01
Hub-Guesthouse Network
Stay, Together™
67%
of all travel involves booking 2+ rooms—yet zero dedicated, scalable solutions exist

Investment Memorandum · February 2026

An Asymmetric Opportunity in Luxury Group Hospitality

High-net-worth group travel in supply-constrained lifestyle markets. Real estate collateral enables a safe position for OpCo venture upside.

As Featured In
Forbes Travel + Leisure Veranda Hospitality Design Skift
$6M
Capital Raise
$11M
Property Value
1.8×
Asset Coverage
8-10×
Platform Exit Multiple
SKIFT The Leading Voice in Travel Industry Intelligence

"Guesthouse, a new collection of members-only rental houses that combine the comforts of a luxury home with the amenities of a boutique hotel, combines all of the above to form an entirely new category in the evolving hospitality landscape... Guesthouse leads the way with personalized, hotel-level service; elevated interior design; curated destinations; and a members-only model."

Skift is the most respected publication in travel, read by executives across airlines, hotels, and tourism boards worldwide

The Stripe Thesis
Private & Confidential Guesthouse Companies
02
The Company

Premier Destinations for Purposeful Gatherings

The privacy of home meets the amenities of a boutique hotel

Guesthouse is a premier collection of members-only destinations for personalized group stays and bespoke retreats. With the warmth of home and the amenities of a boutique hotel, we offer design-driven spaces that inspire creativity, collaboration, and meaningful gatherings.

Personalized hospitality is our hallmark: in-home meals from a private chef, curated partnerships with local restaurants, gold passes to Tahoe resorts, private transportation, and a dedicated 24/7 house captain.

Audience Segments:
Multi-Gen Families Corporate Leaders Creative Professionals Affluent Leisure Travelers
Design Partners: Ryan Group Architects · Halfdan Pedersen · Olympia Pearl Design · Michael Hsu Office of Architecture
Guesthouse Lake Tahoe
Campus #1
$2,887
AADR
4,200
Square Feet
10
Guests
Palm Springs Manor
Coming Q1 2026

Campus #2 · 19 Units · Desert Seasonality

Complementary Seasonality 85%+ combined annual occupancy
J
F
M
A
M
J
J
A
S
O
N
D
🏔️
Lake Tahoe
Mountain · Ski & Summer
🌴
Palm Springs
Desert · Winter Escape
Combined
Peak Season High Season Shoulder Off-peak
Private & Confidential Guesthouse Companies
03
The Team

Experienced Leadership, World-Class Partners

Operators with exits, strategic partners with global recognition

TC

Trevor Cornwell

Founder & CEO

Serial entrepreneur with exits to Bombardier (Skyjet) and Intel Capital (appbackr). Johns Hopkins graduate. Family legacy in boutique hospitality through father Anthony Cornwell's work at Needham & Grohmann creating branding for Laurance Rockefeller's RockResorts.

MG
Marta Gawlowicz · Hospitality Head
15 years hospitality. USHG-trained.
QF
Quinten Frye · Executive Chef
James Beard semi-finalist.
DA
Doug Appleton · GP, Lake Tahoe
Truckee development expert.
HP
Halfdan Pedersen · Design Director
Brand aesthetics lead.
Operations
Union Square Hospitality Group Danny Meyer's organization. "Enlightened hospitality" training.
Architecture
Bjarke Ingels Group (BIG) Google Bay View, 2 World Trade Center.
Press
Travel + Leisure "Guesthouse bridges the gap between boutique hotels and rental houses."
Private & Confidential Guesthouse Companies
04
Recommended Structure

Secured Convertible Note

Real estate security with equity upside

Term Sheet Summary

InstrumentSecured Convertible Note
Principal$6.0M
Interest10% simple, accruing
Maturity36 months
Conversion Discount20%
Valuation Cap$8M pre-money
SecurityCross-collateralized RE

Capital Stack Post-Financing

Horan HouseBank Construction$1.85M @ ~8%
Titus House100% EquityPaid
Palm Springs ManorSeller Financing$2.375M @ 5.0-5.5%
Hybrid InstrumentSecured Convertible$6.0M → Equity
Private & Confidential Guesthouse Companies
05
Return Scenarios

