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Zack O’Malley Greenburg on How Music Leads Innovation, Forbes to Substack, and Hip-Hop’s Next Billionaire

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Former Forbes senior entertainment editor Zack O’Malley Greenburg returns to the podcast to talk about his achievements when he worked for the media company. He shares his thoughts on Jay-Z, the challenges of publishing, and why he decided to go with Substack. He also discusses his books, “We Are All Musicians Now” and “A-List Angels”, diving deep into some of the different themes and artists that he wrote about. 

If you’re interested in seeing things from a music and entertainment writer’s perspective, this is the episode for you!

Episode Highlights:

[03:05] On pioneering Forbes’ hip-hop coverage 

[08:22] How Zack valuates the net worth of hip-hop artists

[11:25] Jay-Z’s billionaire status and his future plans

[17:32] About Zack’s transition to Substack

[23:38] Forbes’ journalism style versus Zack’s writing style

[25:25] A preview of “We Are All Musicians Now”

[34:35] What “A-List Angels” is about

[39:12] Zack’s prediction on who is going to be the next billionaire

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Host: Dan Runcie, @RuncieDan, trapital.co

Guest: Zack O’Malley Greenburg, @zogblog, Zack O’Malley Greenburg

 

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Transcript

Dan: Hey, welcome to the Trapital Podcast. I’m your host and the founder Trapital, Dan Runcie.

 

Today’s guest is Zack O’Malley Greenburg who is the author of We Are All Musicians Now, which is a book that explores how musicians have led the way and influenced many of the trends that we now see in tech, media, entertainment, and elsewhere in society.

 

Zack is releasing this book independently through Substack which is a career change from what he had been doing before. Zack is most known by many people for a lot of the entertainment work that he did at Forbes. He was a senior entertainment editor there and he led and created so much of the hip hop and entertainment coverage that is now a staple for Forbes and what people see as Forbes’s influence in culture and society now.

 

Think about all the times that hip hop artists are name dropping Forbes lists or talking about where they stack up, where they rank, Zack was the one that was the catalyst for so much of that work.

 

So much of the status and influence that Forbes has in that role, Zack was the one that was interviewing many of these artists, he’s the one that had led so much of the work that went into the numbers like naming Jay-Z a billionaire, naming Kanye West a billionaire and we’ve seen that continued with some of the announcement they’ve made recently with folks like Tyler Perry or with Rihanna and other entertainers and celebrities that have hit that billionaire status.

 

On that note, Zack and I also talked about some of the ridiculous celebrity net worth calculations that are out there and how they appear in the first place and then we made our own predictions on who we think will be the next billionaires to come through hip hop.

Here’s my conversation with Zack O’Malley Greenburg.

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Interview

 

Dan: So we got my guy, Zack O’Malley Greenburg, back on the podcast. He’s the author of We Are All Musicians. Zack, first off, welcome back. Not too many repeat guests so, you know, I’m glad you can make it happen and it’s always great to talk to people again.

 

And for you, specifically, I mean, you’ve definitely made a few changes since we talked last time, but I feel like now is a good time to sit back and reflect on so much that you had done and accomplished at Forbes.

 

I think Forbes, in so many ways, is now known almost primarily in a lot of people’s eyes for the depth of its entertainment coverage and so much of that started with you so it’d be great to hear like what that journey was like and what it was like building that out over 15 plus years.

 

Zack: Well, thanks, man, and great to be back here. Yeah, you know, so I made the jump over to Substack a little while ago but, you know, I think that the Forbes thing was, you know, it started out — and I should say, the Substack thing is both my kind of weekly writing and I’m also serializing the book, as you mentioned, We Are All Musicians Now. So that’s all over on Substack.

 

But, you know, Forbes, for me, it started when I was an intern in my college years. I mean, I got like a note I saw on the college newspaper bulletin board and it said interns wanted and, you know, I applied and I got the gig and basically spent so long there, I realized that my career at Forbes was old enough to drive.

 

So I thought it might be time for a change, but we can get into that a little later but, yeah, I mean, you know, it started out that first summer I was at Forbes, you know, an editor came into my cubicle and she said, “You’re under 30, do you like hip hop?” and I said, “I love hip hop,” and she’s like, “I want you to help me create the first ever list of the top-earning rappers,” and I was like done, let’s do it.

 

And, you know, shortly thereafter, fast forward, I’m driving through the desert reporting some other story and on the radio comes the song, it’s like, “I get money, I get money, Forbes, 1, 2, 3,” and I was like, “Whoa, what’s going on here?” and it was 50, Jay, and Puff had all hopped on that 50 song and done this remix, the billionaire Forbes 1, 2, 3 remix.

 

And, you know, that was back in, I believe it was 2007, and I got back to New York and all the editors were like, “I think you’re onto something here.”

 

So, shortly after that, the editor who had sort of assigned me to be a part of this left and she said, “You need to make this your thing,” and so I did and that was kind of my M.O., you know, really, my sort of favorite thing I did at Forbes, thing I was most proud of was building up this coverage of not only entertainment, but specifically hip hop.

 

And, you know, I think that, at the time, there wasn’t really any other major, you know, business publication that was treating hip hop seriously and, you know, sort of not as a fad.

 

And, you know, I grew up in New York loving hip hop and, you know, to me it was never a fad, it was just what I grew up around and the idea that there was no sort of serious business coverage of it, to me, was just ridiculous, so I kinda took it upon myself to, you know, to build out our coverage and give hip hop the respect that it deserved, and, you know, not just as a musical genre but as sort of like a, you know, a cultural force to be reckoned with from everything, you know, ranging from fashion to venture capital, and it’s been so fun to cover the business of hip hop, you know, as a really big part of that coverage area at Forbes over the years and, you know, I think hip hop responded in kind with all the shout-outs of the Forbes list and this and that.

 

So, you know, it’s been super rewarding to do and, you know, that’s always gonna be a key part of my coverage, you know, wherever I am.

 

Dan: You mentioned the billionaire remix for “I Get Money” and I do remember that because that, at least in my memory, was one of the first big shout-outs I remember where Forbes got the name on the actual track list.

 

What are some of those other pivotal moments or like those watershed moments you can remember of like, “Oh, like this is growing. This is growing,” because I’m sure that was the first one but I’m sure there were others after that too.

 

Zack: I think that another watershed moment really was Bruno Mars, you know, “I wanna be in the cover of…Forbes magazine,” and I think when that song came out, you know, he was not big at all and we weren’t really sure whether, you know, it was Bruno or Travie McCoy who was kind of gonna be the one who got really big after that song.

 

And we’re like, “Oh, cool, you know, Bruno Mars, a billionaire guy,” but like, “Who is this guy?” But, you know, I think, to me, it was Bruno who obviously eventually became this huge superstar but he gets so many of his influences through hip hop and R&B and, you know, the idea of like whatever it was that hip hop had seen in Forbes, he saw, he discovered it, I think, through the lens of listening to hip hop that then inspired him to write this, you know, big basically advertisement for Forbes which like, you know, talk about earned advertising.

 

I mean, you know, authentic endorsements. I mean, obviously, you know, that’s nothing — Forbes doesn’t pay anybody to rap about it but, you know, I think that that kind of signaled, you know, kind of the groundwork that hip hop was laying, you know, and like then it getting amplified out into like all these other audiences.

 

Dan: Yeah, for sure. And I think after the work that you’ve done as well, I think we started to see more and more of these other websites that are talking about what celebrity’s net worth is and how much their valuation is, and I’m sure that you’ve seen a lot of these, I’ve seen a lot of these and you’re like there’s no way that that number is accurate, some of these numbers that are out there are crazy, but I know that the work that you did at Forbes was obviously very different than what a lot of these other websites did, so I’m curious, from your perspective, where do you think that a lot of those other places may get some of these numbers and what are some of the things that you did at Forbes to make sure that your numbers were as close to being, not just accurate but as close to being what you wanted to put out there?

 

Zack: Yeah, I mean a lot of those numbers floating around the internet, you know, they got from me or my colleagues and then a lot of them, you know, as far as I can tell, they just make up, so, you know, it’s like a math class in high school, right?

 

You can’t just put the answer on the sheet, you need to show the work, and, you know, let’s say that was how it always was at Forbes, like even though I was the one doing the valuations for the hip hop stuff for the most part, I still had to get it past, you know, the billionaires editor, right? If you’re gonna call Jay-Z a billionaire, you need to convince the billionaires editor who also signs off on the number for Elon Musk and Bill Gates and Oprah, and, yeah, you have to show your work and so, you know, although you may not see all the work on that page of the magazine, you know, where it has the line that it says, “Jay-Z $1 billion,” rest assured that, you know, deep in the bowels of the Forbes billionaire wealth database, you know, there are pages and pages and pages and months and months and months of work on that Jay-Z number.

So, you know, I mean, Jay-Z in particular, just to give you an idea of the work that goes into it, I spent more time showing the work, showing the proof of work for that billionaire valuation than I’ve spent on many cover stories I’ve written. There was months and months of going back and forth of valuing every single company in his portfolio, of talking to, you know, sometimes three, four, five different industry analysts, you know?

 

Booze analysts when you’re talking about Armand de Brignac, you know? Music analysts for the music stuff, you know? Spotify analysts for the Tidal stuff.

 

And because with Jay, most of the companies are privately held and not, you know, he didn’t until recently, you know, sell big chunks or most of, you know, his stakes in Tidal or what happened with Armand de Brignac, you have to actually dig around and this isn’t, you know, you have to — it’s shoe-leather reporting, you gotta go and, you know, scrounge up the numbers and you have to get people to talk to you on background and then you find the revenue and then you compare that to a similar publicly traded company but there aren’t exact comps, because, you know, Jay Z’s champagne company was just champagne, and like a lot of the publicly traded companies are champagne and other spirits or champagne and fashion or whatever. 

 

So, you know, it’s just a lot of that back and forth valuating companies and figuring out what his percentage is and, you know, just a ton of reporting that goes into it.

 

So, long story short, that’s why I get so annoyed when I see numbers out there that are just very clearly, you know, somebody making something up to put on a page because, you know, I know how much work goes into those numbers when I create them and, you know, when my colleagues at Forbes would create them.

 

You know, it is really like — it’s, you know, both an art and a science, that something that, you know, takes a lot of time and care to get right.

