Feb. 28, 2022

Trapital’s Dan Runcie on the Entrepreneurial Spirit of Hip-Hop

“I’m a business, man.” - Jay-Z

Nora and Scott chat with Dan Runcie, founder of Trapital, a weekly newsletter about the hip-hop industry, and look at how trends and strategies that start in hip-hop influence the rest of the business world.

Hosts: Nora Ali & Scott Rogowsky
Producer: Bella Hutchins
Production, Mixing & Sound Design: Daniel Markus
Music: Daniel Markus & Breakmaster Cylinder
Senior Producer: Katherine Milsop
Director of Audio: Alan Haburchak
VP, Head of Multimedia: Sarah Singer

Full transcript for this episode below.


Scott Rogowsky: We're talking hip-hop, a hippy to the hippy, to the hip hip hop. And we don't stop talking about hip-hop this episode.

Nora Ali: I predicted you would do that. Here we are.

Scott Rogowsky: You did? You predicted that?

Nora Ali: I called it. We're talking hip-hop today.

Scott Rogowsky: Yes.

Nora Ali: Are you a hip-hop fan?

Scott Rogowsky: Do I like hip-hop? Yes. I like hip-hop, Nora. I don't like as much as the commercial hip-hop that is out there on the radio and the people making the moves. But you know, of course, the big names, I mean, Kanye, and Dre and Jay-Z. And these are moguls.

Nora Ali: They're icons.

Scott Rogowsky: They're icons, yes.

Nora Ali: They're staples to any music diet. Yes.

Scott Rogowsky: Yes, of course.

Nora Ali: I'm a big consumer of the products that these artists create. I'm a huge Fenty user. I'm actually wearing Fenty lip gloss right now. Rihanna is one of my business idols.

Scott Rogowsky: Wow.

Nora Ali: And this came up in our conversation with Dan, but she's tapped into a market that has felt underserved when it comes to makeup. And do you know what a contour stick is by the way, Scott?

Scott Rogowsky: Yeah, I've got three of them.

Nora Ali: Well, I've purchased products from Fenty that I wouldn't otherwise even want or need because you just feel like it's such an elevated brand and beauty influencers on TikTok love it so much.

Scott Rogowsky: Nora, are you buying the Stem, the Stem device to listen to Donda 2? This is Kanye's thing. He's selling his own streaming platform, streaming device so you can listen to his new album. It's actually interesting. He's like, screw Spotify, screw Apple. He's like, I'm taking it all. The value for the artist is being lost. 12% goes to the actual artist. He's like, I want a hundred percent. Ah, you got to give him credit for it.

Nora Ali: So we stan all these hip-hop artists.

Scott Rogowsky: Absolutely.

Nora Ali: And today we were lucky enough to talk to an expert in this space. His name is Dan Runcie. He's the founder of Trapital, a media company that covers hip-hop business and strategy and through newsletters, podcasts, and essays, Trapital unpacks the business moves of hip-hop icons from Jay-Z's cell phone partnership to how Issa Rae became the modern mogul shedding light on lessons and trends that apply to the entire business world. From Morning Brew, this is Business Casual. The podcast reveals the unexpected business story behind everything. I'm Nora Ali.

Scott Rogowsky: And I'm Scott Rogowsky. Nora and I are here for your ears, bringing you conversations with creators, thinkers, and innovators who can tell us what it all means and why we should care. Now let's get down to business. Dan, it's a pleasure to meet you. I love your writing about hip-hop and the business of hip-hop, which some people might say, well, oh, this is a new phenomenon, but really business and hip-hop have been intertwined since the beginning almost, can you walk us through maybe the history of this and why you decided to take a look at hip-hop through the business lens?

