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.

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

People x Experiences

Instead of thinking only in terms of asset types, I think about who the home is for and how they want to live while they’re here.

I design and invest with three groups in mind:
- Vacationers – short stays, high expectations, experience-driven
- Part-time residents – second-home owners and seasonal users
- Locals – the people who live and work here year-round
Strong properties in Breckenridge often serve more than one of these groups over time.
Each property also fits into one (or more) lifestyle buckets:
- Walkable & Social
  Close to Main Street, dining, bars, shopping, and the town’s social energy
- Trail-Connected & Active
  Easy access to hiking, biking, skiing, and the natural playground that defines Breck
- Quiet & Scenic
  Privacy, peaceful surroundings, and long-range or mountain views
The best investments sit at the intersection of people and experience:
- Vacationers + Walkability → high-experience, short-stay friendly homes
- Part-time residents + Trail access → flexible, seasonally adaptable properties
- Locals + Quiet neighborhoods → durable, long-term living solutions
This framework helps guide:
- What I buy
- How I renovate
- How the property is used over time
- How risk and flexibility are managed
It’s not rigid—but it keeps decisions grounded in how Breckenridge actually works.

Investment Targets

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.

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

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.