‘Trailing’: How a Bad Job Turned Into a Web Series

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Photo Source: Julia Burlingham

Steven Phillips-Horst had reached a turning point. He knew it was time to get out of politics and pursue his creative passions. He knew it was time, partially, because he got fired.

Phillips-Horst worked for a Democratic political consulting agency that managed campaigns throughout the country. “It was somewhat disillusioning, because everyone in politics is not working in service of their progressive ideals as much as you want them to be,” he says.

He had already started writing the script for “Trailing” when the hammer came down. “I was, like, ‘Maybe I shouldn’t do this.’ I was on a campaign trip in New Mexico where I lived in the campaign manager’s house in a development. I would drive down to gorgeous Albuquerque and write Facebook posts for a guy who didn’t win. The day I got back, which was also my birthday, my boss took me to breakfast and fired me.”

Good thing he did. “Yes, this is a revenge Web series, but I also feel bad for those people,” Phillips-Horst says. “When you service someone else like that, it diminishes your sense of self.”

“Trailing” is a sharply incisive and funny series featuring Phillips-Horst as the lead, an employee at a hapless political consulting agency (sound familiar?) that deals with terrible clients. Phillips-Horst’s equally hapless boss is played by the Upright Citizens Brigade’s Joanna Bradley.

“She brought something to the role that I wasn’t even anticipating. It’s somewhat more—I hesitate to use the word ‘absurd’—but something like that, and it informed the direction of the show,” Phillips-Horst says.

He found Bradley and the rest of the cast, including “The Slope” actor Annarose King and Lily Marotta, through auditions. “It was so fun to have people audition for me. It’s really rewarding to see people fighting tooth and nail for your affection. I’m sure they’d all be really offended. Like, ‘I trucked out to DUMBO for this?’ ” Phillips-Horst says with a laugh. “I looked at friends, the UCB website, if people had videos or something I watched them; that’s how I found my cast.”

Phillips-Horst says he got lucky when it came to his actors. This was his first foray into Web series, and with the online world, he happened to luck into a “chill” environment. “I was really stumbling and flying blind through this process. Since I’ve done this show, I’ve done more things, and now I look forward to when you put a crew together.

“I did not have foresight [when creating the series], I just got lucky. I had some ladies who were very, very funny, chill, and great to work with.”

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