Benjy Grinberg on Rostrum Records, Wiz Khalifa and Mac Miller, and Mental Health

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Benjy Grinberg, founder and CEO of Rostrum Records, looks back on his journey—how he left what others might consider a dream job to start his own music label. Rostrum has helped put Pittsburgh on the map with artists like Wiz Khalifa and Mac Miller. Benjy reveals what it has been like to work with those two artists, giving us a snapshot of how their careers took off. Tune in until the end to learn about some of the philanthropic things he has done.

If you want to know what it’s like to start your own label, this is the episode for you!

Episode Highlights:

[02:40] About Pittsburgh’s music scene

[03:24] Benjy’s transition from L.A. Reid’s assistant to independent music producer

[07:05] How he met Wiz Khalifa and their trajectory to success

[11:40] On handling different duties at the same time

[17:41] The challenges of releasing mixtapes on streaming services

[25:52] On doing deals with artists and major labels

[37:40] The importance of giving back and mental health awareness

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Host: Dan Runcie, @RuncieDan, trapital.co

Guest: Benjy Grinberg, @benjybenjy, Rostrum Records

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.

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Dan: Hey, welcome to the Trapital podcast. I’m your host and the founder of Trapital, Dan Runcie. Today, we got a special guest and I’m really excited for you to listen to this interview. Had a great conversation with Benjy Grinberg who is the founder and CEO of Rostrum Records. Rostrum is one of the few record labels that I could say that it put its city on the map. Rostrum put Pittsburgh on the map from a hip-hop perspective, with artists like Wiz Khalifa and Mac Miller and we talk a lot about that in this episode. Benjy breaks down the founding and the start of Rostrum 18 years ago which is when he decided to leave what many would have considered a dream job. Benjy was working for L.A. Reid early in his career in the music industry and said, “Nah, I’m good with all that. Let me go do my own thing and build something really special.”

We talk about the rise of Wiz and him releasing iconic mixtapes like Kush and OJ. We talk about Mac Miller too. And then Benjy also talks about some of the challenges there. He talks about the relationship with Wiz Khalifa and where things currently are between the two of them and he also talks about Mac Miller and just how it’s been losing not just his business partner but losing a friend, considering all of the great stuff that they were able to work on together. I appreciate how open he was in sharing that but also talking about himself too and it’s real. As a founder, you’re starting businesses, it can be one of the most stressful moments of your life, believe me, and Benjy has been a strong advocate for mental health awareness and how important that can be so we talked about that and some of the more philanthropic things that he’s been doing since. So, I hope you really appreciate this episode. I know I did. Here’s my conversation with Benjy Grinberg.


Dan: We have Benjy Grinberg who is the founder and CEO of Rostrum Records and he’s one of the few people who I can say helped put a city on the map, helped put his own city on the map in Pittsburgh. That must feel good to think about once in a while.

Benjy: Yeah, it is, but I’m only a part of it and there was a bunch of us working together to make it happen but I was really glad to be a part of it and I still continue to try to rep for my city.


Dan: I feel like it’s one of the few cities that I think, especially in the past like 10, 15 years, that has been able to like come and has been able to like stay, because I feel like a lot of cities, especially cities in the Midwest and middle of the country, they’ll go through waves, right? But I do feel like Pittsburgh has steadily been there ever since you all were able to at least pop and keep the momentum going. 

Benjy: No, definitely, and, look, Pittsburgh actually has a rich jazz history. It has a rich history when it comes to, you know, rock from maybe the 70s and 80s, etc., but it was really, you know, and, definitely, even with hip-hop, you know, some people have come out of Pittsburgh to be great producers and all that kind of stuff, but, really, with, you know, Wiz kind of leading the way, you know, really putting us on the map for, you know, modern music, for sure.

Dan: And you had started Rostrum back in the early 2000s and at least from what I’ve read, at that point, you would had — you’re working with L.A. Reid and I think a lot of people would be like, “Oh, that’s the dream job,” you have the big name exec everyone knows, but you wanted to start your own label. What was that decision like and was it an easy one to make that move?


Benjy: So, I was young and naive, right? It was like, you know, I had just graduated college, I moved to New York, was sleeping on my brother’s sofa, trying to figure out what I was gonna do, you know, but I wanted to work in music and I needed to figure it out and I first started working at this early web casting company that webcast concerts and I was there doing artist relations for a couple of months and I won’t go into the whole story about how I got in the door with L.A. but I became L.A. Reid’s assistant and when he took over for Clive Davis at Arista and it was like, “Holy fuck,” like I was like thrown in the deep end of the music industry and it was exactly what I wanted and I couldn’t, you know, when you graduate college, what’s your like ideal job? Like I wouldn’t have even thought of this as a possible job for me at the time.

