Harvard Business Review's Kevin Evers on the Genius of Taylor Swift (SB1671)

Summary

The Stacking Benjamins Show – Episode SB1671: Harvard Business Review's Kevin Evers on the Genius of Taylor Swift

Release Date: April 16, 2025

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Introduction

In this enlightening episode of The Stacking Benjamins Show, hosts Joe Saul-Sehy and OG are joined by Kevin Evers, a senior editor at Harvard Business Review Press. Evers brings his expertise to dissect the strategic prowess behind Taylor Swift's meteoric rise in the music industry. The conversation delves into how Swift's business instincts have propelled her to unparalleled success, offering valuable lessons for entrepreneurs and financial enthusiasts alike.

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Meet Kevin Evers and His Work

Kevin Evers is introduced as a seasoned editor with a rich background in amplifying groundbreaking research and ideas. He has edited best-selling and award-winning books on various topics, including high performance, creativity, innovation, digital disruption, marketing, and strategy. In this episode, Evers discusses his first authored book, There’s Nothing Like This: The Strategic Genius of Taylor Swift, which is a comprehensive case study on Swift’s business strategies.

Notable Quote:

"Taylor Swift has great entrepreneurial instincts. You can't reach this point in her career without great business instincts."
(01:47) – Kevin Evers

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Taylor Swift’s Early Career and Strategic Decisions

Evers begins by exploring Swift's early collaborations, particularly with Robert Ellis Orrall, a seasoned songwriter in Nashville. Despite being only 13 or 14 years old, Swift displayed remarkable business acumen by choosing collaborators who believed in her vision, even when it seemed unconventional.

Notable Quote:

"Taylor Swift was very clear she wanted to write for an audience of her peers. She was very careful to ensure her songs appealed to young girls."
(15:05) – Kevin Evers

Evers highlights Taylor's bold decision to leave her development deal with RCA Records to join Scott Borchetta's independent label, Big Machine Records. This move was pivotal, as Borchetta, heavily invested in Swift's success, was more willing to push her music onto country radio compared to executives at major labels.

Notable Quote:

"Taylor Swift didn’t just wax poetic and rub elbows with Tim McGraw. She said, 'I’d love to open for you on tour,' and she did."
(35:09) – Kevin Evers

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Blue Ocean Strategy vs. Red Ocean Strategy

A significant portion of the discussion revolves around the concept of Blue Ocean Strategy, which Swift effectively employed by targeting an untapped market—teenage girls in country music. Evers contrasts this with the more competitive Red Ocean Strategy, where businesses vie fiercely in saturated markets.

Notable Quote:

"Blue ocean is an untapped market that other people are ignoring. Red ocean is cutthroat, with fierce competition. Most companies operate in red oceans."
(19:43) – Kevin Evers

Swift's ability to create her niche allowed her to become a "category of one" in the music industry, leading to sustained success and loyalty among her fanbase.

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The Importance of Preparation and Authenticity

Swift's meticulous preparation for songwriting sessions and her authenticity are underscored as key factors in her success. Even at a young age, she was prepared with multiple songs, ensuring that skeptics recognized her talent and vision.

Notable Quote:

"She knew that she was walking into rooms where people are going to be very skeptical of her. So she came prepared with multiple songs."
(12:13) – Kevin Evers

Evers emphasizes that Swift's dedication, combined with her ability to listen and adapt, allowed her to rapidly develop her songwriting prowess, improving from one out of two good songs to eight out of ten in just a couple of years.

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Positioning and Marketing: The Case of "Tim McGraw"

Choosing the right single is crucial for positioning in the market. Swift and Borchetta selected "Tim McGraw" as her debut single—a strategic move that balanced traditional country elements with novelty, making it palatable to country radio while still capturing attention.

Notable Quote:

"Tim McGraw was the most familiar song they could promote to country radio at the time, but it still had enough novelty to catch people’s attention."
(32:10) – Kevin Evers

This decision exemplifies how Swift navigated the music industry's gatekeepers by aligning her creative vision with strategic marketing tactics.

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Leveraging Social Media and Grassroots Marketing

Swift's early adoption of platforms like MySpace allowed her to build a dedicated following. By mobilizing her fans to reach out to local radio stations, she effectively used grassroots marketing to gain radio play, which was essential for her breakthrough.

Notable Quote:

"They went to MySpace. Swift had a decent following where she could ask her followers to contact their local stations and request her songs."
(30:02) – Kevin Evers

This strategy not only increased her visibility but also demonstrated her understanding of leveraging digital tools to enhance her reach.

