon. Okay.

[Joe Saul-Sehy]

All right.

[Doug]

It's also the day in history when the Titanic sank. Bad day for us, but probably a worst day for the past.

[Joe Saul-Sehy]

No, no.

[Doug]

Okay.

[Joe Saul-Sehy]

I'm not gonna.

[OG]

I'm not gonna say it.

[Doug]

I won't say that one might have been slightly more recent in more recent history though. Still a rotten day. It's the day back in 2021 that Bernie Madoff died. I think a worst day was the day investors found out how much they'd been fleeced, which is today's trivia question. Bernie stole $18 billion from investors. That was billion with a B. How many eras tours would Taylor Swift have had to complete to equal the same amount of revenue Bernie pulled in? See, I tie it all together. I know what I'm doing.

[Joe Saul-Sehy]

That's a good one.

[Doug]

I'll be back right after I go complain about all of my exes by writing poems set to music. What word rhymes with oh Oh, I got it itch.

[Joe Saul-Sehy]

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[OG]

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[Doug]

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[Joe Saul-Sehy]

Take one or two courses at a time and complete as many as you.

[OG]

Can in a 12 week billing session with Flexpath. You can even finish the bachelor's degree.

[Doug]

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[OG]

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[Joe Saul-Sehy]

Think with Capella University.

[Doug]

Learn more at capella.edu.

[OG]

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[Joe Saul-Sehy]

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[Doug]

Hey there stackers. I'm singer, songwriter and guy who's all about the rhymes. Joe's mom's neighbor Doug. That didn't rhyme. Back in 2021, on today's date in history, Bernie Madoff passed. The list of who's who who were fleeced by Madoff reads like the credits of your favorite shows, but you can look that up on your own and I wanted to know, if you took the $18 billion Madoff stole and divided it by the revenue from Taylor Swift's ERAS Tour, the biggest tour of all time, how many tours would it have taken? The answer. Taylor Swift's ERAS tour, by all reports, has grossed the star a whopping $2 billion. Meaning it would have taken nine eras tours.

[Joe Saul-Sehy]

Really?

[Doug]

Yeah. Nine eras tours to equal the amount of damage Madoff caused. And now back to two guys helping you recover in your portfolio and your career. It's Joe and OG Wait, why are we assuming they need to recover in their career?

[Joe Saul-Sehy]

I don't know. Who knows?

[Doug]

I wasn't looking. I didn't realize he was gone. I was, you know, I couldn't find a place to sneak this in. But when you guys were talking about it's not just your talent, it's who you surround yourself, it reminded me of, and it always reminds me of my old college friend Christopher. Remember him?

[Joe Saul-Sehy]

Yeah, yeah, good guy.

[Doug]

I mean, yeah, great guy. But this guy was starting quarterback on his football, high school football team at least three years, if not four years. I think he might have been taken over the starter job as a freshman. He was starting catcher on the baseball team all four years. Tried out as a walk on for Purdue's baseball team. Was the last person cut. You're a pretty good ballplayer. If you can try to walk onto a Big Ten team.

[Joe Saul-Sehy]

And almost make it.

[Doug]

And almost make it. You're a good ball player. He was a concert level violinist. He was a concert level classical guitarist. He became an artist and also a fashion designer. Had offers from a fashion house whose name I'm forgetting right now, but on Savile Row in London and had a show for fashion in New York City during Fashion Week. And none of that materialized. Why? Because I think he was hanging out with me.

[Joe Saul-Sehy]

I thought it was just focused on too many things, like too many maybe.

[Doug]

But it was just show. This guy was talented at whatever he tried to do.

[Joe Saul-Sehy]

He exude that. The first time I met him, first time I met him, I'm like, this guy's good at stuff.

[Doug]

Yeah. And, oh, by the way, ridiculously good looking.

[Joe Saul-Sehy]

Yeah.

[Doug]

I mean, I saw that in your eyes the first time.

[Joe Saul-Sehy]

Like us too.

[Doug]

Yeah, very much.

[Joe Saul-Sehy]

It is so interesting, this idea of being good at the one thing, like picking the one thing and having the clarity around the one, one, one thing. Her first album does incredibly well. We already talked about that at the top. So now it's time to do the second album. Have you guys ever heard the Phrase, the sophomore slump.

