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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How many of us have heard that inner voice, and ignored it? Or perhaps even more daunting—heard it, and took action?

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I’ve been waiting to reveal this conversation with my friend, and meditation teacher, James Brown (LinkedIn) until spring begins to sprung. Sure, it snowed a few days ago here in Minneapolis, but today it’s going to be 60 degrees out. The time is ripe. For me, the spring season conjures moments of surprise and change in our lives. For months now, the ground has been frozen. Suddenly, a memory, a seed or an insight pops out and suggests a new course of action.

That’s kind of what transpired for James as he made a pivot from decades playing the role of advertising copywriter and creative director—worshiping the trends and cultures of an industry—to hearing a voice, and slowly turning towards a different path.

“I think that inner navigational beacon, that voice, that whatever we want to call it is present in all people. But we get really good at drowning it out or ignoring it or talking ourselves out of it.” - James Brown

James and I first met in St. Louis, MO working as copywriters for the TBWA Switzer Wolfe agency in that era just before the Internet arrived. And then I witnessed his journey and transformation from afar. We often spoke over the decades about the business of creativity, the nuance of process, people, and agency culture.

In this interview James helps illuminate a constant challenge for all of us, especially those who create new ideas where none existed. This is the struggle to receive and adapt to criticism—to dance the delicate choreography of relationships, politics and the unknown. To balance our need for success with an addiction to certainty.

“There is obviously, like a very understandable and instinctive clutching to what we want to have happen... And in the process of saving [an idea], you kill it, right? And you create something that no one is proud of. It doesn’t work.” - James Brown

A solution, James suggests, is to recognize there are always more and potentially better ideas; and to find a graceful way to remain faithful to those ideas in which you truly believe. There are no easy answers, there is only the practice of doing it, over and over.

“Creativity is mysterious. It’s sort of like the difference between spirituality and religion. Religion is rules... spirituality is finding out for yourself what’s true. So spirituality embraces the mystery, creativity embraces the mystery.” - James Brown

We cover a lot of ground in the hour or so of our two-part conversation. As the intro suggests, this episode took place in two sections, separated by an unsuccessful but suggestive tsunami. For me, this conversation gives permission to think broadly about how any of us creates, where we find and nurture our creativity, and how we can prepare and protect ourselves to receive more inspiration. Are we dry tinder, or are we damp moss?

“Spark is a good way of thinking about [inspiration]. Because if a spark falls on dry tinder, it will start a fire. If it falls on damp moss, nothing happens.” - James Brown

Along the path, we discuss a familiar favorite of mine—the three forces of Vedic philosophy: Creativity, Maintenance and Destruction. And James suggests an intriguing way of thinking about AI as it relates to creativity, art and human history.

Thanks for coming along.

🤔 One thing you might notice about this podcast, and my Substack newsletter, is that I’m not asking for money. The newsletter, and these conversations, they’re all free to you.

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Episode Notes

🎶 James has been listening to “Fix It” by Lady Blackbird (YouTube, Spotify), and he references Bill Evans’ classic “Peace Piece” (YouTube, Spotify). And I mention a Robert Glasper quote about jazz being the mother of hip hop.

James’ weekly newsletter, Monday Meditations, is available here.

You can learn about his approach to teaching meditation here.

And his online meditation curriculum, called Flow, is available here which includes frequent online group meditation options.

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Just imagine if he’d stuck with selling bonds.

Very few of us wake up convinced we need to be a creative person, and then stick with it. No, some of us venture off into corporate finance for a bit first.

But then creativity comes calling.

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When I first met Dave Weist (website, LinkedIn) I was convinced he was older, wiser and earned a lot more money than I did. Some of these things might have been true. Today he’s Hill Holliday’s Chief Creative Officer, so I know most of them definitely are true.

Dave understands humans, especially creative ones, and has a keen sense of how they function and how to organize them effectively. His focus is on the power of individuality.

“I need your brain here. Like I really want you here. Call it a little axiom, but great minds don’t all think alike. So I need you to pressure test this with me. I need us to disagree a little bit.” - Dave Weist

It’s hard won, valuable trait. And I’m thrilled he made time to talk about what he knows.

[Like they say] “Be yourself because everyone else is taken. I’m definitely always preaching that in a creative department. And you have to remind yourself sometimes too, you know, that that’s ultimately what it is. Because the ultimate goal is, I need that—I need your fingerprints on the work for it to really connect.” - Dave Weist

We covered the waterfront, from how to sell audacious ideas, to the three (very different) roles of the Executive Creative Director.

