Tomorrow
Investment Group
Tomorrow is a family-run real estate investment group focused exclusively on Breckenridge, Colorado—building and holding well-located properties with a long-term mindset.
Our strategy is rooted in a simple belief: the best outcomes—for the town, its people, and our investors—comes from committing to one place and knowing it well. Instead of spreading capital across multiple markets, we focus entirely on Breckenridge—a town shaped by steady demand, limited supply, and a mix of locals and visitors who give it life. That focus allows us to invest with patience, clarity, and long-term conviction.
Breckenridge combines 9,600-ft elevation, four-season recreation, and a walkable town core—an uncommon mix among mountain towns–and the perfect combination of Place + Demand.
Why Breckenridge
Visitor Demand
Consistent, year-round demand driven by recreation, events, and repeat visitors.
Supply Constraints
Limited land and strict zoning keep new supply low and scarce.
Housing Tension
Ongoing pressure between visitor use and local housing needs.
People × Experience
A resilient Breckenridge portfolio is built by investing across who the town serves and how people experience it. Tomorrow aligns properties at the intersection of People and Place-Based Experiences– creating diversification, durability, and long-term relevance.
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Breckenridge functions because three groups coexist and reinforce one another. Each plays a role in the town’s economy and culture:
Locals
Full-time residents who keep the town running—workforce, families, entrepreneurs, and long-term community members.Part-Time Residents
Seasonal and second-home owners who return consistently, invest emotionally in the town, and support local businesses year after year.Visitors
Short-term guests who fuel tourism demand, support the service economy, and introduce new people to Breckenridge.
Tomorrow invests across all three—not to dilute focus, but to create balance.
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Where and how a property connects to Breckenridge defines its role in the portfolio:
Walkability
Proximity to Main Street, dining, social life, and community hubs. Prioritizes convenience, connection, and vibrancy.Accessibility
Efficient access to trails, skiing, biking, and year-round recreation. Prioritizes movement, activity, and connection to nature.Seclusion
Quieter settings with privacy, peaceful surroundings, and long-range mountain views. Prioritizes retreat and restoration.
Each experience responds to a different emotional and functional need—across seasons and life stages.
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Portfolio Construction
We intentionally want to own across multiple intersections to balance seasonality, renter profiles, and demand drivers.Risk Management
Diversification is achieved through place-based experience, not geographic sprawl.Value Creation
Design and layout choices are informed by how each property fits its specific People × Experience role.Long-Term Alignment
This framework supports a healthy mix of uses that strengthens the town rather than optimizing for a single outcome.
Investment Targets
We’re building a place-based portfolio that supports how people live, work, and spend time here. Focusing on one town allows for deeper understanding, thoughtful decisions, and long-term ownership aligned with the rhythms of the community: Visitors, Part-time Residents and Locals.
Mid and Long-term rental homes that provide durable, well-maintained housing for people who live and work in Breckenridge.
Residential Rental
Thoughtfully operated short-term homes that allow visitors to experience Breckenridge while coexisting responsibly with the community.
Vacation Rental
Commercial Retail
Small-scale retail spaces that serve everyday needs and contribute to an active, walkable town core.
Intimate, well-designed lodging that offers a consistent, place-rooted experience without the scale of large resorts.
Boutique Hotel
Housing structured to support the local workforce, helping people who make the town run live closer to where they work.
Workforce Housing
Long-term housing that provides a practical and attainable living option for local residents in a high-cost mountain market.
Mobile Home Park
Practical storage facilities that support residents, businesses, and seasonal living in a mountain environment.
Self Storage
I’m Jake –
an engineer by training, a leader by experience, and a real estate investor by passion. After more than two decades leading growth and innovation in the software industry, I focused my work on the built world—investing in and renovating properties across the U.S. and Costa Rica since 1999. Today, I invest exclusively in Breckenridge, Colorado, applying engineering discipline, thoughtful design, and long-term ownership to build a durable, place-based portfolio that performs across market cycles and contributes positively to the community.
Current Project
High St Duplex
Tucked into the 100 block of South High Street—just a short stroll from downtown Breckenridge—this 1975 mansard-roof duplex stands as both an outlier and an opportunity. With nearly 4,000 square feet of space and a front-and-back unit layout, the property sits within the town’s historic district, where charm, cohesion, and thoughtful design matter.
Over the years, this home has become one of the more overlooked properties on the street. But we saw something else: untapped character, architectural potential, and a chance to write a new chapter. Our goal is to respect the home's 1970s roots while refining and modernizing the structure so it better complements its surroundings. That means softening the harder edges, bringing warmth and life to the exterior, and creating interiors that reflect both mountain heritage and elevated livability.
This project is more than just cosmetic; it’s a careful balance between preservation and progression. By giving this building a new identity—one that honors its past and integrates into the present—we're proving that sustainability isn’t just about materials… it's also about mindset. Through the Ecoheirloom lens of beautiful, functional, and sustainable, we're transforming this once-forgotten home into something quietly extraordinary.