And so, when I got it, it was such a big deal for me and I really just tried to do the best job that I could while I was there and what I wanted to do while I was his assistant was to be an A&R person so he allowed me to start being in the A&R meetings, I could bring in songs, I could bring in artists to audition, etc., and I was like, “Okay, I’m on my way to being an A&R person here,” but, as it goes, you know, sometimes, when you start to reach your goal line, the goal line changes, right? So it was like, well, at the same time, I was writing and producing music and I was working on this project that I was really passionate about that I knew wasn’t a major label project and I just decided, like I’ve always been entrepreneurial, like why don’t I start my own record company and I can do this project, which was called Top Shelf 1988? So I literally left Arista to start Rostrum in 2003, it was March of 2003, to do Top Shelf and to focus on developing things that I wanted to develop, you know, passion projects, and also to continue my goal of writing and producing music and it just so happened that the label started to take off faster than me as a producer and so that’s kind of the route that I continue to go in.


Dan: Nice, because I feel like, for a lot of people, I know tons of people have tried to start record labels and it can come from a place of trying to be more lucrative or you’re just trying to go after the money, but you more so were like, “No, I was interested in doing the side project.” You’re focused on the art and then the business side of it just happened to take off a bit from there.


Benjy: Well, yeah, it wasn’t a great business decision at the time, right? This is right as the music industry was starting to tank, you know, to be honest, and so it was a horrible time to start an independent label and I was coming from it from a place of, there’s this music that I wanna work on and artists that I wanna work with and I didn’t see myself spending many years kind of working my way up the corporate ladder. It just kind of wasn’t for me and I just wanted to take a chance on it and, like I said, I was young, I was 25, and I had no real responsibilities in terms of a family or anything like that and so I gave it a shot and it ended up panning out. But it wasn’t before many years of bootstrapping and, you know, working night and day and moments where I was like I don’t think that this is gonna work out and times when you’re like, “I’m not sure I’m gonna pay the bills next month, maybe I shouldn’t keep doing this. Maybe I should be a music teacher, maybe I should…” you know what I mean? Like just so many different thoughts when it’s not going well of what else you should be doing and is this really the right thing to do and so, it was really the persistence and the belief at that time in Wiz that kind of kept me, you know, sort of pushing through with everything.

Dan: And then what was that moment for Wiz that had kept you going? Was it when “Say Yeah” had come out or…?

Benjy: No. So, I had met Wiz in Thanksgiving of 2004 and he signed to Rostrum in early 2005 and, you know, we were just doing our thing independently. Like he wasn’t the Wiz obviously that you know now, like he was a high school student, you know? Like — that I thought was really dope. It was obviously a different time in the industry. It’s not like we were just like making records and putting them up on SoundCloud or something like that. It was just a whole other thing. And so we held hands and took this journey together, you know? Like we believed in each other. But it took a bunch of years to really get going. We released some independent mixtapes and albums that, you know, did okay and got his buzz up and then Warner Brothers came calling and it was at Warner Brothers where we did a couple of singles. Our deal there was a couple of singles into a potential album and so we did three singles there, “Say Yeah” being one of them. But, yeah, when Warner came calling, that was, you know, a really important moment for us, but the songs only did okay at that time. We didn’t see eye to eye with Warner Brothers as to the approach and how they were supporting us, and they were great people but it just wasn’t the right match and we decided to go back to being independent again, you know?

They let us go, we went back, you know, and it’s like, all right, you know, before Warner Brothers, we’re going up, up, up, when we hit Warner Brothers, it felt like we were starting to stagnate a little bit, and so when we went back independent, it started going up, up, up again and so we knew that we were on the right path. But even when it’s going up, you know, you can look back at it now and say like, “Of course it was gonna end up being successful,” but, you know, it can go up for a while and then plateau and then go back down, like you don’t know exactly what the graph is gonna look like, you know? And so, even then, when things were going well, it’s not like a ton of money was coming in or anything like that, you know? Starting to buzz and this, that, and the other but it’s still hard and there were still periods during that time that, you know, we were kind of unsure about where this was all gonna go. And then it started to take off, like 2009, 2010 it just went crazy and it was honestly the moment I’m talking about when I’d seriously considered like should I be like a music teacher or something like that was right before that so it was like after “Say Yeah,” you know what I mean? After we had been through all of that that those questions still were there.

Dan: So, it seems like by the time that Kush and OJ came out, it was like, okay, no, we have this in motion.

Benjy: Oh, yeah, we were already really going. I mean, deal or no deal, you know it was a great project that helped to take it sort of, you know, to the next step and — but all the while, the mixtapes were really like generating a lot of buzz. The touring, which was a big aspect to our approach, you know, back then was really helping to build his name. And, by the time Kush & Orange Juice came out, we had already sort of quietly just signed to Atlantic and so, you know, things were going by then to the sort of fever pitch of Kush & Orange Juice just coming out, you know? And then “Black and Yellow” and then, you know, all the other stuff and so it just kind of went crazy from there.

Dan: Yeah. And that Atlantic piece reminds me because I remember around that same point, I know that Rick Ross had hit up Wiz to try to get him to come to MMG. Was that close to happening at all? Like, from your perspective, what was it like at that moment and was that a possible option?