 

Dan: And with that Jay-Z example, specifically, because you said so much was — so much effort was put into making sure that top line number was set, was a lot of it more so just trying to get as precise as you could or was it the broader aspect of, “Can we verify that Jay-Z is a billionaire?”

 

Zack: Yeah, I mean, there’s some point at which, you know, precision is impossible, right? Like I can’t tell you to the dollar or to the hundred thousands of dollars or even to the million, you know, or even the tens of millions like how much Jay-Z is worth, but, you know, you wanna be — when you’re talking billionaires, you need to be accurate, you know, let’s say to the hundreds of millions or, you know, particularly when somebody is just becoming a billionaire, you really wanna make sure that they’re comfortably, you know, there, right?

 

And you don’t — what you really don’t wanna do is call somebody a billionaire when they’re just kind of puffing themselves up for it for, you know, one reason or the other only to have the thing come crashing down and then you look like an idiot.

 

So, you know, let’s say, I was convinced about Jay-Z for some time and then it was a matter of, you know, convincing others. And, you know, I think that there’s sort of like a level of, let’s say, risk aversion, right? Especially to people in the entertainment business, you know, from the folks who edit these things because, you know, entertainment business is kind of a volatile place, right?

 

But Jay-Z is an exception. I mean, Jay-Z is like, you know, he’s that guy who’s gonna just keep growing and finding ways, you know? That line that he says, “Put me anywhere on God’s green earth, I’ll triple my worth,” and, you know, to me, like I think, when I first heard that he was probably worth $400 million and here he is triple his worth, so, you know, and then some, I mean, I haven’t done the latest number yet but, you know, I anticipate there’s gonna be a lot of work to be done and, you know, proof of work to be shown following Jay-Z if he continues his climb because I don’t think he’s stopping anytime soon.

 

Dan: Yeah, especially after the moves that he’s made since you put that out. I mean, there’s been the Ace of Spades deal and the Tidal deal so all of that, I’m sure, and that’s just part of it, right? There’s this Tiffany’s deal. There’s so many things that he’s continued to do since then.

 

Zack: Yeah, you know, in a funny way, he’s like that person in your fantasy baseball or football league who’s always making these trades and, you know, they may not all make sense in a vacuum, but, actually, you know, if you kinda put them all together, they’re always building towards something else, you know? They’re always building towards that next big deal.

 

And I kinda think that, you know, what we’re seeing now with, you know, the big payouts he’s gotten for Tidal and Armand de Brignac, you know, these have all kinda come — the timing is kinda fascinating to me, right?

 

Like I think that he’s preparing something else that’s pretty big and I’ve always thought that a big thing that he would like to do down the line is to own not just a token piece but like a significant and ideally a majority share of an NFL football team and, you know, these are multibillion dollar entities.

 

So, you know, you have to be pretty wealthy to be able to do it, you have to be able to, you know, take out some cash but there are restrictions on, you know, how much, it’s like joining a co-op or something, you know, if you’re buying in, it’s not just that you’re approved for 20 percent down for whatever mortgage, like they may have a requirement that you have to put down 50 percent or, you know, pay all cash or whatever. So, I do see him building towards something and I kinda think that his next step is a professional sports team. And not just in the way that he had a piece of the Nets back in the day.

 

Dan: Yeah, that’s a good point because I think that’s the distinction. I think it was 0.15 percent or a 15th of a percent, it was some, you know, decimal point of what he owned.

 

And I remember the rumors started to come out about him wanting NFL team ownership right around the time that he had made the deal with NFL Commissioner Roger Goodell for Roc Nation’s partnership for NFL’s entertainment and the Super Bowl Halftime Show and all of that.

 

So, yeah, I’m with you. I think that will eventually come, for sure. And I think some of the things that he’s been doing as well, it seems like him and Jack Dorsey are stepping more into crypto and I feel like even him turning his social media avatar into a CryptoPunk, like he’s clearly trying to lay some groundwork for all of these things. And, yeah, I mean, at that point, it’s like those are the things that you would naturally expect him to do but, yeah, I do think that of all those things, you know, the NFL team ownership is definitely the big one.

 

Zack: For sure. And, you know, who knows? I mean, maybe he tries to buy the Nets back outright, maybe he tries to, you know, get in on a baseball team, but, you know, I think — I do think with Jay-Z, you know, like, first of all, Jerry Jones isn’t selling the Dallas Cowboys, you know, and the Steinbrenners aren’t selling the Yankees, but Jay-Z, you know, he’s not the one to kinda go after and have the sort of like primo, you know, a number one brand, he wants to go to the rival and build them up or he wants to start his own thing.

 

So, you know, that’s kind of the way — you know, that’s what he did with the Nets, right? He didn’t do what he did with the Nets with the Knicks because they were already kind of, you know, fully realizing the power of their brand, but he saw an opportunity to turn the Nets into something cool and to be a part of the move to Brooklyn and, you know, I think that’s what he would probably try to do in sports team too.