[Doug]

Oh, yeah.

[Joe Saul-Sehy]

Do you know where that actually comes from? Because I had no idea where I thought that was a musical term. Right. Because I always heard it associated with musical. It isn't. It's actually from all the studies that have shown that sophomores in college have this crisis of confidence. They lose their engagement in the. In whatever they're doing. They change their majors, they often drop out. Like, sophomore year is a time when you start questioning everything. And what's amazing about that is because you now have some freedom. You've had some success, and you've had some freedom. What's funny is, oh, gee, you and I worked, you know, back in the early 90s in this sales organization largely at the beginning, that we saw this all the time in people's careers because your first year was very regimented. The company told you what you needed to do to succeed. And frankly, if you did what they said, your chance of success was fairly high. But at the end of the first year, they just let us go. At least when I was going through training. And the number of people that washed out nearly immediately because all those great things that you were supposed to be doing, you now had freedom from. So you did none of them. You did none of the things anymore that made you successful.

[OG]

I mean, that's true for everything you have successful working out and you go, boy, I look really good. I should go have a donut to celebrate. It's unfortunate because we want to be focused on the results and have results be the reason for your success, if that makes sense. And in fact, it's the process that makes you successful. And the process is not the fun part. So the hard part is trying to figure out how to make the process the fun part.

[Doug]

Absolutely. OG we all love that. That electric feeling you get from inspiration and motivation. You hear a great speech or you see a great quote, or if you're in creative endeavors, that. That electricity you get when you're writing something or singing something, but that's not sustainable. That kind of adrenaline rush is not sustainable. It's the process, which can be damn boring at times. That is the only thing that's going to make it repeatable over and over and over again.

[Joe Saul-Sehy]

It 100. Yeah. If you go back to Molly Fletcher, Doug, I love that callback because, you know, she says that you can't do that. But what is interesting, though, Everest points out Taylor Swift does make her frustration work for her art, because there's lots of ways to let that go. Even though 100 not sustainable. She went on the Ellen DeGeneres show at 1 point and she makes this reference which is a huge rip on her ex boyfriend at the time, Joe Jonas. For people not familiar with Taylor Swift, Taylor Swift likes to rip on old boyfriends. But what's interesting is she stops doing it very, very quickly on these shows. She does it just a couple times in social media or in interviews and instead she does it in her songs. And so Evers points out that she takes this frustration that she has and she uses it as fuel to dive into, dive into the next songs. In fact, it's funny, I have this book of quotes from great artists. I've got one here from Sonia Boyce. Her whole quote is let frustration fuel inspiration. If you're frustrated, use that as short term sugar, this energy to move the ball forward. Because what do we often do? We, we take it out in ways that aren't like, I mean, Taylor Swift uses that sugar in a way to help her career. We might get on social media, we might grab something to drink, we might do self destructive stuff instead. Swift lets it power her, which I think is, is also a great lesson. But speaking of powering, everybody's worried about the sophomore slump when it comes to Taylor Swift. She's had this huge album. Is the second one going to be as big? Some artists don't get it at all. Like Madonna never had a sophomore swamp. Katy Perry. Nirvana had a better, bigger second album than their first album. Others rebound. Bruce Springsteen had a second album that wasn't highly regarded. YouTube. Bon Jovi had these albums that later on people kind of nod at and go, I think we missed what was really going on here. But sales at the time weren't that big. And some people, by the way, sophomore slump ends up being a slump for the rest of their career. Jewel has been around a long time, but never equaled that first hit song she had. Hoodie and the Blowfish had a phenomenal first album, toured for a long time, but never ever hit that note that they hit when they first came out. There's a lot of reasons that they're worried about this sophomore slump. So the question is, is how do you, when expectations are so high, rock even more. But what's, what's funny about this whole thing og is that by starting fast you create this thing that's quote a problem. But what a great problem to have. By hitting all the notes early on, right? By having clarity early on, by hitting your career hard early on, by getting, you know, just widening this out by getting money early on we talk about later on, you get to maybe $100,000, you need to know how to diversify. Maybe you get to a hundred thousand dollars and now you got this problem. I don't know how to diversify. I think the sophomore slump is important. But regardless of that, getting out quickly, getting, moving quickly, getting those reps in, like you say, quickly, much more important than worrying about, like, what's going to happen next.

