Leesa Dean: Adventures of a Web Series Newbie – Chapter 5


Penny For Your Thoughts?
by Leesa Dean

Things keep moving. Rollo and I talk a couple of times a week, mostly on the phone. He’s working on another project that just sounds huge. Two VERY MAJOR CELEBRITIES are attached. It’s a movie. It’s sci-fi. It involves a franchise. He got in through the back door because of his connects. What’s his participation?  Well, that’s a little nebulous. Yet, it’s thrilling. He’s like Scheherazade, spinning out tales of hope. If things work out like that for him, how incredible is it gonna be for me!

He admits he’s treading water financially. How does he support himself? I don’t even wanna guess. It would pierce my expectations and I know that. He’s not the only iron I have in the fire, in fact, he’s just one teensy one, but his stories and the potential weight they carry are mesmerizing.

I find out even more exotic things about him and, unbelievably (thank you, Google), they’re all true. Most of them are from back the in day and his exploits are rich with swanky VIP room scandal and excess. Close encounters with Halle Berry, Rza and Rutgar Howard! Tales of opulent tasting dinners in hyper-exclusive joints and crazed illicit backroom escapades. He talks to me like I’m one of the guys. And it’s dope.

And then, I don’t hear from him.

Weeks go by. Meanwhile, I’m working like a psycho. Promoting Chilltown, writing and animating new Lele episodes. Doing a lot of radio. Reaching out to new people every day. It’s intense and crazy and 24/7 (you know when you tell your cat, “Penny for the thoughts!” you’ve been in the hole waaayy too long.)

I break it up by going to a couple of meetups. The web series community in NYC is pretty small and by now, I’ve met a lot of the players (more on that soon.) Everybody’s so supportive and cool. It’s great to be a part of. I spend a full day at a YouTube meetup. They trot out some YouTube celebs and their stories/channel successes are absolutely awesome and inspiring, particularly Charlie Dodd from Improv Everywhere and JR fromJR Sports Brief. As part of the meetup, we partner with fellow creators and write/film on-the-spot collabs that everybody votes on. My team, including Yusef Lateef and Mike Mac, wins! And yes, future collabs with them are in the works. It’s a lot of fun and it takes my mind off everything.

We all retreat to a bar for celebratory drinks and schmoozing. And just as I’m leaving, my phone rings. It’s Rollo.

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