Guest Post: Here’s How to Get A Web Series Off The Ground

I have been a comedian for about twenty years. During the first five of those years, I was also an elementary school music teacher in NYC. I was teaching kids how to play “Hot Cross Buns” on the recorder by day and performing at open mics by night. After five years, I left teaching to become a full time comedian but those memories have stayed with me, kind of like PTSD.

A few years ago, my friend and writing partner, Hollis James, came up with an idea for a show called “Teachers Lounge” (the missing apostrophe is intentional). I would play the music teacher at an elementary school, Hollis would play the janitor and we’d always be hanging out in the teacher’s lounge. Comedians would guest star as faculty members in each episode. We would script it but allow the comedians room for improvisation, too. It was a simple idea but we immediately thought it had a lot of potential.

After pitching the idea around without much luck, we finally decided to shoot it ourselves. I realized after twenty years as a comedian, I was friends with some of the best in the business. We could reach out to them and see who we could get on board. To our amazement, we were able to assemble an all-star cast that really surpassed our wildest dreams featuring Jim Gaffigan, Lewis Black, Janeane Garofalo, Judy Gold, Judah Friedlander, Todd Barry, Rachel Feinstein, Jim Norton, Dave Attell, Michael Che and Ted Leo.

Getting superb talent was one big part of the equation. Another part was being able to organize a full professional production. A third was being able to afford a production of this scope. Although it’s a web series, we wanted to shoot it with a full crew and make it look as professional and polished as possible. We decided to do a Kickstarter campaign to crowdfund the production, allowing folks to help us cover the myriad expenses involved. We also got very lucky in that Snagfilms (Indiewire’s parent company) came on board as distributors, and they are featuring “Teachers Lounge” on their new comedy channel Thundershorts, which launches tomorrow. They have been extremely supportive and helpful in seeing “Teachers Lounge” get completed. 

Doing a Kickstarter has also resulted in some very unexpected and special moments. A few weeks ago, I attended my nephew Kieran’s 10th birthday party. He specifically asked for cash rather than birthday presents. After opening all his cards, he announced he would be donating all of his birthday money to my Kickstarter campaign for “Teachers Lounge.” My brother, Dave, had tipped me off ahead of time, insisting that I accept the money because it meant so much to Kieran to be able to help out. I was speechless. When a ten year old hands over his birthday money because he wants to help you out, it’s pretty overwhelming. 

Then, this past weekend a waiter at a comedy club came up to me and introduced himself. It turns out he was a former student of mine (now in his twenties) and he mentioned how proud he and many former students are of my comedy career. He wished me luck with “Teachers Lounge.” It was very unexpected and touching. I thanked him and we played an impromptu duet of “Hot Cross Buns” for old times’ sake.

I’ve learned many lessons in working on “Teachers Lounge,” not the least of which is trust your instincts. We believed we had something special but we had to continuously keep pushing, even when things got stalled. There are a million opportunities to give up or put it off, but when you continue to push forward and take risks, you often see progress in ways that you couldn’t have envisioned. 

Twenty years ago I was an elementary school music teacher sitting in a teacher’s lounge dreaming about becoming a stand up comedian. Twenty years later, I’ve co-created a comedy web series with the guy I started in comedy with, Hollis James, and featuring some of the very best comedians in the world. I’m grateful for every step in the process and for everyone who has contributed, in ways big and small, to creating “Teachers Lounge.” It feels like graduation day. Watch a preview of “Teachers Lounge” below: