The iPod’s Legacy in the Music Industry with Zack O’Malley Greenburg

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On this episode, we switched things up! Instead of a standard interview, I talked about a few recent topics with the best-selling author, Zack O’Malley Greenburg. He has long had his pulse on the music industry. Between his past time covering the business at Forbes, writing acclaimed books on the likes of Jay-Z and Michael Jackson, or his current Substack blog, Zack has formed both a macro- and micro-view of the entire industry. He’s the perfect person to bring onto Trapital to discuss the stories reverberating across the music business today.


One of those stories is Spotify’s floundering performance as of late. The streaming leader’s stock has cratered to all-time lows, partly due to so-so performance, but also as a byproduct of Netflix’s own struggles. But if you ask Zack, the commonalities between Netflix and Spotify aren’t as close as critics will have you believe. Specifically, Spotify’s “unlimited buffet” business model is a massive differentiator. 


And then there’s Apple officially discounting the iPod after 21 years. Whether it gets the credit or not, the innovative product re-shaped the music business into what we see today. As a “legal Napster”, it laid the groundwork for today’s streaming-dominated industry — not just for music, but podcasts too. 


Check out all the topics Zack and I covered in this episode of Trapital:


[0:00] Zack’s First Experiences with The iPod

[6:11] Steve Jobs First iPod Keynote

[8:33] iPod As A Gateway Into Apple Ecosystem 

[12:16] Will iPod Have A Resurgence Like Vinyl? 

[14:48] U2’s Free Album On Apple Backfires 

[18:55] Spotify’s Current Business Struggles

[20:09] Why Spotify Shouldn’t Be Compared To Netflix

[27:23] Do Spotify And Netflix Have Content Problems?

[33:00] Examining Bad Bunny’s Meteoric Rise In Six Years

[38:21] Latin Music Succeeding In US Despite Language Barrier 

[40:12] Did Jay Z Ruin Robinson Cano’s Career?


Listen: Apple Podcasts | Spotify | SoundCloud | Stitcher | Overcast | Amazon | Google Podcasts | Pocket Casts | RSS


Host: Dan Runcie, @RuncieDan, trapital.co


Guests: Zack O’Malley Greenburg, @zogblog


This episode was brought to you by Highlight. Build the community of your dreams on the blockchain. The new company is backed by leading investors like Haun Ventures, Thirty Five Ventures (“35V”), and more. Learn more at highlight.xyz



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Trapital is home for the business of hip-hop. Gain the latest insights from hip-hop’s biggest players by reading Trapital’s free weekly memo




[00:00:00] Zack O’Malley Greenburg: If you’re a startup and you’re looking for celebrity investors and, I know that the market is cooled down a bit, but still, you know, you’re in a fairly mature startup. And you’re trying to get your name out there a little more by getting, you know, music investors, celebrities, et cetera. The kind of reach that he has, especially if you’re trying to get into the Spanish language market. It’s untoppable and, you know, I just think there’s a tremendous opportunity there and in a lot of other places for him too.

[00:00:29] Dan Runcie: Hey, welcome to the Trapital podcast. I’m your host and the founder of Trapital, Dan Runcie. This podcast is your place to gain insights from executives in music, media, entertainment, and more who are taking hip-hop culture to the next level.

[00:00:49] Dan Runcie: On today’s episode, we switched things up a little bit. This is normally an interview-style podcast, but I did a recent survey. And many of you say you wanted to hear more from me. You wanted to hear my insights, my perspective on this space and where things are heading. So it was a great time to invite back Zack O’Malley Greenburg.

[00:01:08] Dan Runcie: You may know him from his work at Forbes, where he started a lot of the reporting on how much money hip hop artists were making and the potential for what they could do in the business world. So we covered a bunch of topics in this episode. First, we talked about the iPod. Apple recently announced that they are discontinuing the influential device after almost 21 years in its production. So Zach and I talk about the device’s importance and influence. Then we talked about Spotify. The stock is trading at an all-time low. So we talk about what does that mean for streaming? What does that mean for music and, more broadly, how does that compare to video and other types of streaming?

[00:01:45] Dan Runcie: Then we talked about the current king of streaming, of the current king of Spotify. Bad Bunny is the biggest artist in the world. So we talk about the impact and importance of what that means for a Latin artist, a Latin artist, who is yet to do a song in English and how cool that is. And then we close things out where we talked about Robinson Canó, who is a baseball player and how his career took a bit of a different turn after he sides with Jay-Z’s Roc Nation sports agency.

[00:02:12] Dan Runcie: Hope you enjoy this episode. If you do, send a note and let us know, because that’s the type of stuff that encourages great content. I hope you enjoy it. Here’s our conversation. All right. We got Zack O’Malley Greenburg with us today and we are going to cover a bunch of topics. And the first one that’s near and dear to both of us is we got to pour some out for the iPod. After almost 21 years, the device that changed the game, Apple announced it’s discontinuing it.

[00:02:38] Dan Runcie: And it’s a great time to talk about its legacy, its impact. So first let’s start here cause I know that you likely owned a bunch of these. I did too. How many iPods did you own and which version was the first one you got? 

[00:02:50] Zack O’Malley Greenburg: Oh man. You know, I think I had originally one of the clunky ones that didn’t have sort of like the touch wheel, you know, like the kind of mano, you know, the, what is it like the black and white kind of a janky one.

[00:03:02] Zack O’Malley Greenburg: But the one that really sticks in my mind was right around the time that Bono was doing all those commercials. And I remember my godfather was like, I want to get you a nice present for your birthday. He’s like, I want to get you like, like a personal DVD player. And I was like, that’s very sweet of you. And I really appreciate that. Can I have an iPod instead?

[00:03:23] Zack O’Malley Greenburg: He was like, what’s this iPod? But yeah. I mean, it was, I think that one that must have been. I don’t know, maybe around 2005, that was when they started getting really sexy-looking. And, and you had the touch wheel and you had kind of like the sleek black look on it instead of like, you know, sort of like the white witch, which would get kind of, you know, get kind of grimy, at least mine did.

[00:03:47] Zack O’Malley Greenburg: But this was sleek. I think the back was silver. I mean, it was really a work of art and that was when I started thinking it’s only a matter of time before they just make one of these as a phone, you know? And I’m sure, you know, having talked to people at Apple over the years, by the time they put out that iPod in the mid-aughts, they already had a design on the iPhone, but there would have been no, you know, no iPhone if there weren’t an iPod.

