OCTOBER 21, 2025
#155 Short-Term Rental Success: How Ashley Freeman Built a 115-Property Empire
How do you rebuild your life—and create extraordinary success—after everything falls apart?
In this episode, I sit down with Ashley Freeman, a former tennis pro who turned the pain of divorce into the fuel for a thriving short-term rental business that now spans 115 properties. Her story is one of resilience, reinvention, and the courage to dream bigger when the odds are stacked against you.
From Surviving to Thriving
Ashley’s journey to short-term rental success began with a single leap of faith. After her marriage ended, she was determined to find a new path forward. When she discovered Airbnb, she decided to list her four-acre property—just to see what would happen.
What started as a survival move quickly turned into something far greater. Guests loved her space, and soon, Ashley realized she had uncovered not just an income stream—but a calling.
Within three years, she scaled from one property to 115, proving that mindset, systems, and purpose-driven action can completely transform your trajectory.
How She Scaled Her Short-Term Rental Business
Ashley’s approach to building a short-term rental business is deeply strategic. She credits her success to:
- Building the right team – predominantly women who share her values and vision.
- Creating efficient systems that keep operations running smoothly at scale.
- Focusing on guest experience as the cornerstone of her brand.
These decisions didn’t just help her grow—they helped her lead with intention and sustainability.
The Mindset Behind Short-Term Rental Success
At the heart of Ashley’s growth is her mindset. She shares how faith, intuition, and a strong belief in her ability to rebuild became the foundation of her success.
Instead of letting fear or failure define her, Ashley chose to see each challenge as an opportunity. Her story reminds us that success in short-term rentals isn’t just about numbers—it’s about vision, consistency, and believing in what’s possible.
Lessons for Anyone Building a Short-Term Rental Empire
If you’re dreaming of scaling your short-term rental business, Ashley’s blueprint offers practical inspiration:
- Start small, but think big.
- Invest in people and processes early.
- Let your “why” drive your “how.”
This episode is a powerful reminder that growth starts with courage—and that success is possible no matter where you’re starting from.
Ready to learn from Ashley’s journey? Listen to the full episode and discover how she turned adversity into one of the most inspiring stories of short-term rental success.
HIGHLIGHTS AND KEY POINTS:
[00:56] A short introduction about our guest Ashley Freeman and her unexpected journey from tennis pro to scaling a 115-property management company in under three years
[06:37] Ashley shares her mission-driven approach to short-term rentals and her passion for helping others after finding purpose again
[11:28] Ashley’s journey from her first client to managing 135 properties, and how she learned to grow with humility, faith, and adaptability
[15:38] How surrendering control to God after Ashley’s divorce transformed her life and taught her to recognize His guidance
[18:48] Ashley shares how a trip to Africa ignited her mission to reach “broken women” and how she learned to trust whispers from God
[25:10] Ashley’s approach to starting simple and building her property management growth one step at a time
[26:49] Ashley’s team growth and systems that transformed her property management business
[30:18] Ashley’s share her intentional decision to keep cleaning in-house as part of building a trusted team and aligning hospitality with her deeper mission to serve guests with excellence
[35:10] How building systems and processes early allowed Ashley’s business to scale smoothly and avoid breakdowns during rapid growth
[38:44] Ashley’s biggest challenges as she has grown her property management company to now well over 100 units and how she navigated them
[43:12] How I sustain my team by focusing on open communication, removing roadblocks, and empowering them to contribute solutions that strengthen the company
[49:39] The lightning round
Golden Nuggets:
- “I do think there’s a sense of faith that you have to have in business, regardless if you believe in the Lord or not. You know you have to have faith. It’s that leap of faith that you’re taking to even get started.”
- “God is talking to each of us; we have to be willing to open our ears to listen.”
- “Cleaning, to me, is like the most important part of the experience, and so we’ve never even considered trying to go out and hire third party cleaners, because they just don’t get it. There’s a difference between a regular clean and an Airbnb clean, and we all know that.”
- “The hospitality industry is our mission field, and so we’re serving these clients that come in by giving them experiences that they’ll never forget.”
- “Do not take all the complaints and the negative feedback personally.”
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