The Short Term Show Scaling to 100+ Rentals: The Grit & Growth of Tennis Pro Ashley Freeman
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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.
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From Tennis Pro to STR Host
- Ashley Freeman, a former tennis pro, became an accidental short-term rental entrepreneur after a divorce.
- She started with her five-bedroom house in Oxford, Mississippi, and earned over $25,000 in the first year.
Rapid Scaling in Oxford
- Ashley expanded from her initial properties to over 100 units in under three years.
- This rapid growth was fueled by leveraging her local network and social media presence.
Competitive Edge in College Towns
- Leverage local knowledge and connections for success in short-term rentals.
- A competitive edge in understanding the local market is crucial.
