Small Crowds, Big Lessons: My First Writing Job in Theater

(UPDATED June 2025)

Back in Denver, I joined Grafenberg Theater as a writer and performer in a show called 303’s & Heartbreaks. It was my first actual sketch writing job at a dedicated comedy theater — not something I made with friends or solo.

Up until then, all the writing I’d done had been just me. I was used to seeing my ideas through from beginning to end, without needing to answer to anyone else. For better or worse, it was just my voice. But this was different. This was a show. With collaborators. With notes. With a deadline.

Here’s what I learned.

Writing With and For People Changes Everything

Before this, I had only written for myself — performed by me, directed by me, usually filmed or staged by me. But this was a real sketch team. I had to write pieces that worked for other people’s voices, not just mine.

It was a shift in mindset. Not just "is this funny to me?" but "does this work for the group?" It stretched me in a way I really needed.

Grafenberg Was a Small but Mighty Operation — And I Was Proud to Be Part of It

I’d already been doing solo performances and variety slots for them — first at the Comedy RoomRoom inside El Charrito, and then at their own location on 21st and Larimer near Coors Field. The first venue was a literal hole-in-the-wall. I even helped build the new one (poorly — I’m no handyman).

This was one of the first-ever shows at the new space. The energy was experimental, raw, and collaborative — and I got to be in the middle of that. One of my favorite places to do stand up, improv, and sketch was Wrigleyville in Chicago. I had met some of my best friends and got so much stage time there. This was right by Coors and I was looking for something similar. I was excited to be a part of something new. I had only been a part of successful institutions that seemingly had no room for newbies like myself. I had no capital to invest with but I had my writing.

I Had to Learn to Dial It Back Without Feeling Like I Was Selling Out

My writing was pretty edgy at the time. I wasn’t used to filtering or notes. But I quickly learned that edgy for edgy’s sake doesn’t always serve the show. The tone had to fit the ensemble, not just my voice.

At first, it felt like selling out — but I realized I wasn’t producing the show, I was a part of it. And that meant collaborating, listening, adjusting. Taking other people’s suggestions and shaping the piece together.

That was my first real experience in something like a writer’s room. And it taught me: it’s not about ego. It’s about what lands. "Use every piece of the Buffalo," let's find out what works for this sketch.

“Do We Get to Keep the Sketches?” Changed the Way I Create

I knew to ask that but I didn't.

Someone in the cast asked, “Do we get to keep the sketches and characters we write?” And the owner said, “Yes, of course.”

That changed something in me. I didn’t even realize it, but I had been operating with a mental governor. Like I was always “saving the best stuff” for myself.

Hearing that I retained ownership gave me permission to go harder. It also reminded me that if you’re going to do this long-term, you’ve got to protect your IP. One of the sketches I wrote for that show actually had audio elements that ended up on one of my albums.

Ownership matters — even in small venues with 8 people in the audience.

I even made the poster

Sketch Comedy in Denver Was a Different Beast — and the Audience Wasn’t Always There

I had just moved back from Chicago and was trying to get a sense of what sketch looked like in Denver. I quickly realized: It was different and it requires different marketing, too.

Some nights we had no audience. Literally zero. We cancelled. Other nights, we’d get two drunk guys who wandered in, thinking it was a stand-up show. One of them shouted mid-show, “What the hell is this?! This is theater!”

They didn't make it more than five minutes, at most.

That moment made me laugh — because it’s exactly what sketch is. That in-between space between improv, stand-up, and theater. It’s the home for the weirdos who aren’t soloists but still have voices.

And yeah — I also learned to stop relying on Facebook to promote shows. I loved being a part of 303's & Heartbreaks. It was my first sketch revue as a writer-performer. It gave me much needed confidence.

I got to work on other shows and one-offs with Grafenberg. I had so much stage time every week and got to learn from the people who came in and out.

I'm so grateful for that. I got a sketch education while on the job.

It would've been great to get paid though.

Grafenberg Theater's Former Entrance (2025)

Bonus Lesson: Record Your Performances.

There’s nothing left of that show — no video, no audio, no script archive. It came and went. I got the experience, but I wish I had something to look back on. Don’t count on memory. Hit record.