[OG]

I think it comes back to enjoying the process more than the outcome. And when it comes to money, I don't believe that people believe in compounding in advance. I think when you do your financial plan or you pull out a calculator and say, okay, I've got $100,000, and I'm going to put in 20,000 a year in my 401, and it's going to grow at 10% a year, 8%, whatever number you want to use, and I've got 30 years to do it. How much money do I have? And it says you have $5 million. Whatever it says, you go, yeah, that's wrong. It's very hard to appreciate the potential outcomes. And when you're doing things around contributing money for savings and investing and that sort of thing, it's all about those little tiny contributions that add up over long periods of time. You just, you know, and this is a great example, this period of time we're in right now, you're putting money in, and the next day you look, your account balance is lower, you know, and then you put money in, and the next day you look in, your account balance is lower, and it's like, what the heck is going on? I thought, you know, I'm used to, like, every time logging in, seeing a bigger and bigger number. You know, that's just what it's been for the last couple years. The importance of all of this isn't the fact that you hit 100k or 500 or a million or whatever your number. It's the fact that you keep doing the thing that you're doing over and over and over and over and over again. And this also kind of feeds into investing decisions as you get older and later in life. I talk about this all the time. I have no idea why people would get to 65 and then turn conservative. And it's not a. It's not, it's not a discussion on politics, but I mean, from an investing standpoint, it's like you have the recipe card. You've made it. You know, you didn't get to 65 with a bunch of money because you put it in your savings account, you got it because you bought and owned the biggest companies in the world. And then all of a sudden you get 65. Yeah, I don't want to do that anymore. That worked too good. It's like, I finally have three million bucks. God forbid I get to six. You know, it's like, do the thing that's been successful for you over and over and over and over and over again. And the hard part is recognizing that that's the fun part. We think the fun part is like opening the statement and going, oh, I got a million bucks. Yeah, go me. Or my net worth went out.

[Joe Saul-Sehy]

Pressure around the, quote, sophomore slump, when you just love the thing.

[OG]

Yeah.

[Joe Saul-Sehy]

That pops a lot of the balloon. Like, let the outcome take care of it. So if you're outcome based, the sophomore slump is going to hit hard.

[OG]

Well, the hard part with money is that there is no outcome, there is no win. You can say, well, I'm financially independent, but there's always more money to have. There's always more goals to have. You know what I mean? Like the goal that you had when you were 25 and you're 45, you're like, well, I smashed that. But now I have these other things. Like there's a roll up to my.

[Joe Saul-Sehy]

Problems in a limo.

[OG]

Yeah. I mean, it's just the risk is that you recognize that there is no end game because you can always have the next thing. And I'm not even saying about like consumption. I'm just saying you can have bigger ideas. You can say, well, I donate a thousand bucks to church every year. I would love to be able to do 10,000. Now that's a new thing that triggers new stuff. And you could do 10,000. I'd like to do a hundred thousand. There is no limit to your fantasies about money. And so that can be very discouraging because you get to the thing that you thought you needed to get to and then you recognize there's no party at the end. You know, it's like 100k or a million. It's like, you know, whatever. Charlie Munger said, the first 100k is the hardest. Right. As soon as you get that, you're good.

[Joe Saul-Sehy]

You think there's going to be unicorns and rainbows and yeah, nobody.

[OG]

You know, Ed McMahon didn't show up with a. Is he dead? I think he's dead. You know, he. People don't know who that is. Doesn't show up with a big check in balloons. Right.

[Joe Saul-Sehy]

Man shows up, now we're in big trouble. Epic. Man's at the door. Oh, crap.

[OG]

They've cloned wolves from 10,000 years ago. Why don't they clone something good like Eggman and man, you know, and it's like you get to a million bucks, you're like, oh my gosh, I hit my financial independence goal. I have a million dollars. And like, okay, so what? Nobody cares. Like, there is no party, there's no balloons, there's no high fives. There's just the next thing. The goal isn't the goal. This is what I think we have to recognize when it comes to money. It's the process of achieving the things along the way.