 

Dan: Yeah, definitely, for sure. Well, let’s shift gears a bit. I wanna talk more about you and some of the moves you made specifically, because I think a lot of this does relate, we’re talking so much about how entertainers are doing multiple things, how they’ve shifted their model over time, and it’s been interesting to see how you as a journalist and as a writer and someone that’s now doing their own thing has done that, because I think over the past two to three years, we’ve seen a number of big-name journalists like yourself that have moved off of the brands and companies and the publishers that they’ve been with for years and they’re like, “You know what, I wanna branch out and do my own thing, I wanna launch my own,” and a lot of them have gone on to Substack, which you have, but I think you’re doing it in an even more unique and interesting way because you’ve written several books and, this time, instead of releasing a book with a traditional publisher, you are releasing your next book, We Are All Musicians, through Substack and that is essentially the publishing outlet that you’re using for that, and I think that’s a really interesting model and it would be great to hear what that decision was like to leave Forbes and then work with Substack, now working more independently on your own thing and what it’s been like.

 

Zack: Yeah, I mean, so, you know, there was an intermediate stop there that that, you know, sort of didn’t happen but was crucial to this whole process for me.

 

So, you know, I mean, like I said, my career at Forbes was old enough to drive and I felt like it was, you know, time to try something different and, I mean, honestly, like seeing the hip hop things through from the very beginning of the serious coverage of hip hop in, you know, the business media world to Jay-Z becoming a billionaire, you know, Kanye on the cover, like I felt like I had sort of like accomplished my mission, like I had followed this trend, you know, to — I mean trend, I mean, movement, you know, this kind of like ground-shaking cultural institution, right? To this pinnacle.

 

And I didn’t really know what more there was to be done at Forbes and so I got this great offer from, shall we say, a rival publication and, you know, with all kinds of great promises and really an emphasis on the writing, which is my favorite part of the job, to be really almost exclusively doing long-form features, and so I said my goodbyes at Forbes, I took a few weeks off, I signed this offer letter to leave, and then a few days before I was supposed to start, I got this — this basically an IP grab, this like 50-page document that sort of seemed to wanna own 100 percent of all of my everything and, you know, for me, I do a lot of stuff outside of the day job, including books and from TV and film stuff that I’m starting to dabble in and, you know, that wasn’t kind of part of how I had conceptualized this next step and, you know, it was all news to me.

 

So I brought in my book agent and he tried to, you know, kind of bring us to some kind of agreement, but, basically, you know, the other side wouldn’t really budge so I walked away. I walked away and I wanted to — I think after that experience, what I realized is that, you know, a lot of these newspapers and magazines are starting to see the appeal of, you know, the possibility of getting a piece of a Hulu series or Netflix or whatever, and I think, even more insidiously, some of them want pieces of your books not for the sake of it being your book but because there’s a sort of backdoor, you know, if, yeah, maybe they have the rights to your, you know, to produce your articles, to option them and turn them into TV or movies, but if you write a book about one of your articles and they don’t have that right too, you know, you could go then option the book and turn that into something and kinda get around it that way.

 

So, you know, you’re seeing some publications are now calling for, you know, reporters to have to get permission to even talk to a book editor or a literary agent, which I think is just bonkers.

 

And, anyway, you know, how could I really follow these guys, Jay-Z and Puff and Dre, you know, through their entire careers and then go and like give away all my ownership of my own intellectual property? It just — it would be so hypocritical and like just feeling like wrong, like feeling — I don’t know, it doesn’t really feel right to me to be doing that. So I basically cold-emailed the founder of Substack and I told him, you know, my experience and I said, “Look, I’ve been — I’m about to start shopping this book, We Are All Musicians Now, and, you know, but I’d be interested in serializing it on Substack,” you know, Charles Dickens style, week by week, you get a different chunk and that’s for the paid subscribers, and then, you know, for the free subscribers, I would do the Zogblog, I would do basically what I was doing at Forbes, intersection of music, media, and money.

 

And, you know, within a week, because startups move fast, you know, we’ve come to an agreement and, you know, they definitely — they made it worth my while to come over. They gave me a grant as they’ve done with some writers, but, you know, at the end of the day, the model doesn’t work if people don’t sign up, and so that’s on me, and that’s now, you know, in addition to writing and creating really compelling work, I have to go out and do the audience development and, you know, there’s no safety net for that. There’s no “It’s somebody else’s responsibility,” as you know, it’s all on me now and that’s a whole different side of the brain from, you know, from creating and it’s a side of the brain that I like to use too. So, it’s been a really fascinating journey and so I’m — I’ve only been doing the Substack thing now for a couple months but, you know, I’m doing the weekly blog posts and then I’m rolling out this book, and I just love the rhythm of it, I love the idea of being my own boss, I love the creativity, the freedom, the voice.

 

You know, I’m not trying to have to adapt my voice to be, you know, some publication’s voice. It just gets to be me and I get to say what I want.

 

So, you know, it’s super freeing, and then, at the end of the day, knowing that I own my work, you know, I can sleep easier at night.

 

Dan: Yeah, definitely. And I feel like that voice piece is important, because I’m sure with so much of what you did, you had your version that you would put out and things had to be adjusted to fit the Forbes format, whatever that was.

 

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Dan: How different is the Forbes voice versus your voice?                         

 

Zack: Yeah, you know, it’s different. I mean, I think that one of the things that Forbes does that I do appreciate is that, you know, they do leave room for some first person in there.