[00:04:10] Zack O’Malley Greenburg: You know, in many ways, I think the iPod saved the music industry, right? I mean, when they created that ecosystem, it just became easier to get your music, you know, through the legal means than by downloading them, you know, downloading those MP3s illegally and say what you will about the depth of the album and the issues of like breaking up albums and selling them single by single.

[00:04:31] Zack O’Malley Greenburg: But, you know, I think that really provided the bridge that the music industry needed to get to the streaming era. So yeah. Pour one out, indeed. How about you, Dan, what was your first?

[00:04:41] Dan Runcie: Ah, yeah. So the first one for me, let’s see, I want to say it was 2004, I bought the iPod mini because I didn’t have a Mac at home. So I waited until they were compatible on PC.

[00:04:54] Dan Runcie: And I added, I think I was working either at Dairy Queen or I was working at our local parks and rec at the time. And one of the first paychecks I had, I was like, no, let me go take this, buy iPod mini. So I had that, but listen, after two months of having that, and I was one of the first people in the school to have one at the time. I left it in my pocket and put it in the washing machine, like a typical teenager would, and that thing gets ruined. Right. So then I was like, okay, fine. Let me get another one. This time I was making CDs at the time, I was burning them and selling them in school. So I said, okay, I need a bigger operation here. Let me get the full-on classic one.

[00:05:34] Dan Runcie: Got that, within two months of getting that, so this is around the time of high school graduation. I put the bag into this bleacher area by the school where we had the graduation. I go back after graduation. Someone takes that bag, someone in the class must’ve seen me put it there, and then that was gone. So then by the time I’m entering in college, I said, you know what?

[00:05:55] Dan Runcie: I just need to get another one. So I bought three iPods within an 18-month period. It’s one of the most ridiculous things. And obviously for the kid that was making $7 an hour at various jobs, would be at a camp counselor, working at Dairy Queen and other places. That’s what I spent my money on. I bought it on iPods.

[00:06:11] Dan Runcie: So I had to go into freshman year of college, fresh with of those things, but as I had that, that one I did have for a while though, I kept that one for a number of years. And I think I eventually got a Shuffle later on for running and stuff like that. So I think, so I guess I had four devices total, but I agree with you. Take a step back, thinking about the device overall. I’d actually went back and watched Steve Job’s keynote that he initially did.

[00:06:35] Dan Runcie: And he had done keynote presentations before for all the other products that he had throughout the years. But I feel like this one is the one that really turned to the pop culture aspect of the Steve Job’s keynote with, he was no longer wearing the suits. He’s wearing the black turtleneck tucked into the jeans.

[00:06:51] Dan Runcie: Takes the iPod out of the pocket, has the “hundred songs in your pocket” quote. And I think, from there, what you mentioned too about the bridge that this was for streaming. It makes a lot of sense, right? I mean, look at the way iTunes is set up. iTunes was essentially a legalized version of Napster, right? Instead of just downloading the songs for free, let’s take a similar layout and make it look a lot cleaner than Napster did.

[00:07:14] Dan Runcie: And you can download the songs yourself. The thing that’s interesting though, if we just think about Apple’s influence in this space over the years. This was the company that essentially paved the way for digital music technology, listening, both from companies in the industry. And it did the same for podcasting as well.

[00:07:33] Dan Runcie: And for years, Jobs didn’t want to get into music streaming. He thought that having an annual or having a monthly subscription for it wasn’t the best idea. And obviously, we know that podcasting as well. Although it was something that Apple started, we’re looking now, with the way things are, yes, they have presence in both podcasting and of music, but Apple isn’t the industry leader in any of these spaces. So we can have a whole podcast episode about what’s changed, but even though there’s a lot that necessarily maybe hasn’t taken off in the same way. You can’t knock the influence of what this product did in just its evolution over the years and what it led to. I was looking at some stats earlier. Its sales peaked in 2008, 2009, right? You could still, after the iPhone came out, so you had this whole runway of time where they just kept selling more and more and they just eventually figured it out. And they had a whole system of these things that you’re selling 20, 30 billion of them a quarter. It’s crazy. 

[00:08:33] Zack O’Malley Greenburg: Oh yeah. And you know, the deeper you get into the Apple ecosystem, right. I mean, and I’m fully embedded. I’m stuck. There’s no way out. You know, I remember with that, you know, the U2 era iPod, you could still, you know, when you plugged it into your computer, you would still see that little iPod icon on your desktop and you could open it up as though it were, you know, an external hard drive and you could, you know, move files in and out.

[00:08:59] Zack O’Malley Greenburg: And it didn’t really, there were no questions asked as to where the files were obtained, you know, and they would show up in your music library and you can put all kinds of different files on there. And it was great. And then, you know, with each successive version, so they eventually eliminated that. And you know, now of course, if you have iTunes, you know, songs that you may have had in there from the, from the Limewire and Kazaa era just suddenly disappeared.

[00:09:21] Zack O’Malley Greenburg: And, you know, you can’t really get them back unless you have them backed up somewhere on a physical hard drive. So, you know, I think that there was also a level of control that Apple got, but, you know, but to have you be part of that ecosystem, I think that’s the most valuable thing for them, right? I mean, if you look at Apple or Spotify, you know, like you were talking sure, Apple is not the leader in the music streaming business. Apple Music is I guess, a distant second, but they, you know, they don’t need to win that because the hardware turns out or at least in the case of the iPod. And now that, you know, more recently that the iPhone, that the hardware turns out to be more valuable than the software, you know, looking at Spotify.

[00:09:58] Zack O’Malley Greenburg: And I think a lot of it comes down to, you know, intellectual property, right? If the, if you have to pay for the intellectual property or your, you know, or a whole huge chunk of that is coming out of. You know, out of your profits or your revenue before you get to profit, you know, it’s a, it’s a lot harder to make a ton of money than it is for a company like Apple, where the iPod or the iPhone, you know, that was their intellectual property and they could sell it for whatever they want to. 