[Doug]

Well, this is also why. And Joe, you've talked about this. You and I have talked about this in the past off air, and you've talked about it on air quite a bit. It's why gamification has gotten so big. Because process designers and I used to do this when I helped design processes for my clients. Know that you've got to create incremental, smaller along the path goals to get people excited about things, to keep them going towards the big thing at the end that you really want. Otherwise we just can't, we're, we're so weak as humans. We just can't stay interested in that thing that seems so far away. So create smaller, fun ways to keep you focused. And it happens in board games and in video games and it can happen in your investing.

[Joe Saul-Sehy]

I'm so glad you brought that up because that is my last point here, is that she's done this so many times, Doug, that Taylor Swift uses a process that Kevin Evers identifies from all the case studies he's done as incremental innovation. Where on every single album she's giving her fans exactly what they want, which is more the same. Right? But she stretches just a little further. So on this second album, Fearless, she starts going into pop music just a little bit. So she's going to change it, but not a ton. And I think this should be comforting for people because this goes to when we had James clear on talking about atomic habits. If you just have this incremental little improvement every day, like that can make these huge, huge things. Now we're going to talk about.

[Doug]

Imagine if you're the ex boyfriend and you realize I was just part of the process. She didn't really want to date me.

[OG]

She just needed, she just needed a new muse.

[Joe Saul-Sehy]

Swift is like, I had to go out with you. What was I going to do? You're an.

[Doug]

My content says I Need another album.

[Joe Saul-Sehy]

I needed a hit song. And everybody knows you're A.

[OG]

So they're about to know you're A.

[Joe Saul-Sehy]

They didn't already way more than they did before. But, you know, we're going to talk about the. Using his process to differentiate yourself and to constantly be changing next week, because this week we, we are talking strategic. Next week we've got Lorraine Leon, who for a long time was with LinkedIn and it does a great job tactically of helping people with their career. So that's going to be kind of the other shoe. But on this album, she doesn't go completely pop, which, as we all know, is where she's headed, literally. This morning I was talking to Cheryl about what this discussion was going to be and she goes, really? Taylor Swift started off in country. She. She had no idea. Wow. She had no idea.

[OG]

Even I knew that.

[Joe Saul-Sehy]

Right? These are these incremental changes, though, depending on how big a fan you are. You just know her the way that she is now. But knowing where her income stream is coming from, she markets this as a country album first, even though she's know she's going tour pop. Why? Because now that she's made it into the closed loop, the country music is. And now that these old men and pickup trucks have accepted Taylor Swift into the family, they know that this is, this is an income stream that is going to continue pop, as you guys know, much, much more fickle, right? You're. You're a star one day and you're gone the next because that's, that's pop music. In fact, they know this enough that that song we were talking about earlier, Love Story, they actually make two versions of it. They make a version that has more banjo, has more of the country flourishes, and then they strip it out for a second version that they're going to market to pop stations. So country version and pop version, giving people what they want, what they already know, and just this incremental James Clear improvement for people haven't listened to Atomic Habits. We'll link to our interview with James Clear. Because the whole idea of getting much better at where you're going is. Doug, exactly what you're talking about. Gamify it, add it to an existing habit you already have. If I already brush my teeth every day, X number of times when I do that, I'm now going to attach another habit to it. Just incrementally. That's going to make me a little bit better. So much to get here. We've got Kevin Evers himself coming on On Wednesday. Can't wait for that interview. We're going to dive deeply with the guy that literally wrote the book about this on Wednesday. We're also going to on Thursday, Thursday have our 201 newsletter all about your career, your investments. And on Friday we're going to do this cool roundtable with OG and financial planners Alyssa Mazes and Roger Whitney on the eras. Get it? The eras. Eras of your life. What do you focus on with your investments in the early eras? In the middle piece, what should you really be focused on investment wise? And also when you're nearing retirement and in retirement, what are the important things to get right with your money? We got three CFPs that are going to walk us through that on our Taylor Swift theme week. Time for us to make sure that we help a stacker in need because somebody just said I got to call Saul. See? Hi. And OG if you need us to help you, head to stacking benjamins.com voicemail and you can be as cool as Eric, who's called us. Eric, what's on your mind? My friend Joe and OG I have.