Asymmetric Risk-Reward Profile

Floor protected by real assets, ceiling defined by platform scale

Scenario
What Happens
Returns
IRR
Downside
OpCo fails; RE liquidation
$6M + accrued (1.0-1.3×)
~10%
Base
Series A at $20M pre
~$12-15M (2-2.5×)
~35-45%
Upside
100 hubs; $850M exit
~$48-60M (8-10×)
~85%+
Private & Confidential Guesthouse Companies
06
Collateral Pool

Cross-Collateralized Real Estate Security

$11M property value backing $6M instrument

Property
Current
Upside
Horan House
$4.6M
$8.0M
Titus House
$2.2M
$3.0M
Vacant Land
$300K
$1.0M
Palm Springs
$3.875M
$5.875M
Total
$10.975M
$17.875M
Current Coverage
1.83×
$10.975M / $6M
Upside Coverage
2.98×
$17.875M / $6M
Private & Confidential Guesthouse Companies
07
Conversion Mechanics

From Debt to Equity

Clear path from secured position to ownership stake

1

Investment

Secured convertible note with RE collateral protection from day one.

2

Accrual

10% simple interest accrues. No cash payments—adds to conversion amount.

3

Trigger

Qualified financing triggers conversion at 20% discount or $8M cap.

4

Ownership

Security releases. Investor becomes equity holder with pro-rata stake.

Valuation Cap
$8M
Discount
20%
Maturity
36 mo
Private & Confidential Guesthouse Companies
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Use of Proceeds

Capital Deployment Strategy

PropCo assets + OpCo growth

PropCo
$4.4M
Mezz payoff (Horan) $1.2M
Seller notes $0.8M
Palm Springs costs $1.5M
Improvements $0.9M
OpCo
$1.6M
Working capital $0.6M
Pantry buildout $0.4M
Technology $0.3M
Team expansion $0.3M

Milestone Unlock

Second campus operational = model validation. Unlocks Series A positioning.

Target Q1 2027
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The Hub Model

What Halls Do

Centralized operations serving distributed properties

🍳

Commercial Kitchen

Commissary operations serving all properties within 15-minute radius.

85%
Service Margin
🛒

Pantry Ordering

Guest app for provisions and MRE meals. Capture ancillary revenue.

$400
Daily / Guest
🎯

Concierge Hub

Centralized guest services and revenue optimization.

+300bps
vs. STR Margin
8-10
Properties / Hub
$3.9M
Annual Revenue
6.2×
Revenue / CAPEX
9.8%
Unlevered Yield
Private & Confidential Guesthouse Companies
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Structure Comparison

Why This Instrument

Best of both worlds: debt security + equity upside

Feature
Pure Equity
Straight Debt
SAFE
Hybrid
RE Collateral
✕
✓
✕
✓
Equity Upside
✓
✕
✓
✓
Downside Protection
✕
✓
✕
✓
Accruing Interest
✕
◐
✕
✓
Conversion Discount
✕
✕
✓
✓
Valuation Cap
✕
✕
✓
✓
Private & Confidential Guesthouse Companies
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Why Now

Platform Inflection Point

From proof of concept to scalable model

Expansion Roadmap

1
Now
→
2
2026
→
10
2027
→
100
2030
The Stripe Thesis

"Like Stripe built payment rails for commerce that already existed, we're building hospitality rails for group stays that are already happening."

Skift 50 to Watch

"Travel trends point toward quiet luxury, personalization, and meaningful connections. Guesthouse combines all to form an entirely new category."

67%
Travel is 2+ rooms
+300bps
Margin vs. STR
$511B
US Group TAM
0
Competitors
Private & Confidential Guesthouse Companies
12

The Floor

$11M in real estate collateral protects principal. Even in downside, investors recover 1.0-1.3× via asset liquidation.

The Ceiling

Platform scale to 100 hubs targets $850M exit. Early investors positioned for 8-10× returns at 85%+ IRR.

Instrument Summary

$6M
Principal
10%
Interest
$8M
Cap
20%
Discount

Venture returns, secured by real property.

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