Dan Runcie: Yeah. One of the unique things about hip-hop is that this is a culture that was really borne out of constraints. And that's where we saw so much creativity come through. You think about the artists that didn't necessarily have all of the respect from the gatekeepers. So they had to build their own and so much of that is that entrepreneurial spirit, whether it's someone like a Jay-Z who got turned down by many major record labels, and then he goes and starts his own business, his own record label, Roc-A-Fella Records. If you look at the eighties and the nineties as this era where hip-hop is fighting for its respect, especially just considering the boom you had and that golden age where you're seeing more of these artists top the charts and get more mainstream respect, but things starts to change right around the time that technology starts to expand. And you're seeing artists leading more into things, whether it's mix tapes or leading into ringtones. And you're seeing artists now being the early ones in hip-hop that leaned into streaming. And you're seeing it now with NFTs as well. And especially in the social media era, where the barriers to creativity and just the barriers of access lowered. It's no coincidence that you saw hip-hop realize much more of its true power in this era. And with that, the business of that and all of the artists, how they're able to make money, how they're able to leverage their platforms. It's really been impressive to watch. And that's why it's not necessarily as much of a surprise why there may have been few hip-hop billionaires decades ago, but now fast forward 2022, you're seeing and hearing more of them either at that point or close to it.

Nora Ali: Before we get into more specifics on how artists are monetizing in this new era. I want to understand your approach to studying hip-hop through Trapital first. And you've said in past interviews that you've modeled your approach to this Harvard business school case study about Beyoncé's surprise album, Beyoncé. First, what was the premise of that case study? And why did it resonate with you? Why did you think that was a good approach to studying the space?

Dan Runcie: That case study came after Beyoncé shocked the music industry at the time, because for an artist of her level and her stature to release, not just a album, but a album that had visuals and music videos for each of the songs and everything behind it with no notice, was completely unheard of. But she did it on her terms. And it was such a phenomenon that Harvard Business School had done a case study that broke down all of the decisions. So it wasn't necessarily that the case study was just about Beyoncé, but it took that opportunity to really bring you behind the scenes of what she did before, what she was able to do after. And as someone that was in business school at the time, and I'd spent a large time in my career reading case studies like these on every other industry, you could imagine it stuck out to me that there was one like this, that was also about Beyoncé.

Dan Runcie: And the thing is, it made so many headlines because it was a reminder that you don't necessarily see case studies the same way you might see ones on Southwest Airlines or Disney or New York Times or any of these other companies that you typically see studies about. You didn't see them about one of the most successful entertainers, who's built one of the more unique and remarkable businesses. And that's when it stuck out to me that there was an opportunity to do this just considering how much of a buzz this created. And there needs to be more of these because it can't just be the superstar artist. There's so many stories within hip-hop. There's so many stories around Black musicians, more broadly, that deserved to be told. And that was the early impetus for thinking about what eventually became Trapital.

Nora Ali: And I think you've helped people realize just how interconnected the world of hip-hop and music is to countless other industries with hip-hop specifically impacting sports, liquor, fashion, beauty, all these other industries for decades and shaping our culture. Why and how do you think these trends in hip-hop have been so powerful as forces across categories, across industries?

Dan Runcie: The thing is what hip-hop has that so many of these other types of mediums or other types of avenues don't have, it has that cultural connection and that cool factor that keeps people connected. There's this authenticity that comes from the way that the artists themselves and the companies they create present themselves. And that's why so much of what you now see as mainstream in pop culture is something that is derived from hip-hop in many ways, whether it's how people speak. If you think about it, even from a business perspective, you're starting to see that influences how many companies have made decisions on what things that they might do and how they may go about it. For instance, I think about how hip-hop artists are much earlier, as I mentioned, on things like streaming or whether it's NFTs or even looking at some of the earlier music technology you saw that happening from hip-hop so much earlier than other places. And then even when you expand to other mediums, you see that video and other areas often follow what you see happening in audio. So I think from a technology perspective, you see hip-hop being influential, but there's also that collaboration nature and the aspect of people coming together to create things. I think it's interesting now to think about concepts of DAOs, decentralized autonomous organizations, and how people have these collectors, where they're just bringing these people together that have a unique goal and tying in with what they're doing. And one of the things that I've often said in Trapital, I was like, hey, look at Wu-Tang Clan, go back 30 years. That was the first DAO, if we want to keep it real. The way that they were able to coalesce, they all clearly had this identity, these artists from Staten Island and these artists from New York that really had this vibe and coming together and just each person having a particular role in a sound that creates this type of sonic product. There's so much of that. And even the idea of testing things out like mix tapes being MVPs, minimum viable products, in this space. There's so much of that I think taps into that mentality that we see in hip-hop.