[Doug]

A Roth tsp and a Roth 401k. When I retire, if I roll that.

[Joe Saul-Sehy]

Over into a Roth IRA, does the.

[Doug]

5 year waiting period start then? Assuming it's after age 59 or do.

[Joe Saul-Sehy]

I need to do a Roth backdoor.

[Doug]

Conversion now to establish account? I'm currently 52 to start the five year waiting period. So the day that I do retire and I roll over, I don't start the five year waiting period then. Thanks a lot.

[Joe Saul-Sehy]

Love the show. Oh, great question, Eric. And this is just a little tripwire, I think that trips a lot of people up when it comes to the Roth this five year rule. Oh gee, how does that actually work?

[OG]

So let's talk about the five year rule first and then we'll talk about when it starts. The five year rule for Roth IRAs means that you have to have five years from the beginning of the tax year. So by the way, it's not when you put the money in, it's the tax year when you put the money in. So that's basically January 1st of the year you put it in. So even if you put in money for the first time in April of 2025, but it's for the 2024 tax year. You know, you just wait till the last second to put money in. That counts as of 1-1-24. So the beginning of the tax year that your first Roth contribution, you have to wait five years before you can take A withdrawal of the earnings tax free. So even if you're over 59 and a half, you still have to have that kind of five year time horizon before you can take those earnings out. Which is what's super attractive about the Roth. The question, of course is when does that five year start? So it starts January 1st. For most people, that's their tax year. It's January 1st of the tax year that you put the money in. But for Roth 401S or your Roth TSP, which is also a 401K, that's also the beginning of the first time that you did that. So as long as you've got the Roth 401K and you've been contributing for five years, or you started it five years ago, or you put your first contribution in five years ago, when you roll that over when you retire to your Roth ira, your five year clock has already started, basically to say it a different way. So if you're 55 and you started putting money in your Roth 401 when you were 53, and you retire when you're 60 and roll it all over, you've got seven years, you're good. Does that make sense?

[Joe Saul-Sehy]

You've already got it because of the other Roth account.

[OG]

Yeah. The clock starts regardless of where you have the Roth. It doesn't matter if it's Roth 401k, Roth IRA, it doesn't much matter.

[Joe Saul-Sehy]

I think the important thing there then is if you don't have a Roth yet, put a dollar in, man, and get that clock ticking.

[OG]

Yeah, and it's the same thing for Roth conversions too. Right? So it's like, you know, if you don't have a Roth account open and you do a conversion for the first time, you know, now you've got this kind of five year deal, so basically you just want to have that going as soon as possible.

[Doug]

You talked about conversions and it made me think. I know we've got a lot of listeners with 403bs. Any difference there?

[OG]

No, at all.

[Doug]

Same, same.

[OG]

Yeah, same, same. I mean, for all retirement plans are the same, you know, 401k, 403b, 457. Although I haven't really heard of Roth 457, that doesn't mean they don't exist. But any Roth product, it's all treated the same.

[Joe Saul-Sehy]

Okay, Eric, thanks so much for the question. I know that, man, if people don't have that question, that's just a great one that we need to remember that five year, five year clock and how that works. I Think trips up so many people stacking. Benjamins.com. voicemail Again, if you'd like us to answer your question, let's meander before we say goodbye. Off to the back porch, put our feet up after a nice episode. Doug, what's going on in the community, man?

[Doug]

Hold on, Let me pour myself a drink first. Oh, look, it's already here.

[Joe Saul-Sehy]

Imagine.

[Doug]

I don't know if you remember, last week we did a special episode.

[Joe Saul-Sehy]

I can't remember what is about. What actually did we cover on last.