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Lessons for Entrepreneurs and Financial Strategists

Evers concludes by drawing parallels between Swift's strategies and broader business principles applicable to entrepreneurs and financial strategists. Key takeaways include:

1. Surround Yourself with Committed Partners: Align with individuals or teams that have as much at stake in the venture as you do.
2. Embrace Authenticity: Maintain genuine connections and stay true to your vision to build lasting relationships with your audience or clientele.
3. Strategic Positioning: Carefully choose how you present your product or service to appeal to your target market while standing out from competitors.

Notable Quote:

"She understands what her customers are hiring her to do, and that's why they've stuck around for so long."
(16:36) – Kevin Evers

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Conclusion

This episode offers a deep dive into the strategic elements that have made Taylor Swift a powerhouse in the music industry. Kevin Evers provides invaluable insights into how Swift's business decisions, strategic positioning, and authentic engagement with her audience can serve as a blueprint for financial success and entrepreneurial ventures. Listeners are encouraged to apply these lessons to their own endeavors, fostering growth and sustainability in their respective fields.

Notable Quote:

"She was very smart. She knew how to sell her product, but she was also very authentic."
(30:01) – Kevin Evers

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For more insights and to explore Kevin Evers' book, There’s Nothing Like This: The Strategic Genius of Taylor Swift, visit stackingbenjamins.com and check the show notes for additional resources.

Transcript

[Joe]

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[Doug]

Here in this account we have $401,000. Jackpot. No, 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?

[OG]

Live from Joe's mom's basement, it's the Stacking Benjamin Show.

[Doug]

Foreign.

[OG]

I'm Joe's mom's 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? Will 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. Oh, Juju. J.J. one of them looks great in tights.

[Joe]

I was going to 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 over 48 countries. Remember those cool T shirts we made for our comedy club tour a few years ago? That was fun.

[Doug]

Few years ago.

[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 the 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 Stacker Jill send us a tick tock that I can't wait to play for you two guys. I'm just, I'm excited to see what's you're gonna think of that. It's just, it's, this is a gift. This is a show that just is going to keep on giving. Today, you know, the first thing we're going to 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 best selling 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, 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 going to 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 got to pay a dime for great guests like Kevin. So we're going to hear from them people that make this possible and then front and center, today's mentor, the Kevin Evers joining us. This episode is brought to you by Navy Federal Credit Union. We know just how fast your life moves. You've bills to pay, mouths to feed and not a lot of free time. That's why we created an all in one baking experience that lets you keep on banking on it can save you time and money with new lightning fast direct deposit set up and it offers checking accounts with ATM refunds and no service fees. Plus whether you've credit or not, you can build your credit score. With the new ability to report on time bill payments and with personalized financial insights on my making sense, the ability to view all your accounts in one place. Custom notifications and 247 fraud protection. You can get a full picture of your finances. So if you want an all in one banking experience that lets you keep on banking on, sign up today. Learn more@navy federal.org Navy Federal Credit Union Our members are the mission insured by NCUA Small Business Owners. State Farms there with small business insurance to fit your specific needs. Whether you're starting a new venture or growing an existing one, State Farm helps you choose the right coverage to protect what matters most. Working with a local State Farm agent helps you understand your coverage options. Offering local support to help you achieve your goals. Focus on turning your passion into a thriving business. Knowing your insurance can change as your business grows. Stay Farm here to help you succeed with your business like a good neighbor. Stay Farm is there and I'm super happy. This gentleman's coming down to the card table. Kevin Evers is here. How are you, man?

[Kevin Evers]

I'm doing great.

[Doug]

How are you?

[Joe]

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 cool Apple. Why in this project, why Taylor Swift of all things?

[Kevin Evers]

Kevin I have to say, it did not take much soul searching to do a case study or a book on Taylor Swift. She 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 eras 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.

[Joe]

I always get interested in the art of diving into a company, or in this case, the company that is Taylor Swift.

[Kevin Evers]

Yep.

[Joe]

You begin with her collaborators and the collaborations that she has early on. I want to. I want to 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?

[Kevin Evers]

Yeah, let's do it. Robert was a, or still is, 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.

[Joe]

I'm just imagining Kevin, you know, he gets this. I don't know if it was an email at the time or, you know, because 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?

[Kevin Evers]

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 two, three, four 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 gonna go right with a 13 year old girl. Because this wasn't pop music. It was really rare for someone so young to try to make it in country music because country music did not believe that there is 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.

[Joe]

You said at one point, and we'll talk about this later about 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.

[Kevin Evers]

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 Bruschetta, 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 out of 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 going to go with him instead of going with a major label, which was a big decision. Now, in hindsight, that definitely worked out for her.