Benjy: I don’t remember exactly but this is — I actually totally forgot about that. The thing is is that when you start to become successful and you’re a buzzing artist, people are gonna come out of the woodwork, not that Ross is coming out of the woodwork, but people are gonna come from everywhere to try to pick you up, you know? On many levels, like, you know, management, label side, production company side, you know, indie side, whatever, and it’s actually part of, you know, it’s nothing that I ever partake in but it’s something that, when I was witnessing it, it felt hurtful, in a way, and, again, I’m not talking about the Ross one, the Rick Ross one, I’m just talking about in general, like, you know, people trying to talk to Wiz behind my back or, you know, like that kind of stuff. It’s like, yo, we’re a team. We’ve been working together for five years already, you know what I mean? We’ve been putting in blood, sweat, and tears, you’re gonna try to go, you know what I mean? Like that part of the industry always seems super fucked up to me but it is a part of it and, you know, to Wiz’s credit, like, you know, he felt like he was on the right path, you know what I mean? And we stuck by each other through the whole thing, you know, and never faltered or never sort of went in any other directions and, you know, that was really important and, you know, a lot of success came from it as well.

Dan: Yeah, because at that point too, he was doing his thing, Mac Miller came on board, so you had the two shining stars of this city on the same label. You’re doing your thing.

Benjy: Yeah. It was a crazy time. It was a crazy time. And, you know, we were handling a lot of different duties at the same time as well. It wasn’t just like, you know, we’re just a record label, whatever, like we were really helping to handle, you know, business across the board and so it was very hectic, it was very hard, and it was a bit of a blur at times, you know what I mean? Even looking back, you know, like you just mentioned the Rick Ross thing, like I didn’t even remember that, you know what I mean? It’s just like you have like 10 balls in the air that you’re juggling, you know what I mean? And you’re just like that’s all you’re focused on and so, yeah. I mean, looking back on it, it’s like, wow, what a crazy, amazing time. Not that I couldn’t appreciate it at the time but you can always appreciate it better afterwards, you know? To say like, wow, we really did all of that stuff. And so, yeah, it was crazy and it was great.

Dan: And I know you’ve spoken too about just how much work it was at that point, because you didn’t just have these two stars on your label, you were also managing both of them — and navigating all of that, like was there anything you think that you would have done differently? Because I know you said that it was a lot to manage and you may have either tried to focus on one particular area over the other.

Benjy: No, I think it went really well, you know what I mean? And I think part of it was like the frictionless way we all kind of worked together and so the way that it happened was so when Wiz signed to Rostrum in 2005, he was managed by somebody else. His name’s Chad, great guy. Chad was his manager. Two or three years later, they separated and so I tried to help Wiz get introduced to other people. We reached out, I think his lawyer reached out, like we were just trying to find a new manager for him because I wasn’t trying to be a manager, to be perfectly honest with you. I wasn’t interested in being a manager.

Dan: And what was it about management that didn’t interest you?

Benjy: I just — I wanted to make records, I wanted to build a record company, like that’s what I wanted to do, like that’s what I was here to do, you know what I mean? And so management had never even been part of my consideration at the time. There was — no great fits were happening and so he said, “Well, can you just do it? You know, would you do it?” And I said, “Well, I’ll do it just until you find somebody, you know, that you like just so that we don’t drop the ball on anything and, you know, I’ll help,” and that situation lasted six years, you know? So it’s like 2008 until 2014, I was the de facto manager. We didn’t have any management paperwork. There was nothing separate from what our Rostrum deal was. It was just like I’m gonna take on all these additional responsibilities and so it was a lot but once we got into it, you know, a few years into it, I was like, (a), I feel like I’m really good at this and things are going really well so why change it, you know? At any point, we could have changed it, but like it was just sort of like I think we were both like, “This is going well,” and we kinda kept it going until we separated in 2014.

And so when I started working with Mac, it was the same exact situation, you know? He had his guys around him who were helping to guide him and they were great. They always remained on board throughout his entire career, even after he left Rostrum, but he was looking at what we were doing with Wiz and he was like, “Can you do the same thing with me?” you know? And so it was the same kind of situation where it was just a record deal, if you will, on the Rostrum side, but we helped handle a lot of other responsibilities because he wanted us to and I think even in the deal, just like, “At any point, you can have any other manager that you want but we’ll help out and do it as much as you need us to,” and so that was just kind of the situation until the beginning of 2014 when our deal was up and he decided to switch it up a bit.

Dan: And how are things with you and Wiz now, from a relationship perspective?

Benjy: From a relationship perspective, it’s cordial, you know? We hit a rough patch in sort of the mid 2010s and it was really one of the hardest times of my life, to be perfectly honest with you, and, particularly after working together so hard for so many years, it’s like — it’s almost like a marriage breaking up, you know, if you will, and so that was really hard for me and so after that kind of all calmed down, you know, it’s just like we’re cool but like it’s not like we hit each other up all the time or anything like that. But, you know, we still have business together, like we still have all these records that we made together that are part of Rostrum and a part of Wiz and so we have business to attend to and stuff like that but it’s pretty much at arm’s length at this point. 

