Built by Operators.
Not Just Investors.
The Lookout Towers team brings together hospitality development, real estate finance, and short-term rental operations — a business built by people who have done it before.
Leadership & Track Record
The Team Behind The Vision.
85+ years of combined experience in real estate development, private equity, and hospitality operations.
$300M+
CAPITAL DEPLOYED
85+
YEARS COMBINED EXPERIENCE
23
TOWERS LAUNCHED
90%+
OCCUPANCY RATE
$300M+
CAPITAL DEPLOYED
85+
YEARS COMBINED EXPERIENCE
23
TOWERS LAUNCHED
90%+
OCCUPANCY RATE
Why We're Uniquely Positioned
The edge isn't just the product. It's who builds it.
01
Operators First
We don't just develop — we operate. Every design decision is made through the lens of a guest experience that drives 5-star reviews, repeat bookings, and premium nightly rates. We've run the numbers from inside the property, not from a spreadsheet.
02
Vertical Development Expertise
Designing and permitting a structurally elevated structure in a forested environment is not a standard development challenge. Our team has navigated the engineering, environmental review, and local permitting processes that stop most developers before they start.
03
STR-Native Underwriting
We underwrite every deal using STR-specific metrics: ADR, occupancy curves, RevPAR, and platform positioning — not cap rates designed for apartment buildings. This makes our projections more conservative and our actual performance more predictable.
04
Repeatable Playbook
The first tower teaches you everything. Our site selection criteria, construction specs, furnishing program, and platform launch process have been systematized into a repeatable model — which is what makes this scalable, and what makes your investment more than a one-off bet.
01
Operators First
We don't just develop — we operate. Every design decision is made through the lens of a guest experience that drives 5-star reviews, repeat bookings, and premium nightly rates. We've run the numbers from inside the property, not from a spreadsheet.
02
Vertical Development Expertise
Designing and permitting a structurally elevated structure in a forested environment is not a standard development challenge. Our team has navigated the engineering, environmental review, and local permitting processes that stop most developers before they start.
03
STR-Native Underwriting
We underwrite every deal using STR-specific metrics: ADR, occupancy curves, RevPAR, and platform positioning — not cap rates designed for apartment buildings. This makes our projections more conservative and our actual performance more predictable.
04
Repeatable Playbook
The first tower teaches you everything. Our site selection criteria, construction specs, furnishing program, and platform launch process have been systematized into a repeatable model — which is what makes this scalable, and what makes your investment more than a one-off bet.
The Team
The Team
Operators, developers, and designers who have built, launched, and managed luxury short-term rental properties from the ground up — not from a spreadsheet.
Doug Crawley
Chairman and CEO
Co-founder and partner in multiple real estate companies since 1999. Specializes in designing, building, and managing residential and commercial properties. Experience in homes, hotels, condos, apartments, and Class A office spaces. Expertise in investment properties, fractional ownership, and real estate development.
Rob
Director of Real Estate
Experienced real estate professional overseeing property acquisitions, development planning, and project execution. Focused on identifying strategic opportunities, maximizing asset value, and supporting the company's long-term growth objectives.
Whitney Scott
Chief Operations Officer
15+ years of executive leadership in hospitality, strategy, and operations. Former KOA CMO and SVP of Strategy and former Terramor COO. Co Founder of Walden and advisor to leading outdoor hospitality and venture organizations.
Danny Perez
Fund Manager
20+ years banking experience with Wells Fargo, specializing in high-value lending and financial strategy. Senior Debt Specialist with over $1 billion in funded loans, including commercial real estate and private lending. Founder & CEO of Wealth Asset LLC, experts in Structured Finance, including debt restructuring, asset-backed lending, and capital markets.
Brad Kerr
Director of Finance
Specialist with over $1 billion in funded loans, including commercial real estate and private lending. Founder & CEO of Wealth Asset LLC, experts in Structured Finance, including debt restructuring, asset-backed lending, and capital markets.
Chuck Brazel
Director of Investor Relations
15 years Executive Director of Southern Cross Real Estate Investment Group. Specialist in emerging resort and travel destinations in the US and around the world. 25 years in national recruitment of physicians and physician assistants.