[Joe]

What did people, her, these early collaborators like Orel, 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?

[Kevin Evers]

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. And that was the part that surprised me because 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 Orwell in the book where he says, this girl's gonna sell a million copies of her album after the first day he met her, 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 were 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.

[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, like you're impressed by her preparation. Even at 13 and 14 years old, this young woman shows up, Kevin, to every meeting, intensely prepared.

[Kevin Evers]

Yes. She knew that she was walking into rooms where people are going to be very skeptical of her. So she said, I'm going to come in prepared. I'm going to have multiple songs that are near ready. So when I go into those songwriting sessions, I'm going to 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.

[Joe]

It's Like I'm thinking about Sun Tzu in 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 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?

[Kevin Evers]

You know, Robert Earl 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 out of 10 were really, really good.

[Joe]

Eight out of 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 time frame.

[Kevin Evers]

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 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.

[Joe]

She wasn't afraid either at 13 or 14 to share her opinions. Kevin, with these, we'll call them old men, even though I'm a 57 year old guy. But she's telling them where she thinks that they're wrong, where other professionals maybe, you know, they maybe have a. I don't know if it's a healthy amount of respect or too much respect for these people that she's collaborating with.

[Kevin Evers]

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 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, 45 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.

[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 them out and perform them. I mean, 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.

[Kevin Evers]

Yeah, pop music. If you look at over time, the amount of songwriters on each song has increased. I don't know the exact step, but you know, it's usually four or five songwriters to a song these days. A single song on 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 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 was right in her sweet spot and that's why her audience were really receptive to what she was doing.

[Joe]

It's incredible, I think the analogy, because I know for our average listener, it's hard for them to go, Taylor Swift, what does this have to do with me? Yeah, but I think a lot of this, Kevin, is controlling your supply chain. Right? I mean, understanding where the cracks are and really knowing exactly what it is that you're selling to, the people that you're selling to.

[Kevin Evers]

Oh, that it's, it's so critical, 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 because 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.

[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 that's wanting to be on a stage, Kevin has thought that. 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. 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 this. Like, how do we learn from that?

[Kevin Evers]

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 in 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.

[Joe]

It's funny because people can hear what you just said and they could go, oh, okay, well, then I can't do it because I don't have any of those things. But you make a great point, which is lead with your strengths. But you still got to grab that strength. Like, just because she has these. These advantages, we'll call them Kevin, doesn't mean she's going to take advantage of them. Taylor really jumped in and took advantage of it.

[Kevin Evers]

I mean, there's plenty of people who are 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.

[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?

[Kevin Evers]

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. 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.

[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.

[Kevin Evers]

Yep.

[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 of teenage girls.

[Kevin Evers]

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 executives in country music were like, ah, you know what, I don't think there's a market here because that's what the data said.

[Joe]

What's going on in the national music scene at that time?

[Kevin Evers]

In what regards?

[Joe]

Well, I'm 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.

[Kevin Evers]

Oh, the record companies, yeah, for sure. The number of record labels at the time was shrinking because around that time, remember, this is the post Napster age in the heyday of the music industry, which is in the late 90s, 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 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.

[Joe]

You've got these record label executives then running scared, afraid for their own jobs. So how are you going to 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 going to 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.

[Kevin Evers]

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 ATV 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.

[Joe]

That's some waves.

[Kevin Evers]

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 Burchetta, who he'd mentioned earlier, Scott Borchetta 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 Bruschetta 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's 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's 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 want to sign you to a record deal.

[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.

[Kevin Evers]

Yeah.

[Joe]

Andrew's 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.

[Kevin Evers]

And this is something Scott Bruschetta has said about Jessica Andrews. He said that she didn't quite have the vision to make it because 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.

[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.

[Kevin Evers]

Yeah.

[Joe]

And they popped this CD in at the time, at around this time with LeAnn Rimes. Leanne Rimes is another name that you mentioned of a young star that also struggled later on. I remember hearing her sing that 50, 40s or 50s song, Blue.

[Kevin Evers]

Yeah.

[Joe]

And this is a song that clearly is older than her age. And she's singing this completely retro song. So effing beautifully. Just so.

[Kevin Evers]

Yeah, yeah.

[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.

[Kevin Evers]

Yeah. And LeAnn 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, because Taylor wasn't one of these polished teenagers, these showbiz 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 are 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 miss Chances, too.