Nora Ali: This notion of the collaborations of the crew, essentially, this is something that was brought up in a Business Insider article recently titled, "How the Black Tech Community is Leveraging Business Models that Made Hip-hop Become a Massive Cultural and Business Phenomenon." Can you just dig into that a little bit more? Why is the collaboration building that community, having that crew so critical to the success of hip-hop and how does that create more pioneership in the NFT blockchain, etcetera space?

Dan Runcie: Yeah, I think it's in a few ways. One of the things that stuck out to me about that article specifically was that, let's just go back a few years, go back to the nineties. You had artists, whether it was a Roc-A-Fella Records. As I had mentioned, if you're starting out new, you're already thinking about, okay, what are all the ways that I can monetize this? What are all the ways that I can leverage this? So you may have someone that's working with you on a film side, you may have Roc Films. That was a extension that Dame Dash and Jay-Z had had. You may also have Rocawear, that's your fashion label that you may have. I know sports is one of the things that they had tried to lead into at the time and you saw all these examples of that as well. No Limit had had something similar, Wu-Tang definitely had the same as well. So when you think about that, especially now in this creator space and people doing things both on-chain and off-chain, you are seeing people leveraging all the tools that are available, whether it is a podcast to share your medium of content, however you may choose or a newsletter, or you may have a merch shop on Shopify. All of those types of things, I think, are examples that tap back into that mentality, that hip-hop artists had that dates back to the eighties and nineties of, okay, this is what we're building. It's one of the things that stuck out to me from Andre Harrell, the late music executive that was the head of Uptown Records. His whole thing was like, hey, we're not just selling music, we're selling a lifestyle. And with that, you just think a bit more broadly of all the things that are available with how they're outfitting Jodeci in the music videos or what Mary J's vibe is. And even flash forwarding to something a few years later, when you have a movie like Men in Black, even though that movie isn't hip-hop itself, it's starring someone that had one of the first Grammy Awards for hip-hop, Will Smith. And he's wearing these sunglasses. And then he does a collaboration with Steve Stoute, who's now one of the leading advertising and marketing executives we have. They do that and the sunglasses sell like crazy. That is I think a further example of how so many of these same mentalities eventually found themselves to the biggest stage as possible.

Scott Rogowsky: Even going back earlier to Run-D.M.C. and Adidas. I mean much did Adidas benefit from that collaboration?

Dan Runcie: Exactly. Yup. Literally he's just like holding his sneaker up at this concert at Madison Square Garden. And then that sets off this wave. It's crazy.

Scott Rogowsky: So much of our world today is rooted in Black culture and hip-hop culture. I mean, you just quoted Andre Harrell who said, "We're not just selling music, we're selling a lifestyle." And you hear that phrase everywhere now by marketers for whatever business they're in. We're not just selling zero cal energy, we're selling a lifestyle. We're not just selling compostable kitty litter, we're selling a lifestyle. And for decades, businesses did not credit hip-hop for these ideas. Is there a way for the mainstream to adopt creative strategies from the hip-hop community, without it becoming appropriation?

Dan Runcie: A hundred percent. I think that as we've seen it now, especially with just how fast social media moves. If there's a hip-hop artist that starts a trend or starts a phrase, you're going to see it everywhere. So you date back to, I think it was two years ago at this point when Megan Thee Stallion's like, this is hot girl summer. And then every brand, whether it's Maybelline or whoever else is like, oh, get your hot girl summer Memorial Day Sale now or whatever it is. And you're just like, okay, sweet. Did you even listen to Meg Thee Stallion's Rooftop Freestyle? Or are you just trying to jump on the phrase? We saw the same thing happen a bit recently because Gunna puts out this album, he puts out that P parking sign emoji, and then he's just like, I'm pushing P this year and now everyone from IHOP to fast food restaurants, they're posting on socials like, oh yeah, we're pushing P too.

Nora Ali: And people don't know where it comes from. They just say it.

