Harvard Business Review’s Kevin Evers on the Genius of Taylor Swift (SB1670)

What Taylor Swift teaches us about strategy, long-term thinking, and building an empire.

Taylor Swift isn’t just a pop icon—she’s a master strategist. And in this episode, we unpack exactly how she built a cultural and financial empire with smart moves that offer powerful lessons for any Stacker.

Joe Saul-Sehy sits down with Kevin Evers of Harvard Business Review Press to explore:

• How Taylor’s early partnerships set her on a path most artists never get to walk
• Why a clear vision—and the discipline to stick to it—can be a superpower
• How she turned frustration into creative fuel and conflict into leverage
• The surprising role MySpace and radio tours played in her initial success
• And what her story teaches us about marketing, risk-taking, and ownership

But the show doesn’t stop there. Joe and OG also dive into:

• Grant Cardone’s 401(k) comments and whether his hot takes hold up
• The risks and rewards of real estate
• What crypto storage, insurance, and documentation mean for your financial safety net

Plus, Mom’s neighbor Doug jumps in with a tax-themed trivia challenge—and a few surprising family stories to bring it all back home.

Whether you’re a Swiftie, a strategist, or someone just trying to make smarter money moves, this episode delivers sharp takeaways and fresh perspectives.

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

Enjoy!

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Our Headline

• For bitcoin bulls who self-custody crypto, the global risks are growing (CNBC)

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Doug’s Trivia

• If you decided not to file your taxes by yesterday, what day are they now due, assuming you filed an extension?

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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).

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Join Us Friday!

Tune in on Friday when we discuss the sheer longevity of Swift’s reign at the top of the music industry and what it takes to notch money victories.

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Written by: Kevin Bailey

Miss our last show? Listen here: Money and Business Lessons from the Career of Taylor Swift (plus a BIG Roth IRA rule clarified) SB1670

Episode transcript

STACK 04-16 Kevin Evers -steve

[00:00:00] bit: Okay, right here it says right here in this, this account we have $401,000 

check put. Nope. Uh, that says you have a 401k account. If you liquidate that right now, you’ll have, you know, maybe $5,000. 

So what happened to the other $396,000? 

What is wrong with the two of you?

[00:00:28] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show.

I am Joe’s moms neighbor, Doug. And how do you follow up our deep dive into the genius of Taylor Swift on Monday? You talk to the guy who literally wrote the book on the topic today, we welcome from Harvard Business Review Press, Kevin Evers Plus in our headline, one publication is Worried Your Crypto Stash might not be as safe as you’d think.

How do you protect your digital assets? We’ll share, and don’t you worry yourself even a little bit because I’ll be sure to amaze you with some incredible trivia. And now two guys who are the Taylor Swifts of financial podcasting. It’s Joe and OJG. One of ’em looks great in Titan.

[00:01:32] Joe: I was gonna say, no laughing. While you’re doing that, Doug. No laughing while you’re saying that. Come on straight face. Hey everybody. Welcome to our version of the ERAS tour. It’s been 15 years on this ERAS tour as we circle the globe with money. Goodness. We have t-shirts in know over 48 countries.

Remember those cool t-shirts we made for our comedy club tour a few years ago? That was fun.

[00:01:54] OG: A few years ago. 

[00:01:55] Joe: Well, it feels like, like a long time ago. Hey everybody, welcome back though. We’re super happy you’re here. Sit back, relax, because on today’s show we’ve got the man himself from Harvard Business Review, one of their chief editors, and he’s the guy who has literally written a book about Taylor Swift.

Kevin Evers joining us. OG Sweet. I know it’s gonna be great. I loved our discussion on Monday. If you didn’t do the deep dive, no worry, you can start here. But if you enjoy the conversation with Kevin, go back and listen to Monday show, because we’re we’re bringing it there. Of course, we had, uh, stacker, Jill, send us a TikTok that I can’t wait to play for you two guys.

I’m just, I’m excited to see, uh, what’s you’re gonna think of that. It’s just, it’s, this is a gift. This is a show that just is gonna keep on giving today. You know, the first thing we’re gonna give you is the Kevin Evers. He has spent his career at Harvard Business Review. He’s a senior editor there. He is a guy who loves taking groundbreaking research and amplifying ideas.

He’s edited, bestselling and award-winning books on high performance, creativity, innovation, digital disruption, marketing and strategy. He’s put them together in this, his first book, man. What, uh, what a deep dive it is, if you like, case studies. It’s called, there’s nothing like this, the strategic genius of Taylor Swift.

We’re gonna talk to Kevin about what he learned from Taylor Swift about all of those things. Before we get to Kevin though, we have a couple sponsors that make sure this is free and you don’t gotta pay a dime for great guests like Kevin. So we’re gonna hear from them, people that make this possible. And then front and center, today’s mentor, the Kevin Evers joining us.

And I am super happy. This gentleman’s coming down to the card table. Kevin Evers is here. How are you man? I’m doing great. How are you? I’m doing very well. You dive into case studies with your work and businesses and how they work. Of course, Harvard Business Review, and I imagine that’s in your DNA, it’s in our DNA to look at businesses, so I’m thinking Amazon, I’m thinking all these different, uh, cool Co Apple.

Why in this project, why, why Taylor Swift of all things, Kevin, 

[00:04:21] Kevin: I have to say, it did not take much soul searching to do a case study or a book on Taylor Swift. She’s has great entrepreneurial instincts, right? She’s a great songwriter, but there’s no way you can get to this point in her career if you don’t have great.

Business instincts. I mean, the numbers around her career right now are pretty staggering. The Airs tour grossed over $2 billion. That’s nearly twice as much as the second highest grossing tour, which belongs to Coldplay. And in 2024 alone, swift, just her album sales, just her streams accounted for close to 2% of the total music market.

Those are big numbers, right? So I really wanted to unpack how she’s been able to do what she’s been able to do for so long. So I didn’t approach this book any differently than I would if I was writing a book about Steve Jobs or Jeff Bezos. 

[00:05:08] Joe: I always get interested in the art of diving into a company, or in this case the company that is Taylor Swift.

[00:05:16] Kevin: Yep. 

[00:05:16] Joe: You begin with her collaborators and the collaborations that she has early on. I wanna, I wanna give you a name and if you can explain to our stackers who this is and why you begin here. This guy’s name is Robert Ellis Oral. Can we start with him? 

[00:05:29] Kevin: Yeah, let’s do it. Robert was a, or still is a, a songwriter in Nashville at the time.

Taylor Swift was signed to a development deal with RCA Records. She’s about 13, 14 years old at this point. Right. So, RCA, one of the biggest labels on Nashville’s music Row really saw the potential in Taylor, even though she was so young. And so she worked with Robert on her demos and writing songs with him, co-writing songs with him from a very early age.

[00:05:58] Joe: I’m just imagining Kevin, you know, he gets this, I, I dunno if it was an email at the time or, you know, ’cause this is way back when, but if it’s email or a letter or a phone call or whatever going, Hey, you gotta meet with this 13-year-old. Like, are you, are you freaking kidding me? 

[00:06:10] Kevin: Yeah, for sure. That’s another thing that surprised me is Taylor Swift was very young at the time and she’s writing with men who were 2, 3, 4 times her age.

That definitely was his reaction. It’s like. Wow. Okay. And a lot of people’s reaction too, they’re like, okay, I’m, I’m gonna go right with a 13-year-old girl. ’cause this wasn’t pop music. It was really rare for someone so young to try to make it in country music. ’cause country music did not believe that there was an audience.

14 girls. She was an anomaly. She was a unicorn. And a lot of people did react positively, but a lot of people did question why they were in a room writing with a 14-year-old girl. 

[00:06:45] Joe: You said at one point, uh, and we’ll talk about this later, but another guy that she collaborates with later on, she really, really wants to define herself by the people she’s around.

And for all of our creators in the audience. Kevin, this is something that resonates for me as an entrepreneur too. You are who you surround yourself with. 

[00:07:04] Kevin: Oh, without a doubt. Taylor made a lot of bold decisions early on in her career to work with people who you wouldn’t think that she would work with them.

I mean, she had that development deal with RCA, but she left RCA. That’s a bold decision as a 14-year-old to say, yeah, you know what, I have this interest from a major label, but I’m gonna, I’m gonna bet on myself. They don’t believe in my vision and I’m gonna go somewhere else. And she ended up going with a man named Scott ceta, who founded a indie label called Big Machine Records.

