Leesa Dean: Sometimes Entering the Fast Lane Means Slowing Down

leles week in review

Adventures in Digital Series Land #116
by Leesa Dean

Things are getting intense. In a good way! My radio segment *just* went live on AM radio to a pretty big audience! The show, Lele’s Week in Review, is a 90 second parody of entertainment news done by my character Lele. I write, produce and voice it. It’s A LOT of fun.  And a lot to do. I bang out/record a new episode every single week.

Two radio stations have it: Rhythm 105.9 in Yuma, CA and now WWRN 1620 AM Urban Classics (as part of the Just Wake Up Morning Show every Friday at noon EST) which is in Lehigh, PA.  They’re both syndicated out to smaller stations. Total listeners so far: about 250,000. Not too shabby.

WWRN started as a digital channel, I met them when they interviewed me aboutChilltown, I had just started the segment with Rhythm 105.9  and they were interested. WWRN kept growing and growing and now, it’s finally made them jump to AM. Cool factoid:  WWRN is co-owned by former 1990’s phenom Damion “Crazy Legs” Hall from the R&B group Guy. I feel it’s a real opportunity for me to increase brand awareness.

Meanwhile, I’m working about 6 1/2 days a week on the new series. Post-production is so incredibly involved, it’s a much bigger chunk of work than I anticipated. I’m *hoping* the first seventeen episodes will be in the can by sometime in January but at this rate, who knows. And there are three additional episodes PLUS the trailer that have to constructed.  I’m getting bleary-eyed just thinking about it.

Also, every day, I spend a few hours knocking out a spec pilot script. I’m mentally raking myself over the coals with this one cause I feel really strongly about it and it’s….complex.  FYI, the secret to writing something that’s complex?  Keep it simple.  Or, at least, make it look/feel that way. Something that’s a lot tougher than it seems. I’m hoping this script will be in the can by the end of December.

And after that?  Three new writing projects–a short and two new digital series (which I’m hoping to be in production with by Spring.)

Like I said, it’s a lot.  So once again, I’m going to take it a little slower with this blog.  Only post once in a while and after the new series is in the can and I’m gearing up for promo, I’ll start again.  Mostly cause I’m hoping that my journey promoting and being out there will be helpful to people.

Til then, I’ll leave you with this from the great Frank Ze.


Leesa Dean is the creator of CHILLTOWN TV, a digital series to reckon with, and the new hit podcast “Lele’s Week in Review.” Learn more about Leesa HERE.

Leesa Dean: The Squiggle that is Failure

Adventures in Digital Series Land #114
by Leesa Dean

jazzatthenewzealandschoolofmusicConfession #1: Sometimes (ok, a lot of the time) I wake up in the morning and feel like a failure. Why? Duh. Cause my career isn’t where I feel it should be. And, partly, cause I had a Quick! Easy! Fast! kinda-sorta success when I started out. And since then? Well, let’s just say I’m trying to catch up.  This is not about depression, btw. I’m not depressed. In fact, I’m a happy person and actually pretty optimistic about how things will turn out .

The Background: I made a big rookie mistake when I started:  I actually believed my agent/manager would get me work. So I didn’t spend every waking hour networking and writing writing writing. Yeah, I had more ideas. Yeah, I worked on some. And wrote a few spec scripts.  But since right out the box, I sold a spec script to a network (with virtually no experience under my belt), I thought it would just magically keep happening like that.

Spoiler alert: It didn’t.

My first deal was so over-the-top good–thank you 800-lb gorilla attorney and (former) manager!–that I literally thought I could retire in a few years. And could have, based on that contract.

The Hitch: Retiring in a few years was based on one teensy weeny little thing. My show had to go into production.  It didn’t and ultimately I was kicked to the curb with the rest of the writer debris. Sayonara former agent/manager! Don’t forget to write! JK, you never did in the first place.

It is very very hard to come from something seemingly MAJOR to, well, nothing.  But ultimately, the whole confidence imploding, trial-by-fire shitstorm experience got me one good thing: my hustle back. Cause you can’t succeed without it.