Dan: And I feel like, or at least personally, I always feel for the people in your position with these because there’s so many times where I feel like an artist either parted ways with the label that they started with or the manager that they started with, so much of this seems quite common in the industry, but it’s easy for people in your position to be like, “What did I do wrong? What happened?” when, unfortunately, it’s kind of part of the game. It almost reminds me of like a sports coach, like an NFL coach, right? Like you’re gonna get fired at some point, unless you’re Mike Tomlin or like, you know, Bill Cowher, one of your Steelers coaches that are there for decades, but that’s the way I’ve always thought about it.

Benjy: Yeah, and when those situations happen, you know, you read about it or you hear about it, like so and so broke up with their original team or whatever, like, you know, you always feel for that situation and, like you said, a lot of times, it’s kind of bound to happen at some point but it also makes you really respect the ones that have stayed together forever. There’s some teams that stay together forever and keep that going and so you have to give them a lot of respect for keeping it together the whole time.

Dan: And you had mentioned there too about the fact that you and him still have business together so that, of course, keeps things cordial and I’m sure a lot of that is related to the mixtapes that you’ve been able to put out a rerelease. Kush and OJ was recently put out, like I’m sure that’s great. And I’m curious from your perspective, like how much work and what has it been like trying to get some of these classic mixtapes that fans love on the streaming services, especially tapes like those?

Benjy: So, it’s a challenge, right? For a number of reasons. One is, sometimes, back then, when you’re doing mixtapes, you know, you might be working with local producers or somebody that the artist met online or whatever and so just getting back in touch with everybody sometimes to make sure that producer deals are right and that everything’s worked out the way they need to be, the side artists, that’s a challenge in and of itself. Obviously, just from a logistics standpoint, like making sure you have all the files and everything you need to make sure that you can put it up correctly. But the biggest challenge and the thing that takes the most time is the samples. And so, in particular, you know, Kush & Orange Juice has samples all over the place and so that’s what takes the most time is clearing the samples and that’s honestly what the biggest expense is as well because just to clear one sample can easily be $8,000 to $10,000, and then so you multiply that by every song, you know, and sometimes, I think there’s a couple of records on Kush & Orange Juice that have two samples, you know? It’s just — it can be a bit of a nightmare.

But, to me, one of my guiding principles in clearing these mixtapes for Mac and for Wiz is to try to keep them literally exactly the same as the fans listened to them in 2010 or 2011 or 2012, whenever they came out, and so, to me, I’m willing to spend whatever I need to spend or work as hard as I need to work so that when they push play on Spotify or on Apple Music or on Amazon, that it’s the exact thing that they remember listening to back then because that’s part of it, right? The nostalgia. We don’t even go back in and remix the songs, right? We remaster them. We remaster them so they’re a bit louder or so that they fit in with everything that’s on the DSPs but we don’t touch the mixes purposefully so that it sounds exactly how it sounded.

And so, all that put together is really kind of the biggest challenge. To clear a mixtape, you know, it’s easily $150,000 to $200,000 just on the expense side, not to mention everyone’s time and efforts, etc., and then you have to figure out, you know, what’s the best way to — I hate to use the word “market” it but like, you know, what’s the best way to reintroduce it to the fans, to let everyone know that it’s out but to do it in a tasteful way, you know, and do it in a cool way and that’s something we worked closely with Wiz’s team and with Mac’s estate now on, again, let’s hold hands and do this together, like, “What do you guys think is cool? This is what we were thinking about,” but making sure that everyone feels invested in it and feels like whatever we’re doing is cool, you know?

Dan: And with Kush and OJ, were you able to get all of the songs cleared? I’m trying to remember what it was like with that release.

Benjy: No, we couldn’t get the Demi Lovato sample cleared with Disney so that sample, which is one of the earlier songs and it sucks, couldn’t be on there. And “Never Been,” I believe, is one of the ones that — and this is what we do. For instance, I think it was “Never Been,” it’s a song produced by Sledgren, it had a sample that we just couldn’t clear, it was from — I think this is right but it was from like an anime thing or video game — it was something that they just said, “No, like you can’t sample this,” and then we’d go back like, “Please,” and then, “No,” and then, “Pretty please?” you know, and, “No,” you know, because we don’t just accept no. It’s just like, come on, what’s the reason? Is there something we can do? Is it the language? And, you know, it’s just no, no, no, no, no.

Dan: Did they give you any reasons though or…?

Benjy: I’m trying to think in that case, sometimes, you know, I’ll speak more broadly about it, sometimes, samples are denied because the original writers just don’t like hip-hop. Sometimes, they don’t believe in their work being repurposed in that way. Sometimes, we’ve had samples not get cleared because of the language that’s involved so there’s swear words or they’re talking about drugs or something like that, you know? The original writer may not want their work associated with that. And so those are usually the reasons why it wouldn’t be cleared. In this case, with the one we’re talking about on Kush & Orange Juice, I think it was literally like it was something on their side with a video game where it was just too difficult for them to even start to try to figure it out on their end that they said like, “We can’t do it,” you know? And we offered to help in many ways and we couldn’t but so, in that case, what we do is we go back to the original producer, in this case, Sledgren, and say, “We’ve tried everything, we cannot clear the sample, you know? Do you wanna have a go at remixing it or redoing it in a way that is okay?” and so that’s what we do in those cases. And if sometimes it’s too hard, like the Demi Lovato situation was literally her voice — it’s not just the sample but it’s her voice as part of the hook and whatever and it’s just too difficult, unfortunately, every once in a while, but it’s really every once a while because we usually get most of them, we just have to take it off.

