Lenny S on the Importance of Charity, Giving Back and Being Inspired By DJ Khaled

Roc Nation's Lenny S. sheds light on his various forms of charity work.

Lenny Santiago
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Lenny Santiago

If you're even just halfway in or around the music industry then you know of Lenny S[antiago]. The Roc Nation SVP has been a fixture in the game for basically as long as Jay Z's been around. Nowadays you measure an event's relevance by his appearance—and measure a person's relevance on whether they were able to get a snapshot on his highly coveted gold couch. In between high-profile appearances and artist management though, the vet carves out plenty of time for charity and giving back, beyond the philanthropy that Roc Nation already participates in.

Complex talked with Lenny to shine a light on the charity work, particularly his affiliation with 123Wish, an experience-based campaign that partners with celebrities and influencers and is specifically youth-targeted. The chosen experience varies per the partnership—for Lenny, the winner gets a meet-and-greet as well as a photo on The Couch. In speaking with 123WISH CEO and co-founder Natalia Diaz, she says "The idea came about when I noticed that most of the current campaigns and auctions weren’t necessarily targeting the younger demographic—or being made affordable for the mass market. We wanted to be the facilitator in helping make their dreams come true, whether that be working as an intern with your favorite celeb, being an extra on a movie set, or even going back stage as a VIP guest.” Diaz keeps abreast of pop culture to continue tailoring experiences that the youth actually want versus something basic. Like, Lenny's "prestigious couch."

Talk about how you became affiliated with 123 Wish?
It came through a good friend, Hillary, who I have known in and outside of the business for almost two decades. I honestly only like to involve myself with people I know, people I trust, organizations I feel strongly about and what they’re doing and who they are targeting. And you know, who they are targeting is one of my biggest interests. Even planning to be able to take those funds that are made and put toward a charity of my choice and my liking. That is what really attracted me: they're targeting a really young generation. They made it a very affordable way to bid 5 dollars or you could get something for 15 dollars or even 150 dollars or a thousand but whatever at least everyone has an equal fair shot. It is not something that is just for people who are super successful or financially well off and be able to enjoy. I want the kid to enjoy trying to get that meeting with me or submit music to me to be able to get something for 50 dollars if they could. And that is what they represent.

How important is it to you to always keep doing charity and giving back?
It is extremely important. Charity and any sort of fundraiser that you believe in should be part of your normal criteria. I'm part of artist management and you know I will try to convince/tell Fab, Khaled or whoever I'm working with that we need to raise funds for this. We honestly map out our year and we’ll say you know this event is happening in the summertime or like for Halloween we got to make sure we have costumes for the kids or Thanksgiving, Christmas. All the normal ones. In the winter we do clothes drives and stuff like that.

I'm also involved with a really dope organization called Hashtag Lunchbag, where we feed the homeless once a month. It started in LA, then New York, now it's carried out all throughout the country.

What qualities do you look for in that kid who's trying to get a meeting with you?
I'm going to be honest with you: when I came in the game or when I was trying to enter in the business I knew a couple of people inside. I would always try to go see them and I would have to deal with waiting for hours and getting canceled on. I know that a lot of the time people do what's easiest for them and what is easiest for them is to cancel, not do it, push it off. I always told myself man if I ever make it, if I ever get to a position where people want to see me, talk to me, write me or anything as such I am going to make sure that if I can that I am going to do it. That’s just what it is man, it's called sacrifice. If I'm in a rush somewhere and I know I am going to be late and someone stops me like "yo man I been following you for years can i have five minutes?" Is being five minutes late really that serious compared to five minutes where this is this kid's only chance to speak to me? Not really. So opportunities like 123 Wish..this is what that is about.

And when that kid comes up to you, what kind of advice are you imparting?
You know it’s all relative. Each case is unique. Some just want to know about how to become executives some want to know how to get in the business. I give them the best general advice I can give like telling them to be consistent or being assertive, and pushing without being annoying or psychotic. Definitely not settling. Something I learned is never ever settle. I came up in like the Roc-a-Fella and Diddy era. And the objective was always don't settle. Keep pushing people are always going to say no and it is going to be hard but again it brings me back to what I was saying earlier it is always easy for people to say no. Never settle.

"Never settle" applies to your work ethic still. You're a true veteran, about two decades in. What keeps you going still, out here with like Khaled, still going in?
I always felt like if you're going to be in the game you have to just do it. I used to work in a supermarket when I was a kid and most of my co-workers couldn't wait till the time came for them to get off of work. They didn't know anything about the supermarket. They didn't know anything about where the fucking cereal was. I just knew that shit inside and out and I want to be the best that I can be. "The cereal is in aisle 7; the water is aisle 9." I want people to be confident where they are and be secure and really be engaged. So it’s like if I am going to be in the music business—engaged.

I used to be the anti social media guy not because it was wack but you know, I am a private person. Now social media is the wave and the internet has really taken over so if I'm in social media I am going to give you the best pictures, the best post, I am going to give the story you want to see. My point is if I'm in it I'm in it and I need you to trust me. Like when I sign you, manage you or you're with my record company I have to be engaged and I want you to be like "Damn this guy is everywhere and he's doing as much as he can do in a 24 hour span." How could you tell me what's popping in the club if you not in the club? How can you tell me what's popping on social media if you not on social media? I can't tell an artist what's best for them if I am not engaged. I'm doing something right and this not coming from a cocky  standpoint I am coming from a place that I need you to trust me. I am a representation of Roc Nation til the day I die and I am a representation of Jay Z, and everybody that works for that company. So that's my whole thing if I am in, you're in it. That half way shit don't mean nothing to me.

Who is inspiring you?
Honestly, Khaled. I don’t want to sound typical—I work with people because of our friendship and my admiration for them and me being a fan of them, being inspired by them. I am in a point in my career where—not to sound cocky but I work hard enough to choose who I work with. Just as many artists as I go to and say “Hey man I want to work with you” just as many people are coming to me saying the same. I’m building myself and the company I am working for and for those around me. And I do that by being inspired. You know Fab still here, 2001 still here still relevant just came off the Chris Brown tour, still got sneaker deals, all kind of brand deals. How many artist from then or still here now? Only a handful. Jay, obviously. Khaled—15 years we've been working together. Every six months we push ourselves. Like we’ll say we only had three hits last month? Fuck that we're going for six. Oh we only had two name brand deals? Fuck that.

Find more information about 123WISH here.

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