Dan Runcie: Exactly. So on that note, I think there is a way to do it in a way that you're showing some type of homage or you're paying respect. Obviously artists have done plenty of collaborations with big corporations and many of them turn out to be very fruitful because a lot of those companies do show at least some genuine connection or at least the people that they're working with at those companies do show that connection and respect. But other times you don't necessarily see it that way. And then it ends up becoming something that feels more tone deaf and feels off. And I think if you're willing to connect with the culture in an authentic way, it's easy to see what's taken as either paying homage or what is seen as doing something with respect or collaboration. But if you're ever putting something out and this is for any brands that are listening, if you're ever putting something out there and you're like, oh, is this the best place for me to be saying that? Or does that match with my brand specifically? If you're questioning that, that probably means it's probably leading more towards, maybe you shouldn't do that, A, or at least at a minimum to talk to someone else about this so that you can get your ears and someone else that may not look like a lot of the people that are in the room with you, who may be making a decision on what to put out.

Nora Ali: All right. Let's take a very quick break. More with Dan when we return. So, Dan, you were speaking on this notion of paying proper homage to our cultural creators and hip-hop artists. And sometimes people just don't get that right. One example of that was the 2019 Super Bowl, the halftime show, where it was totally a missed opportunity. It was in Atlanta. They didn't pay homage to Atlanta's deep hip-hop roots, but in this past Super Bowl, boy, that was an amazing show. We had Snoop, we had Mary J. Blige, we had Dr. Dre, we had Eminem. It was amazing. So do you think industries are shifting, are they realizing that they do need to appropriately give credit where credit is due?

Dan Runcie: It's interesting because with the NFL, I think there's a few ways to answer this. It's not that the NFL didn't recognize all of the things that you were saying, but there was clearly this shift where people could see that the NFL specifically, there was some very big PR challenges that league was having, especially with regards to, A, concussions and player safety, B, a lot of the domestic violence and issues that were happening with these players and C, where it stood on social justice, especially with regards to everything that happened with Colin Kaepernick. And that's just on the surface and when it comes down to it, if you're in the business of trying to maximize TV rights, and you're trying to make sure you can get tickets sold, you want to be able to have a entertainment product that is relatable to where things are going. Especially if we go back to those last few years of the 2010s, so like 2016, 17, 18, 19, when so much of that stuff was there. If you're a league, like the NFL, you're seeing how the NBA is risen in popularity in the age of social media and leading into NBA Twitter and all of these social memes, you kind of want that. So I think to some extent money likely talked and the money likely had an even bigger impact on some of those things. So what do you do? Who's the most influential figure in hip-hop you can find that has a company that can do this? Jay-Z and Roc Nation. So I think in a lot of ways, that likely sparked a lot of the impetus for the deal that happened, but that said, the deal we've seen the outcome of that. I think that Jay-Z himself saw that Super Bowl that was in Atlanta, the one that had Maroon 5 as the headliner, as an opportunity. And to be honest, it's not even any disrespect to Maroon 5. I mean, they're one of the biggest bands of the past 20 years. They deserve to have a spot there, but he saw that as an opportunity to be like, hey, there was an opportunity to course correct for this. So I think that what we saw this past year with the Super Bowl, SoFi stadium in LA, and so much homage paid to West Coast artists, this is an opportunity to set that path and set that tone. And I think not only does that just help with the NFL maybe seeing some improvement of its image, relatively speaking, from the past few years, or maybe just less of the heat than they had had before that. But then you have an event like this, which not only just draws in viewers, but they also saw the stats at this Super Bowl at one of the highest ratings that it had in five years now. And especially now how powerful that is, in an era where I think media is being driven even more by blockbusters. The Super Bowl is one of the few things that has held a pretty high proportion of its audience relative to so many other big shows and big things that have dropped, especially post-pandemic. So I think money likely influenced those things in just seeing how more and more influential and big hip-hop was to a lot of those folks. It was probably easier for Jay-Z and Dr. Dre to have those conversations now in 2022, than they maybe even could have tried to have had those conversations back in, let's say 2012.

