Deskside: Lenny S.

Senior Vice President of A&R, Roc Nation

Deskside: Lenny S.

Beyonce. Jay Z. Big Sean . Rihanna. Kanye. #squadgoals.

But alas, 'tis the IRL posse of the uber charismatic Roc Nation exec, Lenny S., with whom we scored some very, very valuable face time in his New York office. If you haven’t noticed by the pictures, we wouldn’t call this space your traditional grey-cubicle work area—it was decked out in gold everything , down to THAT tufted couch, and sprinkled with one-of-a-kind music industry memorabilia, about which we couldn't resist getting every single backstory. Not that we would have expected anything less from a guy whose personality alone, okay, and likely his dedication, too, had him climbing the ranks from street promotion to sitting side-by-side with Shawn Carter on the daily. NBD.


“At a very young age, probably 10 or 11, I heard Run-D.M.C on the radio. At the time I didn’t know it was rapping, but I knew I want to do it. Whether it was working with them or rapping. Time passed, I learned about music and culture. As a teenager, I was trying to figure out how I could get into the hip-hop business. I started doing promotion with a friend of mine. It was street promotion, which was the best way to get into the office. I could be on the road and in the street on tours with artists and promote their stuff. I went to a bunch of companies and asked them to give me product for free and I would promote their product for free. They gave me CDs, cassettes, flyers, stickers or posters, whatever they had at the time. That got me notoriety in the music business. The manager, artists, everybody, would see me at every event and see my face handing out products from all these different artists. I ended up getting a job with Bad Boy, which I then left the day I heard that Jay Z was starting his own company called Roc-A-Fella Records. I was like ‘I’m going to be the illest and best street promoter for this label'. I begged for a job there, I got a shot at an internship and never turned back."


“By the time the second album came out [at Roc-A-Fella], which was in 1997, I had been doing promotion for them for two years and I was hitting my head on the ceiling. Damon Dash and Jay Z were like ‘what do you want to do? You’ve done all you can do [in promotions]’. I was like, ‘I want to be in A&R. I want to work on music; I want to discover artists’. I didn’t think they’d give me a shot because I had no experience. And to be in A&R, you pretty much have had to discover an artist, producer, or rapper—somebody that shows that you have an ear for talent. They gave me a real shot. They were like, ‘Look we’ve known you for knowing great music, we’ll give you a shot’. They said ‘Alright, tomorrow you’ll become an A&R. We’re working on a project called “Streets is Watching”. It was a soundtrack to a bunch of videos Jay had done for a little movie we were putting out. The next day I was in the studio with Jay Z and we were working on a song titled “It’s Alright”, which ended up becoming the single for that project.”

"I work with them, I work with people that shift the culture, and I want them to feel confident standing next to me."


“[There were] a lot of struggles [in the beginning]. It was getting people to believe in what you believe in and being able to get people to sign. Obviously, you know, as an A&R you discover talent—I’m really selective in the talent that I bring. But everybody might not see [the talent] in the same light that you do. Jay always jokes that I can be too early on things at times. I’ll bring something in at a time when there are 6 or 16 people on it. Our job is to find it, discover it, when very few people are on it and get on it early—what it’s going to be in two years or ten years. That’s one of the main struggles: it’s bringing talent to the table that I believe is going to be really good or really successful and maybe they’re not seeing the vision, per se. And that’s at any company, not at just Roc-A-Fella, but any record company.”


“My ear, my instinct, and my relationships. My ear is where it starts. It allows me to hear the music, hear the artist, hear the voice, see the potential, and hear the potential. The instinct is, am I going to believe my gut and run with it? Am I going to go and bust down Jay Z’s door and say ‘Jay, this is the girl or this is the guy or this is the person, and this is what needs to be signed with us’ that’s the instinct. The relationship is being able to execute, and in this business, I’ve been able to execute almost everything based truly on my relationships. I mean, yeah, the money’s cool, and the budgets, and signing people, and you can offer them the perks. All that stuff is cool, but it’s my relationships that have gotten me everything. By everything, I mean, this producer charges $100,000 for a track but I have an 8 or 15-year relationship with them, and now they do it for $40,000. This artist wants to sign with me, but I only have $500,000 and Sony RCA have $1M. You know what, they respect me more and my relationship with them means more to them than the money, so they’re going to sign with us. The relationship 98% of the time gets me what I want and what I need. Guys who say no to things, who say no to working together, I bridge that gap.”