 

There’s like — I wouldn’t call Forbes a gonzo journalism publication by any stretch, but it’s certainly more gonzo than The Economist or The Wall Street Journal, and, you know, there isn’t really like a gonzo business publication, right?

 

Maybe that should be my next project. But I do think that, you know, given that the world that we live in now, when, you know, you can be in somebody’s living room by going through a phone that you open with your face, you know,

 

I mean, there’s really no excuse for writing that is like stodgy and impersonal. Like you really have to put the reader there with your words if you wanna compete with the actual visual, the audio visual, being right there with whatever you’re wanting to know about.

 

So, that’s kind of my style and, yeah, I mean, I would say that, ideally, my style, you know, my style in its most ideal form is more gonzo but, you know, of course, you have to be with whoever you’re writing about in order to have that kind of gonzo experience and that’s harder in the pandemic era, and it’s also harder when you’re writing about people like Jay-Z who don’t really wanna talk to anybody anymore because they can just put everything out to social, or in Jay-Z’s case, not put things out on social and, you know, create that kind of scarcity.

 

So, you know, I think that just having the freedom to play around a little bit more with the voice and the style is something that I’m really, really, really enjoying.

 

Dan: I see that, yeah. That makes sense. And I think that this book will be a great example of that too. Can you talk a little bit more about We Are All Musicians Now and where the thought came behind the book and what are the key themes that you wanna get across?

 

Zack: Yeah, the thought really — I like to say musicians borrow, right? And the title is borrowed, with permission, from one of my best friends, a guy named Jon Bittner, who’s the CEO of a company that I actually invested in really early on called Splitwise, and, you know, he said — he read my Jay-Z book many years ago and he said, “Now I get it. We are all musicians now,” and I said, “What do you mean?” and he said, “You know, we’re really like everybody is trying to make sense of how to, you know, how to sell things in an era where everything is kind of available for free all the time on the internet and, you know, how you do that, you know, pretty much for anybody comes out of the same toolset, toolkit that musicians have to use, you know, in the post-Napster world,” but I guess the point of the book is, yeah, and so I started thinking about that, and I was like, “Yeah, we are all musicians now,” and so how far back does it really go?

 

Well, you know, I think things started to change, you know, certainly in like the middle of the 20th century for musicians. I mean, they were — that was when they were really getting taken advantage of but, you know, maybe by the 70s, you know, you had acts, you know, 70s and 80s, trying to fight to get their masters back, right? The master recordings, their publishing rights, you know?

 

You had great stories of, you know, the intrigue between Michael Jackson and Walter Yetnikoff and how he was gonna, you know, use some, you know, big blow up that Walter had on him as an excuse to sort of like get his masters made —there’s this whole — I actually wrote one on my Zogblog posts — sorry, it was a part of We Are All Musicians Now. There’s a great story how Walter Yetnikoff, who is the head of CBS Records at the time, which Michael was on, he really offended Michael because he sued this rival record company that had put out the soundtrack storybook album that had gone along with ET which Michael had worked on because they had put it out while they were trying to promote “Thriller” and all this stuff, and Michael’s very offended by this and so, basically, in order to win back, let’s say Walter wanted to find a way to win back Michael’s favor, and so Michael’s lawyer said, “Give him back his masters,” and he did. 

 

You know, so stuff like that. I mean, you saw artists being able to pull off things like that starting in the 70s, 80s, you know, in rare cases, but now moving to a point where, you know, having split ownership of masters and publishing and all of that is, you know, is more standard.

 

It’s not just like, “Hey, we’re giving you an advance and we’re gonna own all of your everything,” but here we are, you know, in the media industry, in journalism and, you know, if you write something for somebody, if you’re on staff, they own it 100 percent and maybe that’s right, maybe it’s not.

 

I mean, I personally think that some kind of split ownership should be the default, like it is in music, and certainly for freelancers, you know? I think freelancers should absolutely own everything and I think staffers should have a stake in their stuff too, but, you know, I think there’s so many other applications, right? Like if you look at the death of physical retail, where did it begin? Tower Records. And that happened way before, you know, you started to see all these other businesses shutting down their brick and mortar stores and, you know, going online.

 

If you look at the rise of streaming, you know, that was — Spotify hit way before Netflix became thoroughly mainstream and even now with NFTs, I mean, you know, I always like to talk about how the Wu Tang album was the first ever NFT even though they didn’t call it that. And that was, you know, seven years ago.

 

So there are all these applications and it’s like if you follow the musicians, you can kind of tell the future.

 

Dan: Yeah, definitely. And that last example there also makes me think about some of the issues and lawsuits that Hollywood actors have been having. Scarlett Johansson is suing Disney because of what she feels is a breach of contract with Black Widow being on Disney+.

 

And that reminds me of the arguments that Taylor Swift had had about Spotify and not wanting her music on Spotify for years and it even dates back to some of Metallica’s issues with Napster from two decades ago.

 

So, I think that tracks as well and I think another example, you had mentioned this in your writing when you were talking about the book is just even the concept of the iPod.

 

Everything that we’re now doing from a mobile technology perspective, that was a music product and that paved the way for what people are now doing with video, what people are now doing with all of these other things.

