Matt Ruddy portrait by Ben Moon

What drew you to the Oregon Timber Trail?

I had the good fortune of living with a friend here in Portland, Steven, who pointed me in the right direction to get back on a good bike (a Specialized Crave Comp hardtail nicknamed “Peacock” because of the flashy colors) and that led to many good friendships in the trail riding community (Abraham of AFB, Nat West of Rev Nat’s Ciders, Ayleen Crotty, and many more). Some of my happiest times since moving to Oregon in 2011 have been on a bike, in the woods, with friends. It feels a bit surreal to be able to focus on that for a living by helping people do that.

What do you hope to accomplish as the Executive Director?

I’m grateful to have worked in a wide variety of capacities, but this will be my first time serving as an Executive Director. These positions often feel out of reach for many people of color, particularly in the outdoor industry. I would like the trail community and partners to know that the time, consideration, and thoughtfulness that the hiring committee gave in applying a DEI lens to their approach was noticed and appreciated. 

I would very much like to help the OTTA reach its goals in increased visibility, increased funding and support for paid positions that recognize the enormous amount of hard work that has been dedicated to building the organization, and to keep striving towards creating trail experiences where everyone feels that they belong.

I also strongly recommend the book “Range” by David Epstein for ideas on leadership, flexibility, and looking at things differently. For those of us who have worn several different hats throughout our career trajectory, it makes a strong case for pulling together a variety of experiences and living a well-rounded life.

You’ve volunteered and attended Mountain Bike Oregon the past. What do you love about MBO?

Oh, MBO, so near and dear to my heart (and legs and arms and lungs). The trails in Oakridge are stunning, the people in Oakridge and Westfir are wonderful (the trip to Ray’s Market and Brewer’s Union Pub always feels like the MBO weekend has officially begun). There is nothing quite like belting out a loud whoop on the last stretch of Alpine to let the campers in the valley below know you are making your descent. Even better is turning left on the river trail to the swimming hole to dunk your legs in. 

Tell us about your first mountain bike

My first mountain bike was a black and purple Diamondback Sorrento circa 1988 or 89. All rigid frame. It was the first bikepacking rig for a trip to Vancouver, BC. I spent 3 days there visiting my favorite red fire engine in Stanley Park and rode over the Lion’s Gate Bridge to West Vancouver to visit Lighthouse Park to do some climbing with friends. I remember a kid at the KOA campground being impressed that I had two water bottles on my bike. That convinced him I really meant business.

Is there a connection between music and mountain biking?

A sense of rhythm?

Absolutely. I’ve found that I overthink my riding sometimes (as we all do) and one of the ways I’ve managed to give that part of my brain something else to do is to hum or sing a few of my favorite tracks while descending more complicated runs. It frees up my body to react more naturally by focusing on keeping things in tempo/time/rhythm. A few of those favorites happen to be “Diamonds on the Soles of Her Shoes” by Paul Simon, “Bring the Noise” by Public Enemy, and “Alright” by Kendrick Lamar.

You were a junior high school music teacher in New York. What did you love about being a teacher? What did you learn while being a teacher that you’ll bring to your position as ED?

I was the instrumental music teacher at PS 126, the Jacob Riis middle school on the Lower East Side of NYC from 2000 to 2007. Thankfully, because of a grant from VH1’s Save the Music project, I was able to start a music program there which grew to include a 6th-8th grade wind ensemble, percussion ensemble, a guitar class, and an after-school rock band. Over time, my friendships and connections with the families in that neighborhood became very dear to me. I was walking to the 6 train at City Hall after school one day and, while passing through the courtyard of the apartments near the school, I heard “Ay! MistaRuddy!!!” from one of the fourth or fifth-floor windows. I looked around and couldn’t figure out where it came from. The next day, one of my students came up to me and said “yo, MistaRuddy, how come you didn’t answer your phone when I called?” I had no idea what he meant. He smiled and said, “I rang you up on the ghetto phone!” I said, “oh that was you?!” We busted out laughing and I always made sure to holler back when he hit me up after that. “MistaRuddy” stuck and became the name I use for writing and publishing, recording music, and eventually what I chose for my consulting business. Earning the respect and credibility of those students means just as much to me as any Ph.D. or title.

My love for teaching comes from those moments when something clicks, the light bulb turns on, and a student has that “ooh wow” moment of realizing that they can do it. I’ve had many good teachers in music, writing, and literacy along with many inspiring colleagues at the K-12 and higher education levels. There is a sense of adventure in the inquiry, investigation, and creativity of learning that I hope is always worth pursuing. I learned that good teaching relies on good communication. I learned there is much more to be gained by having power with not power over the students. I learned that it is not my responsibility to be the expert on something, but the facilitator of learning experiences. As ED, it’s not my job to be the raddest, shreddingist, flow bro on the trail. It’s my job to help organize the spaces and places where the abundance of talented and dedicated people can help others experience the Timber Trail.

You work a couple of nights a week at Mississippi Studios, doing production and management. What is that like? 