But at the time, he didn’t have funding. He didn’t have a headquarters. His startup didn’t even have a name. Right. And he wasn’t selling his contracts outta the back of a Buick. He was a longtime industry vet. He was a great promotions guy, worked for Universal Label Group, but Taylor thought, Hey, he believes in my vision, so I’m gonna go with him instead of going with a major label, which was a big decision now in hindsight, that definitely worked out for her.

[00:08:01] Joe: What did people, her, these early collaborators, like Oral, uh, say about her in the early days? Like what was the vibe, the sense they got from her? I mean, 13 years old, this girl comes into the room, what do they think about her once they actually meet her? 

[00:08:15] Kevin: Very, very impressed. The ones who were in her corner and really thought that she could make it in country music, walked away with the feeling that they’d never seen someone at such a young age who had such a clear vision and who was so headstrong too.

And that was the part that surprised me. ’cause I didn’t know much about her early career. So when I was researching for the book, I almost didn’t believe it. Right? Because there are quotes from Robert Orle in the book where he says, this girl’s gonna sell a million copies of her album. After the first day he met her.

And I was like, oh, okay. Like you could say that in hindsight, but there are so many other executives. When I went back and looked at old interviews who said the same thing, they’re really shocked at how clear of a vision she had. She knew who she wanted to be as an artist, and she knew what audience she wanted to hit.

[00:09:03] Joe: I was thinking as I was reading your words, how do we create this? Like how do we recreate this? What can we do on this podcast to help our stackers maybe. Come to the table and have people impressed by us. Whether it’s a negotiation with my boss to, you know, for a raise or with a customer, or heck with our career for an entrepreneur.

And you really, it seems to me, reading between the lines, well, like you are impressed by her preparation. Even at 13 and 14 years old, this young woman shows up, Kevin to every meeting, intensely prepared. 

[00:09:35] Kevin: Yes. She knew that she was walking into rooms where people were gonna be very skeptical of her. So she said, I’m gonna come in prepared.

I’m gonna have multiple songs that are near ready. So when I go into those songwriting sessions, I’m gonna make sure that those people who are skeptical of me will know that I’m well prepared and that I know what I’m doing. 

[00:09:55] Joe: It’s like I’m thinking about Sun Sue and the Art of War. Right. The best battle’s, the one that’s never fought, like even at 13 and 14.

She’s thinking about the battles. Yeah. Ahead of her. You talk about her ability, her intelligence. And her drive. She’s going in to write songs at 13, 14 years old. Those early songs that she was prepared with, how good were they? Kevin, 

[00:10:14] Kevin: you know, Robert Orle has talked about this where he said, you know, at that point, one out of two songs were really good, but her development, she rapidly developed over one or two years where he said, by the time she was 14, 15 years old, you know, eight outta 10 were really, really good.

[00:10:31] Joe: Eight outta 10. Yeah. So this tells me, I mean, what does it tell me, Kevin, she’s a good listener. Like she takes advice, like, how do I develop my talent that quickly over that short of a timeframe? 

[00:10:45] Kevin: Yeah, it’s all those things and it’s, it’s hard work. I mean, she really worked at it, you know, every day after school.

She was songwriting, she was in co-writing sessions and she was working with great professionals and great co-writers, and she was learning a lot from them at the same time. But yeah, it just shows her her dedication, but also her talent. You can work hard over two years and, you know, you may develop a little bit, but will you develop that much?

I don’t know. It depends on your talent. And so Taylor had, and she’s always, she’s shown this throughout her entire career, she’s extremely talented, but I don’t think anyone outworks her. 

[00:11:18] Joe: She wasn’t afraid either at 13 or 14 to share her opinions. Kevin, with these, we’ll call ’em old men, even though I’m a 57-year-old guy.

[00:11:26] Kevin: Yeah. 

[00:11:27] Joe: But she’s telling them where she thinks that they’re wrong. Where other professionals maybe, you know, they maybe have a, I dunno if it’s a healthy amount of respect or too much respect for these people that she’s collaborating with. 

[00:11:37] Kevin: Yeah. I mean, I do this in my career sometimes too. Sometimes consensus can be good, right?

Collaboration can be good. But other times it’s, it’s good to be headstrong and to really fight for your ideas. And Taylor was in rooms again with songwriters who weren’t used to writing the way that she wanted to write. She was very clear. She wanted to write for an audience of her peers. So she’s writing those songs.

She was very careful to make sure that those songs and the way that she was singing her lyrics were appealable to young girls. And if you’re a 35, 40 5-year-old male songwriter in Nashville, that’s probably an audience you haven’t written for before. So she made sure when she was in those sessions where if she thought something was trite or if she thought something wouldn’t really appeal to her peers that she spoke up.

[00:12:27] Joe: Why even write songs in the first place? I mean, so many of the pop artists that are out there today don’t write their own music. Kevin, somebody else is writing the music. They choose the ones that they like and they go take ’em out and perform ’em. I mean, I. I even look at Prince over the years, wrote music for so many different people and a lot of people don’t even know Prince was behind this music.

[00:12:45] Kevin: Yeah, pop music. If you look at over time, the amount of songwriters on each song has increased. I don’t know the exact stat, but you know, there’s usually four or five songwriters to a song these days. Not a 

[00:12:57] Joe: single song. Yeah. On 

[00:12:58] Kevin: a single song. And I mean, there’s some that has 17 songwriters on it. It’s, it’s a hard business.

Hit making is a hard business and it takes a lot of people to, to make a hit. But with Taylor, it was a smart decision that she wanted to write her own songs and she really pushed to write her own songs because, especially for the market that she was going after these teenage girls, authenticity was key.

There had been other girls, teen girls and teen boys too that tried to make it in country music, but didn’t quite work. Right. Because they were singing songs that were beyond their maturity. But Taylor was singing songs as right in her sweet spot, and that’s why her audience were. Really receptive to what she was doing.

[00:13:38] Joe: It’s incredible. I think the analogy, ’cause I know for our average listener, it’s hard for them to go, Taylor Swift, what does this have to do with me? 

[00:13:45] Kevin: Yeah. 

[00:13:46] Joe: But I think a lot of this, Kevin is controlling your supply chain, right? Mm-hmm. I mean, understanding where the cracks are and really knowing exactly what it is that you’re selling 

[00:13:55] Kevin: Yes.

To the people that you’re selling to. Oh, that it’s, it’s so critical. It sounds so simple, right? But how many of us are, are really doing it right? How many brands can do this? It’s tough. And she’s shown this her entire career. She had such an innate sense of who she is and what her customer needs, her fans, and that’s a big part of her longevity.

’cause she’s adapted and evolved throughout the years, but she’s always kept that core sensibility. She really understands what her customers are hiring her to do, and that’s why they’ve stuck around for so long. 

[00:14:27] Joe: You have this quote from Taylor, I’d lie awake at night and think about the roaring crowds and coming out and the light hitting me for the first time.

And anybody’s wanna be on a stage. Kevin has thought that yes, but the second half of this that you write, she then said, but I was always very calculated about it. I would think exactly about how I was going to get there, not just how it would feel to be there. Yeah. Like she’s thinking about the steps along the way.

I, I’m just at 13, 14 years old. How the hell are you thinking about the North Star that much? Is this a musical family? Does she got a circle of people around her going, Taylor, you do this first, you do this second, you do this. Like, how do we learn from that? 

[00:15:09] Kevin: I wish I knew because I tell, I tell my kids how to do it.

Right. I have two young kids, of course, she had a great team around her. Her mother worked in marketing. Her father works at financial services. Her maternal grandmother was an opera singer. So she doesn’t come from a showbiz family, but I think because her grandmother was in the business, she, she probably understood how to navigate the industry a little bit better than other people did.

And then of course, I’m sure her parents played a huge role in sort of shaping how she thought about her career. 

[00:15:43] Joe: It’s funny because people could hear what you just said and they could go, oh, okay, well then I can’t do it ’cause I don’t have any of those things. Yeah, but you make a great point, which is, I.

Lead with your strengths, but you still gotta grab that strength. Like just because she has these, these advantages, we’ll call them Kevin. Oh yeah. Doesn’t mean she’s gonna take advantage of ’em. Oh no. Taylor really jumped in and took advantage 

[00:16:02] Kevin: of it. I mean, there’s plenty of people who’s rich parents who have good singing voices, who are singing at the farmer’s market, who aren’t Taylor Swift.

You know? It’s the fact that she seized an opportunity that other people were ignoring, and that was a teenage girl audience was huge. Because if she didn’t do that, and if she waited and said, oh, you know what? I’ll wait till I’m 18. Maybe I’ll sing some other people’s songs. I don’t think we’d be talking about Taylor Swift today.

