Leesa Dean: Adventures of a Web Series Newbie

buildyourownfuture-tvwriter.comChapter 34 – The Pep Talk, Part 2 (Build Your Own Future)
by Leesa Dean

So. As promised, the Rollo Pep Talk.

We met at a tiny Turkish restaurant/bar in the East Village. Ordered cocktails (I sure needed one after spending time visiting my friend in Bellevue) and Rollo started talking.

He had hit rock bottom professionally. His deal, which was tenuous at best, had finally fallen apart. It was an enormous blow to his ego. I mean, this was a guy who ten, fifteen years earlier had been a player. Maybe not a huge one, but a player nonetheless. But time had partially eroded his connections and unless you’re active doing stuff that people know about, you’re dead to them, professionally.

He was actually talking about quitting the business for good. His girlfriend was pressuring him. It’s hard when you’re consistently not making any money. He didn’t want me to shore him up. Or so he said. But I did anyway.

He has a lot of experience in the business and I told him he just needed to reinvent himself somehow. Performers do it all the time. I did and I’m not even a performer. I was a writer, felt I was spinning my wheels and taught myself how to animate and now, even if everything somehow ends up failing for me, have a lot of options as a freelancer.

I suggested finding some niche he really liked and find a way to start out as a consultant. Figure out something online to do. Maybe start a small Youtube network. It’s not an easy undertaking, but it’s a way of re-branding yourself. I’ve found, particularly after launching Chilltown, that marketing to a niche community works the best. You not only build up genuine fans–people who you actually become friends with–but it’s easier vs trying to reach everybody all at once. If I were farming myself out as a consultant, I’d start with something smaller and try and build from there.

Is doing this gonna be easy? HELL no!! Right now, the market is glutted with everybody and their uncle trying to get in the mix. It’s so easy to DIY (and YES, click on this link–if you haven’t seen this movie from about 15 years ago, watch it now–it’s great! If Mark Borchardt were starting today, he’d be doing a web series.) that even people with zero experience/ability are jumping in. And some of them are becoming successful. So to get through the noise, you have to find your market, however tiny it is.

So I think he’s gonna do it. One thing for sure, he has nothing to lose at this point. It’ll be interesting to see what he comes up with.

About ChilltownTV

I’m primarily a writer. Sold a few series to tv networks and production companies but never had anything get on the air. So I taught myself how to animate and completed 3 digital series, launching two. The first, Chilltown has been named one of “Five Web Series That Should Be on Your Radar” by ABCNews/Univision and a “Show to Watch” by Tubefilter. The second, Lele’s Ratchet Advice Show, garnered a fanatic cult following. As a result, I now do Lele’s 60 Second Wrap Up, a weekly comedic entertainment report (which I write & perform) that airs on urban radio stations Rhythm 105.9fm and the Just Wake Up Morning Show on WWRNfm.

One thought on “Leesa Dean: Adventures of a Web Series Newbie

  1. ChilltownTV says:

    Thanks for posting, LB & Munchman!

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