Tomorrow River

Welcome to

A real estate investment company focussed exclusively on Breckenridge, Colorado.

I’m Jake.

I'm 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.

WHY BRECK

Focussed on One Place

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.

Breckenridge sees consistent, year-round demand driven by two peak seasons and millions of annual visitor days tied to recreation and recurring events. This demand is structural, not speculative, and repeats reliably over time.

Visitor Demand

Breckenridge’s housing supply is tightly constrained by geography, public land, and zoning, making new development slow and costly. As a result, most future housing will come from existing buildings rather than large-scale new construction.

Supply Constraints

Breckenridge depends on both visitors and a local workforce, creating ongoing pressure between short-term use and housing for residents. Long-term ownership helps balance these needs and supports the town’s ability to function over time.

Housing Tension

INVESTMENT PHILOSOPHY

Place-Based Ownership

Tomorrow River is built on the belief that the best long-term real estate investments come from deep commitment to a single place. Rather than spreading capital across markets, we focus exclusively on Breckenridge, Colorado—a town with enduring demand, natural constraints, and a community shaped by both locals and visitors. This focus allows us to invest with clarity, patience, and conviction.

Our philosophy is rooted in place-based ownership. Breckenridge works because it serves many people at once: full-time locals who keep the town running, part-time residents who return year after year, and visitors who sustain the local economy. A resilient portfolio reflects that balance. We invest intentionally across this full spectrum, recognizing that long-term value is created not by optimizing for a single use, but by supporting the ecosystem as a whole. At the portfolio level, we invest across Breckenridge’s distinct living experiences—what we think of as the town’s natural rhythm:

Walkability — properties near the town core that connect directly to social life, dining, culture, and community.
Accessibility — homes that provide efficient access to trails, skiing, biking, and the outdoor infrastructure that defines Breckenridge.
Seclusion — quieter settings that prioritize privacy, peaceful surroundings, and long-range mountain views.

Each experience serves a different need. Together, they create diversification across seasons, demand cycles, and renter profiles—while reinforcing the character of the town itself.

At the property level, Tomorrow River invests with engineering discipline and design intention. We look for assets with strong fundamentals but untapped potential—often unlocked through thoughtful layout changes, durability upgrades, or design moves that improve how a property functions and feels. We prioritize practical sustainability, long-term livability, and improvements that age well over time.

This is not a high-velocity or trend-driven strategy. It is a long-term ownership model built on local knowledge, trusted relationships, and disciplined execution. Our goal is to compound value steadily, generate consistent returns, and build a Breckenridge-only portfolio that performs across market cycles—while contributing positively to the place we’ve chosen to invest in for the long run.

INVESTMENT FRAMEWORK

People × Experience

A resilient Breckenridge portfolio is built by investing across who the town serves and how people experience it. Tomorrow River aligns properties at the intersection of People and Place-Based Experience to create diversification, durability, and long-term relevance.

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 River invests across all three—not to dilute focus, but to create balance.
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.
- 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.

A table comparing three types of housing: Walkable + Social, Nature-Connected, and Quiet + Scenic, across three resident categories: Visitors, Part-time Residents, and Local Residents. Each cell contains descriptions of housing features tailored to each category, such as walkability, proximity to amenities, outdoor access, seasonal recreation, architectural style, privacy, and neighborhood integration.

INVESTMENT TARGETS

3P-Portfolio

I invest exclusively in Breckenridge, 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.

Long-term rental homes that provide durable, well-maintained housing for people who live and work in Breckenridge.

Residential Rental

Vacation Rental

Thoughtfully operated short-term homes that allow visitors to experience Breckenridge while coexisting responsibly with the community.

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

Mobile Home Park

Long-term housing that provides a practical and attainable living option for local residents in a high-cost mountain market.

Self Storage

Practical storage facilities that support residents, businesses, and seasonal living in a mountain environment.

Current Project

High Street 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.