I really don’t. Yes, luck plays a huge part in success, especially in a culture market like music. But the fact that she sees that opportunity and that other people were ignoring it is huge. That was a big reason why she broke through, because once she broke through, she didn’t have much competition. There weren’t other teen girls writing songs for the teenage girl market in country music.

So she was a category of one that played a huge impact on her early success. 

[00:16:55] Joe: You call this strategically blue ocean versus red ocean strategy. Can you explain that to our stackers that don’t know the difference between blue ocean strategy, red ocean strategy? 

[00:17:05] Kevin: Blue Ocean is a untapped market. It’s a market that other people are ignoring.

Like I mentioned, if you break into a market like that, then you’ve created a new category, right? So there’s far less competition in that category. A red ocean, the red means it’s cutthroat. There’s a lot of blood in that ocean, and it’s fierce competition. Most businesses, most companies, most brands are operating in that red ocean.

But if you can break into a blue ocean. The opportunities are vast. 

[00:17:34] Joe: Well, let’s talk about that because breaking into that blue ocean, as I heard you hesitate there, Kevin, I mean, that’s, that is the battle, right? I mean, let’s talk about some of the early challenges. Number one, radio. 

[00:17:46] Kevin: Yep. 

[00:17:47] Joe: 13, 14-year-old girl, 15, 16.

By the time she really gets rolling, writing for an audience, marketers and radio Kevin say this, there is no market there. There is no country music market at teenage girls. 

[00:17:58] Kevin: Yeah. And the data proved that there’s a lot of consolidation that was going on in the music industry. At the time, big conglomerates were coming up, coming in, buying local radio stations.

And so they’re, they’re using algorithmic playlists. And those playlists were dominated by men in Stetson hats and trucker caps. 80% of hits on country radio were performed by men, and men were played four to five times more than females on country radio. So if you looked at the data. It made sense how executive and country music were like, ah, you know what?

I don’t think there’s a market here, because that’s what the data said. 

[00:18:39] Joe: What’s going on in the Nashville music scene 

[00:18:40] Kevin: at that time? In what? In what? In what regards? In what respect? Well, I’m 

[00:18:44] Joe: thinking you’re talking about radio and consolidation, and you’ve got these people, but I know that there was also some consolidation going on in Nashville as well with the record companies.

[00:18:54] Kevin: Oh, the record companies. Yeah, for sure. The number of record labels at the time was shrinking, because around that time, remember, this was the post Napster age in the heyday of the music industry, which is in the late nineties, CD sales were huge, right? I mean, music labels were printing money, but then Napster and the internet came along and those sales plummeted.

So that’s why there is, there’s a lot of shrinkage in the number of music labels in Nashville. At the time, Nashville was struggling. The entire music industry was struggling around this time. 

[00:19:27] Joe: You’ve got these record label executives then running scared, afraid for their own jobs. So how are you gonna take a chance on this market that doesn’t exist according to all your research, radio doesn’t want to take a chance.

Swift, when she breaks out of her record deal, excuse me, her developmental deal, how does she start getting the word out first? Because she knows. She knows you, right Kevin? That she’s gonna need some help. How does she get the word out that she needs help and who she is in that type of a market that’s like she’s a salmon swimming upstream.

[00:20:02] Kevin: Yeah, so Taylor was well known in Nashville at this point because of her age. She had that development deal with RCA, but she was also signed to Sony at TV to a publishing deal. Now the publishing deal revolves around songwriting, right? So they really believed in her songwriting, so people knew who Taylor was.

And then when she left the development deal with RCA that that made news too. That’s some waves. That’s a bold move. She ended up having a showcase at the Bluebird Cafe. Now, the Bluebird Cafe is a historic haunt outside of Nashville. A lot of famous Nashville singer-songwriters were discovered there.

Garth Brooks Faith Hill. So she had a showcase and she had sent around a promotional package to all the major labels around Nashville. And one of the people who got her promotional package was Scott Beta, who we’d mentioned earlier. Scott Beta had worked with another teen star or someone who tried to be a teen star, was Jessica Andrews when he worked for Dreamworks.

And Scott BTA was one of the few people in Nashville who thought that a teen star could make it, because when they were trying to promote Jessica Andrews, they brought her to high schools across the state, and he saw that there was this grassroots fervor around her. The energy in the room was palpable.

Now, Jessica Andrews didn’t pan out, as most artists don’t, but he saw, he’s like, you know what? There is room for a teen girl in country music. So when he saw Swift Package, he was intrigued. He had Swift come to his office. He was working at Universal Labor Group at the time, and Swift played her songs and he was hooked.

And then two days later, he went to the Bluebird Cafe and saw her perform live and said, I wanna sign you to a record deal. 

[00:21:54] Joe: What’s funny is the difference you write between Andrews and Swift is some of the things that we already talked about. I mean, the fact that Swift wrote her own music and Andrews didn’t.

Yeah. Andrews music. It sounds like Kevin, I haven’t listened to much of Andrew’s music, but came off maybe as trite or emotions above her head where Taylors were spot on for, I guess, you know, quote unquote kid her age. 

[00:22:16] Kevin: And this is something Scott Beta has said about Jessica Andrews. He said that she didn’t quite have the vision to make it.

She wasn’t quite sure if she wanted to be a country artist or a pop star, where at the time Taylor was very squarely in the country lane. 

[00:22:32] Joe: What strikes me is I remember being on this fishing trip with my dad and one of his buddies, Kevin, and we’re headed up into Canada. 

[00:22:38] Kevin: Yeah. 

[00:22:39] Joe: And they popped this CD in at the time, at or around this time with Leanne Rhimes Lee Ann Rimes is another name that you mentioned of a young star that also struggled later on.

I remember hearing her sing that 50 forties or 50 song Blue. 

[00:22:54] Kevin: Yeah. 

[00:22:54] Joe: And this is a song that clearly is older than her age, and she’s singing this, um, completely retro song, so effing beautifully, just so 

[00:23:03] Kevin: Yeah, yeah, yeah. 

[00:23:04] Joe: Incredibly beautiful. So you could see that it was there, like the thirst. The thirst could be there almost in an Amy Winehouse kind of way.

[00:23:11] Kevin: And Leanne Rimes was, was huge. But I think executives thought that, well, it’s hard to find longevity when you’re singing those types of songs. And that’s what set Taylor apart. ’cause Taylor wasn’t one of these polished teenagers, these show biz teenagers. She was very much a teenager. If you look back at videos of her around the time, she has chaotic teenage girl energy and you can feel it in her songs too.

So her songs were very authentic to the teenage experience, but at the same time, they had a tinge of nostalgia to them too, where older fans, country music fans could still listen to those songs and remember their their own past loves and missed chances too. 

[00:23:53] Joe: I’ve got a couple more themes I wanna talk about before we let you go.

The next one is specifically this collaboration with with bta. 

[00:24:03] TikTok: Yeah. He 

[00:24:04] Joe: clearly gets her where nobody else in Nashville really gets her. He believes in her. He doesn’t want her to sing anybody else’s songs. He makes that clear. Wants her to sing her songs, which is definitely what she wants to do. Control her supply chain, be able to stand behind her lyrics, be authentic.

All the things that you mentioned earlier. Rashta though tells her that he’s not staying around Universal, like he’s gonna go do his own thing. 

[00:24:29] Kevin: Yeah. I 

[00:24:29] Joe: can’t imagine Kevin, if, if you believed in me and Stacky Benjamins, and then at the end of that conversation I’m like, Kevin totally gets me. And then dude, you go, but I’m leaving the company and I’m gonna create this thing and I’m not sure if I’m gonna have funding, but hey, you gotta wait for me.

[00:24:47] Kevin: Yeah. 

[00:24:48] Joe: Like this is a ballsy move for a girl who’s 15, 16 years old. Where’s the business lesson there, I guess, uh, for all of us. 

[00:24:57] Kevin: Business lesson for me is Scott Beta had much more skin in the game than an executive at a major label. They had a tall hill to climb. They had the get through country music radio.

There was no way you could be successful in country music at the time without being played on country radio. So she needed a guy who could hustle, a promotions guy, who could really convince people on her behalf that she needed to be played on country radio. 

[00:25:28] Joe: Oh, I, she aligned herself with somebody with as much at stake as she had at stake for 

[00:25:32] Kevin: sure.

And Scott did have to hustle because the success of his label, big Machine was largely contingent on the success of Taylor Swift because he had so much skin in the game. She ended up making the right decision. ’cause we all know if she went to a major label, that executive would have to fight internally with people.

He’d have to fight with the promotions people about, he’d have to try to convince people at every turn that this is the girl that this should be promoting. This is the girl that is gonna find success in country music. But since Versetta was all by himself and had his own label and was really dependent on Swift’s success, he was much more willing to hustle on her behalf.

