9-5, 5-9: Lenny S.
Words: Lakin Starling
Images: Joshua Kissi
Images: Joshua Kissi
For those who love the grind, there’s no such thing as a day job or night shift. From 9-5 to 5-9, they’re always on. Music exec Lenny S. works with some of biggest acts in the game, and as a photographer, he captures some of their most iconic moments.
It’s fairly still at the Roc Nation office in Manhattan on a Wednesday afternoon. Perhaps it's a case of mid-week mundanity or maybe this is the normal vibe of one of the biggest record labels in the industry. The ebullient voice of Lenny S. breaks up the quietness. Through the glass opening of the room I’m waiting in, I spot the Senior Vice President’s spotless pair of tan construction boots as they’re headed in my direction. He greets me with a hearty welcome at the doorway and leads me past a few packed offices before we get to his spacious corporate palace. “Sit wherever you want,” Lenny extends. I hesitate but he swiftly sits on the long window sill so I plonk down on his legendary gold couch.
Lenny Santiago was born in the Bronx, NY and his vibrant genuineness was shaped by his morally rich upbringing. He was raised by his single mother, but when she worked as a bartender on weekends, he stayed at his grandmother’s. Both women equipped him with strong values that still beam through his benevolent demeanor. His father was present but he lived in Puerto Rico for the earlier part of Lenny’s life. Every summer, he would leave his cherished borough and go to cities like San Juan, Bayamòn and Ponce to be with his dad before he moved to New York when Lenny was 11 years old. While he may have spent some time away from his hometown, the Bronx’s rich culture made an indelible impression on him. “I grew up in the city that invented Hip-Hop,” Lenny boastfully dotes as he’s cooly posted in his casual all-black fit. “And it runs through my f*cking blood.”
He found his rushing pulse for music the first time he saw Run DMC kicking their krush grooves on television. Throughout his adolescence he had a few more experiences that cemented his love for Hip-Hop: When he was 12, a Def Jam A&R for Slick Rick brought the mega MC to the neighborhood in a luxury whip. Lenny specifically remembers their flashy gold chains and leather Def Jam jackets. The following year, DJ Kid Capri spun records at the Kingsbridge Boys & Girls Club where Lenny’s mother worked. Capri’s manager would let Lenny stay at the infamous teenage parties that he wasn’t old enough get into. “I would sit in and watch 18 year olds with their flat tops, jewelry and fly sneakers doing all these dope dances and think holy sh*t.”
The evolution of those definitive cultural moments also inspired Lenny to pick up photography as a hobby once he entered high school. “We were in 10th grade and girls were wearing these high end clothes. The Latina girls always had fresh hair and makeup. Whatever the changes were, I was obsessed with capturing them,” he remembers.
He’d developed a promising hobby, but his main focus was always on Hip-Hop. From freshman to senior year, while his peers were involved in academic clubs and sports, Lenny was hell-bent on chasing his music career. If there was an in-store album signing, he was there fearless and willing to be seen. “I just wanted to create some sort of familiarity or consistency of, I don't know who this guy is, but he's everywhere,” he recalls. Instead of being starstruck and insistent on solely meeting the artists, Lenny understood the importance of connecting with adjacent figures like managers, best friends, or even music journalists to potentially secure an enlightening opportunity. When Lenny graduated high school in 1992, he applied to colleges but with no financial aid he shrugged off his parent’s sanitation worker recommendations and buckled down on his music dreams. He got his first taste of the industry when he went on tour as a roadie with a few New York-based rappers who were hot at the time.
In 1994, Lenny teamed up with his best friend Burt Bazin to run off stickers, flyers, and postcards of popular neighborhood rap duo, Black Sheep. Lenny and Burt went all around New York City posting logos wherever they could. It was an unpaid gig, done purely out of sheer support for their pal but the move essentially kicked off Lenny's career in music. After Black Sheep’s record label got word about their independent marketing scheme, the guys started getting an influx work. In 1995, Lenny quit his 9-5 job when he got an offer to work on the street promotion team at Bad Boy Records. At the end of the year he went to pick up his holiday bonus only to find that his manager had quit. Lenny’s co-worker told him, “He left. He went to work at some company called Roc-A-Fella Records.”
"I just wanted to create some sort of familiarity or consistency of, I don't know who this guy is, but he's everywhere."
Having heard about the rising enterprise, he rushed to meet his former manager and pleaded for a meeting with rising star Jay-Z. Lenny was willing to work for free but Jay-Z wasn’t eager to put him on, “As soon as I walk in, Jay sh*ts on me,” he laughs. Jay-Z recognized Lenny from his previous work but quickly wrote him off, “Nah, he’s a Bad Boy.’”
Lenny had walked out on the opportunity to continue working with Bad Boy at the height of the Notorious B.I.G.'s career on faith and now he found himself unemployed. But in 1996, he managed to get the product for Jay-Z’s album campaign. He started taking the bus to whatever city Jay-Z was performing to do solo street publicity. He learned to channel the need to create a life for himself beyond the bleak options of his neighborhood into a relentless grind. “On my block, there were drug dealers and they would get locked up,” Lenny says. “I was watching all those things and saying, I can't do any of these things. I can't be a product of my environment.” After a while, Roc-A-Fella couldn’t ignore Lenny’s hustle and brought him onto the team.
His first year at Roc-A-Fella passed by quickly and with years of experience in the field, Lenny felt it was time go deeper with his love for music. With the green light from Jay-Z and label CEO Damon Dash, he helped an in-house producer with some logistical work and was promoted to an A&R position for his efforts. His first project was working on the soundtrack for “Streets Is Watching”, a music video anthology that explored some of the harder joints from Jay-Z's "In My Lifetime, Vol. 1" album. A project that didn’t quite have the impact they wanted but the film became an instant hood classic. The success of the film and soundtrack propelled Lenny up through the hierarchy of the label. Although he admits that there wasn’t a big emphasis on titles at the label. What was really important at Roc-A-Fella was relationships. It was his close friendship with Jay-Z that helped solidify his position. Their friendship was cultivated during and after his 16-hour studio sessions. “Jay had an SUV,” he recalls about the memorable 4 a.m. rides home. “He [Jay-Z] lived in Jersey so we would leave lower Manhattan, he'd drop off Hip-Hop and his assistant in Harlem, and then me in the Bronx.”
Witnessing Jay-Z become the biggest thing in Hip Hop was monumental, but with his lifelong inclination to chronicle life, Lenny knew that there were priceless moments that needed to be captured. “This was before artists traveled with videographers or content people,” he tells me. He was baffled by this lack of documentation but with the trust of the crew and his own reassuring energy, Lenny was able to create comfort in spaces where outside photographers weren’t embraced. Soon he was always around to gather snapshots of artists at some of their most public and private times, much of what he shares on his eventful Instagram profile: @KodakLens. “I have all of these intimate moments because I never exploited anybody,” Lenny says. He humbly claims that he’s “not a great photographer” but says that his access to his subject’s vulnerability is what makes his images special.
Lenny’s favorite and first viral picture is the largest and in the center: It’s a final image from the “Run This Town” video shoot where no photographers were allowed. Lenny transports back to the impromptu moment, “At the end of the shoot, I saw this alley and was like, ‘Wait! Let me catch this real quick.’ Jay [Jay-Z] was like, ‘Come on man.’ Then they all really struck a pose. I got these three mega stars,” he admires. “You see how tall they’re standing?”