It’s Taylor Swift week in the basement, and we’re kicking things off by looking at the business behind the beats. Joe, OG, and the gang pull back the curtain on the intentional, savvy moves that took Taylor from breakout teen artist to industry powerhouse—and why her playbook might just work for your financial life, too.
We’re talking about more than album drops. This episode covers:
- The power of controlling your own creative output
- Why strategic collaborations and timing matter
- How to avoid your own “sophomore slump”—in music or investing
- The underrated value of clarity, consistency, and small-but-steady improvements
Then, we take a sharp turn toward the world of Roth IRAs, answering a listener question about the five-year rule and clearing up common misconceptions. If you’ve ever been confused by tax rules or unsure when you can touch your money, this one’s for you.
Plus, there’s plenty more along the way:
- A local company stops making yardsticks (and we may be way too interested in that)
- Salutes to the troops, and a shoutout to basement podcasters
- A colonoscopy story you didn’t ask for, but will absolutely remember
Whether you’re a Swiftie, an investor, or just here for the financial clarity, this episode brings strategy, insight, and unexpected takeaways you can actually use.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
Doug’s Trivia
- Bernie Madoff’s infamous crimes stole a total of 18 billion dollars. The revenue generated by how many of Taylor Swift’s Era Tours would it have taken to equal that sum?
Better call Saul…Sehy & OG
- Stacker Eric has a question about when the 5-year waiting period starts for taking money out of a Roth IRA that’s funded from a rollover of Roth employer-sponsored plan money.
Have a question for the show?
Want more than just the show notes? How about our newsletter with STACKS of related, deeper links?
- Check out The 201, our email that comes with every Monday and Wednesday episode, PLUS a list of more than 19 of the top money lessons Joe’s learned over his own life about money. From credit to cash reserves, and insurance to investing, we’ll tackle all of these. Head to StackingBenjamins.com/the201 to sign up (it’s free and we will never give away your email to others).
Other Mentions
Join Us Wednesday
Tune in on Wednesday when we talk to the author of the book all about Taylor Swift’s business success, Kevin Evers.
Written by: Kevin Bailey
Miss our last show? Listen here: Conquering Investment Fears and Risks (SB1669)
Episode transcript
STACK 04-14 Swift Deep Dive -steve
[00:00:00] Joe: I just found out that there’s this, uh, company in town that makes yardsticks and I just found out they’re not making ’em any longer. God, be better. What is it? [00:00:13] Doug: OG left because of that. He just literally got up and left. That was it. We found the last straw. [00:00:23] Joe: That was the one that did it. All the jokes over all the years.And that’s the one, that’s the one that ended it. Oh, look it, he’s he, he is back. Uh, 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 at Make a Podcast to Mom’s Basement. Big salute like we do every Monday to our troops.
Keeping it safe. While we played all weekend, watching the Masters, having some fun, I was wandering around Michigan State University Ghost Party, ugh, yours to our troops. Trying to see if
[00:00:55] Doug: they would give you a degree finely please. I wait here for seven years. Know it’s here. I know it’s here somewhere.Here’s to our troops. Thanks everybody. This is my third double espresso this morning. Oh my God. In Fuego. Here it comes. It’s the fastest intro ever. Here we go. Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show.
I am Joe’s moms 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 are 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 hi in 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 up in my mouth a little bit. It’s Joe and oh ju.
[00:02:38] Joe: Hey there everybody. Welcome to Good Money Management in a Box podcast. I am Joe Saul Sea. Hi. 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 the car table from me. Mr. OGs here. How are you, brother? [00:03:01] OG: Great. Yeah, thanks for asking. [00:03:03] Joe: You have a good time. Uh, with the Masters last week, thinking about how next year you’re gonna be there on the course. [00:03:09] OG: I have applied for tickets every year since I was 19, and next year will be my 30th year of applications. [00:03:15] Doug: When is this guy gonna get the message? We’re not giving him tickets. [00:03:18] OG: You’d think I’d get the, uh, hint, but, uh, 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, right?
