Leesa Dean: Adventures of a Web Series Newbie: Chapter 6 – Things Fall Apart

Adventures of a Web Series Newbie: Chapter 6 - Things Fall Apart

by Leesa Dean

Ok. Before I continue with the Rollo saga I’m gonna kick this off with first, saying R.I.P. to brilliant writer Chinua Achebe who just passed away and second, a few random unrelated observations from the trenches:

1) The word “genius” is bandied about at an alarming rate.
2) I’ve yet to meet anybody who’s an actual genius since I’ve started. Smart, yes. Genius, no.
3) Doing a web series is similar to having a serious disease in that when it jumps off, you find out pretty quickly who your real friends are. And the results, at least for me, have been surprising. And sometimes depressing.
4) When someone says they want to “build” with you, it’s usually a codeword for, “you’re never ever getting paid.”

So Rollo, that’s what you came for, right?

He calls, I agree to meet him the next day (and, btw, when I say “agree” what I really mean is: I couldn’t WAIT to hear why he was MIA.)

I meet him directly after yet another awesome YouTube meeting. Got to hang with Kai Alexandre from Potty Mouth TV (who’s putting together an absolutely incredible project) and Nick Uhas the rollerblading phenom (yes, we’re doing a collab and yes, I am GEEKED about it.) Jake from uber-successful/dope channel vsauce3 gave really great tips and let’s just say I have a lot of housecleaning to do including changing the way a lot of the thumbnails look. YouTube just changed it’s channel format. At first, I was skeptical about it, but after this meeting I’m not only sold, I can’t wait to change over (a lot of prep work for me cause it means doing a lot more animation.) One of the great things about the new format is everything looks the same on mobile. It’s gonna be dope.

Rollo’s waiting for me when I arrive at “our” coffeehouse. I settle in. Look at him. Something’s definitely up. He’s unpressed. Not exactly deflated, but I can tell his ego’s been taken down a notch or two.

There are problems with his other project. One of the TWO MAJOR ATTACHED CELEBS(!!) has bailed and it might now be in jeopardy. I’m thinking, Ok, I thought this project was a done deal. It turns out the celeb who bailed was how he got in in the first place. He’s holding on by his fingernails and, I’m guessing, scrambling to stay in the mix.

My mind goes wild. How is this dude paying the rent? Is he some low-rent, over-the-hill hipster male escort with a crazy ad on Craigslist? Card shark? Probably more like bowling shark, if that even exists. Sadly, he’s probably a telemarketer and mainly living off his girlfriend.

He stresses he’s still committed to helping me with Chilltown and says he can definitely make things happen. So in my brain, he’s now hard-shifted to “back burner” status. But he’s still got a couple of surprises up his sleeve…

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!

Leesa Dean: Adventures of a Web Series Newbie – Rollo


by Leesa Dean

Let’s call him “Rollo*.” Yes, he’s the fanboy I went out for coffee with. This is how it happened:

Every day I write to people. People with blogs, radio shows, who are influencers, essentially begging them to watch Chilltown and Lele’s Ratchet Advice Show. That’s part of the gig. Sometimes they write back and it’s great. We get interviews or featured. And we’ve been incredibly fortunate. Gotten a great outpouring from people. Been luckier than most. But more often than not, people don’t write back. At all. Good times!!! On a side note, if you’re into getting rejected don’t bother hiring a dominitrix to demean you or joining an online dating site. Simply release a web series.

So, last month I get an email from Rollo. Turns out I had written to a friend of his who loved both shows, posted them on his blog and Rollo saw them. Said he had a ton of connects and would love to meet to discuss the show. I ask around. Look at his Linkdin. He actually seems legit. And I actually kind of get excited. We agree to meet in the East Village at a coffee place, his choice, in a few days. And I do what anybody else in my position would: Google him and find his personal blog. And it’s dope.

He’s cool and he drops knowledge. About the tv business and digital frontier. And I’m thinking, worst case scenario, even if he can’t help the show, I can probably learn a lot from this guy. Yeah, he name drops like a champ (a little cheesy, but hyper-nerd that I am, I actually look at his FB page and he *is* friends with some of the heavyweights he mentions so I overlook it.) But more than anything, he talks about his escapades in the biz (he’s a producer) all of which are thrilling. A lot are from way back in the day, but still. I’m thinking: I. am. so. IN!!!!

The day arrives. I get there early, take out my ipad and just out of curiosity with a little time to kill, look at his blog and there’s a new update. And it’s a rant, posted the night before at 4am. And it’s World of Warcraft related. And it’s bugged. And he’s in his FORTIES!! And at the end he writes, “Well, I might be mad now, but at least tomorrow I’m meeting Lele.” And I think, FUCK, he’s a fanboy.

And, just like in Hollywood, at that very moment, he walks in.

* The names are changed and no links used to protect the massively guilty.

The 100% True Story of How I Taught Myself How to Animate So I Could Launch A Web Series


By Leesa Dean

About five years ago I was at a crossroads.

I’m a writer, lucky enough to have sold a few shows. One to a cable network, a few others to production companies. Unluckily, I’ve never had a show actually go into production. It paid the bills, more or less, but was incredibly creatively frustrating.

Chilltown, the show I sold to a network, was always special. I’m from the Bronx, grew up in and around hip-hop culture and felt it was frequently misrepresented. I wanted to do a show that my friends and I could relate to. Initially, I self-published Chilltown as a comic book (working with a great artist), got some press and was able to sell it as a series.

After three long years in development hell, the rights reverted back to me. It was one of the biggest let downs of my life.

So there I was. No representation (my manager/agent had left the business), no job, nada. Yet I had the unswerving conviction, based on essentially nothing, that people would like Chilltown.

I knew I couldn’t afford to farm it out to a production company (animation is wildly expensive) and crowdsourcing didn’t really exist back then, so I decided to do it guerrilla style. On the web. Solo. There was just one teensy caveat: I didn’t know how to animate. In fact, I hadn’t drawn anything since middle school.

I took a year and adapted Chilltown for the web while I taught myself the basics. Lived off my savings, a couple of loans from the bank of mom & dad and some temp jobs.

Every day, I practiced using downloaded tutorials and books, plus model sheets, done while I was at the network, as a guide. By the end of the year, I had written Season One as well as a second series and felt ready to start.

I hired actors I knew and cold-contacted comedians I found online. Everyone worked for free or a nominal fee. It was a real labor of love.

I spent the second year drawing. It was nerve-wracking because I had no idea if anything would ultimately work. I ended up completing over 400 pieces of background art and 200 characters. I was ready to animate.

The day I composited background art with the characters and got them to move was heady. It was the first time I realized: ok, I can do this. I spent nearly four months animating Episode 1. Making mistakes, starting over, making more mistakes and finally getting the hang of it.

In all, it took about five years to complete 140 minutes of animation from beginning to end: Seasons One of Chilltown and The Danger Squad (the second series; launching in July) as well as a weekly Chilltown spin-off, Lele’s Ratchet Advice Show. That included taking 14 months off when my mom got very sick and, ultimately died.

So, was it worth it? It was probably the most fun I’ve ever had. Turns out I love animating. But I’m now at a second crossroads: actually launching the series.



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