Scott Rogowsky: Let's discuss some of your own case studies of hip-hop legends, which you've published in Trapital. You do a great job of unpacking the major business themes and strategies in the hip-hop world, such as leveraging fear, brand curation, and finding your niche. In your piece, "Why Rihanna Broke Barriers That Others Couldn't," you analyze how her cosmetics company, Fenty Beauty, demonstrates the evolution of collabs between high-end brands and hip-hop icons. Can you explain how they have evolved?

Dan Runcie: So if you look at hip-hops partnerships or the hip-hops brands in general, there was a pretty big resistance from a lot of fashion brands to wanting to partner, not even just with people in hip-hop, but more broadly Black celebrities, or just wanting to identify that. I think back to the nineties and just how hesitant Timberland was to lean into the fact that it's boots are starting to skyrocket in the early nineties in sales, but because it wasn't being purchased by construction workers in New England, it was being purchased by hip-hop artists and people that wanted to share how this boot represented their personality. They just didn't lean into them. They tried to push it back. You fast forward a few years later, you're starting to see more hip-hop artists or more hip-hop companies just launching their own brands and leaning into a lot of that late nineties, early 2000s vibe from the brands that are popular at the time, like your FUBUs or your Adicis, or your Meccas and all of those types of brands. I think they definitely hit the vibe of where hip-hop was and just where more broadly a lot of Black culture was at the time. But on the flip side, those companies just didn't necessarily have the global distribution in place to maximize a lot of the popularity that they had. And they ended up over-saturating a lot of markets. And then by the time the moment passed, they kind of got defined by the era that they were in. But then you fast forward to the place that we are now, and maybe even a few years back in the 2010s. Then you start to see more and more collaborations where no, it is hip-hop artists and it is celebrities themselves, and folks like that who are starting these brands and who are starting to have a lot of influence in the collaborations they have. And you look at someone like Rihanna. There was this study in 2016 that NPD had done, and based on their analysis of marketability of celebrities, she was number one on that list. So this was before Fenty Beauty or Savage Fenty had officially dropped. She was number one on that list. So you just put those two things together and you're like, wow, what if this person had the right product and the right thing at the right moment to be able to make it happen? But the thing is Rihanna, someone who had launched products on herself, she was like, you know what, no, who was a partner that I could do this with? So she partnered up with LVMH to have the launch for Fenty Beauty opens up in 2017, the first month and a half goes crazy. They end up selling a bunch of products. And I think breaking a lot of sales expectations that people had, but more importantly, it worked because she was able to tap into an audience and tap into a niche that they just couldn't tap into in the same type of way, and just didn't focus on them. It still blows my mind if you're thinking about it, that no one thought to have that many shades available, like over 40 different shades available for people that had skin tone that may be a little bit darker than what a lot of the fashion industry was putting out there.

Nora Ali: Just a little bit of melanin.

Dan Runcie: That's what they did. Exactly. Just a few shades lighter than a brown paper bag we're just asking for some options below that level, please. But they ended up obviously doing that and you saw the success because there's beauty everywhere in every shape and every country and think about it. If you don't even have those type of shades available, you're leaving out all of these people that would use your products.

Nora Ali: It just sounds so obvious. It's a market that's underserved, and then you have Rihanna, who's found to be an incredibly marketable person, but you wrote a lot about this fear of missing out. And that's what it took to get at companies like LVMH on board. Why did it take this FOMO, and explain what you sort of meant by this fear of missing out?

Dan Runcie: Yeah. So there was this moment that you started to see happen when there were more and more major brands, just seeing how much more popular from a mainstream perspective in their eyes, at least, in their eyes of them seeing where Black culture was and just the consumer opportunity and influence that a lot of Black consumers and Black makers had. So by them not wanting to miss out on that wave and then either seeing one of their competitors do it or seeing someone else that's how Rihanna was able to use that as leverage for her to have something that was attractive. And I framed it in that way, because there were other A-list artists more broadly that had wanted to do something with brands like that. Like I look at Kanye West, he had been in interviews at that time for a while where he was trying to knock on the doors of LVMH, get phone calls back from Bernard Arnault, who is the CEO of LVMH, but he couldn't do it. And I think at the time, even though Kanye was very influential at top the charts and everything, he just didn't have a product at the time that was making them say, okay, yes, you're having something that makes us be like, we're going to miss out on this big trend or big thing. Obviously we've seen since then, what Kanye's done with Yeezy has been extremely impressive. And it's what has made him a billionaire, but Rihanna on the flip side had that leverage. She was tapping into and showing the potential for a market that if we're being honest, always was there, but the industry just wasn't ready to embrace. So it was just a matter of timing to make that happen.