[00:10:22] Zack O’Malley Greenburg: Yeah, that’s a good point. It makes it even think about AirPods. Now. Now I always see those infographics of AirPod revenue, and comparing that to all of these other tech companies. And how have you just looked at this one product that Apple has and how it does better than so many of the household companies that we have.

[00:10:38] Zack O’Malley Greenburg: But for you though, was the iPod the first product that pushed you onto Apple? Or were you in a household that had iMacs and things like that? 

[00:10:48] Zack O’Malley Greenburg: Yeah, no, I was, my first computer was an Apple, I think I only ever owned one or two computers that were not Apples. And that was when my gaming buddies in high school convinced me to get something else. But yeah, no, it’s been, you know, from back in the day for me. So, I’m stuck. 

[00:11:04] Dan Runcie: Yeah, it’s, it’s interesting because I do think for a lot of people, this product ended up being the game-changer. Yeah. I know it took a few generations for them to eventually put it and make it Windows-compatible. And it’s funny. I was looking back, there was a few conversations where Tony Fadell, the guy who had actually invented it, essentially that worked with Apple on it.

[00:11:26] Dan Runcie: They had had a whole bunch of conversations about what ends up leading to what. And I think for a while, Jobs was under the impression that if you keep the iPod as Apple iOS exclusive device that it’ll encourage more people to buy future iMac or Apple products, but what actually ended up happening, they pushed for the opposite and they saw the opposite where make the device compatible people then see, and they get introduced to the Apple world.

[00:11:55] Dan Runcie: And then that makes them want to then buy more iMacs and buy more MacBooks and buy things like that. So it was the opposite push-pull of what they thought happens. And it’s one of those things where instead of restricting access to make people think that they want, that they, you’re restricting. How do you give people a taste and then have them naturally want to get it on there on their own?

[00:12:16] Zack O’Malley Greenburg: Absolutely. I mean, I think it almost mirrors being an artist, right? I mean, you don’t want to withhold your art, your music from streaming services so that people will go out and buy the vinyl or, or, you know, back in those days, download the MP3. You want people to be out there and getting familiar with your work.

[00:12:32] Zack O’Malley Greenburg: And you’re not going to cannibalize yourself if people really like you. I mean, just look at Taylor Swift, you know, her fans go out and buy her vinyl, you know, by the hundred thousand and they can certainly have access to it whenever they want on the streaming services. 

[00:12:44] Dan Runcie: Yeah. Speaking of vinyls, it stuck out to me that there were a bunch of iPod Touch that sold out immediately.

[00:12:51] Dan Runcie: So essentially the line is completely gone now and even a few on eBay that were going for crazy prices after this announcement came out and it made me think, is the iPod going to be the way that vinyls are looked at now? Is there going to be this resurgence for this retro thing where people look back and let’s say that as millennials or gen Z have, kids, they want to see, okay, what was this generation listening to when they were teenagers and they’d go back and be like, oh, let’s check out Zack’s iPod, let’s check out Dan’s iPod or whatever else. Do you think that there is a resurgence in that type of way the same way we’re seeing with vinyl? 

[00:13:26] Zack O’Malley Greenburg: You know, I could see maybe I think the main issue would be a compatibility, right? In the way that you, you know, not even Apple to PC, but you know, old Apple stuff isn’t even necessarily compatible with, compatible with new Apple stuff.

[00:13:37] Zack O’Malley Greenburg: So if I wanted to plug in my old iPod, if I could dig it up wherever it was. I don’t think I even have a freaking USB port on my computer. No, I don’t. 

[00:13:49] Dan Runcie: You need like five dongles. You need like a firewire, USB to USB to C. 

[00:13:54] Zack O’Malley Greenburg: Exactly. And so, and even then it’s like what songs will it remove, will my computer remove from my iPod or vice versa?

[00:14:04] Zack O’Malley Greenburg: So, I mean, I almost wonder if there’s the really old ones where you go and you can see, like you can open it up like that U2 era iPod, and actually just manually move the MP3 tracks around, if those still work somehow, you know, that might be almost the way of safeguarding one’s music files from being kinda like yanked up into the ether.

[00:14:22] Zack O’Malley Greenburg: You know, I think whereas, vinyl, despite being somewhat cumbersome, it is ultimately plug and play. You plug it into a standard outlet, put the thing on pretty mechanical. So yeah, I do think that might be the only drawback, but yeah, I could totally see it. The next hipster thing, being dongles at all, finding the way to use iPod. So, yeah, just, I guess cassette tapes are making it come back to, so, you know, just like vinyl, even CDs were up, you know, over the past year or so.

[00:14:46] Zack O’Malley Greenburg: What’s old is new again. 

[00:14:48] Dan Runcie: I know, right? You never know if someone had told me when the iPod first came out, that vinyls would’ve made a comeback, I’d never would have thought that, but you mentioned plug and play and you mentioned U2 earlier. We have to talk about the greatest hack of all time with whatever you plug this damn device into any USB thing, U2’s album automatically starts playing.

[00:15:07] Dan Runcie: How they were able to get that to happen and I know it wasn’t a hundred percent intended, but it also kind of was so however they were able to do that, eventually I do think it got on the nerves of many people and we saw from whether it was Apple or even Spotify later on people feeling like these services are pushing certain artists on them.

[00:15:27] Dan Runcie: I do think that that is one of the understated hacks that we’ve seen in both of U2’s major deals with Apple. 

[00:15:36] Zack O’Malley Greenburg: Yeah, for sure. I mean, I just remember, you know, right. They gave away that album and you woke up one morning and it was on your iTunes and all these people were freaking out, like, get this off my computer.

[00:15:45] Zack O’Malley Greenburg: I can’t get it off my computer. I don’t want this taking up hard drive space. Like first of all, how much hard drive space is taken up? You have a Mac anyway, probably. And it’s, you know, it’s fine. Is Bono really that offensive to you? Like U2? I mean, I don’t know. I think it’s sort of, you know, I mean, I don’t want to say like easy listening, but it’s not like offensive, like who is offended by U2?

[00:16:06] Zack O’Malley Greenburg: I was kind of always surprised by that. And Bono had this kind of poignant quote. He said he was like, you know, “I’m just an Irishman trying to give you some beautiful music.” Yeah. If you don’t want it, I’m sorry, you know. That kind of thing and can’t really feel bad for Bono and he was a good sport about it, but it’s kind of funny that the way people’s minds work, you know, it’s like during the Napster era, it’s like, oh, I got to go get all my music for free.

