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Roc Nation SVP Lenny S Reveals Why He Passed on Signing Wiz Khalifa

"Sometimes people don't realize, it could really just be a bad day."
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It's widely assumed among the artist community that if a major label A&R hears a record and doesn't subsequently contact its creator, he or she must not have been impressed with the material, but that isn't always the case.

In a newly-released Best Seat in the House interview, Roc Nation senior vice president and longtime A&R Lenny Santiago was asked by host Hovain Hylton to name an artist whose music he heard but "passed" on signing. After struggling momentarily to think of an artist—which either suggests he was caught off guard by the question or was trying to decide which current star he could name that would be the least embarrassing—Santiago settled on Wiz Khalifa, who he says was "dope," but "never moved on."

If Wiz was dope, as Santiago states, why wasn't there an attempt to sign him? According to Santiago, quite often when an A&R hears an artist for the first time, they might just not be in the right place mentally to fully appreciate what they're listening to.

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"I think we all miss out on stuff. I live with the motto 'live with no regrets'. I can't even harbor that kind of energy. But I've missed out on stuff that I like and that I love. Sometimes it's my fault, sometimes it wasn't—I guess probably one of the most recent or distinct was probably Wiz [Khalifa]. Jay had an attorney that worked with him at the time, Jennifer Justice, love her name by the way—Jennifer Justice, and she was a lawyer—and she knew Wiz really early on or was connected to him and she would give me demos. I heard it and thought it was dope, but I never moved on it. And then Wiz became who he became and that's great. But yeah, I'll admit it, there are times when people have come or—sometimes people don't realize, it could really just be a bad day. As music executives, sometimes we're listening to music 20 hours out of the day, and you may catch somebody who will be like, 'Yo, listen to my stuff,' and it could be cool, but your mind, mentally, you could really be gone. And not be there. And not give it the attention that's needed." —Lenny S.

It's unclear when Santiago first heard Khalifa's material, and Hylton failed to follow-up his answer by asking for a time and place reference, but given that Wiz signed his first record deal with Warner Bros. in 2007, after Rostrum Records president Benjy Grinberg came across his mixtape material in 2005, it's likely Santiago wasn't actually kicking himself until 2010, when Wiz signed a new deal with Atlantic Records and released his eventual No. 1 single "Black and Yellow."

In a way, Santiago's explanation sounds a lot like the standard relationship break-up line, "It's not you babe, it's me." If an artist makes, let's say, experimental R&B or a fusion of jazz-funk-rap, and an A&R listens to the record for the first time at 10 p.m. on a Thursday, after streaming new songs for 15-plus hours a day for four straight days, it shouldn't be at all surprising that the music might not connect at that moment. 

At the same time, though, artists need to understand that not every A&R at every major label can or will appreciate the sound, style, and direction of your music—no matter what time of day they press play. Some will get "it," some won't. The biggest music executives in the industry have missed on some of the biggest artists in the world. Fat Joe, though not a label A&R, passed on signing Eminem on several occasions, Diddy passed on signing DMX and Akon passed on signing Drake.

"People forget sometimes that we [are] human," said Santiago. Exactly. A&Rs are just like the rest of us, putting their pants on one leg at a time.

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