[Doug]

Tuesday, we did a special episode because it had been a couple of days of very tumultuous market ups and downs. Lots of crazy stuff going on. Yeah. You know, just wanted to just resurrect that memory for you. I know you tried to bury it, but. And we got a lot of great feedback from that special episode we did. Thanks for the kind words, everybody. We were happy to see people sharing that episode with worried friends. I know John did that. And. And people taking advantage of that spot in history to rebalance their portfolio and perform their backdoor ira. Excuse me, Roth IRA conversion. So. And we got a great note from JD Dozier on Spotify. That's a great new place that people can leave feedback for us. Appreciate that.

[Joe Saul-Sehy]

We've been just really chatting it up on Spotify. It's been really fun.

[Doug]

I'm too old for Spotify, so I don't. I've never been there. I don't see it. I'm still Apple Music guy.

[OG]

I'm the.

[Doug]

I'm one of 11 people still on Apple Music, but I hear that there's some great stuff happening there. Anyways, JD Doer said, great episode. Very timely with OG's colonoscopy and Doug's story. Couldn't help but to laugh out loud. Pretty sure he was laughing at your colonoscopy. I was fresh out of recovery from my own. Hard to believe we can learn anything from this show. People still say that. It's amazing to me, that's how you know you're a longtime listener. Because we haven't said that in, like 10 years. We don't want you to learn anything.

[OG]

So I'm going to. I'm going to circle back to that. Thanks for bringing that up, Doug, because you and I talked a little bit about this, you know, after the fact, and we're now all senior citizens, apparently, in the colonoscopy world, and.

[Joe Saul-Sehy]

No better way to end an episode, but with a colonoscopy discussion.

[OG]

Joe is. Joe is so senior. He's done with him, apparently you get to end at some point.

[Joe Saul-Sehy]

But anyways, I just got to show him the card.

[OG]

No, it's like a punch card, you know, you're like, I get this one free. So this was my first one. And this is just a public service announcement. This is just my, my take on it. No, I mean, it really is. Joe. I know you think I'm going to go do something funny, service announcements, but I'm not. This isn't.

[Joe Saul-Sehy]

I thought Doug already made the public service. Not. So I'm saying don't eat a pizza at 7pm yes.

[OG]

It's not about that. I'm trying to do the right thing.

[Joe Saul-Sehy]

Yes. Do it. Do it.

[OG]

For me, it was a non event. So I've had this scheduled and rescheduled and scheduled reschedule. I, you know, conveniently had stuff come up. Finally I was like, all right, I just got to get this done. Very concerned about the day before. Took the day off of work. Didn't go to my son's baseball game. Very concerned that it was going to be this whole event. It was a nothing burger. I mean, it was. There was some time spent in various places, but it was the war stories that you hear. And I get that maybe different people have different perspectives on this. Yeah, it was a non event. Like I was like, this is so nothing. I honestly could have worked all day until probably about 3 o'clock in the afternoon. And I probably could have gone to my son's baseball game, which was.

[Joe Saul-Sehy]

What time did it happen at? In the afternoon, Late afternoon.

[OG]

The process that I had was at 12 o'clock. I took four over the counter pills.

[Joe Saul-Sehy]

Oh, did the stuff. I see what you mean. Yeah.

[OG]

At one o'clock I took a Zofran and then two o'clock, started drinking the over the counter stuff with Gatorade. And yeah, it was like from three to six. It was kind of a nothing. It was like, okay, yeah, this is a minor inconvenience. But there was no, there was, it was nothing. The actual event. The actual event. Go to that, Go to the hospital at six in the morning, that kind of sucked. But I went to bed at 9. I got up at 5:30. I slept all night. I was fine.

[Joe Saul-Sehy]

I thought the night before for me, the cleansing piece, very bad. But the event to your point that day, like by noon I was great.

