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 115-property short-term rental business—all in just three years. Her journey is a testament to resilience, reinvention, and the power of daring to believe in something bigger for yourself.

Ashley opens up about the pivotal moment she discovered Airbnb, transforming her four-acre property into a surprising income stream. What started as a survival strategy quickly became a passion-driven business that redefined her career and her sense of purpose.

We dive into the entrepreneurial strategies that fueled her rapid growth—from scaling one unit into 115, to building a powerhouse team of predominantly women, to designing systems that keep her business thriving. Alongside the practical insights, Ashley shares the mindset shifts, faith, and intuition that became the foundation of her success.

This is more than a business story—it’s a masterclass in courage, vision, and personal growth. Ashley’s journey will inspire you to see challenges as stepping stones, trust your intuition, and embrace the kind of bold thinking that can transform both life and business.

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.”

Let’s Connect:

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