Dan: Because I remember when it came out and I saw that there were two off, I was like I am sure that they tried everything to make this happen and there’s just nothing that they could do.

Benjy: Yeah, no, it’s, you know, we tried everything and it’s just sometimes the answer is no and, at some point, you have to accept it and not hold up the whole tape for something that you really feel like is a dead end and keep it moving. But we do try very hard and are quite disappointed when it doesn’t work out because, like I said, like the art of it, the full composition of the mixtape as it was, is really important to me as it is to the artist and so really wanting to, you know, preserve it in that way is really important to me.

Dan: And I’m sure that, on the flip side, doing it with Mac Miller and his mixtapes, I’m sure that also has its own challenges because, (a), you mentioned you’re not working with him anymore, you’re working directly with his estate and I know that doing things posthumously also has had plenty of challenges in the music industry. Then there’s also the emotional pieces. This was someone you had a very close relationship and a bond with over years and you’re trying to recapture a lot of that.

Benjy: It’s very hard at times for me to listen to Mac, as much as I love that music and how much of a part of my history that music is as well and all that other kind of stuff. But like, for instance, even his Circles, his most recent album that they released posthumously, like I listened to it once the day it dropped. I wasn’t involved with the making of it or anything like that. I listened to it once and I’ve never listened to it again, to be honest, like it’s just a little too difficult for me.

And with the mixtapes, I listened, you know, for whatever reason, it’s a little easier. It’s like kind of like feel good nostalgia, like it makes me feel good to think about him in that period but it’s still difficult and, yeah, I mean, look, we don’t do anything without talking to his mom, his lawyer, the Clancys, who managed him when he passed and continue to manage, you know, his music and his estate — I don’t know that they manage his estate but they managed him as an artist, and make sure everyone’s okay with whatever it is, like, for instance, you know, before he passed, he really wanted us to clear K.I.D.S., right? And so that’s what we were working on. And so it’s obviously a no-brainer as to like the fact that we’re gonna release K.I.D.S., right? Like everyone wants that to happen. But, the timing of it, you know, like what else do you guys have planned, you know? Because they were still doing stuff with Warner Records and they have their own things and their own schedule that they’re doing so like really fitting into where it makes sense for them and just being really respectful of it and just doing the best we can with it.

Dan: On the other side of that, though, I feel like, even though, you know, so much of this and so much of this conversation is focused on Wiz and Mac, specifically, you’ve been able to help bring in, you know, a new group of artists, specifically from Pittsburgh, but also being able to expand beyond that too. And I’m curious, how different is it now, as you’re trying to continue to have the record label on the map, you’re attracting these artists and the type of deals you’re having with them, versus some of the deals you may have had with Wiz and Mac and others? Because I look at this era now and I feel like now there’s so much more discussion of, “You have to own your masters, you have to do this,” and — SoundCloud and all these things, like how has it been from your end?

Benjy: It is a different time. The deals are somewhat different. In general, we’ve always done 50-50 deals. So, as an independent label, you know, that’s just kind of always what we’ve done and then, sometimes, you know, it’s 50-50 and then, each album, maybe it goes a little bit more in the artist’s favor or whatever it is, but it generally is 50-50. And so, today, for the most part, it still is 50-50. The difference is that, these days, there’s a lot more competition, I guess I would say, and not just direct competition but just so many different ways that artists can go about what they do, right? That, you know, like I said, in 2005, it’s not just like, you know, “I’m gonna, you know, put my stuff up on TuneCore and just like get it out,” you know?

Because I think none of the DSPs even existed in 2005 and so it’s a different time, like earlier on, you needed a lot more of a mechanism to get it out. You needed distribution and you needed to press up CDs and there were a lot more costs involved. And, back then, the typical deal was very much, you know, like a sort of 360 but it was kind of different in our case, like we never took publishing rights or merch rights or anything like that. With our artists, our main thing was the records and, on ancillaries, such as publishing, merch, touring, well, when we participated, it was always on a passive basis, right? Which is like you go do your own touring deals, you go do your publishing deals, you do whatever you want, you’re free to do whatever you want, we don’t own that, you do, but because we’re spending a lot of money marketing, we’re making the music that’s driving all of that stuff, we want a passive participation, you know, in it, and so that’s what it was back then and, today, 50-50 but we don’t even talk about ancillaries, you know? Like we don’t even ask for passive participation in anything.

It’s like, “Look, we’re gonna make music with you. We’re gonna release that music, we’re gonna market that music, and we’re gonna get it out there and we’re gonna do everything we need to do, and, for that, we’re gonna participate in that music,” right? “You go off and do whatever you want on all that other stuff still and we’re not even gonna take a piece of it,” and part of that is to differentiate yourself from the major labels who is our main competitor. It’s not other indies, its major labels. All of the artists we signed in the last couple of years were being looked at by majors and by us, you know, and they ended up coming to us. My goal in Rostrum has always been to build an alternative to going into the major label system and being able to do it with similar resources but independently.