[00:03:40] Joe: But yeah, you thought, by the way, the Costco hotdog was iconic. I. Like the master’s food prices for such a high end tournament iconically low. Yeah. Viewers [00:03:48] OG: are a dollar 50 or something. [00:03:49] Doug: Anyway, you can buy one of everything on the list for $77 [00:03:53] OG: this year.Okay. That seems like a big list because I’ve seen like, yeah, may maybe, maybe the list is, anyway, it doesn’t matter.
[00:03:59] Doug: There’s like 30 [00:04:00] OG: things available. [00:04:00] Doug: I [00:04:00] OG: mean it is dirt cheap. So anyways, the company that does the catering, you can order the master’s party kit. [00:04:06] Joe: How fun is that? And so they [00:04:07] OG: send you a jug of pimento cheese to put on sandwiches, a jug of egg salads and potato chips, little cups and stuff.So anyways, that came, we had a little master’s party, uh, played a little part three tournament on Wednesday. Just kinda fun. Oh, cool. You know, we move, we moved the tee boxes around so that they’re different shots.
[00:04:23] Doug: Yeah, [00:04:24] OG: it’s just kind of a fun week. [00:04:25] Doug: Just skip one across the water. [00:04:27] OG: And, 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, go. [00:04:35] Doug: I can blade a gap wedge fast as well as anybody. [00:04:38] OG: Yeah. So, uh, 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, uh, we just kinda laid low, just stayed out of the news cycle. Does anything major happening?I’m kind of unaware.
[00:04:54] Joe: 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. Uh, we’re gonna 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 uh, now he has his, uh, first book.There’s nothing like this. There’s 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 before, well, I. 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 her co-write every song on a platinum selling Country album.
And that just obviously begins this, this long run and then on and on. Yeah. And the stuff that Kevin has dissected from her career and he’s brought in all of these different experts in different fields to talk about. I’ve grabbed some of those today and we’re gonna 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.
[00:06:26] OG: Yeah, we are. We are Swifties here. [00:06:28] Joe: You’ve got some swifties in the family.All right. We’re gonna 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.
All right, oie, 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 OUTTA college, for me, that was pretty difficult. Like, what’s the thing I’m gonna end up doing? Now, 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 Vet, 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 gee, they know what they’re building. They know where they’re going. I think, uh, 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 regimens.
[00:08:33] OG: I think maybe our, uh, 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, you know, 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 like 40 years when my kids aren’t like adults, would they write their expose about Dad? 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 gonna be the Pulitzer Prize winning author, right? 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 Eng.
You know what I mean? Like you can take normal, just get a B, but you have to get an A plus in math. So you’re gonna take the hard, you know, if math is your thing, you’re gonna take the hard math. You don’t get to take easy math because it’s easy for you and you like it. You’re gonna 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, 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 wanna repeat. If you come home and you’ve had a good day, but you’re drained, that doesn’t mean that it, you know, you can’t do those things, but that’s not the thing that’s gonna provide, that never ending energy.
It
[00:10:45] Doug: usually means I went to the bar first before I got home. Yeah, could be. [00:10:49] OG: 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, and I’m just making it up.Maybe her tour days are, you know, 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.
[00:11:10] Joe: 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.Like just immediately she’s like, yeah, we’re not doing that. I mean, to 50-year-old men who’ve been in, in Nashville for 30 and 40 years, you know, she’s, she’s like, no, yeah, uh, 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 gonna talk about that goes back to just a couple weeks ago, the Molly Fletcher week, where we 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 wanna 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 that I just like ’em all. I. 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 markets kind of bumpy and you’re, you’re not at all concerned.
[00:12:30] OG: Yeah. I don’t know that anybody’s not concerned. I mean, this is, I wrote an email a couple 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.
[00:12:43] Joe: But you have a degree of faith that your money’s gonna be there when you need it. Yeah. Because you know roughly when you’re gonna need it. [00:12:48] 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, you don’t really have a measuring stick or your only measuring stick is performance.So your barometer for success is gonna 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, 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 choice, you know, year ending Feb, 19, 20, 25, 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 gonna 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% in 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, 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, the range of expectations. If your confidence is lacking, you’re more likely to make a change.
