The Biggest Hurdles We Faced
The hardest thing about opening a bouldering gym in SE Portland, was dealing with the city of Portland. We budgeted 50k for architecture fees, 150k for permits, and had an oh shit fund of another 150k. We had spent the entirety of covid doing home installs, and building walls in schools, refining our ability to build whatever we dreamed up. We had a cnc up and running that could cut 4ft by 4ft panels, and had pre-made over 100 volumes, and 120 4’x4’ t-nutted sheets. We thought we were set! It turns out permitting in Portland is hard work. Everyone told us it was hard, but no one told us just how hard it would be. It was over a year from when we bought the building, and when we were able to “start work” on the project. I say that, but we plugged away that whole time, doing what we could to keep the project moving, painting over graffiti, cleaning up broken windows, designing and cncing the climbing wall panels now that we had a space and had finalized the design.
An example of the stupidity of Portland permitting, one of 40 or 50 different problems we ran into while doing this project, was we were told we had to replace the windows before we could open, as they did not meet energy code requirements. We knew enough not to get a historic building, but the building is a non contributing resource in a historic district, meaning we can't do anything without permission from both the city, and a community led group of people who live in the neighborhood. All this is to say, we ran the planned, historic matching windows by the EA meeting city planner, and they said they looked good. Well, historic matching, custom wood framed windows (which were required for the neighborhood) are 5-8k each, and take 8-12 months to get made. Once the city said they looked good, we ordered them, and waited. 3 months before opening, right around when the windows came in, we got an email from someone else who came back from vacation and told us we couldn't install those windows without going through something called HRR, which would add 6-9 months to our timeline to open. We fought, looked at loopholes, and managed to get them to agree to go through HRR after opening, if we didn't replace windows till after HRR. So our hold room is filled with 55k of windows we can't install, and they want us to repair the existing windows. Which are mostly so rotten that there isn't anything left in the holes, and we had to board them up with plywood anchored to the concrete. This is ONE example of a hundred different things like that we had to deal with, and are still dealing with.
Outside of construction, the biggest challenge we faced was getting insurance for our 24/7 model. Securing insurance for a gym that’s open around the clock was an uphill battle. We had to navigate multiple rejections and find a provider willing to understand our commitment to safety and the security measures we put in place. It took a lot of research, negotiation, and persistence to finally get the coverage we needed. Six months of dedicated work, and over 300 pages of documentation, countless revisions, and insurance finally said yes to 24/7 access.
Building Our Dream from the Ground Up
One of the most rewarding parts of our journey was building every aspect of Skyhook Bouldering with our own hands. From the walls to the volumes and even reroofing the building, our team poured countless hours into making our vision come to life. The construction process was anything but easy—long days of lifting, drilling, sanding, and troubleshooting—but each step brought us closer to creating a space we were truly proud of.
Designing and constructing the climbing walls was a massive endeavor, requiring precision and creativity. We wanted every angle and hold placement to be thoughtful and engaging. Building the volumes was a true labor of love; we spent late nights cutting, assembling, and refining them to make sure they provided fun, challenging experiences for climbers. If I were to do it again, I would make less volume types, instead I would have a handful of really solid shapes, and then mass produce them in bulk, at different sizes. This would have led to better visuals on the wall, and cut down on production time and the learning curve for the crew working to assemble the volumes.
The actual construction part of doing the building construction went well enough. We lucked out by being kind, helpful and asking people in different industries for help, and they ended up teaching us the different trades, and were willing to contract with us for the trickier parts. This included reroofing, painting, concrete work, and structural work (not structural steel, but the parts that didnt require that welding cert). It was a back-breaking, sweat-inducing process, but the feeling of standing in our completed gym, knowing that we had built it from the ground up, made it all worth it. We didn’t just create a gym—we built our dream, and we’re thrilled to share it with the community.
Key Lessons Learned
Stay Flexible and Resilient: If there’s one thing we learned, it’s that even the best-laid plans can change. Insurance and permitting delays forced us to adapt, stay patient, and not get discouraged when things didn’t go according to schedule.
Lean on the Community Early: One of our smartest moves was engaging with local climbers from the start. We kept everyone updated on our progress, hosted pop-up events, and asked for input on what they wanted to see in their new gym. This support kept us motivated and gave our opening a sense of shared excitement.
Prioritize Quality and Vision: Every decision—from the structure of our climbing walls to hold selection, third space design, and 24/7 access—was driven by a goal of opening the best bouldering gym in Portland. We realized that investing in high-quality holds and thoughtful route setting was essential, and even though the insurance and permitting challenges tested us, we came out stronger and more committed to our values.
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