[00:16:33] Zack O’Malley Greenburg: You know, I will seek it out to illegally download music. Right. And it’ll take me an hour to download a song. And if somebody calls my mom on the landline, you know, it’ll get interrupted halfway through, right? And then. Here comes U2 giving everybody a free album and they don’t even have to do anything.

[00:16:51] Zack O’Malley Greenburg: And all these people are kind of grousing about it. So I thought that was sort of, you know, above all a really interesting commentary on like the human psyche and, you know, wanting what you can’t have. Not wanting what you do. So pour one out for that as well. 

[00:17:05] Dan Runcie: Oh yeah. I mean, it’s interesting because I mean, from my perspective, I was never upset about the album actually being there, if anything, it was more so than minor inconvenience of can I plug this device into the USB port for one second, without anything automatically playing, right? Like I also had this era where it was back from doing anything that I’d purchased on iTunes and Lady Gaga’s Bad Romance would always play. So like once the U2 thing stopped, like that song always played in.

[00:17:35] Dan Runcie: You want to hear about friends making fun of me and dragging me for that all day long. That was always a, a hilarious one, but no, this was good. Let’s pour one out for the iPod, one of the most influential products we’ve seen. And as we both know, I think we talk about how so much innovation starts in music and this device is one of the best examples of that.

[00:17:55] Dan Runcie: So salute to it. It had a, had a great run. And on that note, I actually think it’s probably better for us to stay on the music topic and the streaming topic. And talk a bit about Spotify because this company, less than a year ago, well, maybe a little bit more than a year ago, they were signing so many of the big exclusive deals.

[00:18:18] Dan Runcie: The Rogan deal was still fairly fresh and the stock was at an all-time high. And now this stock is at an all-time low, as of recording this, it’s trading under a hundred dollars. Its market cap is under $20 billion. Daniel Ek just purchased 50 million himself to show confidence that he has in the company stock moving forward.

[00:18:39] Dan Runcie: But where do you see all of this happening? I think there’s a lot that’s happening in the market right now that could be aligned with this, but there’s a lot that could be separate from this. That could be a bit more specific to where Spotify currently is. What’s your take on the current state of Spotify?

[00:18:55] Zack O’Malley Greenburg: Yeah. I mean, I think, like you say, there are these kinds of macro trends in the market, in the world that are kind of dragging down a lot of stuff. I think with Spotify though, what’s going on is that people are freaking out about streaming in particular after that sort of big surprise, bad news from Netflix a little while ago, where they essentially admitted that the cap on, you know, paid streaming for them was 220 million people and that they were going to open up their free, you know, free or lower ad-supported tier. I forget if it was free tier with ads. I think it was just a lower price tier with ads. So yeah know the idea that, well, you know, it’s all streaming and Spotify had been trying to emulate Netflix by paying all this money for content and you know, the Joe Rogan’s of the world and podcasting and stuff.

[00:19:40] Zack O’Malley Greenburg: So I get it on one hand, but, you know, there’s a lot of fear right now in the public markets. And there’s a lot of, sort of, you know, constellating of things, right. And yes, they’re both streaming companies, but to me, you know, I take a step back and I look at it and I see two totally different companies. I mean, obviously one is primarily, you know, video, one’s audio, but you know, the reason that Spotify works and the reason that Spotify became the market leader in audio streaming, it is essentially an unlimited buffet.

[00:20:09] Zack O’Malley Greenburg: Netflix was never an unlimited buffet. And you know, this, if you are somebody who has ever gone on Netflix to find a particular movie or something like I remember many years ago when I first got Netflix, I was like, oh, you know, I want to watch whatever it was. The latest James Bond movie. I’ll go on here. It’s like $9.99 a month, unlimited everything, right? No, they only have, you know, whatever move they have, all these Adam Sandler movies and they have, you know, just like a random smattering of movies. And of course they have all these shows, but you get Netflix because you want to watch certain shows, you know, or because you are somebody who’s just like, I want to just put something on and I trust that they will have, yeah, I don’t want to think about it. Like I trust that they will have good stuff and I’ll put on one of their shows and you know, it’s not cheaper than cable. So, you know, that to me was always a very different model. It is not an unlimited buffet of movies and television, you know, unlike terrestrial cable, where in theory, you know, you get your cable package.

[00:21:06] Zack O’Malley Greenburg: You can watch the news or you can watch sports. So you can, there’s some crappy movies on, you know, there’s like more of a promise of unlimited opportunity. So I think that, like, there was never a video streaming service that had the unlimited buffet kind of nature of Spotify. So, you know, I think that’s what ultimately caps Netflix, like around that 220 million number. If there was some way that Netflix could totally replace your cable. And I know Hulu has live TV options, or if Netflix really did have, you know, a complete movie library that you could complete TV library, you can, anything you want. I think that there would be a lot more room to grow, but it’s such an ordeal to get all the rights necessary to do that.

[00:21:46] Zack O’Malley Greenburg: I don’t know how that would ever happen. And you certainly couldn’t bankroll like every single thing in the future. That would be needed to have that kind of thing going on in perpetuity. So, yeah, I guess I just, I think that Netflix is dealing with this issue of like, sort of the unbundling and re-bundling and what people are treating Netflix as a sort of like a bundle, right? You want to maybe some other bundles, you probably don’t just have Netflix, you have Netflix and Hulu, or maybe you even have terrestrial cable and Netflix or something like that. Whereas the Spotify, you have all of your music. I mean, what do you not get on Spotify? Or if it’s Apple Music, what do you not get an Apple Music?

[00:22:18] Zack O’Malley Greenburg: So I think it’s a little bit of the baby getting thrown out with the bathwater. And I just think that the fundamental thesis is a little bit different when it comes to Spotify than it is with Netflix. So that’s my 2 cents. 

[00:22:29] Dan Runcie: Let’s take a quick break to hear a word from this week’s sponsor. 

[00:22:30] Dan Runcie: Yeah, I think that’s fair. And I think that echoes what Daniel Ek had said himself. Right. He said, even though Spotify and Netflix are both subscription-based revenue companies that serve media on a regular basis to its content, that is where a lot of the similarities do stop. And even though there are points where I feel like Spotify and other streaming services, music streaming services, tried to replicate what Netflix did.