[Joe]

I've got a couple more themes I want to talk about before we let you go. The next one is specifically this collaboration with. With Baretta. He 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. Brushetta, though, tells her that he's not staying around Universal. Like, he's going to go do his own thing. Yeah, I can't imagine, Kevin, if. If you believed in me and stacking Benjamins. And then at the end that conversation, I'm like, kevin totally gets me. And then, dude, you go, but I'm leaving the company and I'm going to create this thing. And I'm not sure if I'm going to have funding, but, hey, you got to wait for me.

[Kevin Evers]

Yeah.

[Joe]

Like, this is a ballsy move for a girl who's 15, 16 years old. Where's the business lesson there? I guess for all of us.

[Kevin Evers]

The business lesson for me is Scott Bruschetta had much more skin in the game than an executive at a major label. They had a tall hill to climb. They had to 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.

[Joe]

Oh, she aligned herself with somebody with as much at stake as she had.

[Kevin Evers]

At stake, for 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 because 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 they should be promoting. This is the girl that is going to find success in country music. But since Bruschetta 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.

[Joe]

You write that the founder of Y Combinator wrote that 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. Now we actually got to do the hard part, which is connect with the audience. While Taylor Swift has some music connections, she's not somebody like Miley Cyrus, who, you know, came out of a. Came out of a Disney Channel came.

[Kevin Evers]

Out of Disney, right?

[Doug]

Yeah, yeah.

[Joe]

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.

[Kevin Evers]

In Taylor Swift, 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.

[Joe]

I'm still friends with that one guy from MySpace.

[Kevin Evers]

Are you. Is it Tom? Is that his name? I believe? Yeah, Tom. I'm still around, yeah.

[Joe]

Yep.

[Kevin Evers]

So they went to MySpace. Taylor had 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 worked.

[Joe]

It's like surrounding these record executives.

[Kevin Evers]

Yes, exactly. That's exactly what they did. Once she was played on country music radio, they sent Taylor on a six month tour to all the radio stations. Oh, man, 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 went a six month tour.

[Joe]

She knows what she's selling. I mean, she knows 100% what she's selling completely.

[Kevin Evers]

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.

[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, Right?

[Kevin Evers]

Oh, for sure. Yeah. Or media, like too much media training. You know, it's. 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 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 feeder kid energy which is really unique to who she is. And she played up those qualities. She didn't try to hide them.

[Joe]

Last thing I want to Talk about is positioning. Because when you're first breaking into a market, I think positioning is incredibly important. She has all these different songs to choose from as her first song. And. And you write that getting that single right is going to be a huge, huge part of her success or failure. And both Scott and Taylor know this. How did they choose her first single?

[Kevin Evers]

So they ended up going with a song named Tim McGraw, which is a very clever title. It's the perfect mix of.

[Joe]

By the way, for people that don't know Tim McGraw is a current country singer.

[Kevin Evers]

Yes.

[Joe]

Right, then, so. So they pick a single that people are gonna go, Tim McGraw. Wait, the Tim McGraw?

[Kevin Evers]

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 focus, 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 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.

[Joe]

What's interesting about that, to me, Kevin, as 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, but she has to convince the person at the record company. She's got to 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 can just imagine if, you know, one of her later hits, if she tried to start with some of the stuff she writes now, she would have lost them immediately. Like, are you kidding me? This isn't country music for sure.

[Kevin Evers]

And that's why it was such a wise decision. And she had other songs on that album that she could have 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.

[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?

[Kevin Evers]

Yeah, for sure. April 8th.

[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. She ever reach out to Tim McGraw?

[Kevin Evers]

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.

[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?

[Kevin Evers]

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 this is? I'd love to open for you on tour. And she did. She ended up opening up for him, too.

[Joe]

She. She did. I didn't know that. Yeah, I felt like Glengarry Glen Ross there. For people that don't know, you know, always be selling.

[Kevin Evers]

Yeah, always.

[Joe]

Taylor's always selling.

[Kevin Evers]

She's always selling. For sure.

[OG]

Hey there, Stackers. I'm Joe's mom's neighbor, Doug, and, okay, huge misunderstanding. It's wear your pajamas to work day and happy you're late filing your taxes day. While I'm too busy busy celebrating to just yet file my taxes. I did just come down here in my pajamas. Check it out, guys.

[Joe]

Whoa.

[OG]

Hey.

[Joe]

No, you're naked.

[OG]

But, yeah, that's the thing. I don't wear pajamas. This is how I sleep.

[Doug]

Somebody let a gorilla loose in here. That's a lot of body hair.

[OG]

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, are taxes now due? 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.

[Doug]

Gross.

[Joe]

As a contractor, I don't pay for materials I don't use so why would I pay for stuff I don't need.

[Doug]

In my mobile plan?

