Fail Fast, Fail Forward: The 20-Year Lesson That Made Me a Mountain Ops Director

Early in my career, I thought building the cleanest, biggest terrain parks was how I was going to make a name for myself. I wanted to prove to my company that terrain parks were worth the investment and build the best park program in the Southwest.

I spent my nights figuring out how to stick two pieces of metal together for the next donkey rail, hunting down remnant snowmaking pipe to replicate 8" tubes I'd seen in Unbound video parts, or throwing temper tantrums in the cat after a 45-minute battle trying to smooth out a tiller hop on a 30° takeoff transition.

In all that obsession, I lost sight of what actually mattered. I was fighting my leadership instead of listening to them. As it turns out, business, much like life, is really about relationships. Any good relationship starts with a baseline of trust, and trust is built and maintained through clear communication and collaboration. They were trying to tell me what I needed to know to be successful.

My then-Director of Mountain Operations, a 40-year industry veteran, used to tell me repeatedly:

"Yosh, it needs to be three things: packed with people, fun, and safe."

Fail fast, fail forward, right? It took a lot of hard lessons for me to realize I needed to talk less, listen more, and deliver what my superiors were asking for at a baseline. Once I checked those boxes, I earned the freedom to do what I really wanted to do: build progressive terrain parks.

All these years later, nearly 20, that same leader is now our Chief Operating Officer, and he's transitioning me into that Director of Mountain Operations role. We recently reminisced about that "three things" conversation, and we still laugh about how much easier the journey could have been if I'd failed at listening just a few less times.

Three pillars that turned our operation around

Look, it's not rocket surgery. If we handle the administrative side well, we get to focus more on what matters to us as terrain park operators: building sick parks. We turned our operation around by focusing on three pillars:

• Comprehensive team training: Grounding every builder and digger in a risk-first mindset.
• 100% digitized workflows: Replacing cocktail napkin designs and "dog ate my homework," water-stained, illegible paper with digitized Ullr documentation for leadership approvals and incident investigations.
• Rapport across departments: Proving our professionalism turned ski patrol and mountain ops from skeptics into partners, and shattered the old stereotype that park crews are just dirtbags riding on the clock. We built trust through Jump Measurement Clinics led by the park staff, and we became a resource for the patrol team during investigations in the park.

Here is the truth: an operational focus on risk management allows the entire team, from the C-suite to the cat seat, to feel comfortable pushing the envelope of progression, because everyone knows you are doing it the right way.

When your documentation and processes are locked down, you get less paperwork headache, more time on the snow, and total trust from your leadership to build bigger, better, and bolder.

Lock down your operations. Protect your creative freedom.

At Ullr, we built our software around this exact operational standard. We replace old "dog ate my homework" opening and closing logs with a seamless, digitized workflow to document every build, inspection, and maintenance entry in real time. That gives your leadership total transparency, your park crew total backing, and your builders the freedom to keep pushing creative boundaries on the hill.

Built explicitly for the realities of mountain ops, Ullr gives your team:

• Digital park logs and inspections: Complete daily checks and opening/closing logs fast, working offline-first anywhere on the mountain.
• Comprehensive build logs and feature history: Keep detailed, searchable records of every build, modification, and photo setup so you can go back in time for incident defense.
• Solo jump measurements: Follow industry best practices with step-by-step jump measuring tools, including Moasure integration to measure distance and slope in a single pass.
• Real-time visibility and guest updates: Turn your build logs into live, interactive park maps for your resort app or website so riders know what's set up.

Protect your passion. Schedule a demo and we'll show you how it works.