The vacation rental industry is constantly evolving, and Fred Boothby, CEO of Enjoy Unique Stays, is leading the way with a fresh approach to experiential stays. In our latest episode, Fred shared his journey from accidental host to industry innovator, his insights on scaling across multiple states, and how he’s leveraging technology to stay ahead.
From Accidental Host to Industry Leader
Fred’s journey into vacation rentals wasn’t planned. What started as a side project renting out his home quickly turned into a full-scale business. Over time, he expanded his portfolio to 140+ properties across multiple states, embracing experiential stays - properties designed to offer guests something far beyond a place to sleep.
But growth came with challenges. Fred soon realized that branding, culture, and team alignment were just as crucial as property management.
Turning Challenges Into Opportunities
One of the biggest takeaways from Fred’s journey is the importance of perspective. He initially saw secondary and tertiary markets as a limiting factor - until industry leader Steve Schwab gave him a new outlook.
This shift in thinking allowed Fred to see hidden potential in the markets he was operating in, turning what seemed like limitations into strategic advantages.
The Role of Branding and Culture in Scaling
As Enjoy Unique Stays grew, Fred realized that simply acquiring properties wasn’t enough - building a strong brand and company culture was critical to long-term success.
He focused on:
✅ Creating a distinct brand identity that aligned with experiential travel
✅ Investing in team culture to keep employees engaged and motivated
✅ Standardizing guest experiences across diverse properties
Fred emphasizes that in order to scale successfully, you need team buy-in and a shared vision.
Technology as a Game-Changer
Managing multiple properties across different markets comes with operational complexities. Over the years, Fred has worked with various property management systems (PMS) to streamline his business, including:
- Enterprise-level solutions that were too complex for smaller operations
- User-friendly platforms that lacked advanced scalability
- AI-powered solutions that are helping redefine efficiency
Through trial and error, he found the right tech stack that could support his diverse portfolio and help his team work smarter, not harder.
Lessons from Disaster: The Importance of Resilience
One of the toughest challenges Fred faced was recovering from a hurricane that devastated parts of his market. Unlike coastal regions where insurance often covers damages, the affected areas in North Carolina faced major setbacks without financial relief.
This experience reinforced the importance of:
- Disaster preparedness for vacation rental operators
- Having a risk management strategy to safeguard business operations
- Building a flexible, resilient business model
What’s Next for Enjoy Unique Stays?
Looking ahead, Fred is focused on:
- Expanding his brand while maintaining high-quality guest experiences
- Leveraging AI and automation to optimize operations
- Exploring new markets and untapped opportunities
His story is a reminder that adaptability, perspective, and smart business decisions can turn challenges into growth opportunities.
Final Thoughts: Are You Looking at Your Business Through the Right Lens?
Fred’s insights challenge vacation rental operators to rethink their approach:
- Are you seeing opportunities where others see obstacles?
- Is your brand and culture strong enough to scale?
- Are you leveraging the right technology to stay ahead?
