This is part of our 100 Creative Directors interview series. It has been edited for length and clarity. To return to the series homepage and browse other interviews, click here.

How did you become a creative director and what does the role mean to you?

My path has been anything but linear. I started out in the music business — initially, I wasn’t even aware you could be a professional creative without being a musician or performer of some sort. So I spent a number of years playing in rock bands, managing small artists, and running my own small recording and production studio.

Through all my endeavors in the music world, I found my way into graphic design. Obviously a key component of that business is marketing events, building essentially lifestyle apparel brands around the artists, and just creating all types of media. I was making flyers, posters, and T-shirts. I was marketing bands on MySpace, thinking about interesting ways to present artists via social platforms and YouTube. Through all of that, I fell in love with the craft of visual design and ended up meandering my way through the industry over the years.

Most recently, I’m running my own small studio, Winterton, and I’m on contract as a creative with Wieden+Kennedy. It’s an agency I’ve looked up to forever and it was actually a big reason I moved to Portland in the first place, so I’m very grateful for the opportunity.

Are there advantages to coming into this industry non-traditionally, as opposed to through a typical design or other ad school-type program?

That’s one thing I’ve often heard from partners, other creatives, and clients — that I bring a unique perspective to the work. Because I didn’t go through a design program, I learned things the “wrong” way, just looking at the people around me and figuring it out on my own. I’ve always had an ethos of, how much can I get done as a one-man band, just being scrappy? Even as I’ve grown to manage and be part of larger teams, I’m driven by that same philosophy.

One thing specific to the Portland area is you’ll see a lot of junior creatives coming out of school with similarities in their portfolios. That’s not a bad thing — we’ve got PNCA and the PSU design program, two phenomenal, deservedly well-respected institutions. Initially, though, all these students are swimming in the same pool and picking up similar influences, so their student work sometimes has thematic and substantive overlap. Very quickly, they start to blossom and develop into their already evident, unique styles, of course. But I think for me, earlier on, not coming out of that type of environment helped me stand out.

I always had these backwards ways of working with the different Adobe tools, which was, to be honest, sometimes a hindrance. At best, though, learning things the “wrong” way let me produce so many interesting, unique results.

You’ve worked in sales and founded your own company multiple times — how has your diverse career background contributed to your practice as a creative director?

It’s absolutely benefitted me. I have a background in sales and business development. Early on in my career, in those startup, learn-on-the-job, six-different-roles-at-once environments, I had to learn many things very quickly. Again, it’s that one-man-band ethos.

What those early years gave to my work today is a real comfort interacting with both the clients and the more business-oriented stakeholders inside all the organizations I’ve worked at. I’m fluent in the language of KPIs and business goals, especially having founded my own boutique agencies. I can walk the line between creative craft and business acumen, which I think defines the creative director role as different from a pure creative role.

You’ve founded your own business three separate times — why do you keep coming back to that?

Because I’m stubborn. When I was in my very early 20s, I was working for an entrepreneur who was a great, inspiring mentor for me. He showed me the opportunities that exist when you make your own way in the world. Honestly, I’ve tried and failed and tried and failed on and off ever since. It’s not easy.

My first business model, I raised a small amount of capital and brought in a technical co-founder. We were going to do a SaaS business, but quickly realized how difficult it truly was. So we switched it up and started landing clients as a service-based business, doing web development and custom code projects. It didn’t work out, so I went back to the day job world. But I’ve always found my way back. 

At one point I went all-in on music, like I started to talk about earlier — running a small studio, managing artists, building my own music career. That was probably more difficult than any of the other, more traditional business endeavors I’ve embarked on.

I’ve kept returning to traditional employment because it offers a level of safety. It’s swimming back to the shore. The ceiling is so much higher when you’re out there on your own, building something for yourself, but the flip side is there’s no safety net. It’s up to you — if you fail, hopefully you have some savings.

After all these experiments, things finally started to click in 2021. I reformed my LLC and started my own agency, Winterton. I’ve been building it up since then into a three-pronged business model — three distinct revenue streams to help mitigate risk. I do creative services for businesses, I plug into larger agencies as a creative, and I have a media business. Across LinkedIn, TikTok, and Instagram, I’ve built an audience just shy of 200,000 for my design and creativity content. I’ve been doing sponsored content and it’s also a lead funnel in and of itself. 

What’s the importance of personal side projects — like your newsletter — to your ability to do your day job?

It’s important to be able to create without boundaries, without rules, and without the expectation of a certain outcome. I’ve been asked, in interviews and settings like that, what I would do if suddenly got rich and didn’t have to work, or where I would be if my career suddenly progressed five years into the future. The answer I keep coming back to is that I’d just be doing the same thing. It might take different forms, but I just love creating, making something out of nothing. Music, graphics, videos, just turning ideas into things is amazing.

There’s a certain level of basic creative freedom you have when you’re creating for yourself, but there’s also this unlock that can happen when you’re creating out of a sense of play, with no timelines, budgets, or other pressures. You know there’s not going to be any client to please, any revisions some other party has to make. Of course, having another person — a creative director or a client — involved, pushing different angles on the work, can also make work better. There’s pros and cons. But I do find working on my own projects helps fill the well I draw from in my day job.

What are three things that are crucial to your work?

The first is, no surprise, the Adobe Creative Cloud. I’m a huge fan of the suite and they’ve been a phenomenal partner to my agency and media business as well. Shout out Adobe, there’s a great team of human beings behind that software.

Second is my iPad or just pen and paper. The tactile nature of both is wonderful — just scribbling down an idea or sketching a layout feels so different than using a mouse in these more complex software tools. It unlocks different thinking, like if a guitar player sits down at the drums — they’re not playing how you’re supposed to, but they might come up with some incredible beat the drummer would’ve never thought to play.

The last one is design inspiration sources. Both online — I know you had Jacobi Mehringer, the guy behind Eyecandy, on here a while back — and physical books and design pieces. I’m constantly buying design books. I’ve been building up this incredible catalog of graphics, logos, design thinking texts, tactile things that I can pull from again and again.

What's a piece of advice somebody has given you that’s really stuck with you and been foundational to the way you do this work?

There are two things. The first is to approach every brief and every project as a chance to do the best work of your career. The first time someone told me this, I thought it was so cheesy and hyperbolic, but now it’s something I say all the time, whether I’m working with a team or leading a creative team. It’s not always truly a possibility, but there’s something wonderful about approaching the work that way. Some folks in the agency world will say, “hey, we work for our portfolios, we don’t do it for the agency.” There’s some truth in that — you do need to build a great portfolio — but with that in mind, let’s create the best work of our lives for our portfolio, for the agency, and for the client.

The second thing is more on the business side. There are three inevitabilities in life: birds fly, fish swim, and deals fall through. That’s saved me from heartbreak plenty of times. Maybe I’m starting this project that seems certain to turn into a big, ongoing, monthly deal for my agency and two weeks later it falls apart. Sure, it sucks, but you find another one — this is just how it goes.