Leesa Dean: Adventures of a Web Series Newbie: Chapter 4 – Can’t Knock The Hustle?

Adventures of a Web Series Newbie - Chapter 4: Can't Knock The Hustle?
Continued from, um, last time

 by Leesa Dean

So Rollo appears. Carrying a grande-sized coffee. Sits down. Orders another coffee. I’m transfixed. He looks different than I pictured (though admittedly, his pix are kinda obscured online.) Initial observations:

1) He’s rocking the burnt-out boho look: Paunchy. Hunched over a bit (from all those hours playing WoW, I’m thinking?) Longish, silver-tinged dreads with a pronounced bald spot. Filmy, aberrant, slightly chipped grayish teeth. A black motorcycle jacket that’s seen better days.  Overall?  Kinda got that Catch a Predator meets Crown Heights stylee.

2) He’s stranger and simultaneously more interesting in person. References lawn gnomes, transmedia and obscure MF Doom lyrics all in the same sentence!! Spits ever so slightly when he talks. Confession: I would probably pay to see his IG stream. Cause ya know it’s gotta be super private and super strange.

3) He admits he’s heavy into WoW. When someone his age (guessing late forties?) is *still* a huge gamer,  you wonder:  What else is this dude into? Cosplay?  Is it possible I’ve seen him traipsing around the Javits Center during Comic Con dressed up as Boba Fett.  Or worse, Hello Kitty?!?

4) He admits to being a fanboy!!  But he also says he really thinks he can help me sellChilltown to cable tv.  He name drops his connects and yes, some of them seem a little dated.  But they’re better than anything I’ve got right now.  And, as far as I can tell, they’re legit.  Plus, in person, he seems more like a fan/co-conspirator than fanboy.  At least I’m hoping?

So, yes, there are red flags. But I choose to ignore them. It’s incredibly seductive to have someone step in and virtually guarantee you a deal. Especially when you don’t have any representation.  Yet.  And especially when you’ve been working like a psycho to get exposure.  It would Just. Be. So. Simple.

We start making plans. Kind of.  Agree more to play it by ear and when the time is right, initiate something more formal.  It’s exciting and scary.  And a little bizarre.  I’ve had agents and managers and usually we lock in a game plan right away.  But this is all new terrain, so I’m winging it.   What I didn’t count on was, exactly how much he was too.

Watch all the Chilltown TV Episodes!

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