The Single Greatest & Most Graphic Squarespace Ad

If you've heard a podcast or two, you've no doubt heard a Squarespace ad. Or if you're jamming out on Soundcloud. Or if you've been in a NYC taxi. Squarespace advertises plenty. But the best part of Squarespace's podcast advertisements is the freedom they give entertainers to create those advertisements.

If you spend enough time watching the #Squarespace hashtag on Twitter, you'll notice people have their favorite podcasts and ads. I've seen fans of RuPaul, Marco Arment, Back to Work, Slashfilm, and Indoor Kids call out their favorite ads, alongside the scores of people loving or hating Squarespace's mash-up tracks from Jai Wolf and Geographer:


But none of them hold a candle to stand-up comedian Duncan Trussell.

Before his conversation with spiritual leader Jack Kornfield in Episode #148, Trussell unleashes an epically nightmarish and existential exploration of what it means to build (or not build) your website with Squarespace.

The stand-up comedian has a knack for explaining things in a wildly spiritual and psychedelic way. In Episode #148, he does not disappoint. (You can hear the NSFW ad here, two minutes in. It ends about ten minutes in.)

The Good

After reading the features of the platform without slipping, the copy quickly breaks down to so much more. Trussell poetically equates website design to technologically fishing in the digital ocean and throwing a boomerang into the bits and bytes of the Web.

He even characterizes website design as a form of idea sex:

Don’t you want to see what happens if you extend your technological proboscis and shove it deep into the warm innards of the Internet to see what kind of weird stuff is gonna come back?

The Bad

Then he goes down an existential wormhole. He admits his own shortcomings when he tried to become a web designer years ago meanwhile waging war on the millions of cockroaches in his Echo Park apartment. Trussell's "poor decision to be a pseudo-charlatan web designer" mixed with the fumes of roach-killing bug spray assures Trussell he will be reincarnated into a cockroach in the next life. 

Some more gems:

It makes you seem dangerous to have a low-grade website, it makes you seem like you’re up to no good. It probably gets you on a thousand NSA watchlists.
You can ruin your life with a bad website.
You don’t want some awful website hanging out there like some kind of scrotal mistake on the digital sea.

The Ugly?

Much like his own podcast, Duncan Trussell takes you on a rollercoaster ride of emotion. Shortly after going downhill from making a bad website to a nightmarish raid on your home and family by "jack-booted thugs", Trussell offers the only thing worthy of saving you from such torture: Squarespace.