Scott Rogowsky: Time for another quick break. These are the breaks, but more from Dan Runcie when we return. Dan, in your piece, "How The Weeknd Mastered His Brand," you discussed the fickle nature of The Weeknd as an artist, praising his understanding that not having a brand requires the same curation and focus as having a brand and really think about his evolution and his changes with his looks and his sounds. It truly is a masterpiece in and of itself. Why has this approach to brand been so powerful for him?

Dan Runcie: The Weeknd's whole thing from the beginning has been like, I don't want to give everything up at once, because he had just seen so many examples, especially in the social media era now, where if you're just giving and sharing everything else, you're not necessarily leaving the same type of intrigue that may be there for your fans to want more or want to hear more. And to his credit, I do think it's worked out for him. There are definitely some artists who have still been able to be quite successful and share a lot who have put a lot of stuff out there, but for The Weeknd, I think it has worked for him because if we just look back, he released his first few projects, like the Trilogy and especially House of Balloons. There was no photo of him to be seen anywhere. And things obviously just changed when he gets a link of his music that's shared in Drake's OVO sound blog at the time. And then things blow up, people hear this voice, people hear this music, but they're still not sure who he was. It's even to this point where he was working at American Apparel at the time his music is playing at the store, his co-workers are vibing to the songs and everything, and they had no idea it was him. And sometimes that can be seen as a code for just not wanting to play the game in general with being on social. And what The Weekend clarifies, he's like, it takes just as much effort to "not have a brand" or not be all the way out there as it does to be out there. So if you just think about like how masterful he's just been with each piece of it, just thinking about, okay, when he had released that After Hours album, and then he just makes sure that he is everywhere in that red suit for that whole year and doing the whole "Blinding Lights" thing that sets him up so that down the road, when it's time for them to, going back to the Super Bowl, have someone perform, he can say that, hey, it's been a pandemic year, but I leaned all the way in. I've literally had the biggest year now. And I think that's in a large reason why he got picked. And most recently he upgraded the tour that he was on to not just tour its arenas across the country, but tour its stadiums. And there's only a handful of artists that can command not even nationwide, but a worldwide tour in stadiums. So it speaks a lot to what he was able to do. I know he definitely had a bit of a journey there. His first album Kiss Land wasn't necessarily as much of a commercial hit as he had wanted to. So he realized at times, okay, I probably need to lean a bit more into doing the big artist things. So he starts collaborating with Ariana Grande. He starts working with producer Max Martin and making all these big hits, but his journey has been inspiring to watch for sure.

Nora Ali: His approach to branding or un-branding, I guess, has worked to your point, but I wonder what business lessons other companies, brands, can extrapolate from this. Because in your piece on Trapital, you mentioned this e-commerce company, which now doesn't exist anymore, literally called Brandless, where they were predicting that customers care more about value over marketing over the actual way the brand makes you feel. So what are some lessons that other business leaders can take away from The Weeknd's approach to maybe not having as traditional of a brand as others?

Dan Runcie: Yeah, I think the biggest thing there is that you still needed to have something underneath that pulled people in, that drew them in. The Weeknd had that with his music, there was no one that sounded like that, there was no one that gave that vibe. So even if he wasn't in your face doing Instagram Lives every other day, you still were getting something that you weren't going to hear. He was one of the farthest things I would say from a commodity on that respective, this is what didn't necessarily work for Brandless because a company like that, that tried to do the, we'll lean and take a step back from having the brand out there that in a lot of ways is much more akin to the rising artist, that is like, you know what? I just don't want to put my stuff out there. And it's like, well, let's take a step it back. Are you putting something out there that is really unique and original enough for you to be able to take that stance? When you do put stuff out, are you being very thoughtful and methodical about what the plan is moving forward? And I think that's the biggest thing that brands can take away from this because sure, not every brand has to be on TikTok doing dances or doing those things. And we're just fast forward to now, but A, is there a way to use those platforms effectively to your advantage for when you do have something to release? And when that is, do you still have some type of cadence where it makes sense in that type of way? Because just avoiding these things in general, for the sake of it doesn't work. And that's what I think they can learn from The Weeknd.

