Leesa Dean: Adventures of a Web Series Newbie


Chapter 18: The Whole Branding Thing (sigh)
by Leesa Dean

This week I was invited to a special YouTube screening. The invite said I was selected to attend, which was pretty cool (I literally couldn’t believe I was invited!) But, unfortunately, I couldn’t make it. I had planned to, even registered to attend, but was so involved working on this TOP SECRET PROJECT, I just didn’t have time. In fact, the night of the screening, I was up till 3am rendering/animating. The screening had top YouTubers discuss best practices for taking with advertisers regarding branding with a panel.

The truth: no advertiser is going to be interested in branding my show. Yet. You really need to have a substantial amount of subscribers/viewer retention for that. I’m doing well but not SMOSH well. I’ve got under 800 subscribers. I think I’d have to have at least 20,000-30,0000 (at least) before those kinds of conversations start to happen. It would have been interesting to hear what they had to say, though…

All of this has got me thinking that I’ve got to start being a bit more strategic. And what, exactly, does that involve? Before I launched, my game plan, roughly, was to releaseChilltown, then release the second show (which became Lele’s Ratchet Advice) and then the third full series (that is dramatically different from the first two.) But that plan’s been tossed.

Since I’ve built up a small but loyal Chilltown following, I’ve realized that before I even think about a second season or release the third show, I want to build up the Chilltownbrand and a bit more of my own brand (as a writer) first. Before I even think about doing a season two.

So I’m planning a relaunch. I’ve mentioned it a little before, but now I’m really putting it into focus. And it’s going to be quite a bit different than the original. So on top of everything else I’m doing, I’m spending a lot of time trying to figure out the best way to accomplish that. Animation is tricky because it takes forever to do, vs just picking up a camera and shooting. So I’m going to have to be really inventive if I meet my self-imposed deadline of, uh, sometime this fall!

I actually was pretty down in the dumps for a few days this week. Everything kind of caught up with me. This has not been an easy road. It’s way way tougher than anything I experienced when I was just shopping tv scripts (mainly cause you’re not only writing, you’re producing, you’re promoting, you’re promoting, you’re promoting.) One of the things that made me snap out of it was this article by Lee Jessup. It really put things in perspective. The takeaway for me was in also reading this in the about section: “Managers don’t sign a script. They sign a BRAND. A studio doesn’t call in an A-list writer for rewrites because of one script he or she wrote; rather, they bring them in due to the trusted brand they’ve established.”

I’ve only been doing this for 6 months. I’ve got a looooot ahead of me before I’m truly a brand.

Leesa Dean: Adventures of a Web Series Newbie, Chapter 8


by Leesa Dean

A lot of exciting stuff is going on. The biggie: Chilltown was listed by ABCNews/Univision as Web Series That Should Be On Your Radar!!!!! And we got an incredible review! Ecstatically happy about it. Also, did a ton of fun radio including Geek Soul Brother,Educated Insanity (on ChicagolandsportsRadio), The Bobby Pickles Show and KRYC Rhythm 105.9 FM !! Also released Episode 6 of Chilltown and people are telling me they love it. In spite of all that, there’s still a bit of frustration that always boils down to the same thing: How can I get more people to watch? We’re still a very tiny show in an enormous pool. Have a lot of plans in place for additional shows and specials that (hopefully) will make a little noise. But it’s a tough tough game. Much tougher than I expected. But, in all, a really good week.

And I heard from Rollo. Last Friday, went to another YouTube meeting and it was great! Met some cool people plus got to see the YouTube studios at Next New Networks NYC. Very exciting. They have a couple of green screen studios with pro lights and cameras. Some of the collabs I’m involved with will probably be done there. Part of the meeting involved having a tour and being shown the ropes (a prerequisite to using their space.) Their computers are probably a billion times faster than mine, so can’t wait to do some editing there. A guy name Chris Chan Roberson runs stuff there and he’s great. They had pizza and drinks after and everybody was schmoozing and just like clockwork right towards the end, my phone rings. Guess who? Rollo happens to be in the area and we meet.

He’s been having meetings to get his other project back on track and serenades me with more stories of excess and glitz. He’s been using every connection he has to rope in another MAJOR CELEBRITY (!!) to prove his relevance but things haven’t gone as planned. The week before he abruptly flew out to LA to attend a hipper-than-thou dinner party in a sad last ditch effort to hang on by his fingertips. A minor mix of dps, on-the-rise actors, Interscope execs and big shots from Vice and UTA. But nobody bit. His shine is gone. He’s used up most of his money. He cuts to the chase.

He knows someone who works at a cable network. It’s a long shot but they might be interested in Chilltown. Did I want to push up the schedule and take a meeting?

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.