Understanding the many facets of STR property management isn't just helpful—it's essential. Whether you're a newcomer testing the waters or a seasoned operator looking to scale, mastering the business side of STRs can significantly increase the value of your real estate portfolio.
Few people embody this blend of financial acumen and hospitality know-how better than Fred Boothby, founder of Enjoy Unique Stays.
Table of Contents
In this post, we unpack Fred’s journey from an accidental host to a thriving STR entrepreneur and explore the strategies he’s used to build a profitable and meaningful business rooted in both financial performance and exceptional guest experiences.
The Unlikely Beginning: A Path from Finance to Hospitality
Fred didn’t start in hospitality—far from it. Armed with a degree in finance and a background in commercial lending, he envisioned a different future, one that veered more toward entrepreneurship than hospitality. A move to Florida to run a lawn care business marked the first step away from corporate finance.
But life had other plans. When his wife traveled for extended periods, Fred began listing their home on Airbnb. At first, it was simply a way to offset household expenses. But what started as a side hustle quickly turned into something more—something that tapped into his entrepreneurial instincts and financial training.
From Casual Hosting to Intentional Investing
The Boothbys' early experience with home-sharing revealed two powerful things: the emotional joy of connecting with travelers and the tangible upside of earning income from underutilized assets. As Fred analyzed the returns, he realized this was more than a temporary gig—it was a scalable business opportunity.
He saw how short-term rentals, when managed effectively, could outperform long-term leases, and he began to apply the same financial lens he used in banking to evaluate rental properties, revenue potential, and operating costs.
Learning to Play the Market: Seasonal and Geographic Arbitrage
One of the smartest strategies Fred adopted was playing to the strengths of seasonal demand. By spending winters in Michigan—where short-term rental demand is typically lower—and summers in Florida, where the STR market thrives, he optimized both lifestyle and revenue.
This geographic arbitrage allowed him to keep living costs low while operating his business where demand (and nightly rates) were high. It also gave him the flexibility to grow the business without being tied to a single location year-round.
Establishing a Business Blueprint
By 2018, Fred transitioned from a hands-on host to a strategic investor and operator. He focused on expanding his portfolio with a unique angle—seeking out distinctive, story-worthy properties that guests couldn’t find anywhere else.
His background in finance gave him an edge. He began using creative financing models to fund new acquisitions, taking advantage of nontraditional deal structures and seller motivations to negotiate favorable terms.
Creative Financing: Understanding the Psychology of Sellers
Fred discovered that real estate isn’t just about numbers—it’s about people. When purchasing properties, he looked beyond listing prices and traditional mortgages. Instead, he focused on structuring deals that addressed the long-term goals and financial motivations of sellers.
This might include seller financing, flexible contract structures, lease-to-own arrangements, or delayed closing terms that created win-win scenarios. By understanding what sellers valued—whether it was income stability, tax deferment, or legacy—Fred could craft offers that were attractive and financially sound.
Why Property Management Matters
As his portfolio grew, Fred faced a pivotal decision: continue managing the properties himself, or build infrastructure to scale. He opted for both—starting with his own properties and eventually offering third-party property management services to other owners.
This move wasn’t just about growth—it was about control. Managing his own portfolio allowed him to uphold the quality standards that defined Enjoy Unique Stays. Offering management to others added a new revenue stream, but also required a new level of professionalism, systems, and team support.
Navigating the Challenges of Third-Party Management
Third-party management brought its own complexities. Fred had to balance the expectations of property owners, maintain clear communication, and stay on top of regulations and compliance issues.
He also had to refine his onboarding and operations processes to ensure that each new property added to the portfolio was aligned with his brand and revenue goals. Trust and transparency became non-negotiable elements in building long-term relationships with owners.
Focusing on Metrics that Drive Profitability
Fred doesn’t guess when it comes to business performance—he measures. Some of the core metrics he tracks include:
-
Customer acquisition cost
-
Owner retention rate
-
Lifetime value of a client
-
Revenue per available night (RevPAN)
-
Operating margin per property
By regularly reviewing these numbers, he ensures that every decision is backed by data, helping him identify which strategies are working and where there’s room for improvement. This focus on metrics not only supports operational efficiency but can also lead to a revenue increase.
The Role of Technology in Scaling
Fred credits much of his growth to the use of technology. From property management software (PMS) to dynamic pricing tools, channel management and automation have been essential in maintaining efficiency and providing a seamless guest experience. Additionally, his team focuses on guest messaging and support tools to create a timely, welcoming atmosphere for all visitors. This has been a key factor in his portfolio growth.
