For the people who call Breck home — for a weekend or a lifetime.
Hi! I’m Jake –
an engineer by training, a leader by experience, and a real estate investor by passion since 1999.
For over two decades I led growth and innovation in the software industry, serving as an executive at Cartegraph and Buxton. But I always had one eye on the built world — its potential for beauty, functionality, and the kind of design that makes a place feel like it was meant to exist exactly where it does.
Tomorrow River was born from that lifelong pull toward real estate and community. I grew up surrounded by it — my father was a land developer, my mother a broker — and I bring that heritage into every project. I've been actively investing and renovating properties since 1999, across the U.S. and Costa Rica, before going all in on Breckenridge. This town has everything I believe a great real estate market should have — four seasons of genuine demand, a community worth protecting, and people who love it enough to fight for it.
I created Tomorrow River to thoughtfully invest in Breckenridge. With a 360 degree view of everyone who calls this town home, from the locals who keep it running to the visitors who discover it for the first time. Every property we acquire is improved with intention and held for the long term, shaped by a design sensibility that honors the space rather than follows a trend.
This isn't just business — it's personal. It's about building something in a place I genuinely love, that contributes as much as it earns, and that I'm proud to put my name on.
Experience
Current Portfolio
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Short Term, Ski-in rental studio in downtown Breckenridge
TYPE: Fix + Hold
Purchase: $405k (2026)
Rehab: $35k (In-process)
Appraised ARV: $490k
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Rental duplex in downtown Breckenridge
TYPE: Fix + Hold
Purchase: $1.898M (2025)
Rehab: $500k (In-process)
Appraised ARV: $3.6M
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Vacation rental property in downtown Breckenridge.
PURCHASE: $600k (2017)
REHAB: $50k
MARKET VALUE: $1,100,000
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Long-term rental duplex in Carolina Place, near downtown, Wilmington.
PURCHASE: $350k (2021)
REHAB: $75k
MARKET VALUE: $575,000
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Iconic Surf Home of surfing legend Robert August (Endless Summer).
TYPE: Fix + Hold - Home + Attached Apartment
Purchase: $490,000 (2026)
Rehab: $50k (In-process)
ARV: $700,000
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Vacation rental property near town-center of Tamarindo.
TYPE: VR + RESIDENCE
PURCHASE: $107k (2019)
REHAB: $40k
MARKET VALUE: $275,000
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Workforce Housing Investment
INVESTMENT: $140k (2023)
OWNERSHIP: 28%
PROPERTY VALUE: $1,000,000
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Vacant land investment on Cherokee Lake in Morristown, TN.
PURCHASE: $29,000 (2023)
MARKET VALUE: $45,000
Past Assets
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TYPE: Agri-land Rental
PURCHASE: $120,000 (2018)
EXIT: $190,000 (2025)
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TYPE: Vacation Property
EXIT: 2025
SALE PRICE: $525,000
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Flip Project that was confronted by COVID, a bad contractor and STR regulations. Pivoted from flip to mid-term ski rental.
PURCHASE: $575k (2021)
REHAB: $500k
EXIT: $1,220,000 (2025)
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TYPE: Flip
PURCHASE/EXIT: 2024
PURCHASE PRICE: $305,000
REHAB: $80k
SALE PRICE: $430,000
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TYPE: LTR
PURCHASE/EXIT: 2022
PURCHASE PRICE: $473,000
SALE PRICE: $605,000
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TYPE: Vacant Land
PURCHASE/EXIT: 2021
PURCHASE PRICE: $127,000
SALE PRICE: $155,000
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TYPE: LTR
PURCHASE/EXIT: 2024
PURCHASE PRICE: $340,000
SALE PRICE: $680,000
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TYPE: New Construction Residence
PURCHASE/EXIT: 2020
PURCHASE PRICE: $365,000
SALE PRICE: $365,000
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TYPE: Flip
PURCHASE/EXIT: 2018
PURCHASE PRICE: $575,000
SALE PRICE: $945,000
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TYPE: STR
PURCHASE/EXIT: 2018
PURCHASE PRICE: $382,000
SALE PRICE: $550,000
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TYPE: LTR
PURCHASE/EXIT: 2021
PURCHASE PRICE: $125,000
SALE PRICE: $265,000
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TYPE: LTR
PURCHASE/EXIT: 2021
PURCHASE PRICE: $140,000
SALE PRICE: $265,000
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TYPE: New Construction - Residence
PURCHASE/EXIT: 2012
PURCHASE PRICE: $12,000
SALE PRICE: $255,000
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TYPE: Vacant Land
PURCHASE/EXIT: 2012
PURCHASE PRICE: $12,000
SALE PRICE: $30,000
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TYPE: New Construction - Residence
PURCHASE/EXIT: 1999
PURCHASE PRICE: $85,000
SALE PRICE: $150,000
