Super Bowl Ads

Squarespace Is Going All in With a Super Bowl Ad Starring Keegan-Michael Key and Jordan Peele

Squarespace Is Going All in With a Super Bowl Ad Starring Keegan-Michael Key and Jordan Peele
Image credit: Squarespace
Guest Writer
2 min read
Opinions expressed by Entrepreneur contributors are their own.

Making its third appearance, Squarespace -- which has long advertised on podcasts and in print -- is doubling down on expensive Super Bowl commercials. But it is going for something different this time around.  

The New York City-based website-builder platform made its Super Bowl debut in 2013 with a relatively straight-forward 30 second ad and ran a buzzy, bizarre spot featuring actor Jeff Bridges last year that directed viewers to a microsite created for the occassion.

For 2016, it’s again changing strategies. While the company is tightlipped about the specifics of its 30-second spot that will run during the big game, one thing is certain: it’s going for laughs. Comedians Keegan-Michael Key and Jordan Peele, best known for their Comedy Central sketch comedy series Key & Peele, play two “ridiculous characters,” says company founder and CEO Anthony Casalena. “They’re two guys who pour all of their passion into a crazy idea, and use Squarespace to bring it to life.”

Related: Has GoDaddy Already Won the Super Bowl?

Clearly, despite the enormous price tag -- that 30 seconds of airtime will cost around $5 million -- Casalena views the Super Bowl as a savvy investment. Last year, nearly 1 million people visited Jeff Bridge's Squarespace website as the commercial aired. It also got a burst of additional press coverage after it aired. “Jeff was promoting a movie, so he was asked about it on Jimmy Kimmel,” says Casalena. “It was crazy.”

While Key and Peele may not have the same name recognition as Jeff Bridges -- “Do you know them?  I always have to ask!” Casalena says -- their popular sketch show proves they can generate plenty of viral, YouTube-friendly buzz.

Besides the Super Bowl, the company also plans on airing original spots at this year’s Grammy and Oscar awards.

Image Credit: Squarespace

Related: During Super Bowl, the Real Action Will Be on Social Media (Infographic)

More from Entrepreneur

Brittney's a Certified Financial Planner who can help you manage your business and personal finances and navigate the ups and downs of starting a business.
Jumpstart Your Business. Entrepreneur Insider is your all-access pass to the skills, experts, and network you need to get your business off the ground—or take it to the next level.
Create your business plan in half the time with twice the impact using Entrepreneur's BIZ PLANNING PLUS powered by LivePlan. Try risk free for 60 days.

Latest on Entrepreneur