Stride: You’ve been an independent filmmaker and photographer for 10 years. When did your interest in film start?

Keenan: I’ve always been interested in cinema, but I never thought it could be a viable professional opportunity. When I was young, I didn’t know any storytellers, filmmakers or photographers. I thought there was this lucky crew of people making those things a profession, but I never could. It didn’t even feel real to me.

Stride: How did filmmaking become more real to you?

Keenan: I took an intro film class in college and absolutely fell in love. Cinema was really exciting because it was history, psychology, philosophy, contemporary art and art history all mixed into one form. I wanted to draw from many disciplines and combine them in a way that felt real and unique. The lightbulb went on during that film course… this is where it’s happening.

Stride: When you graduated, were you prepared to give the freelance film world a go?

Keenan: Not at all. I immediately got a job working at a start-up in sales. I lasted two months [laughs]. Every single day, I was thinking about writing a story or taking a photograph… just dreaming of filmmaking. I got to a breaking point and realized the only way I was going to make films was to make films. That was an intimidating realization, but it was the only way. I called every single person I knew doing work in the film industry. A friend of mine had a film shoot coming up, so I quit my job and went on a film shoot the very next day.

Stride: Wow. How did you just make that move without worrying if it was the perfect next step?

Keenan: It’s really easy to feel overwhelmed during a transition period – unless you’re already immersed in something or you have a clear path, you can’t do it yet. I fundamentally disagree with that. No one has a clear path [laughs], and everyone’s entire life is a transition period. I didn’t discriminate between any type of job at all –  if somebody wanted to hire me as a production assistant I’d do it, if someone wanted me as a producer, I’d do it, if someone wanted me as a cinematographer and I had no idea how to use the camera, I’d say yes and figure it out on the job.

Stride: So you had zero ego going into your film career?

Keenan: I couldn’t because I didn’t have any experience. I had this old professor, he must have been 87-years-old. He said, get the opportunity first and figure out how to do it later. That has been super influential on my career.

Stride: When did it feel like you truly became a filmmaker?

Keenan: One day, my film advisor at Stanford straight up called me out. He said, “You’re not taking this seriously. Making films is a very real opportunity, there’s hundreds of thousands of people doing it professionally. You didn’t go through 4 years of education to be wishy-washy back and forth about it. Take it seriously.” At the time, there were a ton of companies in the Bay Area that needed videos, so I used that as my film school – those experiences were my way to learn this industry. Everything started to change when I committed to my creative pursuit 9-5.

Stride: Did you feel like you were making a financial tradeoff with that decision?

Keenan: Yes, absolutely. But for me it’s always been about value — I made the decision early on that I didn’t need to be rich. My priority was making something creative, traveling, talking to strangers and getting lost in the middle of nowhere. I saw more value in those real experiences than any amount of money. Making money to create those experiences was an indirect approach… I just did those things and figured out how to make money.

Stride: The creative process – coming up with wild ideas and stories – is an extremely vulnerable experience. Have you dealt with any mental baggage?

Keenan: My baggage was not having confidence in myself as a storyteller. I thought I’m the business man in this creative world. I’m the one who’s organized and practical and prepared. I’m the support, not the person fueling the creative ideas. So I spent a lot of time as a producer, basically the team manager. Then the company I started with my friend started getting simultaneous projects, so we both had to direct films. That was the first time I had 100% creative ownership.

Stride: Was it rough directing your first couple of films?

Keenan: When I first started directing, I was super overwhelmed by how much depth was involved in the role. I made a ton of mistakes. One of my first big commercials, I basically shot an entire film that had no transitions – we didn’t shoot any material that moves you from scene to scene. We got to the editing room and were like well, that sucks [laughs]. There have been many bumps in the road that informed and made me more confident. All of that confidence either came from people challenging me directly or making mistakes.

Stride: I know almost all creatives struggle with how much work they need to do for the money, and how much work they can pursue as personal projects. How do you approach that blend?

Keenan: I used to do 100% commercial jobs, now I’m about 70% personal projects, 30% commercial jobs. One thing my girlfriend and I always say is you get the jobs that you take. If you’re a commercial filmmaker and you take a ton of jobs for car companies, you’re the car guy. It’s important to maintain a balance between the creative progress and the commercial progress. Any personal project I do is going to be something I can use to get commercial jobs, and the income I generate from commercial jobs is used to fund personal projects.

Stride: I know you think deeply about ethics and storytelling. Tell us about that.