Scott Rogowsky: Maybe if Brandless had gotten some product placement in Fifty Shades of Grey, they would've taken off the way The Weeknd did.

Dan Runcie: The full circle.

Scott Rogowsky: Yeah. You wrote another case study about Tyler, the Creator and how he built his cult like following in which you discuss this concept called sexy versus profitable. How do businesses often perhaps incorrectly confuse what's sexy versus what is profitable?

Dan Runcie: I think that in entertainment-related fields, it's so easy to gravitate towards what is seen as the cool or mainstream thing, or what is seen as that like ideal consumer, all these brands want to advertise to this millennial or this Gen Z person that like wears the latest athleisure or any of these things. And I think if you take that mentality and apply it to music, especially in the era that Tyler, the Creator was coming up, so like late 2000s and like early 2010s, there was a certain type of hip-hop fan that was a bit more marketed to. You wanted to attract the type of a person that listened to Drake or listened to J Cole and Lupe Fiasco and Big Sean. But Tyler, the Creator was something a little different because he was much more the type to speak to the people in his words that would want to go to Taco Bell late at night that want to watch Aqua Teen Hunger Force and from a hip-hop perspective of this "nerd" or "off the mainstream path" type of audience isn't necessarily seen as the most sexy one to reach out to. The thing is though, if we're taking a step back, that group is still very much interested in following the people that they follow and likely times they're probably more so because they don't feel like they're represented by the mainstream. One, they're less likely to rely on the mainstream to tell them what's important. So they're more likely to feel much more die hard for the people that they rep as opposed to the people that may be fans of someone like some other artists at the time, just because those are the ones getting more mainstream luck. This is what I think worked out for Tyler and this is why I think his rise was much slower, but has been much more launch sustained and gradual than a lot of those other artists. Because as he's continued to grow and develop his craft over time, there were these inflection points you could look at when he put out this album called Flower Boy, I believe that was in 2017, for a lot of people that didn't necessarily either listen to Tyler or didn't necessarily have as much respect for him because of what they thought about him. They're now seeing him and his fan base is like, oh wow, here's this thing. They see that he's had this music festival that he had before music festivals really blew up into this ubiquitous thing that they've become in the past decade and be like, okay, wow, he's been doing this. He spoke to an audience that was seen as "less desirable at the time", but you fast forward. Now Tyler's the one who is headlining the biggest music festivals in the country. Tyler's the one that is selling out Madison Square Garden. He's the one winning best rap album and how he now has his merchandise companies where he's selling, Golf Wang material or anything like that. He's been able to do that pretty effectively.

Scott Rogowsky: Well, this is great. I have to wrap this up here, Dan. Cause I've got to run to Neiman Marcus for that Golf Le Fleur, Tyler collab. I picked that up, but before I do, it's time for Quizness Casual, the Business Casual quiz. Today's contestants, it's going to be my trusty co-host, Nora, and of course our guest today, Dan Runcie teaming up to answer questions all about legendary hip-hop artists. You ready, Danny?

Dan Runcie: I'm ready.

Scott Rogowsky: Let's get down to it then with Qumero numero uno: Which of the following hip-hop legends went to high school with Jay-Z? Ice Cube, Rick Ross, Busta Rhymes or P Diddy, AKA Puff Daddy?

Nora Ali: Do you know, Dan? He knows. He looks like he knows.

Dan Runcie: I know, but I'm I'm curious what you say first.

Nora Ali: No. See, this is collaborative.

Scott Rogowsky: No this is good.

Nora Ali: If I had to guess, I would say Ice Cube.

Dan Runcie: Okay.

Nora Ali: I don't know why though. What is it?

Dan Runcie: It's Busta Rhymes.

Nora Ali: Busta Rhymes.