[00:22:55] Dan Runcie: It was never going to be that way. And I think what makes the music streaming area a bit more unique is that because 80%, I’ll probably even say 90% of the content that each of these services offer is largely the same. You end up inevitably having a price war at some point, once you’ve reached a certain level of distribution, and once you’ve reached a certain percentage of audience that you’re reshaped, we’re starting to see that happen.

[00:23:20] Dan Runcie: Now you’re starting to see that saturation. And I was recently talking to Will Page, the economist that studies this space. And his analogy was that for a long time, this was a herbivore market. People were capturing the opportunity that’s there, we’re shifting to a carnivore market, and in a lot of ways that does end up benefiting the companies that are the most willing to cut costs and the most willing to pivot. And if we’re bringing things back full circle a bit to what we said about Apple Music earlier, this is not a product that they are necessarily trying to run at a profit. It’s very similar to the Amazon Prime mentality of when Jeff Bezos has said, the more Golden Globes that we win, the more sneakers that we’re able to sell through Amazon.

[00:24:03] Dan Runcie: And I think the same could be said for Apple to some extent. They won best picture, CODA won best picture. That’s their product that helps them get more subscribers who then end up purchasing the wide number of different products they have under their Apple TV+ bundle that they’re able to offer there.

[00:24:19] Dan Runcie: I do think with Spotify though, and this is why I do think they likely have more relative upside right now, I would say than Netflix, it’s for two reasons. One, Spotify has had relatively better growth in the most recent quarters, I’d say, and that’s even accounting for both services are ceasing their service in Russia.

[00:24:37] Dan Runcie: It’s also looking at them just being able to already have the free tier penetration, already having a pipeline to acquire more as well. And secondly, I think the podcasting model is ultimately what will help them. This was a model that I was initially skeptical about for years, just in terms of whether or not Spotify would be able to actually make it work and become the dominant player in audio.

[00:25:01] Dan Runcie: But the reason that I think they’re probably going to be better off is because of the actual data that they could offer both advertisers and listening and podcasters as well. And this is going back to opportunities that Apple didn’t necessarily capture at the time, if you think about the fact that most podcasting is essentially just an RSS feed and a lot of people are sharing monthly podcast downloads and things like that.

[00:25:25] Dan Runcie: And if you look at some of the podcasts, especially some of the ones that were most popular, 2016 when podcasts would really start to take off. A lot of those listeners may not necessarily be actively listening, like it could be background downloads. That’s where Spotify wins, because they can actually have that clear data to show who’s listening to what. They acquired two companies, Chartable and Podsights, that are both analyzing and having the better data in this space. So the, we’re leading to a future where Spotify eventually is going to be able to, I think, dominate the space because they’re able to make the better pitch to advertisers. Come here, get a more direct way to reach your audience.

[00:26:03] Dan Runcie: And I think if the numbers do continue to grow, I think they will be better off. So of course this is not investment advice, to be clear for anyone. But I do think that between the two of these, that Spotify is probably the company that’s in the better position. And it’s funny cause this isn’t always a, a thought that I would have had of course, two completely different business models.

[00:26:22] Dan Runcie: Netflix is fixed. Spotify is variable, but I do think that over time, relatively speaking, it still has plenty of hurdles to get through, but it feels like that’s where the opportunity is. 

[00:26:34] Zack O’Malley Greenburg: Yeah, absolutely. I think I totally agree with you there. 

[00:26:36] Dan Runcie: Yeah. And I mean, with that, another piece that people have brought up as well as content as well. What are your thoughts on Netflix’s content? Because I know that’s a piece where people have often said, well, if you’re just going to make shows, like, Is It Cake? and stuff like that, then why am I going to pay money for the service and the fact that they haven’t necessarily had as many true franchises or any repeatable types of things.

[00:27:00] Dan Runcie: In my opinion, a lot of the things that have taken off from Spotify have, or not from Spotify, from Netflix. Sometimes it almost feels like it’s like flashes and bottles that catch off a bit unexpectedly, whether it’s like a Bird Box or a Squid Game, or Making A Murderer, things like that. Like it doesn’t have the same feeling of, okay, you don’t, this big HBO show is going to come and dominate like it does.

[00:27:23] Zack O’Malley Greenburg: Yeah, you know, I mean, I think Netflix has just done such a good job of going out and just acquiring tons and tons of content. Right. And, you know, given their model, they pay out a lot, you know, then people have been talking over the past, however many years, like, oh, Netflix spent X billion dollars on content.

[00:27:41] Zack O’Malley Greenburg: How are they going to sustain it? But when you’re acquiring that much stuff, it’s like, you have all these lotto tickets and when something takes off, you know, I think in most cases you’re not having to pay a lot of it back, you know, on the backend like you would with, you know, obviously Spotify ends up paying back, you know, a huge percentage of what comes in back to the labels and to the artists.

[00:28:01] Zack O’Malley Greenburg: So I think that the model. Netflix, has there are sort of like a lot higher upside when something works? I mean, I guess with Spotify, they’re trying to emulate that on the podcasting side, but you know, it would seem to me that when Netflix has, you know, a TV show that takes off just out of nowhere, I mean, something like Squid Game, the amount of new subscribers they sign up are just, you know, so much more than, than you’d get with a hit podcast. So, I mean, you know, in a way I think what I’m most curious to see is how much will Spotify continue to try to emulate Netflix. Now that Netflix is sort of in a, you know, questionable phase and do they just kind of, you know, try to double down on the music aspect because the other piece of it that we haven’t talked about, you know, when you’re going out and acquiring content and you were paying for it specifically like to have it named and everything you become, you know, an arbiter of culture and taste also, you know, right and wrong of what is hate speech of what is, you know, all kinds of things. And that’s like a huge pain in the ass to figure out, right, as we learned with the whole Spotify, Joe Rogan, Neil young situation.

[00:29:06] Zack O’Malley Greenburg: And. Yeah. I never thought that Neil Young being off of Spotify was gonna ruin Spotify. And I don’t really think very many people did, but you know, it did go to show that there’s a, an amount of energy that has to go into defending some decisions once, once you are acquiring content versus sure, I mean, if you have artists on your platform and you know, they do something terrible, you may have to make a decision to try to pull them off. But, you know, I think generally as a society, we’ve moved away from pressuring people to sort of deplatform musicians for making, you know, offensive music or something like that, music that some people find offensive.