[OG]

Like I was, I was, I mean I was home. So I left the house at 5:45. We were at the doctors, got the IV. About an hour sitting there waiting for the doctor to show up. In the morning. And he showed up, goes, hi, I'm Dr. Sonu. This is what we're doing. They hit me with the propofol and I was out in an instant. People were like, trying to count backwards. See, I'm like, I don't care. I'm going to sleep, man. I like sleeping. So I was like, I have no desire to be awake for it. I'm not going to try to fight it. And like, I was out. And one second later, it's like a time warp. You wake up. There was no side effects, no pain. There's no. There's nothing. There's. There's nothing at all. The biggest pain was, honestly, the bandage that they wrapped after the IV was a little tight, and my arm was hurting, and I couldn't figure out why until I took the bandage off. I was like, oh, the bandage was too tight. Stopped on the way home. Got an omelette and two orders of French toast. I didn't eat there because I went home a little nervous about the first post. You know, experience, you know, movement, visit, movement. That was nothing. Like, there was nothing to it. So if you're thinking about this, and. And I say this because I, you know, it's. It is one of these things that for men and for women, but mostly men, we have this macho thing like, oh, you know, whatever. And it's one of the most curable, preventable diseases that we have. You know, you just. If you know it in advance and you have an obligation. One of my friends told me this. He's like, you have an obligation to people around you. This is a preventable thing. I wasn't nervous about it, but I was like, this is going to be a thing, a whole thing. You know, you have to. What if they do, you know, it was nothing. Just go do it. It's totally fine.

[Doug]

I find it very curious that you said that it. Or at least a turn of phrase you used when you said it was a nothing burger, because. Have we talked about the pizza?

[OG]

Yeah. Oh, yeah, we have.

[Doug]

I know it was very much a something burger.

[OG]

You know, it just was a week of. I was really busy, and I honestly didn't have dinner for two days before, mostly because William had baseball and I don't like eating late. So maybe subconsciously I was like, whatever, I'll just be hungry. I don't. You know. And like, maybe that was also part of it was I was already kind of on the downhill trend. Also, I didn't eat a pizza, like, the nanosecond before Drinking a gallon of Miralax. So, you know, there was. There was that. But, you know, I was hungry. My kids were like, are you hungry, Dad? I was like, yeah, I'm pretty hungry, actually. But, yeah, to your point, Joe, by noon I was. I mean, I took a nap, you know, because I just could. And if you're on the fence because you're like, I'm nervous about this, or I'm scared about the. The prep, or I'm scared about the.

[Joe Saul-Sehy]

Procedure, get it done.

[OG]

Do not. Yeah, it was so built up that it was that I was surprised. I was actually waiting for, like, the. The hammer to drop the whole time. I'm like, well, any minute now. And that. I told you this, Doug. The whole thing was so easy that I thought, well, the procedure must really suck, like, because somewhere in here is going to be awful. It was fine. So go do it. That's my public service announcement. I told you, Joe, there was nothing to this.

[Joe Saul-Sehy]

Yeah, that's very.

[Doug]

The last thing I want to say on the back porch is. And we just said we're getting a lot of great conversation on Spotify, but it seems like people are forgetting about Apple. We'd love to see some comments and some conversation on Apple.

[Joe Saul-Sehy]

Yeah.

[Doug]

So let's get that rolling, folks. Get back to Apple.

[Joe Saul-Sehy]

Come on, Apple.

[Doug]

We're still serving up a ton of episodes through the Apple podcast interface, so give us some. Some ratings and reviews out there, por favor.

[Joe Saul-Sehy]

We can't chat back right on Apple. They haven't given us that ability like they have on Spotify, but we can certainly chat on the show. Super fun. All right, that's going to do it for today. I think the big thing to learn is get your colonoscopy done. But if there's got to be three more, what do you think?

[Doug]

Well, here's my three. First, take some advice from Taylor Swift. Become really good at that thing. Not there yet. Time to start finding clarity so you're laser focused on what needs to happen next. Second, Roth IRA. Get that five year clock ticking ASAP so that after 59 and a half, your money is all yours to take and spend on your favorite podcast host. Slip that in there. But the big lesson. I wonder. I Wonder if that $2 billion Taylor made at Eras Tours includes all the swag she sold at the concert. Gotta have an 80T shirt, right?

[Joe Saul-Sehy]

Time to go refinance your house.

[Doug]

This show is the property of SB Podcasts, LLC, Copyright 2025 and is created by Joe Saul Sehive. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome [e-mail] 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]

Oh, yeah.

[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 advice. I'm Joe's mom's neighbor, Doug, and we'll see you next time back here at the Stacking Benjamin show. We had a fun thing happen at three in the morning last night.

