My Creative Career: Sam Shepherd, chief creative officer at Uncommon NYC

Throughout his school and college years, there were two distinct sides to Shepherd that he felt were conflicting. On one hand, he was brilliant at art, on the other, he was a good athlete. These didn’t often work together, the discipline that sport requires regularly conflicting with the free nature of being creative. In a locker room filled with burly footballers and business majors, he felt like somewhat of an outcast as the guy who took painting classes on the side.

“I’m a Gemini, so it kind of fits the two sides of me,” he laughs. “I loved painting, sculpture and drawing. Weirdly, sports and art got me into a really good school and I just kept doing both. I always wanted to make money with just pure fine arts, but I think every creative person comes to that fork in the road.”

He recalls being made fun of by his teammates, but that period taught him a lot about the business side of art; he knew there had to be a crossover, otherwise he might have been destined to become, in his words, a full-on hermit in an art studio.

His parents questioned how he would ever make any money pursuing art, but a stern conversation with his teacher made an impact. “She sat me down one day and gave me what was the best talk I’ve ever had because it told me I needed to stop taking such a middle ground and either go one way or the other.”

He googled portfolio classes and came across Miami Ad School. After landing a place at the prestigious institution, Shepherd grabbed every opportunity that came his way (including the party scene in Miami Beach, which he jokes probably took 10 years off his life in the space of 12 months). His first taste of agency life came with an art direction internship at Saatchi & Saatchi in Moscow, Russia, that was supposed to last four months.

“On the last day, they threw me a big going away party and I brought all my things because my flight home was the next day. I had all my stuff in the basement of the agency and someone broke in and stole everything I owned – my visa, my passport, my computer with all my work on it, everything. So, I spent another three months just trying to get out of the country. I can look back on that now and laugh, but at the time it was pretty wild.”

Once he finally was able to leave the country, his next move was to Ogilvy Sao Paulo in Brazil, which was equally as full on. It was right at the time when Anselmo Ramos and his team were doing Dove’s ‘Real Beauty Sketches,’ right before they blew up. “It was great that they were all doing that, but I was the only intern and I was American. It was my first real taste of work ethic and getting my ass kicked,” he recalls. “That was one of the best things that happened to me because it just showed that, if I wanted to really be great at this, I have to change, I have to work harder, my ideas have to get better. It was a real eye-opening experience.”

Back in New York after the three-month stint, he used this drive to get his foot in the door at Mother. What started as a one-day freelance gig kept getting extended, even if he wasn’t quite working on the big briefs he would have liked.

“It’s funny because they would only give me web banners to design, but I would treat those web banners so seriously,” he laughs. “I’d bring them the banner that they wanted but then I’d also these crazy ideas. Half the creative directors were rolling their eyes and the others were like, ’OK, he means well.’”

For a while, banners followed Shepherd. At his next job, at DDB New York, they were for the insurance company State Farm and while he can laugh about it now as he looks back, he admits to having “a bit of an ‘oh shit’ moment“ and realizing he definitely didn’t want to be stuck doing them for the rest of his life. “I could still tell you to this day the hex value for the color of State Farm red. I had bosses who were brutal about my web banners. They would schedule what they would call ‘postmortem meetings’ about them.”

Shepherd recalls how they would point out if there was even one pixel out in his design. It was a frustrating time but one that informed every next step he made. “I had gotten a glimpse into a certain future that I did not like. It really lit a fire under my ass to not do that ever again.”

After three years at the storied Madison Avenue agency, he would go on to cut his teeth at Deutsch, KBS and 360i before landing the role of executive creative director at Leo Burnett back in his hometown. While there, one brief required him to really put his work on the line. It was for Change the Ref and meant taking on the NRA. It will always have a special place in Shepherd’s career because of the risk involved in making it.

But it’s a film he made early on in his career, ‘Four Year Old’s Bucket List’ for Water Is Life, that he is most proud of. It’s about a little boy who lives out his wildest dreams for a day and makes a point that children in Sub-Saharan Africa often don’t live past the age of five. What started as an idea jotted down on paper quickly resulted in a 10-day shoot.

“That gave me so much confidence, just from a purely creative, maker mentality. If you like something enough, you can go make it happen. Early on, that informed my mentality, which is I never want to hear a ’no.’ There’s always a way and I think that, by carrying on that level of bullishness and positivity, anything is possible.”

After more than three years at the agency he first heard of as a 15-year-old, Shepherd made headlines when it was announced he would become the chief creative officer at Uncommon’s new NYC arm. The people and the ethos are what drew him to the agency, he says.

“I had to be really critical of myself, about my body of work and what I haven’t done, as well as where I want to go. Part of that, as best as I can sum it up, is that I don’t want to just keep making good ads. I think that sometimes, as an industry, we undervalue creativity in general.

“So this next step for me was about raising my own bar infinitely higher and the agency that truly matches that is Uncommon. The second I spoke to [Uncommon founders] Nils [Leonard], Natalie [Graeme] and Lucy [Jameson], it was like kindred spirits in terms of their benchmark. They’re playing by a different set of rules.

“They love the challenge and they love adversity; they love just proving people wrong. That fits every single thing that I also stand for. So, I’m just really, really lucky that I met them when I did.”

On what he plans to bring to the new office, Shepherd says the task is to keep Uncommon Uncommon, but give New York its own ‘thing.’ Instead of focusing on advertising outcomes, it’s about real-world outcomes and getting the work spoken about within the culture.

“One of my favorite people is Rick Rubin. And when he says just because you haven’t done something yet doesn’t mean you can’t do it, it just means you haven’t thought of it yet, I think the second you say that to yourself, you have to be your own cheerleader and just work hard.”

Like this story? Read out interview with Nils Leonard about his life and career.