I spent about 5 years on the road as a tour manager with bands and musicians. I was taking a break from teaching, a self-elected sabbatical of sorts. You learn a lot about yourself and others while spending 4-6 hours a day in a van, 3-4 hours a day of loading, unloading, setting up merch tables and sorting out meals and places to stay. One thing that really hit hard during the pandemic and quarantine was not seeing or participating in live music. The first few nights back, seeing some of my favorite bands and people, was very emotional. I got back into production and music in a way that lets me stay home but also allows me to now be on the other side of welcoming those traveling bands and musicians to Mississippi Studios and Polaris Hall (I often end up helping at The Aladdin Theater and Revolution Hall but less frequently).  Knowing exactly what it’s like to finally arrive after driving down from Seattle, up from San Fran, Humboldt or Ashland, and having someone there with some of those details already sorted out is very rewarding. Seeing people on stage or in the crowd enjoying themselves is also ‌very rewarding. Music is good for our souls in so many ways that it makes some of the more tedious tasks less daunting because it’s all going towards an experience that moves people. Most of it is communication. An efficient load-in, soundcheck, dinner, show, and load-out saves everyone time and stress. 

Is it important to you to be a part of the Portland music scene? What do you love about it?

It is. There’s an awful lot of talent here, particularly in the folk/Americana/bluegrass scene, which is where I find myself most of the time. There are also people on the production side who really embody the hustle and hard work of helping shows run well, the studio process of recording, and many of the ins and outs of a thriving “scene”. I’m lucky to know and learn from some pretty fantastic people who have become dear friends over the years.

Favorite album and why?

I’ll go with Paul Simon’s “Graceland”. As a collaboration, it is phenomenal. It also became a conduit for me to so much music and so many musicians from South Africa and Zimbabwe. Graceland sits at the top of the list because it led me to many people and musicians who have had an enormous impact on my life. Ladysmith Black Mambazo, Hugh Masekela, Miriam Makeba, Bakithi Kumalo. One of my first lengthy tours was with a group of musicians from Zimbabwe named “Bongo Love”. A highlight from that tour was opening for Ladysmith Black Mambazo in Corvallis, OR. We were invited to join them on stage for their encore. After the show, I had a chance to sit with one of the group’s founding members, Joseph Shabalala. I thanked him for his music, mentioning that I was pretty much raised on it. He passed in 2020 and, during their next performance in Portland, his four sons, and several other family members who are now in the group, honored him in song. Hardly a dry eye anywhere in the audience. 

There are two of my favorite Zulu phrases that friends from Soweto shared with me.

“Iskhati si shwebene” doesn’t have a direct, literal translation but it embodies the idea that time has wrinkles. Some moments feel like they take such a long time and other things feel like they happen in an instant. I very much got the feeling of that while visiting Soweto. The way the people are, how they move, and what stresses they do or do not hold onto in terms of a “schedule.”

The other is: “Inkhatazo zi ingama kufikela kusasa” which means “my worries can wait till tomorrow.”

You are a proud veteran, having served with the Pennsylvania Army National Guard for five years. What did you take away from that experience?

Teamwork. Purpose. Much of my work has been in Diversity, Equity, and Inclusion. I have found that the acknowledgment and understanding of differences is vital to learning from instead of labeling each other. However, I found that the learning curve and openness to that work is much more successful and the bonds become stronger when a school or an organization returns to its mission, its purpose, its unifying reason for coming together. Everyone who went through basic training knows their “battle buddy.” We were expected to learn as much as we could about them because we were watching their back and they were watching ours.

I was in an infantry unit from 1996 to 2001. I did not have to face the challenge of a combat deployment during those years but I did have the privilege of serving with other veterans who had. Their mentorship and leadership have stuck with me and I’m grateful to have served with them.

One of the highlights was 3 weeks in Lithuania for a multinational training exercise called “Operation Baltic Challenge”. It was a collaboration between the soldiers from the Baltic countries of Latvia, Lithuania, Estonia, and Croatia, and soldiers from Finland, Sweden, Norway, ourselves, and a Marine Corps Reserve unit. Sadly, the reason for the cooperative training was to help those Baltic countries prepare for exactly what is happening now in Ukraine. 

Why are backcountry trails like the Oregon Timber Trail important?

I think the backcountry trails are where many of us find peace for ourselves. Hikers, bikers, explorers…I think we love what nature does for relieving us of the stresses in life. If we are going to take good care, to take better care, of the planet and places we’ve been given, I think education and stewardship are vital. In reference to the previous question, the trails are a chance for people from many different backgrounds to see some of the most beautiful parts of Oregon, to visit the small towns where the restaurants and shops are run by hard-working folks, and spend time in nature recharging themselves, hopefully finding some peace after these recent hard years of isolation.

What inspires you?

Family and friends. A dad who grew up in New England and became a nuclear engineer. A mom who spent decades helping struggling readers improve. Musicians and artists who have spent years writing and recording and creating without the certainty of success, not just financially but recognition that they rejuvenate our hearts and minds. Teachers who are doing all they can in an imperfect educational world. The folks in health care who are exhausted from the past few years. Andre Middleton of Friends of Noise (helping kids learn sound engineering and host live events), Randal Wyatt of Taking Ownership PDX (helping homeowners with vital repairs), Laura Multon of Street Books (bicycle libraries for those without shelter). Last and certainly not least, the hundreds, if not thousands, of people between staff and volunteers who make some of Oregon’s most beautiful spaces and places possible. Trail stewards, event organizers, and more. I was recently at the Oregon Governor’s Conference on Tourism and it was amazing to meet so many people dedicated to bringing us together and making sure we have a good time doing it. It was 2011 when I came back to the PNW (born in Tacoma) because it’s the place that feels like home. That feels the truest in the woods and on the trails. I am very excited to begin this next adventure and can’t wait to see you out there.