Lessons from 25 Years in Aspen: Building Trust Through Authentic Marketing

After 25 years navigating Aspen’s unique marketing landscape, I can tell you one thing for sure: authenticity still wins. Always has. Always will.

In a town where algorithms might point you toward flashy digital ads, it’s the human connections, forged through genuine storytelling and community trust, that keep people coming back.

At WDR Aspen, I’ve helped businesses craft campaigns that resonate with everyone from jet-setting visitors to lifelong locals. So here are five hard-earned lessons to help your business stand out in the Roaring Fork Valley, no algorithm required.

1. Know Your Audience Intimately

True to Aspen, your customers range from wealthy second-home owners, lifelong locals, seasonal snow shredders, summer hikers chasing wildflowers, and probably a few characters I forgot to mention. You get the idea.

So, how do you connect with all these different folks in a way that feels real? Easy answer: listen more than you talk. Then tailor your message to what they actually care about.

People come to Aspen for many reasons. Some crave high-end exclusivity, while others seek adventure or a tight-knit community. Understanding which of those emotional threads ties into your business is key. Maybe you’re a boutique that curates exclusive craftsmanship, or a local café where grabbing the Aspen Times with your morning coffee is part of the ritual.

It’s about understanding your customer, and this starts with listening to them in person, not just analyzing the data. Treating your customer like a person, and not a metric, helps you understand their motivation.

And once you understand their motivation? Well, you can show up the way they need you to, when they need you to and that’s what keeps them coming back.

2. Make Aspen a Part of Your Brand Story (because it is)

Calling Aspen home isn’t something to take for granted. Aspen’s history, natural beauty, and cultural cachet aren’t just backdrops for your business; they’re some of the most powerful tools you’ve got in your marketing kit.

Understanding how special this place is and finding ways to incorporate authentic elements into campaigns helps create emotional resonance. The trick? It needs to resonate with you and your business before you try to resonate with your audience.

Use compelling storytelling to tie your business to Aspen’s identity. Aspen is a story in itself, and as a business, you’re a part of that story. So, let me ask you. What is your role in this slice of paradise we call home? How do you want to play your part? That’s the message to your customers.

Don’t just tell people how awesome Aspen is; feel it, and live it. You can have the best marketing strategy out there, but if you don’t feel Aspen in your bones, your customers won’t either.

3. Build Relationships, Not Just Transactions

This comes back to the point I made earlier about people being people, not analytics and boring metrics. Sure, it sounds simple enough. And you might think “hey, that ain’t me”. But when you’re caught up in the daily grind, it can be way too easy to forget that if you’re solely focused on the numbers.

I hold myself to this, too. I make it a point to honor the relationships I’ve built over the years and appreciate the connections I’ve built along the way, whether it’s swapping stories with Dusty on the top of Tiehack on a Monday morning or chatting with the crew at Aspen Snowmass Sotheby’s International Realty about everything from skiing to real estate.

Here’s the simple truth: in a small town like Aspen, word-of-mouth and personal connections aren’t just nice to have; they’re the heart of success. Over the years, from working with Habitat for Humanity, the ReStore, TACAW, and other local nonprofits, plus plenty of elbow grease in local networking, we’ve learned one thing loud and clear: community connection matters.

The trust you build by showing up for your town is the very same trust folks bring through your door. So don’t just do business here. Be part of the community. Sponsor events, support nonprofits, and do it with genuine care. When you put your heart into it, the yield is lasting relationships that stand the test of time.

4. Balance Digital and Traditional Marketing

Our experience at WDR ASPEN proves time and time again the power of local media. If you’re skipping the good ol’ traditional playbook in Aspen, then you’re missing out.
The affluent crowd here? They still respect and respond to traditional marketing. There’s a pride in that, and honestly, it’s a privilege to carry the torch. After all, it’s where my journey began.

Traditional marketing means real, tangible touchpoints with your local crowd. Whether it’s a well-placed print ad or a slick piece of direct mail, pairing those physical moments with a killer digital game plan is how you cover all your bases. Think targeted social media mixed with high-quality print that people can hold in their hands.

And don’t forget your GBP, that’s your Google Business Profile. It’s a local business secret weapon, especially when combined with an experimental event or a feature in a good magazine. They work hand in hand (when done well).

Aspen’s audience is diverse, and the winners are the ones who play a balanced marketing game with both solid digital presence and authentic, tangible connections.

5. And Finally… Adapt to Seasonality with Creativity

This tip is short and sweet. Aspen has seasons like it has ski runs; some fast, some slow, and you’ve got to know how to work both. In a boom-or-bust seasonal economy, you need to incorporate flexible marketing. The businesses that thrive embrace strategy pivots during off-seasons and plan campaigns that capitalize on shoulder seasons.

The trick? Embrace creative thinking here. Don’t just ride on the shoulder seasons; be smart about how you use them to your advantage and hone in on the details that matter in the off-season. Lean into the quiet months, lean into your community. That’s where the magic (and margins) happen!

Remember, marketing can open the door, but it’s authenticity that gets you a seat at the table, preferably one with a view of Ajax. Let people feel Aspen through your brand. In this valley, if you fake it, they’ll spot it faster than a Texas license plate at the start of ski season.

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.

Jessica Rosslee

Jessica Rosslee

Content Manager

Aarav blends business acumen with poetic storytelling. With a decade of experience in luxury branding, he’s known for crafting narratives that evoke trust, aspiration, and timeless elegance.

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