[Joe Saul-Sehy]

I don't want to hear about your escapades at 3am There were zero escapades.

[Doug]

There was no escapading.

[Joe Saul-Sehy]

No escapading at all. What happened at 3am the bed broke as a result of escapades?

[Doug]

No.

[Joe Saul-Sehy]

Is that when you guys just high five each other?

[Doug]

Right? Yes. It's been 30 years of trying and we finally got it.

[Joe Saul-Sehy]

So you're sleeping. Your bed just falls apart.

[Doug]

Just the footboard of our bed just broke. And it's not even where the weight is. Us and the dog are all up at the top end of the bed. So, you know, I'm like 400 pounds and my dog's 200. But yeah, no, that's not where it broke. It broke where there's almost no weight.

[Joe Saul-Sehy]

We had the same thing happen with my nephews. We're visiting the right side of this guest bedroom. Bed just collapsed on my nephew. It was so bad.

[Doug]

On him or under him? Where was he sleeping?

[Joe Saul-Sehy]

He was sleeping, like, right in the middle of the bed. And he's like the right side support just collapsed. It's funny. It was a cheap Wayfair bed we bought a number of years ago. I was trying to put it back together, you know, just with duct tape and baling wire.

[Doug]

Yeah.

[Joe Saul-Sehy]

And this thing is so flimsy, we're sadly going to have to replace a bed.

[Doug]

This bed is not flimsy. And. Yeah. So. But I'm trying to decide. I got to take everything apart to get at it so I can figure out if it's even worth trying to save. And it's probably not going to be, but, yeah, just frustrating.

[Joe Saul-Sehy]

I'm not a big Fred Armisen fan. Are you?

[Doug]

I think he's talented, and there are moments where I think, wow, that was impressive. But overall, I can't say I'm a huge fan.

[Joe Saul-Sehy]

Yeah. Most of the time I'm like, yeah, no. OG You a Fred Armisen fan?

[OG]

I have no idea who that is.

[Joe Saul-Sehy]

So.

[Doug]

You do, actually. Fred Armisen is everywhere, but it's one of. He's one of those guys that you don't know his name every everywhere.

[Joe Saul-Sehy]

But I did see maybe one of the best things that he's done. And this is Fred Armisen's take. You know that series. I love Chef's Table. Love Chef's Table. And these chefs making phenomenal stuff. Fred Armisen does maybe the best Chef's Table spoof I've. I've. I've ever seen. I'm a traveler, travel a lot. One time I was on my way to Denver. I had to change to Chicago. I was in a real and I needed to get some food in me really quick. There was this sushi. It was just fishy, sweet for some reason, flavor. And as it came apart in my hand, I thought, ah, what is the city missing? I had this idea. I just came to this Alberta district and I said, let's open up a airport sushi. A couple years later, I had Kuko. At Kuko, we are proud to serve the most borderline not sushi sushi in the whole world. I want to make it like we have no love for it. I said, let's be the last people at the fish market. And everyone said, you have to be a smart chef who looks at your food and really considers it. I thought, no. Why? I want to be the chef that says, get this thing out of here. I want this to be the unifying sushi that anyone can eat. But nobody wants to eat airport sushi. That flavor of rice you don't get anywhere else where it's so hard, you actually feel like, am I eating bits of plastic? Open the fridge, please. See how this is.

[OG]

This got sent back. Great.

[Joe Saul-Sehy]

Yeah, send that one back to them again. Let's add a little something to it. There we go. Meaningless paper. He just puts a piece of paper over it. Send it back to. I thought that was genius. Just for a guy that watched a lot to Chef's Table.

[Doug]

He's good stuff. My favorite bit of his, also food related, is from, I think, what was Portland? What was the show?

[Joe Saul-Sehy]

Portlandia.

[Doug]

Portlandia. And they're in the restaurant asking about the chicken. The chicken. That is a genius bit.

[Joe Saul-Sehy]

We'll have to do that one sometime soon. Oh, geez. Fascinated by all of this restaurant talk.

[Doug]

Are we going to do a show soon? I've got business to attend to.

[Joe Saul-Sehy]

Says OG let's go eat.