Cowboy Frontier Fund
Institutional-Grade Short-Term Rental Investing
in Jackson Hole
A $30M fund acquiring, renovating, and operating showcase short-term rental properties across Jackson Hole, then exiting after a disciplined hold period — underwritten and executed like a real estate private equity firm.
The Strategy
How It Works
Most owners simply buy a property and rent it out. Cowboy Frontier underwrites and executes a full value-creation plan on every asset before it ever enters the rental pool.
Buy
We source and underwrite Jackson Hole properties below market, applying the same acquisition discipline as a real estate private equity firm.
Renovate
Self-managed construction and direct trade relationships turn a purchase into a showcase property, on a timeline outside buyers can't match.
Reposition
Each property is repositioned as a premium short-term rental, designed and finished to compete at the top of the Jackson Hole market.
Maximize NOI
Professional STR operations drive revenue and net operating income well beyond a typical owner-operated rental.
Refinance or Exit
After the hold period, we refinance to return capital or exit the asset outright, closing the value-creation cycle we underwrote from day one.
For Rental Pool Owners
The 1031 Opportunity
If you already own a property in Cowboy's rental pool, you may have the opportunity to 1031-exchange that property into Cowboy Frontier. Rather than your returns being tied to a single property's performance, you'd participate in pooled distributions across the fund's full portfolio of showcase Jackson Hole rentals.
This is a directional overview, not tax or legal advice. Every owner's situation is different — talk to your advisor, and then talk to us about whether an exchange into the fund makes sense for you.
Talk to Us About Your PropertyThe Numbers
Investment Criteria
5–15%
Purchase Discount Below Market
$100–350/SF
Rehab Budget
3 Years
Target Hold
65–70%
Leverage (LTV)
20%+
Minimum Levered IRR
2.25x+
Minimum Equity Multiple
8%+
Minimum Cash-on-Cash
3.75–4.50%
Exit Cap Rate
Our Edge
The Cowboy Advantage
Cowboy creates value through construction execution, not just market appreciation. Every advantage below comes from running renovations in-house, not outsourcing them.
Contractor Pricing
5–10% cost savings versus market-rate general contracting, built directly into every renovation budget.
Self-Managed Construction
3–5 months faster delivery than outsourced GC oversight, getting properties to market sooner.
Local Trade Relationships
Established Jackson Hole trade partners reduce scheduling risk on a market with a short, competitive build season.
Matterport Documentation
Full 3D documentation of every property improves due diligence and digital closeout for investors.
Bluebeam Coordination
Digital plan coordination across trades means fewer change orders and fewer surprises mid-build.
AutoCAD / BIM
In-house design capability allows faster iteration on layout and finish decisions before construction starts.
Local Vendor Network
Direct relationships with Jackson Hole vendors and suppliers translate to better pricing and procurement.
Discipline
Institutional-Style Underwriting
Every opportunity goes through an Investment Committee-style scoring process before it enters the fund, evaluated across the categories that matter most to long-term performance.
- Acquisition Price
- Renovation Opportunity
- STR Revenue
- Construction Risk
- Exit Potential
- Liquidity
Market Context
A Resilient Market
Jackson Hole continues to be one of the strongest short-term rental markets in the country, backed by limited housing supply, protected land, and year-round demand from visitors to Grand Teton and Yellowstone National Parks.
Request Investor Info
Reggie Benz, Founder & Managing Partner of Cowboy State Capital, is based in Jackson Hole, Wyoming and personally leads every conversation with prospective Cowboy Frontier investors.
Get in Touch