Among the various pop culture phenomena, artists, and entertainment entities that are treasured by Millennials, you’d be hard pressed to find two that have been as comprehensively consumed and revered as much as the long-running HBO series “Entourage” and the long-running musical career of Jay-Z. Love it or hate it, you watched “Entourage” until the end. Sure, most people ended up hating themselves for sticking out those final few seasons, but we just had to see what happened to the guys. Love or hate Jay-Z, you always listen to his new music. Both “Entourage” and Jay-Z are must-see generational phenomenons, and over the past month, they’ve become intertwined in a way that Mr. Carter might not have fully realized.

Jay-Z strikes me, and pretty much everyone else, as someone who knows what he’s doing, both musically and in the business world. His successful turns as a record label owner and clothing impresario have backed up his classic boast on “Diamonds From Sierra Leone (Remix).” He is indeed a business, man. Completing the lyric, people have, for the most part, let him handle his business, damn.


With the recent formation of Roc Nation Sports, Jay-Z will now primarily be handling other people’s business. Jay recently announced that he’s becoming a sports agent, and signed athletes like budding free agent Robinson Cano, budding WNBA star (is that an oxymoron?) Skylar Diggins, and budding Jets circus member Geno Smith. Yes, Jigga Man had to sell off his whopping one-fifteenth of one-percent stake in the Nets in order to get on the path to becoming a licensed agent (though he still owns a sliver of the Barclays Center, which should produce a nice payday in perpetuity if he so chooses). He’s gone from owning a piece of the Nets to possibly representing the pieces that the Nets own.

The trouble is, musicians don’t make good agents. Neither do actors. Neither do athletes. Neither do any other people who are anything except agents. I can’t speak as an expert on too many things, but being a talent agent is one of them. I’ve worked at a talent agency for two years and I can tell you that a distracted agent is an agent with unhappy clients. Being in the talent representation business is one of those things where you really can’t be dipping your toes in too many other places. Plenty of talent managers get into the producing game, but that’s usually under the guise of partnering with and helping to advance the career of a client. In California, at least, agents are legally prohibited from doubling up as producers, because it presents a conflict of interest. By law, agents are required to look out first and foremost for their clients, personal ambitions be damned.

What the hell does this have to do with “Entourage?” Well, think back about how many times Ari Gold got into a fight with his wife because he didn’t make enough time for his family. (By the way, thinking about it now, how great would it have been if Mrs. Ari’s name ended up being Ari as well? It would have been hilarious and the “Mrs. Ari” name would have made perfect sense). Of all the elements in that show, the Gold family issues were as realistic as it got. I have no idea what kind of husband and father Ari Emanuel, on whom Ari Gold was based, is, but I can tell you that when he was rising to where he is today, his life revolved around his clients in the same way that Ari Gold’s did while he made his ascent (I know he’s not real, just go with it). And do you want to know why Ari Gold had such a shitty family life and his wife was always threatening to leave him? Because he was a highly visible, highly successful talent agent! He had clients calling him at all hours demanding favors both inane and important, and he always had to deal with them. Agents are like football coaches in that their job is their life and they need to be at someone’s beck and call day and night. Thus, both agents and football coaches have a proclivity to be crappy family members. If you want to be a big time agent, that’s the kind of commitment that’s needed. If you have rich and famous clients, you need to be ready to deal with them 24/7, no exceptions. If not? Then the client will just go elsewhere and sign with someone who has more time for them, because someone always does.

Just because Jay-Z is highly visible, highly successful, and courting high powered athletes does not mean he’ll turn into a bad husband and father. And his star power may be enough to make athletes stick around and not stray, even if he’s not showing them love. In terms of agenting, though, I’m hugely skeptical. It goes back to what I said about artists being bad agents.

About a year ago, my department had a client who was in talks to shoot a docu-series style reality show based on her life. When discussing possible plot lines, she insisted that her agent (my boss) and I be featured in an episode, maybe while we’re in a meeting or on a call, because that would accurately portray her life. My boss immediately shot down the idea. Why? Because if the 100 other clients my boss represents turn on their TV and see her on a show, they’ll be livid. Imagine you’re an actor/host/artist, expecting that every day your agent is trying to create work for you, to get you on TV. One night, after you haven’t been on an audition for three months, you see your agent starring in some TV show. You’d be pretty pissed off, right? Besides not caring at all to be on camera, my boss knew that appearing on TV would make her look camera hungry, like she really wanted to be a star rather than committing herself to make her clients stars. She knew how it’d look if she was on a show and the vast majority of her clients weren’t. I admired her decision, and even though the series never ended up materializing, her logic and reasoning stuck with me.

