Leesa Dean: Adventures of a Web Series Newbie – Rollo

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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.

4 thoughts on “Leesa Dean: Adventures of a Web Series Newbie – Rollo

  1. ChilltownTV says:

    Thanks for posting!!

  2. mag_pie_chronicles says:

    What a great post!! Looking forward to finding out what happens :O

  3. anne silverstein says:

    And then what happened?

  4. ChilltownTV says:

    Find out in Chapter 4….

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