[00:26:14] Joe: You write that the founder of Y Combinator wrote that there’s, there’s no market for ideas. I mean, everything we’ve talked about so far, Kevin is this extremely energetic, focused, willful, intelligent, able, driven, young woman. A guy who’s hustling, but all this is kind of nebulous. Yep. Now we actually gotta do the hard part, which is connect with the audience.

While Taylor Swift has some music connections, she’s not somebody like, uh, Miley Cyrus, who, you know, came out of a, came out of a Disney channel, came outta 

[00:26:49] Kevin: Disney, right? Yeah, 

[00:26:50] Joe: yeah. So she doesn’t have that. How does she do the hard work of convincing these radio stations and these record executives, she and Scott alone, how do they, how do they turn that hustle into magic?

To begin creating who we see today in Taylor Swift, 

[00:27:05] Kevin: they had to use underdog strategies. Luckily, at the time, MySpace was very popular. This is 2006. MySpace is the biggest social media platform there is. 

[00:27:16] Joe: I’m still friends with that one guy from MySpace. 

[00:27:19] Kevin: Are you, is it Tom? Is that his name? Tom, I believe.

Yeah. Tom Tom’s still around. Yeah. Yeah. So they, they went to MySpace. Taylor had a, a decent following on MySpace. It wasn’t huge, but she had enough of a following on MySpace where she could ask her followers to contact. Their local stations and say, Hey, please play Taylor Swift songs. Please play Taylor Swift songs.

And it 

[00:27:43] Joe: worked. It’s, it’s like surrounding these record executives. 

[00:27:46] Kevin: Yes, exactly. That’s exactly what they did. Once he was played on country music radio, they sent Taylor on a six month tour to all the radio stations. 

[00:27:56] Joe: Oh man. 

[00:27:57] Kevin: She’s pretty charming. She was wise beyond her years. And I remember her de facto manager at the time wrote back to his, the rest of the team at Big Machine and said, Hey, if you’re ever on one of these events with her, one of these radio tours, just set her up and leave her alone.

That’s all you need to do, because she’ll do the rest of the work. And that’s what she did. She won a six month tour. 

[00:28:22] Joe: She knows what she’s selling. She does. I mean, she knows a hundred percent 

[00:28:24] Kevin: what 

[00:28:24] Joe: she’s 

[00:28:24] Kevin: selling completely. And I, anyone who’s interested, you should go on YouTube and try to find videos of Taylor Swift in 2006.

It’s amazing to see because she is a great salesman. 

[00:28:35] Joe: There’s also a business lesson there, I think, Kevin, in letting your employees go. Like when you see your employees go, how many times do we all get killed by a micromanager? 

[00:28:43] Kevin: Right? Oh, for sure. Yeah. Or media tra like too much media training. You know, it’s right.

They could have set her up and said, you know what, Taylor like, let’s act like you’re 25, 30 years old. Like, no. I mean she was, she was very smart. She knew how to sell her product, but she was also very her at the same time. You know, she was very authentic to who she is. She’s goofy. She had that theater kid energy, which is really unique to who she is, and she played up those qualities.

She didn’t try to hide them. 

[00:29:11] Joe: Last thing I wanna talk about is positioning, because when you’re first breaking into a market, I think positioning is incredibly important. Yeah. She has all these different songs to choose from. As her first song and, and you write that getting that single right is gonna be a huge, huge part of her successor failure.

And both Scott and Taylor know this. How did they choose her first single? 

[00:29:32] Kevin: So they ended up going with a song named Tim McGraw, which is a very clever title. It’s the perfect mix of, and by 

[00:29:39] Joe: the way, for people that don’t know, Tim McGraw is a current country singer. 

[00:29:42] Kevin: Yes. 

[00:29:43] Joe: Right then. Yes. So, so they pick a single that people are gonna go, Tim McGraw.

Wait, that Tim McGraw, 

[00:29:48] Kevin: yes, it makes sense in terms of the song, but as a marketing technique, it makes a lot of sense too, because it catches people’s attention. That song was a perfect mix of traditional country, but had enough novelty to it to stand out because the big goal here, they had to convince the gatekeepers of country music radio.

Right. So they couldn’t do something that was too teen focused. That was too swiftian, I would say. You know, that had too much novelty. So Tim McGraw is a very nostalgic song. It sounds like a classic country song about a boy who goes off to college, but it sounds like a, like I mentioned, it sounds like a traditional country song.

So it was enough, it was familiar enough so the gatekeepers of country music weren’t turned off by it, but again, was novel enough to catch people’s attention, especially the name of that song, Tim McGraw. 

[00:30:41] Joe: What’s interesting about that to me, Kevin, is I was thinking through this. Is that, you know, she’s trying to use this blue ocean strategy, which means she has to surprise and delight a lot of new people.

Yeah. But she has to convince the person at the record company, she’s gotta convince the people, the radio people. She’s got so many people to convince, like to begin with something that is familiar to them before you try to take the I, I can just imagine if, you know, one of her later hits if she tried, start with some of the stuff she writes now.

She would’ve lost them immediately. Oh. Without doubt. Like, you’ve kidding me? 

[00:31:15] Kevin: This isn’t country music. For sure. And that’s why it was such a wise decision. And she had other songs on that album that she could’ve led with that sound more like the current. Taylor Swift and Tim McGraw has elements of the current Taylor Swift, don’t get me wrong, but it was the most familiar song that she could have promoted to country radio at the time.

[00:31:35] Joe: Well, stackers, this is just the beginning. Like you guys know how much I absolutely love case analysis, but a case analysis that takes somebody who’s way. Way over here, like something we don’t think about often when we’re thinking about business lessons. And Kevin, you, you bring it to bear. The book is called, there’s nothing like this, the Strategic Genius of Taylor Swift, and it was available everywhere last week, right?

[00:31:57] Kevin: Yeah, for sure. April 8th. 

[00:31:59] Joe: Thank you so much for, for mentoring our stackers. I think, I think what, maybe I end with one more question, which is, you know, all this starts with Tim McGraw, right? Well, as we know it started way before Tim McGraw, but kind of her splashes with Tim McGraw. Did she ever reach out to Tim McGraw?

[00:32:15] Kevin: Yeah, Tim McGraw was doing an interview for a local radio station, and Taylor called in and they talked to each other about the song. 

[00:32:25] Joe: I love how you end that story in the book, by the way, where she’s like, Hey, you ever think about having an opening act? 

[00:32:31] Kevin: Yeah, for sure. She made the best of the opportunity, right?

She didn’t just wax poetic and, you know, rub elbows with Tim McGraw. At the end of it, she said, Hey, you know what, uh, this is, I’d love to open for you on tour. And she did. She ended up opening up for him too. Yeah, she, she 

[00:32:45] Joe: did. I didn’t know that. 

[00:32:47] Kevin: Yeah. 

[00:32:47] Joe: I felt like, uh, Glen, Gary, Glen Ross there. For people that don’t know, you don’t always be selling.

[00:32:51] Kevin: Yeah, always. Taylor’s always selling. She’s always selling. For sure.

[00:32:59] Doug: Hey there stackers. I’m Joe’s mom’s neighbor, Duggan. Okay. Huge misunderstanding. It’s where your pajamas to workday and happy you’re late. Filing your taxes day while I’m too busy celebrating to just yet file my taxes. I did just come down here in my pajamas. Check it out guys. Whoa. Hey. 

[00:33:20] Joe: No, you’re naked.

[00:33:22] Doug: But yeah, that’s the thing. I don’t wear pajamas. This is how I sleep. Somebody 

[00:33:27] OG: let a gorilla loosen here. That’s a lot of body hair. 

[00:33:30] Doug: Thank you. Hey, look, I got trivia to do, so let’s be professional guys. Today is the day when hopefully you filed an extension and are now relaxing from all of that stress of worrying about the taxes you never truly intended to file by yesterday.

But here’s today’s question. What day for those of us filing as individuals our taxes? Now do, I’ll be back right after I go Look this up, man. I love having to do trivia for this stuff. I learned so much. Whoops. Dropped my pen. Whoa, whoa. No, no, no, 

[00:34:03] OG: no, no. Gross.

[00:34:12] Doug: Hey there, stackers. I’m guy now wearing jeans and guy who apparently has to apologize to Joe’s mom. Joe’s mom’s neighbor, Doug. Well, maybe Sunday I’ll get to celebrate a full day of wearing pajamas to Workday, but not this year. But in worse news, I have the answer to today’s trivia question. If you decided not to file your taxes by yesterday, what day are they now due?

