‘Real Talk’: 5 Questions About the Big Game with Squarespace’s David Lee

“This is totally serious.” That was the first line of Squarespace’s press release for its 2015 Super Bowl ad.

That spot from the leading website building and content management system starred Jeff Bridges and the Squarespace-built website, where users could buy Bridges’ sleep album. (Sales went to charity.)

Well, Squarespace is back for the Big Game in 2016 and, once again, it has to insist this is serious.

This year, wannabe football commentators Lee and Morris (hit comedy team Keegan-Michael Key and Jordan Peele) will provide live running commentary on the Super Bowl via the Squarespace site Real Talk. Except Lee and Morris, thanks to IP issues, cannot mention the name of the game, the details of the game or even what sports the game is. Squarespace is an official Big Game advertiser, with spots showing pre-game and during regulation play.

With lesser performers, this requirement could be a serious problem. But with enough pre-event promotion, this restriction might make Squarespace’s stunt more appealing to curious audiences. Indeed, in its promos, Squarespace is hyping the restrictions such as in one native ad on Key and Peele demographic-friendly Gawker’s Deadspin: “Will anything malfunction during the non-sports middle of the game, wherein things frequently malfunction, and serve as annual evidence that the nation in which this game is taking place has Turned Its Eyes Away From God?”

brandchannel spoke with David Lee, Chief Creative Officer at Squarespace, about the upcoming event.

brandchannel: This will be Squarespace’s third year at the Super Bowl. What is it about the event—besides the tens of millions of viewers—that makes it an attractive fit for the Squarespace brand?

David Lee: There are very few moments when you get the opportunity to tell a story to a hundred million people. This isn’t just about football, it’s a moment in time that transcends a variety of groups and interests. It’s also the only time where people genuinely look at ads as part of the entertainment. This allows us to get creative with our ideas and show off our brand message on the biggest stage.

bc: Is there any nervousness about the tricky way in which Key and Peele will need to be relevant to game day without actually mentioning the game?

Lee: We have always been aware of the legalities around the Big Game. We think part of what will make the “Real Talk” broadcast so entertaining lies in the fact that Lee and Morris will have to tiptoe around these obstacles for the entire game. This hurdle is really part of the fun, and highlights the creative nature of what we’re trying to do.

This campaign is the perfect outlet for both Peele and Key to showcase their talents. It just happens that their idea was to do a comedic, four-hour live improv experiment on Squarespace. It’s a perfect demonstration of what’s possible on our platform and we hope it will encourage others to do amazing things.

bc: Is simply trying this an automatic win for the brand? How will Squarespace measure the success of this ambitious stunt?

Lee: This is our third trip to the Super Bowl and we’ve learned a lot from our two previous appearances. I think the main takeaway is that in order to stand out, you have to be brave and take some calculated risks. No one wants to make an investment this big and be forgotten. It’s simply too big a stage to play it safe and go unnoticed.

That said, having a live broadcast throughout the entire game certainly feels like our most ambitious effort to date and we’re excited to see how audiences respond. We’ll be measuring everything including site traffic, new subscribers, sentiment, press mentions and even impacts on recruiting.

But most importantly, we’re looking to transcend pop culture and create a moment in time that people will remember. We’re not necessarily looking for people to sign up and start a website right after our commercial airs—but if we do something memorable that keeps us top of mind when our customers are ready to start their website, I feel we’ve done our job.

bc: Squarespace makes it a point to proudly state that it is “Made In New York.” How does this connection to the city inform and benefit the brand?

Lee: We’re proud to be born and raised in New York City. I think there’s a unique foundation to companies that call this city home. We’re heavily influenced by design and culture, the architecture that surrounds us, and the diversity of people in this city. Being headquartered in SoHo and colliding with the sights and sounds and little nuances we see every day really informs our brand and our values.

bc: What is your favorite Squarespace-built website of all of the thousands? And why?

Lee: There are so many, but because this one is fresh out of the box, I’m always going to go with our latest and greatest: Real Talk. Everything we do at Squarespace is built on Squarespace. We use every opportunity to prototype and test ideas that we feel might be useful to our customers. In this case, a live blogging template is something we have always thought of as an interesting concept, but sometimes, ideas don’t materialize until there is an immediate opportunity like this one.

With Peele and Key, this seemed like the perfect time to try and create a new design tailor-made to their unique abilities. What better way to stress-test a new concept than to launch it in front of millions of people? Who knows, perhaps we’ll learn a thing or two and turn this design into something anyone in the world can use in the near future.