 

Zack: Exactly. I mean, it was a music player, like that thing that you have, you know, in your hand, that was a music player before it was a phone. And it became so clear that if you could just have all of that stuff that was on there and turn it into a phone, you know, you have a multibillion dollar — I mean, you could call it a trillion-dollar idea. What’s Apple’s market cap now? It must be over a trillion. So —

 

Dan: Yeah.

 

Zack: I mean, it’s — yeah, I mean, it, again, all goes back to music.

 

Dan: No, definitely, definitely. And it’s been good too and it’s been really, I mean, fascinating to read a lot of your writing. I’d read the most recent book you’d put out as well, A-List Angels, and I think in some ways, that’s almost the opposite type of trend where something that tech and those folks have been doing for years, investing and backing startups and companies, we started to see more athletes, more entertainers, and more hip hop artists as well getting involved in that landscape. And you put the book out early in 2020 but I feel even since you put the book out, there’s been so much more that we’ve even seen, especially in the pandemic, from an investing perspective.

 

So, I’d be curious also to hear your thoughts overall on that book but then how you think your views may have changed at all since writing that book and what we’ve seen happen in the pandemic.

 

Zack: Yeah, no, I mean, I kinda wish that — as I was writing that book, I was like, “I gotta get it out before somebody else writes this book,” you know, “I don’t want it to be late, I don’t want, you know, the bubble to burst,” whatever, but I think in some ways, I wish I had put it out, you know, a year later because I could have gotten a lot more stuff in there and, you know, a few months after the book came out — and the book talks about how the likes of Shaq and Nas and Ashton Kutcher and, you know, J.Lo and so forth were able to invest in startups, either with their own cash or, you know, advisory shares, and, you know, and to really kind of like diversify and to break into what had been this very exclusive, you know, like let’s call it what it is, old white club and, you know, old white men.

 

And suddenly, you have all of these entertainers coming from all kinds of different backgrounds and being able to get into these very exclusive startups and venture funds and, you know, and put in amounts of money that are much smaller than the minimums, let’s say, for, you know, for most institutions, or, you know, that would usually be doing this kind of investing. So, you know, there’s sort of like a democratizing of Silicon Valley that has happened, you know, of course, it’s still very hard to get in if you’re not rich, but at least, you know, there’s a way for different kinds of rich people to get in.

 

So, anyway, I wrote this book and, you know, it comes out and, of course, in the very beginning, in the darkest days of the pandemic, you know, nobody wants to read about stars investing in startups and, you know, had to cancel the book tour and all that.

 

I mean, look, if that’s the worst thing that happened to me in the pandemic, I’m one of the very lucky ones, so, you know, but it’s been kinda cool to see that there’s a long tail to it and to see that some of the things that I had wrote about were, you know, kind of coming to greater fruition, you know, even after it came out.

 

So, I think the way that the Clubhouse deal went down, you know, and the idea that you had Kevin Hart in there and, you know, he was somebody who was in the orbit of Andreessen Horowitz and kind of helped convince the founders to go with them, and, you know, that whole story and, you know, there are a lot of examples, you know, Clubhouse maybe, you know, isn’t quite where it was, you know, mid pandemic but, you know, the fact is that it’s become this huge sort of cultural thing that, you know, that it might not have if it wasn’t for that kind of celebrity involvement.

 

And I think that just goes to show, you know, the power that entertainers can have when attaching themselves to a brand and it’s not just like for the mass market, it’s not just for sort of like tweeting about whatever product to get users to come along, it’s about, you know, impressing founders and like getting somebody to come in and be a part of it. So there are just so many ways that celebrity investors have proven to be really valuable to startups, I think, you know?

 

And then we see the evolution of a firm like Andreessen Horowitz to be this sort of like social and economic kind of flywheel community where, you know, there are all these characters who are in the orbit that can kind of feed on each other in order to create, you know, more value.

 

And I think it’s a pretty incredible model and the book deals, you know, a lot with Andreessen Horowitz and that kind of syndicate that’s built around, you know, around some of those investors who you see jumping into stuff together.

 

So, you know, it’s been really kind of validating to see some of the theories and observations borne out in the time since the book’s been released.

 

Dan: Yeah, I hear you, especially on the part about you feel like maybe the book was a little bit ahead of its time and I know that something that people have often said about, especially things that are like cultural trends and a lot of these things are easier to see when we’re in hindsight, but, still, I think that it’s almost better to have something like that out there because it does help some of the content age well. I mean, you had a whole chapter in there dedicated to Nas and I think a lot of people knew how prolific Nas was, but his exposure when people realize, especially after the Coinbase and the Robinhood deals earlier this year has gone to a whole ’nother level and you have the reference point for that.

 

Zack: That’s right, and you’re seeing, you know, Nas’s exits, you know, from a lot of the companies that I talked about and I interviewed Nas and, you know, that’s all in there and, you know, there’s some of his insights about why he invested in certain companies, you know?

 

I talked to his manager, Anthony Saleh, who, you know, who told me this great story about how they were gonna invest in Casper — or, rather, the opportunity to invest in Casper came along to Anthony and he was like, “Ew, mattresses, why do I care?”

