Ashley Freeman: What Winning Means Now

Ashley Freeman Episode Show NotesAshley Freeman never set out to build one of Oxford’s largest short-term rental management companies.Before Velvet Ditch Villas, many people around Oxford knew her simply as Coach Ashley. But after a difficult season of life led her to begin renting her own home, what started as a way to make some extra income quickly grew into something much bigger.In this conversation, Ashley talks about the early days of the business, working until 4 a.m. while juggling coaching, motherhood and rentals, and the people who believed in her before she fully believed in herself.We also talk about a mission trip to Belize that changed the way she thought about relationships and service, her fiercely competitive personality, building and leading a team, raising her daughter Lucy, becoming more comfortable putting herself out there publicly, and the role faith plays in how she thinks about success and the future.Ashley also shares her perspective on Oxford’s rapidly changing short-term rental market, why the business may eventually expand beyond Oxford, and what she hopes the next chapter of her life will be about beyond simply managing more properties.In this episode:Life before Velvet Ditch Villas and the days of “Coach Ashley” 🎾A lesson from Belize that shaped how Ashley sees peopleHow renting her own home unexpectedly became a businessThe 4 a.m. season of trying to do everything herselfWhy competitiveness has been one of her biggest strengthsLearning to believe in herself as a leaderBuilding a team and helping other women recognize what they are capable ofMotherhood and what she hopes her daughter learns from watching herBecoming more visible through social media and personal brandingAshley’s take on Oxford’s evolving short-term rental marketFaith, purpose and what success means to her nowFind Ashley and VDV at:Velvet Ditch Villas: thevelvetditchvillas.comInstagram: @ashleyfreemanofficialVelvet Ditch Villas on Instagram: @velvet_ditch_villasBeyond the Square is hosted by Blake Thompson and features conversations with the people, places and stories that make Oxford, Mississippi what it is.