[00:14:58] Joe: And I think that confidence though, gee, 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.
[00:15:51] 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, oh yeah, yeah. I’m good at this and I’m gonna do it and I’m gonna do it. I’m gonna do it. The reason that maybe one of the reasons that that ratio is one outta two or one out three or one. Well, you know, whatever number you said is because she got a lot of it 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.
I. 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 so many Wow. Three
[00:16:31] Doug: albums. Yeah. [00:16:33] OG: 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? You know how many. I think that’s
[00:16:49] Doug: the key point. Yeah. [00:16:50] OG: 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 gonna finish ’cause we’re recording this a little bit beforehand. The number one range ball hitter was Bryson de Shambo. He hit 390 range balls on Tuesday before the masters. For me, that would be like one normal round of golf. Like 390 shots.
[00:17:33] Doug: 300. And I know, and we know how our body feels after those 390 shots.Yeah. Imagine what he has to do.
[00:17:40] 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, not going all out the two day, you know what I mean? [00:17:51] Joe: Well and to your point, when the critics came, I’m gonna fast forward away. We’re gonna go back to the beginning days.Turns, turns out
[00:17:57] OG: Taylor Swift was successful [00:17:59] Joe: 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, uh, Petridis, I think is how you pronounce it, Al Alexi Petridis. He says that Leanne Rhimes and Shania Twain had done it before Swift, but dated 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.
[00:18:46] OG: Exactly. [00:18:46] Joe: But Swift has left some of the, you know, those country sounds in songs like, uh, love Story. I think most of us have heard the pop song love story like Romeo and Juliet. Give us a little bit of it. Joe, Doug, can you sing?How’s it go? Uh, it’s a love story, not a note, but here’s what he said. 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 un inventive, but does it incredibly well.
[00:19:17] OG: Very British way of saying nice things. [00:19:20] Joe: He is not a fan. But the point is, is that I think a lot of us think we gotta reinvent the wheel, right? We gotta 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 gonna get there.But this British guy is talking about, I think what is is truly the truth about what Alex r Moey 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 gonna happen?
You’re gonna make a better meal than somebody that took half of those reps.
[00:19:57] OG: Yep, a hundred percent. [00:19:58] Joe: 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 Leon Rimes 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, that when you got old dudes in a Ford pickup truck, are they gonna listen to this crap?
Really? Is this gonna be it? She knows that’s what she’s up against from the very beginning. And I think that, that, you know, we talked, uh, last week about risk in your portfolio. I think knowing what the challenges are gonna be as you’re walking this, uh, 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 gonna have to prospect for new clients then. Then 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, I gotta 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 gonna be the issues that are gonna come up, and I’m not gonna 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.
[00:22:04] 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 in this, 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. 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.
[00:22:45] Joe: I think though, gee, 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. [00:22:57] OG: I remember I was thinking about when I was in bootcamp, I remember the never ending p ting and never like just the never ending hikes where you like 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 like in the middle and it always sucked. And I remember one time thinking. I just need to break this down into periods of time. Like, like eventually they’re gonna feed us lunch. Like this seems like pretty regimented in terms of schedule.
Like we’ve always gone to bed at nine 30, we’ve always got up at five 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 gonna eat and so it was like, okay, I got up, it was chaos.
Now I get breakfast and now I know it’s gonna 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, well that’s the 7 37 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 bootcamp 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 ’em, right? You’re like, okay, there’s a Southwest, then there’s the United and there’s the American jet. You know, you just like, do we ever do that?
