Exclusive: Roc Nation's Lenny S. Reveals Classic Jay Z Stories & Keys to Success

Lenny Santiago, Senior Vice President of Roc Nation, is at the top of the music game now, but he wasn’t always on that throne.

In the ’90s, the man known as Lenny S. or Kodak Lens, started his career doing promo. Eventually, he worked his way up Roc-A-Fella Records’ street team and his grind earned him a shot as an A&R. By staying consistent, his career only flourished further. By now, he’s managed to work on some of rap’s most celebrated albums, including Jay Z’s The Blueprint and Hov and Kanye West’s joint project, Watch the Throne.

Today, Santiago is looking out for kids with dreams like the young Lenny, creatives who are willing to work hard. He partnered with Brisk for their #BriskMode campaign in honor of Hispanic Heritage Month. Through this, creatives over 18 can submit designs inspired by their heritage for a chance to fly to ComplexCon next month.

Young hustlers can learn a lot from Lenny. Rap-Up recently sat down with Santiago to talk about his career. He shared insightful stories from his rise, his unique perspective on classic albums, and a major key to success.

What motivated you to get involved with the #BriskMode Accelerator Program in honor of Hispanic Heritage Month?

My motivation was honestly to motivate others. I am Hispanic and I feel that’s not showcased enough. I work in an industry where there are less Hispanics, obviously, than other races. I think that needs to be highlighted, that we’re important to the culture, to the community, and to what’s going on, that we care about the culture, what’s going on in the arts as far as music, fashion, and everything else involved. I just wanted to be an example, show them what being in #BriskMode is about, grinding, how hard work pays off. I’ve made a career out of this.

You’ve had a great career, but your early days were in the Roc-A-Fella street team. What were those days like?

I got an early start at Roc-A-Fella Records being part of the street team. In my career in general, I started on the promotion side of things. I thought promo was the best way into the business. Coming from where I come from, I was uneducated, I was just trying to make my way into the entertainment business. I thought being on the promotional team would garner me more access than an internship would because I got to explore the office side of things as well as the street side of things, the events, the parties. I was on tours early on in my career being one of the top street team guys. I would go on the road and promote what we were putting out at the time. It was difficult getting in the door, but once I was in and once I proved that I was an asset to the company, and that I could really do my thing promoting these artists, that [allowed me] to travel on the road, go out to seminars and conventions around the country in the ’90s. I grinded, stayed focused on my goal, and then I reached it by going on the inside. I took off from there.

From there, you’ve been able to work on some of rap’s biggest albums. Let’s go back to The Blueprint, which celebrated its 15th anniversary on 9/11. What do you remember about those sessions and that release?

The most memorable thing about that, besides it being one of my favorite albums, was how it got started off…Being a part of it and being there for that weekend, whatever few days that Jay did those eight records. I forget if it was eight or nine. It was all the Kanye West and Just Blaze tracks at the time. He breezed through a majority of the album. When Jay gets in a zone, it’s just incredible. To actually witness that and be in the studio, to watch him record these records, and be so inspired. Those tracks were so incredible. He was in a great zone and knocked it out. You just saw, this was the beginning of something great. To knock out something of that magnitude, what those songs have meant to the culture, to the album that that was, it was an amazing thing. That is my biggest and best memory from that. It takes, sometimes, a year or two for people to pull of an album like that. He had it done so quickly.

Is that your favorite Hov album?

I have three or four. There’s Reasonable Doubt, Blueprint, The Black Album, and I’ve gotta say Watch the Throne. It’s with Kanye, but that’s a shared Jay Z album. Those are my favorite-favorite-favorites.

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You were there for Watch the Throne too. How was that process different from Jay and ‘Ye’s solo work?

I can’t speak on the ‘Ye side, but on the Jay side…They had a great synergy together. They were already family so it wasn’t difficult. I think something like that becomes more of a challenge if the people doing an album together aren’t really good friends or aren’t fam. You gotta take that into consideration when putting an album together, what that synergy is going to be like. For them, they had already done multiple records together, were on the same label, they shared admiration and respect for each other, so to get in the same room together was like, “Bam! This is gonna obviously be incredible.” I think the only question was how incredible it was going to be. It had the potential of being exactly what it came out to be. To be able to witness that was pretty amazing. It came out nothing less than what I thought it would, which was iconic and classic.

You saw Jay in the early days. How is he the same and how is he different now than when you first started working with him?

There’s no real difference. He’s always had the same way of working. He gets in his zone. He gets in the studio, listens to tracks, and gives it his all. I don’t think there’s no specific or particular process changing from what The Blueprint was or Vol. 3 or Blueprint 2.

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What’s the biggest life lesson or as DJ Khaled would say, key, that you’ve received on this journey?

The key literally is that relationships are key. Relationships have got me through a lot of sticky situations. Relationships have got me through executing what I need to do, turning nos into yeses, turning $100,000 fees into $50,000 fees, to doing something for free for me. It’s those relationships. That’s not what it’s for. I’m not keeping a relationship to get favors at all. It’s just, people know that I genuinely will do anything for them. I think that that’s received well by everybody I work with in the industry, personal or professional, it comes back to me. It’s reciprocated. People treat me well and artists will do things for me…We did a show the other day with Khaled opening the “Formation Tour” [for Beyoncé] in Atlanta. I always get the artists together and I’m the one that gets them there and invites them out. Some of the artists just was like, “Yo, man. It was you so I had to come.” They had other plans. They were supposed to go out of town. It makes you feel great when they’re like, “This is for you,” or, “This is for you and Khaled.” For some of these things, they’re not getting paid. They’re just coming for the love and the culture. You gotta respect that these artists get paid a lot of money to do these things, to do features, guest appearances, to come on stage. But again, like with anything else, the relationships are what gets it. It’s just not about the money, stature, none of that. Some people still don’t know what I do. They just respect me ’cause I respect them. It’s a genuineness there. That’s what I live by and that’s what’s gotten me through this.

What are you currently working on that you’re really excited about?

Be excited about Fabolous and Jadakiss and what they’ve been talking about for months, this Freddy Vs. Jason thing. Be excited about Justine Skye coming. Be excited about more Khaled stuff coming. He’s about to release a book and is focused on film and television next year. Be excited about, shit, maybe Jay will get the bug to do music again. Who knows? Obviously, nothing confirmed, but some of the verses he’s put out — he did the Pusha T thing [‘Drug Dealers Anonymous’], he did the Fat Joe thing [‘All the Way Up’], he did the Khaled thing [‘I Got the Keys] — it’s exciting. Be excited about Vic Mensa. Vic Mensa’s serious, man. He’s taking time with this album. He’s like 80 percent-90 percent done. We’re about to come soon…It’s gonna be great…There’s a couple things coming down the pipeline that I’m real excited about.

–Andres Tardio