Confession #2: I thought I was fairly unique, you know, with the whole success to failure trajectory (well, except for country singers, meth-heads and some has-been rappers). That everyone else who had experienced the initial kind of success I did had go on to even mega-better things.  And I was waiting for, as Mark Duplass has said, “the cavalry”to come for me.  “Hey you! We heard you were really talented, you know, with that deal you had. Where’ve you been? Want a job in my writer’s room?” Nope, nada, zilch. (Yeah, I got over that notion pretty quickly.) Plus, not for nothing, it’s super isolating to toil away (yes, in obscurity). Especially when you’re working solo. Those Capital F plus Everybody’s Doing Better Than I Am and It Sucks To Be Me thoughts tend to creep into your psyche.

Turns out my story isn’t unique. In fact, it’s pretty common. Lately– mostly cause I’m in the last leg of production and second-guessing every single thing–I’ve been reading a lot of stories from super successful people who’ve detailed their own “failure” narratives. And you know what? It’s been incredibly empowering. Cause I’ve seen that my struggle is pretty much par for the course. Just read this brilliant/harrowing/ultimately kick-ass redemptive account by wonderful writer Nina Bargiel who went from being in the writer’s room on Lizzie McGuire to cleaning shoes in a gym. And, coming back. With a vengeance!

You know that meme that crops up every now and then on FB? The one what shows a mixed-up convoluted squiggle as the real trajectory of success?  It’s true.

And all the choices I’ve made post my original fall from grace were pretty much on point. (First thing: don’t stop writing/creating/hustling. Second thing: don’t depend on an agent to get you work. That’s really not how it works.) And failure is part of that equation.  It’s what separates the metaphorical men from the boys.

So that whole waking up in the morning and feeling like a failure thing?  Yeah, it still happens.  But I own it and know it’s only temporary.


Leesa Dean is the creator of CHILLTOWN TV, a digital series to reckon with. Learn more about Leesa and the series HERE

Leesa Dean Gives Thumbs Down to ‘Thumbs Down’

Middle-Finger-Button

Adventures in Digital Series Land – #112
by Leesa Dean

Been so so busy I haven’t had time to do anything, which is why this post is late. Aside from everything else going on (animating/production work on new series, promos and writing a pilot), I just signed a deal with fledgling streaming VOD company Kweli TV.  They fell in love with Chilltown and now it will be on their platform in HD!! So I’ve been redoing all the episodes in preparation for the launch. A ton of work.

But something really big is brewing in the digital media world and I felt I had to address it.  That’s right, Facebook is planning on adding a dislike button (thumbs down) and people are going berserk.  And for a good reason. Given all the trolls, schadenfreude-mongers, ill-wishers and general sh*theads that populate an average timeline, people are bracing themselves for their videos to get tons of thumbs down. To make things worse, Facebook says it’s planning on DELETING any video that has more than 10 dislikes.  Talk about pressure.

When I first read about this I had, what can only be described as, a social-media take on the classic comedian’s nightmare: I dreamed I posted my latest radio show segment and all the hosts from one of the radio stations that carries the segment gave it a thumbs down.  Not only by clicking the button, but also by posting a huge image of the FB thumbs down.  To be fair, that joke did kind of suck.

Calming elements in this equation? Well, this has been happening on YouTube since forever and usually, trolls seem to want more attention so will post nasty venomous comments vs just clicking dislike. They normally want to interact.  Plus, on Facebook everybody can see who’s clicking the dislike button which probably will rule out your schadenfreude-loving friends. Hopefully. Plus videos that go viral (and I’m hoping or being delusional here) get shared a ton on Facebook. Which can work in your favor. Or not.

So I’m voting a distinct “thumbs down” for the upcoming dislike button.

Finally, tonight I’m going to the New York premiere of Chilltown star Victor Cruz’s NEW MOVIE, The Stockroom!!! To say I’m excited would be an understatement.  It’s being featured at the Urbanworld Film Festival and Victor not only stars in it, he wrote and directed it. Plus, Gil T, another Chilltown star is also in it. The movie just screened at the LA Indie Film Fest and won three awards (Best Screenplay, Best Feature and Best Actor!!!)  I’ll write all the deets in my next post.