[00:24:38] Joe: Running today at nowhere near bootcamp. So I don’t wanna make a bootcamp reference, but 6 0 5, the American Airlines flight goes overhead while we’re on a run. [00:24:46] OG: Yeah. [00:24:46] Joe: Like every day like clockwork, the 6 0 5. And if you’re in a [00:24:49] OG: different spot, you’re like, I’m ahead of pace, I’m behind pace. That’s right. So, so we just kinda 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, minus. 20. At this point we are exponentially closer. Hmm. Infinitely. It’s a time-based one. Lemme 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. You know, 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 a hundred because it’s statistically impossible to be minus a hundred. You could be minus infinity if you go to zero, but it can be 99%.
[00:25:44] Joe: That’s the good news. News, news from stacking Benjamins. We can only go to minus infinity, not minus a hundred. [00:25:50] 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, and it provides you a just that little bit of hope I.As, as bootcamp transpired, it was like, okay, there’s three phases and there’s three meals and there’s, you know, it is 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.
But
[00:26:18] Joe: what is that? That is, that is knowing the challenge plus reps, because you’ve been out there enough. I know that flight going over, I know this flight going over. Yeah, I know. So to the points that we made earlier, reps, super important. Knowing the challenge is super important and having that vision that I’m gonna make it to freaking lunch. [00:26:35] OG: Yeah. 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. [00:26:45] Joe: I wanna bring up one more thing just before the break. It’s Joey Donut. Oh, which is that I think. Then the next thing we couple together is who we surround herself 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 gonna work for me ’cause 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 in 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 wanna write a hit song. They want their name on a hit song. She wants to write a hit song. Bors Sheta 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 ourself 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, 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.
[00:29:04] 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, you know, 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, that’s not gonna work because I.
You know, we’re gonna be butting heads. And I think you can do that in a lot of settings in a good way. As long as you know, it comes from a position of respect. And you said vision, I’d say, you know, love, maybe even just like 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, alright. 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 know,
[00:30:18] Doug: I knew it. I knew he couldn’t make it all the way through.That just found, finds a way to work it back in Doug.
[00:30:25] OG: No, I’m just, I mean, that’s what your mom said. [00:30:29] Doug: Work [00:30:29] OG: it back in. [00:30:33] Joe: All right. I think on that, now 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 gonna dive into her second album and the sophomore slump. We’re gonna talk about the sophomore slump.’cause I think people also have this in their careers. There’s a ton we can learn also about our portfolio there. Uh, we’re gonna do that and we’re gonna 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.
[00:31:05] Doug: Just fact packed.Joe. Hey there, stackers. I’m Joe’s mom’s neighbor Doug, and I mean, whew. What a, what a big time, horrible day. This is first tomorrow’s tax day. I haven’t even started. Oh man, you neither. Second I’m looking up trivia for today. And, you know, Lincoln was shot on this day in history. Well, that was a bad day for the nation, but arguably it even worse for him.
Oh man. No. Too soon. Well, is that too soon? Okay. Alright. It’s also the day in history when the Titanic sank. Bad day for us, but probably a worst day for the past. No. No. Okay. I’m not gonna, I’m not gonna say it. I won’t say that one. It might have been slightly worse in 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. That’s a good one. 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, whoa. Oh, I got it. Itch.
Hey there, stackers. I’m singer songwriter and guy who’s all about the rhymes. Joe’s mom’s neighbor, Doug. Well, that didn’t rhyme back in 2021. On today’s date in history, Bernie Madoff passed away 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’ve taken nine really.
Yeah. Nine A tours to equal the amount of damage Madoff cause. 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? I dunno, who knows? I wasn’t looking. I didn’t realize he was going. 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, uh, old college friend Christopher. Remember him? Yeah. Yeah. Good guy. 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’ve been taking over the starter job as a freshman. He was starting catcher on the baseball team all four years. Try it out as a walk-on for Purdue baseball team. Was the last person cut? You’re a pretty good ball player if you can try to walk onto a Big 10 team and. Almost make it 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 uh, 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. I thought it was, he was just focused on too many things. Like too many maybe. But it was just show this guy was talented at whatever he tried to do.