[Joe]

That's why the new My Biz Plan from Verizon Business is so perfect. Now I can choose exactly what I.

[Doug]

Want and I only pay for what I need right now with my Biz plan. Get our best price as low as 25 a line. Visit verizon.com business to get started today. Price per month with 5 plus lines includes auto pay and paper free billing and special intro offer discounts, taxes, fees, economic adjustment charge and terms apply. Offers in June 10, 2025 at Capella.

[Joe]

University you can learn at your own.

[Kevin Evers]

Pace with our flexpath Learning format.

[Joe]

Take one or two courses at a.

[Kevin Evers]

Time and complete as many as you can in a 12 week billing session. With Flexpath, you can even finish the Bachelor's degree you started in 22 months for $20,000.

[Doug]

A different future is closer than you.

[Kevin Evers]

Think with Capella University. Learn more at capella.edu fastest 25% of students cost varies by pace, transfer credits and other factors.

[Joe]

Fees apply.

[Doug]

Race the rudders. Race the sails. Race the sails.

[Joe]

Captain, an unidentified ship is approaching. Over.

[Doug]

Roger, wait, is that an enterprise sales solution? Reach sales professionals, not professional sailors.

[Joe]

With LinkedIn ads, you can target the.

[Doug]

Right people by industry, job title, and more. We'll even give you a $100 credit on your next campaign. Get started today at LinkedIn.com results terms and conditions apply.

[OG]

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 someday I'll get to celebrate a full day of wearing pajamas to work day. 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 miss out. Understood how this thing works. You want to get them 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 I'm going to send you back.

[Joe]

To Joe and Og and oh gee, Doug's Right. Those failure to pay penalties fairly, fairly big. What if. What if somebody doesn't have the money? Do you like the payment plan system that the IRS has?

[Doug]

Straight to jail, go to.

[Joe]

Just, Just turn yourself in.

[Doug]

Turn yourself in.

[Joe]

Can you imagine somebody walking in, I owed $18. You should just take me.

[Doug]

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.

[Joe]

Yeah.

[Doug]

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 8 or 10%.

[Joe]

On top of that.

[Doug]

Yeah. 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. 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.

[OG]

Oh, gee, I've got another question for you. You know, it's not, not for me, but a friend of mine asking for a friend. Sure. 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 mean, how are they supposed to know how much to pay?

[Doug]

Yeah, well, you just have to know so you. You.

[OG]

Oh, thanks. So helpful.

[Joe]

It sounds like a Naper Gazzy answer. Nobody knows. Nobody knows.

[Doug]

Yeah, nobody knows. It's. You have to round up. I mean, if you seriously don't know, 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. Your. 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.

[Joe]

Time for our tick tock minute. Speaking of reliable facts and getting reliable facts, this is the part of the show where we shine a light on a tick tocker who might be providing reliable facts or maybe not providing reliable facts. And before I have you guys 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 Cardone Real Estate, Sardone.

[Doug]

It's a silent. It's a soft ass.

[Joe]

So. Oh, gee, you think Cardone is bringing it today or air quotes bringing it?

[Doug]

Absolutely. I've seen his airplane. This dude is nothing if not bringing it.

[Joe]

Bringing it. Yeah. Doug, how about you?

[OG]

Well, if it's Grant Sardone, then I don't buy any of it.

[Joe]

But maybe fairly certain it's Cardone in this case.

[OG]

It's like a spoof account for Grant Cardone.

[Joe]

Oh, this sadly is no spoof because here's Grant Cardone in the middle of an interview.

[OG]

I have a lot of money in my 401k.

[Kevin Evers]

Okay, I'm sorry for you.

[Joe]

Why do you feel sorry for him? 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?

[OG]

Higher.

[Doug]

You will wish you would have sold.

[Joe]

Them when you were 50. You'd pay lower taxes.

[Doug]

Dude, you don't pay any taxes when.

[OG]

You pull out money out of your 401k.

[Joe]

If you wait until you're 63 when you start using that money, you're going to pay taxes. You weren't charged taxes while it sat there.

[Doug]

What's wrong with you?

[Joe]

You're not.

[OG]

IRS allows penalty free withdrawals from retirement accounts after the age of 59 and a half.

[Joe]

Penalty free, not tax free. So they're going to charge you a penalty. They're going to put handcuffs on you to sell it before then. But dude, when you're 63 years old, when you start withdrawing, you're going to start paying taxes at that point.

[OG]

401K withdrawals are taxes, Inc.

[Doug]

Exactly.

[Joe]

I have a. Oh boy. I feel like we have two idiots sitting across right here.

[Doug]

Penalty free.

[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 anyway.