 

and Nas was like, “Wait a minute, no, I grew up in New York, this mattress comes in a box? Like you can just take it up the stairs and it pops out in your apartment like a caterpillar, you know? I mean, that’s amazing,”

 

and so they’re like, “All right, sure, why not?” and, you know, and now we’re seeing the, you know, sort of the fruits of that labor, but I do think that, you know, Coinbase, I mean, that was another story that was in there in terms of, you know, Nas, you know, being a really useful part of the team.

 

But I think that, you know, entertainers, and specifically musicians, they bring a certain je ne sais quoi to the table and it’s like there’s that instinct, there’s that like what’s hot or what’s gonna work or like, you know, what people want.

 

You have to be able to deliver that as a musician and you also have to be able to deliver that as an entrepreneur, as a, you know, VC or a company.

 

Dan: Yeah, definitely. I think that it’s always really cool to hear the stories about what made certain celebrities or entertainers decide to invest in things. That Nas-Casper in a box story is great.

 

I also think it’s another one you may have mentioned, but I think it was Shaq that had invested in Google because he had heard some people talking about it on the elevator and that just gave him this hunch that it was this thing.

 

Zack: Oh, yeah, no, it was —

 

Dan: That’s hilarious —

 

Zack: It was even better. It was like he was playing like with some somebody’s kid at like a restaurant, they came up, maybe they wanted his autograph or something, and, you know, he was just nice to this kid and so the kid’s parent came over and was basically like, “Hey, you know, do you wanna invest in pre-IPO Google?” Like Shaq was like, “Oh, yeah,” and maybe he’d also heard somebody talking about it in an elevator so he was like, “Yeah, sure. That sounds cool,” you know?

 

And he ran it by his team and got in and, you know, did incredibly well and like Shaq won’t share the numbers, I did push him on it, but he was sort of like, “My mom says that it’s not polite to talk about money,” and so, you know, what are you gonna tell Shaq?

 

But — all right, I guess we’re not gonna talk about money, but, no, I mean, you know, the thing about somebody like Shaq is, and this is one of my favorite stories from A-List Angels, I interviewed the founder of Ring, the doorbell slash, you know, video doorbell security startup now purchased by Amazon, I think it’s for a billion dollars, and the founder’s name is Jamie and he was telling me how, you know, he brought Shaq on as an investor, I think for some of the reasons that people usually bring celebrities on, just brand awareness, especially consumer facing stuff, it, you know, can come in really handy, but he had a meeting with Shaq and he was saying how, you know, he, Jamie, the founder, really wanted to get in touch with more law enforcement officials to really be able to sell Ring as this sort of, you know, law enforcement-approved home security measure, and Shaq, you know, he’s like, maybe it seems like he’s not paying attention or something and then he hands Jamie the phone and it’s the Miami police chief who Shaq knew from some TV show he’d done down there and, you know, made that connection.

 

As it turned out, you know, Shaq had studied to be — or trained to be a sheriff’s deputy or something like that, some kind of law enforcement official, and so he had all these, you know, connections that he was able to hook up with Ring, which made a huge difference and that’s sort of like not what you would think a celebrity would bring, like that’s not kind of the value that you would usually associate, but, you know, they often have these connections and then there’s also this thing of like, if Shaq is calling you and you’ve never met Shaq, you’re gonna pick up the phone because it’s Shaq, you’re like, “Oh, that’s interesting. I’m the founder and, you know, I’ll pick up this phone,” or, “I’m somebody who another founder wants to do business with, I probably wouldn’t pick up the phone for this unknown founder but if it’s Shaq, like why not? Yeah, that’s interesting. I’ll do it.” 

 

So, you know, I think there’s a lot of paths to value, you know, for these characters when they come in, you know, to be part of a company.

 

Dan: That’s a great story. No, I’m glad you shared that because I know that people, you know, may have heard the Google thing but I don’t know if they knew it to the depths and, obviously, you have the insights there so I appreciate you sharing that —

 

Zack: Oh, sure, yeah.

 

Dan: — definitely. Yeah, all right, before we let you go, I wanna do a quick fire round of some predictions of who we think will be the next hip hop or entertainers to be named on that billionaire status.

 

And, well, we’ve been open there, I mean, I have some thoughts but I’m curious, who are the names that come to mind? Who do you think is gonna get there next?

 

Zack: Well, you know, I was thinking about this a lot and I do kinda have my, you know, my billionaire radar always up. And, you know, unfortunately, my pick would have been Rihanna but Forbes just called her not only a billionaire, I think $1.7 billion was the number, so, you know, so there goes that prediction, but I do think Diddy’s gonna get there and that’s maybe a more boring prediction because, you know, it’s been such a big story and he’s like very open about it but, you know, he’s kinda stuck in the $700, $800 million range — I’d love to be stuck in the seven $700, $800 million range, for sure, like them, you know?

 

Dan: Why do you think he’s stuck there? Do you think it’s like Ciroc has just, you know, reached out of where it’s at or there hasn’t been any like big —

 

Zack: Yeah.

 

Dan: — major business moves or…

 

Zack: I mean, you know, his — I think Ciroc is still a very healthy brand but it’s, you know, it’s — I think it’s already gotten to be the — is it number one or number two? Maybe it’s like number — it’s tied with Ketel One for number two, something like that.

