Beyond the Algorithm: A life curated
A conversation with Becky and Michael Dumeresque on building a business legacy in the Roaring Fork Valley
Courtesy photo
Interview by Bryan Welker
For more than 30 years, Chequers has been more than just a home boutique in Aspen. It’s been part of the fabric of this town. The kind of place that locals and visitors alike return to again and again, not just for what’s on the shelves, but for how it feels to walk through the door. Since opening in 1992, Becky Dumeresque has shaped Chequers into something uniquely personal: a reflection of her background in fashion, her eye for design, and her deep love of community.
I sat down with Becky and Michael Dumeresque to talk about the road they’ve traveled, what it takes to grow a business that truly belongs in Aspen, and how they’ve managed to keep evolving without losing the character that’s made Chequers a local institution.
Q: For someone who’s never visited Chequers, how would you describe it?
Becky Dumeresque: Chequers is my vision. It’s a curated collection that reflects what I consider the Aspen lifestyle today. More contemporary now, but always personal. When people walk in, they often say, “This is what I want my house to look like.”
Q: How does that make you feel, hearing that?
Becky Dumeresque: Oh, it’s like applause! It really is. But for me, it’s not just about the compliment, it’s about what home means. Home is so personal. It’s where you gather with friends, entertain family, and unwind. It should reflect who you are as a couple, an individual, or a family.
But I don’t want your home to feel like my home. I want it to feel like yours. That’s why I love what I do: guiding people toward creating spaces that are authentically theirs. I want to augment what they have, what they’re looking for, and elevate it.
Q: What inspired you to start Chequers back in 1992?
Becky Dumeresque: It really came from two places: my family and my mentor. The tradition of decorating, designing, and enhancing our home was always part of my life. We did everything together as a family, from painting walls to hanging wallpaper. That hands-on experience shaped my love for home and design.
Then there was Lita Heller, who was my mentor and the queen of tabletop in Aspen. She had a store here called Special Occasions. One day she said to me, “Becky, why don’t you open your store?” That was the push I needed to take the leap.
Q: Aspen’s real estate market is known for its exclusivity and high demand. Could you share the story of how you successfully acquired your first property here?
Michael Dumeresque: Gerald Barnett was one of the first genuine connections we made when we arrived in town. We brokered the deal with Ernie Fryrwald, his son-in-law, who managed Aspen Sports at the time. We were standing in Ernie’s basement office when we finalized the details of our first lease — Gerald was on the other end of the phone. The agreement was simply written on a yellow legal pad. And we shook hands, and that was it!
Becky Dumeresque: And just to add to that, my mother was my not-so-silent “silent partner” at the time. She gave me an advance on my inheritance to help get Chequers started. It was $50,000 — can you imagine? Starting a business in Aspen on a shoestring feels impossible now, but back then, it’s what we did.
Q: The early ’90s were a special time in Aspen. If you could go back to that day, what would you say to your younger self before signing the lease?
Becky Dumeresque: What would you have said, honey?
Michael Dumeresque: It was the second-best decision of my life.
Becky Dumeresque: Oh, love that. I probably would have said, “Oh, sh–. Do I know what I’m doing?” But failure wasn’t an option. My mother had invested in my dream, and I wasn’t about to fail. No way! When your mom funds you, you have to succeed.
Michael Dumeresque: And yes, the financial stakes were huge, but Becky is being too modest. She was groomed by Lita Heller, who was the be-all and end-all of tabletop and home design in Aspen at the time. When Lita came to the end of her career and encouraged Becky to open Chequers, it was the passing of the torch.
Q: After all these years, what moment are you most proud of?
Michael Dumeresque: That we’re still here.
Becky Dumeresque: That really is it, isn’t it? And that the two most amazing and dedicated people who have been with us for over 25 years. Loyalty. We’ve built lasting relationships with our clients and our community. Some of them stop by just to say hello or have a glass of wine. We’ve worked on their homes, their children’s homes, and now even their grandchildren’s homes.
Michael Dumeresque: And we’re one of the last remaining family-owned businesses in the valley. That means the world to us.
Q: What do you believe is the most essential quality for someone working in retail in Aspen to succeed?
Becky Dumeresque: Passion and integrity.
Q: Has that quality been the key to your sustained success over the years?
Becky Dumeresque: Absolutely! You have to love what you do, and you have to love this community. I love what I do, and I do what I love. How many people can say that?
Q: What has it been like to balance building a thriving business in Aspen with raising a family?
Michael Dumeresque: It went hand in hand. Becky and I both come from a Southern heritage where family is the most important thing, and it is also the cornerstone of our life in the Aspen community. Building a business that essentially creates a home for families to live in, it felt like a natural and poetic progression.
Q: Aspen’s idyllic setting belies the challenges of running a business here. You mentioned overcoming a major setback with a business partnership — can you share more about that experience?
Becky Dumeresque: In 1994, I went into business with people I trusted completely. That trust was broken, and they embezzled millions. It took us years to truly overcome it. I felt like I lost a part of myself, a piece of my life. But eventually, together, we came out stronger. You know that old expression: What doesn’t kill you makes you stronger? That became our mantra.
Q: That must have been incredibly difficult. How did you make it through something so devastating?
Michael Dumeresque: It proved our commitment to a) our family, and b) our business.
Becky Dumeresque: We put everything we had into it. We worked our butts off to protect the dream and to keep our family business alive. And here we are, 21 years later, standing taller than ever.
Q: With the rise of luxury franchise brands in Aspen, what strategies or qualities are essential for a small, independent store to thrive?
Becky Dumeresque: Reputation, excellent customer service, and client relationships.
Michael Dumeresque: I agree.
Becky Dumeresque: Looking out for people. It’s not about us; it’s about the customer, the community, and our employees. You can’t survive in this town without integrity.
Q: How has Chequers woven itself into the fabric of the Aspen community over the years, particularly through local engagement and support?
Becky Dumeresque: When we started, the town was all local businesses. We were part of the fabric of the community. We donated to silent auctions, fundraisers — whatever people needed, we showed up. And it wasn’t just us; everybody did that. There wasn’t the internet or Amazon then. People shopped local, ate local, and lived local.
Q: Why is shopping local still important for supporting Aspen’s community and economy in today’s market?
Becky Dumeresque: Because it keeps the community alive. When you shop local, you’re supporting Aspen!
Q: What lasting impact do you hope Chequers will leave on the Aspen community?
Becky Dumeresque: I hope people remember that they had fun being here with us. We’ve had clients for decades, and now we work with their kids and grandkids. That’s special. Aspen is family to us. We have Thanksgiving dinner with whoever needs a place to go. That’s the spirit of this town.
Q: What’s your favorite thing about Aspen?
Becky Dumeresque: I don’t know… what isn’t?
Michael Dumeresque: The Ute Indians would say, “Take a look around you.”
Becky Dumeresque: That’s it. Take a stroll around town and say hello to a stranger or a familiar face. Walk up the mountain, drink the water — it’s all got the magic in it!
The Dumeresques have created more than a boutique. In their own quiet way, they’ve bottled a bit of Aspen’s magic and made it feel like home.
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. If you know a businessperson we should interview, please reach out!