[Doug]

Well, I think he said 63 because of the guy said at 63 he's going to 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 you see different people be successful in different areas and you go, well, that guy is the exception to the rule. Because 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 are wildly successful who 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 people.

[Joe]

He's true genius right there.

[Doug]

But him to say, oh well that, that, that, that's ridiculous. I mean that's no different than me saying buying real. 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 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, that's.

[Joe]

Actually the win that you can't touch it.

[Doug]

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. Recaptured depreciation when you sell your real estate portfolio. Because the really cool thing 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 are on April.

[Joe]

And that's what frustrates me about this, is not that real estate can't be a great way to go. It's him pooh, poohing the other. Other avenues, I mean, that are out there going, oh, that's a trap.

[Doug]

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. 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, take some cash, bro. Make it happen.

[Joe]

That's my son, you know?

[Doug]

Yeah, same thing with Nick, right? Like, if I needed to buy a house in Detroit, I would. 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 fire a little bit.

[Joe]

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. 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.

[Doug]

Yeah, everything has a downside. Everything has a equal and opposite reaction.

[Kevin Evers]

I don't know.

[Doug]

That sounds stupid.

[Joe]

While getting all scientific on us.

[Doug]

No, I just made that up.

[Joe]

Let's do a headline. How about that? Hello, darlings.

[Doug]

And now it's time for your favorite part of the show, our stacking Benjamin's headlines.

[Joe]

This comes to us from cnbc. I found this last week, guys. Trevor Lawrence, Joaquims wrote this.

[Doug]

Nobody was on CNBC last week, believe.

[Joe]

It or not, I saw something unrelated to tariffs and I'm like, please God, let's talk about it.

[OG]

Took you 20 minutes to dig for it, but you found one?

[Joe]

It did. If I could not talk about tariffs for three minutes, that would be fantastic. Trevor writes whether to buy cryptocurrency as a long term holding may be the biggest decision an investor interested in digital assets has to make. But where to store crypto like bitcoin, well, that can become more consequential, the most consequential, he writes. 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 illegible, 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.

[OG]

It's a USB memory drive, you sickos. Get your mind out of the gutter.

[Joe]

I don't even know where it would be in the gutter.

[OG]

But anyway, all you said was device in my hand. So that could you take.

[Joe]

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 were. Hot wallet. Sounds to me like you may need to go see a doctor.

[Doug]

I mean, I've heard of prison wallet, but that's a different thing altogether.

[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 the 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.

[Doug]

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. How many times have you found a $20 bill in a coat pocket from 15 years ago?

[Joe]

You know, I was literally just getting ready to take a coat to Goodwill last week, and there was a hundred. A hundred dollar bill in the pocket that has probably been there for 10 years. I have no idea. When I came across.

[Doug]

It's like a. It's like a 70 bill.

[Joe]

I. I know I had no. I had to. Well, for me, Doug, especially how much.

[Doug]

You know, how rich I am. I can have 100 bills. And I've got on record over and.

[Joe]

Over saying that if I've got 10 bucks in my pocket, I'm spending it right. Right now. Like, that is.

[Doug]

What did you buy?

[Joe]

The key to my success. Oh, a board game, of course. Yeah. Inflation is eating that alive.

[Doug]

I got a couple of gift cards. 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 going to come as like a gift card gift card. And it was a digital one. I'm like, ah, crap. Like, what are you going to do with 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, so 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, it comes up with this weird. You know, it's just a weird gift card thing.

[Joe]

Yeah.

[Doug]

It's not like, literally tagged. I feel so free right now with cash because I'm like, who cares? Like, Jimmy Johnson, everybody. Of course we're getting pro V1Xs right now. Why wouldn't we? $4 a golf ball. Who cares? You're going to launch them into the lake. It's like free money. So you found free money. $100.

[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. Oh, gee. 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 just, just. 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.

[Doug]

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 safest place for all of those things. And when you start talking about stuff that's around the house, we've got cash at home. I think you guys have some cash at home in a drawer or something. Helps to have a few bucks. But when you have valuables in other places, what could go wrong with that? If you have people at your home? Joe, you've talked about on the show, you had a house break in, and you largely suspected it might have 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 don't know, soliciting, you know, roof repair or something. And he goes, no dogs in the house. And that was the weirdest thing.

[Joe]

Wow.

[Doug]

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 them 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, just kind of curious. I was just like, whatever you're selling, I definitely don't want now. And we are going to 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. It's like, oh, good.

[OG]

Actually, I have two Dobermans. And I. And. And as a.

[Doug]

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 want to 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.

[Joe]

I've got a dash. And that's a big one, right? It's a dashing.

