Building a Short-Term Rental Empire: Lessons from Elliot Caldwell
The short-term rental industry is undergoing a transformation, and at the forefront of this movement is Elliot Caldwell, the CEO of Home Team Vacation Rentals. In just over two years, Elliot has built a short-term rental empire comprising 12 businesses under the Home Team Collective umbrella, generating a projected $200 million in topline revenue this year. His journey from collegiate baseball player to real estate mogul is nothing short of inspirational.
From Baseball to Business: The Making of an Entrepreneur
Elliot’s story starts in South Carolina, where he grew up in a blue-collar household. A determined and hardworking baseball player, he used sports as a gateway to higher education, eventually attending the University of South Carolina. Though his baseball career didn’t extend to the major leagues, the resilience and perseverance he learned on the field have played a crucial role in his business success.
After briefly working as a teacher, Elliot moved into high school sports fundraising and quickly worked his way up from a sales rep to a partner in the company. However, the entrepreneurial itch led him to take the leap into short-term rental property management and real estate investing.
Building the Home Team Empire
In August 2022, Elliot launched Home Team Vacation Rentals as a management company. Since then, Home Team Collective has expanded to include a construction company (B&B Construction), a property acquisition service (B&B TurnKey), a luxury realty division, a short-term rental realtor search platform (STR Realtor Search), and soon-to-launch ventures in lending, insurance, and tax advisory services.
One of the key differentiators of Home Team’s approach is its commitment to a holistic investment strategy. Rather than simply managing properties, they help clients with every step—from finding and financing properties to designing and marketing them. With an impressive track record of signing up over 30 new investors per month through B&B TurnKey, Home Team has positioned itself as a leader in the space.
Secrets to Short-Term Rental Success
According to Elliot, successful short-term rental investing isn’t just about buying a property and listing it on Airbnb. It requires careful market research, strategic amenities, and a long-term vision. Here are some of his key insights:
Aim for 20% Revenue-to-Purchase Price Ratio: A strong investment property should generate at least 20% of its purchase price in annual revenue. For example, a $1 million property should ideally bring in $200,000 per year.
Focus on What Competitors Lack: Instead of just meeting the market’s standards, identify missing amenities and unique design elements that can set your property apart.
Maximize Tax Advantages: Many investors leverage bonus depreciation and cost segregation studies to reduce taxable income, sometimes saving hundreds of thousands of dollars in the process.
Self-Management vs. Hiring a Property Manager: While Home Team offers property management services, Elliot encourages first-time investors to self-manage for at least a short period to understand the process and maximize profitability.
Entrepreneurship and Work-Life Balance
Despite his company’s rapid growth, Elliot emphasizes the importance of work-life balance. With two young sons, he makes sure to prioritize family time, including weekly lunch dates with his wife and engaging in his kids’ activities.
He believes that success is more than just financial gain—it’s about building a life where he has the freedom to spend time with loved ones while making a meaningful impact.
The Future of Home Team and Short-Term Rentals
Elliot has no plans of slowing down. With new businesses launching, continued expansion, and a focus on helping investors navigate the ever-changing short-term rental landscape, Home Team Collective is set to redefine the industry.
For those looking to break into short-term rental investing or take their portfolio to the next level, Elliot’s advice is simple: work hard, focus on value creation, and leverage every tool available to maximize profitability.
Learn More on the Showplace Podcast
If you’re interested in hearing more about Elliot’s journey and the evolving short-term rental market, be sure to check out the Showplace Podcast, hosted by Justin Miller. Each episode dives into industry trends, expert insights, and strategies for maximizing rental property success.
Showplace is committed to helping short-term rental owners furnish and optimize their properties with ease, ensuring they stand out in an increasingly competitive market. To learn more about Showplace and how they can help elevate your rental business, visit showplacehq.com.