“It’s 24 hours. I mean that—I’m not joking. I sleep like 3 or 4 hours a day. It’s not good for you but the reason for that is because it’s the way I’ve gotten my relationships. You’re going to get what you give, right? It’s legit real. I get what I give. The other day I flew from Paris, landed in New York, dropped my bags, ran directly to the office, had meetings for a big Samsung event with all our artists performing. From there, ran to a Justine Skye album release party (she’s on Atlantic Records and I love her music, even though I have nothing to do with her). I’ve known her for years and I’m a fan. I went by her event, showed her love and made sure I didn’t miss that—that’s what relationships are about. I went from there to J.Cole’s performance, because that’s our artist. From there I went to a club got up with the DJ, made sure our records are being played—you know, shake the hands of everybody—went home, packed for LA, and flew to LA and did all that stuff over again in our LA office. It was just 24 hours and I probably slept for only 2 hours on the plane. There are obviously meetings, studio sessions, concerts, and red carpets. I’m a big advocate about being in the street and being out there. The office is good, it’s cool, it’s someplace you could be settled for a while and handle emails, but I need to be mobile, I need to be active, I need to be in the artists’ faces. They need to see you and they need to feel your support.”


“Since the Internet hit the universe and records aren’t sold as they used to be. Record sales are mediocre, [and now] everything else is coming from the lifestyle aspect, from touring and your income is coming from the branding. Brands have finally realized that they want to be associated with what’s cool. And what’s cool? The culture’s cool. And what dictates and moves the culture? The music business and the people in the music business. Whether they’re influencers or artists, those are the ones dictating what clothing to wear, what car to drive, and what music to listen to. Brands really need to understand that we need to be involved in the entertainment business and partnering up with them. They need to make sure that their dollar is being well-used and now they’re using their budgets towards partnering up. Jay—which is the reason why I will follow this man anywhere in the world— saw this a decade ago; that it’s all about the brand, it’s all about us partnering up with brands and really using each other to help get what we need out there to the masses. We’ll be able to dictate what people are doing, listening to, wearing, attending, or whatever it is.”


“It’s been my thing from day one—I always wanted to stand out. And what’s standing out? I mean, obviously not being so flamboyant and loud that it’s obnoxious, that’s not what I want to do. I want to be liked, to show that I’m a great guy and I have great relationships, I just want to be received well but I also want to stand out. I understand that if Footlocker is selling sneakers , and they have 3,000 pairs and there are 6,000 people coming to buy them, that there are 2,999 other guys that have the same sneakers I have, so, what do I have to do? I have to find the pair that wasn’t sent to Footlocker, I have to find a pair where there were only 300 made. I’ve always been that person. It’s not about wanting to be better than anybody else, it’s about wanting to stand out. I want to be an individual. If I’m gonna wear a tie—you know what? 90 out of 100 guys here are going to have ties on. I think I’m gonna go with an ascot. I think it looks great, it’s sexy, and I’m least likely to find anybody else wearing it. I wear flamboyant brooches that have floral arrangements and five colors in them. I’m gonna get a couple jokes here and there, like ‘oh my god, what are you wearing?’ but you know what? 99% of the women and 50% of the men who are confident and understand what it is are like wow. I go to a flea market and get a pin with a flower as opposed to just a floral shop and getting a rose to put on my tux jacket—I just want to take it to the next step. I want to do things that make me stand out. I think that we’re all a representation of who we are and who we work with and who you represent. I represent some of the biggest artists in the world. I work with them, I work with people that shift the culture, and I want them to feel confident standing next to me. I want them to feel confident with who’s representing them. I work with the biggest mogul in the world, Shawn Carter.”