Leesa Dean is the creator of CHILLTOWN TV, a digital series to reckon with. Learn more about Leesa and the series HERE

Leesa Dean’s Tale of Promotional Woe

promotionAdventures in Digital Series Land #111
by Leesa Dean

First, I’m finally over the hump. Meaning, about to start production on the last part of this new series. Something that should take about 6 – 8 weeks. Yes, I’m psyched! Also, a little scared. Not only about putting myself on the line again, but just the sheer volume of work ahead just promoting it is intimidating. I’m prepping so much stuff with so many plans I can barely see straight. But, it’s necessary. And I’m taking my cues from the big guys (even though I’m doing this on a minuscule level).

So what are the big guys doing?  Continuing to blur the lines between cable, tv and digital. If you’ve been on another planet (or, ahem, haven’t happened to read this blog where I rant and rave about it), things are now in full effect with execs and creatives from digital moving into cable and tv positions and visa versa.  And what that means for shows and series is: more and more content is being produced online to help promote shows. I thought it was really telling that The Daily Show with Trevor Noah hired Baratunde Thurston as a Supervising Producer for Digital.

Thurston has been at the forefront of all things digital content (he was the Director of Digital at The Onion) for many years plus, he did this which forever earned him my respect. It’s a big step for a show that’s that high profile, especially since all eyes will be watching Noah to see if he fills Jon Stewart’s shoes, to hire somebody with those specific internet credentials–someone who easily straddles both worlds but really and truly understands promoting on the internet–to set things up on twitter, instagram and snapshot.

Bits made just for social media that are perceived as original content but really promotional can drive the profile of a show way up. Amy Schumer’s Comedy Central show hasn’t had huge ratings but its social media sketches have gone viral. And the viral sketches that Key & Peele and Jimmy Kimmel have put out helped bring in huge audiences for them. At this point, it’s really becoming a necessity for all shows and the Daily Show’s hiring of Thurston was a smart move.

So if you’re a little guy, like I am, that just means it’s crucial to have ancillary content to help promote your series.  And not just one or two things. But a regular stream of stuff. Phew. I’m exhausted just thinking about what lies ahead.


Leesa Dean is the creator of CHILLTOWN TV, a digital series to reckon with. Learn more about Leesa and the series HERE

Leesa Dean on Shooting Yourself in the Foot

bullet-in-footAdventures in Digital Series Land – Chapter 110
by Leesa Dean

Been working like a psycho, trying to bang out these mini-episodes and it’s been tough.  Wanna have 35 in the can before I return to final animation production on the new series—hopefully within 2 1/2 weeks. It’s a lot.

Meanwhile, in the midst of all of this, I spoke with a friend whose script recently made it into the first round of a prestigious competition.  She wrote about it on Facebook and when I congratulated her, she minimized the achievement. That mini act of self-deprecation stopped me in my tracks and I thought I’d write about it. Mostly cause it’s something I used to do all the time. Until recently.

Why? Three reasons:

1- I had some success at a pretty young age and was used to people’s jealous reactions. It’s normal. It’s part of show business. It’s hard to take. I thought if I trivialized the good things that were happening to me, it would minimize some of the personal backlash.  (Spoiler Alert: It Didn’t.)

2- I come from the kind of family where it’s mostly considered bad taste to crow about success.

3- I was kinda socialized to be that way as a woman. It’s a subtle thing, but I’ve learned that part of being successful is acting successful and if you’re female and act successful, you just might get called a bitch. Or arrogant. Sad, but true.

Ultimately, I learned the hard way, in business (and in life) it’s a fatal mistake to be self-deprecating. And trivializing an achievement is just that. If you tell people, “Yeah, I won a Pulitzer, buuuuttt, it’s really no biggie”, people will believe you. And treat you that way. Like you’re somehow not deserving of that accolade. I’m not suggesting bragging about achievements, but own them, deal with jealousy and ultimately people will treat you accordingly.

On a final, unrelated note, Will Keenan is leaving his post as President of Endemol Beyond USA. Will reached out to me two years ago when he was still at Maker, offering me a contract there. It not only meant a lot to me that he believed in Chilltown but we really hit it off. Sadly we couldn’t come to terms contractually so the deal with Maker was not be but have stayed in touch. He’s a great guy and has done so much for the digital community. He wrote on FB today that he already has new plans in the works and whatever they are I’m sure they’ll be spectacular.  I wish him well wherever he goes.


