Beyond the Algorithm: The business of fun 

Depending on the setting, Chris Davenport might describe his career in a number of ways, but if he had to distill it into a single phrase, he would probably say: professional risk manager. 

Over decades in the mountains — from early big mountain competitions to guiding on peaks like Everest — Davenport has built a career around managing risk with precision. What began as a simple goal to ski every day has become a life shaped by discipline, calculation and longevity. 

Bryan: When someone asks what you do, what do you tell them? 

Chris: It depends where I am. On an airplane, I might say I’m a professional risk manager. On the mountain, I might say I’m a guide. In town, I work in the ski industry. I wear a lot of hats — guiding, product development, working with brands, running trips and camps all over the world. There’s no single answer. 

Bryan: Did you plan this life? 

Chris: The only thing I planned was to ski every day for the rest of my life. I remember being a kid in New Hampshire, maybe 13 or 14, skiing on a powder day and thinking, wouldn’t it be amazing if you could just do this forever? That idea stuck. 

After college, I moved to Aspen and started working in the ski industry. I realized pretty quickly I was actually doing it — skiing every day. Then I got pulled into the early freeskiing scene, started competing and within a couple of years I was making a living doing it. That part wasn’t planned, but it worked. 

Bryan: For readers who might not know, what is freeskiing? 

Chris: It came out of what used to be called extreme or big mountain skiing. Instead of gates, you’re given a face with cliffs and terrain, choose your line and are judged on speed, control and style. It started in the early ’90s, and I got into it right at the beginning. 

Bryan: Were you scared? 

Chris: No. I wasn’t scared — I was calculated. Ski racing teaches you how to commit. I think early on I was a bit naive about the risks, but that changed quickly. I started making ski films, traveling, seeing avalanches and losing friends. You realize pretty fast how dangerous it is. 

Now, 35 years later, I’m focused on longevity. I went through that gauntlet in my 20s and 30s. These days, it’s about continuing to ski, but doing it conservatively. 

Bryan: Where does fear fit into that? 

Chris: If fear creeps in, it probably means you haven’t done your homework, or you’ve missed something. By the time I’m standing on top of a line, I’ve already done the calculus. I know what I’m about to do. 

Bryan: When I played football, time would slow down when I got the ball. Does that happen to you? 

Chris: Yeah, that’s the flow state. You’re completely focused. In the mountains, you’re thinking about the terrain, the snow, the weather, your line, your partners. There’s no distraction. You’re just in it. 

Bryan: Does that mindset translate to business? 

Chris: Definitely. In the mountains, you’re constantly managing risk to get the best outcome. In business, it’s the same thing — market conditions, competition, financial risk, reputational risk. 

I often use guiding a client on Everest as an example. You have a plan, but conditions change, so you adapt. Every decision is about improving your chances of success while managing downside risk — no different from running a business. 

Bryan: Can you talk about the ecosystem of business around skiing? 

Chris: Aspen runs on skiing — fueling everything from retail and hospitality to real estate. I call what I do the “business of fun.” Whether it’s guiding, designing products or running trips, it’s about giving people experiences — helping them grow, push themselves and enjoy life. 

Bryan: What’s your exit plan? 

Chris: I don’t have one. Why would I? If your work is your passion, there’s nothing else you’d rather do. I’ll be skiing at 65, 75, hopefully 85. I just want to keep doing it. 

Bryan: What does staying fit mean to you now? 

Chris: It’s a mindset. I don’t walk upstairs — I run them. I don’t ski casually — I ski hard. I’m always thinking about training, nutrition and staying healthy. It’s just part of how I live. 

Bryan: What worries you about the future of the industry? 

Chris: Snow. This year is one of the worst we’ve seen. Snowpack is our reservoir — no snow means no water, and it affects everything: tourism, restaurants, retail. 

One bad year is manageable. Three or four in a row? That’s a different story. It’s happening globally — shorter seasons, less reliable snowfall. It’s the biggest existential threat we have. 

Bryan: What keeps Aspen special? 

Chris: The community. People make sacrifices to live here because the lifestyle is so good. You give up certain things, but you gain something else — access to the outdoors, strong relationships, a sense of place. 

It’s easy to complain, but I try not to. We get to wake up every day and choose how we spend it. That’s pretty rare. 

Bryan: What advice would you give a 20-something who wants to build a life like yours? 

Chris: Don’t feel pressure to chase something you don’t love. Life goes by fast. 

If you love skiing, come here, figure out a way to be on the mountain every day. Maybe you won’t make a fortune — but your life will be rich in experiences and relationships. And those are the things that actually last. 

In Aspen, where lifestyle and livelihood are inseparable, Davenport’s perspective is simple: know what you’re optimizing for, do the calculus before you commit and build a life you don’t want to step away from. 

Bryan Welker lives and breathes business and marketing in the Roaring Fork Valley and beyond. He is President, Co-founder, and CRO of WDR Aspen, a boutique marketing agency that develops tailored marketing solutions. Who should we interview next? Reach out and let us know bryan@wdraspen.com.