For the inaugural Aspen Business Connect luncheon, we had the privilege of having lunch with a deeply respected leader in our valley, Dwayne Romero. Held at Gravity Haus Aspen, this gathering brought together 30 community members to share ideas, and inspiration around Roaring Fork Valley leadership, service and mentorship.
Dwayne Romero’s resume alone speaks volumes. A West Point graduate and decorated Army veteran, he went on to earn his MBA from Harvard and lead major development projects through firms like Hines, Related, and now The Romero Group, which he co-founded. The Romero Group manages over 65 HOA communities, 125,000+ square feet of commercial property, and employs over 120 people across the valley. He has also held high-ranking public service roles, including a cabinet-level position under former Colorado Governor (now Senator) John Hickenlooper, and two terms on Aspen’s City Council.
But what left the deepest impression on everyone in the room wasn’t his long list of accomplishments, it was his humility, values, and genuine commitment to serving others.
On Leadership
Dwayne opened the conversation by reflecting on leadership, not as a title, but as a responsibility. Whether you’re running a business, coaching youth sports, or mentoring someone just starting out, true leadership requires showing up with discipline, humility, and purpose. “When you’re firefighting, you’re not looking down the road, you’re looking at what’s right in front of you” he said.
On Mentorship
Drawing from his own journey, and that of his colleagues, Dwayne spoke to the powerful ripple effect of mentorship. He referenced Dave McCormick’s book Who Believed in You: How Purposeful Mentorship Changes the World? to reinforce how deeply mentors can shape lives. His own interns have gone on to top universities, and many of the young men he coached in baseball still carry the character lessons he instilled. He emphasized how being a mentor can often be just as or more rewarding than being a mentee. “You’re not just helping an individual,” he said. “You’re supporting a family and a community.”
On Housing & Workforce Challenges
The conversation naturally shifted toward one of the region’s most urgent issues: housing affordability and workforce retention. Dwayne and other guests, including Mike Mercatoris, shared bold ideas and active solutions, from down payment assistance programs to employer-funded housing models.
Mercatoris detailed a visionary project he helped design with Gail Schwartz, President of Habitat for Humanity and former Colorado State Senator. He brought the model to Dave Portman, Market President of FirstBank, so that they could offer free-market units repurposed for affordable homeownership without any government funding.
For small businesses, the message was clear: tap into local programs like Glenwood Springs’ down payment assistance initiative or creative public-private partnerships that allow employers to help staff stay and thrive here.
These Aspen Business Connect luncheons are more than just meals, they’re catalysts for connection, collaboration, and action. Each month we will be gathering remarkable individuals who have been stewards of our valley or are working on commendable projects to help shape the future both locally and globally, one conversation at a time.
Our next guest at the table on May 29th is Caroline Tory, Managing Director of Aspen Words, one of the nation’s leading literary centers and a program of the Aspen Institute. With a rich background in nonprofit leadership, fundraising, and literary programming, Caroline has been instrumental in growing Aspen Words into a nationally recognized organization that amplifies diverse voices and fosters the power of storytelling. She is also a competitive endurance cyclist and ski mountaineering athlete, racing events ranging from the Life Time Grand Prix off-road series to the Power of Four.
Guests will have the opportunity to ask Caroline questions on literature and storytelling, especially in a time where authentic connection and empathy are more important than ever. Caroline will also share her insights into endurance training and how the two can be intertwined.
If you’re seeking meaningful dialogue, authentic community, and a seat at the table with those moving the needle in the Roaring Fork Valley, we invite you to join us. Space is limited so don’t wait. Click here to purchase your ticket and get closer to those making a difference in our valley, or better yet, become an Aspen Business Connect member and get in deeper with a network who believes in the power of service and building community.
