As a junior copywriter at Leo Burnett, my first account was Reebok. Leo Burnett didn’t come up with Planet Reebok—that was the previous creative agency—but we were mandated to use it for their global campaign. We took that as a challenge to one-up Nike and be culturally relevant. My art director was a big comic book fan and loved the X-Files. We came up with this idea: what if all of Reebok’s signed athletes were actually from another planet? We cut together a ripomatic and presented it to the client, who wanted to make an actual movie starring Woody Harrelson and Rosie Perez. I shit you not. We were like golden boys who would be in charge of this global campaign. Eventually, more senior creatives convinced the client to go another direction. Two years later, Men in Black came out and made a gajillion bucks. Oh well.

The Sony PD150 is a hall of fame mini-DV camera back in the day. It was the 3-chip camera that opened the doors to digital filmmaking. I took a break from my ad career and bought one to experiment with my own web series. I wanted to write a character like Elaine from Seinfeld—a neurotic New Yorker with her own ideas about why we exist. Wendy believed we were all entertainment channels for someone called God, but she was too boring so God wasn’t watching her. She needed to spice things up to get God to notice her. The episodes were based on what gets attention—sex, violence, celebrity. When I cast Rose Stuart, the Wendy character took on a different spin. Rose didn’t play Wendy as a big loud character, she brought nuance. My first taste of post-production was getting a bootleg copy of Final Cut Pro and a 40 gig LaCie hard drive that cost 600 bucks, which I got from B&H Photo Video. This was a few years before lonelygirl15 (Google it). We shot in the World Trade Center, only to watch it collapse a couple of months later, and that was the pivot to Los Angeles and Hyphenate Land.

This was where we I started to evolve my docu-shooting style first done in the Wendy Channel. A friend asked me to create buzz for her reality series about a USC player auditioning agents. We made a companion series with improv comedy, releasing episodes weekly to match her show’s schedule. We got up to a thousand peer-to-peer pass-alongs via email links in the first month. Phil, the actor who played the agent, posted it on YouTube in 2005—before YouTube was YouTube. We were just making content and using whatever distribution existed. My favorite line from this pilot: “Cheryl Lynn wants to take him to Sizzler.” I didn’t even have an agent back then. Now I can’t wait to hear mine say, “A24 wants to take him to Sizzler.”

I always wanted to find a way to feature writing samples. After completing The Wendy Channel and arriving in LA with its larger pool of talented actors, I came up with a concept: literary readings in the style of George Plimpton’s fireside chats, but with a fourth-wall break. The readers are busy living their lives when they’re interrupted to do a reading. So now there are two stories happening—the actual story being read, and the crazy story around the reading itself. Like Russian nesting dolls, each layer reveals something more absurd. I bumped into Felicia Day at Whole Foods—I was the night editor on her recently shot network pilot—shared the Wendy Channel with her, and she agreed to do a reading in “My Best Guess.” It got accepted at the Dance With Films Festival in their shorts fusion category. Good times.

Before there were pharma commercials, there were these unbranded ones that flooded the airwaves. The creative brief and direction were very narrow and we squeaked this one through, where somehow Doug Flutie, a non-actor, got all his lines out in one take. Back before I was an editor, we sat in the bay and watched the editor do his editing magic on the Avid to get this to time. Now I know what that little weightlifter symbol on the keyboard means. We made a bunch of these forgettable commercials, but I was a permalancer at the agency, they liked me, and I made enough money to buy a co-op studio in New York. The OGness of this commercial campaign is symbolic of the crazy road that my creative journey took me on.

Speaking of roads, I also pitched a balls to the wall campaign for a dying car brand—one that the head of the entire global agency said was the most creative and original work the agency needed to make. This? Is not it. Like many campaigns at Burnett, the powers that be rode in on their overworked donkeys and thought they knew better. But I was still a middleweight writer learning the game. I still got to make this, and we found joy in the execution—we used Simpsons-inspired music that made it fun. Taking a page from working in entertainment, where victories are hard to come by, here’s something I learned: “You celebrate the little wins because any win is better than no win.”