Assuming you filed an extension? Well, apparently I messed this up because all taxes were still due yesterday. If you also misunderstood how this thing works, you wanna get ’em paid ASAP because the IRS isn’t joking with the penalties and interest for failure to pay. But if you filed an extension, there is some good news while the money was already due.

The paperwork doesn’t have to be sent in until October 15th if you’re filing as an individual, not as a company, which may have completely different dates and rules. Got it. Hope so. Time for me to go call in a payment to the IRS. So, uh, I’m gonna send you back to Joe and OG 

[00:35:18] Joe: and OG Doug’s, right? Those failure to pay penalties, uh, fairly, fairly big.

What if, what if somebody doesn’t have the money? Do you like the payment plan system that the IRS has straight to 

[00:35:28] OG: jail? 

[00:35:29] Joe: Go to. Just, just turn yourself in. Turn yourself in. Can you imagine somebody walking in? I owed $18. Uh, you should just take me, 

[00:35:38] OG: I mean, you need to know what the penalties are and evaluate that against other options that are not also great, like credit cards and that sort of thing.

[00:35:48] Joe: Yeah, 

[00:35:48] OG: the underpayment penalty is as much as 25%. Interest is kind of the going rate of whatever the interest rates are. Probably right now, my guess is probably eight or 10% on 

[00:36:01] Joe: top of that. 

[00:36:03] OG: Yeah. Penalty. And so if you’re going, you know, I’ll just let the IRS come at me. They will eventually and they’ll be relatively polite with it, but, um, but it’s getting the meter runs and it goes in a hurry.

So if you have another place, take it from that other place. 

[00:36:19] Doug: Yeah. Og I’ve got another question for you. Um, you know, it’s not, not for me, but a friend of mine asking for a friend Sure, yeah. Asking for a friend. A friend of mine is wondering like, how do I know how much to pay? I mean, I didn’t do the paperwork to note, like I didn’t do the math to figure out what I owe, but I still have to pay on that date, even though I can file the paperwork in October.

Like, how am I, I, I mean, how are they supposed to know how much to pay? 

[00:36:42] OG: Yeah. Well, you just have to know I. So you, you, 

[00:36:47] Joe: oh, thanks. 

[00:36:48] OG: So 

[00:36:48] Joe: helpful. It sounds like a Nate per gaze answer. Nobody knows. Nobody knows. Yeah, 

[00:36:52] OG: nobody knows. It’s, uh, you have to round up, I mean, if you seriously don’t know, you, you, I’m guessing you probably have a ballpark idea.

Do you owe five grand or do you owe 50? You know, like you have a general sense of where you are in that process, and if you don’t round up, you have to overpay. If you underpay, then all of those penalties start applying. Even if you’re like, but I didn’t know, you know, that’s not an excuse. You’re, the payment is due April 15th.

The paperwork can be due October 15th. So. Off you go young man. I mean young man’s friend.

[00:37:27] Joe: Time for our TikTok minute. Speaking of, uh, reliable facts and getting reliable facts, this is the part of the show where we shine a light on a TikTok or who might be providing reliable facts or maybe not providing reliable facts. And before I have you guys, uh, answer whether you think this is brilliant or air quotes brilliant, I’ll tell you this comes from a guy we haven’t gone to in a while.

This comes from the Grant Cardone of, uh, Cardone Real Estate. 

[00:37:53] OG: Oh, I think it’s Sarone. It’s a silent, it’s a, it’s a soft 

[00:37:55] Joe: ass. So og you think, uh, Cardone is bringing it today, or 

[00:38:00] OG: air quotes bringing it? Absolutely. I’ve seen his airplane. This dude is nothing, if not, uh, bringing it, bringing it. 

[00:38:07] Doug: Yeah. Doug, how about you?

Well, if it’s Grant Sarone, then I don’t buy any of it,

[00:38:17] OG: but maybe 

[00:38:17] Joe: fairly certain. It’s Cardone in this case. Okay. It’s like a spoof account for Grant Cardone. Oh, this sadly is no spoof. ’cause here’s Grant Cardone in the middle of an interview of you. 

[00:38:27] TikTok: I have a lot of money in my 401k. Okay. I’m sorry for you. Why do you feel sorry For me? It’s a way to put money in without paying taxes on it.

It’s a way for you to be trapped for 30 years. Well, you could pull it out when you’re 63. How old are you right now? 50, 13 years from now, will taxes be higher or lower? Higher. You will wish you would’ve sold them when you were 50 ’cause you’d pay lower taxes. Dude, you don’t pay any taxes when you pull out money outta your 401k.

If you wait until you’re 63, when you start using that money, you’re gonna pay taxes. Okay? That’s just wrong. You weren’t charged taxes while it sat there. What’s wrong with you? You’re not. IRS allows penalty free withdrawals from retirement accounts after the age of 59 and a half. Penalty free. Not tax free.

So they’re gonna charge you a penalty. They’re gonna put handcuffs on you to sell it before then. But dude, when you’re 63 years old, when you start withdrawing, you’re gonna start paying taxes at that point. Oh, you’re right. 401k withdrawals are taxing. Exactly. I have a, oh boy. 

[00:39:13] Joe: I feel like we have two idiots sitting across.

It says right 

[00:39:15] OG: here, penalty free. 

[00:39:17] Joe: Both people in that discussion have no idea what the hell’s going on with a 401k. The interviewer has no idea. Grant Cardone throws out og age 63. Age 63. I didn’t know that age 63 was a thing anywhere. Well, I 

[00:39:29] OG: think he said 63 because of the guy who said at 63 he’s gonna retire.

I mean, he’s not wrong. I think when it comes to investing. People think that there’s only one right way to do it, and everyone else’s way is wrong. It’s like, and you see different people be successful in different areas and you go, well, that guy is the exception to the rule. The only way that can be really successful is my way.

And we all know people who are wildly successful by investing in public markets, by investing in their 401k by, you know, have tons of money by investing in equities. We both know tons of people who are wildly successful by owning real estate rental properties. We know people who are wildly successful owning commercial properties.

We know people who wildly successful have none of those things, but own a business and cash flow their life like that. There’s, you know, grant Cardone is really good at what he does. He’s also really good at selling the idea of what he does, which I think is probably more successful than other stuff. I guess true 

[00:40:27] Joe: genius right there.

[00:40:28] OG: But him to say, oh, well, that, that, that, that’s ridiculous. I mean, that’s no different than me saying buying real. I, I don’t particularly like buying real estate. To me it doesn’t, you know, some people love the idea of like being able to drive by and go like, that’s mine. And I, can you, can you see it? Let’s go touch it.

I don’t like that. There’s too much baggage with that in my, in my opinion, he looks at the way that he does it as this is a no brainer, right? This is easy. And then he looks at the other side and says, that’s really stupid. You can’t touch it. You know? And I think, look, there’s, that’s actually the win that you can’t touch it.

Yeah, technically. And so he’s not wrong. You will pay taxes in your 401k, assuming that it’s a pre-tax, 401k and not a Roth. But guess what else? You pay taxes on dividends from your real estate portfolio. Freaking income that you gain from your real estate portfolio. Here’s one that nobody knows about recapture depreciation when you sell your real estate portfolio, because the really cool thing about about real estate is you get to depreciate it.

Offset it against your income. Well, only if you’re an active investor, not if you’re passive, if you’re like the most people around. You’re passive, but let’s set that aside. So let’s say you get this big depreciation, then you sell your property, guess what? That depreciation number goes back on your taxes that you haven’t earned yet.

If you haven’t owned it for 37 or 27 years, it goes back on your taxes as ordinary income. So guess what? You get taxed on real estate too. You know, you get taxed on the gain, the government gets their pound of flesh and it seems more recently, two or three pounds of flesh as we were on April 

[00:41:57] Joe: 15th. Well, and that’s what frustrates me about this is not that real estate can’t be a great way to go.

It’s in poo-pooing the other, the other avenues. Yeah. I mean that are, that are out there going, oh, that’s a trap. You, 

[00:42:07] OG: you do you like if you’re, you know, where it works really well for people that are really good at it. Like I have a good friend of mine, he’s a realtor. Every time he brings me an idea, he goes, Hey, I know you’re probably not into it, but I got this deal.

I need 50 grand. Here’s what we’re doing. I go, yeah, man, here. Because I know he knows it. If he says it’s good, I trust him implicitly. I wouldn’t go out and try to find the deal to like flip the house and, you know, I don’t know anything about that crap, but he does. And so I’m like, yeah, man, here, here, take some cash, bro.