And so, to me, it’s like, all right, but how do we differentiate ourselves? You differentiate yourself, (a), by just being very hands on, by caring, by putting a lot of love in it, and by keeping a small roster so you can really focus on everything, right? There’s no politics, there’s no shelf at Rostrum, right? Like you don’t get signed and just get like put on the shelf. We don’t have a shelf, you know what I mean? It’s like, if we’re working together, we’re working together. Let’s put out music, let’s do our thing, right? So part of it is that. Part of it is shorter-term deals, right? So, one-, two-, three-album, you know, album situation and I can, if you’re interested, tell you how we define albums at this point — but doing shorter deals, right? Whereas like 10 years ago, it might have been six albums or whatever.

And the other is that we don’t ask for, you know, non-record income so all the other stuff that we talked about and so that makes artists feel really comfortable, as it should, and — but it really puts the pressure on us, you know, for the records to perform, right? Because some artists like the records do okay but they do great touring or they do great over here, whatever, you know? For us, we really wanna make sure the music’s great and really wanna make sure that we’re doing everything we can to make sure that as many people hear it as possible.

Dan: And you feel like, because you’re competing with a major record label for a lot of these artists, do you feel like the pitch is pretty easy from an offer perspective? Because I’m sure you’re not just selling them on the terms, you’re selling them on like what you can offer and track record. Do you feel like it’s been relatively easy to like get that pitch across to them? Like relative to some of the major label options they may consider.

Benjy: When artists, you know, not to sort of pat ourselves on the back, but when artists meet with our team and sit down with us, very often, and I don’t ask this out of them, like, “So, how does this meeting compared to other meetings?” Like, you know, but we’re having our regular meeting, you know, we’re talking about their goals, what they’re trying to accomplish, how we can possibly help them with all that, and, at the end, oftentimes, sort of in an unsolicited way, they’re like, “Man, this meeting was so much better than all the other meetings that we’ve had, like I feel so much more comfortable,” this, that, or the other. It’s because like, you know, first of all, we’re music people, like this is what we care about. We care about the artists, we care about what they care about and how we can help them with that. And I think we kind of talk to them in a different way, like I’m not sitting in on these other meetings that they’re having but they don’t wanna hear about analytics, they don’t wanna hear about this, that, or the other.

They wanna talk about the music. They wanna talk about what their dreams are, what their goals are, and that’s really, you know, what we focus on and how we connect because people wanna feel comfortable with where they’re going, you know? And, to us, it’s not an act, it’s not something we practice, it’s just like — it’s just kind of who we are. And so I think that that’s, you know, a point of differentiation, you know? We don’t even talk about the deals in our meetings, right? Like, “So, if you come to Rostrum, we’re not gonna ask for…” you know, like that’s not part of the conversation. Let’s talk about music. Like, “Let’s talk about what you’ve done. What have you already tried? Like, you know, when you did this,” you know? You’re just trying to find out more from them so that you can see, (a), if we’re the right fit for them, right? And it’s a two-way street, like do they feel comfortable with us and do we feel comfortable with them, right? And because we’re gonna work together really hard over the next couple of years or however long our relationship is and so you wanna make sure that you like them, like as people, you know, that you can work with them, that you feel good about it.

And it’s the same way, I think, about hiring. When people join the team, it’s not just, “Hey, can you do this job?” Are you a good person? Like do I wanna talk to you every day? Do I want you representing the company that I started? Do I want you representing the artists that are trusting us with their music to go talk to the partners? Like that is really, really important to me and that’s a lot what I think of when bringing people on the team. And so it’s just kind of a different approach. I’m kind of forgetting your original question that got me here but I hope I answered it.

Dan: No, that was good. That was good, yeah, because I was really curious about that pitch, right? Because I’m sure that artists are often comparing, “Okay, do I wanna try to become a superstar and if I wanna become a superstar, they have the distribution and the money. But if I really want people to care about the music,” and I know this is a very reductive comparison, but like, “If I want people to care about the music and actually care about the art and can back me and won’t shelve me, then I wanna go with the independents and the folks that I feel can be most connected,” right?

Benjy: Right, for sure, but there isn’t that exact line between the two, right? Like we can accomplish both of those things and it is possible to do both those things and that’s why I talk about independent not meaning small, you know? When you think independent, it doesn’t have to be small, it’s just independent. If we have a song that’s going, we’re gonna continue to invest a lot of money and resources into taking it as far as that song will go. But, look, the major labels, I’m not a major label hater. I have a ton of friends that work in the major labels. It’s not that. It’s literally just a differentiation between the two. But the major labels are absolutely right for certain artists, you know, and for certain things and they’re absolutely not right for certain artists and certain things, the same way that Rostrum is, right? Like we’re right for certain things and we’re not right for other things and that’s part of the meeting, right?

