Dolly Parton Wants Your Side Hustle to Go Big

If there’s one thing Dolly Parton is known for, it’s her independent spirit. That’s a big reason why website company Squarespace hired her for its new Super Bowl ad.

“We wanted this ad and Dolly’s story to serve as inspiration for individuals considering entrepreneurship,” says Kinjil Mathur, chief marketing officer for New York City-based Squarespace. The spot reimagines Parton’s 1980 labor anthem “9 to 5” for the gig economy and recession, encouraging people to ditch their day jobs and, says Squarespace, “turn an after-hours passion or project into a career” with, of course, a Squarespace website. Parton even has a new song, “5 to 9,” a knowing wink to moonlighters in the title and chorus. Among the lyrics: “It’s hustling time … with a website that is worthy of your dreaming.” 

The Parton campaign is a way to widen the Squarespace audience and compete with rivals, such as Shopify and Wix, says Kevin Taylor, professor of entrepreneurship at Stetson University, which is in DeLand, Florida. The ad is one of several the company has run during the Super Bowl in recent years. In 2017, for example, John Malkovich, who used Squarespace for his fashion line’s website, starred in its commercial.

With Parton, Taylor says, “I see Squarespace try to make a play for middle America.” Parton evokes a scrappy entrepreneur outside of the coastal cities, he says. Consider, he says, how she “put Pigeon Forge on the map” with the Dollywood theme park in her Tennessee hometown.  

Parton says that opening Dollywood in 1986 had been seen as a big risk. “My business managers … thought I was making a mistake. But I believed in my dream and obviously I was right,” she recalls in a Q&A with Squarespace. She fired those business managers, she says.