Make it happen. That’s my son, you know? Yeah. Same thing with Nick, right? Like if I needed to buy a house in Detroit, I, I would, I, you better recall Nick, like he would know what to do. He has the contacts, he’s built that network, he’s built those relationships, you know, so. Greg Cardone’s a good dude, but he likes to the piece, the fire a little bit 

[00:42:57] Joe: piece.

He totally does. The piece that I really want to focus on that you said is that every investment has an Achilles heel. No, there is no investment that doesn’t have an Achilles heel. He’s pointing out what he thinks the Achilles heel is of the 401k, to your point, there’s four. Oh, there’s an Achilles heel in real estate.

If you think you have the investment with no Achilles heel, you have not looked hard enough. You have to keep looking because you have to know what that downside is. 

[00:43:22] OG: Yeah. Everything has a downside. Everything has a equal and opposite reaction. I don’t know. That sounds stupid. 

[00:43:27] Joe: Wow. Getting all scientific on us.

No, I just made that up. Let’s do a headline. How about that? 

[00:43:32] headlines: Hello Darlings. And now it’s time for your favorite part of the show, our Stacking Benjamin’s headlines. 

[00:43:38] Joe: This comes to us from, uh, CNBC. I found this last week, guys, Trevor Lawrence, uh, Joaquin wrote this. 

[00:43:44] OG: Nobody was on CNBC last week, 

[00:43:47] Joe: believe it or not.

I saw something unrelated to tariffs and I’m like, please God, let’s talk about it. Like that would be great. Took it 20 minutes to dig for it, but you found one. It did. If I could not talk about tariffs for three minutes, that would be fantastic. Trevor writes, whether to buy cryptocurrency is a long-term.

Holding may be the biggest decision an investor interest in digital assets has to make. But where to store crypto like Bitcoin. Well, that can become more consequential. The most consequential. He writes, I. Following the wildfires earlier this year in California, social media posts began to appear with claims of Bitcoin losses with some users showing metal plates intended to protect seed phrases burnt up, and a legible or describing the complexity of recovering crypto keys stored in a safety deposit box in a bank impacted by the fires.

These people og, like what’s called a cold storage solution. Cold storage is where you take your Bitcoin, you put it on a little device like this one in my hand for people, 

[00:44:54] Doug: it’s a USB memory drive. You sick os get your mind out the gutter. 

[00:44:59] Joe: I don’t even know where it would be in the gutter, but anyway, all you said was device in my hand.

So that, can you take, and you put, well keep those jeans on, Doug. You put it here. And then supposedly it’s safer here than it is in the hot wallet as it as it were. Hot wallet sounds to me like you may need to go see a doctor. 

[00:45:21] OG: I mean, I’ve heard of prison wallet, but that’s a different thing altogether.

[00:45:25] Joe: Holders of crypto typically use some form of what can be called a wallet, and there are a few main features, whether that wallet’s connected to the internet and how much control is directly embedded in the wallet for trades and transfers. There’s also the underlying issue of whether a crypto investor uses a third party for custody at all, or maintains total custody and trading control over their holdings.

Now they’re pointing out OG that you know, while there might be safety, not having your money in a spot where over the years you and I have reported on these institutions that might be a little nefarious and all of a sudden your money with them just disappears because Pirates got it. My bad. And you don’t have that.

That doesn’t mean that keeping it on this little. Storage device doesn’t have its own issues. 

[00:46:10] OG: I mean, you lose your keys, right? You like lose your, like lose where you put your wallet. You have to air tag your kids sometimes to not lose them. Like how many, well how many times have you found a $20 bill in a coat pocket from 15 years ago?

You know? I mean, 

[00:46:27] Joe: yeah. I was literally just getting ready to take a coat to Goodwill last week, and there was a hundred, a hundred dollars bill in the pocket that has probably been there for 10 years. I have no idea when I came across Thunder Box. So inflation, 

[00:46:41] OG: it’s like a, it’s like a $70 bill. 

[00:46:44] Joe: I, I know. I had no, I had, I, I had to.

Well, for me, Doug, especially, how much money, 

[00:46:49] OG: how much, you know how rich I am. I can have a hundred dollar bills and post because I’ve got a record 

[00:46:53] Joe: over and over saying that if I’ve got 10 bucks in my pocket, I’m spending it right now. Like that is So what did you buy the key to my success. Oh, a board game.

Of course. Yeah. Yeah. Inflation is eating that alive. Oj I got 

[00:47:04] OG: a couple of gift cards. Yeah, there was a tech service that I started using and then I referred somebody to it also, and so they sent me like a thank you gift card, but I thought it was gonna come as like a gift card. Gift card, and it was a digital one.

I’m like, ah, crap. Like whatcha? You can do a digital thing and then it’s like, put it on your Apple wallet. And I was like, oh, okay, whatever. And so that became like the default Apple Wallet. It was a $600 gift card. Oh God. So that, that’s $600. And I’m like, every time I’m like, wow, this doesn’t even count on the budget.

Like of course we’re going to Jimmy John’s today. Everybody, you know, it’s like, and it comes up with this weird, you know, it’s just a weird gift card thing. Yeah. It’s not like literally tag. I feel so free right now with cash. ’cause I’m like, who cares? Like golf, Jimmy, everybodys, of course we’re getting Pro V one X’s right now.

Why wouldn’t we $4 a golf ball? Who cares? You’re gonna launch ’em into the like, it’s like free money. So you found free money a hundred dollars. 

[00:47:59] Joe: But let’s expand this argument because I know a lot of our audience doesn’t own any crypto and this might not be a big deal for them. This is a big deal though.

OG storing stuff yourself. I mean, the number of times I came across clients that had. Gold in their house. They had cash in their house, they had, uh, just, just there, there’s so many opportunities to just get ripped off and especially, especially we hear seniors doing this and a relative gets wind of it and next thing you know, seniors get robbed by people in hoods that look a heck of a lot like Cousin Larry.

[00:48:36] OG: I don’t know that that happens a ton, but there’s risk for all these things. I feel the most comfortable with money in the bank. I feel the most comfortable with, you know, investments in my Schwab account. Could there be something that goes wrong somewhere in there? Yes. But I feel like that is the, the, the safest place for all of those things.

And when you start talking about stuff that’s around the house, you know, we’ve got cash at home. I think you guys have some cash at home in a drawer or something, you know, it’s helps to have a few bucks, but when you have valuables in other places. What, what could go wrong with that? Right. If you have people at your home, Joe, you, you know, you’ve talked about on the show you had a house break in and you largely suspected it might’ve been due to the fact that there was somebody that was in your house doing some maintenance and maybe it was kind of tied to that and a friend of a friend and, you know, whatever.

You just have to be aware, I think of, of not only your surroundings, but what information you, you know, you have. I had this guy that came to the door one time and I work from home. I’m home every day. My office faces the front door. So like when the UPS guy shows up, I get the package right away and I say hi every day.

That’s just like kind of my way of going, like, yep, I’m here. Yep. I’m still here. Yep. I’m still here. You know, and this guy came to the door one time and was, I dunno, soliciting, you know, roof repair or something and he goes, no dogs in the house. And that was the weirdest thing. Wow. Yeah. To have somebody say to me and I, and I just kind of looked at him and I go.

Of course there are dogs in the house who doesn’t have dogs. We just put ’em in the back during the day so they don’t bark when I’m on calls. Why? What kind of dogs do you have? He goes, oh, I’m just kind of curious. I was just like, uh, whatever you’re selling, I definitely don’t want now. Right. And we are gonna have a neighborhood watch meeting.

It just was a weird thing. Somebody else might have taken that a completely different way. Right? Like. Oh no, we have cats. You know, it’s like, 

[00:50:35] Doug: oh, good. Actually I have two Dobermans and I, and, and as effective, I couldn’t 

[00:50:39] OG: think fast enough to like think of like a scary, I was like, I wanted to be like, yeah, the big one with the teeth and growls, but I’m not a dog guy, so I couldn’t think, I didn’t wanna be like, yeah, we have a German bulldog.

And like, have that be like, like the one little teeny one. I didn’t know enough about dogs to say what kind. I’ve got a dash and that’s a big one, right? It’s a dashing. I was like, I got one of those wiener dogs. They’re like Y all the time. Like, get your ankles. I don’t know, man. I, I, 

[00:51:04] Doug: cats are terrifying. You just don’t know what they’re gonna do.

And they got the claws and uh, and I don’t know, I get two Dobermans and I think I might need to add a cat into the mix just to, 

[00:51:13] OG: I was telling you, Doug, that, uh, my neighbor who moved in a couple doors down, new guy, he has what I can only assume is, or, you know, was a former police bomb dog or you know, like military.