[00:29:42] Zack O’Malley Greenburg: And even for, you know, some of the most controversial musicians, you know, it’s super rare that their music is pulled down. So I just think that there’s a lot more editorial energy that goes into obviously Netflix, but, you know, Spotify emulating Netflix in the podcasting space, that becomes a whole new headache with like a lot of unknown unknowns.

[00:29:58] Zack O’Malley Greenburg: So I do wonder now that it’s, you know, perhaps less of a growth area. Will Spotify continue to follow that path? 

[00:30:04] Dan Runcie: Yeah. That’s a great point. We had not touched on this piece of it. And I think that in a lot of ways it does mean it’s more workforce, something like a company like Spotify. Netflix can pretty easily, at least I would hope so, identify the movies that have these issues, and we’ve already seen some of them have disclaimers, but there’s a bit of a removedness from it because of just how they go about their deals versus Spotify. You just see the blind spots where someone that literally goes and finds all of the clips of Joe Rogan saying the N-word, putting that together.

[00:30:38] Dan Runcie: And then that’s what sparks the controversy. You would have hoped that the company themselves would have been looking at the content. And then it makes you think, are people really responding to the issue itself? By people, I mean, the company like Spotify, are they really responding to the issue itself or are they responding to the public outcry over the issue?

[00:30:54] Dan Runcie: And that could, you know, be an ongoing conversation, but that’s where I do think that there needs to be much more editorial oversight and understanding that if you are going to be, it’s one thing to say that you’re an open platform that anyone can put music on. Anyone can put, upload their music too, but when you’re exclusively paying someone or licensing their content, it changes the dynamic of the relationship.

[00:31:18] Dan Runcie: And I know that they try to make the distinction. Yes. we are licensing Joe Rogan’s content as opposed to acquiring it. But the example I always bring back to people it’s like, okay, well, let’s explore that scenario then, let’s say that this was Bill Simmons, who now works for Spotify because you acquired his company and we found those clips of him saying those things. Would you then have treated this situation differently? I don’t know the answer to that situation, but Spotify is implying that they would, but I don’t know. 

[00:31:47] Zack O’Malley Greenburg: Yeah. It’s a gray area. And the more you get into, the deeper you get into editorial, the less profitable it is, I say, as a journalist.

[00:31:54] Zack O’Malley Greenburg: So I think that, you know, some of these companies are learning that the hard way. 

[00:31:58] Dan Runcie: Couldn’t agree more. And while we’re on the note of Spotify, let’s switch gears again and let’s talk about the current king of Spotify, right? Bad Bunny. It is been really cool, and refreshing to see an artist outside of the US dominate on a platform like this.

[00:32:13] Dan Runcie: I think that his success has really shown what’s possible now in a way, I think that he’s the greatest success story of the streaming era. I really do. I mean, when you think about what he was able to do, where he was six years ago, I’ve written about it in a recent newsletter about how six years ago, he’s bagging groceries at a local grocery store in Puerto Rico.

[00:32:36] Dan Runcie: And then now he’s a superstar. He was on stage at the Super Bowl. He’s going to have this old Marvel movie, tops every chart possible. It’s like that Kurt Warner underdog story from him starting off as a grocery bagger and then did his Arena Football. But imagine if Kurt Warner had the career of Peyton Manning and actually went on to, you know, dominate years and years, it’s impressive. What do you think about Bad Bunny and what he’s been able to do? 

[00:33:00] Zack O’Malley Greenburg: Ah, I think it’s incredible. I mean, and I think it also, it shows the democratization that has been brought about by streaming and what’s that Jay-Z line? Men lie, women lie, numbers don’t. And you know, you can have your charts for whatever publication and you can have all this and that and their formulas and stuff like that.

[00:33:18] Zack O’Malley Greenburg: But, you know, it’s all very convoluted and, you know, it’s, it’s usually one way or the other. It’s engineered to sort of favor the, those who are already sort of big names, but when you have the numbers, it shows up on Spotify and regardless of where you are on whatever other chart, I mean, the fact is that more people are listening to your music than they’re listening to anybody else’s music and it’s objectively true. You can see it in Spotify and the numbers don’t lie. And so Bad Bunny, I think, you know, was able to come up from, you know, in this incredible underdog story, you know, to get there and there’s proof, right? I mean, there’s proof in a way that there might not have been, you know, before the streaming era.

[00:33:56] Zack O’Malley Greenburg: So I think another thing about Bad Bunny that, you know, certainly in my time at Forbes, we would look, we’ve scoured the world to find and do our list of the top-earning musicians. And I did that list this past year for Rolling Stone, but, you know, it was just all old rockers selling their catalogs basically.

[00:34:14] Zack O’Malley Greenburg: And I think, you know, a function of that is that the pandemic has just greatly disrupted touring, which would kind of like traditionally be the thing that would get you up on one of these lists. And, you know, I think now that the pandemic is kind of easing up and tours are really starting to happen again, you know, we’re seeing Bad Bunny be able to sell out stadiums, you know, I mean, he is really on that level in terms of, you know, people putting their money where their mouth is. So I think that next step is going to be, as we start to see these totals from his tour in combination, you know, with the streaming dollars and Marvel and all these other things that are going to come along with it, you know, he’s going to start to climb up these earnings lists, you know, from a financial perspective as well.

[00:34:56] Zack O’Malley Greenburg: So I think that adds a whole other level. You know, sort of like credibility in some cases, when looking at somebody as like a generational superstar, when they sort of have the, you know, the financial success to prove it and to sustain and to, you know, to expand into other fascinating ways. So I’m really curious to see what he does next.

[00:35:16] Zack O’Malley Greenburg: Like, you know, what’s his Jay-Z move? What’s his Puffy move? Is there going to be something in the spirits business or the cannabis or who knows what, but, you know, personally, as sort of a music business nerd, I’m especially interested to see, you know, what does he do with all this energy and momentum and you know, what direction does he take it in having created this incredible musical empire.

