Chris Flynn on Real Estate, Growth, and What Comes Next.
Interview by Bryan Welker and Stefan le Roux | For The Aspen Times
When Chris Flynn first came to the Roaring Fork Valley in 1997, Aspen was not part of a long-term plan. It was simply a place he passed through—until it wasn’t. What began as a weekend visiting a close friend turned into a simple, stubborn resolve: if he could find the basics, a job and a place to live, that would be enough. With little more than that in mind, and few certainties beyond his desire to be here, Flynn chose to make the move anyway.
Nearly three decades later, Flynn is a managing partner at The Agency Aspen, having built one of the longest and most consistent real estate careers in the valley. His story mirrors Aspen’s own evolution—from a small, relationship-driven town to one of the most competitive real estate markets in the world.
Bryan: What’s your Aspen story? How did you end up here?
Chris:
Oddly enough, it started with a visit. I came up to see my buddy Darren Hodgson, who sadly passed away recently. We had an absolute blast that weekend. On my way out of town, I called my cousin, who lived in Basalt, and told him how much I loved it here. I said, “If I could get a place to live and a job, I’d move.”
By the time I got back to Denver, they had both lined up—a job at Keelty Construction and a place to live in a trailer park in Woody Creek. That was 1997.
Bryan: What was Aspen like then?
Chris:
I didn’t know anyone except Darren and my cousin. I was doing straight labor—construction work—and slowly met people through friends. After a few years, I realized that if I wanted to stay, I had two realistic options: the service industry or real estate.
I got my real estate license in 1999 while working four or five other jobs. It took a good year and a half, maybe two years, before I could make real estate my main focus.
Bryan: Who did you first work for?
Chris:
The first brokerage was Herron Korn & Company, which isn’t around anymore. Then Country Village Rentals and Real Estate, and later Morris & Frywald. I learned a lot from Craig Morris and Ernie Frywald—they were, and still are, titans in this market.
Bryan: You eventually helped build Aspen Associates. What did those years teach you?
Chris:
We started it as a development, investment, and real estate company, and the real estate side really took off. I spent about 14 years there, and it taught me the business inside and out.
Running a company means constant decision-making, solving problems daily, and balancing that with managing your own clients. I loved that part of it—the operational side and the client side together. Even today, that’s what keeps the work interesting.
Bryan: People underestimate how complex real estate deals are here. Why is that?
Chris:
The easy deals are few and far between. We’re marriage counselors, family counselors, and often the bridge between clients, architects, builders, and municipalities.
Many clients come from different states or countries, where the process is completely different. A big part of our job is education and hand-holding. I see my clients as teammates—we work through it together.
Bryan: What makes a good broker in Aspen?
Chris:
This is one of the most competitive markets in the world. You don’t just get a license and start selling property and expect it to fall into your lap. You’re competing with people who have been here for decades, who know the inventory, the history of the homes, the zoning, the players, and the nuances of every neighborhood.
The brokers who do well are available, they’re prepared, and they’re constantly learning. Not everyone succeeds—even some very capable people don’t—but the ones who take it seriously, who put in the hours and commit to the long game, give themselves a much better chance in a market like Aspen.
Bryan: You joined The Agency just before COVID. That timing must have been unnerving.
Chris:
It was December 2019 when I officially joined. A few months later, COVID hit, and I thought I’d made the biggest mistake of my career.
Then the opposite happened. Business exploded. People reassessed their lives, left cities, and prioritized lifestyle. We became conduits—showing people what Aspen and the valley offer. Prices took off, and it’s still reverberating today.
Bryan: Where do you see the market right now?
Chris:
Things have stabilized in a healthy way. Transactions are happening. It’s harder for people to make lateral moves because of price increases, but overall, the market feels balanced.
Aspen, Snowmass, Basalt—it all reverberates. People cash out of Aspen and move down valley. That trend isn’t going away.
Bryan: Snowmass and Basalt have seen major growth.
Chris:
Snowmass benefited from new product—ski-in, ski-out inventory that Aspen simply doesn’t have much of anymore. The base village development filled a real gap.
Basalt has evolved into a true community. Prices are higher than anyone would’ve imagined a decade ago, but the town has done a great job managing growth while preserving character.
Bryan: What challenges do you see heading into 2026?
Chris:
Inventory is opening up slightly, which is healthy. One challenge is that sellers don’t always need to sell, and buyers don’t always need to buy—that stretches timelines.
City fees and redevelopment costs remain a hurdle, but there’s a balance there. Regulation preserves open space and character, which is why this valley is so special. There are pros and cons.
Bryan: What advice would you give a young person considering real estate?
Chris:
I believe in education. College is a life experience, whether you use it directly or not.
If someone is serious about real estate, they need to understand it’s not an overnight success. It’s hard work, seven days a week.
I’d suggest getting licensed and working under an experienced broker. You’ll learn contracts, negotiations, marketing—everything you need to eventually build your own business.
Flynn’s career reflects the reality of Aspen real estate—built slowly, sustained through discipline, and shaped by constant change. As the valley continues to evolve, his perspective underscores a simple but important truth. Success here isn’t accidental. It’s earned.
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