[00:35:08] Joe: He exude that the first time I met him, first time I met him, I’m like, this guy’s good at stuff. [00:35:12] Doug: Yeah. And oh, by the way, ridiculously good looking. [00:35:16] Joe: Yeah. I [00:35:17] Doug: mean, I saw that in your eyes the first time you saw him too. [00:35:20] Joe: Like us. Yeah, like us. Yes, very much. It is so interesting, this idea of being good at the one thing, like picking the one thing and having the clarity around the 1 1 1 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. If you guys ever heard the phrase, the sophomore slump. Oh yeah. Do you know where that actually comes from? Because I had no idea where, I thought that was a musical term, right? Yeah. It’s not because I was 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’s at 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 OG you and I worked, you know, back in the early nineties 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 Su 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 had s had freedom from. So you did none of them you, you did none of the things anymore that made you successful.
I
[00:36:53] OG: mean that’s true for everything. You have success working out and you go, boy, I look really good. I should go have a donut to celebrate. And it’s like, it’s unfortunate because we want to be focused on the results and have results be the 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.
[00:37:22] 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 are 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 gonna make it repeatable over and over and over again.
[00:37:50] Joe: It a hundred percent. 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. It’s interesting that 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 a hundred percent not sustainable. She went on the Ellen DeGeneres show at one 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. She stops doing it. Instead, she does it in her songs. And so ever 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, uh, Sonya 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. ’cause 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, we let it power us. 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 gonna be as big? Some artists don’t get it at all. Like Madonna never had a sophomore slump. Katie 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. U2 Bon Jovi, uh, had these albums that, uh, 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. Hootie 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, the, just widening this out by getting money early on. We talk about later on, you get to maybe a hundred thousand dollars. You need to know how to diversify. Maybe get to a hundred thousand dollars, 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 gonna happen next.
[00:41:22] 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, you know, when you do your financial plan or you pull out a calculator and say, okay, I’ve got a hundred thousand dollars and I’m gonna put in 20,000 a year, my 401k, and it’s gonna grow at 10% a year or 8%, whatever number you wanna 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, it’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 a hundred K 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 in later in life. I talk about this all the time. I’d have no idea why people would get to 65 and then turn conservative. And it’s not a, it’s not a, 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 gotta, because you bought and owned the biggest companies in the world and then all of a sudden you get 65. Yeah, I don’t wanna do that anymore. That worked too good. It’s like, I finally have 3 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 one’s a lot less pressure
[00:43:32] Joe: around the quote sophomore slump when you just love the thing. Yeah. That pops a lot of the balloon, like let the outcome take care of it.So if your outcome based, the sophomore slump is gonna hit hard.
[00:43:43] OG: Well, and 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 to roll to my problems in a limo.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, you know, that’s a new thing. And that triggers new stuff and, 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 a hundred K or a million. It’s like, you know, whatever. Charlie Munger said, the first a hundred K is the hardest. Right? As soon as you get that, you’re good. You think there’s gonna be unicorns and rainbows and Yeah. Nobody’s, you know, ed McMahon didn’t show up with a, is he dead? I think he’s dead.
He is. You know, he Ed McMahon, the people, dunno who that is, doesn’t show up with a big check in balloons. Right? And go like, Hey, say Ed
[00:44:59] Joe: McMahon shows up now we’re in big trouble. [00:45:02] OG: Ed McManns at the door. Oh crap, they’ve cloned wolves from 10,000 years ago. Why don’t they clone something good like und man?You know? And it’s like you get to a million bucks, you’re like, oh my gosh, I hit my financial independent 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 a. The things along the way.
[00:45:35] Doug: Well, this is also why, and Joe, we, 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, for my clients, know that you’ve gotta 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.