[00:35:36] Dan Runcie: Yeah, it’s only a matter of time until he’s going to top most of those lists, right? You look at the numbers that this tour will likely do. It’s likely going to be over 2 or 3 million, if not more, just given the amount of shows that he has and the size of the arenas that he’s performing in. And one of the things that I’ve always thought about with artists from other countries is that there’s always been this stigma or thought that in order for them to monetize, it always had to rely much more on brand deals or things like that because the assumption was that the fan bases in these areas may not be willing to necessarily pay as much, but his tours are disproving that just based on the sales numbers, I would need to dig it a little bit further to see, okay, are the dollar amounts in all of the regions similar, but I think he’s proving that that isn’t necessarily the case. Yeah. If he does want to continue to take this further, what would it look like if he eventually let’s say that he continues to do things with the WWE even further? Is he able to have some type of connection there to make that further extend, right? This Marvel character he’s going to have in this upcoming movie is a wrestler. What could that potentially look like? If he ends up selling some type of, as you mentioned, some type of spirits or getting involved with something on the business side, the sky really is the limit.

[00:36:52] Dan Runcie: And I think it’s one of those unique optionality things where it’s up to him and what stuck out to me as well as if we think, just think about his trajectory and what’s possible now for a lot of Latin artists, is that he has not done one song in English. Everything that he’s done is either been in Spanish or if he did it, then his verses is still in Spanish.

[00:37:15] Dan Runcie: But everyone else is still doing their stuff in English. Like this song. Cardi B from a couple of years ago. But I do think that that’s different from even the wave of Latin artists that got mainstream popularity. Let’s say 20 years ago, you have Enrique Iglesias, your Mark Anthony or even JLo to some extent, they all had to do albums in English before they were ever given a consideration for that mainstream push or appeal.

[00:37:41] Dan Runcie: Ricky Martin was the same exact way. And I think the fact that he’s been able to do on his terms, he’s been able to be an advocate as well for both gender norms and for just LGBTQ as well and how he has been just a lot of the causes and things that he cares about. It’s really cool to see artists like this.

[00:38:02] Dan Runcie: And I think in some ways the trajectory that Latin artists have been on, especially in the streaming era, kind of reminds me of where hip hop was at a certain point, right? It’s like in the early days they wanted those artists to like assimilate to whatever the pop phase was, right? Like the rappers had to do these pop collaborations.

[00:38:21] Dan Runcie: The Latin stars had to do the, you know, US pop star collaborations. Then once they prove they no longer have to assimilate in the same way, then those artists set the trends and now everyone else wants to come to them. And now we’re seeing Billie Eilish and Drake and all these other artists doing songs in Spanish, even though that’s not their main language, we’re just going to see more and more of that.

[00:38:42] Zack O’Malley Greenburg: Yeah, I mean, and I think that one of the things that Bad Bunny has proven, you know, in some other form, is that if given the opportunity, you know, if you’re not sort of, you know, forced to go meet the quote unquote US mainstream market, where it’s at, the US mainstream market will actually come to you. You know, and people who don’t understand Spanish will still love your music.

[00:39:02] Zack O’Malley Greenburg: And, you know, I mean, I don’t know. I know a lot of songs in English that I don’t understand. Whatever genre, if it’s, you know, rock and there’s a lot of yelling or if it’s, you know, rap and it’s like so fast or with like a really deep accent. I don’t always catch on but, you know, people respond to music. I mean, it doesn’t really matter what’s being said, I mean, look at Nirvana, right? Like a lot of the lyrics didn’t particularly mean anything, but people just responded to the music and the vibe, the whole thing. So even if you can understand the words, people are going to be attracted to the music. And, you know, I think that he’s showing that that holds true even on the tip-top superstar level for sure.

[00:39:38] Dan Runcie: A hundred percent. Excited to see where his career goes, excited to see where he continues to dominate. 

[00:39:43] Zack O’Malley Greenburg: Amen to that. And, you know, if have his management too, I’m trying to get him in some consumer-facing startups, because if you’re a startup and you’re looking for celebrity investors and they know that the market is cooled down at it, but still, you know, you’re in a really mature startup. And you’re trying to get your name out there a little more by getting, you know, music, investors, celebrities, et cetera. The kind of reach that has, especially if you’re trying to get into Spanish language market. It’s untoppable. And I just think there’s a tremendous opportunity there and in a lot of other places for him too, so. 

[00:40:12] Dan Runcie: Oh, yeah, I’m sure. It should be. All right. Before we wrap this up, we got to talk about this article that you had written very recently about, we’re both fellow Yankees fans, and one of the stars we’ve been most familiar with over the years, Robinson Canó, and you have this idea that you were brought up. I thought it was really interesting and I want for you to talk more. Did Jay-Z ruin Robinson Canó bag? 

[00:40:40] Zack O’Malley Greenburg: Yeah. Yeah. I mean, so I kind of posed that question on my Substack and, you know, I think going into it and that the background,I’m going to set the background for anybody who maybe isn’t a Yankee fan, but I guess it was eight years ago, Robinson Canó, who at the time was the best player in the Yankees.

[00:40:57] Zack O’Malley Greenburg: Everybody thought he was going to resign. He was a free agent. Everybody thought he would come back, think they he’s never lose out on a free agent. Jay-Z comes in, takes over as his agent from Scott Boras, who was like, you know, he is to baseball agency as Jay-Z is to hip hop. Jay-Z comes in, gets Canó to come over to Roc Nation, Roc Nation brings on CAA to help them, you know, kind of become, you know, Scott Boras-level players in the game, let’s say, and you know, Robinson Canó gets offered seven years, $161 million by the Yankees and the months drag on, nobody else is offering him more. Everybody thinks Jay-Z is getting greedy.

[00:41:34] Zack O’Malley Greenburg: And then just out of nowhere, Canó goes to the Mariners for 240 million over 10 years and great deal financially for him. Obviously, it’s, you know, like $80 million more than Yankees we’re offering and no state income tax in Washington. However, a much worse team, a much worse ballpark for hitters and, you know, five years into the 10-year deal could no, I mean, I think that was when he got suspended for steroids, then he got traded to the Mets.

[00:42:03] Zack O’Malley Greenburg: And then he got suspended again last year, 80 games. And he started out this year with the Mets and just earlier this week got cut. And so here’s this guy who, you know, so I guess that’s my question. If he’d stayed with the Yankees, would all of, all of these miseries have befallen him and should we blame Jay-Z for the misery?

