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 end up becoming a creative director?

I grew up in Phoenix, Arizona. During the summers in high school, I started working construction with my brother-in-law, digging ditches. After I graduated, I kept doing it all summer. I remember that August, sitting in the shade on a Friday afternoon, drinking Gatorade, beating the 120-degree heat, and my brother-in-law, who I was working for, looks over to me. Real quiet type. He says, “This sucks, huh?”

I say, “Yeah, this sucks.”

He tells me: “So, you’re fired. You need to go to college. This is your last day. Go sign up for community college.” And I did. Of course, I kept working in the service industry for years, because I needed to survive. But that guy firing me, pushing me that day, got me on this path.

I really came into this career through the back door. I was always a misfit.

You “came into creative through the back door” — how so?

I went to community college and studied philosophy. I was really interested in the language aspect of it all — I’d written poems and played in a bunch of hardcore bands, I was interested in writing. One thing I didn’t understand at the time was that growing up poor really forces you to be creative. You have to figure things out for yourself. So I’d been booking my own tours for the bands I played in, putting on events, and I applied that to poetry. I started my own journals, my own press, my own reading series.

I pivoted to studying poetry after getting an undergrad in philosophy and did a second undergrad in poetry. I wanted to get an MFA, be a college professor and just write poems, talk about ideas, just be around those sorts of folks. So that's exactly what I did: I went to graduate school, got an MFA in poetry, and started teaching. 

I was an adjunct professor. That meant no real sense of security. Poverty wages, the whole thing. While doing that, I was roasting coffee, bartending, doing day labor — all these things I’d always done to make ends meet.

By this time, a couple of the guys that I grew up playing in hardcore bands with who studied film and design had made their way into the advertising world. They were, moving up the ladder, becoming art directors, and starting to make some real money. They told me, “You’d be so good in this world. We know you’re broke, come try writing ads.”

So I started pounding the pavement trying to get gigs and then impress the people who’d give me gigs. I was getting paid by the piece, it wasn’t much. At one point I had some friends with a small agency who were pitching Starbucks. I’d worked in all corners of the coffee industry, won barista championships even, so they let me write the pitch. And Starbucks wanted it. That was a pivotal moment for me that enabled me to get more legit work.

Then in 2013, Alex Calderwood, one of the founders of Ace Hotel, had just died. The company was just starting a really exciting period, pushing into new markets, and it was a major blow; he was the voice of the brand. Alex’s way, and the brand’s approach, was to embrace the misfits, the outsiders, the punks. He mentored people, he brought these rebels into the fold. That was a big part of their success. So they were looking for someone with some of that outlaw, visionary spirit.

I interviewed for the job, Creative Editor-in-Chief, and got it. That was a dream job. I was working with such cool people — me, an architecture person, interiors, graphics, all creative-directing the brand together. I felt like I’d made it. Of course, your understanding of the world and your possibilities inevitably expands and you start looking for the next challenge. Being in Portland, I eventually felt the gravitational pull of Nike.

How did you end up at Nike?

I grew up obsessed with sport in the era of Michael Jordan. I was obsessed with Nike specifically. I remember tracing the Nike swoosh onto the fogged up glass when I’d take showers as a kid. When I was 12 years-old, I wrote a letter to Nike, at 1 Bowerman Drive, telling them I wanted to work one day. And they sent a letter back! Do your best, that’s great, thank you, and so on. My mom saved the letter, she actually found it right after I ended up leaving Nike.

Here’s the thing: I’m not good at networking, those mingling-and-drinks events. I just can’t do the smile-and-nod, the polite chuckle. I’m allergic to it. Growing up broke, I think there was this sense of class inequity that created a tension — I always felt like an outsider. Especially as a DIY hardcore kid, there’s an ethos of, I don’t need you, I’m just gonna do my own thing. But Portland isn’t that big, so I eventually met somebody at Nike who I hit it off with.

My first job at Nike was in their innovation accelerator. It was the sort of thing where they needed someone to start today, and I said yes. We’d build little startup brands within the Nike ecosystem, do a couple rounds of revision on them, pitch them into the larger organization, and they’d either buy it and it became a Nike brand or they’d kill it and we’d move onto the next one. That was my first chance to really build something from the ground up in advertising.

You clearly understand how to sell a vision and lead other creatives — can you speak on that?

One of the biggest things is finding people with passion or — people forget this — inspiring people to become passionate if they're not. Everybody's passionate about something, sometimes you just have to help them to it. There are some people who are just passionate humans, who can essentially deploy passion as a skill or way of living. Then there are people whose passion is buried deep beneath the surface and you really have to find the right time and place to see it expressed.

It’s great to find those passion-as-a-skill people in the first place, but it’s on you as a leader to create a space that brings passion out from the whole group at the same time. There's something really powerful and empowering about living a life that's surrounded by creating things, thinking novelly, and experimenting. That’s the passion you need to look for and foster: passion for life, not passion for work.

Besides passion, you make good stuff when you’re striving for excellence. In my personal creative endeavors, I’ve always had an experimental, novel approach. Coming into this world through Ace and the Nike innovation accelerator work, the philosophy was always that you can’t just do the thing that everybody else does.