[00:46:21] Joe: 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 gonna 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 gonna talk about, uh, imagine if you are
[00:47:09] Doug: the ex-boyfriend and you realize I was just part of the process.Mm-hmm. She didn’t really wanna date me. She just needed, she just
[00:47:16] OG: needed a new muse. [00:47:17] Doug: Yeah. Swift is like, I had to go out with you. What was [00:47:19] Joe: I gonna do? You’re a, my contract says I need another album. I needed a hit song. And everybody knows you’re a moron, so, [00:47:29] OG: well, they’re about to know you’re a moron. That’s, they didn’t already [00:47:32] Joe: way more than they did before.But you know, we’re gonna talk about the, using this process to differentiate yourself and to constantly be changing next week, because this week we are talking strategic. Next week we’ve got Lorraine Leon, who for a long time was with LinkedIn and uh, it does a great job tactically of helping people with their career.
So that’s gonna be kind of the other shoe. But on this album, she doesn’t go completely pop, which is, we all know is where she’s headed literally this morning. I was talking to Cheryl about what this discussion was gonna be, and she goes, really? Taylor Swift started off in country. Like she, she had no idea.
Wow. She had no idea.
[00:48:08] OG: Even I knew that. [00:48:09] Joe: Right. These, 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 knows she’s going toward pop.Why? Because now that she’s made it into the closed loop, the country music is, and now that these old men in 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.
I. 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 gonna 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 who 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 every day, when I do that, I’m now gonna attach another habit to it and just incrementally, that’s gonna 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 gonna dive deeply with the guy that literally wrote the book about this on Wednesday. We’re also going to, on Thursday, have our 2 0 1 newsletter, all about your career, your investments, and on Friday we’re gonna do this cool round table with og.
Financial planners, Alyssa Maes and Roger Whitney on the eras. Get it. The eras. Yeah. 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 gonna 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 gotta call Saul. See. Hi and og. If you need us to help you, head to stacky benjamins.com/voicemail and you can be as cool as Eric who’s called us.
Eric, what’s on your mind? My friend
[00:50:52] caller: Joe and og, I have a Roth TSP and Roth 401k. When I retire, if I roll that over into a Roth ira, does the five-year waiting period start then assuming it’s after age 59, or do I need to do a Roth backdoor 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. Love the show.
[00:51:23] Joe: Oh, great question, Eric, and this is just a little trip wire, I think the trips a lot of people up when it comes to the Roth, this five year rule, og, how does that actually work? [00:51:32] 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 one 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 four.
The 2024 tax year. You know, you just wait till the last second to put money in. That counts as of January 1, 24. So it’s 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 a 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 4 0 1 Ks 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. You’ve been contributing for five years, or you started it five years ago, or you put your first contribution at five years ago. When you roll that over, when you retire to your Roth, IRA, you’ve already, your five year clock has already started. Basically to say it a different way.
So if, if you’re 55 and you started putting money in your Roth, when you Roth 401k, when you’re 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? You’ve,
[00:53:04] Joe: you’ve already got it because of the other Roth account. [00:53:06] 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.
[00:53:14] Joe: 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. [00:53:21] OG: Yeah. You know, and it’s the same thing for like 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 wanna have that going as soon as possible.
[00:53:38] Doug: You talked about conversions, and it made me think, I know we’ve got a lot of listeners with 4 0 3 Bs. Any difference there? Nope. Is it all same? Same? [00:53:46] OG: Yeah. Same. Same. I mean, 4 0 3, all, all retirement plans are the same. You know, four oh K, 4 0 3 B, four 50 sevens, although I haven’t really heard of Roth 4 57.So that doesn’t mean they don’t exist, but any Roth product, it’s all treated the same.
[00:54:00] Doug: Okay, [00:54:01] Joe: 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.Stacky benjamins.com/voicemail. Again, if you’d like, uh, us to answer your question, let’s, uh, meander before we say goodbye, off to the back porch. Put our feet up after a nice, uh, episode. Doug, what’s going on in the community? Man?
