Taking Bold Risks: "I'm fortunate to work at a company where we really value taking risks," Rubin says. "We’ve used organic and content campaigns over the last three years to really build our brand. We know that a great story can reach a lot of people, and we also know that, as many marketers know, having a good enemy often makes a more compelling story or at least something more fun for people to engage with."

Air positions itself as creating the first creative operations system for creative teams and marketers, directly challenging established players like Dropbox and Google Drive. The impetus for one of their boldest campaigns, Drop that Box featuring OnlyFans star Bonnie Blue, aims to help keep creative teams from "getting screwed". 

"There's an old way of working in files that tools like Dropbox and Google Drive use," Rubin asserts. "These are tools that were built for file management 15 years ago and haven't really been updated for the way that creative teams operate today—decentralized, often remote, and frankly creating a lot more content than we ever probably could have imagined."

Criticism welcomed: After taking the risk and putting their idea out there, the campaign has gone on to be Air’s most successful to date, generating an unprecedented amount of website visits, social media interaction, engagement, and media coverage.

With so much conversation generated, polarized responses naturally come up. In Rubin’s eyes this isn’t something to fear, rather, it should be welcomed: "I love hearing people say 'I hated it and this is why' and I love people defending it like, 'This is brilliant. Here's why.' I don't think there's a right answer here. The people that hate it are totally legit and totally valid in hating it. It's really not for everyone. But we're trying to spark conversation with creativity. So that to me is the metric of success."

Executive buy-in: When asked about securing executive support for creative campaigns, Rubin is uncompromising: "I would not waste six months of my life trying to build stakeholder trust through small campaigns and experimentation. The answer would be, I would quit."

He emphasizes that playing it safe leads nowhere. "If you're in your little gated castle and you're like, 'It's cool, I'm just doing these LinkedIn posts once a week about product'—again, that's fine, but you're not going to win and you're not going to build a brand that stands the test of time."