Squarespace flips the script on the classic Dolly Parton anthem “9 to 5” with a bold, musical tribute to side hustlers, dreamers, and after-hours entrepreneurs. Set to a remixed version of “5 to 9,” this ad celebrates the creative energy people pour into their passions after the workday ends. Squarespace positions itself as the website builder for those turning dreams into businesses—one late night at a time.
The Formula (That Works at Any Budget):
Remixed Pop Culture = Instant Recognition
Reworking Dolly Parton’s iconic song immediately grabs attention. It’s nostalgic, unexpected, and speaks to a modern audience redefining work.
→ Lesson: Leverage pop culture in a fresh way to create immediate emotional connection.
Dreamy Visuals = Aspirational Energy
The ad transforms a dull office into a fantastical dreamscape where people dance, design, and build their side businesses. Every frame feels like a celebration.
→ Lesson: Visuals should match the aspirations of your audience—energize them, don’t just explain to them.
Side Hustle Spotlight = Deep Relevance
From candle makers to dancers, the ad showcases real people doing creative work after hours. These aren’t corporate personas—they’re relatable, modern entrepreneurs.
→ Lesson: Show real people doing inspiring things with your product to build genuine credibility.
Squarespace as the Enabler = Quiet Confidence
The product isn’t pushed hard—it’s simply there, enabling all this magic to happen behind the scenes.
→ Lesson: Position your product as the invisible power behind your customer’s success story.
Humor & Vibe Breakdown:
While not overtly comedic, the ad has a playful and whimsical tone. The choreography, styling, and surreal transitions give it Broadway energy with a wink. It’s fun, uplifting, and leans on joy rather than jokes.
Final Verdict:
“5 to 9” isn’t just an ad—it’s a movement. Squarespace taps into the side hustle zeitgeist and makes the viewer feel seen, celebrated, and inspired. It’s stylish, empowering, and perfectly positions the platform as a tool for dreamers building their next big thing—outside office hours.
BRAVE-o-meter Score:
B-9 | R-9 | A-9 | V-9 | E-9
BRAVE – 9.0/10
Watch the full ad & learn more:
Website: Squarespace
LinkedIn: Squarespace