If you’re a small team or brand especially, you have to be experimental to punch above your weight. No matter your size, you want to differentiate yourself from your competitors.

So many agencies just look at the ads other agencies have done and do their own versions. Look at Old Spice — Wieden + Kennedy did that years and years ago and now so many brands have their own versions of that, to varying degrees of success. After the first one, it’s super stilted thinking, lazy, and deeply uninteresting.

There's always compromise in this work. But you can't be compromising in terms of your vision. If you don't have that vision then there are a million people along the way, that if it's not clear to you, will just carve away here, make a little cut there, and all of a sudden you’re just making stuff by committee, and it's based on backward looking research, and you're just following other brands that have already done good stuff. That just sounds awful to me, that sounds like a very sad shadow of what I want to be doing with my life.

Do you have any advice that somebody gave you years ago that has guided how you’ve approached your career?

Years ago, before I got the job at Ace, this guy Jeremy Peller agreed to have a coffee with me. He’d been at Ace, he’d done the WK12 program, and at this point had his own shop, OMFGCO. My background is copy and his shop does design, but I had a lot of respect for him and wanted to learn from him.

He was the person who really nailed this into my head: never make anything, truly ever, that you don’t feel proud of and passionate about. He told me, you can get a role doing what you do wherever, but most of the time it’ll be a dead end. If you really care about making beautiful things in the world, you can and will find a role and company that allows you to do powerful work without really compromising.

“If you just keep pursuing the goal of making beautiful things,” he told me, “you will build an incredibly rewarding career.” This was when I was still doing piecemeal copy gigs. He said, “Just keep bartending and supporting yourself while working on the copy stuff until you get that gig that lets you be an artist.”

Six months later, I got the job at Ace. He knew some folks there, he heard I’d got the job, and basically said, “told you so.”

When we got that coffee, Jeremy asked me if I'd ever read this book by Lewis Hyde called The Gift. I had, and I told him it was really important to me, that it taught me about gift culture in our capitalistic world. He told me it was the most important book in how he approached his advertising career. That blew me away! Thinking about that book and my work in a new light allowed me to reposition both the work I’d done on my own and my approach to commercial creative work.

When I’d started a poetry journal, I hadn’t thought about it as a business to make money — it was just that I wanted to put out books by my friends and get them to come to town and read poems. Same with my years in bands: I just wanted to play music and travel. I realized I could approach commercial work like that, too — focus on just making incredible stuff first, not the money, and the money would come.

That one coffee really changed my life. I’ve thanked Jeremy many times over. The first time I did, after I was hired at Ace, I said, “I don’t know how I could ever repay you.”

He just said, “Dude. Just do the same thing for everybody else.” So now I just try to be that guy who shows people the way, for anyone who comes to me like I came to him.

Talking about these mentors, how does mentorship figure into your working life now?

You’ve got to create the world that you want to be in, and you've got to create it for other people too, because nothing exists in a vacuum. 

I was a creative writing professor and that gave me really deep experience in terms of learning how to mentor people. Sometimes I was teaching a graduate-level workshop, sometimes I was teaching teenagers, but regardless, I needed to create a space for people to conceptualize their own creative vision. Then I had to set them up for success and show them how to make a plan to realize their vision. I guided them to actually do it, and then pushed them to do it and redo it until it was great.

Doing that teaching work in an academic, fine arts setting allowed me to develop those mentorship and leadership skills before I ever knew about the advertising world.

I've also coached my son's baseball team for the last 10 years, and those two things, as well as coming from a working class background, are what define how I mentor and help people.

I like to think I’m passionate about leading a team. Goes for my son’s baseball team, goes for my team at Headspace. Not in that slimy “we’re a family,” way — your coworkers are not your family. Never forget that. But I care about my team, I care about their wellbeing, and I care about them making stuff they’re passionate about. It’s on me to set them up for success.

Lastly, back to that book, The Gift. One of the core learnings from that book is: don’t just ask for something from someone. Give them something first. That’s true for people interacting with people and, by the way, that’s true for brands trying to reach people. Start with the gift, don’t start with the ask. So you need to give to the people you work with if you want them to give back to you.

What’s your opinion on high ego versus low ego in the workplace, especially as it relates to collaboration?

You have to have ego and swagger to make great work. It won't get made if you don't. It protects your team from bullshit. It helps you navigate relationships outside of the team you're creating with.

But if you bring that ego into the team that you create with, you’ll ruin it all, because you might as well just be working by yourself. For me, it’s performative in some ways, but it also comes from having a lot of experience in life, being in a lot of tough spots and knowing that there was nobody to help me out, that I had to get through it myself.

That gives you a sense of the raw ingredients to get through a challenge, but I want to stress the balance there: you have to know when and be able to shut that energy off and make it about the work. That's the key: you can't be arrogant about the work. You have to be humble about the work and who you're working with. You have to serve the idea and the work, not yourself. 

There's this great John Cage quote: ”out of the work comes the work.”

That’s one of my mottos for both my team and for myself. The best idea wins, and if the best idea isn't winning, then I'm not doing my job as a leader and as a creative person. Ego can help that idea win, but if you don’t turn it off at the right moments, it’ll be very destructive and the work will be off.