Penny Wise

In writers’ rooms, Prentice Penny learned a lot of the things you might expect.

Like how to execute a vision and the importance of trusting your gut when it comes to storylines.

But while writing for shows like Happy Endings, Scrubs and Girlfriends, the L.A. native also learned the unexpected. “I started to be more exposed to things I thought were a little bit out of my attainability,” he says.

Enter truTV’s Upscale with Prentice Penny, an unscripted lifestyle series premiering March 21. It finds Penny, now the showrunner on HBO’s Insecure, exploring ways to live an “upscale” life — through fashion, travel and, yes, shopping. In each of the 12 half-hour episodes, Penny enters worlds that could feel intimidating and meets with an expert who offers expertise and accessibility.

“You never see people of color talk about this stuff,” says Penny, who wanted the show to be diverse. So Upscale features a brewery run by two women and a nail salon owned by an African-American man. “It’s important to me to go against what you assume these worlds look like.”

He also inserted a lot of his own life into the show, whether it’s a flashback to buying really bad cologne for a high-school date or referencing his father’s strict disciplinary style. “My personal experiences lead me to this moment. In being very specific [about them], it kind of becomes universal.”

Growing up, Penny spent a lot of after-school time watching TV with his grandparents — “probably not great, but it worked out,” he allows — but it was a summer high school writing program that made him realize television could actually be a job. “I did that for two weeks,” he says. “And I was like, this is all I want to do for the rest of my life.”

This article originally appeared in emmy magazine, Issue No. 2, 2017