[00:54:26] Doug: Hold on. Let me pour myself a drink first. Oh, look, it’s already here, huh?Imagine Joe, I don’t know if you remember last week we did a special episode. Do you, I can’t even remember what it was about. What actually
[00:54:39] Joe: did we cover on [00:54:40] Doug: that last Tuesday we did a special episode, uh, because it had been a couple of days of very tumultuous market. Ups and downs. Really. 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 a, a great new place that people can leave feedback for us. Appreciate that. We’ve been just
[00:55:29] Joe: really chatting it up on Spotify. Yeah, it’s been really fun. [00:55:32] 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. I am the, I’m one of 11 people still on Apple Music, but I hear that there’s some great stuff happening in there. Anyways, JD Dozier said, great episode, very timely with OGs. Colonoscopy and Doug’s story couldn’t help but to laugh out loud. Pretty sure he was laughing at your colonoscopy.
Uh, I was fresh out of recovery from my own. Hard to believe we can learn anything from this show.
People still say that. I, I, it’s amazing to me. That’s how you know you’re a long time listener because we haven’t said that in like 10 years. We don’t want you to learn anything. So I’m gonna, I’m gonna
[00:56:11] OG: circle back to that. Thanks for bringing that up. Doug, because, uh, 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 no, [00:56:26] Joe: no better way to end an episode, but with a colonoscopy discussion. [00:56:29] OG: Joe is, Joe is so senior, he’s done with them. Apparently you get to end at some point, but anyways, [00:56:34] Joe: I just gotta show ’em the card. No, I had it, [00:56:36] OG: it, it’s like a punch card, you know, you’re like, I get this one free. So this was my first one and I, 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 gonna go do something funny. Public service announce, but I’m not, this isn’t fun.
[00:56:53] Joe: I thought Doug already made the public service announcement. I’m saying don’t eat a pizza at 7:00 PM Yes. It’s not about that. I’m trying [00:57:00] OG: to do [00:57:00] Joe: the right thing. [00:57:01] OG: Okay. Yes. Do it, do it for me.It was a non-event. So I’ve had this scheduled and rescheduled the schedule, reschedule. I, you know, conveniently had stuff come up. Finally, I was like, all right, I just gotta 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 gonna 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 three o’clock in the afternoon and I probably could have gone to my son’s baseball game, which was seven.
What, what time
[00:57:44] Joe: did it happen at in the afternoon? Late afternoon? [00:57:46] OG: Um, the process that I had was at 12 o’clock. I took four over the counter pills. Oh, oh. Did the stuff. I see what you mean. Yeah. At one o’clock I took a Zofran and then two o’clock started drinking the over the counter stuff with Gatorade.And um, 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 the, go to the hospital at six in the morning. That kind of sucked. But I went to bed at nine. I got up at five 30.
I slept all night. I was fine. I thought the night
[00:58:20] Joe: before for me, the cleansing piece, very bad. But the event, to your point, that day, like by noon, I was great. Like I was, I was fine. Yeah. [00:58:30] OG: 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.Sono, this is what’s what we’re doing. You know, they hit me with the propofol and I was out in an instant. Like, I didn’t, I wasn’t, people were like, try to count backwards. See, I’m like, I don’t care. I’m going to sleep, man. I like sleeping. So, so I was like, I’m this, like, I have no desire to be awake for it.
I’m not gonna 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 omelet and two orders of french toast. I didn’t eat there ’cause 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, ah, this is gonna 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.
[01:00:08] Doug: I find it very curious that you said that it, uh, or at least a turn of phrase you used when you said it was a nothing burger because have we talked about the, the pizza? Yeah, we have. I know it was very much as something burger scene and you [01:00:20] OG: know, it just was a week of, I was really busy and I honestly didn’t have dinner for two days before, mostly ’cause 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 um, 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, ’cause I just could and I. 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 procedure, get it done. 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 they, 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 gonna be awful. It was fine. So go do it. That’s my public service announcement.
I told you, Joe, there’s nothing to this. Yeah. That’s very nice. Joe, the
[01:01:29] Doug: last thing I wanna say on the back porch is, and, and we just said we’ve, we’re getting a lot of great conversation on Spotify, but it seems like people are forgetting about Apple. We, we’d love to see some comments and some conversation on Apple.Yeah. So let’s get that rolling folks. Get back to Apple. Come on Apple. We’re still serving up a ton of episodes through the Apple Podcast interface, so, so give us some, some ratings and reviews out there. Por favo.