“When you become an executive creative director, you have to acknowledge when you go into a room which role you’re playing. Are you the executive where you observe things from a 30,000-foot view, the creative digging around for solutions with the team, or the director working to bring a creative vision to life?” - Dave Weist

There’s lots of useful, inspiring insights in this episode. I hope you enjoy it.

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The stereotypical advertising writer always has a novel on the side, always unfinished. The advertising writer Jane Roper (website, LinkedIn) has already published two novels, and her third is underway.

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I first met Jane at the Partners & Simons agency in Boston. Then we collaborated on the VW advertising business at Arnold. In this conversation we discussed the importance of briefing (as useful for marketing as to inspire fiction).

“I want a creative brief that isn’t just a dumping ground of information. I want to know why [the audience] wouldn’t choose this product or offering—what are the objections that we need to overcome?” - Jane Roper

And we addressed the challenge of writing novels, the commitment to muscling out the words every single day, despite the challenge of work and family. Jane finds her time in the mornings, before the day overwhelms. She’s not enamored with or driven by a muse. She just puts in the work. All while recognizing the perils of consumption, the ever-present smartphone.

“I think it’s so important [not to] fill every down moment looking at our phones. Because then I’m not leaving space for the ideas to come in. You’ve got a daydream, you’ve got to be bored. Maybe that’s why the shower moments and walking ideas come—they happen because I’m not filling every second with something. I’m leaving space for ideas to come in.” - Jane Roper

Let’s be honest, Jane’s not a huge fan of AI. We talk at length about ethics, creator rights, and job replacement. Where AI does intrigue her is when it can unlock new approaches to creativity.

“I find it exciting [when AI is] bringing in a new capability rather than trying to replace something human... when it’s trying to replace human activity, then I find AI depressing.” - Jane Roper

Rooted in Jane’s work—from advertising to novel writing—is a keen sense of balance, where writer and audience find room for each other, and the magic happens.

Episode Notes

Jane’s watching season 3 of Somebody Somewhere.

Jane mentions short story writer Frank Conroy at the Iowa Writers Workshop.

And the advertising writer Kara Goodrich.

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When you’re trying to navigate tumultuous change, it helps to have inquisitive navigators. As I’ve tried to make sense of AI, I’ve found useful explanations and pragmatic advice in the work of Noah Brier.

FYI—he’s hosting a Los Angeles version of the BrXnd AI Conference on February 6, 2025.

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In this opening salvo of 2025, we hear from Noah as he walks us through his journey graduating from NYU into an initial career in journalism, then a pivot into the early 2000s era of NYC Internet-adjacent firms (Renegade, Naked Communications, The Barbarian Group) before co-founding Percolate in 2011.

“My whole life has been an openness to following those strange gut feelings when things don’t add up or you can’t figure something out and just going down the rabbit hole.” Everything I’ve done - it’s been one rabbit hole after another.” - Noah Brier

Of course we talked about AI. And I really appreciated his ability to frame the change we’re experiencing, as we shift from what Noah calls a Deterministic view of computing into a Probabilistic one. “We can’t underestimate how weird this shift is,” says Noah.

“What makes AI different is that we have always existed in a world where computers were deterministic machines. Fundamentally, we have a lot of intuition built up for what it means to use a computer that is a deterministic device. We’re used to these paradigms of deterministic computing. And one day we wake up and there’s this thing which just flips it all on its head.” - Noah Brier

And so here we are with a profoundly new way of computing, of thinking about computing, of building teams, cultures and process around computing—and the underlying concept is now very, very different. No wonder this stuff takes time to settle, to become real for the masses.

We cover a lot of territory, from creative briefs and AI-empowered brand style guides, to the purpose of marketing to what defines great creatives. But woven through it all is a sense of the profound change we’re encountering together.

“Nobody has thought about what it means when intelligence is essentially unmetered, and when it is instant. Instant intelligence is going to be a very mind-blowing thing.” - Noah Brier

Lots to chew on here.

I hope you enjoy it!

Episode notes

Noah mentioned studying the XYZ Affair during Middle School winter break.

And being a student at the Bank Street Elementary school.

And talking about the bike that proves you actually turn left (just a little) before you turn right, and vice versa.

Noah recently co-founded Alephic, an “AI-first technology foundry.”

And here’s a recap of Noah’s favorite piece of writing, from the designer Michael Bierut.

And finally, a hearty welcome to 2025. I’ve got at least three more podcasts in the works for January and early February, and I’ll return to weekly writing next week. I hope you have been thriving.

