LennyS Art of Being a Legend in Style Bonobos Lookbook RocNation Complex Photographer Fashion Mogul Business Finance Tips Successful Lenny Roc JayZ
LennyS Typical Day Timeline DayinTheLife Schedule Bonobos Complex RocNation Lookbook Roc JayZ Lenny Photographer
LennyS Typical Day Timeline DayinTheLife Schedule Bonobos Complex RocNation Lookbook Roc JayZ Lenny Photographer
LennyS Typical Day Timeline DayinTheLife Schedule Bonobos Complex RocNation Lookbook Roc JayZ Lenny Photographer

THE ART OF BEING A LEGEND (IN STYLE)

Roc Nation’s SVP Lenny S. Tells Us Why We Need to Sit Down and Be Humble.

You are the average of the people you’re closest to. Jay-Z has recently been in the spotlight as hip hop’s first billionaire. Hov's fortune spans across several categories—his art collection, real estate, liquor, the streaming platform TIDAL, and most notably, his entertainment company Roc Nation. In the widely popular Forbes article that named Carter a billionaire, Roc Nation was valued at $75 million. How did Roc Nation become a music empire? Lenny Santiago, better known as Lenny S., is one of the forces behind the company as its SVP and part of Jay-Z's inner circle. He believed Jay would rise to the top; he left Bad Boy Records at its peak in 1995 when Notorious B.I.G. was gaining momentum, and begged to join Jay-Z's newly established Roc-A-Fella Records. The label initially denied his request, dubbing him a “Bad Boy.” After some persistence, Lenny was finally accepted. Having been at Jay’s side for the last 20 years, the Bronx native helped build the Roc Nation empire. Today, Lenny S. manages a roster of artists including DJ Khaled, Justine Skye, and Vic Mensa.

Aside from being a music executive, Lenny S. is a talented photographer holding some of the rarest shots of Jay-Z and Beyoncé, as well as the late Nipsey Hussle. He's also a style savant in his own right—he was the creative director behind our latest editorials with Ajay Relan and Mack Wilds showcasing how Bonobos’ Chinos can work for every occasion. A quiet, yet powerful force, Lenny S. sat down with us to discuss his success as a music mogul, and how he manages to remain a legend in hip-hop culture, while staying stylish in Bonobos.

LennyS Bonobos Lookbook Gallery Complex RocNation Photoshoot Photographer
LennyS Bonobos Lookbook Gallery Complex RocNation Photoshoot Photographer
LennyS Bonobos Lookbook Gallery Complex RocNation Photoshoot Photographer
LennyS Bonobos Lookbook Gallery Complex RocNation Photoshoot Photographer

TIP 1

Be humble.

When asked how he became such an integral part of culture, Lenny S. says, “There was nothing I wouldn't do, right? It doesn't matter if it was my job description or not, job duty or not. If somebody needed McDonald's, I'm going to get it. If somebody needed their pants ironed, I'm going to iron them. If somebody needed to close this deal, I'm going to close the deal.”

Lenny’s biggest gripe with today’s generation is the lack of humility, a recurring statement by older generations who paved the path for creative expression.

Lenny S. goes on to say, “A lot of the kids that I've dealt with, and interns and assistants and so forth. They're kind of like too cool. You know what I mean? And it's like everybody doesn't want to do everything, and they're too cool to do certain things, or it's not in their job description. They feel like they're being played if they're doing something that's uncool or corny. I've maintained who I am as a worker, as a manager, as whatever. It’s like, it doesn't matter. I'm going to do anything it takes to get the job done.”

That same humility in Lenny’s work ethic can be seen in his style. Although Lenny is occasionally caught in fresh Bape gear, and always donning a Roc Nation snapback, Bonobos easily translates into his wardrobe. Here, Lenny chooses the Bonobos Denim Shirt in Navy Tencel paired with the Bonobos Stretch Organic Cotton in Blue while on set shooting his good friend, Ajay Relan, founder of Hilltop Coffee and #HashTagLunchBag.

As a creative, photographer and music executive, staying comfortable and polished is a priority. The egoless Bonobos Chinos affords Lenny the versatility required for his demanding career. He shows us that you don't always need egregiously priced brands to prove your success.

LennyS Bonobos Lookbook Complex RocNation Photographer Gallery
LennyS Bonobos Lookbook Complex RocNation Photographer Gallery
LennyS Bonobos Lookbook Complex RocNation Photographer Gallery
LennyS Bonobos Lookbook Complex RocNation Photographer Gallery

TIP 2

Brand yourself.

One of Jay-Z’s most recognized lyrics is his statement on Kanye West’s “Diamonds (Remix)”: I’m not a businessman / I’m a business, man."

Channeling this energy, Lenny made himself into a brand. He tells us, "I created this character or personality called Lenny S. Prior to that, I was Lenny Santiago. I worked at Roc-A-Fella Records and I was a good employee, but I created this brand, so to speak, that can be trusted. Can be called upon if needed. Can host the party. Can make a mixtape. Can shoot a campaign. I made sure that I'm going to be okay in this business no matter what. Doesn't matter what company I'm working for, what artist I'm working with, I will always be able to go elsewhere if need be."

He recalls an early incident at work which motivated him to explore other passions: "A long time ago I worked with Damon Dash, who was the CEO of Roc-A-Fella Records at the time, great guy, taught us a lot. He had threatened us. Somebody had did something very, very bad, and got fired or was about to get fired, and he was like, 'Everybody better get their shit together because this could be you tomorrow and if this happens to you what are you going to do? Who knows you? Who knows your name outside of this company? Could you get another job in this business?' He just really gave it to us, and it kind of scared the shit out of us."

Years later, Dash's pep talk is still with Lenny. He's been more open about opportunities, hinting at a book deal, and now more assertive about taking credit for his photography work; recognizing he's paid his dues. Cleverly named @kodaklens on Instagram, Lenny has taken amazing photos of his beloved friend Nipsey Hussle and others. Here, he dons the Bonobos Short Sleeve Popover Blue Calle Stripe and Bonobos Premium Stretch Washed Chinos in Jet Blacks.

With over 60 Guideshops across the country to help you shop online, Bonobos carries some of the most functional and fashion-approved options for your wardrobe. Grab a pair of Chinos today, and be sure to catch more of Lenny S.'s photography work in Part I and Part II of this series.

CREDITS

  • WRITER  Hunter Mak
  • DESIGNER Mike Hernandez
  • PHOTOGRAPHER  Bukunmi Grace
  • STYLIST  Khalid Briggs
  • PRODUCER  Daria McCall
  • WEB DEVELOPER  Michael Karaim