Chelsea Bristow
Investor Relations
Extensive leadership experience spanning capital raising, investor relations, operations, and business development, including roles as Chief Operating Officer and Director of Operations across multiple organizations, with a strong foundation in the medical industry directing surgical practices within a multi-provider medical group.
Lee Giove
Investor Relations
4 years in venture capital funds: investment analyst, capital raising and investor relations. Risk & Financial Due Diligence Consultant at Risk Advisory Europe. Dual Master's Degrees in Innovation & Industrial Management and Knowledge-Based Entrepreneurship from Gothenburg University School of Business, Economics and Law.
Timothy Shelton
Fund Admin
Real estate investor, fund operator, and consultant specializing in multifamily and self-storage investments. Through his fund and consulting platform, he partners with investors and operators to structure deals, allocate capital, and optimize performance, leveraging institutional-level underwriting and hands-on operational experience.
Scott Cleveland
Head of Marketing
Marketing executive with over a decade of experience driving growth across outdoor hospitality, real estate, and private equity-backed businesses. Specializing in scaling emerging brands, increasing market share, and creating high-performing marketing systems that accelerate customer acquisition and long-term revenue growth.
Track
Record
Numbers speak louder than bios. Here is what we have delivered — across projects, capital, and investor returns.
Projects Delivered
Completed and operational
Total Capital Deployed
Across all projects
Average Investor Return
Realized, across exits
Years in Operations
Combined team experience
Deals get done by teams you trust.
Schedule a call to meet the team directly and ask every question you have.
Address
Contact
IG
FB
TW
LI
© 2026 The Lookout Towers. All rights reserved.
The financial projections presented on this page are illustrative only and not a guarantee of returns. Investing in real estate involves risk. Consult a qualified financial advisor before making investment decisions.
Experience
A Career in Deals, Not Decks.
2022 – Present
Founder & Managing Partner
Lookout Towers Fund
Launched a vertically integrated hospitality real estate fund. 23 towers developed, $300M+ pipeline, 90%+ occupancy.
2017 – 2022
Director of Acquisitions
National Hospitality Group
Led $150M in acquisitions across boutique hotel and short-term rental portfolios in high-demand tourism markets.
2013 – 2017
Development Manager
Coastal Properties LLC
Managed ground-up development of luxury vacation rentals and mixed-use properties across the Southeast.
2009 – 2013
Associate, Real Estate Private Equity
Summit Capital Partners
Underwrote and structured investments in value-add multifamily and hospitality assets.
WHY US
What Sets This Apart
Operator-founded, not finance-first
Real assets, not paper promises
12-month exit option for Series A
10% annual vacation credit on investment
SEC 506(c) compliant structure
IRA / 401(k)-eligible investments
Uniquely Positioned to Win.
Vertically Integrated
We control every stage — from land acquisition and design to construction, branding, and management. No middlemen, no margin leaks.
Proven Demand
Two towers sold out in two hours on launch day. 5,000+ VIP waitlist. The product is the moat — iconic, scarce, and shareable.
Institutional Governance
Third-party fund administration by Avestor. Independent reporting, monthly distributions, and full investor transparency.
Advisors & Partners
Backed by Industry Leaders.
Richard Harmon
STRATEGIC ADVISOR
Former VP at Hilton Hotels, 30+ years in hospitality development & operations.
Dr. Sarah Chen
FINANCIAL ADVISOR
Managing Director at Goldman Sachs (Ret.), real estate PE specialist.
Avestor
STRATEGIC ADVISOR
Former VP at Hilton Hotels, 30+ years in hospitality development & operations.
Richard Harmon
STRATEGIC ADVISOR
Former VP at Hilton Hotels, 30+ years in hospitality development & operations.
Dr. Sarah Chen
FINANCIAL ADVISOR
Managing Director at Goldman Sachs (Ret.), real estate PE specialist.
Avestor
STRATEGIC ADVISOR
Former VP at Hilton Hotels, 30+ years in hospitality development & operations.