Trained. Wow. Professional dog. This thing is like a horse and it looks so scary. I’m like, huh? The guy with the dog, you know? And I’m sure it’s like the most lovable thing and like only responds in like Portuguese language or something. ’cause they do that, you know? So that, you know, you can’t, 

[00:51:43] Doug: Portuguese, that’s the language.

[00:51:45] OG: Well it’s German. I know generally, but you know what I mean. Like, they train ’em in different languages, so you can’t say like, stop, you know? Right. It doesn’t know what that you have to, you know, or whatever. I dunno, like, but, uh, yeah, maybe I should get like a picture of one of those, or just ask him the name of it.

Like, what’s the name of your dog? He’ll be like, oh, it’s like Charlie. Be like, no, no, no. Like what’s the, what do I sell? What do I tell people that I have so that they get scared? 

[00:52:08] Joe: The reason I brought up, 

[00:52:10] OG: I don’t know how we got to that. That’s just story hour with og. Just, it was fun. Just, uh, well, 

[00:52:15] Joe: no, no. The fact that people are fishing for information, right?

No dogs in the house. Like these people that are, that come one way. I wanted to just stop for a second because you said, you know, I don’t know how often it’s the cousin Larry thing, but I’m looking at the a RP website right now. Most, of course, you are most scams against older adults. It comes up automatically when 

[00:52:33] Doug: he starts his browser.

I know most scams against home Joe, 

[00:52:37] Joe: older adults are perpetrated by people They know. It is, it is usually people that know what’s going on inside that senior’s house that is doing the bad stuff. 

[00:52:49] OG: Tell me the things that are top of Joe’s mind right now. That’s what I wanna know. Oh, we don’t have to guess.

We know A-A-A-R-P law Break-Ins, you know, are top of, top of Joe’s mind. Sorry, you’re worried about cousin Larry. All of a sudden. The other thing that I want to just wanna bring to your attention as it relates to stuff around the house, right? We talk about insurance and documenting, you know, making sure that the numbers are correct and the replacement value versus residual value and like knowing the difference of all those things.

But I think you also need to know the limitations of what your policy has. If you’re one of these people that likes to have a lot of cash at home, you know, you got a couple thousand bucks in the drawer in the safe or something like that, you better know what your insurance is gonna cover. Because a lot of times they might say, well, we only cover $2,000 worth of cash at home.

We only cover $10,000 worth of jewelry, not documented. You know, like you’d need to go through and, and so if you’ve been married a long time and you give your spouse you know, nice things from time to time and you just go, well, it’s insured, is it? Do you have $20,000 worth of jewelry at home, but they only cover five unless you specifically spell out the items that are there.

Firearms are another big one because there’s a lot of anxiety about reporting firearms, you know, and what, what people own or don’t own. Perhaps what maybe has fallen into the lake on a fishing trip. But if you have that at your home, they’re not inexpensive. You need to make sure that your policy accounts for it.

I mean, these are all things that I think are important to recognize. Like where, where your exposure is when you make a decision around a specific thing. I wanna have lots of cash at home ’cause it makes me feel safe. Great, but what if the house burns down? What? What happens? You know? Or if there’s a break in what happens?

You’ve talked about that, Joe, about documenting serial numbers for your stuff. Not because you’re gonna get it back necessarily, but because it becomes easier for the insurance company to say, oh, you had the model number, whatever, whatever from Samsung. So that’s this tv. Let’s get you new one. 

[00:54:51] Joe: Yeah, you really around your birthday is a great date.

Uh, look at your policy. Make sure the policy’s up to date. Happy birthday. Let’s read insurance statements. It’s also a good opportunity to just compare pricing what insurance agent told me several years ago, and it has always been true that you might do nothing different and your policy cost goes up just because you’re not in the target market for that insurance company anymore.

Yeah. So you might fall away. I love this idea about thinking about your stuff and where you keep it. I mean, the fact that you might have a fireproof safe, a lot of people in the fires did and their device still melted that had their 

[00:55:23] OG: Yeah. Their, their, I buy cold storage. 

[00:55:26] Joe: Yeah. Had their things on it. Of course, this, this piece also says even when you’re using a third party custodial option, like a Charles Schwab as an example for your, your stocks or a Fidelity or vanguard or something with your crypto.

There are steps to help you remain vigilant against the threat POed by cyber criminals. The use of two factor authentication is important. Strong passwords. The US Marshal Service within Department of Justice, which is responsible for asset forfeiture from law enforcement, uses Coinbase Prime to provide custody for its seized digital assets.

Lots of interesting stuff here. I will link to it for people that have crypto in our show [email protected] and, uh, you can dive in even more to the risks of however you store your stuff. There’s a risk no matter what time for us to mosey out on the back porch and see what’s going on. Doug, what, uh, what do we got on the back porch today, man?

[00:56:23] Doug: Joe, I don’t have a lot for the back porch today, but I did need to talk to you about all these books stacked up all over the place. We can’t even move down here. 

[00:56:30] Joe: I know, right. And we now have another one, the amazing Kevin Evers book. I’m gonna be, I’m, I’m now done with this amazing work, so we gotta give away some more books.

And we do that in exchange for, it’s not really an exchange if you do a review. We’ve had some fantastic reviews lately, so thank you so much. But if you leave us a review wherever you leave it, please send me a note that you left it. Show me that you left it. And you know what? I will give you a choice of five different books.

I’ve had people think that, uh, they can just request the book and I may have given it away already. So, uh, well, I can’t give you a choice. I, I can’t give you a specific book. I can give you a choice of books. And the cool thing is we just hired a couple of interns from Texas a and m, Texarkana, wanna say a big shout out to Denny, who’s a senior at Texas a and m, and to Cree, who is a sophomore.

And these ladies are doing a great job, but that also makes it easier for me to head to the post office. By the way, I may, because of all my travel schedule, may have promised you a book in the past and it may not have gone out. Write me again, please. Just write me again and I will go back and we’ll make sure that that is, that is right.

I actually had a guy tell me that on my book tour. Three years ago in Atlanta, I told him that I would give him a T-shirt and I, and he saw me in economy and he goes, Hey, I got a boat to pick with Joe. And he was kidding. And it was all smiles and it was very nice. But Matt, Matt’s t-shirt now is on the way.

Three years later we’re actually giving him some more swag for, uh, interest on his, on his money. But Joe, you 

[00:58:02] Doug: still owe me 500 bucks by the way. I dunno if you remember. And that’s 

[00:58:05] Joe: from 20 years ago at 8% interest. Right? We do have a lot of books, so, uh, write me [email protected] and let me know if you left her.

So review someplace and uh, happy to make sure that we send an intern to the post office ’cause they’re making my life a lot easier lately. All right, that is all we have today. Huge thanks to Kevin Evers. I know Doug, you’re gonna thank him again in just a second. But I love these mentors. I love the fact we got to do the deep dive into Taylor Swift.

On Friday, we pivot slightly three CFPs on our round table. The retirement answer, man. Roger Whitney, Alyssa Maes from South Florida. A great CFP down there and the OG all talking about your eras, right? We’re gonna tour your eras, the early career that you had or have, or looking at what’s important to get right with your money.

What should you be defensive about? Early on, Taylor Swift’s focus has changed throughout her career and yours should too. So in your thirties and forties, how should it change? And then as you near retirement and are in retirement, what are the important things? We’re gonna dive into your portfolio using Taylor Swift as a theme since we’ve done that all week.

And then next week we’re gonna get tactical. We were all strategy. Right now we’re gonna dive into tactics. Lorraine Lee is gonna join us and all week long we’re diving into the tactics of, uh, your career brand. What, what I love, and Doug, you and I were laughing about this earlier. So many of us, me included, by the way, when I first heard about this roll their eyes about career branding.

Oh God, no. Career brand. Lorraine’s retort. And this is why I wanted her on Lorraine’s retort, was, yeah, you already have one. It probably sucks, right? Whether you want one or not. If you don’t know what it is, it’s 

[00:59:51] Doug: bad. 

[00:59:52] Joe: Yeah. So we’re gonna help you, uh, with your career branding tactics. Next week we go from strategy to tactics.

That’s gonna be fun. Alright. Enough foreshadowing, Doug. Lots of takeaways. What are the big three today? 

[01:00:03] Doug: Well, Joe first take some advice from Kevin Evers surrounding yourself with people who are as motivated as you and have as much at stake. That’s a great part of your recipe. Assuming you know what it’ll take to win second cold storage for your crypto, that has risk too.

So form a plan against losing access to your hard earned money. But the big lesson, good news, after talking to the IRS, they said I don’t have to pay anything because apparently this job doesn’t come with any, uh, what they call. Income. So I mean, you’ve all heard of tax free. OG said This is better because the job is income free and we’re nipping this tax thing right in the bud.