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I first met Paisley in Boston back in the early 2000s when she was a writer on the Volkswagen business at Arnold Worldwide. This was the early Internet, the era of storytelling through banner ads. We were transforming the idea of advertising for a digital age. Since then she’s moved back to San Francisco, her birthplace, and made a career in strategy, branding and naming. And joy.

“People can feel it on the other end. If you have joy, if you have passion in your work, if you fall in love with your project, they feel it and they can fall in love with it, too.” - Paisley Schade

In our conversation, Paisley provides a wise distinction between the efforts of advertising and the effort of branding. They’re too often considered the same. For Paisley, there’s the issue of time.

“I think it’s about the view—how far ahead you’re looking. With advertising and social media especially, if there’s something hot, you need to address it immediately, like within hours. You need to be aware of where culture is going. [Brand is different.] You’re trying to create something that’s going to last at least ten years. So you have to look out like what’s the deeper or farther perspective? Trying to predict how society will feel ten years from now is hard to do.” - Paisley Schade

And then there’s the difference in output. What is meant to be seen, versus what has meaning but isn’t always visualized or published.

“The thing about advertising is you see your work in the world. With branding, I may have done the whole strategy behind the company, the voice and the messaging—but I won’t see my words in the world.” - Paisley Schade

We spoke at length about AI. As a writer, she’s very resistant to giving up the responsibility of her words to an algorithm. And she’s amused when AI companies hire her to help define and advertise their AI platforms. But she offers a poignant insight about taking notes in a meeting, and listening.

“I was talking to somebody and they were like, ‘Oh, I use AI to take notes in a meeting.’ And I said, why would you do that? My notes don’t look like the minutes of the meeting. I don’t write down what people say. I write down what I experience. I’m reading their facial expressions and watching them. And those are not the same thing. An AI is just going to spit out what it heard. And that’s not good enough for me.” - Paisley Schade

We had a robust, wide-ranging conversation. I hope you enjoy it.

Thanks for reading and listening. This is the final podcast episode of 2024. I’ve got edits in the works and interviews lined up for a slew of intriguing interviews starting in January. Please help me build the audience and share this episode with one other person.

Episode notes

Paisley mentions the song Wriggle by the artist Cosmo Sheldrake.

You can find Paisley on her website, or via LinkedIn.

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I think she might be the future of advertising.

Ashley Rutstein (LinkedIn, Website) showed up in my TikTok algorithm a few years ago with consistent, thoughtful, and wise insights about the business of creativity and practice of advertising. She’s turned StuffAboutAdvertising into a wonderful resource for current campaign reactions, brand strategy perspectives, career advice, and creative briefing techniques in this chaotic age. Her output is impressive. 111k followers seem to agree.

“I love dissecting creative. I also really want to educate.” - Ashley Rutstein

In this interview we talk about how Ashley developed her voice as a writer, the challenge of unearthing useful strategic and creative insights, and of course, the influx of AI and the impact of platforms like TikTok. As Ash puts it, “I always encourage [people] to just try whatever new thing has popped up.” Fluency in whatever’s new matters—it gives you credibility.

“You don’t get to say yes or no if you don’t know what this platform is about.” - Ashley Rutstein

Never mind the IPG/Omnicom merger. What’s really transforming the role and evolution of advertising in the world of business and culture are creators like Ashley leveraging the latest technology. Make no mistake—she’s coming from a place of deep respect for the history of the industry’s craft. She embodies Bernbach’s Paradigm. Ashley’s grounded in the nuances and art of strategic techniques. But she also grew up making lots of YouTube videos because she could. She’s lived completely and successfully in a realm minus the traditional gatekeepers. She’s teaching us how to operate in a world that’s dismantling the status quo. And I admire her for wanting to evangelize her experience and reality to the next generation.

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I met Liz Vanzura because of the drums.

Long story short, I was playing in a Boston band circa 1997, when I met a guitarist named Lance Jensen. Turns out Lance was, like me, an advertising copywriter. And he was co-creative directing the relatively new VW account at an agency called Arnold. Maybe I could help him write copy for a showroom brochure for the soon-to-be launching New Beetle?

The business of creativity is a business of luck, of timing, and ultimately, of human connection. I was incredibly fortunate to land within the art directors, producers, account execs, designers, fellow writers, and client team on VW at that point in time—right as the Internet was becoming “real,” right as the brand itself was become “one of the most successful marketing campaigns ever,” according to Adweek.