[00:42:22] Zack O’Malley Greenburg: And I think my answer ultimately is, is no, you know, It’s going to retire almost a hundred million dollars richer, eventually. From a baseball perspective though, you can argue that things would have been better for him if he’d stayed with the Yankees. And as it turns out, the guy who really kind of led the charge and I reported this in the latest edition of my Jay-Z book, Empire State of Mind, the guy who led the charge for Canó to leave was Brodie Van Wagenen at CAA who then became the GM of the Mets. Traded for Canó, got fired by the new owner of the Mets and is now back working with Jay-Z. And I think working on, on representing Canó again, as he tries to, to latch on with another major league team.

[00:43:00] Zack O’Malley Greenburg: So you could kind of blame him, but you know, at the end of the day, I think it really does come down to the player, you know, who makes the decision to take bag, you know, instead of glory, which is, you know, defensible, I think you’ve got to live and you only have so long to be a professional ballplayer. And, you know, he was the one that took the performance-enhancing drugs, got suspended so, but it is this just sort of like a fascinating winding road, you know, from this decision that happened eight years ago, that’s still playing out, that still had all these ramifications. And you look back to that deal. I mean, you know, the fact that Jay-Z, whether it was Jay-Z or CAA, or this guy, Brodie Van Wagenen doing most of the work.

[00:43:37] Zack O’Malley Greenburg: Jay-Z, Roc Nation did get credit. And after that you saw Roc Nation really become much more of a force as a professional sports agency. So, you know, certainly, Jay-Z did well for himself in those past eight years. He’s a billionaire now. Brodie Van Wagenen has this great new job, and Robinson Canó has that much nicer retirement eventually.

[00:43:58] Zack O’Malley Greenburg: So maybe he lost a chance at eternal glory, but you know, a hundred million dollars is a lot of money. I don’t know. Dan, what do you think? 

[00:44:04] Dan Runcie: It’s interesting because I’ve always thought that his career was definitely into replay. I felt like it was typical timing of, okay, this guy’s turning 30 and that could be hit or miss for a lot of baseball players, depending on how well they’re able to take care of themselves and stay out of injury thing.

[00:44:18] Dan Runcie: The one thing though, and this is a part that I do think gets overlooked sometimes is the ballpark difference. Yankee Stadium, especially in the new Yankee stadium, literally engineered in some ways to get more home runs and just have more, especially more than the old Yankee stadium compared to T-Mobile Park in Seattle, before it was Safeco park, historically picture friendly ballpark.

[00:44:41] Dan Runcie: So if you know what you’re getting yourself into, I mean, outside of Griffey and A-Rod in the nineties. I can’t necessarily think of people that really like, oh yeah. You know, they cleaned up there. Maybe, you know, you had some early, I’m trying to think of some of the other stars who may have like, done well they’re from like a home run hitting perspective, but it’s one of those things where you think about the trade-off, right? It’s. to some degree, it kind of makes me think about Carmelo Anthony with the Knicks, right? It’s like you went to that team, you did get paid and you ended up getting, you know, later on a Supermax. But I think a lot of the decisions that he made show that he was prioritizing more of the money that came through, as opposed to the decisions, why not wait until free agency to then join that team instead of making them all those picks for you. 

[00:45:30] Zack O’Malley Greenburg: Exactly.

[00:45:31] Dan Runcie: And in some ways, yeah, I think about the Canó thing, that kinda kind of similarly, right. If you want it to continue to win and you didn’t care as much about the money that you would have stayed in New York, but to our point, yeah. You get it a hundred million dollars is a lot, of course, but it’s hard to have both, especially with the franchise, in my opinion, that they’ll have spurts of having great players here and there, but they haven’t necessarily been able to prove that winning this, that Canó was raised in.

[00:45:57] Zack O’Malley Greenburg: Yeah, and Canó is going to finish up and, you know, even now it looks like he may, he’s probably going to catch on with another team, at least for the rest of the year, but he’s, I think at 2,600, a little over 2,600 hits for his career, if he had been able to get to 3000, which I think in New York with a better lineup that turned over more, he gets more best, more opportunities to hit.

[00:46:16] Zack O’Malley Greenburg: There ‘s a better ballpark for hitters. So more fly balls turn into home runs. It’s pretty likely, he would’ve gotten to 3000 hits or that he’d be within shouting distance of it. Now with, you know, a little more time to go. There has never been a major league baseball player who got 3000 hits who did not end up in the hall of fame once eligible, except for the steroid guys and Pete Rose, who was thrown out of the game for betting on baseball. So it is like an automatic ticket to the hall of fame. So if he had just stayed at Yankee stadium, not done, you know, not on steroids, I think he would have gotten there. No question. And you know, who knows, I mean, seven years into that deal that he would have been what, 37, maybe. You never know if he was still hitting well, they might’ve brought him back for another year or two. God knows they kept bringing Brett Gardner back. So I do think he would’ve gotten a few thousand hits and had a really good shot at the hall of fame. And is that worth a hundred million dollars though?

[00:47:16] Zack O’Malley Greenburg: Yeah, I don’t know. Probably not. Probably not. He did have such a sweet swing though, man. Watching him play in the Yankees stadium. That was always fun. 

[00:47:25] Dan Runcie: He did it. He was exciting to watch. He had a great career and yeah, I think that’s a great note for us to close out with this. Zack, we’ve covered a bunch in this pod, but basically, we’ll have to have another roundup again at some point soon, but thanks for doing this. This is fun.

[00:47:38] Zack O’Malley Greenburg: For sure. Thanks as always.

[00:47:41] Dan Runcie: If you enjoyed this podcast, go ahead and share it with a friend. Copy the link, text it to a friend, post in your group chat, post in your Slack groups, wherever you and your people talk, spread the word. That’s how Trapital continues to grow and continues to reach the right people.

[00:47:56] Dan Runcie: And while you’re at it, if you use Apple Podcast, go ahead, rate the podcast, give it a high rating and leave a review. Tell people why you like the podcast. That helps more people discover the show. Thank you in advance. Talk to you next week.

Dan Runcie

Dan Runcie

Founder of Trapital

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