Is to find out from both standpoints, is this the right marriage, you know? And so I think that there’s a right home for everybody and it’s just trying to figure out in these meetings, it’s not a pitch like we don’t even try to sell ourselves, it’s like let’s try to make a connection, you know, and see if we like each other, if we feel the music. Can you play the music that you feel like it’s gonna come out next, you know, and do we see eye to eye on sort of what that direction is and, you know, all those sorts of things play into whether we decide to work with someone or someone decides to work with us, you know?

Dan: Have any of the majors tried to acquire you? Because I feel like that’s a trend I keep seeing of like so many of your peers that are either getting acquired and I know aggressively they’re trying to find all the hot indie labels so that they have the pipeline. 

Benjy: So, when Mac and Wiz were really taking off, 2011, 2012, like calls from everybody, you know, like, “We wanna buy 50 percent of Rostrum and do this, that, or the other,” you know, whatever it is, and I just always said no, like we were doing something special. It didn’t feel like the right decision at the time. I was also getting offers just separate from Rostrum to run major labels and things of that sort that I said no to as well because I believed in what we were doing and, at the time, I was managing Mac and Wiz and doing all that kind of stuff and I was like no, like I’m on this journey with them, like I’m not gonna just veer off and go try to run a major label.

And then I said no so many times that I think people like stopped asking because I think they already knew the answer, but with the market being what it is now and with our continued success and our continued sort of proof that we can do what we do, those conversations have definitely started up again where it’s like, “Hey, we know a number of years ago you were not interested, like are you still not interested? Or, you know, is there a discussion to be had?” And, you know, look, I’ll have a discussion with people but I’m not trying to make any moves that don’t feel right, they don’t feel right for the records that we represent, the artists that we represent, and the feeling that we represent. And so, to me, that’s really a driving force in all of this. And I’ll hear people out and see what people are talking about but I’m not quick to do anything and I’m certainly not gonna do anything that I don’t feel is right.

Dan: Yeah, that makes sense. And I feel like, from outside in, I feel like you’ve made the right call with all of this, just given the success you’ve had and everything else there and I could also relate to this to some extent as well as someone that does get hit up and reached out to by whether it’s outside investors or whoever else that either wanna invest in Trapital or try to acquire it. Same type of thing, right? I mean, I know where the vision is, I know where things are heading, and, you know, you’re always willing to have the conversation and talk it out and it’s not one of these like hard stamp no things but you know when you have something special.


Benjy: No, absolutely, and I appreciate that and I appreciate you having me on, by the way, taking a quick second. I was excited that I was invited to come on because I check out your newsletters and all the things that you write and I think you’re doing a great job and a great service in educating people and so I’m happy to be here, by the way.

Dan: Yeah. And I know we’re getting to the tail end of this but before I let you go, I did wanna highlight one of the things you’re doing that I think is dope. You have the Benjy Grinberg Scholarship. I think it’s really cool that you were able to — this is your way of trying to give back and being able to show the focus of education, obviously, just given how crazy tuition and everything else is, I feel like the ones that provide access to people who don’t have it necessarily is really powerful so I think that’s dope.

Benjy: Yeah. Well, thank you and, look, you know, my wife and I do a lot of stuff behind the scenes, a lot of stuff that we don’t publicize at all, and I was actually hesitant whether to post about the scholarship, you know, online and everything, but because that this particular thing can be, you know, you can apply for it, it made sense to me to post about it and let people know about it. But, really, it’s, you know, I feel very blessed in what I’ve been able to accomplish and some of the things that come along with it and I am very sensitive to other people not having that chance or not having the same resources in various ways, you know?

And we’re passionate about helping to fund music programs in Pittsburgh and at the Children’s Hospital in Pittsburgh, we help fund the music therapy program and there’s a lot of things that we do but I don’t, even though I’m talking it about now, but I don’t love talking about it because, to me, that’s like it’s something that feels important but it’s not something that you necessarily trumpet. And the only time that you trumpet it is — and I’ve had to learn this because I’ve always been like no, like just put it as anonymous or do it as this and the people that are behind it are like, “No, we’d really love to use your name,” because it helps other people sort of figure out, (a), that they can also do this thing and it brings attention to the program and this, that, and the other and I’m like, “Well, if you think it’s gonna be helpful, like I’m down,” you know, but I just don’t want it to look like I’m just out here, you know, like I said, sort of yelling from the mountaintops about those things.

But with the scholarship, back to the original question, this is the first year. It was a smaller amount and, each year, we’re gonna make it bigger and bigger as we grow into it and sort of find our footing with it and education is something that’s really important to me. I feel really blessed that I was able to have the education that I had. And, yeah, it’s just important to give back and care and I hope that it helps influence other people to do the same, if they’re not already. Because there’s a lot of great people doing a lot of great things and so I think sometimes people just need inspiration or need to hear what other people are doing to come up with their own way of giving back, in whatever they can. Sometimes, people don’t have money that they can give, you know, maybe they can give some time, maybe they can give of their own expertise, you know? It doesn’t — it’s not just money. And people just need to know that you care.