“I bought it from a place that wouldn’t sell—you can only rent the furniture for a cool event or for television. I begged them for months and they wouldn’t sell it [to me]. I was offering them double and triple the money. It’s funny because when I put the couch and the chairs in my office a couple people were like, 'oh my god that’s fucking hideous'. When I finished, little by little, they were all like okay, this is not bad. I’m not bullshitting you, it’s one of the most popular offices within the company and on social media.  I meet people on the street in LA and Chicago and they’re like ‘you’re the one with the gold office!’ It’s like, all over social media, it’s kind of crazy. When I started making that office, we have glass walls, so everyone can see inside, so I put wallpaper so you couldn’t see inside. I left that up for three weeks until I had every piece. As you can see in the photos, every piece is unique, some are antiques, and all of them are from different stores. I know my own vision, and I know when it’s done it’s going to speak in volumes.”


“When we did the Magna Carta album (the Jay Z album that Timbaland produced), he at the time, was working on the 20/20 album with Justin Timberlake in the studio in NYC. Jay had one suite and Justin had one, and Timbaland, who was orchestrating both albums, was working in between both. Justin would come over to our sessions and we’d go over to his. He ended up being on three records on the album, helping us with vocals and background vocals and production. We ended up developing a great relationship with him, we did the tour [with Justin and Jay]. I promise you, [Justin is] probably one of the nicest, most genuine guys in the music industry. The type of guy that knows your aunt’s name after seeing her once seven months ago. He’s that guy. So obviously I’m a sneakerhead and since I do A&R, I’m in charge of Jay’s album and I had to make sure Justin was good throughout it all. He made these exclusive Jordans, 1s, 2s and 3s for the tour we did, so they were only made in a limited amount of pairs. They were sent directly to him while he was on tour. I was in Jay’s dressing room one day and they’re like ‘Hey, Justin’s at the door’, and I was like ‘Okay, I’ll go tell Jay’. They said ‘no, no, he’s here to see you’. Of course, I go over and open the door and he has all three sneakers in his hand. He’s like, ‘you’re a sneakerhead, you always have fresh kicks on and limited edition kicks and here’s some that we made for the tour’.  They were all red Jordan 1’s, Jordan 2’s, and Jordan 3’s, and they were made specifically for the tour. On the insole it says Legends of the Summer—they were just for Justin and Jay but he hand delivered me a pair of each in my size t. It’s a testament to what kind of guy he is. He could have sent his manager or assistant over but that’s the kind of guy he is.”

"It’s funny because when I put the couch and the chairs in my office, a couple people were like, 'oh my god, that’s fucking hideous'."


“It’s so much, I won’t lie to you. Some of my friends call me a hoarder. I try to keep everything related to the music industry because it’s so limited. Items are just made for that album, that time, you know, so I’ll take the Murakami artwork that was done for Kanye’s album and then I’ll have a special print printed of it and have Kanye sign it. So all of those items, promo items, merch, Trapstar, which is a great brand out of the UK did all of the merch for Rihanna's last tour. So again all of those pieces is like you’re never going to find them again. They’re very limited pieces.


“Know what you want to do, be sure about that. I meet a lot of people who either want to be an artist or an executive but are unsure—they just don’t know exactly what it’s all about. Have some sort of direction to where you want to go. Whether you want to be a producer, an artist, a record executive, and then just be as consistent as you can. Consistent and persistent. Persistent without being annoying and pestering people. Do your homework, find out the things you need to find out and the people you need to meet and be out there in every aspect you can. Whether it’s events or concerts, making contacts and developing relationships, and starting off working for free if you have to—proving that you can work hard. But the consistency is everything and knowing what you want to do and having a goal and executing that goal.”


“Keeping relationships, returning every call and email that I can. And all of those things sound like basic crusades, but it’s great advice because this is a personal industry where you’re dealing with people on the regular. And no, you won’t be able to keep everybody happy, but people will be able to say he’s reliable, he’s responsive, everytime I get referred by somebody because they want to work with my artist or work with me, they say this guy is good, he’s responsible, reliable, responsive. And you’d think that’s all regular stuff but it’s really not, so many people aren’t, so many people avoid you, so many people avoid your call, email, meeting, they only deal with the people they think they should, so again being consistent and developing and keeping those relationships and doing the best job you can do and being personal with the artists that I work with and them being able to rely on me. I’ve watched all those guys work a room and work a room and be charismatic. They keep their word. That’s another big thing. Keep your word."

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