The Short Term Show
Scaling to 100+ Rentals: The Grit & Growth of Tennis Pro Ashley Freeman
Mar 19, 2025
Ashley Freeman, a former tennis pro and now a short-term rental powerhouse, shares her inspiring journey managing over 100 properties in Oxford, Mississippi. She reveals the unique challenges and advantages of investing in college towns, leveraging local insights for success. Ashley discusses how her athletic background instilled resilience and competitiveness in her business approach. The conversation also covers innovative property management strategies and the continuous demand for rentals in a dynamic college environment, along with tips for aspiring investors.
30:36
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Quick takeaways
- Ashley Freeman's transition from tennis pro to short-term rental owner showcases the power of local knowledge and adaptability in building a successful rental business.
- The importance of grit, customer service, and community engagement is essential for maintaining competitive advantage in the fluctuating short-term rental market.
Deep dives
The Journey from Tennis Pro to Short-Term Rental Success
The host interviews Ashley Freeman, who transitioned from being a tennis pro to a successful short-term rental owner in a college town. After an unexpected divorce, she explored the emerging Airbnb market, which allowed her to earn significant income from her five-bedroom home. In just a few years, Ashley expanded her portfolio to over 100 properties, leveraging her local knowledge and connections to thrive in a competitive market. Her journey emphasizes the importance of adaptability and having a solid plan in the short-term rental landscape.