Brilliant og. That guy just continues to prove he’s the brains of this operation. Thanks to Kevin Evers from Harvard Business Review for joining us today. You’ll find his deep work into the strategic creative genius of Taylor Swift titled There’s Nothing Like This Wherever you Buy books. We’ll also include links in our show [email protected].

This show is the Property of SP podcasts, LLC, copyright 2025, and is created by Joe Saul Sea. Hi, Joe gets some 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.

[01:02:48] aftershow: You guys have both had 

[01:02:49] Joe: colonoscopies. We gonna do colons was gonna guess. 

[01:02:52] OG: Get teenagers. 

[01:02:53] Joe: Oh, teenagers. Transition 

[01:02:55] OG: to adulthood. Oh yeah. As Alex told me a couple of weeks ago, dad, I’m almost a man. Okay. So one of the things that’s somewhat frustrating is both of my kids really don’t have a, any sort of appreciation for anything that’s not.

Plain food, rice, chicken, you know, just wait a minute. 

[01:03:18] Joe: They’re not both, both of your kids, both of your three kids? 

[01:03:21] OG: No, Caroline’s fine. I’m talking about the boys. 

[01:03:23] Joe: Oh, okay. I was both, both of my kids. 

[01:03:25] OG: Yeah, both of, both of the boys who 

[01:03:26] Joe: got voted off the OG island. Both of the boys. 

[01:03:28] OG: Sorry. Gotcha. Okay. You know, it’s like they don’t eat salad, they don’t put, you know, like 

[01:03:32] Joe: I’ve been to dinner with your family, even at a restaurant.

They’re like, Nope. Not having that, not having that, not having that, having that, yeah, I’m 

[01:03:37] OG: have, I’m gonna have a burger plain and dry with cheese, chicken strips like no ketchup. It’s like, you know, I just failed as a parent. But Alex to his credit, has started to explore a few things and, and now when we have, you know, like Tex-Mex or something, he might have the reef Fri beans in addition to a plain taco with meat on it and a little cheese.

Right. It’s like, okay, we’re starting to do so anyways, so we make rice bowls quite frequently, which is just put chicken in a crockpot with a bunch of seasoning, make some rice, have some black beans. Avocado, tomatoes, little cheese, you know, little, little Chipotle rice bowl, you know, deal. And there’s quite often extras.

So the other day, Alex is making some food ’cause he comes home from school and has to eat and he’s making some food. He goes, dad, I think the rice is bad. And I said, what are you talking about? It’s not bad. It’s, I use the same spoon on the black beans to scoop the right. Like it’s, it’s just, it touched it.

It’s not bad. Like, it’s fine. He’s like, no, I think it, I looked it up, it says rice is only good on the, in the refrigerator for five days. And I’m like, dude, we had this like three days ago. It’s fine. It’s rice. It can’t, like, rice can’t go bad. It’s not able to go bad. It’s science. And he’s like, no, I think this is bad.

And I like, I, he cooks it and I go, no, I’m telling you like I had black beans here also. We had black beans, we had this rice bowls. We had just Tupperware of chicken and rice. And the rice has got a little like little black spots, you know, like, it’s like it’s stained. Like from the black bean spoon and he’s like, still belly.

I go and I’m on the phone and I’m talking to somebody. I said, one day you’re gonna have a teenager and you’re gonna see that they’re so, you know, bent outta shape about like, oh my food can’t touch other food. And I take a big scoop of this rice, I go watch. And I ate it. I said, it’s fine. And he goes, dad, this is from before spring break.

And I said, what are you talking about? This is chicken rice bowls. He goes, no, this is the grilled chicken and rice no. That we made before spring break. No. And he’s like, did you just eat a spoonful of moldy rice and now you’re hurling? And I was like. It’s fine. And he’s like, oh yeah, 

[01:05:41] Doug: you had to take that.

You had to just own it. 

[01:05:44] OG: He’s like, hold on a second. Oh, my teenager doesn’t want to eat moldy rice. He’s like totally throwing it right back at me. And I’m like, well, why the hell are you cooking moldy rice? That’s really stupid. And he just like, he’s like, I tried to tell you. He’s like, look at the bottom of this.

And he like lifts the glass bowl up. ’cause it’s like a glass Tupperware thing, you know, like a glass bowl. It looks up, it’s like all furry. And I just, I just dip my whole spoon in there and I just rah, you know? And uh, he’s like, so what happens next? Do you just get sick or, and I’m like, call an ambulance.

I’m like, no. It’s like penicillin. It’s penicillin. Like this is, they, they, they created medicine out of eating moldy rice. He’s like, I don’t think that’s how they did it. I said, no, that’s exactly how they did. I’ll be fine. And so then the next day, look it up. So I said, look it up the next day. He’s like. So how are you feeling?

And I’m like, I feel fine. Dude. It was like eight grains of moldy rice. It’s not gonna really, he’s like, you should have washed that down. Maybe like, had a bunch of water to dilute it. Like there’s like, it went into a vial of acid. It’s okay. Like, it just, you know, it’s like he was just so worried that I consumed this.

It’s nice. And my wife goes, your dad’s eaten moldy stuff before. And he goes, really? When I was dating Issa, I would always stop at the gas station, partially to get gas, partially to get a can of chew. That was a bad habit back then. And then partially to get a pack of hostess cupcakes. Mm. You know the little, the ones with the little plastic, right?

Mm-hmm. Sugar cake thing on top. That never 

[01:07:16] Joe: expire. Those things never expire. No. Well ’cause they’re not made outta real food. Well, contraire mu for air. Mm-hmm. 

[01:07:25] OG: And so my MO for eating hostess cupcakes is to take the top off in one bite. So you have all the cho Oh, and now you have the cake. Oh yeah. 

[01:07:33] Joe: All that sugar.

[01:07:34] OG: Yeah. So now I just have the cake. I’m driving down the road, I take a big bite, I’m chewing, I’m go. It’s just kind of furry tasting, but it’s like nighttime, right? So I turned the interior light out of the car and it is a big ball of green fur on the inside of this host. So it’s not my first rodeo with, uh, with moldy cheese.

Your immune 

[01:07:57] Doug: system is like Fort Knox. It’s like, come at 

[01:08:01] OG: me rice. 

[01:08:01] Doug: Wow. 

[01:08:02] Joe: I’m the only one in our house. Who too? Who drinks milk. And it’s only from time to time. And I got a little thing of milk a few weeks ago ’cause Cheryl made brownies and I won’t have brownies without my milk. ’cause I’m not special brownies.

[01:08:13] aftershow: Right. 

[01:08:13] Joe: Yeah. And so I, uh, I I see the milk in there like last week. And just open up the top because nobody else is drinking it. Took a big swig, man. 

[01:08:24] OG: And you’re like, that is cottage cheese. That is not milk anymore. It it’s a milkshake. I, oh. I started off hurling. When 

[01:08:32] Doug: are you gonna learn? You keep telling everybody, oh, we’re lactose intolerant.

I’m the only one in my house that drinks milk. 

[01:08:37] Joe: Oh, drink. Fair life. Dude. I told you. I like to laugh. I like to laugh. It is so fun. 

[01:08:42] OG: I mean, you know, fair Life is lactose free. 

[01:08:45] Doug: Just, you know. Yeah. Lact, we, that’s what we have. Fair Life is Maze Ball. Just trying to get rid of every, all the 

[01:08:50] Joe: fun. 

[01:08:50] Doug: But the, uh, I would do the Costco lactose free if I were you.

It’s a heck of a lot cheaper than fairlife. Hey, uh, we were talking about penicillin and I’m the trivia guy. Fun fact, until they started making synthetic penicillin, nearly all of the penicillin in the world came from a cantaloupe in 1946 that was founded at a grocery in, um, Illinois. All the spores came, started from one canal, one cantaloupe.

[01:09:18] OG: Yeah. So was this your trivia A long time ago from one 

[01:09:20] Joe: hostess cupcake 

[01:09:22] OG: Yeah. Found at the convenience store. Was this your trivia Dug one time about, uh, how Tootsie Roll has every single vat of Tootsie Roll has a little bit of the previous Tootsie role in it? 

[01:09:36] Doug: We did, we did talk about that, the phone way.

And so 

[01:09:40] OG: technically your Tootsie Roll now is the same Tootsie Roll as the very first Tootsie Roll. 

[01:09:48] Joe: Sounds great. 

[01:09:49] OG: Yum. Speaking of Tootsie Rolls. 

[01:09:51] Joe: Time to go. Tootsie Roll. Let’s go dance.