How Roc Nation’s Lenny S Went From Selling Records on the Street to Working With Jay Z

February 28, 2017, 3:06 PM UTC

As a music industry executive, Lenny Santiago, better known as “Lenny S,” is rarely in the spotlight—that’s the domain of his artists. Yet as a senior vice president at Roc Nation, the New York entertainment company founded by rapper Jay Z, Santiago regularly collaborates with some of the brightest stars in the music industry.

It wasn’t always that way. Growing up in the Bronx, Santiago remembers listening to Run-D.M.C. on the radio. At 11 years old, he was captivated by the hip hop group’s music, fashion, and lifestyle. The group was founded only a few miles to his south, in Queens. But after the group achieved fame, they might as well have been lightyears away.

“It was all about music—how can I get in music industry, how can I meet music people, how can I go to music seminars?” Santiago reflects. “I was pursuing it and chasing it.”

He chased the dream of landing a job in the music industry until he was hired as a street promotions rep—that’s a fancy way to say that Santiago was handing out cassette tapes, distributing flyers, and hanging up posters. “I was doing whatever I could to promote the artists I was working with,” he says.

One of those artists happened to be an up-and-coming artist named Jay Z. (Yes, that Jay Z.) Santiago has worked with the Grammy Award-winning artist for more than 20 years at both of the rapper’s record labels—Roc-A-Fella Records and Roc Nation. It’s safe to say that his days in street promotions are long gone. As a Roc Nation exec, Santiago gets to sign artists like DJ Khaled, Vic Mensa, and Justine Skye.

On Feb. 23, Santiago was honored for his business achievements at a New York City event hosted by entertainment events company Fueled By Culture. In a conversation with Fortune, he reflects on his time in the music industry, his relationship with Jay Z, and his thoughts on independent artists.

This Q&A has been edited for clarity.

Fortune: How did you go from doing street promotions to making records?

Santiago: I was sort of hitting my head on the ceiling when it came to street promotion. My bosses at the time were Damon Dash and Jay Z. They asked me one day: “What do you want to do? You seem like you’re kind of bored with this.” And I was like, “I actually want to make records. I want to get in the studio with artists.” The next day I was in the studio with Jay Z, Memphis Bleek, and a producer by the name of Mahogany, and we made the record “It’s Alright.” And from there, I was making records, and I never turned back.

You’ve known Jay Z for more than 20 years. What was he like early on in his career and how has he evolved into the business person he is today?

Early on, I was just a fan—a fan of the music and a fan of the business mind. One time, there was a car show in New York at the Jacob Javits Center. At the time, Jay Z was just starting out. He had a single called “In My Lifetime,” and [he and his team] was in front of the Javits Center giving out the singles with little Moët bottles. And I had never seen anything like that. I thought it was genius from a marketing perspective. The people who didn’t know them were just intrigued to know: Who are these guys, and why are they giving out Moët bottles as if they’re bottles of water?

I just had a gut feeling that he was one of the best. I felt that in my heart. I wanted to be a part of a team that I thought was going to make a real mark on this industry, and I was pretty right.

It was announced that Jay Z is launching a venture capital fund. What do you think about Jay Z as an investor and his ability to identify these up-and-coming companies?

I think he’s just really smart. He’s a businessman. I’ve been able to be there with him when he’s had these thoughts. What you guys have seen come to fruition, I saw its inception 10 years ago when he was brainstorming it. Those are the things I value, and I sometimes feel like I’m the luckiest guy in the business to have a friend, a mentor, a brother, and a boss like that. From the beginning, I remember thinking, “This guy knows what he’s doing, he knows what he wants.” He’s assertive, firm, and innovative, and I just wanted to be a part of that.

In interviews, you’ve said that you tell artists that people either want to believe in them or want to be them. What do you mean by that?

As an artist, people have to believe your story. When they believe your story, it allows them to believe in you. If they feel it’s fake, they are not really going to believe in your music. You want fans to care about your lifestyle, what you’re eating, where you’re hanging out, what restaurants you’re going to. That’s what makes people buy into you and your brand.

The strategy for artists to remain independent seems to have become popular lately, e.g. Chance the Rapper. He has no record label, no distribution deal, nothing. Do you believe it makes business sense for artists to go that route?

I would encourage any artist to do so if they could. I don’t think it’s for everybody, but I certainly think you should try. Literally with a computer, you can send your music to the world. You can build an entire fan base and send out a flyer to where you’re going to perform. You can tour and sell merchandise and records without a record label.

I think there are some artists that need the 100 employees that come with a record label. Some artists need the different departments of promotion, publicity, and branding to amplify what they’re doing. The reality is, Chance is amazing—but unfortunately, not everybody’s going to be Chance.