That’s part of my whole push with mental health advocacy is sort of the same thing. It’s like showing people you care, showing people, you know, trying to normalize the fact that we all go through different things and we all have issues at different times and that it’s okay to talk about it, to sort of normalize it so it’s not so weird or whatever, you know? That’s another thing that I’m really passionate about sort of inside the music space and also outside the music space is trying to normalize that conversation as well.

Dan: That’s powerful and thank you for that. I feel like that’s an important one. It’s great to just see more awareness and discussion about that overall but — especially in the music industry, it can be so stressful and even some of the moments that you had shared that you definitely had either struggled or had frustrating moments in your life dealing with all of the ups and downs from running a record label, dealing with artists that you had as close relationships, I’m sure all of that, you know, speaks to that experience too.

Benjy: No, for sure, and particularly — I think a lot of people that are artistic or have that talent in them, I think sometimes anxiety and other things go hand in hand with those talents and so I think, in our industry, it’s probably even more prevalent than in other industries, given that fact. But, to me, I think it’s something that behind the scenes or executive or however you wanna say it level, I feel like at least for a period, I think it’s getting better now, but for a long time, it was always like you had to kind of seem totally, you know, together all the time. Like, sure, I can handle a million things and, yes, I got this, you know, sort of the old time sort of like maybe if you picture it in a movie, like an old movie, like an old like movie exec or something like that, like someone who has it all together and can do this, that, and the other, nothing bothers them and, you know, I feel like we are all sort of putting up a front, like, “Yeah, everything’s great,” you know, this, that, and the other, everything’s awesome.

And it’s like no, not everything is awesome and, like you said, the music industry can be very, very challenging. You put a lot of your person into it, like a lot of your personality, a lot of your creativity, a lot of your passion and sometimes that’s rejected, sometimes, you know, relationships fall apart, whatever it is, that can really have an effect on you as an executive, you know, not just as an artist but as an executive, and so I think it’s important to say — like it’s okay to say, “No, not everything’s okay right now,” or, “I think I might need a little bit of help,” or, “I need to take a breather, you know, for a little bit just to like get my mind right and have some space,” and it was when I was diagnosed with OCD that kind of made me realize that I need to share this in a way, right? Like I’d always hidden it so much, right? All of my anxieties, my OCD tendencies, different things like — but when things got really, really busy and when things got really, really successful, it reared its head in a way that it had never reared its head in my life before and I was diagnosed with OCD and it was one of those things where I said, you know what, I’m tired of hiding all of this, you know?

Like I wanna talk about it because I want — I’m sure other people are going through it and I wanna make them feel less alone because I was feeling really alone, in a way, and so that became a really important thing for me was taking that leap of faith and that uncomfortable step to say, “Hey, I’ve had mental health challenges before and this is some of the things that helped me out,” and if you’re having problems, you should do whatever feels right for you to get through them, whether it’s talking to family or talking to a therapist or if you need medication or you need to take a break or whatever it is, that it’s okay, like it’s okay and I’m still here talking about normalizing it because it’s still important to me, because it’s still something that I wanna continue talking about even a couple years later so that message continues and that maybe other people will trumpet it as well and continue to talk about it and, look, I think things are getting better. I think people are more aware of, you know, mental health issues and awareness and all that kind of stuff and so I think we’re headed in the right direction.

Dan: Yeah. I think we are too and I appreciate your bravery in using your platform and your voice to speak from your own experience to make this happen and like to help educate others. I think this is how things continue to evolve so thank you for that. And I think, in general, you’ve just dropped a lot of insights, both from your own experience, how the industry works, and just going through the steps and I think people definitely get a lot from this episode but, before we do let you go, Benjy, is there anything else that you wanna plug or let the Trapital audience know about?

Benjy: That’s a good question. No, I mean, you know, I love talking — I don’t do it very often but, you know, I’ve always sort of been very much behind the scenes and, more and more, I feel like I have something to offer in sort of my experiences, like I just said, with mental health, but even with the music industry and things to avoid and the best ways to go about it and so I love talking to people or answering people’s questions or, you know, just being more vocal about, I put this in quotes, the “right thing to do” in the music industry and so it’s more so just sharing my experiences and my knowledge is kind of what I’m here to do right now.

But, you know, look, we have a lot of exciting artists coming up and I feel like if I start naming them, I’m gonna forget one but, you know, I think that, in a way, it’s an exciting time in music, that it’s democratized in such a way on many levels. There are still levels that it’s not democratized but, you know, where if you are dope, someone’s gonna hear it and that wasn’t the case a long time ago and so I’m all for that and I just wanna be a part of great music. I’m personally getting back into writing and producing music, which I haven’t done in like 15 years and it’s something that the pandemic allowed me some time to do and so I’m excited to get back in as a producer and start getting some of my own tracks out there as well and just being creative and just not taking it too seriously, you know?

I take my responsibilities seriously but we also have to treat it with a bit of levity, you know, in order to continue to push through it and deal with some of the headaches that come with being in the music industry. And so — I don’t know if that answered your question but that’s what I had to say.

Dan: Well said. Well, Benjy, this has been a pleasure. Thank you. This is great.

Benjy: Thanks for having me on.

Dan Runcie

Dan Runcie

Founder of Trapital

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