[Doug]

It's like I got one of those wiener dogs that like yip all the time. Like, get your ankles.

[OG]

I don't know, man. Cats are terrifying. You just don't know what they're going to do. And they've got the. And. And I don't know, I get two Dobermans and I think I might need to add a cat into the mix just to.

[Doug]

I was telling you that Doug, that 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.

[OG]

Wow.

[Doug]

Professional dog. This thing is like a horse and it looks so scary. I'm like 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 because they do that, you know, so that, you know, you can't.

[OG]

Portuguese, that's the language.

[Doug]

Well, it's German. I know generally, but you know what I mean? Like they train them in different languages so you can't say like, stop. You know.

[Kevin Evers]

Right.

[Doug]

It doesn't know it. That you have to, you know, or whatever. I don't know. But 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. Like, no, no, no. Like what's the. Do I sell? What do I tell people that I have so that they get scared?

[Joe]

The reason I brought up, I don't.

[Doug]

Know how we got to that. That's just story hour with OG Fun. Just.

[Joe]

Well, 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 ARP website right now. Most. Most scams against older.

[OG]

It comes up automatically when he starts his browser.

[Doug]

I know most scams against Joe older.

[Joe]

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.

[Doug]

Tell me the things that are top of Joe's mind right now. That's what I want to know. Oh, we don't have to guess. We know. AARP lot break inside, you know, or top of top of Joe's mind. You're worried about cousin Larry all of a sudden. The other thing that I want to. Just want to 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 or in the safe or something like that, you better know what your insurance is going to 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 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 your exposure is when you make a decision around a specific thing. I want to have lots of cash at home because it makes me feel safe. Great. But what if the house burns down? What happens? 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 going to 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 a new one.

[Joe]

Yeah, you really around. Your birthday is a great date. Look at your policy. Make sure the policy's up to date.

[Doug]

Happy Birthday. Let's read insurance statements.

[Joe]

It's also a good opportunity to just compare pricing. One 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. 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 cold storage. Yeah. Had their things on it. Of course, this piece also says even when you're using a third party custodial option, like a Charles Schwab is an example for your stocks or Fidelity or Vanguard or something, with your crypto, there are steps to help you remain vigilant against the threat posed by cybercriminals. The use of two factor authentication is important, strong passwords. The US Marshal Service within the 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 notes@Stacky Benjamin.com and 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. What do we got on the back porch today, man?

[OG]

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.

[Joe]

I know, right? And we now have another one, The Amazing Kevin Evers book. I'm going to be. I'm. I'm now done with this amazing work. So we got to give away some more books. And we do that in exchange for. It's not really an exchange if you do a review. And 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 they can just request the book and I may have given it away already, so. Well, I can't give you a choice. 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, want to say a big shout out to Debeney, 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 interest on his. On his money.

[OG]

Joe, you still owe me 500 bucks, by the way. I don't know if you remember.

[Joe]

That's from 20 years ago at 8% interest. Right. We do have a lot of books. So write me joestackybenjamins.com and let me know if you left us a review someplace. And happy to make sure that we send an intern to the post office because 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 going to 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 a round table. The retirement answer man. Roger Whitney, Alyssa Mazes from South Florida, a great CFP down there, and the OG all talking about your eras. Right? We're going to 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 30s and 40s, how should it change? And then as you near retirement and are in retirement, what are the important things? We're going to dive into your portfolio using Taylor Swift as a theme, since we've done that all week. And then next week, we're going to get tactical. We were all strategy, right? Now we're going to dive into tactics. Lorraine Lee is going to join us. And all week long, we're diving into the tactics of your career brand. What I love. And Doug, you and I were laughing about this earlier. Is that 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.

[OG]

You don't know what it is, it's bad.

[Joe]

So we're going to help you with your career branding tactics. Next week, we go from strategy to tactics. That's going to be fun. All right, enough foreshadowing, Doug. Lots of takeaways. What are the big three today?

[OG]

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 what they call income. So, I mean, you've all heard of tax free. Oh, gee. 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 [e-mail] this show is the property of SP Podcasts, LLC, Copyright 2025 and is created by Josal Sehive. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome [e-mail] along with the show notes and how you can find us on YouTube and all the usual social media media spots. Come say hello.

[Joe]

Oh, yeah.

[OG]

And before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug, and we'll see you next time back here at the Stacking Benjamin show.

[Doug]

Sa. You guys have both had colonoscopies? We're gonna do teenagers.

[OG]

Oh.

[Doug]

Teenager transition to adulthood.

[Joe]

Oh, yeah.