[01:01:56] Joe: We can’t, uh, 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 gonna do it for today. I think the big thing to learn is get your colonoscopy done, but if there’s gotta be three more, what do you think? Well,
[01:02:14] Doug: 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 tailor made at ERAS tours includes all the swag she sold at the concert.
I gotta have an $80 t-shirt right? It’s
[01:02:52] Joe: time to [01:02:52] Doug: go refinance [01:02:53] Joe: your house. [01:02:55] Doug: This show is the property of SP podcasts, LLC, copyright 2025, and is created by Joe Saul Sea. Hi, Joe gets help from a few of our neighborhood friends. You’ll find out about our awesome [email protected], along with the show notes and how you can find us on YouTube and all the usual social media spots.Come say hello. Oh yeah. And before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s Mom’s neighbor, Duggan. We’ll see you next time back here at the Stacking Benjamin Show.
We had a fun thing happen at three in the morning last night.
[01:04:31] Joe: I don’t want to hear about your escapades at 3:00 AM. [01:04:34] Doug: There were zero escapades. There was no [01:04:37] Joe: escaping, no escaping at all at 3:00 AM what happened at 3:00 AM [01:04:40] Doug: the bed broke [01:04:44] Joe: as a result of escapades?No. Is that what you guys just high five each other,
[01:04:53] Doug: right? [01:04:53] Joe: Yes. [01:04:56] Doug: It’s been 30 years of trying and we finally got it. So, so you’re sleeping and your bed just falls apart. 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, uh, yeah, no, that’s not where it broke. It broke where there’s almost no weight.
[01:05:25] Joe: We had the same thing happened with my nephews. We’re visiting the right side of this, uh, guest bedroom bed just collapsed on my nephew. It was so bad [01:05:34] Doug: on him or under him. Where was he sleeping? [01:05:37] Joe: He was sleeping like right in the middle of the bed and he’s like, the right side support just collapsed.And 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 bailing wire. Yeah. And this thing is so flimsy. We’re sadly gonna have to replace a bed.
[01:05:55] Doug: This bed is not flimsy. And yeah, so, but I’m trying to decide, I gotta 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 gonna be, but yeah,
[01:06:09] Joe: it’s just [01:06:10] Doug: frustrating. [01:06:11] Joe: I’m not a big Fred Armisen fan, are [01:06:13] Doug: you? 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 though. [01:06:21] Joe: Yeah. Most of the time I’m like, yeah, no. Do OG you a Fred Armisen fan. I [01:06:27] Doug: have no idea who that is.So 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
[01:06:36] Joe: every everywhere, but I did see maybe one of the best things that he’s done, and this is Fred Arman’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.
[01:06:58] bit: I’m a traveler. I travel a lot. One time I was on my way to Denver. I had to change to Chicago. I was in a real rush 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. Couple years later, I had Cuco. At Cuco. We are proud to serve the most borderline, not sushi, sushi in the whole world. I wanna make it like we have no love for it, but up.
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 outta 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? Fucking the fish. See how this is, this got sent back. Great. Uh, yeah. Send that one back to them again. Okay. Let’s add a little something to it. There we go. Meaningless paper.
[01:08:25] Joe: He just puts a piece of paper over it.Send it back to him. I thought that was genius. Just for a guy that watched a lot. The chef’s table.
[01:08:34] Doug: He’s good stuff. My favorite bit of his also food related is from I think, uh, uh, what was Portland? What was the show? Portland. Portland. Portlandia. Portlandia. And they’re in the restaurant asking about the, uh, the chicken.The chicken. That is a genius bit.
[01:08:50] Joe: We’ll have to do that one sometime soon. Oh, gee’s. Fascinated by, yeah. All of this restaurant talk. [01:08:56] Doug: Are we gonna do a show soon? I’ve got business to attend to, says og. [01:09:00] Joe: Let’s, let’s go eat.
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