Our main client for most of my nine years on VW was Liz Vanzura (LinkedIn). A self-described “Detroit car girl,” Liz grew up around engineers amidst the sprawling General Motors family. She cut her teeth in audience insights and brand strategy. And her career includes remarkable work leading branding for Volkswagen, Hummer, and Cadillac. In our conversation, Liz illuminates how she and her team, and ours at the agency, found common purpose to both instigate and evaluate effective work. “The discipline to measure work against a brand’s essence is what makes campaigns successful,” says Liz.

One of my favorite aspects of working on VW was the desire from our marketing clients for risk-taking; especially as brands were discovering the Internet.

“The bravest marketers aren’t afraid to fail; they pilot, learn, and adapt. The fear of getting it wrong often leads to missing opportunities.” - Liz Vanzura

Liz and I discuss a few marketing firsts—VW was the first OEM to sell cars online, the first to launch an Internet radio station, and the first to tout online films (and yes, BMW invested a lot more than we did).

Of course we talked about the future, about AI, and the impact of technology on ways brands understand and engage with their audiences. Liz is deeply engaged in AI, co-founding GAI Insights, hosting global conferences on AI, and gearing up to teach an AI marketing curriculum at Bentley University.

“If your organization isn’t calendaring time for learning AI tools or attending training, you’re already falling behind.” - Liz Vanzura

We cover a lot of ground in the interview, including automotive brand and retail marketing, audience insights, brand building process, and team leadership amidst cultural and technological change.

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Are you, as Brian Eno offers, an architect or a gardener? Do you need ideas meticulously dictated or might you be willing to curate and see where they grow?

It’s hard to imagine a better metaphor for my conversation with Rafa Jiménez, founder of the AI creativity and innovation platform Seenapse. This is the second iteration of the Curiosity+Courage interview series, and we cover a lot of territory.

Rafa tells the story of a childhood focused on making culture versus merely consuming it, discovering how an audience reacts to your ideas, and how to learn from their perspectives. This is the difficult, yet critical development of a successful creative mindset.

Then we venture into the heady days of the late 1990s as technology and advertising become strange bedfellows, and Rafa’s company is acquired by WPP and he finds himself discovering the world of advertising and characters like Neil French. In that period, Rafa witnesses a computer win at the game Go, and has his epiphany—the notion of a computer generating useful, fresh ideas alongside humans. Seenapse is born.

But the journey is long, winding, and never obvious. Product Market Fit proves illusive until the current generation of AI begins to emerge, and Seenapse is reimagined.

Ultimately, we discover idea people need to be in constant dialogue with their tools, to see where they might take us.

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Sometimes you just have to talk it out.

Welcome to something new.

I want to engage in longer format conversations with creative people within this newsletter—I want to illuminate how artists and idea people think about their process and work, and how they’re navigating AI. But where to begin?

Hard to imagine anyone better than a former band and room mate.

Peter DuCharme and I met in a Boston recording studio around 1995. I was at National Studios on assignment, producing audio for a client of agency Heater/Easdon. Turned out the engineer, Ken Michaels, played bass in a band. And the lead singer / guitarist just happened to swing by. And wouldn’t you know it, their band didn’t have a drummer. The marvelous Evelyn Pope joined us on keyboards and vocals soon after.

The New Prime Numbers played around Boston and Cambridge in that wonderful era just before the smoking ban took effect. Many fond memories of gigs at T.T. the Bear’s Place, The Middle East, the Lizard Lounge, the Paradise.

Peter, and my first wife and I shared a second floor apartment on Beacon Street, not far from Cleveland Circle in Brookline around 1998—the same year Volkswagen debuted the New Beetle. Mine was yellow, which I parked out front until someone knocked off the driver’s side rearview mirror.

For several years Peter and I got to collaborate on all kinds of diverse music and technology projects at Arnold Worldwide as Volkswagen first engaged in the Internet. Peter composed and produced this infamous music track. And he helped us imagine RadioVW, a branded Internet radio station born years before platforms like Spotify existed.

For this inaugural chat, Peter and I talked about the responsibility of creating, the role of technology in art, those “lawsuit-infused” text-to-music platforms and where AI might be headed. Alas, we did not discuss Fuzzy Slippers.

Peter currently serves as Senior Music Automation Engineer at Boomy, where he helped develop LoopMagic, the AI beat and sample creation platform predicated on, and with the collaboration with producer and songwriter Illmind.

Listen via the podcast above (subscribe via Apple and Spotify), or watch our conversation below.

🤖🎶 Worth noting: In a related interview, Semafor’s Reed Albergotti writes, “Will.i.am has been playing with AI models like instruments, experimenting with how to get them to behave the way he wants.” The artist believes the evolution of music via AI is still very formative, “We’re at Pacman and we haven’t even gotten to Halo yet.”

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