 

I don’t know. It’s up there but it’s like, you know, there’s not much further up to go. So — but, you know, you never know and then I think that’s the thing is, like, you know, it felt like his career, like how many times has it felt like his career was stalled, you know?

 

I mean, in the mid-aughts, it felt like his career was stalled maybe. And, you know, and then he reinvented himself, you know, really, in large part with Ciroc. So I’m never counting him out and I think that he’s always working on whatever the next big thing is.

 

But, you know, I think that — many years ago, I was talking to somebody about, you know, it was an industry insider who, you know, who knew all these figures and like these individuals and he — and I said, “Who do you think would be the next billionaire?”

 

And he said, “I don’t know,” but he said, “You know, it’s probably somebody who’s gonna come out of left field, somebody who’s really brilliant and just, you know, has some great idea and then it just catches on and becomes this huge thing,”

 

and so that was Kanye, you know? That was Yeezy. I mean — and who would have known, you know, in the days of the Red Octobers when you could get them for a couple hundred bucks or something like that, I picked up a couple pairs, but how would you know that Yeezy was gonna be this billion-dollar business?

 

I mean, it’s just, if, you know, if you have an idea or design or something that just so resonates with people, it can scale really quickly and so, you know, I would think more toward like who is the most creative person, you know, kind of coming out of the music world and particularly hip hop, you know, somebody like Travis Scott I think would be a good guess because you could see Cactus Jack maybe following the Yeezy kind of path and that could very quickly escalate into a valuation that would put him, you know, at that level.

 

Dan: Yeah, I’m glad you said him because that was the person that was on my mind because I think the distinction you made is important too because I think, I look at Diddy almost similarly, you know the way I may look at someone like a Master P, right?

 

Both very successful, both well into those, you know, nine-figure net worth status. The difference though is that they are leading mostly either, (a) mature businesses or businesses that have, you know, much lower multiples that they’re involved in.

 

Still healthy businesses, still very successful, but that’s different than, you know, someone like a Rihanna starting something like Fenty Beauty and all the Fenty brands that skyrockets, the product sales that just skyrocket from that. 

 

D is and what Kanye has done with them and Yeezy, skyrocket. And I think you look at someone like Travis Scott, I think the number that I saw out there last year for 2020 was that he had made over $100 million from all the product sales endorsements and most of that is him licensing those in his name and his likeness to other companies.

 

What does the Travis Scott product that he puts his backing behind that gets all these ragers supporting it 100 percent? Yeah, that’s what it is because I think we’ve seen it. Product sales is, for the most part, what drives people to that next level and so I do think he’s probably, you know, one of the better people to bet on there.

 

Zack: Yeah, and I think when you look at, you know, how net worth is calculated, you know, it’s really, you know, if you own a percentage of a company that is worth, you know, in the billions, you know, that’s the fastest path to it because, you know, if you’re somebody who goes out and, you know, and tours like crazy and sells out arenas and so forth, I mean, that’s a great way to make a lot of money but, you know, even if you’re, let’s say you’re doing arenas and, you know, you’re grossing like a million dollars a night, well, you know, maybe you’re only taking home, “only” but, you know, maybe you’re only taking home 300K or 400K out of that, and then you have to take into account your travel expenses and, you know, whoever else is coming along and so maybe you’re looking at more like $200,000 a night, you know, you write all that off but then you still have to pay taxes and you probably live in California, that’s like $100,000 a night.

 

And then like, you know, that’s not even counting the personal expenses and so, you know, even if you’re doing 50 or 100 shows a year, I mean, you’re still, you know, it’s great money but it does get eaten into, there’s a lot of, you know, manager’s fees, lawyers and all that, it does get whittled down and then, you know, and then you have to find a way to keep it and grow it. But, you know, if you found a company or you invest in a company that’s really taken off like a rocket ship, you know, all that value is right there and, you know, I think, actually, because of the way the numbers are calculated by Forbes and, you know, how I would calculate them independently, it does look better before you sell, right?

 

Because, you know, and maybe this shouldn’t be done this way but let’s say you found a company, it has a $1 billion valuation and you own it outright 100 percent, I know that never really happens but let’s just say,  then you would be worth a billion dollars but, I mean, you’re not really because if you sold it for a billion dollars then you would have to pay all the taxes and you would have to do this and that and then you’d have, you know, whatever, half, two-thirds of that number so the method of calculation does advantage people who are investing in startups or have founded companies that have not sold yet and, you know, and then there’s sort of like Uncle Sam takes his cut and then you get a lower number.

 

So, based on the way things are calculated, especially, I think somebody like Travis Scott who could have, you know, a company, a product line that has a certain valuation, you know, and not necessarily be selling it, you know, you can get to that number.

 

Of course, like, a lot of times, we don’t even find out how valuable something was until somebody sells it so that’s the flip side.

 

Dan: Yeah, definitely. Well said, man. Well said. Well, Zack, man, this was a pleasure. Thanks again for coming on. And before we do let you go now, just give one more plug, where can people find your work? Where can people find We Are All Musicians Now?

 

Zack: Yeah, you can find it on Substack, the friendly URL is zogblog.co and, yeah, I hope you check it out. Thanks for having me on.

 

Dan Runcie

Dan Runcie

Founder of Trapital

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