A Little Cup of Chocolate

“His last name is just so rare and fun-sounding, I have to believe it must mean something very specific — like, ‘little cup of chocolate.'”

I laughed and shook my head at my dad. We were heading to Colorado to visit family friends in Grand Lake, but first with a stop to the Front Range. There, we’d visit Colorado College, my eventual alma mater (though at the time I was undecided) and link up with my dad’s friend, John (“Captain”), in Boulder. My dad had asked Captain if he knew of any climbing guides who could take me out on some real rock. One of the strongest pulls for me to go to college in Colorado was rock climbing, but as a primarily gym climber, I wanted to see and feel the rocks myself. Captain knew just the guy: Rob Coppolillo. Or as my dad would henceforth refer to him, Rob ‘Little Cup of Chocolate.’

When I met Rob, I didn’t have an inkling of how incredibly talented and smart he was. He was friendly and quick to laugh as he led me through Eldorado Canyon for some sport climbing. He took me across my first Tyrolean traverse and brought me up to heights I had never reached. We had an awesome day — so much so, that when I committed to Colorado College, I went out with him again before freshman year orientation began. He supposedly told my dad that I was going to surpass him as a climber in no time. “She’s a natural-born crusher,” he declared. I’m still honored to have received that praise.

Several years later, I was in my second semester of senior year, desperately trying to figure out some sort of “career” for myself. In an effort to network, I reached out to Captain to see if he had any contacts in the Boulder area he could connect me to. Over a weekend, Cap introduced me to folks in the bike and beer industry — but he also arranged breakfast with Coppolillo.

Rob was as congenial and knowledgeable as ever. He offered to connect me to some of the head editors of Climbing Magazine. (While in college, I discovered Rob himself was a regular contributor to the publication. He never mentioned it — talk about humble!) He insisted that places that were going to blow up included Las Vegas and Grand Junction. Now, years down the line, I can say he was right. I can easily envision myself in either place, drawn to the climbing, growth, and other outdoor pursuits in both. As we sipped coffee and ate possibly the best chocolate chip muffins I’ve ever eaten, I couldn’t help but feel so grateful for him and Captain to spare me this time. (Captain later told me that given Rob’s propensity for chicanery, he’d given him a “stern talking to” before guiding me outside and later meeting over breakfast. Given that Captain is a hooligan himself, I can’t imagine what he could’ve possibly said.)

I was aware that Rob decided to move his guiding business to Chamonix, France, some years back, but I was absolutely tickled to receive a Facebook message from him in December of 2022: “hey bud, great to see you are still climbing and going good! how’s vegas?! you’re done with CC now, eh? what you doing? we moved to chamonix for a couple years, but now in seattle. see you ’round, i hope! best to your dad, rob.” It was so out-of-the-blue. I had gone to Vegas to climb for my birthday (once again, he called it), and he must have seen the photos I posted a month after the fact. There was no reason for him to reach out like this, but he did.

And he did it again! This last summer, while out on the road, I hit a professional crossroads. I was tired of doing jobs that didn’t relate to my real passion: writing. I posted in an outdoor industry Facebook group, seeking advice from others on how to break into copywriting for outdoor brands. A day or two later, after receiving several comments and insights, I got a notification: “Rob Coppolillo commented on your post.” I can’t remember exactly what he said, but it was short and sweet. Something like, “hey bud — let’s chat!” I immediately messaged him to get on a call with him.

Over the phone, I learned just how extensive Rob’s copywriting background was. He’d written for the likes of huge outdoor brands, not to mention all of the climbing articles and two full-on manuals to mountain guiding and ski guiding. The guy was so well-versed on these subjects and just a total badass, and you’d never know it if you just met him in passing. I told him I’d be in Seattle on the tail-end of the road trip, and he immediately encouraged me and Ryan to come climb with him at Seattle Bouldering Project.

At SBP, it felt not only so great to see Rob’s familiar face, but experience that full-circle moment. He was casually bouldering around, admitting he’d been working to get more into ski shape for his guiding season — less so climbing shape. He used his free day passes on the two of us and encouraged us to stay as long as we’d like — even come back to the gym later if we wanted. He was crunched for time but still made the effort. We took a selfie for my dad and Captain, to commemorate the moment:

I last saw Rob on my birthday, November 18, 2023. I had driven up to Boulder to do a couple of errands, but also just to see him (he was in town just a few days) and Captain. While I had seen Rob just a couple of months prior, Captain hadn’t seen him in ages. It was genuinely touching for me to witness these old friends reconnect after years of being apart. Once again, I felt grateful to have these two quasi-dads in my life, full of wisdom and a dose of chicanery.

I am still wrapping my head around Rob’s passing. I’ve been seriously outdoor recreating for about a decade now, but had yet to experience losing someone to the wild — always a real possibility, but you never think these things will happen to you. As I set out on my long trail run this morning, I felt keenly aware of the risks I was taking as I ascended further into the woods through fog and rain. I had told some folks that I was going for a long run today, but I didn’t really specify where. Still, I felt compelled to keep getting after it, just as Rob always did.

The run ended up being the longest I’ve done in 9 months. Rob was on my mind the whole way — and the desire to write, as he did, was too. When I got home, I wondered if I could fix myself a little cup of chocolate.

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