What if the only way you got to eat was by making art and design people believed in? And from that starting point, imagine becoming arguably one of the most influential humans in global creativity.

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I first met Kevin Swanepoel (LinkedIn) in May 2000. That evening, I had no idea how he’d arrived in New York or birthed One Show Interactive. All I knew was, he was handing me a two-and-a-half pound, gold-colored trophy, and it had the words “Best of Show” inscribed next to my name.

That small moment had a tremendous impact on my career. And it wouldn’t have happened if Kevin hadn’t put food on the table by airbrushing surfboards in Durban, South Africa.

As CEO and President of The One Club for Creativity, Kevin now leads an organization which has been educating and provoking the industry of ideas and their craft for over 50 years. In 2025, its dominant competition, the One Show, received almost 19,000 global entries spanning disciplines including Film & Video, Design, PR, Experiential & Immersive, Social Media, Interactive, Creative Effectiveness, and now Creative Use of AI.

This is the story of Kevin’s journey from an artist making rent with his art, to becoming a design agency owner, to being one of the first people to leverage, then sell Apple computers to fellow creatives across the sub-Sahara, and through coding skill, to wind up transforming the legendary One Club for Art and Copy.

Primarily Kevin’s is a story of curiosity, and a daring to try and build what’s next.

“If you are not an inquisitive person who’s constantly learning, you’re just going backwards.” - Kevin Swanepoel

We talk about the business of creativity, creative competitions, and the value found in evaluation. I recall my first portfolio being shaped entirely by days spent analyzing the 1988-91 One Show advertising annuals. In these heavy, glossy collections I was coached to take ten Post-It Notes and “judge the judging.” Which ideas were my favorites, and why was that? What could I discern from those ten ideas which might help me make “the 11th ad?”

“The great (creativity) judge is somebody who’s sympathetic with the work, who looks for the good in it.” - Kevin Swanepoel

Today, the One Club is embracing and cultivating an incredible diversity of talent and technique. The organization is deeply invested in sparking the careers of people who mirror Kevin’s history—helping them find likeminds and opportunities for success.

They’re also embracing AI. Both the One Show and the Art Directors Club competitions have welcomed AI-infused creativity. As we were talking, Kevin shared insights from a recent round of creative judging for AI-informed work. Judges sought out ideas which were only possible because of AI.

“You’ve got to partner with [AI]… and hang with it. Don’t be seduced by the tool—judge the idea. But test what’s possible.” - Kevin Swanepoel

After we finished talking, I looked through my bookcase. And there it was. Volume 1 of the One Show Interactive — Kevin’s idea which, one could argue, entirely transformed how the ad industry thought about, embraced, and evolved its definition of creativity. The work inside is dated, of course. But that first effort laid a foundation which prevails today.

Thanks for having the guts to make that happen, Kevin.

Episode Notes

The One Club for Creativity website

Creative Week is May 12-16, 2025 in New York City, including events for the Art Director’s Club awards, Type Director’s Club awards, One Show awards ceremony, and Young Ones.

And they’re doing incredible work guiding the next generation of creative talent, including the One Creator Lab, now in its fifth cohort, training creativity for a world fueled by TikTok (note previous Creativity+Courage guest Ashley Rutstein has been an instructor).

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