Keenan: I’m happy doing commercial projects, but some aren’t good for my community. I’ve turned down jobs with major food corporations because I don’t support how they treat their animals. I’ve turned down jobs for large banks because I don’t believe those banks are treating my community fairly.

Stride: Is there a tradeoff between making money and having strong ethics in the film industry?

Keenan: Yes, there’s definitely a tradeoff. I could go and make commercials for oil and gas and banks and be super rich. I could buy a house with every commercial. Those types of commercials are multi-million dollar budgets for 30-second commercials. That’s an example of something I would never do that presents a monetary tradeoff.

Stride: Who is the most transformative character you’ve met along your journey?

Keenan: In May, I was driving back from a weekend in Colorado from a film festival… hanging out with the hippest of the hip crew and schmoozing in that game [laughs]. I was coming from this surreal experience with lots of similarly-minded people tossing around lofty ideas that aren’t grounded in anything. I got on the road and drove home on the Loneliest Highway in America, US-50. I stopped in Ely, Nevada, a town I’ve always been super curious about – there’s a large Shoshone Indian Reservation and these historic, iconic American West brick buildings. And all these burnt-out casinos that are dark and full of smoke 24-7. Just a strange kind of place.

I saw this man with a very interesting look and asked him if I could take his portrait. He said sure but asked me to take a walk with him first. What I thought would be a very quick interaction turned into a 7-hour detour where I sat and talked with this man all day. He was an old man, 76-years-old, and at face-value a drunk… I thought he was homeless, but I was wrong. He walked me to the historical preservation society and showed me the 12 buildings he built by hand with a crew of 12 ex-convicts. He had created this homage to the history of his town – this really elaborate historical icon in a place where 90% of the people drive through without even stopping at the McDonald’s [laughs]. It was amazing to me. It meant so much to him and I respected that. There was a lot more to this person than a guy sitting on a bench smoking a cigarette, so I just sat there and listened.

Stride: Is this an interaction you might ultimately do something creatively with?

Keenan: I’ve already written 3/4 of a photo essay about this experience. There’s all sorts of fascinating things about this man – he lived at the top of a 10,000 foot mountain for over a year. When I asked him why, he just said “because I wanted to” [laughs]. I asked how he got his food, and he said, “I had a friend bring it to me.” I thought these simple answers were so great – what seems outlandish to more traditional Americans were the simplest decisions in the world to him. He wanted to be close to nature and live at the top of a mountain, what else do you need to know [laughs]?

Our conversation came to a culmination when he said, “I think it would be funny if you wrote a letter to the Sheriff about me.” At first I was confused and felt like this whole thing was a con. But then I thought more deeply about it, and he genuinely thought it would be funny if I wrote the Sheriff. The Sheriff was in his 60s and someone this man had known since he was a kid. So I’m going to do it.

Stride: Amazing story. What’s the biggest challenge in your creative journey?

Keenan: [Cuts in quickly] Writing a narrative film and directing it. I fell in love with the magic of cinema… the characters and worlds you can just create. Inventing stories is the pinnacle of cinema. The elephant in my room is the fiction film. I have ideas, but I haven’t dedicated the time it takes to actually get something on paper. I’m excited now because I’m ready to take that step.

Stride: You’ve traveled all over the world, where is your favorite place?

Keenan: [Long pause] God that’s such a hard question. I’m so drawn to Alaska for reasons that are very hard to explain. The raw environment is like nowhere else I’ve been. The fact that you can actually live off the land up there is something I find really interesting. This summer I spent 6 days in a native community in NW Alaska and learned about subsistence living. I still don’t know shit [laughs], but it was fascinating to see that lifestyle. Alaska has subsistence potential and the raw beauty of the ocean and mountains… the land in Alaska is really something special.

Stride: What do you think is the biggest health concern in the United States?

Keenan: Not being responsible for what we eat. We’re separated from our resources – I was just up in Alaska learning about salmon fishing. Salmon is one of the most widely consumed proteins in America, and people understand it as a fillet they buy in Costco. I grew up in a farm town in the CA central valley, where I could pick peaches and I knew the cherry farmers. A huge part of that is being a privileged white suburban kid, but it was a really fascinating way to learn about food. I think it’s possible to create access to local, nutritional foods on a massive scale. Everyone says it’s not possible, but I think it is possible. It’s a really really difficult way of exploring the connection between the ground that we walk on and our health as individuals.