If I’m a Jay-Z client and I see that he’s putting out music, I’d drop him on the spot. Are you kidding me? I’m an athlete, I’m going to get one, maybe two decent contracts during my career if I’m lucky. And instead of researching and putting a book together and developing negotiating strategies, you’re out recording music and going on tour? I’d be on the phone before you finished your set, asking why I haven’t gotten any contract offers yet even though we’re three weeks into free agency, but you found time to do a four hour concert. It’s an agent’s job to service and sell a client while maximizing every aspect of his or her career. That’s the job. Jay, if you want to be an agent, you can’t be in the studio or doing a show. Instead, you need to be getting dinner with some sabermetrics nerd on the Cardinals and convincing the nerd that your client is worth $100 million. That’s what an agent’s job is.

I have no idea what kind of agent Jay will be. For one thing, I don’t know what sport, if any, he’s going to specialize in. I also don’t know how committed he’ll be to his clients. Part of me thinks he’s just going to be a figure head at his company and let the “real” agents handle all the business. But that’s not a smart business model either. Every talent agent in Hollywood started somewhere: in the mailroom, as an assistant, as an intern, whatever. They’ve worked nearly every job there is to work en route to becoming a big time agent, and that’s what enables them to control their businesses so well. Jay-Z hasn’t paid those dues, and if he’s really getting certified and plans on running the show, I’m skeptical because his knowledge won’t be as expansive as it needs to be, and he’ll lack that in-the-trenches experience that all weathered agents have.

Jay is clearly a very, very bright guy. It’s not like he doesn’t know the representation business. He’s had reps for nearly 20 years now and has been in the entertainment industry long enough to know a good contract from a bad one. He knows how it works. But he doesn’t have a law degree. He doesn’t have 20 years of agency experience that most agents his age possess. What he has, obviously, is his swagger and persona. Geno Smith must think he’s the coolest thing going right now because he’s repped by Jay-Z. Of course, the two took an idiotic picture together on Instagram that’s landed Jay-Z in hot water because, as someone who’s not a certified agent, he wasn’t allowed to be present during any recruitment meetings. If that doesn’t make sense, realize it’s also the reason that agents can’t bring naked women into recruitment meetings either. It’s got to be strictly business, no funny stuff or bribes. But hey, look at Geno, he took a picture with Jay-Z and put it on Instagram! He’s the man! Give me a break. The only less interesting pictures on Instagram are of gourmet meals cooked by 20-something couples who are playing house.

Robinson Cano, you haven’t met Jay-Z enough times in your life? You really can’t just roll up to the 40/40 or wherever Jay’s hanging out and pop a bottle with him? I doubt that. Which is why, again, I’m baffled as to why you’d sign with him. Cano has a deal with Nike. He’s got the Yankees by the balls. He doesn’t need to look cooler or alter his image. Why sign with a guy who’s never negotiated a contract? Cano has one big deal coming his way after this season, and that’ll likely be it before he retires. He should be with an agent who’s done that kind of deal before. Then again, Neville Chamberlain could negotiate the deal and still net Cano $150 million, so maybe Cano’s thinking “I’m about to be rich forever, may as well let my buddy Jay-Z get a piece of the action to launch his agenting career.” That’s really the only thing that makes sense at the moment.

One of the more memorable “Entourage” scenes had Ari running in and out of temple during the high holidays, much to the chagrin of not only his wife, but the entire congregation, and the executive who he was hunting down in an attempt to close a time sensitive deal. Is Jay-Z ready to step out of Blue Ivy’s kindergarten graduation in a few years to calm down Geno Smith when Geno calls Jay for the twelfth straight day freaking out that the Jets don’t “value” him enough and he’s not taking the deal? Is he ready to cancel a month of shows because he’s got to negotiate seven different MLB contracts at once? Again, I know he can just hire minions and have his employees at Roc Nation Sports take care of things, but he says he’s becoming an honest to god agent, which requires a hell of a lot more than pawning the hard work off and just showing up a few times a year to shake hands. Is he prepared to tell clients that he couldn’t put their free agency packages together because he had to record “Watch The Throne Episode 2: Attack of the Thrones” with Kanye?

I’d like to think he knows better, and maybe he will devote all of his time to his shiny new business and its burgeoning client base. But if I’m a client, the moment I see Jay-Z do something artistically for himself while I’m still unsigned, I’m switching agents right then and there. Let’s hope that Jay’s seen enough of “Entourage” to find a balance in dividing his time between the two groups of people relying on him for their livelihood: his family and his clients. The only way to do that is to let down another group of people who rely on him: his fans. Sad but true, if Hov wants to be a great agent and a true family man, the music’s got to go.

I’m just fascinated to see how tempted he’ll be to leave the agency world and get back to music. And if he never really leaves music, well, then I think that will tell us all we need to know about what kind of agent he’ll be.