Leesa Dean is the creator of CHILLTOWN TV, a digital series to reckon with. Learn more about Leesa and the series HERE

Leesa Dean Tells Us “How Tennis Saved My Pitch Meeting”

220px-tennis_racket_and_ballsAdventures in Digital Series Land – Chapter 106
by Leesa Dean

I am a tennis fanatic. Love to watch matches, love to play.  Did I mention I kinda suck at it? Ok, maybe not suck, but…I’m inexperienced.  Been playing for about five or six years (just working on my strokes) but only started playing games last year. And found out the hard way that playing games is dramatically different than just hitting a ball around.  Aside from strategy and learning different shots that are game-specific, there’s the pressure.  And it is insane. You’re dealing with ego (mostly your own: OMG, am I gonna fail?), stage-fright (OMG, everyone’s gonna see me fail!!!) and fear of failure (OMG everyone just saw me fail!!!)  But I really really really wanna get better and feel I have the potential to, ultimately, be a good player. So I’m sticking with it.

A week ago I found myself prepping for a pitch meeting. And the same fears I have with tennis were cropping up (yeah, the fear of failure thing). The worst thing you can do in a pitch meeting is have them see you sweat. I mean, who wants to buy something from someone who’s nervous about their project?

I’ve taken a ton of pitch meetings and normally don’t get nervous about them anymore because I’ve been told I’m “good in a room” but since I’ve been holed up a while writing/animating a bunch of new stuff, it somehow felt new.  And I had a butterflies.

I ended up doing a trick that a tennis buddy taught me: Walk the walk.  Meaning, act as if you’re totally confident. And ultimately, you will be.  I’ve started doing that while playing tennis and you know what? It works. I’m gaining confidence, feeling less pressure, not caring about failing and thinking I’m going to win. And I mostly am winning.

And it worked for the pitch meeting. I walked in with my partner and killed it! Don’t know what’s going to happen (I’ve walked in a killed a ton a meetings and they still passed–it’s very rare when they don’t at this stage) but it was a relief to rise above my fears and knock it out the park. I feel like I’m really back in the game.

Walk the walk, people!


Originally published on Leesa’s ChilltownTV blog

Leesa Dean Answers Your Question, “Does size matter?”

Adventures in Digital Series Land #105
by Leesa Dean

Ah, the age-old question: Does size matter?  Maybe not, according to the IAB.  And yes, I’m talking about online content. Specifically, how long episodes should be. This is a REALLY important consideration when you’re putting together a digital series.hmo-room-sizes-does-size-really-matter

For the past few years, the going practice was to have each episode be between 2-5 minutes long. Anything longer: a death knell.  And I kinda learned that the hard way.

When I started, I had absolutely no idea how long to make my episodes so each one ended up being between about 6-8 minutes. Or longer! My thinking was, it makes sense for vlogs to be shorter, but I wanted to show off my work. I was still thinking with a tv/cable mindset vs. a YouTube one.

On YouTube you can gauge viewer retention and see where people drop off. In fact, that’s the biggest way YouTube rates your videos. Episodes that have longer retention (and yes, huge views) are more searchable on the site. But retention trumps views in the YouTube world.

It makes sense to have shorter episodes, solely to keep eyeballs on your show. And to bulid up a fanbase. I believe shorter episodes lend themselves more to being shared. For a small indie series, my first time around, I didn’t get huge drop-off but I’m convinced that if my episodes were shorter, they would have been more shareable.

And while these new statistics show that people are are willing to watch longer episodes on mobile, I still don’t think it’s a great idea.  Especially if you’re a beginner.

This week my production partner and I had a strategy session with someone at a a major network.  He reinforced the smaller is better concept for digital but even he admitted some of this stuff is very hard to predict.

Either way, for the new series, I’m making the episodes shorter than I did the first time around. They’re all less than 5 minutes.The good things come in small packages model. Aside from trying to have something be funny and engaging, I’m hoping for more shareability this time around.


Originally published on Leesa’s ChilltownTV blog