Art is what you can get away with. – Andy Warhol

Warhol’s words have always struck a chord with me, especially in the world of marketing and brand building. I’ve spent years crafting campaigns that aren’t just creative but daring—strategies that toe the line and stick with people, sometimes in surprising ways. Warhol’s quote, at its core, is about the art of pushing boundaries. It’s about taking calculated risks to create something memorable that makes people stop and pay attention. But, like all art, it’s about knowing the right line to push.

There’s an art to “getting away with it” in marketing and advertising. Done right, a campaign can be unforgettable. Done wrong, it can fall apart and become infamous for all the wrong reasons.

Take Tony Hinchcliffe as an example for you. Recently, he took a risk by making a series of racist jokes at a Trump rally. He may have thought it was edgy humor, but it crossed a line that alienated and angered his audience. Instead of sparking engagement or introspection, it led to backlash. This is the same delicate balance we face in marketing. The goal is to be bold enough to stand out but thoughtful enough to keep people on our side.

Here are a few of my favorite “stunts” that illustrate this balance—ideas that might have seemed over the top at first but were executed with an understanding of the audience and the brand:

??? A Real Cloud for a Cloud-Based Product: We were the first to use "real clouds" to promote a cloud-based software brand. Using skywriting planes over the San Francisco Bay Area, we put our message in the sky. This was a one-of-a-kind moment that resonated because it wasn’t just about grabbing attention—it fit the brand’s identity perfectly. People connected with the metaphor, and it became a memorable experience.

?? A Carnival at the California Capitol (Without Permission): For a campaign where we needed to get legislators’ attention, we set up a full carnival right on the steps of the California State Capital Building. Picture food trucks, clowns, popcorn stands, carnival games—the works. It was a huge spectacle, and yes, we ruffled a few feathers; I got detained by State Police and had to talk my way out of it, but it got our message across and brought the brand front and center. This was an example of going big but staying relevant and intentional.

?? Hosting 1,000 Tupperware-Style Parties for Invoicing Software: This might sound wild, but we organized 1,000 volunteers to host Tupperware-style parties in their homes to introduce people to an invoicing software brand. This created a personal, face-to-face connection that no billboard or ad could replicate. It wasn’t just marketing; it was about real engagement, taking a risk that helped turn a software product into something people could relate to and remember.

These aren’t your run-of-the-mill campaigns, and they weren’t without risk. Each had the potential to be polarizing or misunderstood. But with every bold campaign, the goal is to understand where the edge lies and how to stay on the right side of it.

For anyone building a brand or planning a campaign, consider Warhol’s words: Art is what you can get away with. It’s not just about being loud or flashy; it’s about understanding your audience deeply enough to know how far you can push. The best campaigns live in that space between bold and reckless, making an impact without stepping over the line.

What’s a campaign or brand moment that made you stop and think recently?

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