[Doug]

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, Wait a minute. They're not both.

[Joe]

Both of your kid. Both of your three kids?

[Doug]

No, Caroline's fine. I'm talking about the boys.

[Joe]

Okay, Both. Both of my kids. Both. Both of them who got voted off the OG Boys.

[Kevin Evers]

Sorry.

[Joe]

Gotcha.

[Doug]

You know, it's like, they don't eat salad. They don't put, you know, like, I've.

[Joe]

Been to dinner with your family, even at a restaurant. They're like, nope, not having that. Not having that and having that.

[Doug]

And I have. I'm gonna have a burger, plain and dry with cheese, chicken, 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 refried 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. Anyways, so we make rice bowls quite frequently, which is just put chicken in a crock pot with a bunch of seasoning, make some rice, have some black beans, avocado, tomatoes, little cheese, you know, a little. Little chipotle rice bowl. You know, deal. And there's quite often extras. So the other day, Alex is making some food because 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. I use the same spoon on the black beans to scoop the rice. 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 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 this 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, you know, 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 going to have a teenager, and you're going to see that they're so, you know, bent out of shape about like, oh, my food. Can't touch other food. I take a big scoop of this rice. I go, watch. And I ate it. I said, it's fine. 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.

[Joe]

No.

[Doug]

That we made before spring break.

[OG]

Oh.

[Doug]

And he's like, did you just eat a spoonful of moldy rice?

[OG]

Now you're hurling.

[Doug]

And I was like, it's fine.

[OG]

And he's like, oh, yeah. You had to take that. You had to just own it.

[Doug]

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. I'm like, well, why the hell are you cooking moldy rice? That's really stupid. And he's 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 because it's like a glass Tupperware thing, you know, like a glass bowl. And looks up. It's like, all furry. And I just. I just dip my whole spoon in there, and I just. Rah. He's like, so what happens next? Do you just get sick or ambulance? I'm like, no, it's like penicillin. 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, it'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.

[Joe]

It's nice.

[Doug]

And my wife goes, your dad's eaten moldy stuff before. And he goes, really? When I was dating Lyssa, 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. You know, the little, the ones with the little plastic.

[Joe]

Right.

[Doug]

Sugar cake thing.

[Joe]

They never expire. Those things never expire. Well, because they're not made out of real food.

[Doug]

Well, contraire. Move rare. And so my MO for eating Hostess cupcakes is to take the top off in one bite. So you have all the chocolate, and now you.

[Joe]

All that sugar.

[Doug]

Yeah. So now I just have the cake. I'm driving down the road, I take a big bite. I'm chewing. I'll go, this is kind of furry tasting, but it's like, nighttime, Right. So I turn the interior light out of the car, and it is a big ball of green fur on the inside of this Hostess Cupcake. So it's not my first rodeo with, with moldy.

[OG]

Your immune system is like Fort Knox.

[Doug]

It's like, come at me, rice.

[Joe]

Wow. I'm the only one in our house who, who drinks milk, and it's only from time to time. And I got a little thing of milk a few weeks ago because Cheryl made brownies, and I won't have brownies without my milk because I'm not special.

[Doug]

Brownies, right?

[Joe]

Yeah. And so I, 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.

[Doug]

And you're like, that is cottage cheese. That is not milk anymore.

[Joe]

Oh, when are you going to learn?

[OG]

You keep telling everybody, oh, we're lactose intolerant. I'm the only one in my house that drinks milk.

[Doug]

Oh, drink Fair Life.

[Kevin Evers]

Dude, I told you.

[Joe]

I like to laugh. I like to laugh. It is so fun.

[Doug]

No, I mean, you know, fair life is lactose free.

[OG]

Yeah, we. That's what we have.

[Doug]

Fair life is amazing.

[Joe]

Just trying to get rid of every.

[OG]

All the fun, but the. I would do the Costco lactose free if I were you. It's a heck of a lot cheaper than Fair Life. Hey, 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 found at a grocery store in Illinois. All the spores came. Started from one cantaloupe.

[Doug]

So was this your trivia? A long time ago?

[Joe]

From one Hostess cupcake? Yeah. At the convenience store.

[Doug]

Was this your trivia, Doug? One time about how Tootsie Roll has Every single vat of Tootsie Roll has a little bit of the previous Tootsie Roll in it.

[OG]

We did. We did talk about that.

[Doug]

And so technically, your Tootsie Roll now is the same Tootsie Roll as the very first Tootsie Roll.

[Joe]

Sounds great. Yum. Speaking of Tootsie Rolls, time to go Tootsie Roll.

[Doug]

Let's go dance.