The right tech stack allowed his team to focus less on repetitive tasks like housekeeping and maintenance and more on strategy, guest relations, and business development, supported by centralized calendars and CRM systems.
This digital backbone is what enabled Fred to scale from one listing to many—without sacrificing quality. To ensure safety and satisfaction, the team also emphasizes guest screening and guest vetting to guarantee a smooth experience.
-
Fred also uses digital guidebooks and smart home devices to enhance guest experiences.
-
3D virtual tours are utilized to showcase properties and attract more bookings.
Marketing in the Digital Age: Social Media as a Booking Engine
In today’s crowded market, traditional marketing isn’t enough. Fred invests in social media not just to promote his properties, but to create emotional connections with potential guests. By showcasing unique architecture, natural surroundings, and personal touches, his listings often gain traction through organic shares and word-of-mouth.
For Fred, the goal isn’t just to get seen—it’s to be remembered.
Vision for the Future: Experiential and Nature-Driven Stays
Looking ahead, Fred is doubling down on what makes his brand different: uniqueness. His future plans involve building and managing properties that deliver unforgettable, nature-based experiences, focusing on customer experience. Whether it’s a treehouse in the woods or a waterfront cabin with kayaks, his focus is on helping people reconnect—with nature, with each other, and with themselves. Fred also values guest recommendations and carefully considers unit selection for each property.
Building a Purpose-Driven Team
Fred knows that building a great company takes more than systems—it takes people. That’s why he puts a strong emphasis on company culture, hiring team members who align with his values and share a passion for hospitality. Empowering his team has become central to creating consistent guest experiences and long-term success.
Final Takeaways: The Blueprint for STR Success
Fred Boothby’s story offers more than inspiration—it offers a framework. From his accidental beginnings to strategic scaling, he demonstrates how financial intelligence, people skills, and operational excellence come together in a successful vacation rental business.
If you’re aiming to grow your STR business, consider these key takeaways:
-
Use financial data to drive decisions
-
Understand the motivations behind every deal
-
Invest in technology to scale without burning out
-
Build meaningful guest experiences that stand out
-
Prioritize trust in every owner and guest relationship
Success in STRs isn’t just about occupancy—it’s about creating value across every touchpoint.
Ready to learn more?
Explore Fred Boothby’s work at Enjoy Unique Stays for more insights into building a purpose-driven short-term rental business.
FAQ
1. How did Fred Boothby get started in short-term rentals?
Fred began hosting by chance when he rented out his home on Airbnb while his wife was away. What started as a way to cover expenses quickly evolved into a serious business opportunity.
2. What makes Fred’s approach to STRs unique?
Fred combines his background in finance with a deep understanding of hospitality. He focuses on creative financing, market dynamics, and offering unique guest experiences that go beyond typical rentals.
3. Why is seasonal strategy important in short-term rentals?
Fred’s success was partly due to his ability to leverage seasonal demand by alternating between low-demand and high-demand regions. This allowed him to maximize income while minimizing costs.
4. How does Fred acquire new properties?
He uses creative financing methods, often negotiating directly with sellers to find mutually beneficial terms. His experience in commercial lending helps him structure deals that unlock long-term value.
5. What are some key challenges of third-party property management?
Fred highlights the complexity of managing other owners’ properties, including setting expectations, ensuring compliance, and maintaining strong communication and transparency.
6. Which performance metrics does Fred track to ensure profitability?
Key metrics include customer acquisition cost, retention rate, lifetime value of property owners, revenue per night, and operating margins. These help him stay financially informed and scalable.
7. What role does technology play in Fred’s business?
Technology is foundational to his operations. He uses property management software and automation tools to streamline tasks, improve efficiency, and enhance guest experience.
8. How does Fred use social media to drive bookings?
He markets visually compelling and unique properties with viral potential. Instead of relying solely on OTAs, he uses social channels to build brand visibility and attract direct bookings.
9. What is Fred’s long-term vision for Enjoy Unique Stays?
Fred is focused on growing a portfolio of experiential, nature-based properties. His goal is to create memorable stays that connect guests with meaningful experiences and natural beauty.
10. What advice does Fred give to new or growing STR operators?
Understand your numbers, build trust with owners and guests, use technology to scale, and focus on delivering unique guest experiences. Long-term success depends on consistency, creativity, and smart management.