Scott Rogowsky: That's right. It's Busta Rhymes. Actually Jay-Z, Busta Rhymes, Biggie, and DMX all attended George Westinghouse Career and Technical Education High School.

Nora Ali: Wow.

Scott Rogowsky: In downtown Brooklyn. Nice job there. Let's go with the next one, which of the following hip-hop legends wanted to open a soul food restaurant called Big Poppas? Bankroll Fresh, Pop Smoke, Young Dolph or Notorious B.I.G.?

Dan Runcie: This is tough. I'm actually not a hundred percent sure. Say the name of the restaurant again.

Scott Rogowsky: Big Poppas. I'll say this, it's not a trick question.

Nora Ali: Is it B.I.G.?

Scott Rogowsky: Yeah. The guy who liked it, when you called him Big Poppa wanted to open a restaurant called Big Poppa. Go figure.

Dan Runcie: It's funny though because sometimes with those, you could like overthink him because I'm thinking about like Dolph and I'm like, oh man, I know that Dolph was into the food. RIP and everything. So yeah.

Nora Ali: Thanks for the hint, Scott.

Scott Rogowsky: Exactly. Yeah. All right you're two for two. You're cruising through this thing here. Here it is, final question. Before settling on Lil Wayne, Dwayne Michael Carter Jr. originally went by what rap name? Ghostface Pacifist, Shrimp Daddy, Young Abner, or Snoopy Mate?

Nora Ali: I love our team for putting these together so much.

Dan Runcie: This is funny.

Nora Ali: How creative.

Dan Runcie: This is funny. What was the second one again? Is shrimp something?

Scott Rogowsky: Shrimp Daddy.

Nora Ali: Shrimp Daddy.

Dan Runcie: Okay. I think it's the shrimp one, but I could be wrong.

Scott Rogowsky: What's your reasoning on that?

Dan Runcie: It just sounds like something I may have heard before. I mean, because I know that it's funny. I had sent out some tweet recently about artists that have changed their names from some ridiculous name that they had had before. And I didn't see Lil Wayne's on there, but yeah.


Scott Rogowsky: Lock it in. Maybe Lil Wayne will open a seafood restaurant called Shrimp Daddy's because yes, Shrimp Daddy is what he once called himself taking inspiration from former cash money artist, Pimp Daddy.

Dan Runcie: Wow. OK. So we got it.

Scott Rogowsky: Pimp Daddy to Shrimp Daddy.

Scott Rogowsky: Dan Runcie, mazel tov.

Nora Ali: Crushed it.

Scott Rogowsky: Dan and Nora crushing it. Oh man, well that's a wrap on the quiz and that's a wrap on our chat about rap. Dan, thank you for joining us. This is great. 

Dan Runcie: Thank you so much for having me.

Scott Rogowsky: We love hearing from you, BC listeners, so like Chet said to Adele, hit our line. We're working on an upcoming episode about influencers. Who are your favorite influencers? Who do you want us to talk to about TikTok and Instagram and making money on those platforms? Send us an email at businesscasual@morningbrew.com or DM us on Twitter @bizcasualpod, that's B-I-Z Casual Pod.

Nora Ali: You can also leave a voice memo on our website, businesscasual.fm, or give us a ring and leave us an old fashioned voicemail. Our number is 862-295-1135. And as Business Casual grows, we are excited to get to know our listeners old and new. Drop us a line, and don't forget to leave your name and where you're calling or writing from, so we can hear from you in a future episode.

Scott Rogowsky: Business Casual is pushing P with Katherine Milsop and Bella Hutchins. Additional production, sound design, and remixing by Daniel Markus. Alan Haburchak is director of audio at Morning Brew. Sarah Singer's our VP of multimedia. Music in this episode from Daniel Markus and The Mysterious Breakmaster Cylinder. If you like what you heard, please follow Business Casual on Spotify, Apple Podcasts, or wherever you go for your ear candy. And we'd love it if you give us a great rating and a review.

Nora Ali: Thanks for listening to Business Casual. I'm Nora Ali

Scott Rogowsky: And I'm Scott Rogowsky.

Nora Ali: Keep it business.

Scott Rogowsky: And keep it casual.